CZ304798A3 - Biologically degradable substances for softening fabrics and preparations for softening fabrics in which such substances are comprised - Google Patents

Abstract

Fabric softening actives having hydrophobic moieties containing, preferably, ester, or amide, linkages and mixed branched and unsaturated hydrophobic groups provide improved processing and stability as well as surprisingly good softening. Preferred compositions contain mono-ol and diol principal solvents having a ClogP of from about 0.15 to about 0.64, that have the ability to make clear aqueous fabric softener compositions containing relatively high concentrations of the said fabric softener actives having ester linkages in their long, hydrophobic chains. Other solvents may be present. Premixes of the fabric softening actives, the principal solvents, and, optionally, other solvents are useful in the preparation of complete formulations by obviating/limiting the need for heating. Other compositions can be prepared which are solid or dispersions of the said fabric softening actives.

Description

Biodegradable fabric softeners and fabric softener preparations containing these substances

Field of technology

This invention relates to substances and/or preparations suitable for fabric softening, preferably translucent and more preferably clear aqueous concentrated liquid preparations for fabric softening. This invention particularly relates to substances and/or preparations for softening fabrics, which are suitable for use during rinsing, following the washing of fabrics, with which excellent softening and antistatic effects are achieved and which, e.g. characterized by a reduced tendency to stain, excellent dispersibility in water, excellent rewetability and/or viscosity stability and stability when stored at temperatures lower than room temperature, i.e. at temperatures lower than, for example, 25°C.

Current state of the art

Clear, concentrated preparations used to treat fabrics are known from the prior art. For example, European Patent Application No. 404,471, by Machin et al., published on December 27, 1990, describes an isotropic liquid preparation for fabric softening, with at least 20% by weight of an active ingredient, and at least 5% by weight of an organic acid with short chain.

The subject of this invention are the active ingredients of concentrated, preferably clear and aqueous liquid preparations for softening fabrics, which preferably contain a small amount of organic solvents (less than 40% by weight, based on the total weight of the preparation) and are characterized by increased stability (i.e. remaining clear or transparent and does not precipitate, gel, thicken or solidify during long-term storage) at normal temperature, i.e. at room temperature and at temperatures below room temperature. These preparations also have a reduced tendency • ·

► · · · • · · ··· · · • · · • · * · and antistatic moistening, as well as for creating stains on fabrics, they are well dispersible in cold water and are characterized by excellent softening properties and an excellent ability to repeat and slow the increase in concentration of wetting agent residues and excellent melting point stability. In order to obtain such preparations, however, it is necessary that their active substance is characterized by considerable fluidity. Such active substances can be prepared using unsaturated materials, but these materials cause significant problems, which include their chemical instability and lower softening efficiency compared to saturated substances.

Brief description of the invention

The active substances of the fabric softening preparations according to the present invention are biodegradable and contain ester bonds in long hydrophobic chains. They contain both branched and unsaturated acyl chains. These active substances preferably have the general formula:

1.

(R)4.mN( ⁺ )-[(CH ₂ ) _n -YR ¹ ]m x<->

(1) is hydrogen or a short chain C^^-Cg,

----------- --------------- ~ _b , " preferably C^-C^-alkyl / hydroxyalkyl, for example methyl (most preferred), ethyl, propyl, hydroxyethyl, and the like, benzyl, or mixtures thereof, m is or 3, preferably 2, nj to 4, preferably 2, Y is (R)N-(O)C-, -C(O)- N(R)-, or -0(0)-0-,

0-(0)C-, preferably - 0-(0)0-, plus one if there are 6 to 22, preferably the first number of carbon atoms in R ¹

-0-(0)0- or -(R)N-(0)C- (number of YR ¹ ) to 22, more preferably 14 to 20, (R ¹ and YR ^J represent a hydrophobic chain, while the lengths of the R chains expressed by the number of their atoms, are generally even for fatty alcohols and odd for fatty acids), a maximum of one number are interchangeable 1/3

YR ¹ is less than 12 and the second number R 1 or YR ¹ is at least 16, wherein R ¹ is C 5 -C 21 (or C 8 -C 22 ) alkyl, preferably branched or unsaturated ^C 10 -C 20 alkyl ( ^{not C} 8 -C 19 ), branched alkyl or C ₁₂ -C ₁₈ unsaturated alkyl (or ^C n ^-C 17 )< where the ratio of branched alkyls to unsaturated alkyls is 95:5 to 5:95, preferably 75:25 to 25:75, more preferably 50:50 to 30:70, and in the case of unsaturated alkyl groups, the iodine number of the respective fatty acid of this R ¹ group is preferably 20 to 140, more preferably 50 to 130 and most preferably 70 to 115. (For the purposes of this document, branched alkyls are considered such alkyl , which contain a substituent that is hydrophobic, even in those cases where they are connected to the main chain by bonds other than a carbon-carbon bond, such as oxygen as in the case of oxysubstituents, and the iodine number of the corresponding fatty acid, or corresponding fatty acids, is used to determine the degree of unsaturation of the R ¹ group which is the same as the degree of unsaturation of a fatty acid containing the same R ¹ group. If any alkyl R ¹ is branched and unsaturated at the same time, it is considered branched). The counterion X" can be any anion compatible with the active ingredient of the fabric softener, preferably chloride, bromide, methyl sulfate, ethyl sulfate, sulfate, nitrate, more preferably chloride;

2. active substance of the preparation for softening fabrics of the general formula:

RN( ⁺ )CH2CH ³ CH ₂ YR1 (-) (2) where Y, R, R ¹ , and X^^ have the same meaning as before (These substances are substances of the general formula:

[CH ₃ ] ₃ N ⁺ (CH ₂ CH(CH ₂ O(O)CR ¹ O(O)CR ¹ )Cl, where -O-(O)CR ¹ are partially unsaturated acid residues,

for example oleic acids, R is preferably methyl or ethyl R ¹ is C ₁₅ to C ₁₉ alkyl with varying degrees of branching and substitution of the alkyl chain of the chain, and partly branched chain acid residues such as isostearic acid); and

3. mixtures of these substances.

Preparations according to this invention preferably contain:

A. 2 wt.% to 80 wt.%, preferably 13 wt.% to 75 wt.%, more preferably 15 wt.% to 70 wt.% and even more preferably 19 wt.% to 65 wt.% based on the weight of the preparation , active ingredients of a biodegradable fabric softener selected from the group consisting of

1. active substances of the preparation for softening fabrics of the general formula:

(R)4Hn-N( ⁺ )-[(CH2) _n -YR^]m

(1) where R is hydrogen or alkyl or short chain hydroxyalkyl ^c 1 ^c 6' ^preferably C 2 -C 8 alkyl, for example methyl, (most preferred), ethyl, propyl, hydroxyethyl and the like, benzyl, or mixtures thereof, m is 2 or 3, preferably 2, n is 1 to 4, preferably 2, Y is -O-(O)C-, -(R)N-(O)C-, -C(O)-N (R)- or

-C(O)-0-, preferably -O-(O)C-, the total number of carbon atoms in R ¹ , plus one if Y is -O-(O)C- or -(R) N-(O)C- is 6 to 22, preferably 12 to 22, more preferably 14 to 20, but at most one group R ¹ or YR ¹ has less than 12 carbons and the other group R ¹ or YR ¹ at least 16 carbons , where R ¹ is branched and unsaturated alkyl with a long chain ^c 5 ^c 21 ( ^not co Cg-C22)' ^preferably Cg-C _ig (or C ₁₀ -C ₂₀ ), or more preferably C _1;L -C ₁₇ , ( or C ₁₂ -C ₁₈ ) (for example, alkenyl, sometimes referred to as alkylene, or alkyl with multiple double bonds) where the ratio of branched alkyls to unsaturated alkyls is 5:95 to 95:5, preferably 75:25 to 25:75 , more preferably 50:50 to r(-) (2) • , . · · ··· ··· -»·□ -······· »* ♦*

30:70, and in unsaturated alkyl groups, the iodine number of the respective fatty acid of this R ¹ group is preferably 20 to 140, more preferably 50 to 130 and most preferably 70 to 115, and where the counterion X can be any anion compatible with the active substance of the fabric softener , preferably chloride, bromide, methyl sulfate, ethyl sulfate, sulfate, and/or nitrate, more preferably chloride;

2. active substances of preparations for softening fabrics of the general formula:

YR ¹

RN( ⁺ )CH2CH

CH ₂ Yr1 where Y, R, R ¹ , and have the same meaning as in the preceding text;

and

3. a mixture of these substances.

[In one type of preferred biodegradable quaternary ammonium salts suitable for fabric softening use, the C(O)R ¹ is partially derived from unsaturated acids, for example oleic acid and/or from fatty acids and/or from partially hydrogenated fatty acids contained in vegetable oils and/or in partially hydrogenated vegetable oils such as canola oil, oil, safflower oil, peanut oil, sunflower oil, soybean oil, corn oil, beef tallow, rice bran oil, etc., partly from branched-chain fatty acids such as for example from isostearic acid.] [As will be seen from the following text, these biodegradable active ingredients of fabric softeners containing ester linkages are called DEQAs, which designation refers to diesters, triesters, and monoesters containing one to three, preferably two, hydrophobic groups with long chains. The corresponding amide active substances of the preparation and the active substances of fabric softeners based on mixed amides can also contain one to three, preferably two, hydrophobic groups with a long . ^J .Č· groups consisting of: ethoxylate derivatives, chain.];

B. These preparations may also contain less than 40% by weight, preferably 0 to 35% by weight, more preferably 12 to 25% by weight and even more preferably 14 to 20% by weight, based on the total weight of the preparation, of the main solvent with with a ClogP value of 0.15 to 0.64, preferably 0.25 to 0.62 and more preferably 0.40 to 0.60, wherein said main solvent preferably contains insignificant amounts of solvents selected from

2,2,4-trimethyl-1,3-pentanediol, diethoxylate or triethoxylate of 2,2,4-trimethyl-1,3-pentanediol and/or 2-ethylhexyl-1,3-diol and mixtures of these substances which, if used alone, they do not provide a clear and stable product, and which in the concentrations used do not cause a noticeable change in the physical characteristics of the preparation, more preferably these preparations are free of the mentioned solvents and the main solvent is preferably selected from the group listed below;

C. can advantageously also contain an effective amount of low-molecular water-soluble solvents such as ethanol, isopropanol, propylene glycol, 1,3-propanediol, propylene carbonate, etc., sufficient to improve clarity, while these mentioned water-soluble solvents are used in concentrations at which no clear preparation was formed unless additional solvents were present; D. may also preferably contain an effective amount of water-soluble calcium and/or magnesium salts sufficient to improve clarity, wherein these salts are preferably chlorides; and E. and the rest up to 100% is water.

These preparations are aqueous, transparent or preferably clear and contain 3 to 95%, preferably 10 to 80%, more preferably 30 to 70%, and even more preferably 40 to 60% water and 3 to 40%, preferably 10 to 35 %, more preferably 12 to 25%, and even more preferably 14 to 20% of the above-mentioned main solvent B, which is alcohol.

These preferred products (compositions) are not transparent or clear without the presence of the main solvent. The amount of main solvent B required to make the formulation transparent or clear is preferably greater than 50%, more preferably greater than 60%, and even more preferably greater than 75%, based on the total amount of organic solvents present.

• ·

• · · · · « to ··♦· · * · · · •to#·· this *to

These preparations can also be prepared in the form of conventional dispersions of the active substances of fabric softening preparations, containing 2 to 50%, preferably 10 to 40%, more preferably 15 to 30% of the active substance of the fabric softening preparation. These preparations can also be prepared as solids, either as granules or embedded in substrates, as described below.

The pH values of these aqueous preparations should be in the range of 1 to 7, preferably in the range of 1.5 to 5, more preferably in the range of 2 to 3.5.

Detailed description of the invention

I. Active substance of fabric softener

This invention relates to active substances of preparations for softening fabrics and preparations containing these active substances as main components in a concentration of 2 to 80 wt.%, preferably 13 to 75 wt.%, more preferably 15 to 70 wt.%, and even more preferably with 19 to 65 wt.%, based on the total weight of the preparation, whereby the mentioned active substances of fabric softening preparations are selected from the following substances and their mixtures.

(A) Quaternary ammonium diester (DEQA) fabric softener active ingredients

1) The first type of DEQA is preferably an active substance of the general formula:

(R) _4Hn -N( ⁺ ).KCH2)nYR ¹ ]m (1) where R is hydrogen or lower alkyl or hydroxyalkyl C-^-Cg, preferably C^-Cj, for example methyl (most preferred), ethyl, propyl, hydroxyethyl, etc., also benzyl, or their mixtures, m is 2 or 3, n is up to 4, preferably 2, Y is -O-(O)C-, -(R)N-(O) C-, -C(O)-N(R)- or -C(O)-O-, preferably -O-(O)C-, the total number of carbon atoms in each group R ¹ , plus one, ·- · 8 if Y is -0-{0)C- or -(R)N-(O)C-, is 6 to 22, preferably 12 to 22, more preferably 14 to 20, but at most one group R ¹ or YR ¹ contains less than 12 carbons and the additional group R ¹ or YR-^ contains at least 16 carbon atoms, each R ¹ group being a long branched alkyl and unsaturated alkyl (including alkyls with multiple double bonds) C5-C21 (or Cg- C22)/ ^preferably Cg-C ₁₉ (or Cg-C ₂₀ ), most preferably C ₁₁ -C ₁₇ or ( ^c i2 ^c 18 ^ ' Ρ ^οτη θ ^Γ of branched alkyls to unsaturated alkyls is 5:95 to 95:5, with preferably 75:25 to 25:75, more preferably 50:50 to 30:70, particularly preferably 35:65, and for unsaturated alkyl groups, the iodine value of the fatty acid corresponding to the respective group R ¹ is preferably 20

130 and most preferably 70 to 115, and where the anion compatible with the fabric active substance, preferably, chloride, bromide, sulfate, and/or nitrate, more preferably up to 140, more preferably 50 up to the counterion, X, of the fabric softener can be methyl sulfate, ethyl sulfate, chloride;

2. preparation for softening fabrics of the general formula:

where Y, R,

RN( ⁺ )CH2Cbf (-)

-YR1

CH ₂ yr1 '(-) (2) have the same meaning as before (These substances are substances of the general formula:

[CH ₃ ] ₃ N ⁺ (CH ₂ CH(CH ₂ O(O)CR ¹ O(O)CR ¹ )Cl, η

where -O-(O)CR are partially unsaturated acid residues, for example oleic acid, R is preferably methyl or ethyl, R ¹ is alkyl C-^ to C-^gs by varying degrees of branching and substitution of the alkyl chain, and partially an acid residue with a branched chain such as isostearic acid); and

3. mixtures of these substances.

The counterion X can be any anion compatible with the active ingredient of the fabric softener, preferably an anion of a strong acid, for example chloride, bromide, methyl sulfate, • · ·· · » 9 9 <

» 9 99

9 9 4 • · 4 ·· ·· ethyl suifate, sulfate, nitrate and the like, more preferably chloride. This anion can also be an anion with two charges. However, this case is less preferred and X" in this case represents half of the respective group. The active component of the preparation for fabric softening can be a mixture of substances containing substances with branched and unsaturated chains. Preferred biodegradable active substances of the fabric softener based on ammonium salts suitable for the preparation of such mixtures may contain the group -O-(O)CR ¹ derived from an unsaturated or polyunsaturated fatty acid, for example from oleic acid and/or from a partially hydrogenated fatty acid, from vegetable oil and/or partially hydrogenated vegetable oil, such as canola oil, safflower oil, groundnut oil, sunflower oil, corn oil, soybean oil, beef tallow, rice bran oil, etc. Mixtures of unsaturated fatty acids and mixtures of different DEQAs derived from different unsaturated fatty acids can be used and are preferred. Examples of DEQA substances prepared from preferred unsaturated fatty acids are listed below under the designations DEQA ¹ and DEQA ⁸ .

DEQA ⁶ is made from peanut fatty acids, DEQA ⁷ is made from slightly hydrogenated beef tallow fatty acids, and DEQA ⁸ is made from slightly hydrogenated canola oil fatty acids.

DEQA substances containing R ¹ groups with branched chains, originating for example from isostearic acid, contain at least partly other R ¹ substituents. The active substances of fabric softening preparations are preferably made up of compounds containing a mixture of branched chains

^R1 . Compounds and unsaturated groups with branched chains usually form with the groups 5 to 95%, preferably up to 75%, more preferably 35 to 50% of the active substance.

Suitable branched chain fatty acids that can be used to prepare DEQA with branched chains, or with a mixture of branched alkyls and unsaturated alkyls, can be prepared by various methods. The corresponding branched-chain fatty alcohols can be prepared by reduction of branched-chain fatty acids, carried out by common reactions, ► <

• -••ίο

00 00 ·0 0 0« 0 0 0 0 · 0 0 00

0000000 0 0 0 0 0 000000 00 00 for example using a borane-THF mixture as described in Brown, J. Amer. Chem. Soc. (1970), 92, 1637, which is incorporated herein by reference. Examples of branched chain fatty acids are given below.

Branched-chain fatty acid 1: 2-n-heptylundecanoic acid θ

2-n-Heptylundecanoic acid [22890-21-7] is manufactured by TCI America under catalog number 10281. It can be prepared by oxidation of Guerbet's alcohol, 2-heptylundecanol, which is obtained by aldol condensation of nonanal. Guerbet's alcohols can be purchased from Condea under the trademark ISOFOL ^R alcohols.

Branched-chain fatty acid 2: 2-n-hexyldecanoic acid o

2-n-heptylundecanoic acid [25354-97-6] is manufactured by TCI America under catalog number H0507. It can be prepared by oxidation of Guerbet's alcohol 2-hexyldecanol, which is obtained by aldol condensation of octanal.

Branched-chain fatty acid 3: 2-n-butyloctanoic acid o

2-n-Butyloctanoic acid is manufactured by Union Carbide under the trademark ISOCARB ^R 12 Acid. It can be prepared by oxidation of Guerbet's alcohol with 2-butyloctanol.

4-branched chain fatty acid: 5,7,9-trimethylnonanoic acid

• AA And · · AA AA AND • AA • A A A A * A A A And A • And A A A A AND A A A And A AND AND AND • A A A A • A A A A A A And A And A

- 11 p.m

5,7,9-Trimethylnonanoic acid and 3,5,7,9-tetramethylnonanoic acid are produced by Union Camp Corporation using the oxo process described in Ν. E. Lawson et al. in J. Am. Oil. Chem. Soc. 1981, 58, 59.

Branched chain fatty acid 5: -alkyl derivatives of carboxylic acids

RR'CHCO ₂ H

-substituted acids can be prepared by C-alkylation of an enamine synthesized from a straight-chain aldehyde such as octanal or decanal. The resulting enamine forms a carbon carbanion in position relative to the terminal nitrogen. The reaction of an enamine anion with an alkyl bromide in the presence of a catalytic amount of Nal yields a branched-chain enamine, the hydrolysis of which produces an -alkylated aldehyde. This aldehyde can then be oxidized to the corresponding carboxylic acid.

-heptyldecanoic acid

The decanal (aldehyde) can be reacted with an excess of a cyclic amine such as pyrrolidine by heating under reflux in toluene in the presence of a trace amount of p-toluenesulfonic acid. Condensation of an amine with an aldehyde produces water, which can be removed by condensation in a freezer. After removal of the theoretical amount of water, heptyl bromide and sodium iodide can be added and the alkylation can be completed in the same solvent system. After overnight alkylation, the reaction mixture is poured onto ice and acidified with 20% HCl. This hydrolysis converts the alkylated enamine to -heptyldecanal. This product can be isolated by washing and drying the solvent layer and then removing the solvent by distillation under reduced pressure.

The isolated branched aldehyde can then be converted to the desired carboxylic acid by oxidation in a suitable solvent system. Examples of oxidizing agents are aqueous potassium permanganate, Jones reagent (CrC^/í^SC^/H^O) in acetone, • ·♦··

Β · Β Β *- *12 ·· ΒΒ • · « Β

Β · Β Β

Β Β Β Β *

Β Β Β • Β Β Β

Cr0 ₃ -acetic acid and j. The separation of the desired -heptyldecanoic acid from the oxidation medium is supported by the high molecular weight of the acid.

Branched-chain fatty acid 6: 9- and 10-Alkoxyoctadecanoic acid and other isomers and corresponding alkoxyoctadecanols.

9- and 10-methoxyoctadecanoic acids

The method of Siouffi et al., described in Chemistry and Physics of Lipids, 8.(2), 91-101 (1972), is used. 5 g of methyl oleate is dissolved in 8 g of methanol and reacted with tert-butyl bromide to form a mixture of methoxy bromide derivatives. These are isolated and debrominated using a Rany catalyst, and the crude acid thus obtained is isolated by acidification. Hydrogenation of the olefinic components contained in this crude acid is carried out in cyclohexane using platinum oxide. This creates a mixture of the desired 9- and 10-methoxyoctadecanoic acids.

9- and 10-isopropoxyoctadecanoic acids

The same procedure is followed except that 2-propanol is replaced by methanol during the bromination. This resulted in the desired 9 and 10-isopropoxyoctadecanoic acids.

Isomers of Alkoxyoctadecanoic Acids

The same procedure is followed except that the oleic acid is first isomerized to a mixture of unsaturated acids by heating with methanesulfonic acid. Alkoxybromination and subsequent reduction lead in this case to a mixture of other isomers of alkoxyoctadecanoic acid.

The corresponding fatty alcohols

Substituted octadecanoic acids are reduced to the corresponding octadecanols using a borane-THF mixture according to the method described in Brown, J. Amer. Chem. Soc. 92, 1637 (1970).

Branched-chain fatty acid 7: Phenyloctadecanoic acid, alkylphenyloctadecanoic acid and related octadecanols.

Phenyloctadecanoic acid.

The method by Nakano and Foglia was used, described in The • fl flflfl fl fl • fl fl · • fl • flfl « · ’13 flfl flfl • flfl fl • · flfl • flflfl fl · • · · • fl flfl

Journal of the American Oil Chemists Society, 61(3), 569-73 (1984). To 5 g of oleic acid and 6.91 g of benzene, 10.2 g of methanesulfonic acid was added dropwise at 50 °C, and this mixture was then allowed to stir for 6 hours. The reaction mixture was poured into water and extracted with diethyl ether. After removal of the solvent by stripping under reduced pressure, a crude mixture of isomers of phenyoctadecanoic acid was obtained. Methylphenyloctadecanoic acid.

Using benzene instead of toluene, a mixture of isomers of methylphenyoctadecanoic acid was obtained by the same synthetic procedure.

The respective octadecanols. Substituted octadecanoic acids were reduced to the corresponding octadecanols using a borane-THF mixture by the method described in Brovn, J. Amer. Chem. Soc. 92, 1637 (1970).

Branched chain fatty acid 8: Phenoxyoctadecanoic acid, hydroxyphenyloctadecanoic acid and corresponding octadecanols

Hydroxyphenyloctadecanoic acids.

The method described in Nakano, Foglia, The Journal of the American Oil Chemists Society, £1(3) was used. 569-73 (1984). A mixture of oleic acid, phenol and methanesulfonic acid in a ratio of 1:5:6 was left to react at 22°C for 48 hours. The reaction mixture was poured into water and extracted with ether. The solvent and phenol were removed from the extract by stripping to form the desired mixture of crude isomers of hydroxyphenyoctadecanoic acid. Phenoxyoctadecanoic acids.

The described reaction was repeated with a 1:5:2 molar ratio of oleic acid, phenol and methanesulfonic acid. The isolated crude product is predominantly phenoxyoctadecanoic acid, but also contains hydroxyphenyoctadecanoic acid. Chromatographically, a purified mixture of phenoxyoctadecanoic acid isomers was obtained. The respective octadecanols.

Substituted octadecanoic acids are reduced to the corresponding octadecanols using a borane-THF mixture by the method of J. Brown, Amer. Chem. Soc., 92, 1637 (1970).

Branched chain fatty acid 9: Isostear fe • fefefefe • fe • · • fe • · ' • fe fefe • « · · • · fefe • ··· t · • · · ·· fefe acids.

Isostears obtained by the acid process are obtained from monomeric acids, the dimerization of unsaturated fatty acids C _1g of US Patent No. 2,812,342, issued November 5, 1957, to RM Peters, which is incorporated herein by reference.

Suitable branched chain fabric softener actives which can be mixed with the above described unsaturated fabric softener actives (DEQA) to form the fabric softener actives of the present invention can be synthesized using the above described fatty of branched chain acids and/or corresponding branched chain fatty alcohols. Similarly, branched chain fatty acids and/or corresponding alcohols can be used in combination with unsaturated fatty acids and/or alcohols to form suitable mixed chains of the active substance. Examples of DEQAs containing branched chains, described below as DEQAs ¹⁰ to DEQAs ²⁵ , may be mixed with unsaturated DEQAs. DEQA ¹⁰ through DEQA ¹² are prepared from various commercially available isostearic acids.

As mentioned earlier, other preferred DEQAs are those which are prepared as certain DEQAs from mixtures of various branched and unsaturated fatty acids (full fatty acid mixtures), rather than by mixing individual DEQAs prepared from different fractions of a full fatty acid mixture.

It is advantageous if a substantial part of the fatty acyl groups are unsaturated groups, for example if this part is 25% to 70%, preferably 50% to 65%. Polyunsaturated fatty acyls may be used. The total concentration of the active substance containing polyunsaturated fatty acyl groups (total level of active containing polyunsaturated fatty acid groups - TPU) can be 3% to 30%, preferably 5% to 25%, more preferably 10% to 18%. Both cis and trans isomers can be used, preferably with a cis/trans ratio of 1:1 to 50:1, the minimum value of this ratio being 1:1, preferably at least 3:1 and more preferably 4:1 to 20:1. (The value of the active substance content of the preparation for fabric softening, with a certain group R ¹ , used in this document is the same as ··

9

99 99 99

9 9 9 9 9 9

9 9 9 99 • · ♦ ···· · 9 9 9 9 9

999 9999 99 99

Ί 1 value of the content of a certain group R- ¹ - to the total content of R groups occurring in all active substances of the preparation for fabric softening.) Unsaturated and polyunsaturated fatty acyl groups, mentioned in the previous and following text, have a surprisingly significant softening effect, they contain- l branched chain, and also have good rewetting ability, good antistatic properties, and especially good regeneration properties after solidification and melting.

Materials containing mixtures of branched and unsaturated chains can be prepared more easily than conventional active ingredients of fabric softening preparations containing only saturated chains. They can be used to prepare concentrated starting mixtures, which have a low viscosity and which are therefore easier to work with, for example pumping, mixing, etc. Of these materials, containing only a small amount of solvent, which is usually contained in them in an amount of e.g. 5 to 20 wt.%, preferably 8 to 25 wt.%, more preferably 10 to 20 wt.%, based on the total weight of the mixture, a plasticizer /solvent mixture, it is also easier to prepare concentrated stable preparations according to the present invention, even at temperatures close to ambient temperature. The ability to process these active substances at low temperatures is especially important if they contain polyunsaturated groups, as it minimizes their degradation. Further protection against degradation can be achieved by the presence of effective anti-oxidants, complexing and reducing agents in these fabrics and fabric softening preparations as discussed below. The use of branched chain fatty acyls increases degradation resistance while maintaining fluidity and improving softening capabilities.

Preparations according to the present invention may also contain some biodegradable substances DEQA, used for fabric softening, based on quaternary ammonium salts, the general formula (1) mentioned above and/or the formula (2) mentioned below, where:

Y is -O-(O)C- or -C(O)-O-, preferably -O-(O)C-; m is 2 or 3, preferably 2; n is 1 to 4, preferably 2;

·· • · ·· • « • · ·- *16 • ·· ·· ·· 99 9 9 9 9 9 9

9 9 9 99

9 9 999 9 9

9 9 9 9

999 9999 99 99

R is C 1 -C 8 alkyl, preferably methyl, ethyl, propyl, benzyl or a mixture of these groups, more preferably C 1 -C 1 alkyl;

R or YR ¹ , is a hydrophobic saturated group Cg-C ₁₄ , preferably ^c 12 ^_c 14 containing a hydrocarbon or substituted hydrocarbon residue (IV is preferably 10 or less, more preferably less than 5, the total number of carbons in the acyl group R ¹ + 1 in the case where Y is -O-(O)C- or -(R)N-(O)C- and the proton is X", it is the same as above. X ^- is preferably not a phosphate ion.

The saturated acyl groups ^C 8 ^-C 14 may be of one type or may be a mixture of these groups.

A suitable source of fatty acids from which these fatty acyls are derived are the acids contained in coconut oil, lauric, caprylic and capric acids.

In the hydrocarbon groups Ci2~ ^c 14 ( ^ne ^° ^c n ^_c i3^< 3 ^{SOU are} preferably saturated, IV is for example preferably lower than 10, more preferably lower than 5.

The branched substituents R-^ can contain various groups such as branched alkoxy groups and also a small amount of these 1 unbranched groups, the only condition being that these R groups retain their hydrophobic character. Biodegradable diester derivatives of solidified dialkyldimethylammonium chlorides with alkyls derived from beef tallow fatty acids (referred to here under the abbreviation DTDMAC - ditallow dimethyl ammonium chloride) can be considered preferred substances, which are widespread active substances of fabric softening preparations.

When used according to the methods described in this invention, these diesters may also contain certain amounts of the corresponding monoesters. Preferably, at least 80% DEQA is a diester, which may contain 0 to 20% DEQA monoesters, where, for example, one YR ¹ group is either -OH or -C(O)OH, and in the case of a substance of the general formula (1 ), m is 2. The corresponding diamide and/or mixed esteramide can also be a substance with one long-chain hydrophobic group, for example one YR ¹ group is either -N(R)H or -C(O)OH. In the following text, any information, for example information regarding the monoesters of the active substance, also applies to the monoamide of the active substance. For softening carried out under conditions, • 9 .9 9 9 '-•17

99 99 99

9 9 9 9 9 9

9 9 9 9 9

9 9 999 9 9

9 9 9 9

999 9999 99 99 when there is either no transfer of detergent, or its transfer is to be minimal, the monoester concentration needs to be as low as possible, preferably below 5%. However, under conditions where there is high transfer of anionic surfactant or detergent, a certain concentration of monoester may be advantageous. The total ratio of diester to monoester is 100:1 to 2:1, preferably 50:1 to 5:1, more preferably 13:1 to 8:1. If there is a high transfer of detergent, the ratio of diester to monoester is preferably 11:1. The monoester content can be controlled in the preparation of DEQA.

The substances described above, which will be further specified, used as biodegradable active substances of preparations for softening fabrics based on quaternary esteramines, can be prepared according to the procedures that are the subject of this invention by conventional synthetic procedures. In one synthetic procedure that prepares the diester types of DTDMAC, an amine of the formula RN((CH ₂ CH ₂ OH) ₂ is esterified on both hydroxyl groups with an acid chloride of the formula R ¹ C(O)C1 to form an amine that can be converted to the cationic form by acidification (one R group is Η) to form one type of plasticizer, or subsequently quaternized with an alkyl halide RX to form the desired reaction product (where R and R ¹ are the groups previously defined).Those skilled in the art of chemistry will appreciate that the above series of reactions enables the preparation of a wide selection of substances.

Another substance of the DEQA type, which is suitable for the preparation of active substances of fabric softening preparations and for the preparation of clear fabric softening preparations according to the present invention, has the general formula (1) where one group R is a hydroxyalkyl group ^-ΰ ₄ , preferably such a substance in which the R group is a hydroxyethyl group.

The second type of DEQA active substances has the general formula:

RN( ⁺ )CH 2 CH ³ CH ₂ Yr1

X<’>

(2) where Y, R, R ¹ , and have the same meaning as before, the substances are, among others, substances of the general formula:

By these • φφφφ • φφ ·· · · · • φφ φ φ φ φ φφφ

Φ φ φ φ φ φφφ φ φφφ φ φ φ φ φ φ φφ [CH ₃ ] ₃ Ν ⁺ (CH ₂ CH (CH ₂ O (Ο) CR ¹ O (Ο) CR ¹ ) Cl η

where R is preferably methyl or ethyl, R is C ₁₃ to C 8 alkyl with varying degrees of substitution of alkyl chains or unsaturated chains. Anion X is the same as in DEQA (1) above. A diester may have a monoester present therein. The amount of monoester that may be present is the same as in DEQA (1). An example of a preferred DEQA type agent (2) is the propyl ester active ingredient of quaternary ammonium salt-based fabric softeners, which is 1,2-di(acetoxy)-3-trimethylammoniumpropane chloride with the same acyl groups as the acyl groups in DEQA ^5, whose the following example is DEQA ⁹ .

These types of active agents and general methods of their preparation are described in US Patent No. 4,137,180 to Naik et al., issued January 30, 1979, which is incorporated herein by reference.

In suitable active substances of the fabric softening preparations (1) and (2), R ¹ is branched alkyl, monounsaturated alkenyl, or polyunsaturated alkenyl, and these active substances contain mixtures of branched and unsaturated alkyl groups R ¹ , especially within individual molecules, in the previously mentioned conditions. Substances of the type are the subject of this invention, contain low fatty acids, from unreacted starting material,

DEQA and/or as a by-product of the partial degradation (hydrolysis) of the active substance of the fabric grounding product in the manufactured product. It is suitable for the free acid concentration to be low, preferably lower than 10% by weight, more preferably 5% by weight. active ingredients of fabric softener.

DEQA which concentration which can come from used for preparation

II. Preferred major solvent systems that may or may not be used

The preparations according to the present invention preferably contain less than 40 wt.%, more preferably 10 to 35 wt.%, even more preferably 12 to ·· • 4· « ·· ·· ··· · 4 · · · · ·· · • 4· · · · · 4· • 4 · 4 · «4 ···♦ · • · a*n · · · · ♦ wt.% and most preferably 14 to 20 wt.% of the main solvent, based on the total weight of the preparation. The mentioned main solvent is chosen so that the odor of the product is as low as possible and that the final product has a low viscosity. For example, isopropyl alcohol is not very effective and has a strong smell. n-Propyl alcohol is more effective, but has a strong odor. Various butyl alcohols are also odorous, but may be used because they provide clarity and stability, especially when used as components of the main solvent system, thereby minimizing their odor. These alcohols are also selected for optimum stability at low temperatures, i.e. for their ability to form formulations which are liquid, have acceptably low viscosities and are transparent, preferably clear, at temperatures below 4.4°C, and are able to regain their properties when stored at temperatures below 6.7°C.

As far as possible, the concentration of the main solvents is kept at the lowest possible level necessary for the compositions of the present invention to be translucent or clear. The presence of water has a significant effect on the amount of main solvent required to achieve the clarity of these products. The higher the water content, the higher the concentration of the main solvent (relative to the concentration of the plasticizer) required to achieve the clarity of the product. On the contrary, the lower the water content, the lower the concentration of the main solvent (relative to the concentration of the active substance of the fabric softener) is needed. At low water concentrations ranging from 5 to 15% by weight, the ratio of the active substance of the fabric softener to the main solvent is preferably 55:45 to 85:15, more preferably 60:40 to 80:20. At water concentrations in the range of 15% to 70%, the weight ratio of the fabric softening agent to the main solvent is preferably 45:55 to 70:30, more preferably 55:45 to 70:30. At high water concentrations of 70 to 80%, the ratio of fabric softener active substance to main solvent is preferably 30:70 to 55:45, more preferably 35:65 to 45:55.

At even higher concentrations of water, the ratio of the active substance of the fabric softener to the main solvent is even higher.

The suitability of the main solvent for the preparation of the liquid, concentrated, preferably clear preparation for fabric softening according to the invention, which is characterized by the required stability, is surprisingly quite selective. Suitable solvents may be solvents selected based on their octanol/water partition coefficient (P). The octanol/water partition coefficient of the main solvent is the ratio between its equilibrium concentrations in octanol and in water. The partition coefficients of the components of the main solvent according to the present invention are preferably given in the form of their decimal logarithms logP. The logPs of many components are known, for example the Pomona92 database, which can be obtained from Daylight Chemical Information Systems, ln. (Daylight CIS), lrvine, Califonia, contains many of these data, along with citations of the original literature. However, logP values can be most conveniently calculated using the CLOGP program, which can also be obtained from Daylight CIS. This program also includes the experimental logP values contained in the Pomona92 database. Calculated ClogP, (i.e. calculated logP - ClogP) is determined based on the fragment method of Hansch and Leo (see A. Leo, in Comprehensive Medicinal Chemistry, vol. 4, editors C. Hansch, P. G. Sammens, J. B. Taylor and C. A. Ramsden, p. 295, Pergamon Press, 1990, incorporated herein by reference). The fragment method is based on the chemical structure of each of the components, and takes into account the numbers and types of atoms, their mutual connections and chemical bonds. These ClogP values, which are the most reliable, and whose use for this petrochemical property is preferably used instead of logP in the selection of the main components suitable for the processes of the present invention. Other methods that can be used to calculate ClogP are, for example, the Crippens fragmentation method described in J. Chem. Inf. Comput. Sci., 27, 21 (1987), Viswanadhan's fragmentation method, described in J. Chem. Inf. Comput. Sci., 29, 163 (1989) and Brot's method, described in Eur. J. Med. Chem. - Chem. Theor., 19., 71 (1984). The principal solvents suitable for use in accordance with the present invention are those which have the most widespread experimental solvent values which are • ft •SI • · • ••ft • •ft · ft • · · ·· ··

ClogP 0.16 to 0.64, preferably 0.25 to 0.62 and more preferably 0.40 to 0.60, wherein the molecules of said main solvent preferably have a somewhat asymmetric structure and a melting or freezing point such that the solvent is liquid at room temperature or at temperatures not significantly different from room temperature. Solvents that are low molecular weight and biodegradable are preferred for some purposes. Solvents that have a more asymmetric molecular structure seem to be very suitable, while solvents with a symmetrical structure such as 1,7-heptanediol or

1,4-bis(hydroxymethyl)cyclohexane, which have a center of symmetry, it is apparently not possible to obtain clear preparations if they are used alone, even if their ClogP values are favorable.

The most suitable main solvents can be recognized by the presence of small plasticizer particles which can be observed in preparations diluted to the concentration used in rinsing by electron microscopy at low temperatures. These diluted formulations appear to produce softener dispersions that have a more distinctly unilamellar appearance than conventional fabric softener formulations. It seems that the more unilamellar the appearance, the better the quality of these preparations. These preparations are characterized by surprisingly good softening properties compared to similar preparations prepared in the usual way with the same active substance. A characteristic feature of the preparations according to the invention is also an improved ability to apply perfume compared to conventional fabric softening preparations, especially if the perfume is added to the preparation at room temperature or at a temperature close to room temperature. Suitable main solvents are listed below in several tables, in which, for example, aliphatic and/or alicyclic diols with a certain number of carbon atoms, alcohols, glycerol derivatives, diol alkoxylates and mixtures of these substances are listed separately. The numbers given for individual compounds in the tables are the registration numbers used in the journal Chemical Abstracts (CAS No.). These numbers are given for each of these substances for which this number

9t ·

·· • · * •-•»€*2 • ·· ·· ··

9 9 9 9 9 9

9 9 9 99

9 9 999 9 9

9 9 9 9 »· 9999 99 99 exists. For new substances, the method of their preparation is described below. Also listed for comparison are some solvents which are unsuitable as main solvents, but which can be used in admixture with suitable main solvents. Suitable primary solvents can be used to prepare concentrated fabric softening formulations which are advantageous in terms of the stability and clarity requirements set forth herein.

A number of diol main solvents having the same general chemical formula may exist in the form of a number of stereoisomers and/or optical isomers. Each of these isomers is normally identified by its own registration number (CAS No.). For example, the isomers of 4-methyl-2,3-hexanediol are marked with the following registration numbers: 146452-51-9, 146452-50-8, 146452-49-5, 146452-48-4, 123807-34-1, 123807- 33-0, 123807-32-9 and 123807-31-8.

In the following tables, for simplicity, only one registration number is given for each chemical formula.

This method of presentation is only used to provide typical examples, which are sufficient to clarify the invention, and the subject of the invention is not limited by it in any way. This means that other isomers with different registration numbers and mixtures thereof are also included in this invention. Similarly, in those cases where substances containing different isotopes such as deuterium, tritium, carbon-13, etc. are included under one registration number, it is understood that the subject of this invention also includes substances containing a natural mixture of isotopes, and vice versa.

• ·

Table 1

Alcohols

compound name compound registration number in a magazine Chemical Abstracts (CAS No.) n-propanol 71-23-8 2-Butanol 15892-23-6 2-methyl-2-propanol 75-65-0 inappropriate isomer 2-methyl-1-propanol 78-83-1

Table 2

Diols C6 name of the compound registration number of the compound in the journal Chemical Abstracts (CAS No.) suitable also from omer

2,3-dimethyl-2,3-butanediol 76-09-5 preferred isomers

1,3-dimethyl-2-butanediol

3.3-dimethyl-1,2-butanediol

2-methyl-2,3-pentanediol

3-methyl-1,3-pentanediol 3-methyl-2,3-pentanediol

1.3-Hexanediol

3.4-Hexanediol

66553-15-9

59562-82-2

7795-80-4

521-37-9

7795-79-1

617-30-1

922-17-8 most preferred isomers 2-ethyl-1,2-butanediol

2-methyl-1,2-pentanediol

3-methyl-1,2-pentanediol

66553-16-0

20667-05-4

159623-53-7

Table 2 - continued compound name Chemical Abstracts compound registration number (CAS No.) most preferred isomers

4-methyl-1,2-pentanediol 1721 10-08-8

1.2- hexanediol 6920-22-5 unsuitable isomers

2-ethyl-2-methyl-1,3-propanediol

2-isopropyl-1,3-propanediol

2-propyl-1,3-propanediol

2.2-dimethyl-1,3-butanediol

2.3-dimethyl-1,3-butanediol

2-ethyl-1,3-butanediol

2.2-dimethyl-1,4-butanediol

2.3-dimethyl-1,4-butanediol

2-ethyl-1,4-butanediol

2-methyl-1,3-pentanediol

3-methyl-1,3-pentanediol

4-methyl-1,3-pentanediol

2-methyl-1,4-pentanediol

3-methyl-1,4-pentanediol

4-methyl-1,4-pentanediol

2-methyl-1,5-pentanediol

3-methyl-1,5-pentanediol

2-methyl-2,4-pentanediol

3-methyl-2,4-pentanediol

1.3-Hexanediol

1.4-Hexanediol

1.5-Hexanediol

1.6-Hexanediol

2.4-Hexanediol

2.5- hexanediol • · • · ·· · · 1 • · 4 ·· ··

Table 3

C7 diols

compound name the registration number of the compound in the journal Chemical Abstracts (CAS No.) suitable isomers 2-butyl-1,3-propanediol 2612-26-2 2,2-diethyl-1,3-propanediol 115-76-4 2-(1-methylpropyl)-1,3-propanediol 33673-01-7 2-(2-methylpropyl)-1,3-propanediol 26462-20-8 2-methyl-2-propyl-1,3-propanediol 78-26-2 2,3,3-trimethyl-1,2-butanediol method B 2-ethyl-2-methyl-1,4-butanediol 76651-98-4 2-ethyl-3-methyl-1,4-butanediol 66225-34-1 2-propyl-1,4-butanediol 62946-68-3 2-isopropyl-1,4-butanediol 39497-66-0 2,2-dimethyl-1,5-pentanediol 3121-82-2 2,3-dimethyl-1,5-pentanediol 81554-20-3 2,4-dimethyl-1,5-pentanediol 2121-69-9 3,3-dimethyl-1,5-pentanediol 53120-74-4 2,3-dimethyl-2,3-pentanediol 6931-70-0 2,4-dimethyl-2,3-pentanediol 66225-53-4 3,4-dimethyl-2,3-pentanediol 37164-04-8 4,4-dimethyl-2,3-pentanediol 89851-45-6 2,3-dimethyl-3,4-pentanediol method B 2-ethyl-1,5-pentanediol 14189-13-0 2-methyl-1,6-hexanediol 25258-92-8 3-methyl-1,6-hexanediol 4089-71-8 2-methyl-2,3-hexanediol 59215-55-3 3-methyl-2,3-hexanediol 139093-40-6 4-methyl-2,3-hexanediol * Ά* ★ 5-methyl-2,3-hexanediol method B 2-methyl-3,4-hexanediol method B 3-methyl-3,4-hexanediol 18938-47-1 1,3-Heptanediol 23433-04-7

Table 3 - continued • · » « ·· φφ ·· ·· • φφφφ ♦ φφφ* • φ φφφφ · φ · · φ

ΦΦΦ Φ Ο φ» compound name compound registration number in the journal Chemical Abstract (CAS No.) suitable isomers

1.4-heptanediol

1.5-heptanediol

1.6-heptanediol

40646-07-9

60096-09-5

13175-27-4 preferred isomers

2-butyl-1,3-propanediol

2-propyl-1,4-butanediol

2-ethyl-1,5-pentanediol

2.3-dimethyl-2,3 pentanediol

2.4-dimethyl-2,3-pentanediol

3.4-dimethyl-2,3 pentanediol

4.4-dimethyl-2,3-pentanediol

2.3-dimethyl-3,4-pentanediol

2-methyl-1,6-hexanediol

3-methyl-1,6-hexanediol

1.3-heptanediol

1.4-heptanediol

1.5-heptanediol

1.6-heptanediol more preferred isomers

2.3-dimethyl-2,3-pentanediol

2.4-dimethyl-2,3-pentanediol

3.4-dimethyl-2,3-pentanediol

4.4-dimethyl-2,3-pentanediol

2.3-dimethyl-3,4-pentanediol inappropriate isomers

2-methyl-2-isopropyl-1,3-propanediol 2-ethyl-3-methyl-1,2-butanediol

2.2.3- trimethyl-1,3-butanediol 2-ethyl-2-methyl-1,3-butanediol

2612-26-2

62946-68-3

14189-13-0

6931-70-0

66225-53-4

3716-1-0-8

89851-45-6 method B

25258-92-8

4089-71-8

23433-04-7

40646-07-9

60096-09-5

13175-27-4

6931-70-0 66225-53-4 37164-04-8 89851-45-6 method B

Table 3 - continued compound name compound registration number in the journal Chemical Abstract (CAS No.) inappropriate isomers

2-ethyl-3-methyl-1,3-butanediol 2-isopropyl-1,3-butanediol

2-propyl-1,3-butanediol

2.2.3-trimethyll,4-butanediol

3-Ethyl-1-methyl-1,4-butanediol

2.3-dimethyl-1,2-pentanediol

2.4-dimethyl-1,2-pentanediol

3.3-dimethyl-1,2-pentanediol

3.4-dimethyl-1,2-pentanediol

4.4-dimethyl-1,2-pentanediol 2-ethyl-1,2-pentanediol

2.2-dimethyl-1,3-pentanediol

2.3-dimethyl-1,3-pentanediol

2.4-dimethyl-1,3-pentanediol 2-ethyl-1,3-pentanediol

3.4-dimethyl-1,3-pentanediol

4.4-dimethyl-1,3-pentanediol

2.2-dimethyl-1,4-pentanediol

2.3-dimethyl-1,4-pentanediol

2.4-dimethyl-1,4-pentanediol

3.3-dimethyl-1,4-pentanediol

3.4-dimethyl-1,4-pentanediol

2.3-dimethyl-2,4-pentanediol

2.4-dimethyl-2,4-pentanediol

3,3-dimethyl-2,4-pentanediol

2-methyl-1,2-hexanediol

3-methyl-1,2-hexanediol

4- Methyl-1,2-hexanediol

5-methyl-1,2-hexanediol

2-methyl-1,3-hexanediol

3-methyl-1,3-hexanediol

4-methyl-1,3-hexanediol

it · » · » · • it it

• ·

Table 3 - continued compound name Chemical Abstracts registration number of the compound (CAS No.) inappropriate isomers

5-methyl-1,3-hexanediol

2-methyl-1,4-hexanediol

3-methyl-1,4-hexanediol

4-methyl-1,4-hexanediol

5-methyl-1,4-hexanediol

2-methyl-1,5-hexanediol

3-methyl-1,5-hexanediol

4-methyl-1,5-hexanediol

5-methyl-1,5-hexanediol

2-methyl-2,4-hexanediol

3-methyl-2,4-hexanediol

4-methyl-2,4-hexanediol

5-methyl-2,4-hexanediol

2-methyl-2,5-hexadiol

3-methyl-2,5-hexanediol

1.2-heptanediol

2.3-heptanediol

2.4-heptanediol

2.5-heptanediol

2.6-heptanediol

3.4-heptanediol

1.7-heptanediol

3.5-heptanediol *** 146452-51-9; 146452-50-8; 146452-49-5; 146452-48-4;

12387-34-1; 123807-33-0; 123807-32-9; 123807-31-8; and mixtures thereof

• · · ·

Table 4

Octanediol isomers

Propanediol derivatives compound name compound registration number in Chemical Abstracts journal (CAS No.) suitable isomers

2-(2-methylbutyl)-1,3-propanediol

2-(1,1-dimethylpropyl)-1,3-propanediol 2-(1,2-dimethylpropyl)-1,3-propanediol 2-(1-ethylpropyl)-1,3-propanediol 2-(1-methylbutyl) -1,3-propanediol 2-(2,2-dimethylpropyl)-1,3-propanediol 2-(3-methylbutyl)-1,3-propanediol 2-butyl-2-methyl-1,3-propanediol 2-ethyl -2-isopropyl-1,3-propanediol 2-ethyl-2-propyl-1,3-propanediol 2-methyl-2-(1-methylpropyl)-1,3-propanediol 2-methyl-2-(2-methylpropyl) )-1,3-propanediol 2-tert-butyl-2-methyl-1,3-propanediol more preferred isomers

-(1,1-dimethylpropyl)-1,3-propanediol 2-(1,2-dimethylpropyl)-1,3-propanediol 2-(1-ethylpropyl)-1,3-propanediol 2-(2,2-dimethylpropyl) )-1,3-propanediol 2-ethyl-2-isopropyl-1,3-propanediol 2-methyl-2-(1-methylpropyl)-1,3-propanediol 2-methyl-2-(2-methylpropyl)-1 ,3-propanediol 2-tertbutyl-2-methyl-1,3-propanediol unsuitable even from the omer

2-pentyl-1,3-propanediol

87194-40-9 method D method D

25462-28-6

22131-29-9 method D

25462-27-5

3121-83-3

24765-55-7

25450-88-8

813-60-5

25462-42-4

25462-45-7 method D method D 25462-28-6 method D 24765-55-7 813-60-5 25462-42-4 25462-45-7 • · · • · * · ·

Table 4 - continued, Butanediol derivatives compound name Chemical Abstracts compound registration number (CAS No.) suitable isomers

2.2-diethyl-1,3-butanediol

2-(1-methylpropyl)-1,3-butanediol 2-butyl-1,3-butanediol 2-ethyl-2,3-dimethyl-1,3-butanediol 2-(1,1-dimethylethyl)-1,3 -butanediol 2-(2-methylpropyl)-1,3-butanediol 2-methyl-2-isopropyl-1,3-butanediol

2-methyl-2-propyl-1,3-butanediol

3-methyl-2-isopropyl-1,3-butanediol 3-methyl-2-propyl-1,3-butanediol

2.2-diethyl-1,4-butanediol

2-methyl-2-propyl-1,4-butanediol 2-(1-methylpropyl)-1,4-butanediol 2-ethyl-2,3-dimethyl-1,4-butanediol 2-ethyl-3,3-dimethyl -1,4-butanediol 2-(1,1-dimethylethyl)-1,4-butanediol 2-(2-methylpropyl)-1,4-butanediol

2-methyl-3-propyl-1,4-butanediol

3-methyl-2-isopropyl-1,4-butanediol preferred isomers

2.2-diethyl-1,3-butanediol

2-(1-methylpropyl)-1,3-butanediol 2-butyl-1,3-butanediol 2-ethyl-2,3-dimethyl-1,3-butanediol 2-(1,1-dimethylethyl)-1,3 -butanediol 2-(2-methylpropyl)-1,3-butanediol 2-methyl-2-isopropyl-1,3-butanediol

2-methyl-2-propyl-1,3-butanediol

3-methyl-2-propyl-1,3-butanediol

2.2-diethyl-1,4-butanediol

99799-77-6 method C 83988-22-1 method D 67271-58-3 method C method C 9979g-79-g method C method D method H method H method H method F method F 36976-70-2 method F 90951 -76-1 99799-24-3

99799-77-6 method C 83988-22-1 method D 67271-58-3 method C method C 99799-79-8 method D method H

Table 4 - continued, Butanediol derivatives compound name Chemical Abstracts registration number of the compound (CAS No.) preferred isomers

2-ethyl-2,3-dimethyl-1,4-butanediol 2-ethyl-3,3-dimethyl-1,4-butanediol

2-(1,1-dimethylethyl)-1,4-butanediol

3-methyl-2-isopropyl-1,4-butanediol more preferred isomers

2-(1-methylpropyl)-1,3-butanediol 2-(2-methylpropyl)-1,3-butanediol 2-butyl-1,3-butanediol

2-methyl-2-propyl-1,3-butanediol

3-methyl-2-propyl-1,3-butanediol

2,2-diethyl-1,4-butanediol

2-ethyl-2,3-dimethyl-1,4-butanediol 2-ethyl-3,3-dimethyl-1,4-butanediol 2-(1,1-dimethylethyl 1,4-butanediol unsuitable isomers

2-butyl-1,4-butanediol

2-ethyl-3,3-dimethyl-1,2-butanediol

2-methyl-2-isopropyl-1,4-butanediol

3-methyl-2-isopropyl-1,2-butanediol

2,2,3,3-tetramethyl-1,4-butanediol method F method F 36976-70-2 99799-14-3 method C method C 83988-22-1 99799-79-8 method D method H method F method F 36976-70-2

Table 4 - continued, Isomers of trimethylpentanediol • · »· ·

99

9 9

9 9 name of the compound registration number of the compound in the journal Chemical Abstracts (CAS No.) suitable isomers

2.2.3-trimethyl-1,3-pentanediol

2.2.4-trimethyl-1,3-pentanediol

2.3.4-trimethyl-1,3-pentanediol

2.4.4-trimethyl-1,3-pentanediol

3.4.4-trimethyl-1,3-pentanediol

2.2.3-trimethyl 1,4-pentanediol

2.2.4-Timethyl-1,4-pentanediol

2.3.3-trimethyl-1,4-pentanediol

2.3.4-trimethyl-1,4-pentanediol

3.3.4-trimethyl-1,4-pentanediol

2.2.3-trimethyl-1,5-pentanediol

2.2.4-trimethyl-1,5-pentanediol

2.3.3-trimethyl-1,5-pentanediol

2.3.4-trimethyl-1,5-pentanediol

2,3,3-trimethyl-2,4-pentanediol

2.3.4-trimethyl-2,4-pentanediol

35512-54-0

144-19-4

116614-13-2

109387-36-2

81756-50-5 method H

80864-10-4 method H

92340-74-4

16466-35-6 method F

3465-14-3 method A

85373-83-7

24892-51-1

24892-52-2 preferred isomers

2.2.3-trimethyl-1,3-pentanediol

2.2.4-trimethyl-1,3-pentanediol

2.3.4-trimethyl-1,3-pentanediol

2.4.4-trimethyl-1,3-pentanediol

3.4.4-trimethyl-1,3-pentanediol

2.2.3-trimethyl-1,4-pentanediol

2.2.4-trimethyl-1,4-pentanediol

2.3.3-trimethyl-1,4-pentanediol

2.3.4-trimethyl-1,4-pentanediol

3.3.4-trimethyl-1,4-pentanediol

2.2.3-trimethyl-1,5-pentanediol

2.2.4-trimethyl-1,5 pentanediol

2,3,3-trimethyl-1,5-pentanediol

35512-54-0

144-19-4

116614-13-2

109387-36-2

81756-50-5 method H 80864-10-4 method F 92340-74-4 16466-35-6 method A 3465-14-3 method A • »

Table 4 - continued, Isomers of trimethylpentanediol compound name

9

9

999 9

9 9 9

9 9 9

9 99

99 9 9

9 9 registration number of the compound in the journal Chemical Abstracts (CAS No.) preferred isomers

2.3.4- trimethyl-2,4 pentanediol more preferred isomers

2.3.4- trimethbyl-1,3-peotanediol

2,3,4-trimethyl-1,4-pentanediol

2.2.3- trimethbyl-1,5-pentenediol

2.2.4-Trimethyl-1,5-pentoediol

2.3.3-trimethyl-1,5-pentanediol unsuitable even from omer

2.3.3-trimethyl-1,2-pentanediol

2.3.4-trimethyl-1,2-pentanediol

2.4.4-trimethyl-1,2-pentanediol

3.3.4-trimethyl-1,2-pentanediol

3.4.4-trimethyl-1,2-pentanediol

2.3.4-trimethyl-2,3-pentanediol

2.4.4-trimethyl-2,3-pentanediol

3.4.4-trimethyl-2,3-pentanediol

24892-52-2

116614-13-2 92340-74-4 method A 3465-14-3 method A

Ethylmethylpentanediol isomers compound name compound registration number in the journal Chemical Abstracts (CAS No.) also suitable for isomers

2-ethyl-2-methyl-1,3-pentanediol 2-ethyl-3-methyl-1,3-pentanediol

2-ethyl-4-methyl-1,3-pentanediol

3-ethyl-2-methyl-1,3-pentanediol 2-ethyl-2-methyl-1,4-pentanediol 2-ethyl-3-methyl-1,4-pentanediol method C method D 148904-97-6 55661- 05-7 method H method F • ·· flfl·· · fl flfl flfl flfl • flfl ♦ flfl flfl ·

Table 4 - continued, Isomers of ethylmethylpentanediol compound name • ···· »· · fl flfl · * flfl

I fl · · fl registration number of the compound in the journal Chemical Abstracts (CAS No.) suitable isomers

3-ethyl-4-methyl-1,4-pentanediol 3-ethyl-2-methyl-1,4-pentanediol, 3-ethyl-3-methyl-1,4-pentanediol 2-ethyl-2-methyl-1, 5-pentanediol 2-ethyl-3-methyl-1,5-pentanediol

2-ethyl-4-methyl-1,5-pentanediol

3-ethyl-3-methyl-1,5-pentanediol 3-ethyl-2-methyl-2,4-pentanediol more preferred isomers 2-ethyl-2-methyl-1,3-pentanediol 2-ethyl-3-methyl- 1,3-pentanediol

2-ethyl-4-methyl-1,3-pentanediol

3-ethyl-2-methyl-1,3-pentanediol 2-ethyl-2-methyl-1,4-pentanediol

2-ethyl-3-methyl-1,4-pentanediol

-ethyl-4-methyl-1,4-pentanediol

-ethyl-3-methyl-1,5-pentanediol

3-ethyl-2-methyl-2,4-pentanediol unsuitable isomers

2-ethyl-3-methyl-1,2-pentanediol

2-ethyl-4-methyl-1,2-pentanediol

3-ethyl-2-methyl-1,2-pentanediol 3-ethyl-3-methyl-1,2-pentanediol 3-ethyl-4-methyl-1,2-pentanediol 3-ethyl-4-methyl-1,3 -pentanediol 3-ethyl-4-methyl-i,4-pentanediol 3-ethyl-2-methyl-1,5-pentanediol 3-ethyl-2-methyl-2,3-pentanediol 3-ethyl-4-methyl-2 ,3-pentanediol method G method F method F method F 54886-83-8 method F 57740-12-2 method G method C method D 148904-97-6 55661-OS-7 method H method F method G 57740-12- 2 method G

Table 4 - continued, Ethylmethylpentanediol isomers • *9 ·· · · 9 • ·· • · · · . · * ·

9·9 ·· 9 • ····

9« ·« • 9 · · * · 99 • ·99 · 9 • · ·

compound name compound registration number in the journal Chemical Abstracts (CAS No.) unsuitable isomers 3-ethyl-3-methyl-2,4-pentanediol Isomers of propylpentanediol compound name compound registration number in the journal Chemical Abstracts (CAS No.) suitable isomers 2-isopropyl-1,3-pentanediol method D 2-propyl-1,3-pentanediol method C 2-isopropyl-1,4-pentanediol method H 2-propyl-1,4-pentanediol method H 3-isopropyl-1,4-pentanediol method H 2-isopropyl-1,5-pentanediol 90951-89-6 3-propyl-2,4-pentanediol method C more preferred isomers 1-isopropyl-1,3-pentanediol method D 2-propyl-1,3-pentanediol method C 2-isopropyl-1,4-pentanediol method H 2-propyl-1,4-pentanediol method H 3-isopropyl-1,4-pentanediol method H 3-propyl-2,4-pentanediol method C inappropriate even from ome ry 2-propyl-1,2-pentanediol 2-isopropyl-1,2-pentanediol 3-propyl-1,4-pentanediol 2-propyl-1,5-pentanediol 3-isopropyl-2,4-pentanediol

• φφ • φ · · · • φφ • φ · · • φ · φφφ φφ φ • φφφφ φφ φφ φ · φ · φ φφφ φ φφφφ φ φ φ · φ φ φ φ

Table 4 - continued, Dimethylhexanediol isomers

compound name the registration number of the compound in the journal Chemical Abstracts (CAS No.) suitable isomers 2,2-dimethyl-1,3-hexanediol 22006-96-8 2,3-dimethyl-1,3-hexanediol method D 2,4-dimethyl-1,3-hexanediol 78122-99-3 2,5-dimethyl-1,3-hexanediol method C 3,4-dimethyl-1,3-hexanediol method D 3,5-dimethyl-1,3-hexanediol method D 4,4-dimethyl-1,3-hexanediol method C 4,5-dimethyl-1,3-hexanediol method C 2,2-dimethyl-1,4-hexanediol method F 2,3-dimethyl-1,4-hexanediol method F 2,4-dimethyl-1,4-hexanediol method G 2,5-dimethyl-1,4-hexanediol 22417-60-3 3,3-dimethyl-1,4-hexanediol method F 3,4-dimethyl-1,4-hexanediol method E 3,5-dimethyl-1,4-hexanediol method H 4,5-dimethyl-1,4-hexanediol method E 5,5-dimethyl-1,4-hexanediol 38624-38-3 2,2-dimethyl-1,5-hexanediol method A 2,3-dimethyl-1,5-hexanediol 62718-05-2 2,4-dimethyl-1,5-hexanediol 73455-82-0 2,5-dimethyl-1,5-hexanediol 58510-28-4 3,3-dimethyl-1,5-hexanediol 41 736-99-6 3,4-dimethyl-1,5-hexanediol method A 3,5-dimethyl-1,5-hexanediol method G 4,5-dimethyl-1,5-hexanediol method F 2,2-dimethyl-1,6-hexanediol 13622-91-8 2,3-dimethyl-1,6-hexanediol method F 2,4-dimethyl-1,6-hexanediol method F 2,5-dimethyl-1,6-hexanediol 49623-11-2 3,3-dimethyl-1,6-hexanediol method F 3,4-dimethyl-1,6-hexanediol 65363-45-3

·· • · · • ···· ·« ·· • · · * « · · · « ·«·· · • · · • · 4·

Table 4 - continued, Isomers of dimethylhexanediol compound name compound registration number in the journal Chemical Abstracts (CAS No.) also suitable for isomers

2.3-dimethyl-1,6-hexanediol

2.4-dimethyl-2,4-hexanediol

2,5-dimethyl-2,4-hexanediol

3.3-dimethyl-2,4-hexanediol

3.4-dimethyl-2,4-hexanediol

3.5-dimethyl-2,4-hexanediol

4.5-dimethyl-2,4-hexanediol

5.5-dimethyl-2,4-hexanediol

2.3-dimethyl-2,4-hexanediol

2.4-dimethyl-2,5-hexanediol

2,5-dimethyl-2,5-hexanediol

3.3-dimethyl-2,5-hexanediol

3.4-dimethyl-2,5-hexanediol 3,3-dimethyl-2,5-hexanediol more preferred isomers

2.2-dimethyl-1,3-hexanediol

2.3-dimethyl-1,3-hexanediol

2.4-dimethyl-1,3-hexanediol

2,5-dimethyl-1,3-hexanediol

3.4-dimethyl-1,3-hexanediol

3.5-dimethyl-1,3-hexanediol

4.4-dimethyl-1,3-hexanediol

4.5-dimethyl-1,3-hexanediol

2.2-dimethyl-1,4-hexanediol

2.3-dimethyl-1,4-hexanediol

2.4-dimethyl-1,4-hexanediol

2,5-dimethyl-1,4-hexanediol

3.3-dimethyl-1,4-hexanediol

3.4-dimethyl-1,4-hexanediol

3.5-dimethyl-1,4-hexanediol

4.5-dimethyl-1,4-hexanediol

26344-17-2

29649-22-7

3899-89-6

42412-51-1

90951-83-0

159300-34-2 method D

108505-10-8 method G method G

110-03-2 method H

99799-30-1 method A

22006-96-8 method D 78122-99-3 method C method D method D method C method C method H method F method G 22417-60-3 method F method E method H method E • 99 9 ·· 99

9 9 99 9 9 9 9 9 9

99 9 9 9 9 99

9999 9 99 999 9 9

9 9 9 9 9 9 9

999 99 999 9999 99 99

Table 4 - continued, Isomers of dimethylhexanediol compound name Chemical Abstracts registration number of the compound (CAS No.) more preferred isomers

5,5-dimethyl-1,4-hexanediol

5,5-dimethyl-1,4-hexanediol

2.2-dimethyl-1,5-hexanediol

2.3-dimethyl-1,5-hexanediol

2.4-dimethyl-1,5-hexanediol

2,5-dimethyl-1,5-hexanediol

3.3-dimethyl-1,5-hexanediol

3.4-Dimethyl-1,5-hexanediol

3.5-dimethyl-1,5-hexanediol

4.5-dimethyl-1,5-hexanediol

3.3-dimethyl-2,6-hexanediol unsuitable even from omer

2.3-dimethyl-1,2-hexanediol

2.4-dimethyl-1,2-hexanediol

2.5-dimethyl-1,2-hexanediol

3.3-dimethyl-1,2-hexanediol

3.4-dimethyl-1,2-hexanediol

3.5-dimethyl-1,2-hexanediol

4.4-dimethyl-1,2-hexanediol

4.5-dimethyl-1,2-hexanediol

5.5-dimethyl-1,2-hexanediol

2.3-dimethyl-2,3-hexanediol

2.4-dimethyl-2,3-hexanediol

2.5-dimethyl-2,3-hexanediol

3.4-dimethyl-2,3-hexanediol

3.5-dimethyl-2,3-hexanediol

4.4-dimethyl-2,3-hexanediol

4.5-dimethyl-2,3-hexanediol

5.5-dimethyl-2,3-hexanediol

2.2-dimethyl-3,4-hexanediol

2.3-dimethyl-3,4-hexanediol

38624-38-3 38624-38-3 method A 62718-05-2 73455-82-0 58510-28-4 4173b-99-6 method A method G method F method A • 9999 • 99

9 9 9

99

9 9 9

9 9

999 «9 9

99

9 9 9

9 99

999 9 9

9 9

99

Table 4 - continued, Isomers of dimethylhexanediol compound name Chemical Abstracts journal compound registration number (CAS No.) unsuitable isomers

2.4-dimethyl-3,4-hexanediol

2.5-dimethyl-3,4-hexanediol 3,4-dimethyl-3,4-hexanediol

Ethylhexanediol isomers compound name Chemical Abstracts journal compound registration number (CAS No.) more preferred isomers

-ethyl-1,3-hexanediol 4-ethyl-1,3-hexanediol 2-ethyl-1,4-hexanediol 4-ethyl-1,4-hexanediol

2-Ethyl-1,5-hexanediol

-ethyl-2,4-hexanediol

-ethyl-2,4-hexanediol

3-ethyl-2,5-hexanediol unsuitable isomers

4-ethyl-1,5-hexanediol

2-ethyl-1,6-hexanediol

3- ethyl- 1,4-hexanediol 3-ethyl- 1,5-hexanediol 3-ethyl- 1,6-hexanediol

2-ethyl-1,2-hexanediol

3-ethyl-1,2-hexanediol 4-ethyl 1,2-hexanediol

3-ethyl-2,3-hexanediol

4-ethyl-2,3-hexanediol

94-96-2 method C 148904-97-6 1113-00-4 58374-34-8 method C 33683-47-5 method F • AA B BA A« BA

AA A A AA B A A · A ·

A BA A A A A BA

A · A A A A B ··· A A

A A A AA AAA

AAA AA AAA AAAAA AA AA

Table 4 - continued, Ethylhexanediol Isomers

compound name compound registration number in the journal Chemical Abstracts (CAS No.) unsuitable isomers 3-ethyl-3,4-hexanediol 3-ethyl-1,3-hexanediol

Methylheptanediol isomers

compound name compound registration number in the journal Chemical Abstracts (CAS No.) suitable isomers 2-methyl-1,3-heptanediol 109417-38-1 3-methyl-1,3-heptanediol 165326-88-5 4-methyl-1,3-heptanediol method C 5-methyl-1,3-heptanediol method D 6-methyl-1,3-heptanediol method C 2-methyl-1,4-heptanediol 15966-03-7 3-methyl-1,4-heptanediol 7748-38-1 4-methyl-1,4-heptanediol 72473-94-0 5-methyl-1,4-heptanediol 63003-04-3 6-methyl-1,4-heptanediol 99799-25-4 2-methyl-1,5-heptanediol 141605-00-7 3-methyl-1,5-heptanediol method A 4-methyl-1,5-heptanediol method A 5-methyl-1,5-heptanediol 99799-26-5 6-methyl-1,5-heptanediol 57740-00-8 2-methyl-1,6-heptanediol 132148-22-2 3-methyl-1,6-heptanediol method G 4-methyl-1,6-heptanediol 156307-84-5 5-methyl-1,6-heptanediol method A 6-methyl-1,6-heptanediol 5392-57-4 2-methyl-2,4-heptanediol 38836-26-9 3-methyl-2,4-heptanediol 6964-04-1 4-methyl-2,4-heptanediol 16532b-87-4

• 99 · » · • 99 • · 9 t • · 9 9

999 99 9 • 9999

99

9 9 ·

9 99

999 9 9

9 9

99

Table 4, continued, Isomers of methylheptanediol compound name Chemical Abstracts registration number of the compound (CAS No.) also suitable for isomers

5-methyl-2,4-heptanediol

6-methyl-2,4-heptanediol

2-methyl-2,5-heptanediol

3-methyl-2,5-heptanediol

4-methyl-2,5-heptanediol

5-methyl-2,5-heptanediol

6-methyl-2,5-heptanediol

2-methyl-2,6-heptanediol

3-methyl-2,6-heptanediol

4-methyl-2,6-heptanediol 3-methyl-3,4-heptanediol

2-methyl-3,5-heptanediol

3-methyl-3,5-heptanediol

4-methyl-3,5-heptanediol method C

79356-95-9

141605-02-9 method G

156407-38-4

148843-72-5

51916-46-2

73304-48-0

29915-96-6

106257-69-6

18938-50-6 method C

99799-27-6

156407-37-3 more preferred isomers

2-methyl-1,3-heptanediol

3-methyl-1,3-heptanediol

4-methyl-1,3-heptanediol

5-methyl-1,3-heptanediol

6-methyl-1,3-heptanediol

2-Methyl-1,4-heptanediol

3-methyl-1,4-heptanediol

4-methyl-1,4-heptanediol

5-methyl-1,4-heptanediol

6-methyl-1,4-heptanediol

2-methyl-1,5-heptanediol

3-methyl-1,5-heptanediol

4-methyl-1,5-heptanediol

5-methyl-1,5-heptanediol

6-Methyl-1,5-6heptanediol

109417-38-1

165326-88-5 method C method D method C

15966-03-7

7748-38-1

72473-94-0

63003-04-3

99799-25-4

141605-00-7 method A method A

99799-26-5

57740-00-8 • φφ φ φφ φφ φφ φφφ» φφφφ φφφφ φ φφ φ φ φ φφ φφφφ φ φ φφφ φ φ φφφ φφ φφφ

Table 4 - continued, Methylheptanediol isomers

compound name compound registration number in the journal Chemical Abstracts (CAS No.) more preferred isomers 2-methyl-1,6-heptanediol 132148-22-2 3-methyl-1,6-heptanediol method G 4-methyl-1,6-heptanediol 156307-84-5 5-methyl-1,6-heptanediol method A 6-methyl-1,6-heptanediol 5392-57-4 2-methyl-2,4-heptanediol, 38836-26-9 3-methyl-2,4-heptanediol, 6964-04-1 4-methyl-2,4-heptanediol, 165326-87-4 5-methyl-2,4-heptanediol, method C 6-methyl-2,4-heptanediol, 79356-95-9 2-methyl-2,5-heptanediol, 141605-02-9 3-methyl-2,5-heptanediol, method H 4-methyl-2,5-heptanediol, 156407-38-4 5-methyl-2,5-heptanediol, 148843-72-5 6-methyl-2,5-heptanediol, 51916-46-2 2-methyl-2,6-heptanediol, 73304-48-0 3-methyl-2,6-heptanediol, 29915-96-6 4-methyl-2,6-heptanediol, 106257-69-6 3-methyl-3,4-heptanediol, 18938-50-6 2-methyl-3,5-heptanediol, method C 4-methyl-3,5-heptanediol, 156407-37-3 inappropriate isomers 2-methyl-1,7-heptanediol 3-methyl-1,7-heptanediol 4-methyl-1,7-heptanediol 2-methyl-2,3-heptanediol 3-methyl-2,3-heptanediol 4-methyl-2,3-heptanediol 5-methyl-2,3-heptanediol 6-methyl-2,3-heptanediol 2-methyl-3,4-heptanediol

this it

Table 4 - continued, Methylheptanediol isomers compound name Chemical Abstracts journal compound registration number (CAS No.) unsuitable isomers

4-methyl-3,4-heptanediol

5-methyl-3,4-heptanediol

6-methyl-3,4-heptaodiol

2-methyl-1,2-heptanediol

3-methyl-1,2-heptanediol

4-methyl-1,2-heptanediol

5-methyl-1,2-heptanediol

6-methyl-1,2-heptanediol

Octanediol isomers compound name Chemical Abstracts journal compound registration number (CAS No.) more preferred isomers

2.4-octanediol

2.5-octanediol

2.6-octanediol

2.7- octanediol

3.5-octanediol

3.6-octanediol

90162-24-6

4527-78-0 method A

19686-96-5

24892-55-5

24434-09-1 unsuitable isomers

1.2- octanediol

1.3- Octanediol

1.4- Octanediol

1.5-octanediol

1.6-octanediol

1.7- octanediol

1.8-octanediol 2,3-octanediol

1117-86-8

23433-OS-8

51916-47-3

2736-67-6

4060-76-6

13175-32-1

629-41-4 e.g. 98464-24-5 • ·· * ·· ·· ·· ···· ··»· ···· • ·· · · · · ·· • · · · · · · ··· φ · ··· ·· ··· ··· ·· ··» ··*· ·· ··

Table 4 - continued, Octanediol Isomers

compound name compound registration number in the journal Chemical Abstracts (CAS No.) inappropriate isomers 3,4-octanediol eg 99799-31-2 3,5-octanediol e.g. 129025-63-4

Table 5

Nonanediol isomers compound name Chemical Abstracts journal compound registration number (CAS No.) more preferred isomers

2,3,3,4-1-tetramethyl-2,4-pentanediol,

19424-43-2 suitable isomers

-tert-butyl-2,4-pentanediol 2,5,5-trimethyl-2,4-hexanediol

3.3.4-trimethyl-2,4-hexanediol

3.3.5-trimethyl-2,4-hexanediol

3.5.5-trimethyl-2,4-hexanediol

4.5.5-trimethyl-2,4-hexanediol

3.3.4-trimethyl-2,5-hexanediol

3.3.5-trimethyl-2,5-hexanediol

142205-14-9 97460-08-7 method D 27122-58-3 method D method D method H method G unsuitable isomers

There are more than 500 inappropriate isomers including the following: 2,4,5-trimethyl-2,4-hexanediol 2,4,5-trimethyl-2,4-hexanediol erythro-2,3,5-trimethyl-2,4-hexanediol threo-2,3,5-trimethyl-2,4-hexanediol 2-ethyl-2-butyl-1,3-propanediol threo-2,3,5-trimethyl-2,4-hexanediol

36587-81-2

36587-81-2

26344-20-7

26343-49-7

115-84-4

26343-49-7 • φφ • · · φ • φφ φφφ • φ φ φ« · φφ φ φ • ··»· • Φ ·· • φ φ φ • ♦ »· φφφφ φ • φ φ • Φ φφ

Table 6

Alkyl glyceryl ethers, di(hydroxyalkyl) ethers and aryl glyceryl ethers compound name compound registration number in the journal Chemical Abstracts (CAS No.) preferred monoglyceryl ethers and their derivatives triethoxylated 3-(butyloxy)-1,2-propanediol tetraethoxylated 3-(butyloxy)-1,2 -propanediol more preferred monoglyceryl ethers and their derivatives

3-(n-pentyloxy)-1,2-propanediol 22636-32-4

3-(2-pentyloxy)-1,2-propanediol

-(3-pentyloxy)-1,2-propanediol

3-(2-methyl-1-butyloxy)-1,2-propanediol

3-(iso-amyloxy)-1,2-propanediol

-(3-methyl-2-butyloxy)-1,2-propanediol

3-(Cyclohexyloxy)-1,2-propanediol

3-(1-Cyclohex-1-enyloxy)-1,2-propanediol

1-(pentyloxy)-1,3-propanediol

2-(2-pentyloxy)-1,3-propanediol

2-(3-pentyloxy)-1,3-propanediol

2-(2-methyl-1-butyloxy)-1,3-propanediol

2-(iso-amyloxy)-1,3-propanediol

2-(3-methyl-2-butyloxy)-1,3-propanediol

2-(Cyclohexyloxy)-1,3-propanediol

2-(1-cyclohex-1-enyloxy)-1,3-propanediol penatethoxylated-3-(butyloxy)-1,2-propanediol hexaethoxylated-3-(butyloxy)-1,2-propanediol heptaethoxylated-3-(butyloxy) -1,2-propanediol octaethoxylated-3-(butyloxy)-1,2-propanediol nonaethoxylated-3-(butyloxy)-1,2-propanediol monopropoxylated-3-(butyloxy)-1,2-propanediol dibutyleneoxytated-3-( butyloxy)-1,2-propanediol tributylenoxylated-3-(butyloxy)-1,2-propanediol • ·· fe ·· fefe ·· ···· · · · · fe * « · • fefe · · · · ·· fefefefe · · · fe·· · fe • fefe fefe ··· ··· fefe fefe· ···· fefe fefe

Table 6 - continued, Alkyl glyceryl ethers...

compound name compound registration number in the journal Chemical Abstracts (CAS No.) more preferred di(hydroxyalkyl) ethers bis(2-hydroxybutyl) ether bis(2-hydroxycyclopentyl) ether unsuitable monoglycerol ethers

-ethyloxy-1,2-propanediol

3-propyloxy-1,2-propanediol

-isopropyloxy-1,2-propanediol

3-butyloxy-1,2-propanediol

3-isobutyloxy-1,2-propanediol

-tert.butyloxy-1,2-propanediol 3-octyloxy-1,2-propanediol 3-(2-ethylhexyloxy)-1,2-propanediol 3-(cyclopentyloxy)-1,2-propanediol 3-(1-cyclohex- 2-enyloxy)-1,2-propanediol 2-(1-cyclohex-2-enyloxy)-1,3-propanediol

Aromatic glyceryl ethers compound name compound registration number in the journal Chemical Abstracts (CAS No.)

suitable aromatic glyceryl ethers 3-phenyloxy-1,2-propanediol 3-benzyloxy-1,2-propanediol 3-(2-phenylethyloxy)-1,2-propanediol 3-(1-phenyl-2-propanyloxy)-1,2- propanediol 2-phenyloxy-1,3-propanediol

2-(m-cresyloxy)-1,3-propanediol 2-(p-cresyloxy)-1,3-propanediol 2-benzyloxy-1,3-propanediol 2-(2-phenylethyloxy)-1,3-propanediol

- 47 • · · · · · A A A A A • · AA A A A

AA AA

Table 6 - continued, Aromatic Glyceryl Ethers Compound Name Chemical Abstracts Compound Registration Number (CAS No.) Suitable Aromatic Glyceryl Ethers

2-(1-Phenylethyloxy)-1,3-propanediol preferred aromatic glyceryl ethers

3-phenyloxy-1,2-propanediol

3-Benzyloxy-1,2-propanediol

3-(2-Phenethyloxy)-1,2-propanediol

2-(m-cresyloxy)-1,3-propanediol

2-(p-cresyloxy)-1,3-propanediol

2-Benzyloxy-1,3-propanediol

2-(2-phenylethyl)-1,3-propanediol more preferred aromatic glyceryl ethers 3-phenyloxy-1,2-propanediol

3- Benzyloxy-1,2-propanediol

3-(2-phenylethyloxy)-1,2-propanediol 2-(m-cresyloxy)-1,3-propanediol 2-(p-cresyloxy)-1,3-propanediol 2-(2-phenylethyloxy)-1,3 -propanediol

Table 7

Alicyclic diols and their derivatives compound name compound registration number in the journal Chemical Abstracts (CAS No.) preferred alicyclic diols and derivatives

1-isopropyl-1,2-cyclobutanediol 59895-32-8

3-ethyl-4-methyl-1,2-cyclobutanediol 3-propyl-1,2-cyclobutanediol 3-isopropyl-1,2-cyclobutanediol

42113-90-6 • · ···· ·

Table 7 - continued, Alicyclic Diols and Their Derivatives Compound Name Chemical Abstracts Compound Registration Number (CAS No.) Preferred Alicyclic Diols and Derivatives

1-Ethyl-1,2-cyclopentanediol

1,2-dimethyl-1,2-cyclopentanediol

1,4-dimethyl-1,2-cyclopentanediol

2,4,5-trimethyl-1,3-cyclopentanediol

3.3-dimethyl-1,2-cyclopentanediol

3.4-dimethyl-1,2-cyclopentanediol

4.5-dimethyl-1,2-cyclopentanediol

3-Ethyl-1,2-cyclopentanediol

4.4-dimethyl-,2-cyclopentanediol

4-ethyl-1,2-cyclopentanediol

1.1-bis(hydroxymethyl)cyclohexane

1.2-bis(hydroxymethyl)cyclohexane

1.2-dimethyl-1,3-cyclohexanediol

1.3-bis(hydroxymethyl)cyclohexane

1,3-dimethyl-1,3-cyclohexanediol

1,6-dimethyl-1,3-cyclohexanediol 1-hydroxy-cyclohexaneethanol

1-hydroxy-cyclohexanemethanol 1-ethyl-1,3-cyclohexanediol

1-methyl-1,2-cyclohexanediol

2.2-dimethyl-1,3-cyclohexanediol

2.3-dimethyl-1,4-cyclohexanediol

2.4-dimethyl-1,3-cyclohexanediol

2,5-dimethyl-1,3-cyclohexanediol

2.6-dimethyl-1,4-cyclohexanediol

-ethyl-1,3-cyclohexanediol

2-Hydroxycyclohexaneethanol 2-Hydroxyethyl-1-cyclohexanol 2-Hydroxymethylcyclohexanol

-hydroxye thy1-1-cyclohexano1

673 96-1 7-1

33046-10-7

89794-56-9

89794-57-0 70051 -69-3 89794-58-1

70197-54-3

2658-60-8

76155-27-6

53023-07-7

13022-98-5

128749-93-9

164713-16-0

40894-17-5

15753-37-6

10601-18-0

52718-65-7

114693-83-3

70156-81-0

34958-42-4

155433-88-8

24682-42-6

89794-52-5

► » · · · • · · · « • · I • · « ·

Table 7 - continued, Alicyclic diols and their derivatives compound name Chemical Abstracts registration number of the compound (CAS No.) preferred alicyclic diols and derivatives

-hydroxycyclohexanethano1

3-Hydroxymethylcyclohexanol

3-methyl-1,2-cyclohexanediol

4.4-dimethyl-1,3-cyclohexanediol

4.5-dimethyl-1,3-cyclohexanediol

4.6-dimethyl-1,3-cyclohexanediol

4-ethyl-1,3-cyclohexanediol

-hydroxyethyl-1-cyclohexanol

4-Hydroxymethylcyclohexanol

4- methyl-1,2-cyclohexanediol

5,5-Dimethyl-1,3-cyclohexanediol

5-ethyl-1,3-cyclohexanediol

1.2-cycloheptanediol

2-methyl-1,3-cycloheptanediol

2-methyl-1,4-cycloheptanediol

4-methyl-1,3-cycloheptanediol

5-methyl-1,3-cycloheptanediol

5-methyl-1,4-cycloheptanediol

6-methyl-1,4-cycloheptanediol

1.3-cyclooctanediol

1.4-cyclooctanediol

1.5-cyclooctanediol diethoxylate 1,2-cyclohexanediol triethoxylate 1,2-cyclohexanediol tetraethoxylate 1,2-cyclohexanediol pentaethoxylate 1,2-cyclohexanediol hexaethoxylate 1,2-cyclohexanediol heptaethoxylate 1,2-cyclohexanediol octaethoxylate 1,2-cyclohexanediol

86576-87-6

23477-91-0

14203-50-0

16066-66-3

33893-85-5

23832-27-1

51335-83-2

108268-28-6

101375-80-8

90201-00-6

101935-36-8

73982-04-4

23418-82-8

• · ·· ·· ·· • · · · • · · · · • · · · · ·

Table 7 - continued, Alicyclic diols and their derivatives compound name compound registration number in the journal Chemical Abstracts (CAS No.) preferred alicyclic diols and derivatives 1,2-cyclohexanediol nonaethoxylate monopropoxylate 1,2-cyclohexanediol monobutylene oxylate 1,2-cyclohexanediol dibutylene oxylate 1, 2-cyclohexanediol tributylene oxylate 1,2-cyclohexanediol more preferred alicyclic diols and their derivatives

1-isopropyl-1,2-cyclobutanediol 3-ethyl-4-methyl-1,2-cyclobutanediol 3-propyl-1,2-cyclobutanediol 3-isopropyl-1,2-cyclobutanediol

59895-32-8

42113-90-6

1-Ethyl-1,2-cyclopentanediol

1,2-dimethyl-1,2-cyclopentanediol

1,4-dimethyl-1,2-cyclopentanediol

3.3-dimethyl-1,2-cyclopentanediol

3.4-dimethyl-1,2-cyclopentanediol

3.5-dimethyl-1,2-cyclopentanediol

3-Ethyl-1,2-cyclopentanediol

4.4-dimethyl-1,2-cyclopentanediol

4-ethyl-1,2-cyclopentanediol

1.1-bis(hydroxymethyl)cyclohexane

1.2-bis(hydroxymethyl)cyclohexane

1,2-dimethyl-1,3-cyclohexanediol

1.3-bis(hydroxymethyl)cyclohexane 1-hydroxy-cyclohexanemethanol 1-methyl-1,2-cyclohexanediol

3-Hydroxymethylcyclohexanol 3-Methyl-1,2-cyclohexanediol

4.4-dimethyl-1,3-cyclohexanediol

4.5-dimethyl-1,3-cyclohexanediol

67396-17-2

33046-20-7

89794-56-9

89794-57-0

70051-69-3

89794-58-1

70197-54-5

2658-60-8

76155-27-6

53013-07-7

13022-98-5

15753-47-6

52718-65-7

23477-91-0

14203-50-0

Table 7 - continued, Alicyclic diols and their derivatives compound name Chemical Abstracts compound registration number (CAS No.) more preferred alicyclic diols and their

4,6-dimethyl-1,3-cyclohexanediol

4-ethyl-1,3-cyclohexanediol

4-hydroxyethyl-1-cyclohexanol

4-Hydroxymethylcyclohexanol

4-methyl-1,2-cyclohexanediol derivs

16066-66-3

33893-85-5

23832-27-1

1,2-cycloheptanediol

108168-28-6 pentaethoxylate 1,2-cyclohexanediol hexaethoxylate 1,2-cyclohexanediol heptaethoxylate 1,2-cyclohexanediol octaethoxylate 1,2-cyclohexanediol nonaethoxylate 1,2-cyclohexanediol monopropoxylate 1,2-cyclohexanediol dibutyleneoxylate 1,2-cyclohexanediol suitable unsaturated alicyclic diols

1-Ethenyl-2-ethyl-1,2-cyclobutanediol

1.2.3.4-tetramethyl-3-cyclobutene-1,2-diol

3.4-diethyl-3-cyclobutene-1,2-diol

3-(1,1-dimethylethyl)-3-cyclobutene-1,2-diol

3-butyl-3-cyclobutene-1,2-diol

1,2-dimethyl-4-methylene-1,2-cyclopentanediol 1-ethyl-3-methylene-1,2-cyclopentanediol

4-(1-propenyl)-1,2-cyclopentanediol

1-ethyl-3-methyl-3-cyclopentene-1,2-diol 1-ethenyl-1,2-cyclohexanediol 1-methyl-3-methylene-1,2-cyclohexanediol 1-methyl-4-methylene-1,2 -cyclohexanediol 3-ethenyl-1,2-cyclohexanediol 4-ethenyl-1,2-cyclohexanediol 2,6-dimethyl-3-cyclohexene-1,2-diol

58016-14-1

90112-64-4

142543-60-0

142543-56-4

142543-55-3

103150-02-3

90314-52-6

128173-45-5

90314-43-5

134134-16-0

98204-78-5

133358-53-9

55310-51-5

85905-16-4

81969-75-7 • ·

• ·

Table 7 - continued, Alicyclic diols and their derivatives compound name Chemical Abstracts registration number of the compound (CAS No.) suitable saturated alicyclic diols

6.6-dimethyl-3-cyclohexene-1,2-diol

3.6-dimethyl-4-cyclohexene-1,2-diol

4,5-dimethyl-4-cyclohexene-1,2-diol

3-cycloacetene-1,2-diol

4-cycloacetene-1,2-diol

5-cycloacetene-1,2-diol unsuitable unsaturated cyclic diols 1-(1-methylethenyl)-1,2-cyclopentanediol

1-cyclopentyl-1,2-propanediol

2-(1-methylethylidene)-1,3-cyclopentanediol 2-(1-cyclopenten-1-yl)-1,3-propanediol

2-(2-cyclopenten-1-yl)-1,3-propanediol

1-(1-cyclohexen-1-yl-1,2-ethanediol).

1-(3-cyclohexen-1-yl)-1,2-ethanediol

5.5-dimethyl-2-cyclohexene-1,4-diol

3.6-dimethyl-4-cyclohexene-1,3-diol

2-methylene-1-cycloheptanediol

1-methyl-5-cycloheptene-1,3-diol

5-methyl-5-cycloheptene-1,3-diol

2-cyclooctene-1,4-diol

61875-93-2

156808-73-0

154351-54-9

170211-27-5

124791-61-3

117468-07-2

61447-83-4

55383-20-5

65651-46-9

77192-43-9

25462-31-1

151674-61-2

64011-53-6

147274-55-3

127716-90-9

132292-67-2

160813-32-1

160813-32-1

37996-40-0 • · ··· ♦ • * • · 4

Table 8

Alkoxylated derivatives of C ₃ -C ₇ diols

In the following tables, EO stands for polyethoxyl groups, ie -(CH ₂ CH ₂ O) _n H; Me-E _n means polyethoxyl groups terminated by methyl -(CH ₂ CH ₂ O) _n CH ₃ ; 2(Me-E _n ) means two Me-E _n groups; PO means polypropoxy groups -(CH(CH ₃ )CH ₂ O) _n H; BO means polybutyleneoxy groups (CH(CH ₂ CH ₃ )CH ₂ ) _n H; and n-BO means a poly(n-butylenoxy) group or a poly(tetramethyleneoxy) group -(CH ₂ CH ₂ CH ₂ CH ₂ O) _n H. All the mentioned alkoxy derivatives can be used, data on preferred substances are given in the second line. Common synthetic methods used to prepare these alkylated compounds are outlined below.

Table 8a

starting material alkoxy groups in the derivative starting materials name registration CAS number E0 ^(b> 1(Me-En) ^<C> 2(Me-En) P0 ^(e) n-Bc/ ^f ' BO^ ⁹ ' (CAS No.) 1,2-propanediol (C3) 57-55-6 1-4 3-4 4 2-methyl-1,2-propanediol (C4) 558-43-0 4-10 1 8-10 1 3 1,3-Propanediol(C3) 504-63-2 6-8 5-6 8 6 2,2-diethyl-1,3-propanediol (C7) 115-76-4 1-7 1-2 4-7 1 2 2,2-dimethyl-1,3-propanediol (C5) 126-30-7 3-4 1-2 4 2-(1-methylpropyl)-1,3-propane- 33673-01-7 1-7 1-2 diol (C7) 4-7 1 2 2-(2-methylpropyl)-1,3-propane- 26462-20-8 1-7 1-2 diol <C7) 4-7 1 2

» ·· • · 4 • · · ·· · ···· ··· · • · • · <

Table 8a - continued

starting material of the alkoxy group in the deriv starting materials name registration number CAS EO ^<b) 1(Me-En) ^(C) 2(Me-En) ^{(a) (b) (c) (d)} P0 ^(e) n-BO ^(f) BO* ⁹ ' (CAS No.)

2-ethyl-1,3-propanediol (C5) 2612-29-5 6-10 9-10 1 3 2-ethyl-2-methyl-1,3-propanediol 77-84-9 1-6 (C6) 3-6 2 1 2-isopropyl-1,3-propanediol (C6) 2612-27-3 1-6 3-6 2 1 2-methyl-1,3-propanediol (C4) 2163-42-0 2-5 4-5 4-5 5 2 2-ethyl-2-isopropyl-1,3-pro- 2109-23-1 2-9 1-3 pandiol (C7) 6-9 1 2-3 2-methyl-2-propyl-1,3-propane- 78-26-2 1-7 1-2 diol (C7) 4-7 1 2 2-propyl-1,3-propanediol <C6) 2612-28-4 1-4 2 1

(a) in this and other parts of Table 8 are given the numbers of alkoxy groups in the compounds which are suitable for use according to the present invention. The first line shows the general range of the number of alkoxy groups, the second line shows the range of the number of alkoxy groups in the preferred compounds (b) the range of the average number of groups (CH^CH^O) in the polyethylene oxide derivative (c) the range of the average number of groups (CH^CH^O ) in a polyethylene oxide derivative with one methyl end group ich ₂ ch ₂ o) a polyethylene oxide derivative with two methyl end groups (d) the range of the average number of groups by groups (e) the range of the average number of groups (CHÍCH^JC^O) in the polypropylene oxide derivative (f) the range of the average number of groups (CH ₂ CH ₂ CH ₂ CH ₂ O) in polytetramethyleneoxy deriv. (cf) the range of the average number of groups (CH (CH CH ) CH ₂ O) in the polybutylene oxide derivative.

··· ····

Table 8b Name of the starting substance (a) Alkoxy group in the derivative of the starting substance CAS registration number (CAS No.)

EO (b) (Me-En) (c)

2(Me-En) (d)

PO (e) n-BO (f)

Jg)

1,2-butanediol (C4) 584-03-2 2-8 6-8 2-3 2,3-dimethyl-1,2-butanediol (C6) 66553-15-9 1-6 1-2 2-5 1 2-ethyl-1,2-butanediol (C6) 66553-16-0 1-3 1 2-methyl-1,2-butanediol (C5) 41051-72-3 1-2 1 3,3-dimethyl-1,2-butanediol (C6) 59562-82-2 1-6 1-2 2-5 1 3-methyl-1,2-butanediol (C5) 50468-22-9 1-2 1 1,3-butanediol (C4) 107-88-0 3-6 5 5-6 2,2,3-trimethyl-1,3-butane- 16343-75-2 1-2 diol (C5) 1-3 2 2,2-dimethyl-1,3-butanediol (C6) 76-35-7 3-8 6-8 3 2,3-dimethyl-1,3-butanediol (C6) 24893-35-4 3-8 6-8 3 2-ethyl-1,3-butanediol (C6) 66553-17-1 1-6 4-6 2-3 2-ethyl-2-methyl-1,3-butanediol method C 2-4 (C7) 1 1 3 2-ethyl-3-methyl-1,3-butanediol 68799-03-1 2-4 <C7) 1 1 3 2-isopropyl-1,3-butanediol (C7) 66567-04-2 2-4 1 1 3 2-methyl-1,3-butanediol (C5) 684-84-4 1-3 2-3 4

• · • · ··· ··

Table 8b - continued

starting material of the alkoxy group in the deriv starting materials name registration CAS number (CAS No.) EO ^(b) 1(Me-En) ^<C) 2(Me-En) ^<d> P0 ^(e) n-BO ^(f) bo ^<9) 2-propyl-1,3-butanediol (C7) 66567-03-1 2-9 1-3 6-8 1 2-3 3-methyl-1,3-butanediol (C5) 2568-33-4 1-3 2-3 4 1,4-Butanediol (C4) 110-63-4 2-4 4-5 2 3-4 4-5 2,3-trimethyl-1,4-butane- 162108-60-3 2-9 1-3 diol (C7) 6-9 1 2-3 2,2-dimethyl-1,4-butanediol (C6>). 32812-23-0 1-6 3-6 2 1 2,3-dimethyl-1,4-butanediol (C6) 57716-80-4 1-6 3-6 2 1 2-ethyl-1,4-butanediol (C6) 57716-79-7 1 1-4 2 2-ethyl-2-methyl-1,4-butanediol 76651-98-4 1-7 1-2 (C7) 4-7 1 2 2-ethyl-3-methyl-1,4-butanediol 66225-34-1 1-7 1-2 (C7) 4-7 1 2 2-isopropyl-1,4-butanediol (C7) 39497-66-0 1-7 1-2 4-7 1 2 2-methyl-1,4-butanediol (C5) 2938-98-9 6-10 1 9-10 1 3 2-propyl-1,4-butanediol (C7> 2946-68-3 1-5 1-2 2-5 1 3-ethyl 1-1-methyl-1,4-butanediol method F 2-9 1-3 (C7) 6-8 1 2-3 2,3-butanediol (C4) 513-85-9 6-10 1 9-10 1 3-4 2,3-dimethyl-2,3-butanediol (C6) 76-09-5 3-9 1-3 7-9 1 2-3 2-methyl-2,3-butanediol (C5) 5396-58-7 1-5 2-5 2 1

• ftft

9 · • ··

9 9 9

9 9

999 99

99

9 9 ·

• 9

9

999 9999

Table 8b - legend (a) in this part of Table 8, the numbers of alkoxy groups in the compounds which are suitable for use according to the present invention are given. The first line shows the general range of the number of alkoxy groups, the second line shows the range of the number of alkoxy groups in the preferred compounds (b) the range of the average number of groups (CH^CH^O) in the polyethylene oxide derivative (CH CH 0) in the polyethylene oxide derivative with one methyl (c) range of the average number of groups by the end group (d) range of the average number of groups (CH^CH^O) in the polyethylene oxide derivative with two methyl end groups (e) range of the average number of groups (CHÍCH^JCH^O) in the polypropylene oxide derivative (f) range of the average number of groups (CH^CH^CH^CH^O) in the polytetramethylene oxide deriv.

(g) range of the average number of groups (CH(CH^CH^)CH^O) in the polybutylene oxide derivative.

Table 8c

starting material of the alkoxy group in the deriv starting materials name registration CAS number (CAS No.) E0 ^(b) 1(Me-En) ^<C) 2 (Me-En) ^{(d) after} n-B0 ^(f > B0<9> 1,2-pentanediol (C5) 5343-92-0 3-10 2-3 7-10 1 3 2-methyl-1,2-pentanediol (C6) 20667-05-4 1-3 1 3-methyl-1,2-pentanediol (C6) 159623-53-7 1-3 1 4-methyl-1,2-pentanediol (C6) 72110-08-8 1-3 1 1,3-pentanediol (C5) 3174-67-2 1-2 3-4 2,2-dimethyl-1,3-pentanediol (C7) 2157-31-5 2-4 1 1 3 2,3-dimethyl-1,3-pentanediol (C7) 66225-52-3 2-4 1 1 3 2,4-dimethyl-1,3-pentanediol(C7) 60712-38-1 2-4 1 1 3 2-ethyl-1,3-pentanediol (C7) 29887-11-4 2-9 1-3 6-8 1 2-3 2-methyl-1,3-pentanediol (C6) 149-31-5 1-6 1

4-6

2-3

Table 8c - continued starting substance • ·* φφ · · • φφ • · φ φ • · φ φφφ φφ • φφ φφ φ · φ · φ φ φ φ φφφ φφφφ φφ φφ φ φ φ φ φ φφ φφφ φ · φ φ φ φφ φ* alkoxy group in the derivative of the starting substance registration name

CAS number (CAS No.) EO ^(b) 1(Me-En) ^<0> 2(Me-En) ^(d) PO* ^e> n-B0 ^(f) BO 3,4-dimethyl-1,3-pentanediol (C7) 129851-50-9 2-4 1 1 3 3-methyl-1,3-pentanediol(C6) 33879-72-0 1-6 1 4-6 2-3 4,4-dimethyl-1,3-pentanediol(C7) 30458-16-3 2-4 1 1 3 4-methyl 1,3-pentanediol(C6) 54876-99-2 1-6 1 4-6 2-3 1,4-pentanediol(C5 ) 626-9S-9 1-2 3-4 2,2-dimethyl-1,4-pentanediol (C7) the P method 2-4 1 1 3 2,3-dimethyl-1,4-pentanediol (C7) method F 2-4 1 1 3 2,4-dimethyl-1,4-pentanediol (C7) method F 2-4 1 1 3 2-methyl-1,4-pentanediol (C6) 6287-17-8 1-6 1 4-6 2-3 3,3-dimethyl-1,4-pentanediol (C7) 81887-62-9 2-4 1 1 3 3,4-dimethyl-1,4-pentanediol (C7) 63521-36-8 2-4 1 1 3 3-methyl-1,4-pentanediol (C6) 26787-63-3 1-6 1 4-6 2-3 4-methyl-1,4-pentanediol (C6) 1462-10-8 1-6 1 4-6 2-3 1,5-pentanediol (C5) 111-29-5 4-10 8-10 1 3 2,2-dimethyl-1,5-pentanediol (C7) 3121-82-2 1-7 1-2 4-7 1 2 2 3-dimethyl-1,5-pentanediol (C7) 81554-20-3 1-7 1-2 4-7 1 2

99

99

9 9

9 9

999 99

99

I 9 9 <

» 9 99

999 9

Table 8c - continued

starting material of the alkoxy group in the deriv starting materials name registration CAS number (CAS No.) EO ^(b > l(Me-En) ^<C> 2 (Me-Επ) ^(d) PO ^íe> n-BO < ^f) BO* ³ ' 2,4-dimethyl-1,5-pentanediol(C7) 2121-69-9 1-7 1-2 4-7 1 2 2-ethyl-1,5-pentanediol (C7) 14189-13-0 1-5 1-2 2-5 1 2-methyl-1-1,5-pentanediol (C6) 42856-62-2 1-4 2 3,3-dimethyl-1,5-pentanediol (C7) 53120-74-4 1-7 1-2 4-7 1 2 3-methyl-1,5-pentanediol (C6) 4457-71-0 1-4 2 2,3-pentanediol (C5) 42027-23-6 1-3 2 2-methyl-2,3-pentanediol (C6) 7795-80-4 1-7 1-2 4-7 1 2 3-methyl-2,3-pentanediol(C6) 63521-37-9 1-7 1-2 4-7 1 2 4-methyl-2,3-pentanediol (C6) 7795-79-1 1-7 1-2 4-7 1 2 2,4-pentanediol (C5) 625-69-4 1-4 2-4 4 2,3-dimethyl-2,4-pentanediol (C7) 24893-39-8 1-4 2-4 2 2,4-dimethyl-2 _/ 4-pentanediol (C7) 24892-49-7 1-4 2-4 2 2-methyl-2,4-pentanediol (C6) 107-41-5 5-10 8-10 3 3,3-dimethyl-2,4-pentanediol (C7) 24892-50-0 1-4 2-4 2 3-methyl-2,4-pentanediol (C6) method H 5-10 8-10 3

·· » '

AA

- 60 ·· A A • · • A • · A·· AAAA

AA 1 » · A > A <

AAA A A ·

Table 8c - legend (a) in this Part of Table 8 are given the numbers of alkoxy groups in the compounds which are suitable for use according to the present invention. The first line shows the general range of the number of alkoxy groups, the second line shows the range of the number of alkoxy groups in the preferred compounds (b) the range of the average number of groups (CH^CH^O) in the polyethylene oxide derivative (CH^CH^O) in the polyethylene oxide derivative with one methyl ( c) range of the average number of groups by the end group (d) range of the average number of groups (CH^CH^O) in the polyethylene oxide derivative with two methyl end groups (e) range of the average number of groups (CHÍCH^JC^O) in the polypropylene oxide derivative (f) range of the average of the number of groups (CH^CH^CH^CH^O) in the polytetramethyleneoxy deriv.

(g) range of the average number of groups (CH(CH^CH^)CH^O) in the polybutylene oxide derivative.

Table 8d

starting material of the alkoxy group in the deriv starting materials name registration CAS number (CAS No.) E0 ^(b) (C) liMe-En) AF ^(s) n-B0 ^(f) BO<*> 1,3-Hexanediol (C6) 21531-91-9 1-5 2-5 2 1 2-methyl-1,3-hexanediol (C7) 66072-21-7 2-9 1-3 1 6-8 1 2-3 3-methyl-1,3-hexanediol <C7) method D 2-9 1-3 6-8 1 2-3 4-methyl-1,3-hexanediol (C7) method C 2-9 1-3 6-8 1 2-3 5-methyl-1,3-hexanediol (C7) 109863-14-1 2-9 1-3 6-8 1 2-3 1,4-Hexanediol (C6) 16432-53-4 1-5 2-5 2 1 2-methyl-1,4-hexanediol <C7) method F 2-9 1-3 6-8 1 2-3 3-methyl-1,4-hethanediol <C7) 66225-36-3 2-9 1-3 6-8 1 2-3 4-methyl-1,4-hexanediol <C7) 40646-08-0 2-9 1-3 6-8 1 2-3 5-methyl-1,4-hexanediol <C7) 38624-36-1 2-9 1-3 6-8 1 2-3

99

9 9 9 • ·· • 9 · ·

9 ·

9 ·· • ·· • · * · ·

9 9 • ·

9·· 9999

9 9 9

9 99

9 9 9

9 9

99

Table 8d - continued

starting material of the alkoxy group in the deriv starting materials name registration CAS number (CAS No.) EO ^(b > (C) 1(Me-En) ^after n-B0 ^(f) ΒΟ<*> 1,5-Hexanediol (C6) 928-40-5 1-5 2-5 2 1 2-methyl-1,5-hexanediol (C7) method F 2-9 1-3 6-8 1 2-3 3-methyl-1,5-hexanediol (C7) method F 2-9 1-3 6-8 1 2-3 4-methyl-1,5-hexanediol (C7) 66225-37-4 2-9 1-3 6-8 1 2-3 5-methyl-1,5-hexanediol (C7) 1462-11-9 2-9 1-3 6-8 1 2-3 1,6-Hexanediol (C6) 629-11-8 1-2 1-2 4 2-methyl-1,6-hexanediol (IC7) 25258-92-8 1-5 1-2 2-5 1 3-methyl-1,6-hexanediol (C7) 4089-71-8 1-5 1-2 2-5 1 2,3-Hexanediol (C6) 617-30-1 1-5 1-2 2-5 1 2,4-Hexanediol (C6) 19780-90-6 3-8 5-8 3 2-methyl-2,4-hexanediol (C7) 66225-35-2 1-2 1-2 3-methyl-2,4-hexanediol (C7) 116530-79-1 1-2 1-2 4-methyl-2,4-hexanediol (C7) 38836-25-8 1-2 1-2 5-methyl-2,4-hexanediol (C7) 54877-00-8 1-2 1-2 2,5-Hexanediol (C6) 2935-44-6 3-8 5-8 3 2-methyl-2,5-hexanediol (C7) 29044-06-2

1-2 1-2 » « » 4 ··

9* 4» 9 ·

· · • ·

999 9999

89 > 9 · 4 ø · ··

999 8 4 • * 4

9 99

Table 8d - continued

default substance ^<a) of the alkoxy group in the deriv default substances name registration CAS number (CAS No.) EO ^(b) (C) 1 (Me-En) PO ^{(el 1} n-BO ^<f) Βθ'9> 3-methyl- 2,5· -hexanediol (C7) method H 1-2 1-2 3,4-hexanediol (C6) 922-17-8 1-5 2-5 1

(a) in this part of Table 8 are given the numbers of alkoxy groups in the compounds which are suitable for use according to the present invention. The first line shows the general range of the number of alkoxy groups, the second line shows the range of the number of alkoxy groups in the preferred compounds (b) the range of the average number of groups (CH ₂ CH ₂ O) in the polyethylene oxide derivative (c) the range of the average number of groups (CH ₂ CH ₂ O ) in polyethylene oxide derivative with one methyl end group (e) range of average number of groups (CH(CH^)CH ₂ O) in polypropylene oxide derivative (f) range of average number of groups (CH ₂ CH ₂ CH ₂ CH ₂ O) in polytetramethylene oxide derivative.

(g) range of the average number of groups (CH (C^CH^) CH ₂ O) in the polybutylene oxide derivative.

Table 8e

starting material of the alkoxy group in the derivative of the starting substance name registration CAS number (CAS No.) E0 ^(b > (no. 1 1(Me-En) AF ^(s) n-B0 ^(f > 1,3-Heptanediol (C7) 23433-04-7 1-7 1-2 3-6 1 2 1,4-Heptanediol (C7) 40646-07-9 1-7 1-2 3-6 1 2 1,5-Heptanediol (C7) 60096-09-5 1-7 1-2 3-6 1 2 1,6-Heptanediol (C7) 13175-27-4 1-7 1-2 3-6 1 2 1,7-Heptanediol (C7) 629-30-1 1-2 1 2,4-Heptanediol <C7) 20748-86-1 3-10 7-10 1 1 3 2,5-Heptanediol(C7) 70444-2S-6 3-10

3

7-10 ·· ♦ · • ·· • · · · • ♦ · ··· ··

2,6-Heptanediol(C7)

3, 5-Heptanediol (C7) • ·· ·· · · • · • · · • · «·· ····

5969-12-0 3-10

7-10 1 1

86632-40-8 3-10

7-10 1 1 ·· ·* • · · • ·· ··· · * • · · • · ·« (a) in this part of Table 8, the numbers of alkoxy groups in the compounds which are suitable for use according to this invention are given. The first line shows the general range of the number of alkoxy groups, the second line shows the range of the number of alkoxy groups in the preferred compounds (b) the range of the average number of groups (CH ₂ CH ₂ O) in the polyethylene oxide derivative (c) the range of the average number of groups ÍCH ₂ CH ₂ 0) in polyethylene oxide derivative with one methyl end group (e) range of average number of groups (CH (CH^) CH ₂ O) in polypropylene oxide derivative (f) range of average number of groups (CH ₂ CH ₂ CH ₂ CH ₂ O) in polytetramethylene oxide derivative.

Table 9

Aromatic diols compound name Chemical Abstracts journal compound registration number (CAS No.) suitable aromatic diols

1-phenyl-1,2-ethanediol

1-phenyl-1,2-propanediol

2-phenyl-1,2-propanediol

3-phenyl-1,2-propanediol

1-(3-methylphenyl)-1,3-propanediol

1-(4-methylphenyl)-1,3-propanediol

2- methyl-1-phenyl-1,3-propanediol 1-phenyl-1,3-butanediol

-phenyl-1,3-butanediol

1-phenyl-1,4-butanediol

2-phenyl-1,4-butanediol 1-phenyl-2,3-butanediol

93-56-1

1855-09-0

87760-50-7

17131-14-5

51699-43-5

159266-06-5

139068-60-3

118100-60-0

68330-54-1

136173-88-1

95840-73-6

169437-68-7 preferred aromatic diols 1-phenyl-1,2-ethanediol 1-phenyl-1,2-propanediol

93-56-1

1855-09-0 • · • · ····· · · ··

Table 9, continued, Aromatic diols

name of the compound registration number of the compound in the journal Chemical Abstracts (CAS No.) preferred aromatic diols 1-phenyl-1,2-propanediol 1855-09-0 2-phenyl-1,2-propanediol 87760-50-7 3-phenyl-1,2-propanediol 17131-14-5 1-(3-methylphenyl)-1,3-propanediol 51699-43-5 1-(4-methylphenyl)-1,3-propanediol 159266-06-5 2-methyl-1-phenyl-1,3-propanediol 139068-60-3 1-phenyl-1,3-butanediol 118100-60-0 3-phenyl-1,3-butanediol 68330-54-1 1-phenyl-1,4-butanediol 136173-88-1 more preferred aromatic diols 1-phenyl-1,2-propanediol 1855-09-0 2-phenyl-1,2-propanediol 87760-50-7 3-phenyl-1,2-propanediol 17131-14-5 1-(3-methylphenyl)-1,3-propanediol 51699-13-5 1-(4-methylphenyl)-1,3-propanediol 159266-06-5 2-methyl-1-phenyl-1,3-propanediol 139068-60-3 3-phenyl-1,3-butanediol 68330-54-1 1-phenyl-1,4-butanediol 136173-88-1 inappropriate aromatic diols 1-phenyl-1,3-propanediol 2-phenyl-1,3-propanediol 1-phenyl-1,2-butanediol 154902-08-6 2-phenyl-1,2-butanediol 157008-55-4 3-phenyl-1,2-butanediol 141505-72-8 4-phenyl-1,3-butanediol 143615-31-0 2-phenyl-1,3-butanediol 103941-94-2 4-phenyl-1,3-butanediol 81096-91-5 2-phenyl-2,3-butanediol 138432-94-7

ΦΦΦ · · · · φ φ · · · • ·· · · φφφφ • · · · * φ φ Φφφφ φ φφφ φφ φφφ φφφ φφ φφφ φφφφ φφ φφ

Principal solvents that are homologues of the previously mentioned compounds or have analogous structures, but in which one or more CH ₂ groups are present, while the number of hydrogen atoms is preserved due to the presence of double bonds, are also suitable for use in the processes of this invention, and the following are examples of such compounds:

Table 10

Unsaturated diols compound name chemical abstracts registration number (CAS No.) suitable unsaturated diols

2.2-di-2-propenyl-1,3-propanediol

2-(1-pentenyl)-1,3-propanediol

2-(2-methyl-2-propenyl)-2-(-propenyl)-1,3-propanediol

2-(3-methyl-1-butenyl)-1,3-propanediol

2-(4-pentenyl)-1,3-propanediol

2-Ethyl-2-(2-methyl-2-propenyl)-1,3-propanediol

2-Ethyl-2-(2-propenyl)-1,3-propanediol

2-methyl-2-(3-methyl-3-butenyl)1,3-propanediol

2.2-Diallyl-1,3-butanediol

2-(1-ethyl-1-propenyl)-1,3-butanediol 2-(2-butenyl)-methyl-1,3-butanediol 2-(3-methyl-2-butenyl)-1,3-butanediol 2 -ethyl-2-(2-propenyl)-1,3-butanediol

2-methyl-2-(1-methyl-2-propene)1,3-butanediol

2.3-Bis(1-methylethylidene)-1,4-butanediol

2-(3-methyl-2-butenyl)-3-methylene-1,4-butanediol

2-(1,1-dimethylpropyl)-2-butene-1,4-diol

55038-13-6

138436-18-7

121887-76-1

138436-17-6

73012-46-1

91367-61-2

27606-26-4

132130-95-1

103985-49-5

116103-35-6

92207-83-5

98955-19-2

122761-93-7

141585-58-2

52127-63-6

115895-78-8

91154-01-7 • ·

Table 10 - continued, Unsaturated diols • · • « »0 0 0 compound name Chemical Abstracts registration number of the compound (CAS No.) suitable unsaturated diols

2-(1-methylpropyl)-2-butene-1,4-diol 2-butyl-2-butene-1,4-diol 2-ethenyl-3-ethyl-1,3-pentanediol

2-ethenyl-4,4-dimethyl-1,3-pentanediol

3- methyl-2-(2-propenyl)-1,4-pentanediol 2-(1-propenyl)-1,5-pentanediol,

-(2-propenyl)-1,5-pentanediol,

2-ethylidene-3-methyl-1,5-pentanediol

2- propylidene-1,5-pentanediol

3- ethylidene-2,4-dimethyl-2,4-pentanediol 2-(1,1-dimethylethyl)-4-pentene-1,3-diol 2-ethyl-2,3-dimethyl-4-pentene-1, 3-diol

4-ethyl-2-methylene-1,4-hexanediol

2.3.5-trimethyl-1,5-hexadiene-3,4-diol

5-ethyl-3-methyl-1,5-hexadiene-3,4-diol 2-(1-methylethenyl)-1,5-hexanediol

2-ethenyl-1,6-hexanediol

5.5-dimethyl-1-hexene-3,4-diol

5.5-dimethyl-1-hexene-3,4-diol

4-ethenyl-2,5-dimethyl-2-hexene-1,5-diol 2-ethenyl-2,5-dimethyl-3-hexene-1,6-diol

2-ethyl-3-hexene-1,6-diol

3.4-dimethyl-3-hexene-1,6-diol

2.5-dimethyl-hexene-2,3-diol

3,4-dimethyl-4-hexene-2,3-diol

3-(2-propenyl-5-hexene-1,3-diol

2.3-dimethyl-5-hexene-2,3-diol

3.4-dimethyl-5-hexene-2,3-diol

3.5-dimethyl-5-hexene-2,3-diol

3-ethenyl-2,5-dimethyl-5-hexene-2,4-diol

91154-00-6

153943-66-9

104683-37-6

143447-08-9

139301-86-3

84143-44-2

134757-01-0

42178-93-8

58203-50-2

88610-19-9

109788-04-7

90676-97-4

66950-87-6

18984-03-7

18927-12-3

96802-18-5

66747-31-7

169736-29-2

120191-04-0

70101-76-7

112763-52-7

84143-45-3

125032-66-8

13295-61-9

135367-17-8

74693-24-6

154386-00-2

135096-13-8

134626-63-4

155751-24-9

Table 10 - continued, Unsaturated diols compound name Chemical Abstracts compound registration number (CAS No.) suitable unsaturated diols

6-methyl-5-methylene-1,4-heptanediol

2,3-dimethyl-1,5-heptadiene-3,4-diol 6-methyl-5-methylene-1,4-heptanediol

2.3-dimethyl-1,5-heptadiene-3,4-diol

2,5-dimethyl-1,5-heptadiene-3,4-diol

3,5-dimethyl-1,5-heptadiene-3,4-diol

2,6-bis(methylene)-1,7-heptanediol

4-methylene-1,7-heptanediol

2.4-dimethyl-1-heptene-3,5-diol

2.6-dimethyl-1-heptene-3,5-diol

3-ethenyl-5-methyl-1-heptene-3,5-diol

6.6-dimethyl-1-heptene-3,5-diol

4.6-dimethyl-2,4-heptadiene-2,6-diol

4.4-dimethyl-2,5-heptadiene-1,7-diol

2,5,5-trimethyl-2,6-heptadiene-1,4-diol

5.6-dimethyl-2-heptene-1,4-diol

5-ethyl-2-heptene-1,5-diol

2-methyl-2-heptene-1,7-diol

4.6-dimethyl-3-heptene-1,5-diol

3- methyl-6-methylene-3-heptene-1,7-diol

2.4-dimethyl-3-heptene-2,5-diol

2,5-dimethyl-3-heptene-2,5-diol

2.6-dimethyl-3-heptene-2,6-diol

4.6-dimethyl-3-heptene-2,6-diol

2,4-dimethyl-S-heptene-1,3-diol

3.6-dimethyl-5-heptene-1,3-diol

2.6-dimethyl-5-heptene-1,4-diol

3.6-dimethyl-5-heptene-1,4-diol

2,3-dimethyl-5-heptene-2,4-diol

2,2-dimethyl-6-heptene-1,3-diol

4-(2-Propenyl)-6-Heptene-1,4-diol

5.6-dimethyl-6-heptene-1,4-diol

100590-29-2

18927-06-5

100590-29-2

18927-06-5

22607-16-5

18938-51-7

139618-24-9

71370-08-6

155932-77-7

132157-35-8

61841-10-9

109788-01-4

102605-95-8

162816-19-5

115346-30-0

103867-76-1

104683-39-8

74868-68-1

147028-45-3

109750-55-2

98955-40-9

24459-23-2

160524-66-3

59502-66-8

123363-69-9

96924-52-6

106777-98-4

106777-99-5

104651-56-1

140192-39-8

1727-87-3

152344-16-6

Table 10 - continued, Unsaturated diols »0 0000 0«0· 00 0 * 0000 0 0 0 0 0 0 000 0 0 0 0 0 · 0 0 0 00 0000000 00 00 compound name compound registration number in the journal Chemical Abstracts (CAS No .) suitable unsaturated diols

2.4- dimethyl-6-heptene-1,5-diol 2-ethylidene-6-methyl-6-heptene-1,5-diol

4-(2-Propenyl)-6-Heptene-2,4-diol

5.5-dimethyl-6-heptene-2,4-diol

4.6-dimethyl-6-heptene-2,5-diol

5-ethenyl-4-methyl-6-heptene-2,5-diol

2-methylene-1,3-octenediol

2.6-dimethyl-1,6-octadiene-3,5-diol

3.7-dimethyl-1,6-octadiene-3,5-diol

2.6-dimethyl-1,7-octadiene-3,6-diol

2.7-Dimethyl-1,7-octadiene-3,6-diol

3.6-dimethyl-1,7-octadiene-3,6-dioe

3- Ethenyl-1-acetene-3,6-diol

2.7-Dimethyl-2,4,6-octatriene-1,8-diol

3.7-dimethyl-2,4-octadiene-1,7-diol

2.6-dimethyl-2,5-octadiene-1,7-diol

3.7-dimethyl-2,5-octadiene-1,7-diol

3.7-dimethyl-2,6-octadiene-1,4-diol (rosiridol)

2-methyl-2,6-octadiene-1,8-diol

3.7-dimethyl-2,7-octadiene-1,4-diol

2.6-dimethyl-2,7-octadiene-1,5-diol

2.6-dimethyl-2,7-octadiene-1,6-diol-(8-hydroxylinalool)

2.7-Dimethyl-2,7-octadiene-1,6-diol 2-octene-1,4-diol

2-Octene-1,7-diol

2-methyl-6-methylene-2-octene-1,7-diol

3.7-dimethyl-3,5-octadiene-1,7-diol

2.7-dimethyl-3,5-octadiene-2,7-diol

4-methylene-3,5-octenediol,

2,6-dimethyl-3,7-octadiene-1,6-diol

74231-27-9

91139-73-0

101536-75-8

98753-77-6

134876-94-1

65757-31-5

108086-78-8

91140-06-6

75654-19-2

51276-33-6

26947-10-4

31354-73-1

65757-34-8

162648-63-7

136054-24-5

91140-07-7

117935-59-8

101391-01-9

149112-02-7

91140-08-8

91140-09-9

103619-06-3

60250-14-8

40735-15-7

73842-95-2

91140-16-8

62875-09-6

7177-18-6

143233-15-2

127446-29-1 • · · · ·

Table 10 - continued, Unsaturated diols * · «

·· name of the compound registration number of the compound in the journal Chemical Abstracts (CAS No.)

suitable unsaturated diols 2,7-dimethyl-3,7-octadiene-2,5-diol 171436-39-8 2,6-dimethyl-3,7-octadiene-2,6-diol 150283-67-3 4-methyl-3-octene-1,5-diol 147028-43-1 5-methyl-3-octene-1,5-diol 19764-77-3 2,2-dimethyl-4,6-octadiene-1,3-diol 39824-01-6 2,6-dimethyl-4,7-octadiene-2,3-diol 51117-38-5 2,6-dimethyl-4,7-octadiene-2,6-diol 59076-71-0 7-Methyl-4-octene-1,6-diol 84538-24-9 2,7-bis(methylene)-4-octene-1,8-diol 109750-56-3 2-methylene-octene-1,8-diol 109750-58-5 2,7-dimethyl-5,7-octadiene-1,4-diol 105676-78-6 7-methyl-5,7-octadiene-1,4-diol 105676-80-0 5-Octene-1,3-diol 130272-38-7 7-methyl-6-octene-1,3-diol 110971-19-2 7-methyl-6-octene-1,4-diol 152715-87-2 6-Octene-1,5-diol 145623-79-6 7-methyl-6-octene-1,5-diol 116214-61-0 Z-methyl-6-octene-3,5-diol 65534-66-9 4-methyl-6-octene-3,5-diol 156414-25-4 2-methyl-7-octene-1,3-diol 155295-38-8 4-methyl-7-octene-1,3-diol 142459-25-4 7-methyl-7-octene-1,3-diol 132130-96-2 7-Octene-1,5-diol 7310-51-2 7-Octene-1,6-diol 159099-43-1 5-methyl-7-octene-1,6-diol 144880-56-8 2-Methyl-b-methylene-7-octene-2,4-diol 72446-81-2 7-methyl-7-octene-2,5-diol 152344-12-2 2-methyl-7-octene-3,5-diol 98753-85-6 1-nonene-3,5-diol 119554-56-2 1-nonene-3,7-diol 23866-97-9 3-nonene-2,5-diol 165746-84-9

• ·

Table 10 - continued, Unsaturated diols compound name Chemical Abstracts compound registration number (CAS No.) suitable saturated diols

8-methyl-4,6-nonadiene-1,3-diol 4-nonene-2,8-diol 6,8-nonadiene-1,5-diol

7-nonene-2,4-diol

8-nonene-2,4-diol

8-nonene-2,5-diol

124099-52-1

154600-80-3

108586-03-4

30625-41-3

119785-59-0

132381-58-9

1.9-decadiene-3,8-diol

1,9-decadiene-4,6-diol preferred saturated diols

2.2-Diallyl-1,3-butanediol

2-(1-ethyl-1-propenyl)-1,3-butanediol

2-(2-butenyl)-2-methyl-1,3-butanediol

2-(3-methyl-2-butenyl)-1,1-butanediol

2-Ethyl-2-(2-propenyl)-1,3-butanediol

2-methyl-2-(1-methyl-2-propenyl)-1,3-butanediol

2.3-Bis(1-methylethylidene)-1,4-butanediol

103984-04-9

138835-67-3

103985-49-5

116103-35-6

92207-83-5

98955-19-2

122761-93-7

141585-58-2

52127-63-6

1-Ethenyl-3-ethyl-1,3-pentanediol

2-ethenyl-4,4-dimethyl-1,3-pentanediol

3-methyl-2-(2-propenyl)-1,4-pentanediol 2-(1,1-dimethylethyl)-4-pentene-1,3-diol 2-ethyl-2,3-dimethyl-4-pentene-1 ,3-diol

104683-37-6

143447-08-9

139301-86-3

109788-04-7

90676-97-4

4-ethyl-2-methylene-1,4-hexanediol 2,3,5-trimethyl-1,5-hexadiene-3,4-diol 2-(1-methylethenyl)-1,5-hexanediol 4-ethenyl-2 ,5-dimethyl-2-hexene-1,5-diol

66950-87-6

18984-03-7

96802-18-5

70101-76-7

6-methyl-5-methylene-1,4-heptanediol 4,6-dimethyl-2,4-heptadiene-2,6-diol

100590-29-2

102605-95-8

Table 10 - continued, Unsaturated diols compound name Chemical Abstracts accession number (CAS No.) preferred saturated diols

2,5,5-trimethyl-2,6-heptadiene-1,4-diol

5.6-dimethyl-2-heptene-1,4-diol

4.6-dimethyl-3-heptene-1,5-diol

2.4-dimethyl-5-heptene-1,3-diol

3.6-dimethyl-5-heptene-1,3-diol

2.6-dimethyl-5-heptene-1,4-diol

3.6-dimethyl-5-heptene-1,4-diol

2,2-dimethyl-6-heptene-1,3-diol

5.6-dimethyl-6-heptene-1,4-diol

2.4-dimethyl-6-heptene-1,5-diol

2-ethylidene-6-methyl-6-heptene-1,5-diol

4-(2-Propenyl)-6-Heptene-2,4-diol

3-Ethenyl-1-octene-3,6-diol

2,7-dimethyl-2,4,6-octatriene-1,8-diol

2.6-dimethyl-2,3-octadiene-1,7-diol

3.7-dimethyl-2,5-octadiene-1,7-diol

3.7-dimethyl-2,6-octadiene-1,4-diol (Rosiridol)

2-methyl-2,6-octadiene-1,8-diol

3.7-dimethyl-2,7-octadiene-1,4-diol

2.6-dimethyl-2,7-octadiene-1,5-diol

2.6-dimethyl-2,7-octadiene-1,6-diol-(8-hydroxylinalool)

2.7-dimethyl-2,7-octadiene-1,6-diol

2-methyl-6-methylene-2-octene-1,7-diol

2.7-dimethyl-3,5-octadiene-2,7-diol

4-methylene-3,5-octanediol

1,6-dimethyl-3,7-octadiene-1,6-diol 2-methylene-4-octene-1,8-diol 2-methyl-6-octene-3,5-diol 4-methyl-6-octene -3,5-diol 2-methyl-6-methylene-7-octene-2,4-diol

115346-30-0

103867-76-1

147028-45-3

123363-69-9

96924-52-6

106777 98-4

106777 99-5

140192-39-8

152344-16-6

74231-27-9

91139-73-0

101536-75-8

65757-34-8

162648-63-7

91110-07-7

117935-59-8

101391-01-9

14912-02-7

91140-08-8

91140-09-9

103619-06-3

60250-14-8

91140-16-8

7177-18-6

143233-15-2

127446-19-1

109750-58-5

65534-66-9

156414-25-4

72446-81-2 • ·

Table 10 - continued, Unsaturated diols

compound name compound registration number in the journal Chemical Abstracts (CAS No.) preferred saturated diols 7-methyl-7-octene-2,5-diol 152344-12-2 2-methyl-7-octene-3,5-diol 98753-85-6 1-nonene-3,5-diol 119554-56-2 1-nonene-3,7-diol 23866-97-9 3-nonene-2,5-diol 165746-84-9 4-nonene-2,8-diol 154600-80-3 6,8-nonadiene-1,5-diol 108586-03-4 7-nonene-2,4-diol 30625-41-3 8-nonene-2,4-diol 119785-59-0 8-nonene-2,5-diol 131381-58-9 1,9-decadiene-3,8-diol 103984-04-9 1,9-decadiene-4,6-diol 138835-67-3

C ₁ - ₂ alcohols do not provide the clear and concentrated fabric softeners of this invention. Of the C ₃ alcohols, only n-propanol gives clear products, and these products retain their clarity at a temperature of 20 °C, or their clarity is restored when heated to temperatures above room temperature. However, the boiling point of this alcohol is too low. Of the C ₄ alcohols, only 2-butanol and 2-methyl-2-propanol have advantageous properties, but the boiling point of 2-methyl-2-propanol is too low. Alcohols C^_g, with the exception of the unsaturated acohols mentioned earlier and later, do not give clear preparations.

Certain primary solvents with two hydroxyl groups have been found to be suitable for the preparation of liquid concentrated, clear fabric softening compositions of the present invention. It was also surprisingly found that the suitability of different main solvents varies greatly depending on the number of carbon atoms, the structure of individual isomers with the same number of carbon atoms, the degree of unsaturation, and the like.

- 73 • ····

Major solvents with the same solubility as the aforementioned major solvents and with at least some degree of asymmetry are also preferred. A suitable main solvent has been found to have a ClogP of 0.15 to 0.64, preferably 0.25 to 0.62, more preferably 0.40 to 0.60.

For example, of the 1,2-alkanediol main solvents of the general formula HO-CH ₂ -CHOH-(CH ₂ ) _n -H, with an n value in the range of 1 to 8, there is only 1,2-hexanediol (n=4), which has a ClogP value of 0.53, i.e. a value lying within the suitable ClogP range of 0.15 to 0.64, is a good primary solvent for use in the present invention, while others, for example 1,2-propanediol,

1,2-butanediol, 1,2-pentanediol, 1,2-octanediol, 1,2-decanediol, with ClogP values outside the suitable range of 0.15 to 0.64, are not suitable solvents. Furthermore, of the isomers of hexanediol, 1,2-hexanediol is a good major solvent, while its isomers, such as 1,3-hexanediol, 1,6-hexanediol, 2,4-hexanediol, and

1,4-hexanediol, 1,5-hexanediol,

2,5-Hexanediol with ClogP values outside the range of 0.15 - 0.64 are not good primary solvents. This is illustrated by Examples and Comparative Examples 1-A and 1-B (see below). There are no C ₃ -C ₅ diols that would provide a clear concentrated formulation of the present invention.

Although there are many isomers of C8-diols which are suitable substances for use according to this invention, only those listed above and those listed below give clear products: 2,3-dimethyl-1,2-butanediol, 3,3-dimethyl-1,2-butanediol, 2-methyl-2,3-pentanediol, 3-methyl-2,3-pentanediol, 4-methyl-2,3-pentanediol, 2,3-hexanediol, 3, 4-Hexanediol, 2-ethyl-1,2-butanediol, 2-methyl-1,2-pentanediol, 3-methyl-1,2-pentanediol, 4-methyl-1,2-pentanediol, and 1,2-hexanediol . Of these, the most preferred are: 2-ethyl-1,2-butanediol, 2-methyl-1,2-pentanediol, 3-methyl-1,2-pentanediol, 4-methyl-1,2-pentanediol and 1,2- hexanediol.

There are several possible isomers of C ₇ ~diols, but only the following isomers are the preferred isomers, giving clear products: 2-butyl-1,3-butanediol, 2-propyl-1,4-butanediol,

2-ethyl-1,5-pentanediol, 2,3-dimethyl-2,3-pentanediol, 2,4-dimethyl-2,3-pentanediol, 4,4-dimethyl-2,3-pentanediol, 2,3- dimethylΊ4.

φφ φφ » « · « I φ·· φφφφ 4 Φ Φ « • · ΦΦ

-3,4-pentanediol, 2-methyl-1,6-hexanediol, 3-methyl-1,6-hexanediol,

1.3-heptanediol, 1,4-heptanediol, 1,5-heptanediol, 1,6-heptanediol.

Of these, the most preferred are: 2,3-dimethyl-2,3-pentanediol,

2.4-dimethyl-2,3-pentanediol, 3,4-dimethyl-2,3-pentanediol,

4.4-dimethyl-2,3-pentanediol, and 2,3-dimethyl-3,4-pentanediol. Similarly, there are even more C8-diol isomers, but only the following isomers are the preferred isomers giving clear products: 2-(1,1-dimethylpropyl)-1,3-propanediol, 2-(1,2-dimethylpropyl)-1,3 -propanediol, 2-(1-ethylpropyl)-1,3-propanediol,

2-(2,2-dimethylpropyl-1,3-propanediol, 2-ethyl-2-isopropyl-1,3-propanediol, 2-methyl-2-(1-methylpropyl-1,3-propanediol, 2-methyl- 2-(2-methylpropyl)-1,3-propanediol, 2-tert.butyl-2-methyl-1,3-propanediol, 2,2-diethyl-1,3-butanediol, 2-(1-methylpropyl)2 -butyl-1,3-butanediol, 2-ethyl-2,3-dimethyl 2-(1,1-dimethylethyl)-1,3-butanediol, 2-(2-methylpropyl)-1,3-butanediol, 2-methyl -2-propyl-1,3-butanediol,

2-methyl-2-isopropyl-1,3-butanediol, 3-methyl-2-propyl-1,3-butanediol, 2,2-diethyl-1,4-butanediol, 2-ethyl-2,3-dimethyl- 1,4-butanediol, 2-ethyl-3,3-dimethyl-1,4-butanediol, 2-(1,1-dimethylethyl)-1,4-butanediol, 3-methyl-2-isopropyl-1,4- butanediol, 2,2,3-trimethyl-1,3-pentanediol, 2,2,4-trimethyl-1,3-pentanediol,

2.3.4-trimethyl-1,3-pentanediol, 2,4,4-trimethyl-1,3-pentanediol,

-1,3-Butanediol, -1,3-Butanediol,

3.4.4-trimethyl-1,3-pentanediol,

2.2.4-trimethyl-1,4-pentanediol, 2,3,4-trimethyl-1,4-pentanediol, 2,2,3-trimethyl-1,5-pentanediol, 2,3,3-trimethyl-1, 5-pentanediol,

2.2.3 -1rimethyl-1,4-pentanediol,

2.3.3 -1rimethyl-1,4-pentanediol,

3.3.4 -1rimethyl-1,4-pentanediol,

2,2,4-trimethyl-1,5-pentanediol,

2.3.4-trimethyl-2,4-pentanediol,

2-ethyl-2-methyl-1,3-pentanediol, 2-ethyl-3-methyl-1,3-pentanediol, 2-ethyl-4-methyl-, 1,3-pentanediol, 3-ethyl-2-methyl -1,3-pentanediol, 2-ethyl-2-methyl-1,4-pentanediol, 2-ethyl-3-methyl -1,4-pentanediol, 2-ethyl-4-methyl-1,4-pentanediol, 3 -ethyl-3-methyl-1,5-pentanediol, 3-ethyl-2-methyl-2,4-pentanediol,

2-isopropyl-1,3-pentanediol, 2-propyl-1,3-pentanediol, 2-isopropyl-1,4-pentanediol, 2-propyl-1,4-pentanediol, 3-isopropyl-1,4-pentanediol, 3- propyl-2,4-pentanediol, 2,2-dimethyl-1,3-hexanediol, 2,3-dimethyl-1,3-hexanediol, 2,4-dimethyl-1,3-hexanediol,

2.5-dimethyl-1,3-hexanediol, 3,4-dimethyl-1,3-hexanediol, 3,5-di» ♦ · « » «to· ··« « ' • · « • to ·» • to * to* methyl-1,3-hexanediol, 4,4-dimethyl-1,3-hexanediol, 4,5-dimethyl-1,3-hexanediol, -1,4-hexanediol, -1,4-hexanediol, -1 ,4-hexanediol, -1,4-hexanediol, -1,5-hexanediol, -1,5-hexanediol, -1,5-hexanediol, -1,5-hexanediol, -2,6-hexanediol,

2.3- dimethyl2,5-dimethyl3.4- dimethyl4.5- dimethyl2.2- dimethyl2.4- dimethyl3.3- dimethyl3.5- dimethyl3,3-dimethyl2.2- dimethyl-1,4-hexanediol,

2.4-dimethyl-1,4-hexanediol,

3.3-dimethyl-1,4-hexanediol,

3.5-dimethyl-1,4-hexanediol,

5.5-dimethyl-1,4-hexanediol,

2.3-dimethyl-1,5-hexanediol,

2.5-dimethyl-1,5-hexanediol,

3.4-dimethyl-1,5-hexanediol,

4.5-dimethyl-1,5-hexanediol,

2-ethyl-1,3-hexanediol, 4-ethyl-1,3-hexanediol,

2-ethyl-1,4-hexanediol, 4-ethyl-1,4-hexanediol, 2-ethyl-1,5-hexanediol, 3-ethyl-2,4-hexanediol, 4-ethyl-2,4-hexanediol, 3-ethyl-2,5-hexanediol, 2-methyl-1,3-heptanediol, 3-methyl-1,3-heptanediol, 4-methyl-1,3-heptanediol, 5-methyl-1,3-heptanediol, 6-methyl-1,3-heptanediol, 2-methyl-1,4-heptanediol, 3-methyl-1,4-heptanediol, 4-methyl-1,4-heptanediol, 5-methyl-1,4-heptanediol, 6-methyl-1,4-heptanediol, 2-methyl-1,5-heptanediol, 3-methyl-1,5-heptanediol, 4-methyl-1,5-heptanediol, 5-methyl-1,5-heptanediol, 6-methyl-1,5-heptanediol, 2-methyl-1,6-heptanediol, 3-methyl-1,6-heptanediol, 4-methyl-1,6-heptanediol, 5-methyl-1,6-heptanediol, 6-methyl-1,6-heptanediol, 2-methyl-2,4-heptanediol, 3-methyl-2,4-heptanediol, 4-methyl-2,4-heptanediol, 5-methyl-2,4-heptanediol, 6-methyl-2,4-heptanediol, 2-methyl-2,5-heptanediol, 3-methyl-2,5-heptanediol, 4-methyl-2,5-heptanediol, 5-methyl-2,5-heptanediol, 6-methyl-2,5-heptanediol, 2-methyl-2,6-heptanediol,

3-methyl-2,6-heptanediol, 4-methyl-2,6-heptanediol, 3-methyl-3,4-heptanediol, 2-methyl-3,5-heptanediol, 4-methyl-3,5-heptanediol, 2,4-octanediol, 2,5-octanediol, 2,6-octanediol, 2,7-octanediol, 3,5-octanediol, and/or 3,6-octanediol, of which more preferred are: 2-(1, 1-dimethylpropyl)-1,3-propanediol, 2-(1,2-dimethylpropyl)-1,3-propanediol, 2-(1-ethylpropyl)-1,3-propanediol, 2-(2,2-dimethylpropyl) -1,3-propanediol, 2-ethyl-2-isopropyl-1,3-propanediol, 2-methyl-2-(1-methylpropyl)-1,3-propanediol,

2-methyl-2-(2-methylpropyl)-1,3-propanediol, 2-tert-butyl-2-methyl-1,3-propanediol, 2 -(1-methylpropyl)-1,3-butanediol, 2 -(2-methylpropyl)-1,3-butanediol, 2-butyl-1,3-butanediol, 2-methyl»flfl

-76-.

• ·· ·♦ ·» flflfl · · flfl · • fl · · · · • flfl flflfl fl · fl flfl flflfl • fl flflfl flflflfl flfl ··

-2-propyl-1,3-butanediol, 3-methyl-2-propyl-1,3-butanediol,

2.2-diethyl-1,4-butanediol, 2-ethyl-2,3-dimethyl-1,4-butanediol,

2- ethyl-3,3-dimethyl-1,4-butanediol, 2-(1,1-dimethylethyl)-1,4-butanediol, 2,3,4-trimethyl-1,3-pentanediol, 2,2, 3-trimethyl-1,5-pentanediol, 2,2,4-trimethyl-1,5-pentanediol, 2,3,3-trimethyl-1,5-pentanediol, 2-ethyl-2-methyl-1,3- pentanediol, 2-ethyl-3-methyl-1,3-pentanediol, 2-ethyl-4-methyl-1,3-pentanediol,

3-ethyl-2-methyl-1,3-pentanediol, 2-ethyl-2-methyl-1,4-pentanediol, 2-ethyl-3-methyl-1,4-pentanediol, 2-ethyl-4-methyl- 1,4-pentanediol, 3-ethyl-3-methyl-1,5-pentanediol, 3-ethyl-2-methyl-2,4-pentanediol, 2-isopropyl-1,3-pentanediol, 2-propyl-1, 3-pentanediol, 2-isopropyl-1,4-pentanediol, 2-propyl-1,4-pentanediol,

3-isopropyl-1,4-pentanediol, 3-propyl-2,4-pentanediol, 2,2-dimethyl-1,3-hexanediol, 2,3-dimethyl-1,3-hexanediol, 2,4-dimethyl- 1,3-hexanediol, 2,5-dimethyl-1,3-hexanediol, 3,4-dimethyl-1,3-hexanediol, 3,5-dimethyl-1,3-hexanediol, 4,4-dimethyl-1, 3-hexanediol,

4.5-dimethyl-1,3-hexanediol, 2,2-dimethyl-1,4-hexanediol, 2,3-dimethyl-1,4-hexanediol, 2,4-dimethyl-1,4-hexanediol, 2,5- dimethyl-1,4-hexanediol, 3,3-dimethyl-1,4-hexanediol, 3,4-dimethyl-1,4-hexanediol, 3,5-dimethyl-1,4-hexanediol, 4,5-dimethyl- 1,4-hexanediol,

5.5-dimethyl-1,4-hexanediol, 2,2-dimethyl-1,5-hexanediol, 2,3-dimethyl-1,5-hexanediol, 2,4-dimethyl-1,5-hexanediol, 2,5- dimethyl-1,5-hexanediol, 3,3-dimethyl-1,5-hexanediol, 3,4-dimethyl-1,5-hexanediol, 3,5-dimethyl-1,5-hexanediol, 4,5-dimethyl- 1,5-hexanediol,

3.3-dimethyl-2,6-hexanediol, 2-ethyl-1,3-hexanediol, 4-ethyl-1,3-hexanediol, 2-ethyl-1,4-hexanediol, 4-ethyl-1,4-hexanediol,

2-ethyl-1,5-hexanediol, 3-ethyl-2,4-hexanediol, 4-ethyl-2,4-hexanediol, 3-ethyl-2,5-hexanediol, 2-methyl-1,3-heptanediol, 3-methyl-1,3-heptanediol, 4-methyl-1,3-heptanediol, 5-methyl-1,3-heptanediol, 6-methyl-1,3-heptanediol, 2-methyl-1,4-heptanediol, 3-methyl-1,4-heptanediol, 4-methyl-1,4-heptanediol, 5-methyl-1,4-heptanediol, 6-methyl-1,4-heptanediol, 2-methyl-1,5-heptanediol,

3-methyl-1,5-heptanediol, 4-methyl-1,5-heptanediol, 5-methyl-1,5-heptanediol, 6-methyl-1,5-heptanediol, 2-methyl-1,6- heptanediol, 3-methyl-1,6-heptanediol, 4-methyl-1,6-heptanediol, 5-methyl-1,6-heptanediol, 6-methyl-1,6-heptanediol, 2-methyl-2,4- heptanediol, 3-methyl-2,4-heptanediol, 4-methyl-2,4-heptanediol,

99 99 99

9 9 9 9 9 ·

9 9 9 99

9 9 999 9 9

9 9 9 9

999 9999 99 99

9

5-methyl-2,4-heptanediol, 6-methyl-2,4-heptanediol, 2-methyl-2,5-heptanediol, 3-methyl-2,5-heptanediol, 4-methyl-2,5-heptanediol, 5-methyl-2,5-heptanediol, 6-methyl-2,5-heptanediol, 2-methyl-2,6-heptanediol, 3-methyl-2,6-heptanediol, 4-methyl-2,6-heptanediol, 3-methyl-3,4-heptanediol, 2-methyl-3,5-heptanediol, 4-methyl-3,5-heptanediol, 2,4-octanediol, 2,5-octanediol, 2,6-octanediol, 2, 7-octanediol, 3,5-octanediol and/or 3,6-octanediol.

Preferred mixtures of 1,3 diols with eight carbon atoms can be prepared by condensing a mixture of butyraldehyde, isobutyraldehyde and/or methyl ethyl ketone (2-butanone) containing at least two of these reactants in the presence of highly alkaline catalysts and following! by hydrogenation to form a mixture of 1,3-diols with eight carbon atoms containing 2,2,4-trimethyl-1,3-pentanediol, 2-ethyl-1,3-hexanediol, 2,2-dimethyl-1,3-hexanediol, 2-ethyl-4-methyl-1,3-pentanediol, 2-ethyl-3-methyl-1,3-pentanediol, 3,5-octanediol,

2,2-dimethyl-2,4-hexanediol, 2-methyl-3,5-heptanediol and/or

3-methyl-3,5-heptanediol, with 2,2,4-trimethyl-1,3-pentanediol forming less than half of the mixture, together with other isomers occurring in smaller quantities, resulting from condensation on the methylene group of 2-butanone, is if present, buy them instead of using metal.

The ability to easily mix with other components of the preparation and other properties such as fragrance, fluidity, melting point lowering and the like can be improved by polyalkylation of some non-preferred C _g - ₈ diols listed in Tables 2 to 6. Certain C ₃ - ₅ alkylated diols are also preferred. Preferred alkylated derivatives of the above C ₃ _ ₈ diols are listed in the following text, in which the abbreviations used have the following meanings: [EO means means - (CH ₂ CH ₂ O) _n H, Me-En means by methyl end groups means 2Me-E " groups, PO means polyethoxy derivatives, En polyethoxy derivatives with - (CH ₂ CH ₂ O) _n CH ₃ , 2(Me-E _n ) polypropoxyderiates, -(CH(CH ₃ )CH ₂ O) _n H BO means polybutyleneoxy groups, (CH (CH ₂ CH ₃ )CH ₂ O) _n H, and n-BO means poly(n-butyleneoxy) group -(CH ₂ CH ₂ CH ₂ CH ₂ O) _n H]. Said preferred alkylated derivatives of the above Cg_g diols are the following substances including:

1. 1,2-propanediol (C3) 2(Me-E- _L _ ₄ ), 1,2-propanediol (C3) P0 ₄ ,

2-methyl-1,2-propanediol (C4) (Me-E ₄ _ ₁₀ ), 2-methyl-1,2-propanediol (C4) 2 (Me-E-j_) , 2-methyl-1, 2- propanediol (C4) P0 ₃ , 2-methyl-1,2-propanediol (C4) BOj, 1,3-propanediol (C3) 2(Μβ-Εθ_θ),

1,3-propanediol (C3) PO ₅ _g,

of 2,2-diethyl-1,3-propanediol (C7) E ₁ _ _? , 2,2-diethyl-1,3-propanediol (C7) PO-p 2,2-diethyl

1,3-propane-diol (C7) n-BO ₁ _ ₂ ,

2,2-dimethyl-1,3-propanediol (C5) 2(Me-E-j__ ₂ ), 2,2-dimethyl-1,3-propanediol (C5) PO ₃ _ ₄ ,

2-(1-methylpropyl)-1,3-propanediol (C7) E-j__ ₇ , 2-(1-methylpropyl)-1,3-propanediol (C7) PO-^, 2-(1-methylpropyl)-1 ,3-propanediol, (C7) n-BO ₁ _ ₂ , 2-(2-methylpropyl)-1,3-propanediol (C7) E ₁ _ ₇ , 2-(2-methylpropyl)-1,3-propanediol ( C7) P0 _lø 2-(2-methylpropyl)-1,3-propanediol (C7) n-BO ₁ _ ₂ , 2-ethyl-1,3-propanediol (C5) (Me ^E g_ ₁₀ ), 2-ethyl- of 1,3-propanediol (C5)2(Me E^),

2-ethyl-1,3-propanediol (C5) P0 ₃ , 2-ethyl-2-methyl-1,3-propanediol (C6) (Me-E ₁ _g), 2-ethyl-2-methyl-1,3 -propanediol (C6) P0 ₂ ,

2-ethyl-2-methyl-1,3-propanediol (C6) B0 _lø 2-isopropyl-1,3-propanediol (C6) (Me E-j__g) , 2-isopropyl-1,3-propanediol (C6) P0 ₂ ,

2-isopropyl-1,3-propanediol (C6) B0 _lø 2-methyl-1,3-propanediol (C4) 2(Me-E ₂ _ ₅ ), 2-methyl-1,3-propanediol (C4) PO ₄ _ ₅ ,

2-methyl-1,3-propanediol (C4) B0 ₂ , 2-methyl-2-isopropyl-1,3-propanediol (C7) E ₂ _ ₉ , 2-methyl-2-isopropyl-1,3-propanediol ( C7) PO of 2-methyl-2-isopropyl-1,3-propanediol (C7) n-BO-j__ ₃ ,

2-methyl-2-propyl-1,3-propanediol (C7) E- _L _ ₇ , 2-methyl-2-propyl-1,3-propanediol (C7) P0 _lz 2-methyl-2-propyl-1, 3-propanediol (C7) n-BO ₁ _ ₂ , 2-propyl-1,3-propanediol (C6) (Me-E ₁ _ ₄ ),

2- propyl-1,3-propanediol (C6) P0 ₂ . 2-propyl-1,3-propanediol (C6) B0 _i;

2. 1,2-butanediol (C4) (Me Ε ₂ _θ), 1,2-butanediol (C4) PO ₂ _ ₃ ,

1.2-butanediol (C4) B0 _lø 2,3-dimethyl-1,2-butanediol, (C6) E-^g,

2.3- dimethyl-1,2-butanediol (C6) n-BO ₁ _ ₂ , 2-ethyl-1,2-butanediol (C6) El-3, 2-ethyl-1,2-butanediol (C6) n-BO _lø 2-methyl-1,2-butanediol (C5) (MeE _1-5 ), 2-methyl-1,2-butanediol (C5) Ρ0 ₄ ,

3.3-dimethyl-1,2-butanediol (C6) E-j__g, 3-dimethyl-1,2-butanediol (C6) n-BO ₁ _ ₂ , 3-methyl-1,2-butanediol (C5) (MeE ₁ _ ₂ ),

3-methyl-1,2-butanediol (C5) P0 _lø 1,3-butanediol (C4) 2(MeE ₃ _g),

1.3-butanediol (C4) P0 ₅ , 1,3-butanediol (C4) B0 ₂ , 2,2,3-trimethyl-1,3-butanediol (C7) (MeEl-3), 2,2,3-trimethyl- 1,3-butane• ·· ·· ·· ·« « · · · · · • · · · ·« « · t ··· · · • · · · · ··· ···· ** ·· ·· • · ·· • · « • · ·· diol (C7) P0 ₁ _ ₂ , 2,2-dimethyl-1,3-butanediol (C6) (MeE ₃ _ _g ),

2,2-dimethyl-1,3-butanediol (C6) P0 ₃ , 2,3-dimethyl-1,3-butanediol (C6) (MeE ₃ _ ₈ ), 3-dimethyl-1,3-butanediol (C6) P0 ₃ ,

2-ethyl-1,3-butanediol, (C6) (MeE ₁ _ _g ), 2-ethyl-1,3-butanediol (C6) PO ₂ _ ₃ , 2-ethyl-1,3-butanediol (C6) B0 _lz 2-ethyl-2-methyl-1,3-butanediol (C7) (MeE-^), 2-ethyl-2-methyl-1,3-butanediol (C7) PO^, 2-ethyl-2-methyl- 1,3-butanediol (C7) n-B0 ₂ _ ₄ ,

2-ethyl-3-methyl-1,3-butanediol (C7) (MeE-|_) , 2-ethyl-3-methyl-1,3-butanediol (C7) P0 _lz 1,3-butanediol (C7) n -BO ₂ _ ₄ , 2-isopropyl-1 , 3-butanediol (C7) (MeE-^ , 2-isopropyl-1,3-butanediol (C7) PO-^, 2-isopropyl-1,3-butanediol (C7 ) n-BO ₂ _ ₄ , 2-methyl-1,3-butanediol (C5) 2(MeEl-3), 2-methyl-1,3-butanediol (C5) P0 ₄ , 2-propyl-1,3- of butanediol (C7) E ₂ _ _g , 2-propyl-1,3-butanediol (C7) P0 ₄ , 2-propyl-1,3-butanediol (C7) n-BO ₄ _ ₃ ,

3-methyl-1,3-butanediol (C5) 2(MeE ₁ _ ₃ ), 3-methyl-1,3-butanediol (C5) P0 ₄ , 1,4-butanediol (C4) 2(MeE ₂ _ ₄ ) , 1,4-butanediol (C4) PO ₄ _ ₅ , 1,4-butanediol (C4) B0 ₂ , 2,2,3-trimethyl-1,4-butanediol (C7) E ₂ _ _g , 2,2, 3-trimethyl-1,4-butanediol (C7) PO-j.,

2,2,3-trimethyl-1,4-butanediol (C7) η-ΒΟ ₄ _ ₃ , 2,2-dimethyl-1,4-butanediol (C6) (MeE ₁ _ _g ), 2,2-dimethyl- 1,4-butanediol (C6) P0 ₂ , 2,2-dimethyl-1,4-butanediol (C6) BO-p 2,3-dimethyl-1,4-butanediol (C6) (MeE ₁ _ _g ), 2 ,3-dimethyl-1,4-butanediol (C6) P0 ₂ , 2,3-dimethyl-1,4-butanediol (C6) B0 _lz 2-ethyl-1,4-butanediol (C6) (MeE- _L _ ₄ ), 2-ethyl-1, 4-butanediol (C6) P0 ₂ ,

2-ethyl-1,4-butanediol (C6) BOj, 2-ethyl-2-methyl-1,4-butanediol (C7) E-|__7, 2-ethyl-2-methyl-1,4-butanediol (C7 ) PO-^,

2-ethyl-2-methyl-1,4-butanediol (C7) n-BO ₁ _ ₂ , 2-ethyl-3-methyl -1, 4-butanediol (C7) Ε-^γ, 2-ethyl-3- methyl-1,4-butanediol (C7) P0 _lz 2-ethyl-3-methyl-1,4-butanediol (C7) n-BO ₁ _ ₂ ,

2-isopropyl-1,4-butanediol (C7) E- _L _ ₇ , 2 - isopropyl-1,4-butanediol (C7) P0 _lz 2-isopropyl-1,4-butanediol (C7) n-BO ₁ _ ₂ , 2-methyl-1,4-butanediol (C5) (MeE _g . -1(Ρ ² -methyl-1,4-butanediol (C5) 2 (MeE-jth , 2-methyl-1,4-butanediol (C5 ) P0 ₃ , 2-methyl-1,4-butanediol (C5) BO-j_, 2-propyl-1,4-butanediol (C7) Ε _1-5 , 2-propyl-1,4-butanediol (C7) η -ΒΟ-|__ ₂ , 3-ethyl-1-methyl-1,4-butanediol (C7) E ₂ _ ₉ , 3-ethyl-1-methyl-1,4-butanediol (C7) PO-j_, 3- of ethyl-1-methyl-1,4-butanediol (C7) n-BO ₁ _ ₃ , 2,3-butanedio80 • ftft • ftftft · • ·· • ft ftft • ftft • ftft ftft · • ···» ·· ·· ft ftft · • ftftft ft ftftft · · • · · ftft ftft lu (C4) (MeEg_ ₁₀ ), 2,3-butanediol (C4) 2(Me EJ , 2,3-butanediol (C4) PO ₃ _ ₄ , 2,3-butanediol (C4) BO _lz 2,3-dimethyl-2,3-butanediol (C6) E ₃ _ _g , 2,3-dimethyl-2,3-butanediol (C6) PO _lz 2-methyl- 2,3-butanediol (C5) (Me ^E 1-5^' 2-methyl-2,3-butanediol (C5) PC>2 from 2-methyl-2,3-butanediol (C5) BO-j_ ;

3. 1,2-pentanediol (C5) Ε ₃ _ ₄ θ, 1,2-pentanediol (C5) PO^,

1.2-pentanediol (C5) n-BO ₂ _ ₃ , 2-methyl-1,2-pentanediol (C6) E ₁ _ ₃ , 2-methyl-1,2-pentanediol (C6) η-BOp 2-methyl-1 ,2-pentanediol (C6) BO _lz 3-methyl-1,2-pentanediol (C6) Ε ₄ _ ₃ , 3-methyl-1,2-pentanediol (C6) n-BOp 4-methyl-1,2-pentanediol (C6) E ₁ _ ₃ , 4-methyl-1,2-pentanediol (C6) n-BO _lz 1,3-pentanediol (C5) 2(Me-E ₁ _ ₂ ), 1,3-pentanediol (C5) PO ₃ _ ₄ , 2,2-dimethyl-1,3-pentanediol (C7) (Me-E ₄ ), 2,2-dimethyl-1,3-pentanediol (C7) PO _lz 2,2-dimethyl-1, of 3-pentanediol (C7) n-B0 ₂ _ ₄ ,

2.3-dimethyl-1,3-pentanediol (C7) (Me-EJ , 2,3-dimethyl-1,3-pentanediol (C7) PO ₄ , 2,3-dimethyl-1,3-pentanediol (C7) n- BO ₂ _ ₄ ,

2.4-dimethyl-1,3-pentanediol (C7) (Me-E^) 2,4-dimethyl-1,3-pentanediol (C7) POp 2,4-dimethyl-1,3-pentanediol (C7) n-BO ₂ _ ₄ , 2-ethyl-1,3-pentanediol (C7) ^E 2-9' 1,3-pentanediol (C7) Ρ ₄ , Ú2-ethyl-1,3-pentanediol (C7) n-B0 ₁ _ ₃ , 2-methyl-1,3-pentanediol (C6) 2(Me-E ₁ _g), 2-methyl-1,3-pentanediol (C6) PO ₂ _ ₃ , 2-methyl-1,3-pentanediol (C6 ) BO-j_, 3,4-dimethyl-1,3-pentanediol (C7) (Me-EJ , 3,4-dimethyl-1,3-pentanediol (C7)POp

3.4-dimethyl-1,3-pentanediol (C7) n-BO ₂ _ ₄ , 3-methyl-1,3-pentanediol (C6) (Me-Epg) 3-methyl-1,3-pentanediol (C6) PO ₂ _ ₃ 3-methyl-1,3-pentanediol (C6) BOp 4,4-dimethyl-1,3-pentanediol (C7) (Me-E-j_) , 4,4-dimethyl-1,3-pentanediol (C7 ) POp 4,4-dimethyl-1,3-pentanediol (C7) n-B0 ₂ _ ₄ , 4-methyl-1,3-pentanediol (C6) (Me-Epg) , 4-methyl-1,3-pentanediol (C6) PO ₂ _ ₃ , 4-methyl-1,3-pentanediol (C6) BOp 1,4-pentanediol (C5) 2(Me-E ₁ _ ₂ ),

1.4-pentanediol (C5) PO ₃ _ ₄ , 2,2-dimethyl-1,4-pentanediol (C7) (Me-E^), 2,2-dimethyl-1,4-pentanediol (C7) POp 2,2 -dimethyl-1,4-pentanediol (C7) n-BO ₂ _ ₄ , 2,3-dimethyl-1,4-pentanediol (C7) (Me-E-j_) , 2,3-dimethyl-1,4- pentanediol (C7) POp 2,3-dimethyl-1,4-pentanediol (C7) n-BO ₂ _ ₄ , 2,4-dimethyl-1,4-pentanediol (C7) (Me-E ₄ ), 2,4 -dimethyl-1,4-pentanediol (C7) POp

2.4-dimethyl-1,4-pentanediol (C7) n-BO ₂ _ ₄ , 2-methyl-1,4-pentane81

9999

9 9

9 9 9 9 • 99 9 9 9

99 diol (C6) (Me-E ₁ _ ₆ ),

2-methyl-1,4-pentanediol (C6) PO ₂ _ ₃ ,

2- methyl-1,4-pentanediol (C6) B0 _lø 3,3-dimethyl-1,4-pentanediol (C7) (Me-E-jJ , 3,3-dimethyl-1,4-pentanediol (C7) PO -p 3,3-dimethyl-1,4-pentanediol (C7) n-BO ₂ _ ₄ , 3,4-dimethyl-1,4-pentanediol (C7) (Me-E-jJ , 3,4-dimethyl- 1,4-pentanediol (C7) PO _1# 3,4dimethyl-1,4-pentanediol (C7) n-BO ₂ _ ₄ , 3-methyl-1,4-pentanediol (C6) 2(Me-E ₁ _g) , 3-methyl-1,4-pentanediol (C6) PO ₂ _ ₃ , 3-methyl-1,4-pentanediol (C6) B0 _lø 4-methyl-1,4-pentanediol (C6) 2(Me-E ₁ _ ₆ ), 4-methyl-1,4-pentanediol (C6) PO ₂ _ ₃ ,

4-methyl-1,4-pentanediol (C6) BO-p 1,5-pentanediol (C5) (Me-E ₄ _ ₁₀ ), 1,5-pentanediol (C5) 2(Me-Ej), 1,5 -pentanediol (C5) P0 ₃ , 2,2-dimethyl-1,5-pentanediol (C7) Ε _χ _ ₇ ,

1,5-pentanediol, 2,2-dimethyl-(C7) POp 2,2-dimethyl-1,5-pentanediol (C7) n-BO-p ₂ , 2,3-dimethyl-1,5-pentanediol (C7 ) E-j__ ₇ ,

2.3-dimethyl-1,5-pentanediol (C7) POp 2,3-dimethyl-1,5-pentanediol (C7) n-BO ₁ _ ₂ , 2,4-dimethyl-1,5-pentanediol (C7) Ep ₇ ,

2.4-dimethyl-1,5-pentanediol (C7) POp 2,4-dimethyl-1,5-pentanediol (C7) n-BO ₁ _ ₂ , 2-ethyl-1,5-pentanediol (C7) E-pg, 2-ethyl-1,5-pentanediol (C7) n-BO ₁ _ ₂ , 2-methyl-1,5-pentanediol (C6) (Me-E ₁ _ ₄ ), 2-methyl-1,5-pentanediol ( C6) P0 ₂ , 3,3-dimethyl-1,5-pentanediol (C7) Ε _χ _ ₇ , 3,3-dimethyl-1,5-pentanediol (C7) POp 3,3-dimethyl-1,5-pentanediol (C7)n-BO _{- L_2} ,

3-methyl-1,5-pentanediol (C6) (Me-E ₁ _ ₄ ), 3-methyl-1,5-pentanediol (C6) P0 ₂ , 2,3-pentanediol (C5) (Me-El-3 ), 2,3-pentanediol (C5) P0 ₂ , 2-methyl-2,3-pentanediol (C6) Ep ₇ , 2-methyl-2,3-pentanediol (C6) POp 2-methyl-2,3-pentanediol (C6) n-BO-p ₂ , 3-methyl-2,3-pentanediol (C6) E-j__ ₇ , 3-methyl-2,3-pentanediol (C6) PO^. 3-methyl-2,3-pentanediol (C6) n-BO ₁ _ ₂ ,

4-methyl-2,3-pentanediol (C6) Ep ₇ , 4-methyl-2,3-pentanediol (C6) PO-p 4-methyl-2,3-pentanediol (C6) n-BO ₁ _ ₂ , 2 ,4-pentanediol (C5) 2(Me-E _x _ ₄ ), 2,4-pentanediol (C5) P0 ₄ , 2,3-dimethyl-2,4-pentanediol (C7) (Me-E ₁ _ ₄ , 2,3-dimethyl-2,4-pentanediol (C7) P0 ₂ , 2,4-dimethyl-2,4-pentanediol (C7) (Me-E ₁ _ ₄ ),

2.4-dimethyl-2,4-pentanediol (C7) P0 ₂ , 2-methyl-2,4-pentanediol (C7) (Μθ-Ε ₅ _ ₁ θ), 2-methyl-2,4-pentanediol (C7) PO ₃ , 3,3-dimethyl-2,4-pentanediol (C7) (Me-E- _L _ ₄ ) , 3,3-dimethyl-2,4-pentanediol, (C7) P0 ₂ , 3-methyl-2, 4-pentanediol (C6) (Me-Eg_ ₁₀ ),

• ·· ·· ♦♦

- .

3-methyl-2,4-pentanediol (C6) P0 ₃ ;

4. 1,3-hexanediol (C6) (Me-E- _L _ ₅ ), 1,3-hexanediol (C6) P0 ₂ ,

1,3-hexanediol (C6) BO-p 2-methyl-1,3-hexanediol (C7) E ₂ _ _g ,

2- methyl-1,3-hexanediol (C7) Ρ0 _χ , 2-methyl-1,3-hexanediol (C7) n-BO ₁ _ ₃ , 2-methyl-1,3-hexanediol (C7) BO-ρ 3 -methyl-1,3-hexanediol (C7) E ₂ _ _g , 3-methyl-1,3-hexanediol (C7) POj,

3-methyl-1,3-hexanediol (C7) n-BO-p ₃ , 4-methyl-1,3-hexanediol (C7) E ₂ _ _g , 4-methyl-1,3-hexanediol (C7) P0 _lz 4-methyl-1,3-hexanediol (C7) n-BO- _L _ ₃ , 5-methyl-1,3-hexanediol (C7) E ₂ _ _g ,

5-methyl-1,3-hexanediol (C7) P0 _lz 5-methyl-1,3-hexanediol (C7) n-BO ₁ _ ₃ , 1,4-hexanediol (C6) (Me-E ₁ _ ₅ ), 1,4-hexanediol (C6) P0 ₂ , 1,4-hexanediol (C6) BO-p 2-methyl-1,4-hexanediol (C7) E ₂ _ _g , 2-methyl-1,4-hexanediol (C7 ) PO-p 2-methyl-1,4-hexanediol (C7) n-BO-]__ ₃ , 3-methyl-1,4-hexanediol (C7) E ₂ _ _g , 3-methyl-1,4-hexanediol (C7) PO-p 3-methyl-1,4-hexanediol (C7) n-BO ₁ _ ₃ , 4-methyl-1,4-hexanediol (C7) E ₂ _ _g , 4-methyl-1,4- of hexanediol (C7) PO-ρ 4-methyl-1, 4-hexanediol, (C7) n-BO- _L _ ₃ ,

5-methyl-1,4-hexanediol (C7) E ₂ _ _g , 5-methyl-1,4-hexanediol (C7) PO-p 5-methyl-1, 4-hexanediol (C7) n-BO-p ₃ , 1,5-hexanediol (C6) (Me-E ₁ _ ₅ ), 1,5-hexanediol (C6) P0 ₂ 1,5-hexanediol (C6) BO-p 2-methyl-1,5-hexanediol (C7 ) E ₂ _ _g , 2-methyl-1,5-hexanediol (C7) PO-p 2-methyl-1, 5-hexanediol (C7) n-BO-p ₃ ,

3-methyl-1,5-hexanediol (C7) E ₂ _ _g , 3-methyl-1,5-hexanediol (C ₇ ) PO-p 3-methyl-1,5-hexanediol (C7) n-BO ₁ _ ₃ , 4-methyl-1,5-hexanediol (C7) E ₂ _ _g , 4-methyl-1,5-hexanediol (C7) PO-ρ

4- methyl-1,5-hexanediol (C7) n-BO ₁ _ ₃ , 5-methyl-1,5-hexanediol (C7) E ₂ _ _g , 5-methyl-1,5-hexanediol (C7) PO- p 5-methyl-1,5-hexanediol (C7) n-BO _{- L_3} , 1,6-hexanediol (C6) (Me- _E - _{L_2} ) ,

1,6-hexanediol (C6) PO-p ₂ , 1,6-hexanediol (C6) n-BO ₄ , 2-methyl-1,6-hexanediol (C7) E-j__ ₅ , 2-methyl-1, 6 -hexanediol (C7) n-BO ₁ _ ₂ , 3-methyl-1,6-hexanediol (C7) E- _L _ ₅ , 3-methyl-1,6-hexanedi-

hello (C7) n-BO ₁ _ ₂ , of 2,3-hexanediol (C6) E-pipe 2,3-hexanedi- hello (C6) n-BO-j_, of 2,3-hexanediol (C6) BO-p 2,4-hexanedi- hello (C6) (Me-E ₃ . ₈ ), of 2,4-hexanediol (C6) PC > ₃ , 2-methyl-2,4-hexane-

diol (C7) (Me-E ₁ _ ₂ ), 2-methyl-2,4-hexanediol (C7) P0 ₁ _ ₂ , 3-methyl-2,4-hexanediol (C7) (Me-E ₁ _ ₂ ) , 3-methyl-2,4-hexanediol (C7) P0 ₁ _ ₁ , 4-methyl-2,4-hexanediol (C7) (Me-E ₁ _ ₂ ), 4-meth··

9 9

9 • 99 «9

9 9 9 9 9 9 • 9 9999 • 9999999

9 9 9 9

999 9999 99 99 hyl-2,4-hexanediol (C7) P0 ₁ _ ₂ , 5-methyl-2,4-hexanediol (C7) (Me-E ₁ _ ₂ ), 5-methyl-2,4-hexanediol ( C7) P0 ₁ _ ₂ , 2,5-hexanediol (C6) (Me-E ₃ _ ₈ ), 2,5-hexanediol (C6) P0 ₃ , 2-methyl-2,5-hexanediol (C7) (Me- E ₁ _ ₂ ), 2-methyl-2,5-hexanediol (C7) P0 ₁ _ ₂ , 3-methyl-2,5-hexanediol (C7) (Me-E ₁ _ ₂ ), 3-methyl-2, 5-hexanediol (C7) P0 ₁ _ ₂ , 3,4-hexanediol (C6) E0- _L _ ₅ ,

3,4-Hexanediol (C6) n-BO-p 3,4-Hexanediol (C6) BO-p

5. 1,3-heptanediol (C7) Ep ₇ , 1,3-heptanediol (C7) P0 _lø

1.3-heptanediol (C7) n-BO ₁ _ ₂ , 1,4-heptanediol (C7) E ₁ _ ₇ ,

1.4-heptanediol (C7) PO-p 1,4-heptanediol (C7) n-BO ₁ _ ₂ ,

1,5-heptanediol (C7) E ₁ _ ₇ , 1,5-heptanediol (C7) PO-p

1.5-heptanediol (C7) n-BO ₁ _ ₂ , 1,6-heptanediol (C7) Ε _1-7 ,

1.6-heptanediol (C7) POp 1,6-heptanediol (C7) n-BO-p ₂ ,

1.7-heptanediol (C7) E ₄ _ ₂ , 1,7-heptanediol (C7) n-BOp

2,4-heptanediol (C7) ^E 3_ _1Q , 2,4-heptanediol (C7) (Me-EJ ,

2.4-heptanediol (C7) POp 2,4-heptanediol (07) n-BO ₃ ,

2.5-heptanediol (C7) E ₃ _ _1Q , 2,5-heptanediol (C7) (Me-E-jJ ,

2.5-heptanediol (C7) PO-p 2,5-heptanediol (C7) n-BO ₃ ,

2.6-heptanediol (07) E ₃ _ _1Q , 2,6-heptanediol (C7) (Me-E-jJ ,

2,6-heptanediol (C7) PO-p 2,6-heptanediol (C7) n-BO ₃ ,

3,5-heptanediol (C7) Ε ₃ _ ₁₀ , 3,5-heptanediol (C7) (Me-Ej),

3,5-heptanediol (C7) PO-^ 3,5-heptanediol (C7) n-BO ₃ ;

6. 3-methyl-2-isopropyl-1,3-butanediol (C8) PO-ρ 2,3,3-trimethyl-2,4-pentanediol (C8) POp 2,2-diethyl-1,3-butanediol ( C8) E ₂ _ ₅ , 2,3-dimethyl-2,4-hexanediol (C8) E ₂ _ ₅ , 2,4-dimethyl-2,4-hexanediol (C8) E ₂ _ ₈ , 2,5-dimethyl -2,4-hexanediol (C8) E ₂ _ ₅ , 3,3-dimethyl-2,4-hexanediol (C8) E ₂ _ ₅ , 3,4-dimethyl-2,4-hexanediol (08) E ₂ _ ₅ , 3,5-dimethyl-2,4-hexanediol (C8) E ₂ _ ₈ , 4,5-dimethyl-2,4-hexanediol (C8) E ₂ _^, 5,5-dimethyl-2,4- of hexanediol (C8) E ₂ _ ₅ , 2,3-dimethyl-2,5-hexanediol (C8) E ₂ _ ₅ , 2,4-dimethyl-2,5-hexanediol (C8) E ₂ _ ₅ , 2,5 -dimethyl-2,5-hexanediol (C8) E ₂ _ ₅ , 3,3-dimethyl-2,5-hexanediol (C8) E ₂ _ ₅ , 3,4-dimethyl-2,5-hexanediol (C8) E ₂ _ ₅ , 3-methyl-3,5-heptanediol (C8) E ₂ _ ₅ , 2,2-diethyl-1,3-butanediol (C8) n-BO ₁ _ ₂ , 2,3-dimethyl-2, of 4-hexanediol (C8) n-BO _{- L_2} ,

2,4-dimethyl-2,4-hexanediol (C8) n-BO ₁ _ ₂ , 2,5-dimethyl-2,4-hexanediol (C8) n-BO- ₄ _ ₂ , 3,3-dimethyl-2 ,4-hexanediol (C8) n-BO-p ₂ ,

A A > «

And A

- .

A· AA * A A A • A AA

AAAA A « A A

A A A A

3.4-dimethyl-2,4-hexanediol (C8) n-BO ₁ _ ₂ , 3,5-dimethyl-2,4-hexanediol, (C8) n-BO ₁ _ ₂ , 4,5-dimethyl-2,4 -hexanediol (C8) n-BO-^^,

5.5-dimethyl-2,4-hexanediol n-BO ₁ _ ₂ , 2,3-dimethyl-2,5-hexanediol (C8) n-BO ₁ _ ₂ , 2,5-dimethyl-2,5-hexanediol (C8 ) n-BO ₁ _ ₂ ,

2.5-dimethyl-2,5-hexanediol (C8) η-ΒΟ-]__ ₂ , 3,3-dimethyl-2,5-hexanediol (C8) n-BO ₁ _ ₂ , 3,4-dimethyl-2,5 -hexanediol (C8) n-BO _{- L_2} ,

3-methyl-3,5-heptanediol (C8) n-BO-j__ ₂ , 2-(1,2-dimethylpropyl)-1,3-propanediol (C8) n-BO^, 2-ethyl-2,3- dimethyl-1,3-butanediol, (C8) n-BO-p 2-methyl-2-isopropyl-1,3-butanediol (C8) η-ΒΟ-ρ 3-methyl-2-isopropyl-1,4-butanediol (C8) n-BO-p 2,2,3-trimethyl-1,3-pentanediol (C8) n-BO-p 2,2,4-trimethyl-1,3-pentanediol (C8) n-BO-p of 2,4,4-trimethyl-1,3-pentanediol (C8) η-ΒΟ-ρ

3.4.4- trimethyl-1,3-pentanediol (C8) n-BO-p 2,2,3-trimethyl-1,4-pentanediol, (C8) n-BO-p 2,2,4-trimethyl-1 ,4-pentanediol (C8)n-BO-p 2,3,3-trimethyl-1,4-pentanediol (C8)n-BO^,

2.3.4- trimethyl-1,4-pentanediol (08) n-BO-p 3,3,4-trimethyl-1,4-pentanediol, (08) n-BO-p 2,3,4-trimethyl-2 ,4-pentanediol (08) n-BO-p 4-ethyl-2,4-hexanediol (08) n-BO-p 2-methyl-2,4-heptanediol (C8) n-BO-p 3-methyl- 2,4-heptanediol (C8) n-BO, 4-methyl-2,4-heptanediol (C8) n-BO-p 5-methyl-2,4-heptanediol (C8) n-BO-p 6-methyl- 2,4-heptanediol (08) n-BO-p 2-methyl-2,5-heptanediol (08) n-BO-p 3-methyl-2,5-heptanediol (C8) n-BO-p 4-methyl -2,5-heptanediol (C8) η-ΒΟ-ρ 5-methyl-2,5-heptanediol (C8) η-ΒΟ-ρ 6-methyl-2,5-heptanediol (C8) n-BO-p 2- methyl-2,6-heptanediol (C8) n-BO-p 3-methyl-2,6-heptanediol (C8) n-BO-p 4-methyl-2,6-heptanediol (C8) n-BO-p 2 -methyl-3,5-heptanediol (C8) n-BO-p 2-(1,2-dimethylpropyl)-1,3-propanediol (08) E- _L _ ₃ , 2-ethyl-2,3-dimethyl- l, 3-butanediol (C8) E ₁ _ ₃ ,

2-methyl-2-isopropyl-1,3-butanediol (08) E _1-3 , 3-methyl-2-isopropyl-1,4-butanediol (C8) Ep ₃ , 2,2,3-trimethyl-1, 3-pentanediol (08) E _1-3 , 2,2,4-trimethyl-1,3-pentanediol (08) E ₁ _ ₃ ,

2.4.4-trimethyl-1,3-pentanediol (08) E-j__ ₃ , 3,4,4-trimethyl-1,3-pentanediol (C8) E-j__ ₃ , 2,2,3-trimethyl-1, 4-pentanediol (C8) E _1-3 , 2,2,4-trimethyl-1,4-pentanediol (C8) E ₁ _ ₃ ,

2,3,3-trimethyl-1,4-pentanediol (C8) Ε _1-3 , 2,3,4-trimethyl-1,4-pentanediol (C8) Ε-|__ ₃ , 3,3,4-trimethyl -1, 4-pentanediol (08) E-|__ _3/ 2,3,4-trimethyl-2,4-pentanediol (08) E ₁ _ ₃ , • ·· ·· · · • ·· • · ♦ ♦ • · · ··· ·· • ·· ·· · · • · • · • · ··· ···· • · · · • · ·· ··· · · • · ·

9·99

4-ethyl-2,4-hexanediol (C8) E-j__ ₃ , 2-methyl-2,4-heptanediol (C8) E ₁ _ ₃ , 3-methyl-2,4-heptanediol (C8) Ε _1-3 , 4-methyl-2,4-heptanediol (C8) E ₁ _ ₃ , 5-methyl-2,4-heptanediol (C8) E _1-3 ,

6-methyl-2,4-heptanediol (C8) E ₁ _ ₃ , 2-methyl-2,5-heptanediol (C8) E ₁ _ ₃ , 3-methyl-2,5-heptanediol (C8) E ₁ _ ₃ , 4-methyl-2,5-heptanediol, (C8) E _1-3 , 5-methyl-2,5-heptanediol (C8) E ₁ _ ₃ ,

6-methyl-2,5-heptanediol (C8) E-|__ ₃ , 2-methyl-2,6-heptanediol (C8) E- _l _ ₃ , 3-methyl-2,6-heptanediol (C8) E ₁ _ ₃ , 4-methyl-2,6-heptanediol (C8) E-j__ ₃ and/or 2-methyl-3,5-heptanediol (C8) E ₁ _ ₃ ; and

7. their mixture.

Of the nonane isomers, only isomer is particularly preferred

2,3,3,4-tetramethyl-2,4-pentadiol. In addition to the aliphatic diol main solvents and some of their alkylated derivatives which have been mentioned earlier and will be mentioned later, certain other diol ethers have also been found to be suitable as main solvents for the preparation of liquid concentrated clear fabric softening compositions of the present invention. As with aliphatic diol-based main solvents, it has been found that the suitability of each main solvent varies from case to case and depends, for example, on the number of carbon atoms in a particular diol ether molecule. For example, it is clear from Table 6 that of the glyceryl ethers of the general formula HOCH ₂ -CHOH-CH ₂ -0-R, where R is alkyl C2 to C8, only monopentyl ethers HOCH ₂ -CHOH-CH ₂ -OC ₅ H ₁₁ (3 -pentyloxy-1,2-propanediols) with various isomeric pentyl groups ^c 5 ^H ii' have a ClogP value in the preferred range of ClogP values of 0.25 to 0.62 and are suitable for the preparation of liquid concentrated, clear fabric softeners according to the present invention. This is illustrated by Examples and Comparative Examples XXXIIA-7 through XXXIIA-7F. It has also been found that the cyclohexyl derivative is suitable, but the cyclopentyl derivative is not. A similar selectivity is manifested in the selection of aryl glyceryl ethers. Despite the existence of various possible aromatic groups, only a few phenol derivatives have suitable properties. Equally narrow selectivity was also found for dihydroxyalkyl ethers. Bis(2-hydroxybutyl) ether was found to be suitable, but bis(2-hydroxypentyl) ether was not.

• · • · ··· · · · · · · ·· ·· 9 9 9 9999 9

9 9 9 9 9 9 9

999 99 9999999 99 99

- 86 Of the dicyclic hydroxyalkyl analogues, bis(2-hydroxycyclopentyl)ether is suitable, but bis(2-hydroxycyclohexyl)ether is not. Non-limiting examples of synthetic methods for the preparation of some preferred dihydroxyalkyl ethers are given below.

Butyl monoglyceryl ether (3-butyloxy-1,2-propanediol) is not very suitable for the preparation of liquid concentrated clear plasticizers according to this invention. However, its polyethoxy derivatives, preferably triethoxy derivatives to nonethoxy derivatives, more preferably pentaethoxy derivatives to octaethoxy derivatives, are suitable main solvents listed in Table 6.

All identified preferred alkyl glyceryl ethers and/or di(hydroxyalkyl) ethers are listed in Table 6, of which the most preferred are: 3-(n-pentyloxy)-1,2-propanediol, 3-(2-pentyloxy)-1,2 -propanediol, 3 -(3-pentyloxy)-1,2-propanediol, 3-(2-methyl -1-butyloxy)-1,2-propanediol, 3-(iso-amyloxy)-1,2-propanediol, 3 -(3-methyl-2-butyloxy)-1,2-propanediol, 3-(cyclohexyloxy)-1,2-propanediol, 3-(1-cyclohexyl-1-ethyloxy)-1,2-propanediol,

2-(pentyloxy)-1,3-propanediol, 2-(2-pentyloxy)-1,3-propanediol,

2-(3-pentyloxy)-1,3-propanediol, 2-(2-methyl-1-butyloxy)-1,3-propanediol, 2-(iso-amyloxy)-1,3-propanediol, 2-(3 -methyl-2-butyloxy)-1,3-propanediol, 2-(cyclohexyloxy)-1,3-propanediol,

2-(1-cyclohexy-1-ethyloxy)-1,3-propanediol, pentaethoxylated

3-(Butyloxy)-1,2-propanediol, hexaethoxylated 3-(butyloxy)-1,2-propanediol, heptaethoxylated 3-(butyloxy)-1,2-propanediol, octaethoxylated 3-(butyloxy)-1,2-propanediol , nonethoxylated 3-(butyloxy)-1,2-propanediol, monopropoxylated 3-(butyloxy)-1,2-propanediol, dibutyleneoxylated 3-(butyloxy)-1,2-propanediol, and/or tributyleneoxylated 3-(butyloxy)- 1,2-propanediol. Preferred aromatic glyceryl ethers are: 3-phenyloxy-1,2-propanediol, 3-benzyloxy-1,2-propanediol, 3-(2-phenylethyloxy)-1,2-propanediol, 1,2-propanediol, 2-(m- cresyloxy)-1,3-propanediol, 2-(p-cresyloxy)-1,3-propanediol, 2-benzyloxy-1,3-propanediol, 2-(2-phenyethyloxy)-1,3-propanediol and mixtures thereof. More preferred aromatic glyceryl ethers are: 3-phenyloxy-1,2-propanediol, 3-benzyloxy-1,2-propanediol, 3-(2-phenylethyloxy)-1,2-propanediol, 2-(m-cresyloxy)-1, 2-propanediol, 2-(p-cresyloxy)-1,3-propanediol, 2-(2-phenylethyloxy)-1,3-propanediol, • · · · ( • · « • · · · and mixtures thereof. Most preferred di(hydroxyalkyl) ethers are bis(2-hydroxybutyl) ether and bis(2-hydroxycyclopentyl ether).

An illustrative and non-limiting example of a synthetic method for the preparation of preferred alkyl and aryl monoglyceryl ethers is provided below.

Preferred alicyclic diols and their derivatives are: 1) saturated diols and their derivatives including: 1-isopropyl-1,2-cyclobutanediol, 3-ethyl-4-methyl-1,2-cyclobutanediol, 3-propyl-1,2-cyclobutanediol , 3-isopropyl-1,2-cyclobutanediol, 1-ethyl-1,2-cyclopentanediol, 1,2-dimethyl-1,2-cyclopentanediol, 1,4-dimethyl-1,2-cyclopentanediol, 2,4,5 -trimethyl-1,3-cyclopentanediol, 3,3-dimethyl-1,2-cyclopentanediol,

3,4-dimethyl-1,2-cyclopentanediol, 3,5-dimethyl-1,2-cyclopentanediol, 3-ethyl-1,2-cyclopentanediol, 4,4-dimethyl-1,2-cyclopentanediol, 4-ethyl- 1,2-cyclopentanediol, 1,1-bis(hydroxymethyl)cyclohexane, 1,2-bis(hydroxymethyl)cyclohexane, 2-dimethyl-1,3-cyclohexanediol, 1,3-bis(hydroxymethyl)cyclohexane, 1,3- dimethyl-1,3-cyclohexanediol, 1,6-dimethyl-1,3-cyclohexanediol,

of 1-hydroxy-cyclohexaneethanol, 1-hydroxy-cyclohexanemethanol, 1-ethyl-1,3-cyclohexanediol, 1-methyl-1,2-cyclohexanediol,

2,2-dimethyl-1,3-cyclohexanediol, 2,3-dimethyl-1,4-cyclohexanediol, 2,4-dimethyl-1,3-cyclohexanediol, 2,5-dimethyl-1,3-cyclohexanediol, 2, 6-dimethyl-1,4-cyclohexanediol, 2-ethyl-1,3-cyclohexanediol, 2-hydroxycyclohexaneethanol, 2-hydroxyethyl-1-cyclohexanol, 2-hydroxymethylcyclohexanol, 3-hydroxyethyl-1-cyclohexanol, 3-hydroxycyclohexaneethanol, 3- hydroxymethylcyclohexanol, 3-methyl-1,2-cyclohexanediol, 4,4-dimethyl-1,3-cyclohexanediol, 4,5-dimethyl-1,3-cyclohexanediol, 4,6-dimethyl-1,3-cyclohexanediol, 4- ethyl-1,3-cyclohexanediol, 4-hydroxyethyl-1-cyclohexanol, 4-hydroxymethylcyclohexanol, 4-methyl-1,2-cyclohexanediol, 5,5-dimethyl-1,3-cyclohexanediol, 5-ethyl-1,3- cyclohexanediol, 1,2-cycloheptanediol, 2-methyl-1,3-cycloheptanediol,

2-methyl-1,4-cycloheptanediol,

5-methyl-1,3-cycloheptanediol,

6-methyl-1,4-cycloheptanediol, octanediol, 1,5-cyclooctanediol,

4-methyl-1,3-cycloheptanediol,

5-methyl-1,4-cycloheptanediol, 1,3-cyclooctanediol, 1,4-cyclodiethoxylate 1,2-cyclohexanediol, triethoxylate 1,2-cyclohexanediol, tetraethoxylate

1,2-cyclohexanediol, 1,2-cyclohexanediol pentaethoxylate, 1,2-cyclohexanediol hexaethoxylate, 1,2-cyclohexanediol heptaethoxylate, 1,2-cyclohexanediol octaethoxylate, nonaethoxylate

1,2-cyclohexanediol, 1,2-cyclohexanediol monopropoxylate, 1,2-cyclohexanediol monobutyleneoxylate, 1,2-cyclohexanediol dibutyleneoxylate and/or 1,2-cyclohexanediol tributyleneoxylate. The most preferred saturated alicyclic diols and their derivatives are: 1-isopropyl-1,2-cyclobutanediol, 3-ethyl-4-methyl-1,2-cyclobutanediol, 3-propyl-1,2-cyclobutanediol, 3-isopropyl-1-ethyl- 1,2-cyclopentanediol, 1,2-dimethyl1,4-dimethyl-1,2-cyclopentanediol, 3,3-di-1,2-cyclobutanediol, -1,2-cyclopentanediol, methyl-1,2-cyclopentanediol, 3 ,4-dimethyl-1,2-cyclopentanediol,

3,5-dimethyl-1,2-cyclopentanediol,

4,4-dimethyl-1,2-cyclopentanediol,

1.1-bis(hydroxymethyl)cyclohexane, hexane, 1,2-dimethyl-1,3-cyclohexanediol, 1,3-bis(hydroxytmethyl)cyclohexane, 1-hydroxy-cyclohexanemethano1, 1-methyl-1,2-cyclohexanediol, 3- hydroxymethylcyclohexanol, 3-methyl-1,2-cyclohexanediol, 4,4-dimethyl-1,3-cyclohexanediol, 4,5-dimethyl-1,3-cyclohexanediol, 4,6-dimethyl-1,3-cyclohexanediol, 4- ethyl-1,3-cyclohexanediol, 4-hydroxyethyl-1-cyclohexanol, 4-hydroxymethylcyclohexanol, 4-methyl-1,2-cyclohexanediol, 1,2-cycloheptanediol, 1,2-cyclohexanediol pentaethoxylate, 1,2-cyclohexanediol hexaethoxylate, 1,2-cyclohexanediol heptaethoxylate, octaethoxylate

1.2-cyclohexanediol, 1,2-cyclohexanediol nonethoxylate, 1,2-cyclohexanediol monopropoxylate, and/or dibutylene oxylate

of 1.2-cyclohexanediol.

Preferred aromatic diols are 1-phenyl-1,2-ethanediol,

1-phenyl-1,2-propanediol, 2-phenyl-1,2-propanediol, 3-phenyl-1,2-propanediol, 1-(3-methylphenyl)-1,3-propanediol, 1-(4-methylphenyl) )-1,3-propanediol, 2-methyl-1-phenyl-1,3-propanediol, 1-phenyl-1,3-butanediol, 3-phenyl-1,3-butanediol and/or 1-phenyl-1, 4-Butanediol. Of these, 1-phenyl-1,2-propanediol is most preferred,

2-phenyl-1,2-propanediol, 3-phenyl-1,2-propanediol, 1-(3-methylphenyl)-1,3-propanediol, 1-(4-methylphenyl)-1,3-propanediol, 2- methyl-1-phenyl-1,3-propanediol and/or 1-phenyl-1,4-butanediol.

As mentioned earlier, all unsaturated compounds,

3-ethyl-1,2-cyclopentanediol, 4-ethyl-1,2-cyclopentanediol, 1,2-bis(hydroxymethyl)cyclo-

which differ from the preferred major solvents by having an additional CH ₂ group are also preferred major solvents. Preferred unsaturated diols suitable for use as main solvents are, however, in particular:

2.2- diallyl-1,3-butanediol, 2-(1-ethyl-1-popenyl)-1,3-butanediol,

-(2-butenyl)-2-methyl-1,3-butanediol, 2-(3-methyl-2-butenyl)-1,3-butanediol, 2-ethyl-2-(2-propenyl)-1,3 -butanediol, 2-methyl-2-(1-methyl-2-propenyl)-1,3-butanediol, 2,3-bis(1-methylethylidene)-1,4-butanediol, 2-ethenyl-3-ethyl- 1,3-pentanediol, 2-ethenyl-4,4-dimethylethyl)-1,3-pentanediol, 3-methyl-2-(2-propenyl)-1,4-pentanediol, 2-(1,1-dimethyl- 4-pentene-1,3-diol, 2-ethyl-2,3-dimethyl-4-pentene-1,3-diol, 4-ethyl-2-methylene-1,4-hexanediol, 2,3,5- trimethyl-1,5-hexadiene-3,4-diol, 2-(1-methylethenyl-1,5-hexanediol, 4-ethenyl-2,5-dimethyl-2-hexene-1,5-diol, 6-methyl -5-methylene-1,4-heptanediol, 4,6-dimethyl-2,4-heptadiene-2,6-diol, 2,5,5-trimethyl-2,6-heptadiene-1,4-diol, 5 ,6-dimethyl-2-heptane-1,4-diol, 4,6-dimethyl-3-heptene-1,5-diol, 2,4-dimethyl-5-heptene-1,3-diol, 3,6 -dimethyl-5-heptene-1,3-diol, 2,6-dimethyl-5-heptene-1,4-diol, 3,6-dimethyl-5-heptene-1,4-diol,

2.2-dimethyl-6-heptene-1,3-diol, 5,6-dimethyl-6-heptene-1,4-diol,

2,4-dimethyl-6-heptene-1,5-diol, 2-ethylidene-6-methyl-6-heptene-1,5-diol, 4-(2-propenyl)-6-heptene-2,4- diol, 3-ethenyl-1-octene-3,6-diol, 2,7-dimethyl-2,4,6-octatriene-1,8-diol, 2,6-dimethyl-2,5-octadiene-1, 7-diol, 3,7-dimethyl-2,5-octadiene-1,7-diol, 3,7-dimethyl-2,6-octadiene-1,4-diol, (Rosiridol); 2-methyl-2,6-octadiene-1,8-diol, 3,7-dimethyl-2,7-octadiene-1,4-diol,

2,6-dimethyl-2,7-octadiene-1,5-diol, 2,6-dimethyl-(8-hydroxylinalool), 2,7-octadiene-1,6-diol, 2,7-dimethyl-2, 7-octadiene-1,6-diol, 2-methyl-6-methylene-2-octene-1,7-diol, 2,7-dimethyl-3,5-octadiene-2,7-diol, 4-methylene- 3,5-octanediol, 2,6-dimethyl-3,7-octadiene-1,6-diol, 2-methylene-4-octene-1,8-diol, 2-methyl-6-octene-3,5- diol,4-methyl-6-octene-3,5-diol, 2-methyl-6-methylene-7-octene-2,4-diol, 7-methyl-7-octene-2,5-diol, 2- methyl 7-octene-3,5-diol, 1-nonene-3,5-diol; 1-nonene-3,7-diol, 3-nonene-2,5-diol, 4-nonene-2,8-diol, 6,8-nonadiene-1,5-diol, 7-nonene-2,4- diol, 8-nonene-2,4-diol: 8-nonene-2,5-diol, 1,9-decadiene-3,8-diol and/or 1,9-decadiene-4,6-diol.

• · *· use as consisting of

Alcohols suitable for use as main solvents may also be advantageously selected from the group consisting of 2,5-dimethyl-2,5-hexanediol, 2-ethyl-1,3-hexanediol, 2-methyl-2-propyl-1,3 -propanediol, 1,2-hexanediol and their mixtures.

More preferably, alcohols suitable for use as main solvents may be selected from the group consisting of 2-ethyl-1,3-hexanediol, 2-methyl-2-propyl-1,3-propanediol, 1,2-hexanediol and mixtures thereof. Even more preferably, alcohols suitable for the main solvents can be selected from the group of 2-ethyl-1,3-hexanediol, 1,2-hexanediol and mixtures thereof.

If several derivatives of the same diol with different alkyleneoxy groups can be used, for example a derivative of 2-methyl-2,3-butanediol with 3 to 5 ethyleneoxy groups, or with 2 propyleneoxy groups, or with one butyleneoxy group, it is preferable to use the derivative with the lowest number of groups, i.e. in this case a derivative with one butyleneoxy group. However, if the presence of only one to four ethyleneoxy groups is necessary to achieve good properties of the preparation, this option is also advantageous.

Unsaturated diols condition that this one methylene added CH ₂ group of adjacent carbons,

Surprisingly, it has been found that there is a clear similarity between the suitability of diols and their unsaturated homologues or analogues with higher molecular weights for the preparation of the substances of this invention. These unsaturated homologues or analogues are as suitable as the corresponding saturated main solvents, except that the unsaturated main solvents have an additional group (CH ₂ -group) for each double bond. In other words, there is an obvious addition rule according to which there are, for each suitable saturated main solvent of the present invention, which enables the preparation of a clear concentrated fabric softening preparation, suitable main solvents in which the number of CH ₂ groups is greater by one such group or more such groups, while the number of hydrogen atoms on each is reduced to allow the formation of a double bond • · • <

carbon-carbon. Thus, the number of hydrogen atoms in the molecule is constant with respect to the corresponding saturated main solvent. This effect is due to the surprising fact that the addition of one -CH ₂ ~ group to a solvent molecule increases its ClogP value by 0.53, while the loss of two neighboring hydrogen atoms associated with the formation of a double bond causes a decrease in the ClogP value by approximately the same value, namely a value of 0.48, which compensates for the addition of the -CH ₂ - group. This allows a transition from a suitable saturated main solvent to its suitable unsaturated analogue/homologue of higher molecular weight, containing at least one more carbon atom in such a way that one double bond is added for each -CH ₂ - group added, thus maintaining the overall number of hydrogen atoms the same as in the corresponding saturated main solvent, while the ClogP value of this new solvent remains within the desired range of 0.15-0.64. Next, we present some illustrative examples. 2,2-Dimethyl-6-heptene-1,3-diol (CAS No. 140192-39-8) is a C9-diol that is a suitable major solvent and can be considered either as a derivative formed by the addition of one CH ₂ group and of one double bond to one of these suitable major solvents which are C8-diols: 2-methyl-1,3-heptanediol or 2,2-dimethyl-1,3-hexanediol.

2,4-dimethyl-5-heptene-1,3-diol (CAS No. 123363-69-9) is a C9-diol that is a suitable major solvent and can be considered as a derivative formed by the addition of one CH ₂ group and one double bonds to one of the following suitable major solvents, which are C8-diols: 2-methyl-1,3-heptanediol or

2,4-dimethyl-1,3-hexanediol.

2-(1-ethyl-1-propenyl)-1,3-butanediol (CAS No. 116103-35-6) is a C9-diol that is a suitable major solvent and can be considered as a derivative formed by the addition of one CH ₂ group and one double bond to one of the following suitable major solvents which are C8-diols: 2-(1-ethylpropyl)-1,3-propanediol or 2-(1-methylpropyl)-1,3-butanediol.

2-ethenyl-3-ethyl-1,3-pentanediol (CAS No. 104683-37-6) is a C9-diol that is a suitable major solvent and can be considered as a derivative formed by the addition of one CH ₂ group and one

99 · · · • · »

" · ··« ···· double bonds to one of the following suitable major solvents, which are C8-diols: 3-ethyl-2-methyl-1,3-pentanediol or 2-ethyl-3-methyl-1,3 -pentanediol.

3.6-dimethyl-5-heptene-1,4-diol (e.g. CAS No. 106777-99-5) is a C9-diol that is a suitable main solvent and can be considered as a derivative formed by the addition of one CH ₂ group and one double bonds to one of the following suitable major solvents, which are C8-diols: 3-methyl-1,4-heptanediol, 6-methyl-1,4-heptanediol, or 3,5-dimethyl-1,4-hexanediol.

5.6-dimethyl-6-heptene-1,4-diol (e.g. CAS No. 152344-16-6) is a C9-diol that is a suitable main solvent and can be considered as a derivative formed by the addition of one CH ₂ group and one double bonds to one of the following suitable major solvents which are C8-diols: 5-methyl-1,4-heptanediol, 6-methyl-1,4-heptanediol or 4,5-dimethyl-1,3-hexanediol,

4-Methyl-6-octene-3,5-diol (CAS No. 156414-25-4) is a C9-diol that is a suitable major solvent and can be considered as a derivative formed by the addition of one CH ₂ group and one double bond to one of the following suitable major solvents which are C8-diols: 3,5-octanediol, 3-methyl-2,4-heptanediol or 4-methyl-3,5-heptanediol.

Rosiridol (CAS No. 101391-01-9) and isorosiridol (CAS No. 149252-15-3) are two isomers of 3,7-dimethyl-2,6-octadiene-1,4-diol, and are ClO-diols, which are suitable major solvents, and may be considered as a derivative formed by the addition of two CH ₂ groups and two double bonds to one of these suitable major solvents, which are C8-diols: 2-methyl-1,3-heptanediol, 6-methyl- 1,3-heptanediol; 6-methyl-1,3-heptanediol, 3-methyl-1,4-heptanediol, 6-methyl-1,4-heptanediol,

2,5-dimethyl-1,3-hexanediol or 3,5-dimethyl-1,4-hexanediol. 8-Hydroxylinalool (CAS No. 103619-06-3, 2,6-dimethyl-2,7-octadiene-1,6-diol) is a CIO-diol which is a suitable main solvent and can be considered as a derivative formed by the addition of two CH ₂ groups and two double bonds to one of the following suitable major solvents, which are C8-diols: 2-methyl-1,5-heptanediol, 5-methyl-1,5-heptanediol, 2-methyl-1,6- heptanediol, 6-methyl-1,6-heptanediol or 2,4-dimethyl-1,4• · • ·

-hexanediol.

2,7-dimethyl-3,7-octadiene-2,5-diol (CAS No. 171436-39-8) is ClO-diol, which is a suitable main solvent, and can be considered as a derivative formed by the addition of two CH ₂ groups and two double bonds to one of the following suitable major solvents, which are C8-diols: 2,5-octanediol,

6-methyl-1,4-heptanediol, 2-methyl-2,4-heptanediol, 6-methyl-2,4-heptanediol, 2-methyl-2,5-heptanediol, 6-methyl-2,5-heptanediol and 2,5-dimethyl-2,4-hexanediol. 4-Butyl-2-butene-1,4-diol (CAS No. 153943-66-9) is a C8-diol that is a suitable major solvent and can be considered as a derivative formed by the addition of one CH ₂ group and one double bond to one of the following suitable primary solvents which are C7-diols: 2-propyl-1,4-butanediol or 2-butyl-1,3-propanediol.

Analogously, there are cases where the higher molecular weight unsaturated homologue that is derived from an unsuitable saturated solvent is also not a suitable solvent itself. So, for example, 3,5-dimethyl-5-hexene-2,4-diol (e.g. CAS

No. 160429-40-3) is an unsuitable unsaturated C8 solvent which may be considered a derivative of these unsuitable saturated C7 solvents: 3-methyl-2,4-hexanediol, 5-methyl-2,4-hexanediol or 2,4- dimethyl-1,3-pentanediol. Similarly, 2,6-dimethyl-5-heptene-1,2-diol (e.g., CAS No. 141505-71-7) is an unsuitable C9 unsaturated solvent that can be considered a derivative of these unsuitable C8 saturated solvents: 2-methyl- 1,2-heptanediol, 6-methyl-1,2-heptanediol, 2,5-dimethyl-1,2-hexanediol. Surprisingly, it was found that there is one exception to the above rule in which saturated solvents always have equally suitable unsaturated analogues or homologues. This exception applies to diol main solvents with two hydroxyl groups on two adjacent carbon atoms. In some cases, but not always, the insertion of one or two CH ₂ groups between two adjacent hydroxyl groups of an unsuitable solvent group yields an unsaturated homologue with a weight more suitable for a concentrated fabric softener, unsaturated 6,6-dimethyl-1-heptene -3,5-diol (CAS no higher molecular weight preparation of clear So for example 109788-01-4),

000· • •00 • 0 ·· « which is a suitable main solvent, and which has no adjacent hydroxyl groups, may be considered a derivative of the unsuitable 2,2-dimethyl-3,4-hexanediol, in whose molecule there are adjacent hydroxyl groups. In this case, however, it is more convenient to consider 6,6-dimethyl-1-heptene-3,5-diol as a derivative of either 2-methyl-3,5-heptanediol or 5,5-dimethyl-2,4-hexanediol, which are both are suitable major solvents and do not have adjacent hydroxyl groups. It follows that by inserting a CH ₂ group between adjacent hydroxyl groups of a suitable main solvent, an unsaturated diol of higher molecular weight can be obtained, which is not a suitable solvent. Thus, for example, the inappropriate unsaturated 2,4-dimethyl-5-hexene-2,4-diol (CAS No. 87604-24-8), which has no adjacent hydroxyl groups, may be considered a derivative of the appropriate 2,3-dimethyl-2, 3-pentanediol, in whose molecule there are adjacent hydroxyl groups. In this case, however, it is more convenient to consider the inappropriate unsaturated 2,4-dimethyl-5-hexene-2,4-diol as a derivative of either 2-methyl-2,4-hexanediol or 4-methyl-2,4-hexanediol, both of which unsuitable solvents and do not have adjacent hydroxyl groups. There are also cases where an inappropriate unsaturated solvent containing no adjacent hydroxyl groups can be considered a derivative of an inappropriate solvent with adjacent hydroxyl groups, as in the case of the pair 4,5-dimethyl-6-hexene-1,3-diol and 3,4-dimethyl -1,2-pentanediol. Therefore, in order to be able to judge the suitability of an unsaturated solvent that does not contain adjacent hydroxyl groups, it is necessary to base it on the properties of the low-molecular saturated homologs, which also do not contain adjacent hydroxyl groups. This leads to the general conclusion that the reliability of the respective relationship is higher if the distance of the hydroxyl groups is the same in both cases. Therefore, in order to be able to judge the values of unsaturated homologues with adjacent hydroxyl groups of higher molecular weight, it is necessary to start from a saturated solvent, in whose molecule adjacent hydroxyl groups are also found.

It has been found that clear, stable, low-viscosity fabric softeners with a surprisingly low content of • to to · can be obtained by using the main alcohol solvents listed above.

-95-.

• to • to · · · * • · « ·« • · 9 · « 9 9 • tototo ••toto ·· ·· of the main solvents, i.e. with a concentration of these solvents lower than 40 wt.%. It has also been found that by using alcohol as the main solvent, highly concentrated fabric softener formulations can be obtained which are stable and can be diluted, for example in a ratio of 2:1 to 10:1, to give formulations with a lower concentration of fabric softener which are yet stable. As mentioned earlier, it is desirable that the concentration of the main solvent be as low as possible so that the compositions of the present invention are transparent or clear. The presence of water has a significant effect on the ability of the main solvent to achieve the clarity of these preparations. The higher the water content, the higher the concentration of the main solvent (relative to the concentration of the plasticizer) required to make the product clear. On the contrary, the lower the concentration of water, the lower the concentration of the main solvent (in relation to the concentration of the plasticizer) is needed. At low water concentrations of 5 to 15% by weight, the weight ratio of the fabric softener active agent to the main solvent is preferably 55:45 to 85:15, more preferably 60:40 to 80:20. At water concentrations in the range of 15 wt.% to 70 wt.%, the ratio of the active substance of the fabric softener to the main

solvent with advantage in range 45:55 up to 70:30, more advantageous in range 55 :45 until 70:30. At high water concentrations in range 70 until 80 %, Yippee ratio active substances of the preparation for softening fabrics to the main solvent preferably in the range

30:70 to 55:45, more preferably in the range of 35:65 to 45:55. At even higher concentrations of water, the concentration of the softener to the main solvent needs to be even higher. It is particularly preferred to use mixtures of the above major solvents, since one of the problems associated with large amounts of solvents is safety. The use of mixtures reduces the amount of any material used. Both odor and flammability can also be minimized by using mixtures, especially if one of the main solvents is volatile and/or has a strong odor, which is more likely with low molecular weight substances. Suitable solvents that can be used at concentrations not sufficient to obtain a clear product are

00 »· · · ·

0 0 ·

0 0

2,2,4-trimethyl-1,3-pentanediol, ethoxylate, diethoxylate, or triethoxylate of 2,2,4-trimethyl-1,3-pentanediol and/or 2-ethyl-1,3-hexanediol. In the processes of this invention, these solvents should only be used in concentrations that do not provide a stable or clear product. Preferred are mixtures where the main solvent is one or more of the solvents designated as most preferred in the preceding text. The use of solvent mixtures is particularly preferred in those cases where one or more of the main solvents is a solid at room temperature. In this case, the mixtures are liquid or have lower melting points, which facilitates the processing of plasticizers.

It has also been found that it is possible to replace part of the main solvent or mixture of main solvents according to this invention with a secondary solvent or mixture of secondary solvents which are not suitable as main solvents according to this invention. This use is possible if an effective amount of a suitable main solvent or solvents is present so that the fabric softener concentrate is clear. The effective amount of the main solvent or mixture of main solvents according to the invention is higher than 5%, preferably higher than 7%, more preferably higher than 10% of the preparation, if the concentration of the active substance of the fabric softening preparation is at least 15%. The replacement solvent(s) may be used at any concentration, but preferably at a concentration equal to or lower than the above concentration of the appropriate main solvent present in the fabric softener. Although, for example, 1,2-pentanediol, 1,3-octanediol and hydroxypivalylhydroxypivalate (hereafter HPHP) HO-CH ₂ -C(CH ₃ ) ₂ -CH ₂ -O-CO-C(CH ₃ ) ₂ -CH ₂ -OH (CAS No. 1115-20-4) unsuitable solvents for use in the processes of this invention, mixtures of these solvents with a major solvent, for example 1,2-hexanediol present in an effective concentration, also provide a liquid, concentrated and clear fabric softener.

Some secondary solvents that can be used are the solvents that are in the preceding and following text • · · ♦ flflfl · • flfl • fl flfl flflfl •flfl ·· · • fl ·· flfl • fl · » · · • · · · · • · flflfl· · • · · · • fl·· ·· ·· listed as unsuitable solvents and some corresponding non-alkylated solvents are listed in Tables 8a-8e.

The main solvent can be used to either make the formulation transparent or clear, or it can be used to lower the temperature at which the formulation exists in transparent or clear form. The subject of this invention is also a method of adding the main solvent in amounts corresponding to the previously mentioned concentrations to a preparation which is not transparent or clear, or which has too high a temperature at which instability begins to manifest itself, in order to make this preparation transparent or clear, or, if this preparation is clear, for example at room temperature or at a temperature below a certain temperature to lower the temperature at which instability begins to appear, preferably by at least 5°C, more preferably by at least 10°C . The most significant advantage of the main solvent is the fact that it provides the maximum improvement in properties relative to the amount of this solvent used. It will be understood that the term solvent as used herein refers to the effect of the main solvent and not to its physical state at a certain temperature, since some main solvents are solids at room temperature.

Alkyl lactates

Some alkyl lactate esters, for example ethyl lactates and isopropyl lactates, have ClogP values in the effective range of 0.15 to 0.64 and can form liquid, concentrated, clear fabric softening preparations with the active substances of this invention, but they must be used in somewhat higher concentrations than more effective diol solvents such as 1,2-hexanediol. They can also replace other main solvents in obtaining liquid, concentrated, clear preparations for softening fabrics according to the present invention. This is illustrated by the example of lc.

All of the major solvents mentioned above are characterized by the unusually advantageous properties described above.

«9 • 9 9 9

9 9 ·

999 9 9

9 9

99 • * * ·

9 9 • 99

9 9 99 • 99··

III. Additives that may or may not be used (A) low molecular weight water-soluble solvents may also be used in concentrations of 0 to 12%, preferably 1 to 10%, more preferably 2 to 8%. These water-soluble solvents cannot provide a clear product at the same low concentrations as the concentrations of the previously mentioned major solvents, but may provide a clear product if the major solvent is insufficient to produce a completely clear product. The presence of these water-soluble solvents is therefore highly desirable. These solvents are: ethanol, isopropanol, 1,2-propanediol, 1,3-propanediol; propylene carbonate and the like, but they are not the main solvents (B). Similar to the fabric softener active ingredient, these water-soluble solvents in the presence of hydrophobic materials have a greater affinity for water than the main solvents.

(B) Glazing additives

The preparation according to the present invention may also contain 0.005 to 5% by weight of a certain type of hydrophilic optical brightening additive, which also has an inhibitory effect on dye transfer. The preparations according to the present invention preferably contain 0.001 to 1 wt.% of such optical gloss-forming additives. Hydrophilic optical brighteners suitable for use in the processes of this invention have the general structural formula:

where the substituent R-j_ is selected from the group of substituents formed by anilinyl, N-2-bis-hydroxyethyl and N-2-hydroxyethyl, the substituent R ₂ is selected from the group of substituents formed by N-2-bis-hydroxyethyl, N-2-hydroxyethyl -N-methylamino, morphylinyl, chlorine and amino, and M is a salt-forming cation such as sodium or potassium.

* ·· ♦ ·· ·· ·· ·· · · 99 9 9 9 9 9 9

99 · 9 9 9 99

9999 9 99 999 9 9

9 9 9 9 · 9 ·

999 99 999 9999 99 99

If in the above formula R]_ is anilinyl, R ₂ is N-2-bis-hydroxyethyl and M is a cation such as a sodium cation, the brightener is 4,4'-bis[(4-anilino-6-(N- 2-bis-hydroxyethyl)-s-triazin-2-yl)-amino]-2,2 ¹ -stilbenedisulfonic acid and its disodium salt. This commercially produced gloss additive is produced by Ciba-Geigy Corporation under the trade name Tinopal-UNPA-GX ^R . Tinopal-UNPA-GX is the preferred hydrophilic optical brightener used in the formulations of this invention for addition to rinse baths.

In the above formula, when R 2 is anilinyl, R ₂ is N-2-hydroxyethyl-N-2-methylamino, and M is a cation such as a sodium cation, the brightener is the sodium salt of 4,4'-bis[(4- anilino-6-(N-2-hydroxyethyl-N-methylamino)-s-triazin-2-yl)amino]2,2 ¹ -stilbenedisulfonic acid. This commercially produced gloss additive is produced by Ciba-Geigy Corporation under the trade name Tinopal-5BM-GX ^R .

In the above formula, when R is anilinyl, R ₂ is morpholinyl, and M is a cation such as a sodium cation, the brightener is the sodium salt of 4,4'-bis[(4-anilino-6-morpholino-s-triazine- 2-yl)amino]-2,2'-stilbenedisulfonic acids. This commercially produced gloss additive is manufactured by Ciba-Geigy Corporation under the trade name Tinopal-AMS-GX.

(C) Dispersing agents, viscosity modifying dispersing agents

Even without additives stabilizing concentrated solutions, it is possible to prepare relatively concentrated preparations containing both saturated and unsaturated diesters based on quaternary ammonium compounds. Preparations according to the present invention may, however, require organic and/or inorganic additives stabilizing concentrated solutions, which may allow for a further increase in concentration and/or, depending on the other components, to achieve higher stability. These concentrated solution stabilizing additives, which are usually viscosity modifying agents, may be necessary or advantageous to achieve stability under extreme conditions where particularly high concentrations of active agent are used

9

9

9

9 9 <

• · * · • ···· 4

100

No. 08/461 207, filed 5 is pending at the same time as the preparation for softening fabrics. These concentrated solution stabilizing surfactant additives are typically selected from the group consisting of: 1) cationic surfactants with one higher alkyl, 2) nonionic surfactants, 3) amine oxides, 4) fatty acids, and 5) mixtures of the above substances. These agents are described in the Procter & Gamble June 1995 patent application by Wahl et al., which by this application, especially from page 14,

line 12, to page 20, line 12, while this application is also included here as a reference.

If the mentioned dispersing agents are present, their total concentration is 2 to 25 wt.%, preferably 3 to 17 wt.%, more preferably 4 to 15 wt.% and even more preferably 5 to 13 wt.% of this preparation. These substances can be added either as part of the starting substances in the synthesis of the active substance of the fabric softening preparation (I), for example, a mixture of a single long-chain cationic surfactant and a fatty acid, which, as mentioned earlier, are the reactants used to prepare the active substances biodegradable fabric softeners, or they can be added as a separate ingredient. Part of the total concentration of the dispersant is its possible content in component (I).

(1) Quaternary ammonium compounds with one alkyl

When a quaternary ammonium compound with one alkyl is present, its concentration is usually 2 to 25% by weight, preferably 3 to 17% by weight, more preferably 4 to 15% by weight, and even more preferably 5 to 13% by weight, based to the total weight of the preparation, and is present in at least such a concentration that is effective. These monoalkyl quaternary ammonium species suitable for use in the processes of this invention have the general formula [R ⁴ N ⁺ (R°) ₃ ] X' where R ⁴ is C ₈ -C ₂₂ alkyl or alkenyl, preferably alkyl or alkenyl

101 ^C 10 ^_C 18' ^v more preferably alkyl or alkenyl C 10 ^_C 14 ^ne ^o ^C 16 ^- C ₁₈ , R ⁵ is alkyl or substituted C 10 -C 8 alkyl (for example hydroxyalkyl), preferably C 1 -C 8 alkyl, for example methyl (which is the most preferred alkyl), ethyl, propyl, and the like, a benzyl group, hydrogen, and a polyethoxylated chain with 2 to 20 oxyethylene units, preferably with 2.5 to 13 oxyethylene units, more preferably with 3 to 10 oxyethylene units and their mixture, and X" is the anion defined above (formula (I)).

Particularly preferred dispersing agents are monolauryltrimethylammonium chloride, and monoalkyltrimethylammonium chloride with alkyls derived from beef tallow fatty acids, supplied by Witco under the trade name Varisoft ^R 471, and monooleyltrimethylammonium chloride supplied by Witco under p

trade name Varisoft 417.

The group R ⁴ can also be bound to nitrogen via a group containing one or more ester, amide, ether and other linking groups, whereby a higher concentration of component (I) can be achieved.

This connecting group preferably contains one to three carbon atoms.

Quaternary ammonium compounds with one alkyl are also cholinesters with Cg-C ₂₂ alkyls. Preferred dispersants of this type have the general formula

R ¹ C(O)-O-CH 2 CH 2 N ⁺ (R) 3 X where R ⁴ , R and X” are the substituents defined previously.

Highly preferred dispersing agents are cholinesters with C ₁₂ -C ₁₄ alkyls derived from coconut oil fatty acids and cholinesters with C ₁₆ -C ₁₈ alkyls derived from beef tallow fatty acids. Suitable biodegradable dispersants with one long alkyl chain containing one ester linkage in the long chain are described in US Patent No. 4,840,738 to Hardy and Walley, issued June 20, 1989, which is incorporated herein by reference.

If dispersants contain alkylated cholinesters,

102. , based on the total weight of the product, organic acids. Organic acids are described in European Patent Application No. 404,471 to Machin et al., published Dec. 27, 1990, which is incorporated herein by reference. Preferably, these organic acids are selected from the group consisting of glycolic acid, acetic acid, citric acid and mixtures thereof.

Ethoxylated quaternary ammonium compounds that can be used as dispersants include, but are not limited to, ethyl bis(polyethoxyethanol)-alkylammonium ethyl sulfate with 17 ethylene oxide units per molecule, supplied under the trade name Variquat ^R 66 by Sherex Chemical Company, polyethylene glycol (15) oleylammonium chloride, supplied under the trade name Ethoquad ^R 0/25 by Akzo and polyethylene glycol (15) alkylammonium chloride with alkyls derived from fatty acids of coconut oil, supplied under the trade name Ethoquad C/25 by Akzo. Although the main function of the dispersing agents is to increase the dispersibility of the ester softener, the dispersing agents according to the present invention also have certain softening properties that increase the softening effect of the preparation. Therefore, the preparations according to the present invention do not contain non-ionic ethoxylated nitrogen-free dispersants, which would reduce the overall softening effect of these preparations.

Quaternary compounds with only one long alkyl chain also have the ability to protect the cationic softener from interacting with anionic softeners and/or detergents carried into the rinse stage from the wash stage.

(2) Amine oxides

Suitable amine oxides are amine oxides with only one alkyl or hydroxyalkyl with 8 to 22 carbon atoms, preferably with 10 to 18 carbon atoms, more preferably with 8 to 14 carbon atoms, and with two alkyl substituents selected from the group consisting of alkyl groups and hydroxyalkyl groups with 1 to 3 carbon atoms.

·· ·· i ·· · » to ·« ··· · · • · to • to ·· • to > 4 ··

103

Examples of these diethyldecylamine oxide, methyldodecylamine oxide, substances are dimethyloctylamine oxide, bis-(2-hydroxyethyl)dodecylamine oxide, didipropyltetradecylamine oxide, methylethylhexadecylamine oxide, dimethyl-2-hydroxyoctadecylamine oxide and alkyldimethylamine oxide with alkyls derived from coconut oil fatty acids.

(D) Stabilizers

Preparations stabilizers, includes e.g.

according to this invention may contain the Name stabilizer, used in this document, antioxidants and reducing agents. If they are antioxidants, they are present in a concentration of 0 to 2%, preferably 0.01 to 0.2%, more preferably 0.035 to 0.1%, if they are reducing agents, their concentration is preferably 0, 01 to 0.2%. Stabilizers guarantee good stability of the product against reactions leading to the formation of odorous substances. Antioxidants and reducing stabilizers are particularly important for fragrance-free or low-perfume (unperfumed or low-perfume) products. Examples of antioxidants that may be added in this invention are mixtures of ascorbic acid and propyl gallic acid supplied by Eastman Chemical Products, Inc. under the trade names Tenox ^R PG and Tenox ^R Sl and a mixture of BHT (butyl derivative of hydroxytoluene), BHA (butyl derivative of hydroxyanisole), propyl ester of gallic acid and citric acid, supplied by Eastman Chemical Products, lne. under the trade name Tenox ^R -6, for preparations according to ascorbic, palmitate supplied by the company R butylated hydroxytoluene, under the trade name supplied by the company Eastman Tenox ^R TBHQ, natural supplied by the company UOP Process Division p

Sustan BHT, tert.-butylhydroquinone, Chemical Produkts, flax. under the name tocopherols, supplied by Eastman, R

Chemical derivative Products, acid supplied

Products, lne. under the name Tenox ¹⁵ · GT-1/GT-2 and butyl hydroxyanisole, supplied by the company Eastman Chemical lne., under the designation BHA, higher gallic esters, for example dodecyl ester of gallic acid ^(C 8- ^C 22 gallic acid, > RR under the names Irganox 1010, Irganox 1035 ;

• 9 » · · 9 ► 9 99

999 9 9

9 9 ·· "R

104, R

Irganox B 1171;

and their mixtures, ,R „R ,R

Irganox 1425, preferably Irganox ¹ ^ 3125,

Irganox ¹ ' 3114 or in a mixture with citric acid and/or other chelating agents such as isopropyl ester of citric acid, as well as Dequest 2010, supplied by Monsanto, which is 1-hydroxyethylidenephosphonic acid (etidronic acid) and Tiron ^R , supplied by Kodak, which is

4,5-dihydroxy-m-benzenesulfonate and its sodium salt, p

DTPA, supplied by Aldrich, which is diethylenetriaminepentaacetic acid.

The chemical names and Chemical Abstracts journal registration numbers of some of the above stabilizers that can be used in the formulations of the present invention are shown in the following Table 1

Irganox 3114, ,R

Irganox ¹ ^ 3125,

Irganox^ 1425, _r R and their mixtures, more preferably Irganox^ 3125 acid itself and acid preparation (E) Reagents facilitating the release of solid impurities

Preparations according to the present invention can facilitate the release of solid impurities, facilitate the release of solid impurities in combination with the preparation of the premix, in combination contain reagents. of the final product. The softening preparation, prepared by the method according to this invention, may contain 0 to 10%, preferably 0.2 to 5%, of agents facilitating the release of solid impurities. Preferably, this agent facilitating the release of solid impurities is a polymer. Polymeric solid release agents suitable for use in the processes of this invention may be block copolymers containing terephthalic and polyethylene oxide blocks, polypropylene oxide, and the like.

A preferred agent for facilitating the release of solid impurities is a copolymer with polyethylene oxide terephthalate blocks. These polymers contain alternating ethylene terephthalate and polyethylene oxide terephthalate blocks at a molar ratio of ethylene terephthalate units to polyethylene oxide terephthalate units

105 years

• · • ···» ··

• · · • fl ··

25:75 to 35:65, wherein the polyethylene oxide terephthalate contains polyethylene oxide blocks with molecular weights of 300 to 2000. The molecular weight of these solid release agents ranges from 5,000 to 55,000. Another preferred solid release agent is a semi-crystalline polyester containing 10 to 15% ethylene terephthalate structural units and 10 to 50% polyethylene oxide terephthalate units with polyoxyethylene blocks of molecular weight 300 to 6000, the ratio of ethylene terephthalate units to polyoxyethylene terephthalate units in this partially crystalline polymer ranging from 2:1 to 6:1. Examples of this polymer are the industrially produced preparations Zelcon 4780 ^R (from Dupont) and Milease ^TR (from ICI).

Highly preferred agents facilitating the release of solid impurities are polymers of the general formula:

where X is any suitable terminal group, usually H or an alkyl or acyl of 1 to 4 carbon atoms, p is chosen according to the desired water solubility and is generally in the range of 6 to 113, preferably 20 to 50. A proper choice of u has of great importance in order to prepare a liquid substance with a relatively high ionic strength. The content of the fraction with a u value higher than 10 needs to be very low. Furthermore, the content of fractions with a u value in the range of 3 to 5 must be at least 20%, preferably 40%.

R ¹⁴ groups are mainly 1,4-phenylene groups. For the purposes of this document, this means that it is either exclusively these groups, or that these 1,4-phenylene groups are partially replaced by other arylene, alkarylene alkylene or alkenlene groups, or mixtures thereof. Arylene and alkarylene groups, which can partially replace

0·0<

» 0 0 » 0 00

0 0 0 4

0« » ι • 0

106

1,4-phenylene groups are 1,3-phenylene, 1,2-phenylene, 1,8-naphthylene, 1,4-naphthylene, 2,2-biphenylene, 4,4-biphenylene, and mixtures thereof. Alkylene and alkenylene groups that can partially replace 1,4-phenylene groups are 1,2-propylene, 1,4-butylene, 1,5-pentylene, 1,6-hexamethylene, 1,7-heptamethylene, 1,8 -octamethylene, 1,4-cyclohexylene and their mixtures.

The partial replacement of the 1,4-phenylene groups R ¹⁴ by other groups should not exceed such a degree as to cause significant difficulties in the release of solid impurities. In general, the degree of this partial replacement that can be tolerated depends on the chain length of the compound in question, ie for longer chain compounds the 1,4-phenylene groups may be replaced to a greater extent. Mostly, substances in which R groups are ¹⁴ have from 50 to 100%

1,4-phenylene groups (i.e. substances with 0 to 50% by weight of groups other than 1,4-phenylene groups), good ability to facilitate the release of solid impurities. Thus, for example, polyesters according to the present invention with a molar ratio of isophthalic acid (1,3-phenylene) to terephthalic acid equal to 40:60 have a good ability to facilitate the release of solid impurities. However, since most of the polyesters used in the production of synthetic fibers ethylene terephthalate maximum capacity contains the achievement of impurities

1,4-phenylenene

Ί 4- in the R groups exclusively 1,4-phenylene monomer units, it is usually appropriate to minimize the degree of partial replacement of the j group by other groups in order to facilitate the release of solids. Preferably, there are groups (i.e. content

of 1,4-phenylene groups is 100%).

-i c

Suitable R groups are ethylene groups and substituted ethylene groups, which are ethylene, 1,2-propylene, 1,2-butylene, 1,2-hexylene and 3-methoxy-1,2-propylene groups and mixtures thereof. Preferably, R ¹⁵ groups are exclusively ethylene groups, 1,2-propylene groups or their mixtures. Increasing the content of ethylene groups generally improves the ability to facilitate the release of solid impurities. It is surprising that increasing the content of 1,2-propylene groups increases the solubility of the respective substances in water.

So that it is possible to achieve a significant proportion of the agent

• · • · · • · • 99

107 ···· facilitating the release of solid impurities in the liquid fabric softener, the use of 1,2-propylene groups or their analogues with a branched structure is desirable. Preferred content

75 to 100% of I,2-propylene groups.

The p value is at least 6, and preferably at least 10. The n value is typically 12 to 113. The p value is typically 12 to 43.

For a more detailed description of solid release agents, see US Pat. Nos. 4,661,267 to Decker, Konig, Straathof and Gosselink, issued April 28, 1987, and No. 4,711,730 to Gosselink and Diehl, issued Dec. 8, 1987. No. 4,749,596 to Evans, Huntington, Stewart, Wolf and Zimmerer, issued Jun. 7, 1988, No. 4,818,569 to Trinh, Gosselink, and Rattinger, issued Apr. 4, 1989, No. 4,877,896 to Maldonado , Trinh and Gosselink, issued October 31, 1989, No. 4,956,447, authors Gosselink et al., issued June 11, 1990, no. 4,976,879 to Maldonado, Trinh and Gosselink, issued

II, December 1990, all of which are incorporated herein by reference. These solids release agents can also act as antifoam additives.

(F) Defoamers

In the procedures according to this invention, in addition to the agent facilitating the release of solid impurities, a defoaming additive can be added to the premix and then heated to the melting point of this substance or to a higher temperature.

Suitable defoamers for use in the processes of this invention are highly ethoxylated hydrophobic materials. These hydrophobic materials can be fatty alcohols, fatty acids, fatty amines, fatty acid amides, amine oxides, quaternary ammonium substances or hydrophobic monomers used for the synthesis of polymers suitable as agents facilitating the release of solid impurities. Preferred antifoam additives contain a significant amount of ethoxy groups, for example, on average more than 17, preferably more than 25 and more preferably more than 40 ethylene oxide units in one molecule, the mass fraction of polyethylene oxide to the total molecular weight being 76 to 97%, preferably 81 to 94% .

• ·

- 108 ··· · • · • · ι

Such a concentration of the defoaming additive is used that keeps the amount of foam in use at an acceptable level, which is almost imperceptible to the user and at the same time does not have a negative effect on the softening effect. In some cases, it is desirable that no foaming occurs at all. The amount of anionic or nonionic surfactants and agents increasing the detergency effect (especially phosphates and zeolites) trapped in the washed fabric depends on the amount of anionic and nonionic detergents that are used in the wash cycle of the normal washing process, the effectiveness of the rinse, which is preceded by the addition of softening agents fabrics according to this invention, and on the hardness of the water. It is common practice to use as little antifoam additive as possible to avoid a negative effect on the softening properties. The usual concentration of defoaming additives is at least 2%, preferably at least 4% (optionally at least 6% and preferably at least 10% if the maximum defoaming effect is to be achieved) based on the active substance of the fabric softener. At concentrations of around 10% (relative to the active substance of the fabric softener), or at even higher concentrations, there is a risk of reducing the effectiveness of the softener, especially if the fabrics contain high concentrations of non-ionic surfactants absorbed during the washing process.

Preferred defoamers are: Brij 700 ^R , Varonic U-2S0 ^R , Genapol T-500 ^R , Genapol T-800 ^R , Plurafac A-79 ^R and Neodol 2S-SO ^R .

(G) Bactericides

Examples of bactericides used in the preparations of this invention are glutaraldehyde, formaldehyde, 2-bromo-2-nitro-propane-1,3-diol supplied by Inolex Chemicals, Philadelphia, Pennsylvania, under the trade name Bronopol ^R, and a mixture of 5-chloro-2- methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one, supplied by the Rohm and Haas Company under the trade name Kathon.

109 (H) Perfumes

The preparations according to the present invention may contain any perfume which is chemically compatible with them. Suitable perfumes are described in US Patent No. 5,500,138 to Bacon et al., issued March 19, 1996, which is incorporated herein by reference. Perfumes are aromatic substances or mixtures of aromatic substances, which can be natural substances (obtained by extracting flowers, herbs, leaves, roots, bark, wood, flowers) and synthetic substances (i.e. artificially synthesized substances). Perfumes often contain auxiliary substances such as fixatives, fillers, stabilizers and solvents. For the purposes of this document, all of these substances fall under the label of perfume. Usually, perfumes are complex mixtures of a number of organic substances.

Examples of perfume components that can be used in the preparations according to the present invention are, among others, hexylcinnamaldehyde, amylcinnamaldehyde, amyl salicylate, hexylsalicylate, terpineol, 3,7-dimethyl-cis-2,6-octadien-l-ol, 2,6-dimethyl -2-octanol,

2,6-dimethyl-7-octen-2-ol, 3,7-dimethyl-3-octanol, 3,7-dimethyl-trans-2,6-octadien-1-ol, 3,7-dimethyl-6- octen-1-ol, 3,7-dimethyl-1-octanol, 2-methyl-3-(p-tert-butylphenyl)-propionaldehyde,

-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde, tricyclodecenyl propionate, tricyclodecenyl acetate, anisaldehyde, 2-methyl-2-(para-iso-propylphenyl)-propionaldehyde, ethyl 3-methyl-3-phenylglycidate , 4-(p-hydroxyphenyl)-butan-2-one,

1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one, p-methoxyacetophenone, p-methoxy- -phenylpropene, methyl-2-n-hexyl-3-oxo -cyclopentanecarboxylate, -undecanoic acid lactone.

Other examples of fragrances include, but are not limited to, orange essential oil, lemon essential oil, grapefruit essential oil, bergamot oil, clove essential oil, dodecanoic acid lactone, methyl 2-(2-pentyl-3-oxo-cyclopentyl)acetate, -naphthol methyl ether, methyl- -naphthyl ketone , coumarin, decylaldehyde, benzaldehyde, 4-tert.-butylcyclohexyl acetate, , -dimethylphenethyl acetate, methylphenylcarbinyl acetate, Schiff base of 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde and methylanthranilate, cyclic ethylene glycol diester of tridecanedioic acid , 3,7-dimethyl-2,6-octa110 diene-1-nitrile, -methylionone, -ionone, petitgrain, methylcedrylone, 7-acetyl-1,2,3,4,5,6,7,8-octahydro- 1,1,6,7-tetramethyl-naphthalene, methylionone, methyl-1,6,10-trimethyl-2,5,9-cyclododecatrien-1-yl-ketone, 7-acetyl-1,1,3,4, 4,6-hexamethyltetralin, 4-acetyl-6-tert-butyl-1,1-dimethylindane, benzophenone, 6-acetyl-1,1,2,3,3,5-hexamethylindane, 5-acetyl-3-isopropyl -1,1,2,6-tetramethylindane, 1-dodecanal, 7-hydroxy-3,7-dimethyloctanal, 10-undecen-1-al, iso-hexenylcyclohexylcarboxaldehyde, formyltricyclodecane, cyclopentadecanolide, 16-hydroxy-9-hexadecanoic acid lactone , 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta- -2-benzpyran, ambroxan, dodecahydro-3a,6,6,9a-tetramethylnaphtho-[2 ,1b]furan, cedrol, 5-(2,2,3-trimethylcyclopent-3-enyl)-3-methylpentan-2-ol, 2-ethyl-4-(2,2,3-trimethyl-3-cyclopenten- 1-yl)-2-buten-1-ol, caryophyllene alcohol, cedryl acetate, p-tert-butyl cyclohexyl acetate, patchouli, frankincense resin, labdanum, vetiver essential oil, spearmint balsam, fir balsam and its condensation products: hydroxycitronellal and methyl anthranilate, hydroxycitronellal and indole, phenylacetaldehyde and indole, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carboxaldehyde and methyl anthranilate.

Other examples of perfume ingredients are geraniol, geranyl acetate, linalool, linalyl acetate, tetrahydrolinalool, citronellol, citronellyl acetate, dihydromyrcenol, dihydromyrcenyl acetate, tetrahydromyrcenol, terpinyl acetate, nopol, nopyl acetate,

2-phenylethanol, 2-phenethyl acetate, benzyl alcohol, benzyl acetate, benzyl salicylate; benzyl benzoate, styralyl acetate, dimethyl benzyl carbinol, trichloromethylphenylcarbinylmethylphenylcarbinyl acetate, isononyl acetate, vetiveryl acetate, vetiverol, 2-methyl-3-(p-tert-butylphenyl)-propanal, 2-methyl-3-(p-isopropylphenyl)-propanal, 3-(p- tert-butylphenyl)propanal, 4-(4-methyl-3-pentenyl)-3-cyclohexenecarbaldehyde, 4-acetoxy-3-pentyltetrahydropyran; methyl dihydrojasmonate, 2-n-heptylcyclopentanone, 3-methyl-2-pentyl-cyclopentanone, n-decanal, n-dodecanal, 9-decen-l-ol, phenoxyethyl isobutyrate, dimethylacetal of phenylacetaldehyde, diethylacetal of phenylacetaldehyde, geranonitrile, nitrile of citronellal acid, cedrylacetal, 3-isocamphylcyclohexanol, methyl cedryl ether, isolongifolanon, aubepinnitrile, aubepin, heliotro• ·

- 111 ···· ·· · · pine, eugenol, vanillin, diphenyl oxide, hydroxyeitronellal, ionones, methylionones, isomethylionones, irons, cis-3-hexenol and its esters, indane musk, tetralin musk, isochroman musk, macrocyclic ketones, macrolactones musk, ethylene brasylate.

Perfumes suitable for the preparations according to the present invention are essentially free of halogenated materials.

Suitable solvents, diluents or carriers for the above perfume components are, for example, ethanol, isopropanol, diethylene glycol, monoethyl ether, dipropylene glycol, diethyl phthalate, triethyl citrate and the like. The content of these solvents, diluents or carriers contained in the perfumes is preferably kept to the minimum necessary to obtain a homogeneous solution of the perfume.

The perfume content in the product can be 0 to 10% by weight, preferably 0.1 to 5% by weight and more preferably 0.2 to 3% by weight, based on the weight of the finished product. The fabric softening compositions of the present invention allow for improved perfume deposition.

(I) Chelating agents

The preparations according to the present invention may contain one or more chelating agents, forming copper or nickel chelates. As noted below, these water-soluble chelating agents may be selected from the group consisting of aminocarboxylates, aminophosphates, polysubstituted aromatic chelating agents, and mixtures thereof. These chelating agents will significantly increase or restore the whiteness of fabrics, or the brightness of their colors, and at the same time increase the stability of the substances contained in the preparations.

Aminocarboxylates suitable as chelating agents according to the present invention include ethylenediaminetetraacetates (EDTA), N-hydroxyethylenediaminetriacetates, nitrilotriacetates (NTA), ethylenediaminetetrapropropionates, ethylenediamino-Ν,Ν ¹ -diglutamates, 2-hyroxypropylenediamino-N,N'-disuccinates, triethylenetetraaminohexaacetates, diethylenetriaminepentaacetates (DETPA), and ethanoldiglycines, including their water-soluble salts, such as alkali metal salts, ammonium and substituted ammonium salts, and mixtures thereof.

If at least low levels are permissible in the detergent components • ·

• · ·· · concentration of phosphorus, aminophosphonates are also suitable as chelating agents for use in the preparations according to this invention, which are ethylenediaminetetrakis(methylenephosdiethylenetriamino-N,Ν,N ¹ ,Ν,N-pentakis(methanephosphonate)) (DETMP) and 1- hydroxyethane-1,1-diphosphonate (HEDP) Preferably, these aminophosphonates do not contain alkyl or alkenyl groups with more than 6 carbon atoms.

These chelating agents are typically used during the rinse cycle at concentrations of 2 to 25 ppm, with fabric contact times ranging from 1 minute to several hours.

A preferred chelating agent for use in the compositions of this invention is ethylenediamine-N,Ν'-disuccinate (EDDS), which is described in the previously cited US Patent No. 4,704,233 and has (in the form free acid) formula:

hn-ch ₂ -ch ₂ —nh

CH ₂ -CH

I I

COOH COOH

CH-CH ₂

I I

COOH COOH

As described in the said patent, EDDS can be prepared by reacting maleic anhydride with ethylenediamine. The preferred biodegradable [S,S] isomer of EDDS can be prepared by reacting L-aspartic acid with 1,2-dibromoethane. The advantage of EDDS compared to other chelating agents is the fact that it easily forms chelates by reacting with both copper cations and nickel cations, it can be prepared in a biodegradable form and does not contain phosphorus. EDDS used using the methods of this invention as a chelating agent is usually used in salt form, i.e., one or more acidic hydrogens in its molecule are replaced by a water-soluble cation, such as a sodium, potassium, ammonium, triethanolammonium cation, and or other similar cation. As previously stated, the EDDS chelating agent acts in the rinse, usually at concentrations of 2 to 25 ppm for periods ranging from 1 minute to several hours. At certain pH values, EDDS is advantageously used ··

- 113

in combination with zinc cations.

As can be seen from the foregoing, a number of different chelating agents can be used in the processes of this invention. Simple polycarboxylates such as citrate, oxydiantrate and the like may also be used, although these chelating agents are not as effective as aminocarboxylates and phosphonates. The concentrations of the chelating agents can be adjusted with respect to different degrees of chelating efficiency. The stability constant of the chelating agents (in a fully ionized state) used in the preparations according to the present invention is preferably for copper ions at least 5 and more preferably at least 7. The chelating agents preferably form 0.5 to 10% by weight, more preferably 0.75 to 5 wt.% of the total weight of the preparations according to this invention. Preferred chelating agents are DETMP, DETPA, NTA, EDDS and mixtures thereof.

(J) Other possible ingredients

Preparations according to this invention may optionally contain other components that are usual components of preparations for fabric treatment, for example dyes, preservatives, surface-active substances, substances that reduce fabric shrinkage, curling additives, detangling additives, germicides, fungicides, antioxidants such as, for example, butyl derivatives of hydroxytoluene, anti-corrosion additives and the like.

Particularly preferred additives are water-soluble compounds of calcium and/or magnesium, which further increase the stability of the preparations. Chlorides are preferred, but acetates, nitrates and other salts may also be used. The concentration of the mentioned calcium and/or magnesium salts is 0 to 2%, preferably 0.05 to 0.5%, more preferably 0.1 to 0.25%.

The compositions of this invention may also contain other compatible ingredients, including those listed in Invention Application Nos. 08/372,068, Rusche et al., filed Jan. 12, 1995, No. 08/372,490, Shaw,

Jan. 12, 1995, and No. 08/277,558, et al., filed Hartman et al., filed Jul. 19, incorporated by reference.

1994 which are in this document

- 114 ·· ·· • ·

·· * • ·

Solid preparations

1. Preparations in the form of solid particles

As already mentioned, preparations in the form of solid particles, containing:

(A) 50 to 95%, preferably biodegradable fabric active substances, (B) 0 to 30%, preferably 3 to 15%. properties, and (D) 0 to 10% pH modifier to 90% of said dispersant modifier softening agent pH modifier

Since the active substances of fabric softening preparations, which are biodegradable esters, are somewhat prone to hydrolysis, the preparation in the form of solid particles, from which stable more or less concentrated liquid softening preparations are subsequently formed by the addition of water, may contain pH modifiers. Said stable liquid preparations should have a (final) pH of 2 to 5, preferably 2 to 4.5, more preferably 2 to 4.

The pH can be adjusted by adding solid water-soluble Bronstedt acid. Examples of suitable Bronstedt acids are inorganic mineral acids such as boric acid, sodium hydrogen sulfate, potassium hydrogen sulfate, sodium hydrogen phosphate, potassium hydrogen phosphate and mixtures thereof, organic acids such as citric acid, fumaric acid, maleic acid, malic acid, tannic acid, gluconic acid, glutamic acid, tartaric acid, glycolic acid, chloroacetic acid, phenoxyacetic acid, 1,2,3,4-butanetetracarboxylic acid, benzenesulfonic acid, benzenephosphonic acid, orthotoluenesulfonic acid, paratoluenesulfonic acid, phenolsulfonic acid, naphthalenesulfonic acid, schuavelic acid, 1,2, 4,5-pyromellitic acid, 1,2,4-trimellitic acid, benzoic acid, phenylacetic acid, salicylic acid, succinic acid, • to • · · · · · · to < to· to ·« to · · · to their mixtures and mixtures of mineral inorganic acids and organic acids. Preferred pH modifiers are citric acid, gluconic acid, tartaric acid, 1,2,3,4-butanetetracarboxylic acid, malic acid and mixtures thereof.

As an adjuvant in preparations with solid particles, concentrated liquid acids and/or anhydrides, for example acetic acid, HCl, sulfuric acid, phosphoric acid, nitric acid, carbonic acid, etc., can be used as carriers. also used substances that have the ability to form solid clathrates, such as cyclodextrins and/or zeolites. An example of such a solid clathrate is carbon dioxide adsorbed in zeolite A as described in US Patent No. 3,888,998 to Whyte and Samps, issued June 10, 1975, and in US Patent No. 4,007,134 to Liepe and Japikse. issued June 8, 1977, both of which are incorporated herein by reference. Examples of phosphoric acid, sulfuric acid, and nitric acid inclusion complexes and their preparation are described in US Patent No. 4,365,061 to Szejtli et al., issued December 21, 1982, which is incorporated herein by reference.

If a pH modifier is used, its usual concentration is 0.01 to 10 wt.%, preferably 0.1 to 5 wt.%, based on the total weight of the preparation.

Preparation of fabric softener in the form of solid granules

Granules can be prepared by starting from a melt, allowing it to solidify by cooling, then crushing and screening to the desired size In the case of a three-component mixture, for example a mixture of nonionic surfactant, cationic surfactant with one long chain and DEQA, it is preferable to prepare the granules by first mixing the nonionic surfactant, a more soluble cationic compound, and then adding the quaternary ammonium cationic diester to the melt.

It is very advantageous if the primary particles of the granules have a diameter of 50 to 1000, preferably 50 to 400, more preferably 50 to 200 micrometers. Granules can contain smaller and larger particles

I •9 9 99 99 99

9 9 · 9 9999

99 9 9 9 9 99

9 9 9 9 9 9 999 9 9

- 116 .-*····· .ί. «:.· however, it is preferable if they contain 85 to 95%, or it is even more preferable if they contain 95% to 100%, of particles in the specified range. Larger and smaller particles do not provide optimal emulsions or dispersions when added to water. Other methods of preparing primary particles can be used, including spray cooling of the melt. Primary particles can be agglomerated to form a dust-free, non-sticky and free-flowing powder. Agglomeration can be carried out in a conventional agglomeration unit (for example in a Zig-Zag Blender, manufactured by Lodige) using a water-soluble binder. Examples of water-soluble binders suitable for this agglomeration are glycerol, polyethylene glycols, polymers such as PVA, polyacrylates and natural polymers such as sugars.

The fluidity of the granules can be improved by treating the surface of the granules with substances that improve fluidity, such as particles of clay, quartz or zeolite, water-soluble inorganic salts, starch and the like.

Methods of use

By adding water to solid preparations in the form of granules, diluted or concentrated liquid preparations for fabric softening can be prepared, which can further be used in the rinsing cycle of the washing process in a concentration of these biodegradable cationic softening substances of 0.5 to 50%, preferably 1 to 35% , more preferably 4% to 32 h Preparation in the form of solid particles 1), added to the rinsing cycle, can also be added directly to the rinsing bath in an amount corresponding to the concentration required for this purpose (e.g. 10 to 1000 ppm, preferably 50 to 500 ppm of the total amount of the active ingredient of the fabric softener). Liquid preparations can also be added to the rinsing bath in an amount corresponding to the same concentrations.

The temperature of the water used for preparation should be in the range of 20°C to 90°C, preferably 25°C to 80°C. In the case of using a solid preparation, cationic surfactants with one long alkyl chain are preferred as viscosity/dispersibility modifiers in concentrations of 0 to 15 wt.%, preferably 3 to 15 wt.%, more preferably 5 to 15 wt.%, based on the total ··

I 1 ··

- 117 ·· • · • ···· product weight. As viscosity/dispersibility modifiers, non-ionic surfactants can also be successfully used in concentrations of 5 to 20% by weight, preferably 8 to 15% by weight, as well as mixtures of these substances.

In order to achieve effective deposition on the fabric, the emulsified/dispersed particles formed when said granules are added to water to form aqueous concentrates should generally have an average particle size of less than 10 micrometers, preferably less than 2 micrometers, more preferably 0, 2 to 2 micrometers. The phrase average particle size in the context of this description means the numerical average of particle sizes, i.e. more than % of these particles have a diameter smaller than the specified size.

The size of the emulsified/dispersed particles is determined, for example, with a Malvern particle size analyzer.

Depending on the choice of nonionic or cationic surfactant, in some cases when using solids to form liquid systems, it may be desirable to use an effective device for dispersing and emulsifying the particles (for example, a mixer).

Preparations in the form of solid particles, used for the preparation of liquid preparations, may contain electrolytes, perfumes, antifoam additives, additives improving fluidity (e.g. quartz), dyes, preservatives and/or possibly other components described above.

The advantage of preparing liquid preparations intended for use in rinsing baths by adding water to the preparation in the form of solid particles is that it allows less weight to be transported and thus makes transport cheaper, and that it is possible to prepare liquid preparations similar to formulations that are commonly sold to consumers, such as those described herein, with lower energy consumption (i.e., with less intensive mixing and/or at a lower temperature). Preparations for softening fabrics in the form of solid granules, sold in this form directly to customers, also have lower requirements for packaging and it is possible to use packaging in smaller, more easily disposed of packages. The consumer then transfers the product to a suitable larger solid container and, by pre-dilution with water, obtains a product that is ready for use in the rinsing bath, as well as

9 9

118

9 99

99

9 9 φ 9

9

9

999 9999

99

9 9 9

9 99

9999 ·

9 9

99 liquid preparation. Working with the liquid form is easier because it simplifies measuring and dosing.

2. Preparations activated in the dryer

The subject of this invention are also improved dryer-activated fabric softening preparations that are either A) part of other products, e.g. applied to a substrate, or previously described particles (including pellets made from these particles). These

B) exist in the form of agglomerates and tablets, the preparations usually contain 10 fabric softeners.

and from the active substance

A. Products on the substrate

in in a preferred embodiment, there is a preparation according to this of the invention as part another product. Examples of these and others products, designed to perfume and soften at the same time fabrics in automatic dryer, are listed in US patents C. 3 988 631, author Marsan, released on 2 november 1976, in C. 4 055 248, author Marsan, released on 25 October 1977, sz C. 4 073 996, authors Bedenk et al., published February 14th 1978, C. 4 022 938, authors Zaki et al., ed 10 May 1977, C. 4 764 289, author Trinh, released on 16 august 1988, \of C. 4 808 086, authors Evans et al., ed February 28 1989; \of C. 4 103 047, authors Zaki et al., published on 25 July 1978, C. 3 736 668, author Dillarstone, published on 5 June 1973, in C. 3 701 202, authors Compa et al., published 31.st October 1972, \of C. 3 634 947, author Furgal, released on 18 January 1972, \of C. 3 633 538, author Hoeflin, published on 11 January 1972, sz C. 3 435 537, by Rumsey, issued April 1, 1969, and 4,000,340,

by Murphyt et al., published Dec. 28, 1976, all of which are incorporated herein by reference.

Typical products of this type consist of:

I. from a fabric treatment product containing 30 to 95% at room temperature of solid active substances for fabric softening, which softens at dryer temperatures

119

ΦΦΦ · φφ φ φ φ φ φφφ · φφφφ φ φ- φ φ φ φφφ φφ φφφ φφ φφ φφ φ φφφφ φ φ · φφ φ φ φφφ φ φ φφφ φφφφ φφ φφ a

II. from a dispersing agent capable of releasing an effective amount of said preparation, including an amount of said dispersing agent sufficient to controllably perfume the fabric in an automatic clothes dryer at the operating temperatures at which drying takes place in this dryer, for example at temperatures of 35 to 115°C.

If the said dispersing agent is a flexible substrate, for example in the form of a sheet, the fabric treatment agent is fixed on this substrate in a way that allows the release of this agent in an amount corresponding to the weight ratio of this fabric agent to the dry substrate weight of 10:1 to 0.5: 1, preferably 5:1 to 1:1.

Solid fabric softening compositions according to the invention may contain a combination of cationic and nonionic active substances.

Preparation of main solvents

Preparation of diol main solvents

A variety of synthetic methods can be used to prepare the principal solvents of this invention. For each particular main solvent, a suitable method is chosen, corresponding to its structure. Most major solvents can be prepared by more than one method. Therefore, the methods presented here for certain major solvents are for illustration purposes only and cannot be considered as the only suitable methods.

• ·

120 ··-· ·' • ·· 99 ·· • 99 · · 9 9 · • · 9 9 ·· • · · 999 9 9

9 9 9 9 • 99 9999 99 99

Method A

Preparation of 1,5-, 1,6-, and 1,7-diols

Method 1

This method is a general method for the preparation of , -diols derived from substituted cyclic alkenes. Examples of cyclic alkenes are the alkylated isomers of cyclopentene, cyclohexene and cycloheptene. The general formula of suitable alkylated cyclic alkenes is

x where R is H or alkyl C-|_-C ₄ and where x is 3, 4 or 5.

Cyclic alkenes can be converted to diols and hydroxyls at the terminal carbons in a three-step reaction.

The first step is the reaction of cyclic alkenes with ozone (O ₃ ) in a solvent such as anhydrous ethyl acetate to form an intermediate ozonide. In the second stage, this ozonide is reduced, for example, by hydrogen on a palladium catalyst to dialdehyde, which is then converted in the third stage by reduction with boron hydride to a synthesized diol. 1,2-diols are generally prepared by direct hydroxylation of the corresponding substituted olefins. Example:

C=C where R is H, alkyl, etc.

Typically, the alkene is reacted with hydrogen peroxide (30%) in the presence of a catalytic amount of osmium oxide in tert-butyl alcohol or other suitable solvent, the reaction mixture is cooled to 0°C, and the reaction is allowed to proceed overnight.

- 121 • φ » « ·· ♦ ·· φφ φφ φφ · · φφφφ • φφφφ* φ · φ φφφφ φ φ φ φφφ φφφ φφφφ φφφφ

Unreacted starting materials and solvent are removed by distillation and the corresponding 1,2-diol is separated by distillation or crystallization.

Method 2

An alternative method is to convert the olefin to an epoxide by reaction with m-chloroperoxybenzoic acid or peroxyacetic acid in a solvent such as methylene chloride at temperatures below 25 °C. The epoxide formed in this way is then opened to form a diol, for example by hydrolysis with dilute sulfuric acid. Step 3 to form the synthesized diol is performed by reduction with boron hydride.

Method 3

An alternative method for the preparation of these compounds is the direct hydroxylation of a cyclic catalytic amount of a cyclic diol with hydrogen peroxide in the presence of osmium oxide. It is then converted into an open-chain dialdehyde using peroxyiodate or lead tetraacetate. The obtained dialdehyde is then reduced with boron hydride as in method 1 to form synthesized diols 1,5- or 1,6-, etc.

Method B

Preparation of 1,2-diols

Method 1

« ·

122··* ♦·

Method C

Preparation of 1,3-diols

Acylation of enamines

This method of preparation is a general method of preparation of 1,3-diols and is used to prepare various structural types. Enamines are prepared from ketones and aldehydes that react with acid chlorides to form acylated products. The acylated amine derivative is hydrolyzed back to the corresponding acylated carbonyl compound, which is the 1,3-dicarbonyl precursor of the desired 1,3-diol. This diol is obtained by reducing this 1,3-dicarbonyl compound with boron hydride.

Acetaldehyde (aldehydes in general) can be reacted with a secondary amine, preferably cyclic amines such as pyrrolidine or morpholine, by refluxing in a solvent such as toluene in the presence of a catalytic amount of p-toluenesulfonic acid. During the reaction (condensation) of an amine with a carbonyl compound, the resulting water is removed, for example, by distillation in a freezer. After removal of the theoretical amount of water, the reaction mixture is stripped, for example under vacuum, to remove the solvent if necessary (acylation can be carried out in most cases the same solvent system).

The anhydrous crude enamine, containing some excess amine, is reacted with the corresponding acid chloride at 20°C to form the acylated enamine. This reaction is usually carried out with stirring overnight at room temperature. The reaction mixture is then poured onto crushed ice, stirred, and acidified with 20% HCl. This hydrolyzes the enamine to an acylated dicarbonyl compound. This intermediate is then isolated by extraction and distillation to remove low-boiling impurities and then reduced with sodium tetraborate to the desired 1,3-diol.

• ·

123·

Method D

Preparation of 1,4-diols by aldol condensation and reduction

This type of reaction involves one or more aldehydes, one or more ketones, or a mixture of these substances that have at least one -hydrogen on the carbon atom adjacent to the carbonyl group. Typical examples of some reactants and some potential end products are given below:

r-ch ₂ -cho = ho-ch ₂ -ch(r)-choh-ch ₂ -r r-ch ₂ -cho + R'-CH ₂ -CHO = HO-CH ₂ -CH(R)-choh- ch ₂ -r + HO-CH ₂ -CH(R')-CHOH-CH ₂ -R' +

HO-CH ₂ -CH(R')-choh-ch ₂ -r +

HO-CH ₂ -CH(R)-CHOH-CH ₂ -R' r-ch ₂ -cho + R'-CO-CH ₃ = ho-ch ₂ -ch(r)-choh-ch ₂ -r +

R-CH ₂ -CHOHCH ₂ -CHOH-R'

The aldehydes, ketones or mixtures thereof to be subjected to the condensation reaction are placed in an autoclave in an inert atmosphere with a solvent such as butanol or a phase transfer medium such as polyethylene glycol. When a mixed condensation is to be carried out, such as that of a ketone with an aldehyde, usually the two reactants are used in a 1:1 molar ratio. A catalytic amount of a strongly alkaline catalyst such as sodium methoxide is added in an amount that is typically 0.5-10 mole percent of the total reactants. The autoclave is closed and the reaction mixture is heated to 35 to 100°C until most of the original amount of reactants has reacted, usually for 5 minutes to 3 hours. The crude reaction mixture is neutralized and the carbonyl groups present are reduced by hydrogenation over Raney nickel at a temperature of 100°C and a pressure of 5 MPa for about 1 hour. The volatiles were removed by distillation and the synthesized diol main solvent was separated by distillation under reduced pressure.

• ·

- 124,

in international et al., 16.

Further information on this synthetic method is given in A. Pochini, R. Ungaro Synthesis, (3), 164-5 (1975), Patent Application WO 9,507,254, authors Kulmala March 1995, in Japanese Patent Application

No. 40,333, Sato et al., Feb. 9, 1990, in Japanese Patent Application No. 299,240, Sato et al., Dec. 4, 1989, in European Patent Application No. 367,743, Ankner et al., May 9, 1990, all of which articles and patent applications are incorporated herein by reference.

Illustrative examples:

Condensation of butyraldehyde and/or isobutyraldehyde and conversion to eight-carbon 1,3-diols n-Butanol (148 g, 2 mol, Aldrich) in a 500 mL three-necked flask equipped with a stirrer, internal thermometer, reflux condenser and connected to a source of inert nitrogen of atmosphere is allowed to react with sodium metal (2.3 g, 0.1 mol, Aldrich) until it is completely dissolved. A mixture of butyraldehyde (72 g, 1 mol, Aldrich) and isobutyraldehyde (72 g, 1 mol, Aldrich) is then added and the mixture is maintained at 40 °C until the majority of the aldehydes initially present have reacted. The basic catalyst is neutralized by careful addition of sulfuric acid, the salts are removed by filtration, and the solution is hydrogenated over Raney nickel at 100 °C, 5 MPa for 1 hour to give a mixture of 8-carbon 1,3-diols. The butanol and isobutanol formed during the hydrogenation are removed by distillation to give a mixture of 1,3-diols with 8 carbons namely: a mixture of 2,2,4-trimethyl-1,3-pentanediol, 2-ethyl-1,3-hexanediol ,

of 2,2-dimethyl-1,3-hexanediol and 2-ethyl-4-methyl-1,3-pentanediol. This mixture can be further purified by distillation under reduced pressure or decolorization with activated carbon. The obtained solvent is used for further diol syntheses.

If only butyraldehyde is used in the synthesis, the main product obtained is 2-ethyl-1,3-hexanediol.

If only isobutyraldehyde is used in the synthesis, the main product obtained is 2,2,4-trimethyl-1,3-pentanediol.

125.:,

Mixed condensation of butyraldehyde and methyl ethyl ketone and conversion to a mixture of 1,3-diols with eight carbon atoms

Method A n-Butanol (148 g, 2 moles, Aldrich) in a 500 mL three-necked flask equipped with a stirrer, internal thermometer, reflux condenser and connected to a source of nitrogen inert atmosphere is allowed to react with sodium metal (2.3 g, 0.1 mol, Aldrich) until its complete dissolution. A mixture of butyraldehyde (72 g, 1 mol, Aldrich) and 2-butanone (72 g, 1 mol, Aldrich) is then added and the mixture is maintained at 40 °C until the bulk of the butyraldehyde initially present has reacted. The basic catalyst is neutralized by careful addition of sulfuric acid, the salts are removed by filtration. Unreacted starting materials and solvent are optionally removed by distillation. The reaction mixture, containing the condensation products, is hydrogenated over Raney nickel at a temperature of 100 °C and a pressure of 5 MPa for 1 hour to form a mixture of 1,3-diols with 8 carbons, 2-ethyl-1,3-hexanediol, 2-ethyl- 3-methyl-1,3-pentanediol, 3,5-octanediol 3-methyl-3,5-heptanediol and smaller amounts of other isomeric 1,3-diols, e.g. 3-methyl-2,4-heptanediol and 3,4 -dimethyl-2,4-heptanediol. This mixture can be further purified by fractional distillation.

Method B

The synthetic procedure described above is used, with the difference that 2 moles of butyraldehyde are used for each mole of 2-butanone. This gives the reaction product by condensation of two diol molecules), and by condensation with a higher proportion of diols, resulting from butyraldehyde (i.e. 2-ethyl-1,3-hexanebutyraldehyde and 2-butanone (e.g.

2-ethyl-3-methyl-1,3-pentanediol and 3,5-octanediol), and a lower proportion of these diols, formed by the condensation of 2-butanone (e.g.

3-methyl-3,5-heptanediol and 3,4-dimethyl-2,4-hexanediol).

- 126

Method C

The synthetic procedure described above is used, with the difference that one mole of 2-butanone is placed in the reaction vessel together with the solvent and the catalyst, and one mole of butyraldehyde is gradually added. The reaction conditions are chosen such that the mutual condensation of 2-butanone is slow and the more reactive carbonyl of the aldehyde reacts immediately after addition. This gives a reaction product with a higher proportion of diols, formed by the condensation of 2-butanone with butyraldehyde and the mutual condensation of 2-butanone molecules, and a lower proportion of the diol formed by the mutual condensation of two butyraldehyde molecules.

Method D

Method C above is repeated at low temperatures. 1.0 mole of 2-butanone is dissolved in five times the volume of dry tetrahydrofuran. The obtained solution is cooled to -78 °C and 0.95 mol of potassium hydride is gradually added. After hydrogen evolution has ceased, the solution is allowed to stand for one hour to allow the more stable enol form to form, and then one mole of n-butyraldehyde is added slowly with vigorous stirring, maintaining the temperature at -78°C. After the addition of butyraldehyde is complete, the temperature of the solution is allowed to rise gradually to room temperature and the solution is neutralized by the careful addition of sulfuric acid. Salts are removed by filtration. Unreacted starting materials are eventually removed by distillation together with the used solvent. The obtained mixture, containing condensation products, is hydrogenated over Raney nickel at a temperature of 100 °C and a pressure of 5 MPa for 1 hour, which mainly yields a diol formed by condensation of the enol form of 2-butanone with butyraldehyde, i.e. 3,5-octanediol. Purification can be done by distillation.

127

Mixed condensation of isobutyraldehyde and methyl ethyl ketone and conversion to a mixture of 1,3-diols with eight carbon atoms

Method C described above is used, with the difference that butyraldehyde is replaced by isobutyraldehyde, condensation and reduction are carried out in an analogous manner, and the obtained diols are mainly 2,2,4-trimethyl-1,3-pentanediol, 2,2,3-trimethyl- 1,3-pentanediol, 2-methyl-3,5-heptanediol and 3-methyl-3,5-heptanediol.

Mixed condensation of butyraldehyde, isobutyraldehyde and methyl ethyl ketone and conversion to a mixture of 1,3-diols with eight carbon atoms

Method A described above is used, with the difference that a mixture consisting of one mole of butyraldehyde, isobutyraldehyde and 2-butanone is used. Condensation and reduction proceed analogously to form a mixture of 1,3-diols with eight carbons, which mainly consists of the following substances: 2,2,4-trimethyl-1,3-pentanediol, 2-ethyl-1,3-hexanediol, 2, 2-dimethyl-1,3-hexanediol, 2-ethyl-4-methyl-1,3-pentanediol, 2-ethyl-3-methyl-1,3-pentanediol, 3,5-octanediol, 2,2,3- trimethyl-1,3-pentanediol, 2-methyl-3,5-heptanediol and 3-methyl-3,5-heptanediol and in which smaller amounts of other isomers are also present, formed by the condensation of methylene 2-butanone instead of methyl.

Mixtures obtained by condensation of butyraldehyde, isobutyraldehyde and/or methyl ethyl ketone do not contain more than 90 wt.%, preferably do not contain more than 80 wt.%, more preferably do not contain more than 70 wt.%, even more preferably do not contain more than 60 wt.%, and most preferably do not contain more than 50% by weight, some certain compounds. The reaction mixtures used should not contain more than 95% by weight, preferably no more than 90% by weight, more preferably no more than 85% by weight, and most preferably no more than 80% by weight, of butyraldehyde or isobutyraldehyde.

- i2a

Method E

Preparation of 1,4-diols by the reaction of acetylides with carbonyl compounds

Disodium acetylide Na ^+- :CC:Na ⁺ reacts with aldehydes and ketones to form unsaturated alcohols, e.g.:

OH OH

2R-CO-CH ₃ + NaCsCNa--- R—C—C=C~ C— R

I I

CH ₃ CH ₃

The resulting diol with a triple bond is then partially reduced to a diol with a double bond, or it is completely reduced to a saturated diol. This reaction can also be carried out using an 18% suspension of monosodium acetylides with a carbonyl compound to form a triple-bonded alcohol, which can be converted to the sodium salt and reacted with another mole of carbonyl compound to form an unsaturated 1,4-diol. If a mixture of unsaturated carbonyl compounds with diacetylides is used, a mixture of diols is formed. Certain structures can be prepared in higher yields if monoacetylide is used.

Illustrative example: preparation of 6-methyl-2,5-heptanediol

Sodium acetylide (18% suspension in xylene) is allowed to react with isobutryaldehyde to form an alcohol with a triple bond (CH ₃ ) ₂ CH-CHO + NaC CHNa = (CH ₃ ) ₂ CH-CHOH-C CH

The resulting triple-bonded alcohol is converted by reaction with a base to sodium acetylide R-CHOH-C CNa, which is then allowed to react with an equimolar amount of acetaldehyde to form the triple-bonded diol R-CHOH-C C-CHOH-R'. This compound, (CH ₃ ) ₂ CH-CHOH-C C-CHOH-CH ₃ , can be isolated as an unsaturated diol, or it can be reduced by catalytic hydrogenation to the corresponding compound with a double bond instead of a triple bond,

- 129 can optionally be further reduced by catalytic hydrogenation to a saturated 1,4-diol.

Method F

Preparation of substituted diols derived from cyclic anhydrides, lactones and esters of dicarboxylic acids

This method of preparation is suitable for the preparation of diols, especially some 1,4-diols which are derivatives of dicarboxylic acid anhydrides, diesters and lactones, but is not limited to 1,4-diols or diacids with four carbons.

These types of diols are generally synthesized by reducing the corresponding anhydrides, lactones or diesters with sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al). This reducing agent is supplied as a 3.1 molar solution in toluene, and one mole of it yields one mole of hydrogen. Diesters and cyclic anhydrides require 3 moles of Red-Al per mole of substrate. Using an alkyl-substituted succinic anhydride derivative to illustrate this method, a typical reduction is carried out as follows:

The anhydride is first dissolved in anhydrous toluene and the solution is poured into a reaction vessel equipped with a dosing funnel, a non-mechanical stirrer, a thermometer and a reflux condenser, to which is attached a drying tube filled with calcium chloride or sodium hydroxide, preventing the access of atmospheric moisture, and carbon dioxide Solution in of toluene is poured into a dosing funnel and slowly added to the stirred anhydride solution. The ongoing reaction is exothermic and is carried out so that the temperature rises to 80°C. The temperature of 80 °C is maintained for a further time

- 13(1

• ·

• · ·· • · · · · • · · ·· ♦· about two hours during which the dosing is carried out.

The reaction mixture is then allowed to cool back to room temperature. The reaction mixture is then added to a stirred aqueous solution of HCl (concentration 20%), which is cooled in an ice-water bath and whose temperature is maintained between 20-30°C. After acidification, the phases of the reaction mixture are separated in a separatory funnel and the organic layer is washed with dilute salt solution to neutral pH. The synthesized 1,4-diol is obtained by drying this neutralized diol solution over anhydrous magnesium sulfate, filtration and vacuum stripping.

Method G

Preparation of diols with one or two secondary or tertiary hydroxyls

A general method of preparing substituted diols of lactones and/or diesters by alkylation of the carboxyl group(s) consists in the reaction of methylmagnesium bromide (Grignard reagent) with alkyllithium organometallic compounds, usually methyllithium. An example is the reaction:

OH

Θ

2CH3

C—CH3

CH3 ch ₂ -oh

This type of alkylation can also be performed with diesters. When an excess of methylating agent is used, diols are formed in which both hydroxyl groups are tertiary.

- 131·*·· ’· • ftftft ft · ftft «

Method Η

Preparation of substituted 1,3-, 1,4- and 1,5-diols

A general method for the preparation of certain 1,3-, 1,4-, and 1,5-diols uses the procedures described as Method A-1 and Method A-2. Cyclic alkadienes are used instead of cycloalkenes. The general formula of the starting material is

R in this formula is H or Ο-^Ο^alkyl and x is 1, 2, or 3. The reactions used are the same as in method A, with the difference that one mole of ethylene glycol is formed for each mole of the main solvent formed, as is the case, for example, in preparation of 2,2-dimethyl-1,4-hexanediol from 1-ethyl-5,5-dimethyl-1,3-cyclohexanediol (CAS No. 79419-18-4)

CH ₃

CHj—

AND

C—OH OH 1 ch ₃ -c^ ch ₂ c* ^c b C—OH 1 ch ₂ 1 1 c ₂ h ₅ 1 OH c ₂ h ₅

Preparation of polyethoxylated derivatives

Polyethoxylated derivatives of diol main solvents are usually prepared in high pressure reactors under a nitrogen atmosphere. A suitable amount of ethylene oxide is added at high temperature (80 to 170°C) to a mixture of diol solvent and potassium hydroxide. Calculate the amount of ethylene oxide needed in relation to the amount of diol solvent used so that for each

A« • A A

132 • AAAA

AA AA

A A A A A AAA

AAA ·

A A A

A· ·· molecule of diol was added by the desired number of ethylene oxide groups. After completion of the reaction, for example after 1 hour, the remaining unreacted ethylene oxide is removed by evacuation.

Illustrative example: preparation of the tetraethoxy derivative of 3,3-dimethyl-1,2-butanediol

354 g (3.0 moles) of 3,3-dimethyl-1,2-butanediol and 0.54 g of potassium hydroxide are fed into a two-liter Parr reactor with temperature control. The reactor is purged with nitrogen and evacuated three times to a pressure of 8 kPa. The reactor is then refilled with nitrogen to atmospheric pressure and heated to 130°C. The pressure in the reactor is then adjusted to a value slightly lower than the atmospheric pressure by a slight evacuation. Ethylene oxide (528 g 12.0 mol) was added over one hour while maintaining the temperature at 130°C. After another hour or so, the contents of the reactor are cooled to 90°C and any remaining ethylene oxide is removed by evacuation.

Preparation of polyethoxylated derivatives with a methyl end group

Polyethoxylated derivatives of diols with a methyl end group are usually prepared either by the reaction of methoxypoly(ethoxy)ethyl chlorides (i.e. CH3O-(CH ₂ CH ₂ O) _n -CH ₂ CH ₂ -Cl) of the desired chain length with the relevant diol, or by the reaction of polyethylene glycol with the end by a methyl group (ie CH ₃ O-(CH ₂ CH ₂ O) _n -CH ₂ CH ₂ -OH) of the desired chain length with an epoxy diol precursor, or a combination of these methods.

Illustrative examples:

Preparation of the tetraethoxy derivative of 2-methyl-2,3-butanediol with methyl end groups (CH ₃ ) ₂ C(OH)CH(CH ₃ )(OCH ₂ CH ₂ ) ₄ OCH3

In a liter three-necked boiling flask equipped with a magnetic stirrer, a reflux condenser, a thermometer and a system for regulation

- 133 • it • · • « • « ··· ·· ♦

• ···· i · ·· it · 1 • ·· »· it · <

• to 4 >· ♦· temperature (Thermowatch I ² R) ^R tetraethylene glycol methyl ether (208 g 1.0 mol) and sodium metal (Aldrich, 2.3 g, 0.10 mol) are added and this mixture is heated under an argon atmosphere to 100 °C. After the sodium dissolved, 2-methyl-2,3-epoxybutane (86 g, 1.0 mol) was added and the resulting solution was stirred overnight under argon at 120 °C. Using ¹² C-NMR (dmso-dg) the disappearance of the epoxide peak determines when the reaction is complete. The reaction mixture is cooled, poured into an equal volume of water, neutralized with 6N HCl saturated with sodium chloride, and extracted twice with dichloromethane. The combined dichloromethane layers were dried over sodium sulfate and the solvent was stripped to give the crude synthesized polyether alcohol. Purification by fractional vacuum distillation can also be carried out.

Preparation of methoxytriethoxyethyl chloride

Tetraethylene glycol methyl ether (208 g 1.0 mol) ^is added under argon to a liter three-necked flask equipped with a magnetic stirrer, a reflux condenser, a thermometer and a temperature control system (Thermowatch I ² R). Thionyl chloride (256.0 g, 2.15 mol) was added dropwise with vigorous stirring over 3 hours, maintaining the temperature at 50-60°C. The reaction mixture is then heated to 55 °C overnight. In the subsequent ^LO C-NMR (D ₂ 0) measurements, only a small peak at 60 ppm corresponding to unreacted alcohol and a prominent peak at 43 ppm belonging to the chlorinated product (-CH ₂ C1) are recorded. Sodium chloride solution is slowly added to the reaction mixture until the thionyl chloride decomposes. The reaction mixture is poured into about 300 ml of saturated sodium chloride solution and extracted with 500 ml of methylene chloride. The organic layer is dried and the solvent is stripped on a rotary evaporator to give crude methoxyethoxyethyl chloride. Purification by fractional vacuum distillation can be done.

- 134

9 • · • 9999 ·· • *9 9

9 99

999 9 9

9 9

99

Preparation of the tetraethoxy derivative of 2-methyl-1,3-pentanediol with methyl end groups C ₂ HgCH(OH)CH(CH ₃ )CH ₂ (OCH ₂ CH ₂ ) ₄ 0CH ₃

Alcohol C ₂ H ₅ CH(OH)CH(CH ₃ )CH ₂ OH (116 g, 1.0 mol) is added to a liter three-necked flask equipped with a magnetic stirrer, a reflux condenser and a temperature control system (Thermowatch ^R , I ² R) at the same time with 100 ml of tetrahydrofuran as solvent. Sodium hydride (32 g 1.24 mol) is gradually added to this solution and the mixture is refluxed until the evolution of gases ceases. Add methoxytriethoxyethyl chloride (242 g 1.2 mol, prepared as above) and reflux for 48 hours. The reaction mixture was cooled to room temperature and water was added dropwise with stirring to decompose excess hydride. Tetrahydrofuran is removed by stripping on a rotary evaporator. The crude product is dissolved in 400 ml of water, in which such an amount of sodium chloride was previously dissolved that an almost saturated solution was formed. The resulting mixture is then extracted twice with 300 ml of dichloromethane each time. The combined dichloromethane layers were dried over sodium sulfate and the solvent was stripped on a rotary evaporator to give the crude product. Purification can be carried out by further stripping of unreacted starting materials and low molecular weight products under vacuum at 150°C. Optional further purification by vacuum distillation yields the synthesized polyether.

Preparation of polypropoxy derivatives

A three-necked flask equipped with a magnetic stirrer cooled by solid C0 ₂ , a dosing funnel, a thermometer and a temperature control system (Therm-O-Watch, I2R) is used. Air is removed from the apparatus by blowing it with a stream of nitrogen, and a device for working under a nitrogen atmosphere is connected to it. Dry alcohol or diol to be propoxylated is added to the flask. Next, 0.1-5 mol% sodium metal is slowly added to the flask, heating the flask if necessary to dissolve the sodium. The reaction mixture is then heated to 80 to 130 °C and propylene oxide (Aldrich) is added dropwise from a dosing funnel • 99

9 · • ·Α

9 9

135 -Í :

999 ·

9999

9

at such a rate that there is slight reflux at the reflux condenser with solid C0 ₂ . The addition of propylene oxide is continued until the amount of propylene oxide corresponding to the desired degree of propoxylation is added. Heating is continued until reflux of propylene oxide ceases, and the temperature is then maintained at the same level for an additional hour to ensure complete reaction of the components of the reaction mixture. The reaction mixture is then cooled to room temperature and neutralized by careful addition of a suitable acid such as methanesulfonic acid. After removing the salts by filtration, the synthesized propoxylated product is obtained. The average degree of propoxylation is usually verified on the basis of a -'-H-NMR spectrum.

Preparation of polybutoxy derivatives

A three-neck hair dryer equipped with a magnetic stirrer, a cooler cooled by solid C0 ₂ , a dosing funnel, a thermometer and a temperature control system (Therm-O-Watch, I2R) is used. Air is removed from the apparatus by blowing it with a stream of nitrogen, and a device for working under a nitrogen atmosphere is connected to it. Dry alcohol or diol to be propoxylated is added to the flask. Next, 0.1-5 mol% sodium metal is slowly added to the flask, heating the flask if necessary to dissolve the sodium. The reaction mixture is then heated to 80-130°C and -butylene oxide (Aldrich) is added dropwise from a dosing funnel at such a rate that slight reflux occurs at the reflux condenser with CO ₂ . The addition of butylene oxide is continued until the amount of butylene oxide corresponding to the desired degree of propoxylation is added. Heating is continued until reflux of butylene oxide ceases, and the temperature is then maintained at the same level for an additional hour to ensure complete reaction of the components of the reaction mixture. The reaction mixture is then cooled to room temperature and neutralized by careful addition of a suitable acid such as methanesulfonic acid. After removing the salts by filtration, the synthesized propoxylated product is obtained. The average degree of propoxylation is usually verified on the basis of the H-NMR spectrum.

136 • this·· that·· · « • · <

• it ··

Preparation of polytetramethyleneoxy derivatives

0.1 mol of dry alcohol or diol is poured into a three-necked flask equipped with a magnetic stirrer, a cooler, a thermometer and a device for working under argon. If an average degree of tetramethyleneoxylation of one per hydroxyl group is desired, 0.11 mole of 2-(4-chlorobutoxy)tetrahydropyran (ICI) per mole of hydroxyl groups is added. If necessary, a solvent such as dry tetrahydrofuran, dioxane or dimethylformamide is added. Sodium hydride (in excess of 5 mol% relative to the chlorinated compound) is then added in small portions with vigorous stirring, keeping the temperature between 30 and 120°C. After the entire added amount of hydride has reacted, the temperature is maintained at the same level until all the hydroxyls are alkylated, usually 4 to 24 hours. After completion of the reaction, the reaction mixture is cooled and the excess hydride is decomposed by careful gradual addition of methanol. An equal volume of water is then added and the pH is adjusted to 2 by adding sulfuric acid. After heating to 40°C, which is maintained for 15 minutes to hydrolyze the tetrahydropyranyl protecting groups, the reaction mixture is neutralized with sodium hydroxide and the solvent is stripped on a rotary evaporator. The residue is taken up in ether or methylene chloride and the salts are removed by filtration. Stripping yields a crude tetramethyleneoxy alcohol or diol derivative. Further purification can be done by vacuum distillation. If the final average degree of tetramethyleneoxylation is to be less than one, a suitably lower amount of chlorinated compound and hydride is used. If it is necessary to achieve a higher average degree of tetramethyleneoxylation than one, the whole process is repeated cyclically until the desired degree of alkoxylation is reached.

Preparation of alkyl monoglyceryl ethers and aryl monoglyceryl ethers

A suitable method for the preparation of alkyl and/or aryl monoglyceryl ethers is preceded by the preparation of the corresponding alkyl glycidyl ether precursor. This is then converted to a ketal, which is further • · · ·· · ·

99

9 9 9

9 9

999 99

137

99 99

9 9 9 9 · • · · ·· _t · ·♦·· * • · · ♦ ···· ·· ·· hydrolyzes to monoglyceryl ether (diol). Next, an illustrative example of the preparation of the preferred n-pentyl monoglyceryl ether, (ie 3-(pentyloxy)-1,2-propanediol) nC ₅ ^h 11-°-CHOH-CH ₂ OH is presented.

Preparation of 3-(pentyloxy)-1,2-propanediol

546 g of 50% aqueous NaOH and 38.5 g of tetrabutylammonium bisulfate, which is a phase transfer catalyst (PTC), are added to a three-necked, two-liter flask (equipped with a top-drive stirrer, a water return cooler, a mercury thermometer, and a dosing funnel). . The contents of the flask are dissolved by stirring and then 200 g of 1-pentanol and about 400 ml of hexanes (a mixture of isomers with 85% n-hexane) are added. The dosing funnel is filled with 418 g of epichlorohydrin, which is then added slowly (dropwise) to the stirred reaction mixture. The temperature is gradually increased to 68 °C by the heat of reaction. After the entire amount of epichlorohydrin is added, the reaction is allowed to proceed for 1 hour (without external heating).

The crude reaction mixture is diluted with 500 mL of warm water, mixed gently, and then the aqueous layer is allowed to separate, which is subsequently separated. The hexane layer is diluted again with 1 liter of warm water while stirring, and the pH of the thus obtained mixture is adjusted to 6.5 by adding dilute aqueous sulfuric acid. The water layer is separated again and poured into the waste, and the hexane layer is then washed three times with water. The hexane layer was then separated and evaporated to dryness on a rotary evaporator to give the crude n-pentyl glycidyl ether.

Acetonation (Ketal conversion)

1 liter of acetone is poured into a three-necked two-liter flask (equipped with a top-drive stirrer, a water return cooler, a mercury thermometer, and a dosing funnel). 1 ml of SnCl ₄ is added to the acetone while stirring. 200 g of the just prepared n-pentyl glycidyl ether is added to the dosing funnel attached to this boiling flask. Glycidyl ether is added very slowly to the stirred acetone solution (addition rate is set ·· í <

··

138 • · ··· · • · · • ·♦·» ·* * so as to limit the rise in temperature caused by the heat of reaction). The reaction is allowed to proceed for 1 hour (at a maximum temperature of 52°C) after adding the entire amount of glycidyl ether.

Hydrolysis

The apparatus is adapted for distillation and equipped with a heating nest and a temperature regulator. The crude reaction mixture was concentrated by distilling off 600 ml of acetone. 1 liter of aqueous 20% sulfuric acid and 500 ml of a mixture of hexane isomers are added to the cooled concentrated solution. The contents of the flask are then heated to 50°C with stirring (the apparatus is adapted to condense and separate the released acetone). Hydrolysis is carried out as long as the analysis carried out by thin layer chromatography (Thin Layer Chromatography - TLC) proves the end of the reaction. The crude reaction mixture is cooled and the aqueous layer is separated and poured into the waste. The organic layer is then diluted with 1 liter of warm water and the pH is adjusted to 7 by adding dilute aqueous NaOH (1 N). The aqueous layer is separated again and the organic phase is extracted three times with water. The organic phase is then separated and evaporated on a rotary evaporator. The residue is diluted with a fresh batch of hexane isomers and the product is extracted into a methanol/water solution (70/30 by weight). The methanol/water solution is re-evaporated to dryness on a rotary evaporator (with the addition of methanol to promote water evaporation). Hot filtration of this residue through a glass fiber microfilter yields n-pentyl monoglyceryl ether.

Preparation of di(hydroxyalkyl) ethers

Preparation of bis(2-hydroxybutyl) ether

A three-necked flask with a volume of 500 ml, equipped with a magnetic stirrer, a thermometer, a dosing funnel, a return cooler, an argon supply and placed in a heating nest is blown through with argon. Then 1,2-butanediol (270 g, 3 mol, Aldrich) and sodium metal (1.2 g, 0.05 mol, Aldrich) are added and the sodium is allowed to dissolve. The reaction mixture is heated to 100 °C and, while stirring, after

139

• ···* ·· « · · • · « ·

·· ·· add epoxybutane (71 g, 1 mol, Aldrich) dropwise. Heating is continued until reflux of epoxybutane ceases and then heated for an additional 1 hour to achieve complete conversion. The reaction mixture is neutralized with sulfuric acid, the salts are removed by filtration, and the excess butanediol is removed by fractional distillation of the obtained liquid under reduced pressure. The synthesized ether is obtained as a distillation residue. This product can be further purified by vacuum distillation.

Preparation of bis(2-hydroxycyclopentyl)ether

A three-necked flask with a volume of 1 1, equipped with a magnetic stirrer, a thermometer, a dosing funnel, a return cooler, an argon supply and placed in a heating nest is blown through with argon. Then 1,2-cyclopentanediol (306 g, 3 mol, Aldrich) and a complex of boron fluoride with diethyl ether (0.14 g, 0.01 mol, a mixture of cis and trans isomers, Aldrich) are added dropwise while stirring. cyclopentene oxide (84 g, 1 mol, Aldrich) and the reaction mixture is maintained at 10-40 °C until all the cyclopentene oxide has reacted. The reaction mixture is neutralized with sodium hydroxide and the excess cyclopentanediol is removed by fractional distillation of the obtained liquid under reduced pressure. The synthesized ether is obtained as a distillation residue. This product can be further purified by vacuum distillation.

Some aspects of preparation

The above-mentioned main solvents B and some mixtures of main solvents B and secondary solvents enable the preparation of premixes containing the active substance of the preparation for fabric softening A (55 to 85 wt.%, preferably 60 to 80 wt.%, more preferably 65 to 75 wt.% , based on the total weight of the premix) the main solvent B (10% to 30% by weight, preferably 13 to 25% by weight, more preferably 15% to 20% by weight, based on the total weight of the premix) and optionally also the water-soluble solvent C ( 5 to 20 wt.%, preferably 5 to 17 wt.%, more preferably 5 to 15 wt.%, based on the total weight of the premix). Main solvents B • ·

- 140 may optionally be replaced by a mixture of an effective amount of the main solvent B and some of the above-mentioned solvents which are unsuitable in themselves. These premixes also contain the required amount of the active substance of fabric softener A, enough of the main solvent B, and possibly solvent C, which allows the premix to have a certain required viscosity at a certain required temperature range. Typical viscosities suitable for processing are below 1 Pa.s, preferably below 500 mPa.s, more preferably below 300 mPa.s. Working at low temperatures increases safety, minimizes solvent evaporation, minimizes degradation and/or loss of materials such as biodegradable fabric softener actives, perfumes, and the like, and reduces heating requirements, thereby saving processing costs. Additional protection of the fabric softener active ingredient can be provided, for example, by the presence of a chelating agent such as ethylenediaminepentaacetic acid during the preparation of the fabric softener active ingredient. The result is a reduction in the impact on the surrounding environment and an increase in the safety of the procedure used for preparation.

Examples of premixes and procedures for their use are premixes, the preparation of which is described in more detail in the following examples of embodiments of the invention, which contain 55 to 85%, preferably 60 to 80%, more preferably 65 to 75% of the active substance of the preparation for softening fabrics A, mixed with 10 to 30%, preferably with 13 to 25%, more preferably with 15 to 20% of a main solvent such as 1,2-hexanediol and 5 to 20%, preferably 5 to 15% of a suitable water soluble solvent C such as ethanol and/or isopropanol.

These premixes can be used for the preparation of finished preparations by a procedure consisting of the following steps:

1. Prepare a premix of the fabric softener active ingredient containing about 11% ethanol and about 17% of the main solvent and allow this premix to cool to room temperature.

2. Mixing perfume and premix.

3. Preparation of a mixture consisting of water and HCl at a temperature • ·

141 • · · · · · • · · · · · • · · · · • · · · · · · • · ·· ·· ·· rooms .

4. Addition of the premix to this aqueous mixture with intensive mixing.

5. Adjusting the viscosity of the solution to the desired value by adding CaCl ₂ solution.

6. Adding the dye solution and achieving the desired color.

For the preparation of premixes, suitable for the preparation of preparations according to the present invention, active substances of preparations for softening fabrics (DEQA), main solvents and possibly also water-soluble solvents can be used.

For commercial purposes, the clear preparations according to the present invention are filled into containers, specifically into bottles, especially into transparent bottles (although translucent bottles may also be used), made of polypropylene (which may, however, be replaced by glass, oriented polyethylene, and the like), whereby these the bottles have a light blue shade, which can compensate for any yellow coloring of the preparation, or the coloring of the preparation that may gradually develop during its storage (for short-term storage and for perfectly clear and colorless products, clear and colorless containers or containers of a different shade can be used), and further, the material of these bottles contains a UV absorber, which minimizes the effect of ultraviolet light on the material contained inside the bottles, especially on highly unsaturated active substances (these UV-absorbers can also be on the surface of the bottles). The overall effect of the transparency of the containers is that it makes it possible to demonstrate the clarity and colorlessness of the preparations and thus assure the customer of the quality of the product.

The above description of synthetic methods is illustrative only, intended to assist those skilled in the art in understanding the present invention and is not intended to limit its scope. Unless otherwise indicated, all concentration figures given in the description and examples of this invention are percentages, ratios and parts by weight, and all numerical limits are normal approximations. Relevant parts of all cited documents are incorporated herein by reference.

- 142

Examples of embodiments of the invention

The following tables show the content of individual fatty acyls in N,N-di(acyl-oxyethyl)-N,N-dimethylammonium chlorides (DEQA), which are suitable as active substances in fabric softening preparations according to the present invention.

acyl groups DEQA ¹ DEQA ² DEQA ³ DEQA ⁴ DEQA ⁵ C12 tracks tracks 0 0 0 C14 3 3 0 0 0 C16 4 4 5 5 5 C18 0 0 5 6 6 C14:1 3 3 0 0 C16:l 11 7 0 0 3 C18 :1 74 73 71 68 67 C18 :2 4 8 8 11 11 C18 :3 0 1 1 2 2 C20:l 0 0 2 2 2 C20 and above 0 0 2 0 0 unknown 0 0 6 6 7 overall 99 99 100 100 102 IV 86-90 88-95 99 100 95 cis/trans 20-30 20-30 4 5 5 TPU 4 9 10 13 13

TPU = total mass content of polyunsaturated acyl groups

- 143

acyl DEQA ⁸ groups DEQA ^b DEQA' C14 0 1 0 C16 11 25 5 C18 4 20 14 C14:1 0 0 0 C16:l 1 0 1 C18:l 27 45 74 C18 :2 50 6 3 C18 :3 7 0 0 other 0 3 3 overall 100 100 100 IV 125-138 56 is not known cis/trans (C18:1) is not known 7 is not known TPU 57 6 is not known

The following tables show the content of fatty acyls in N,N-di(acyl-oxyethyl)-Ν,Ν-dimethylammonium chlorides (DEQA) with branched acyls of higher fatty acids.

the acid from which the acyl is derived DEQA ¹⁰ DEQA ¹¹ DEQA ¹² isomyrist - 1-2 - myristic 7-11 0.5-1 - isopalmite 6-7 6-7 1-3 palmitic 4-5 6-7 - isostearic 70-76 80-82 60-66 stearic - 2-3 8-10 isoleum - - 13-17 oil - - 6-12 IV 3 2 7-12

144 • ·· · 9 origin of the acyl group designation of the active substance

DEQA ¹³

DEQA ¹⁴

DEQA ¹⁵

DEQA ¹⁶

DEQA ¹⁷

DEQA ¹⁸

DEQA ¹⁹

DEQA ²⁰

DEQA ²¹

DEQA ²²

DEQA ²³

DEQA ²⁴

DEQA ²⁵ branched fatty acid 1 branched fatty acid 2 branched fatty acid 3 branched fatty acid 4

-heptyldecanoic acid 9-methoxyoctadecanoic acid

10-methoxyoctadecanoic acid 9-isopropoxyoctadecanoic acid

10-isopropoxyoctadecanoic acid mixture of isomers of methoxyoctadecanoic acid phenyloctadecanoic acid methylphenyloctadecanoic acid phenoxyoctadecanoic acid 65:35 mixture of fatty acids used to prepare DEQA AND DEQA 65:35 mixture of fatty acids used to prepare DEQA AND DEQA

The following examples show compositions of clear or translucent products that have an acceptable viscosity.

The preparations shown in the following examples are prepared by first preparing a premix of the softener by mixing appropriate amounts of active substances based on branched DEQA and active substances based on unsaturated DEQA. If the active substances of the plasticizers are not liquid at room temperature, they can be heated to such a temperature that they melt, for example 55 to 66 °C. The active substance of the fabric softener is mixed using an IKA RW 25 ^R stirrer for 2 to 5 minutes at 150 rpm. Separately, mixing HCl with deionized (DI) water prepares an acid/water mixture at room temperature. If the fabric softener actives and/or the main solvent(s) are not liquid at room temperature and need to be heated for this reason, the acid/water mixture must also be heated to about 38°C and this temperature must be maintained

145 • · 0 0 0 • · · · 0 · 0 • · 0

00 00 by heating in a water bath. The main solvent(s) (heated if their melting point is above room temperature) are added to the plasticizer premix and this premix is mixed for 5 minutes. The acid/water batch is then added to the softener premix and mixed for 20 to 30 minutes or until the formulation is clear and homogeneous. If necessary, the preparation is then allowed to cool to room temperature.

Examples 1 to 6 product composition (weight%)

folders approx. no approx. No. 2 approx. No. 3 approx. No. 4 approx. No. 5 approx. No. 6 DEQA ² 19.9 - 15.3 - 32.5 - DEQA ⁸ - 19.9 - 15.3 - 32.5 DEQA ¹⁰ 10.7 10.7 15.3 15.3 17.5 17.5 ethanol - - - 2 2 2 1,2-hexanediol 18 18 18 18 28 28 HCl (pH 2-3.5) 0.005 0.005 0.005 0.005 0.005 0.005 rain, water the rest to 100%

DEQA = 85% active substance (ingredient) in ethanol solution ··· · * · ·· «

146

Examples 7 to 12

folders product composition (weight%) approx. No. 7 approx. No. 8 approx. No. 9 approx. No. 10 approx. No. ll approx. No. 12 DEQA ² 19.9 - - - 32.5 - DEQA ⁸ - - 19.9 19 - 19 DEQA ¹¹ 10.7 - - - - - DEQA ¹² - 28 - - - - DEQA ¹³ - - 5.4 - - - DEQA ¹⁴ - - 5.4 - - - DEQA ¹⁵ - - - 5 9 - DEQA ¹⁶ - - - 6 9 - DEQA ¹⁸ - - - - - 6 DEQA ¹⁹ - - - - - 6 1,2-hexanediol 18 15 18 18 28 18 ethanol - 1 - - - 1 perfume 1.2 1 1.2 1.35 2 1, HCl (pH 2-3.5) 0.005 0.005 0.005 0.005 0.005 0.005 rain, water the rest to 100%

DEQA = 85% of active substance (ingredient) in ethanol solution ·>· · 4 • · 4 ·· *·

- 147

Examples 13 to 18

folders product composition (weight%) approx. No. 13 approx. No. 14 approx. No. 15 approx. No. 16 approx. No. 17 approx. No. 18 DEQA ¹ 19.9 - - - - - DEQA ⁶ - 17 - - - - DEQA ⁸ - - 19.9 - - - DEQA ⁹ - - - - 19.9 19.9 DEQA ¹⁰ - 6.8 7 7 7 7 DEQA ¹¹ 5.3 - - - - - DEQA ²⁰ 5.3 - - - - - DEQA ²¹ - 6.8 - - - - DEQA ²² - - 3.7 - - - DEQA ²³ - - - 3.7 - - DEQA ²⁴ - - - - 3.7 - DEQA ²⁵ - - - - - 3.7 1,2-hexanediol 9 9 18 18 18 9 2-ethyl-1,3-hexane- diol 8 - - - - 9 2,2,4-trimethyl- -1,3-pentanediol - 9 - - - - ethanol 1.2 1.2 1.2 1.2 1.2 1.2 perfume 0.005 0.005 0.005 0.005 0.005 0.005 Distilled water the rest to 100%

DEQA = 85 active substances (ingredients) in ethanol solution

• · ···

148

Examples 19 to 21

folders product composition (weight%) approx. No. 19 approx. No. 20 approx. No. 21 DEQA ²⁴ 30 - 15 DEQA ²⁴ - 30 15 1,2-hexanediol 18 18 18 HCl (pH 2-3.5) 0.005 0.005 0.005 Distilled water rest to 100%

DEQA = 85% active substance (ingredient) in ethanol solution

The above preparations are clear or transparent products with an acceptable viscosity.

Preparations according to examples 22 to 27 are prepared at room temperature as follows:

1. An aqueous solution containing HCl is prepared.

2. Separately mix the perfume and Tenox with the diester active ingredient of the fabric softener.

3. While stirring, the mixture containing the diester active substance is added to the aqueous batch with HCl.

4. About halfway through the addition of the diester active substance, 10 to 20% of the CaCl ₂ solution is added.

5. After the addition of the active substance is finished, the remainder of the CaCl ₂ solution is added while stirring.

149

0 0 · • 0 0·

0 0 ·

0 0 *0 00

Examples 22 to 27

folders product composition (weight%) approx. No. 22 approx. No. 23 approx. No. 24 approx. No. 25 approx. No. 26 approx. No. 27 DEQA ¹ 18 - 15 - - - DEQA ¹ - 18 - 12 - - DEQA ¹⁰ 9.2 9.2 15 12 - - DEQA ¹⁰ - - - - 20.8 - DEQA ¹⁰ - - - - - 28 perfume 1.35 1.35 1.35 1.35 1.35 1.35 Tenox 6 0.04 0.04 0.04 0.04 0.04 0.04 CaCl ₂ (25% solution) 2 2 2 2 2 2 HCl IN 0.30 0.30 0.30 0.30 0.30 0.30 Distilled water residue up to 100 %

DEQA = 85% active substance (ingredient) in ethanol solution

The above preparations are effective dispersion preparations with good stability.

Claims (15)

PATENT CLAIMS 1. Biodegradable fabric softening agents selected from the group consisting of 1. a substance of the general formula: (R) 44N N (+) - _[(CH2) n YR @ ¹ l _m (1) wherein R is hydrogen or a short chain alkyl or hydroxy C ^ -olefin, m is 2 or 3, n is 1-4, Y is -O- (O) O-, - (R) N- (O) C-, -C (O) -N (R) - or -O (O) -O-, and when Y is -0 - (0) O- or - (R) N- (O) C-, the total number of carbon atoms in the group R ¹ plus one is 6 to 22, but only in one of the two groups R ¹ or YR ¹ may the number be carbons less than 12, in which case the number of carbons in the second of the two groups is at least 16, R ¹ is an unsaturated or branched C ₅ -C ₂₁ alkyl which may be substituted, wherein the ratio of branched alkyl to unsaturated alkyl is 5:95 to 95: 5, and in the case of an unsaturated alkyl group, the iodine number of the fatty acid belonging to that group R ^{1 is from} 20 to 140, and the counterion X may be any anion compatible with the cation thereof; 2. a substance of the general formula: RN (+) CH 2 CH ³ CH _{2 Y} R1 (2) wherein Y, R, R ¹ and X have the same meaning ^^ as above. 3. mixtures of these substances, where: it may contain up to 20% of molecules whose chains are all the same length and in which one of the groups is 151 · · · · · · · · · · · · · · · · · · OH · ♦♦♦♦ -OH, -N (R) H or -C (O) OH and R is preferably hydrogen or an alkyl or hydroxyalkyl group of C 1 -C 6, n is preferably 2, Y is preferably -O- (O) C-, the total number of carbon atoms in R ¹ plus one is preferably 12 to 22 and R is preferably branched or unsaturated alkyl, wherein the ratio of branched alkyl to unsaturated alkyl is preferably 75:25 to 25:75, the iodine number of the unsaturated alkyl groups of the respective fatty acid of this group R ¹ is preferably 50 to 130, and counterion X is preferably selected from the group consisting of chloride, bromide, methylsulfate, ethylsulfate, sulfate and nitrate, R is more preferably selected from the group consisting of methyl, ethyl, propyl, hydroxyethyl and benzyl, m is more preferably 2, the total number of carbon atoms in R ¹ plus one is more preferably 13 to 19 and R ¹ is branched or unsaturated alkyl, to unsaturated alkyls is 50:50 to 30:70, the iodine number of the unsaturated alkyl groups of the respective fatty acid of this group R ¹ is more preferably 70 to 115, and counterion X is more preferably chloride. 2. The fabric softener according to claim 1 characterized in that its formula is (R) 4 <nn ⁽⁺ i - ^[(1-YR CH2in] m (I) wherein R is hydrogen or a short alkyl or hydroxyalkyl chain of C ₁ -C 8, m is 2 or 3, Y is -O- (O) C-, the total number of carbon atoms in R ¹ plus one is 6 to 22, but only in one of these two groups R ¹ or YR ¹ , the number of carbons may be less than 12, in which case the number of carbons in the second group is at least 16, R ¹ is an unsaturated or branched ^C 5 - ^C 21 alkyl ^which may be substituted, wherein the ratio of branched alkyl to unsaturated alkyl is 75:25 to 25:75, and in the case of 152. The unsaturated alkyl group is the iodine number of the fatty acid belonging to that group R ¹ 50 to 130, 152. R is preferably hydrogen or an alkyl or hydroxyalkyl group of C ₁ -C _3, n is 2, the total number of carbon atoms in ^R1 plus one is preferably from 12 to 22, and X is preferably selected from the group consisting of chloride, bromide, methylsulfate, , ethyl sulphate, sulphate and nitrate, R is more preferably selected from the group consisting of methyl, ethyl, propyl, hydroxyethyl, and benzyl, m is preferably 2, the total number of carbon atoms in R ¹ plus one is more preferably 14 to 20, and R ¹ is branched or unsaturated alkyl of 13 to 19, wherein the ratio of branched alkyl to unsaturated alkyls is 50:50 to 30:70, and wherein the iodine number of the unsaturated alkyl groups of the respective fatty acid of this R ¹ group is more preferably 70 to 115 and the counterion, X ^- is more preferably chloride. The fabric softening agent according to claim 1 or 2, characterized in that it consists of mixtures of compounds containing either 1) a predominantly branched alkyl group R ¹ , or 2) a predominantly unsaturated alkyl group R ¹ . The fabric softening agent according to claim 1 or 2, characterized in that it consists of compounds containing mixtures of either 1) predominantly branched alkyl groups R ¹ , or 2) predominantly unsaturated alkyl groups R ¹ . 5. A fabric softening composition comprising A. 2 to 80 wt.%, Preferably 13 to 75 wt.%, More preferably 15 to 70 wt.% Of the biodegradable fabric softener active selected from the group consisting of: 1. a substance of the general formula: (R) 4Hn-N ( ⁺ ) - [(GH ² ) n V R ¹¹ ! _m (1) ·· 99 9 9 9 • 9 99 . 9 9999 9 9 9 · ·· · 9 • 153 9 9 9 9 wherein R is hydrogen or a short chain alkyl or hydroxy C ₁ -C _6, m is 2 or 3, n is 1-4, Y is -O- (O) C-, - (R) N - (O) C-, -C (O) -N (R) - or -C (O) -O-, and when Y is -O- (O) C- or - (R) N- (O ) C-, the total number of carbon atoms in the group R ¹ plus one is 6 to 22, but only in one of the two groups R ¹ or YR ^{1 the} number of carbons may be less than 12, in which case the other is groups of carbon number of at least 16, R ¹ is branched alkyl or unsaturated ^C 5 ^_C 21 'which may be substituted, the ratio of branched alkyl to unsaturated alkyls is 5:95 to 95: 5, and in the case of unsaturated alkyl groups, the iodine Value of fatty acids belonging to this group R ¹ 20 to 140, and the counterion X may be any anion compatible with the cation thereof; 2. a substance of the general formula: RN ( ^4- ) CH ₂ CH X ⁽ -) ³ ^ CH ₂ yr 1 (2) 1 (-) wherein Y, R, R, and X ^k 'have the same meaning as above. 3. mixtures of these substances, where: R is preferably hydrogen or a C 1 -C 4 alkyl or hydroxyalkyl group, n is preferably 2, Y is preferably -O- (O) C-, the total number of carbon atoms in R ¹ plus one is preferably 12 to 22 and R is preferably branched or unsaturated alkyl, wherein the ratio of branched alkyl to unsaturated alkyl is preferably 75:25 to 25:75, the iodine number of the unsaturated alkyl groups of the respective fatty acid of this group R ¹ is preferably 50 to 130, and counterion X "Is preferably selected from the group consisting of chloride, bromide, methylsulfate, ethylsulfate, sulfate and nitrate, R is more preferably selected from the group consisting of methyl, ethyl, propyl, hydroxyethyl and benzyl, m is more preferably 2, the total number of carbon atoms in R ¹ plus one is more preferably 14 154 · -z 20 and R ^x is a branched or unsaturated alkyl having a carbon number of 13 to 19, wherein the ratio of branched alkyl to unsaturated alkyl is 50:50 to 30:70, the iodine number of the unsaturated alkyl groups of the respective fatty acid of this R ¹ being more preferably 70 to 115 and counterion X ^- is more preferably chloride; whose components may further be B. principal solvent with a ClogP of 0.15 to 0.64 in an amount corresponding to less than 40% by weight, based on the total weight of the formulation; C. low molecular weight water-soluble solvents selected from the group consisting of ethanol, isopropanol, propylene glycol, 1,3-propanediol, propylene carbonate and mixtures of these solvents contained in the preparation in an effective amount sufficient to improve the clarity of the preparation, and the concentrations of the individual solvents are not so high that, in the absence of others, they can form clear preparations; D. an effective amount of a water-soluble calcium or magnesium salt sufficient to improve the clarity of the formulation; and whose remainder is formed fabrics according to Claim 9 E. water. 6. Preparation for softening mark i by that it contains 15 up to 70% said fabric softening active ingredient, said fabric softening active ingredient having the general formula: (R 10 -m-NM-KChyn-Y-Rln (1) where R is hydrogen or a short alkyl or hydroxyalkyl chain of C 1 -C 8, m is 2 or 3, Y is -O- (O) C-, the total number of carbon atoms in the group R ¹ plus one is 6 to 22, but only in one 155 of 1 of 4 of these two. the groups R ^1, or YR ¹ may be a carbon number less than 12, and in this case, is the second of the two groups of carbon number of at least 16, R ¹ is an unsaturated or branched alkyl, ^C 5 ^_C 21 ^{'Y m} ay be substituted and the ratio of branched alkyl to unsaturated alkyls is 5:95 to 95: 5, and in the case of unsaturated alkyl groups, the iodine Value of fatty acids belonging to this group R ¹ from 50 to 130, R is preferably hydrogen or an alkyl or hydroxyalkyl group n is 2, the total number of carbon atoms in R ¹ plus one is preferably 12 to 22, and counterion X is selected from the group consisting of chloride, bromide, methylsulfate, ethylsulfate, sulfate and nitrate; R is more preferably selected from the group consisting of methyl, ethyl, propyl, hydroxyethyl, and benzyl, m is preferably 2, the total number of carbon atoms in R ¹ plus one is more preferably 14 to 20, and R ¹ is branched or unsaturated alkyl of 13 to 19, wherein the ratio of branched alkyl to unsaturated alkyl is 50:50 to 30:70, the iodine number of the unsaturated alkyl groups of the respective fatty acid of this R ¹ group is preferably 70 to 115 and the counterion X "is preferably chloride; Fabric softening composition according to claim 5 or 6, characterized in that said ClogP value is 0.25 to 0.62, preferably 0.40 to 0.60. The fabric softening composition according to any one of claims 5 to 7, characterized in that at low water concentrations of 5 to 15%, the ratio of the fabric softening composition to the main solvent is 55:45 to 85:15. , preferably 60:40 to 80:20, at water concentrations of 15 to 70%, the ratio of the fabric softening agent to the main solvent is 45:55 to 70:30, preferably 55:45 to 70:30, and at high water concentrations of 70 to 80%, the ratio of the fabric softening agent to the main solvent is 30:70 to 55:45, preferably 35:65 to 45:55. 9. A fabric softener composition according to any one of »» 156 ·· r a • ft ftft a Ftft according to claims 5 to 8, characterized in that it is selected from the group consisting of: I. alcohols and n-propanol and / or b. 2-butanol and / or 2-methyl-2-propanol; II. isomers of hexanediol including: 2,3-dimethyl-2,3-butanediol, 2,3-dimethyl-1,2-butanediol, 3,3-dimethyl-1,2-butanediol, 2-methyl-2,3-pentanediol, 3-methyl-2,3-pentanediol, 4-methyl-2,3-pentanediol, 3,4-hexanediol-2,3-hexanediol; -1,2-butanediol, 2-methyl-1,2-pentanediol, -1,2-pentanediol, 4-methyl-1,2-pentanediol, and / or diol; III. isomers of heptanediol including: 2-butyl-1,3-propanediol, 2,2-diethyl-1,3-propanediol, 1,3-propanediol, 2- (1-methylpropyl) -1,3-propanediol, 2- (2-methylpropyl) -1,3-propanediol, 2-methyl-2-propyl-1,2-butanediol, 2,3,3-trimethyl-1,4-butanediol, 2-ethyl-2-methyl-1,4-butanediol, 2-ethyl-3-methyl- 1,4-butanediol, 2-propyl-1,4-butanediol, 2-isopropyl-1,4-butanediol, 2,2-dimethyl-1,5-pentanediol, 2,3-dimethyl-2,4-dimethyl-1, 5-pentanediol, 2,3-dimethyl-2,3-pentanediol, 3,4-dimethyl-2,3-pentanediol, 2,3-dimethyl-3,4-pentanediol, 2-methyl-1,6-hexanediol, -hexanediol, 2-methyl-2,3-hexanediol, 3-methyl-2,3-hexanediol, 4-methyl-2,3-hexanediol, 5-methyl-2,3-hexanediol, 2-methyl-1,5 -pentanediol, -1,5-pentanediol, -2,3-pentanediol, -2,3-pentanediol, -pentanediol, 2-ethyl-3-methyl-1,2-hexane-3,3-dimethyl-2,4-dimethyl-4,4-dimethyl-2-ethyl-1,53-methyl-1,6-3,4-hexanediol, 1,3-heptanediol, 3-methyl-3,4-heptanediol, 1,5-heptanediol, and / or 1,6-heptanediol; IV. isomers of octanediol including: 2- (2-methylbutyl) -1,3-propanediol, 2- (1,1-dimethylpropyl) -1,3-propanediol, 2- (1,2-dimethylpropyl) -1,3-propanediol, 2- (1-ethylpropyl) 1,3-propanediol, 2- (1-methylbutyl) -1,3-propanediol, 2- (2,2- di-1,3-propanediol, 2- (3-methylbutyl) -1,32-butyl-2-methyl-1,3-propanediol, 2-ethyl-2-isopropyl-1,3-propanediol, 2-ethyl-2- propyl-1,3-propanediol, 2-methyl-2- (1-methylpropyl) -1,3-propanediol, 2-methyl-2- (2-methylpropyl) -1,3-propanediol, 2-tert-butyl -2-methyl-1,3 methylpropyl) -propanediol, ΦΦ · φ φ φ φ φ φ φ φ φ φ V * φ * 157 -propanediol, 2,2-diethyl-1,3-butanediol, 2- (1-methylpropyl) -1,3-butanediol, 2-butyl-1,3-butanediol, 2-ethyl-2,3-dimethyl-1 , 3-butanediol, 2- (1,1-dimethylethyl) -1,3-butanediol, 2- (2-methyl-propyl) -1,3-butanediol, 2-methyl-2-isopropyl-1,3-butanediol 2-methyl-2-propyl-1,3-butanediol, 3-methyl-2-isopropyl-1,3-butanediol, 3-methyl-2-propyl-1,3-butanediol, 2,2-diethyl-1,4-butanediol, 2-methyl-2-propyl-1,4-butanediol, 2- (1-methylpropyl-1,4-butanediol), 2-ethyl-2,3-dimethyl-1 4-butanediol, 2-ethyl-3,3-dimethyl-1,4-butanediol, 2- (1,1-dimethylethyl) -1,4-butanediol, 2- (2-methylpropyl-1,4-butanediol), 2-methyl-3-propyl-1,4-butanediol, 3-methyl-2-isopropyl-1,4-pentanediol, 2,2,3-trimethyl-1,3-pentanediol, 2,2,4-trimethyl-1,3-pentanediol, 2,3,4-trimethyl-1,3-pentanediol, 2,4,4-trimethyl-1,3-pentanediol, 3,4,4-trimethyl-1, 3-pentanediol, 2,2,3-trimethyl-1,4-pentanediol, 2,2,4-trimethyl-1,4-pentanediol, 2,3,3-trimethyl-1,4-pentanediol, 2,3, 4-trimethyl-1,4-pentanediol, 3,3,4-trimethyl-1,5-pentanediol, 2,2,3-trimethyl-1,5-pentanediol, 2,2,4-trimethyl-1,5-pentanediol, 2,3,3-trimethyl-1,5-pentanediol, 2,3,4-trimethyl- 2,4-pentanediol, 2,3,3-trimethyl-2,4-pentanediol, 2,3,4-trimethyl-1,3-pentanediol, 2-ethyl-2-methyl-1,3-pentanediol, 2-ethyl-3-methyl-1,3-pentanediol, 2-ethyl-4-methyl-1,3-pentanediol, 3-ethyl-2-methyl-1,4-pentanediol, 2-ethyl-2-methyl1. 4-pentanediol, 2-ethyl-3-methyl-1,4-pentanediol, 2-ethyl-4-methyl-1,4-pentanediol, 3-ethyl-2-methyl-1,4-pentanediol, 3-ethyl-3-methyl-1,5-pentanediol, 2-ethyl-2-methyl-1,5-pentanediol, 2-ethyl-3-methyl-1,5-pentanediol, 2-ethyl-4-methyl- 1,5-pentanediol, 3-ethyl-3-methyl-2,4-pentanediol, 3-ethyl-2-methyl-1,3-pentanediol, 2-isopropyl-1,3-pentanediol, 2-propyl-1, 4-pentanediol, 2-isopropyl-1,4-pentanediol, 2-propyl-1,4-pentanediol, 3-isopropyl-1,5-pentanediol, 2-isopropyl-2,4-pentanediol, 3-propyl-1,3- hexanediol, 2,2-dimethyl-1,3-hexanediol, 2,3-dimethyl-1,3-hexanediol, 2,4-dimethyl-1,3-hexanediol, 2,5-dimethyl-1,3-hexanediol, 3,4-dimethyl-1,3-hexanediol, 3,5-dimethyl-1,3-hexanediol, diol, 2,2-dimethyl-1,4-hexanediol, diol, 2,4-dimethyl-1,4- hexanediol, 4,5-dimethyl-1,4-hexane 2,3-dimethyl-1,4-hexane 2,5-dimethyl-1,4-hexane 4 158-diol, 3,3-dimethyl-1,4-hexanediol, 3,4-dimethyl-1,4-hexanediol, 3,5-dimethyl-1,3-hexanediol, 4,4-dimethyl-1,4- hexanediol, 4,5-dimethyl-1,4-hexanediol, 5,5-dimethyl-1,5-hexanediol, 2,2-dimethyl-1,5-hexanediol, methyl-1,5-hexanediol, methyl-1, 5-hexanediol, methyl-1,5-hexanediol, methyl-1,6-hexanediol, methyl-1,6-hexanediol, methyl-1,6-hexanediol, 2, 3, 2, 2, 3, 4- di3-di5-di2-di4-di3-di3-dimet5-dimethyl-4-dimethyl4,5-dimethyl2,3-dimethyl2,5-dimethyl2,3-dimethyl-1,5-hexanediol, 2,5-dimethyl-1,5-hexanediol, 3,4-dimethyl-1,5-hexanediol, 4,5-dimethyl-; 1,6-hexanediol, 2,3-dimethyl-1,6-hexanediol, 2,5-dimethyl-1,6-hexanediol, 3,4-dimethyl-2,4-hexanediol, 2-yl-2,4-hexanediol, 2,4-dimethyl-2,4-hexanediol, 2-thyl-2,4-hexanediol, 3,3-dimethyl-2, 4-hexanediol, 2,4-hexanediol, 3,5-dimethyl-2,4-hexanediol, -2,4-hexanediol, 5,5-dimethyl-2,5-hexanediol, -2,5-hexanediol, 2,4-dimethyl-2,5-hexanediol, -2,5-hexanediol, 3,3-dimethyl-2,5-hexanediol, 3,4-dimethyl-2,6-hexanediol, 3,3-dimethyl-1,3-hexanediol, 2-ethyl-1,3-hexanediol , 4-ethyl-1,4-hexanediol, 2-ethyl-1,4-hexanediol, 4-ethyl-1,5-hexanediol, 2-ethyl-2,4-hexanediol, 3-ethyl-2,4-hexanediol , 4-ethyl-2,5-hexanediol, 3-ethyl-1,3-heptanediol, 2-methyl-1,3-heptanediol, 3-methyl-1,3-heptanediol, 4-methyl-1,3-heptanediol, 5-methyl-1,3-heptanediol, 6-methyl-1,4-heptanediol, 2-methyl-1,4-heptanediol, 3-methyl-1,4-heptanediol, 4-methyl-1,4-heptanediol, 5-methyl-1,4-heptanediol, 6-methyl-1,5-heptanediol, 2- methyl-1,5-heptanediol, 3-methyl-1,5-heptanediol, 4-methyl-1,5-heptanediol, 5-methyl-1,5-heptanediol, 6-methyl-1,5-heptanediol, 2-methyl-1,6-heptanediol, 3-methyl-1,6-heptanediol, 4-methyl-1,6-heptanediol, 5-methyl-1,6-heptanediol, 6-methyl-1,6-heptanediol, 2-methyl-2,4-heptanediol, 3-methyl-2,4-heptanediol, 4-methyl-2,4-heptanediol, 5-methyl-2,4-heptanediol, 6-methyl-2,4-heptanediol, 2-methyl-2,5-heptanediol, 3- methyl-2,5-heptanediol, 4-methyl-2,5-heptanediol, 5-methyl-2,5-heptanediol, 6-methyl-2,5-heptanediol, 2-methyl-2,6-heptanediol, 3-methyl-2,6-heptanediol, 4-methyl-2,6-heptanediol, 3-methyl-3,4-heptanediol, 2-methyl-3,5-heptanediol, 3-methyl-3,5-heptanediol, 4-methyl-3,5-2,4-octanediol, 2,5-octanediol, 2,6-octanediol, • - 159 2,7-octanediol, 3,5-octanediol, and / or 3,6-octanediol; V. nonandiol isomers including: 2,3,3,4-tetramethyl-2,4-pentanediol, 3-tert-butyl-2,4-pentanediol, 2,5,5-trimethyl-2,4-hexanediol, 3 , 3,4-trimethyl-2,4-hexanediol, 3,3,5-trimethyl-2,4-hexanediol, 3,5,5-trimethyl-2,4-hexanediol, 4,5,5-trimethyl-2 , 4-hexanediol, 3,3,4-trimethyl-2,5-hexanediol, and / or 3,3,5-trimethyl-2,5-hexanediol, VI. glyceryl ethers and / or di (hydroxyalkyl) ethers including: 3- (n-pentyloxy) -1,2-propanediol, 3- (2-pentyloxy) -1,2-propanediol, 3- (3-pentyloxy) -1,2-propanediol, 3- (2-methyl-1) -butyloxy) -1,2-propanediol, 3- (iso-amyloxy) -1,2-propanediol, 3- (3-methyl-2-butyloxy) -1,2-propanediol, 3- (cyclohexyloxy) -1, 2-propanediol, 3- (1-cyclohex-1-enyloxy) -1,2-propanediol, 2- (pentyloxy) -1,3-propanediol, 2- (2-pentyloxy) -1,3-propanediol, 2- (3-pentyloxy) -1,3-propanediol, 2- (2-methyl-1-butyloxy) -1,3-propanediol, 2- (iso-amyloxy) -1,3-propanediol, 2- (3-methyl) -2-butyloxy) -1,3-propanediol, 2- (cyclohexyloxy) -1,3-propanediol, 2- (1-cyclohex-1-enyloxy) -1,3-propanediol, triethoxylated 3- (butyloxy) -1 , 2-propanediol, tetraethoxylated 3- (butyloxy) -1,2-propanediol, pentaethoxylated 3- (butyloxy) -1,2-propanediol, hexaethoxylated 3- (butyloxy) -1,2-propanediol, heptaethoxylated 3- (butyloxy) -1,2-propanediol, octaethoxylated 3- (butyloxy) -1,2-propanediol, nonethoxylated 3- (butyloxy) -1,2-propanediol, monopropoxylated 3- (butyloxy) -1,2-propanediol, dibutyle of non-methoxylated 3- (butyloxy) -1,2-propanediol, tributylenethoxylated 3- (butyloxy) -1,2-propanediol, 3-phenyloxy-1,2-propanediol, 3-benzyloxy-1,2-propanediol, 3- (2 -phenylethyloxy) -1,2-propanediol, 3- (1-phenyl-2-propanyloxy) -1,2-propanediol, 2- (m-cresyloxy) -1,3-propanediol, 2-phenyloxy-1,3-propanediol, 2- (p-cresyloxy) -1,3-propanediol, benzyloxy-1,3-propanediol, 2- (2-phenylethyloxy) -1,3-propanediol, 2- (1-phenylethyloxy) -1,3-propanediol, bis (2-hydroxybutyl) ether, and / or bis (2-hydroxycyclopentyl) ether; VII. saturated and unsaturated alicyclic diols and their derivatives including: (a) saturated diols and their derivatives, including: 1-isopropyl-1,2-cyclobutanediol, 3-ethyl-4-methyl-1,2-cyclob. 160 cyclohexanemethanol, -1,2-cyclohexanediol, tandiol, 3-propyl-1,2-cyclobutanediol, 3-isopropyl-1,2-cyclobutanediol, 1-ethyl-1,2-cyclopentanediol, 1,2-dimethyl-1 , 2-cyclopentanediol, 1,4-dimethyl-1,2-cyclopentanediol, 2,4,5-trimethyl-1,3-cyclopentanediol, 3,3-dimethyl-1,2-cyclopentanediol 3,4-dimethyl-1,2-cyclopentanediol, 3,5-dimethyl-1,2-cyclopentanediol, 3-ethyl-1,2-cyclopentanediol, 4,4-dimethyl-1,2-cyclopentanediol, 4-ethyl-1,2- cyclopentanediol, 1,1-bis (hydroxymethyl) cyclohexane, 1,2-bis (hydroxymethyl) cyclohexane, 1,2-dimethyl-1,3-cyclohexanediol, 1,3-bis (hydroxymethyl) cyclohexane, 1,3-dimethyl-1,3-cyclohexanediol, 1,6-dimethyl-1,3-cyclohexanediol, 1-hydroxy-cyclohexanethanol, 1-hydroxy-1-ethyl-1,3-cyclohexanediol, 1-methyl-2,2-dimethyl-1,3-cyclohexanediol, 2,3-dimethyl-1,4-cyclohexanediol, 2,4-dimethyl-1,3-cyclohexanediol, 2,5-dimethyl-1,3-cyclohexanediol, 2,6-dimethyl-1,4-cyclohexanxanediol, 2-ethyl-1,3-cyclohexanediol, 2-hydroxycyclohexanethanol, 2-hydroxyethyl-1-cyclohexanol, 3-hydroxyethyl-1- cyclohexanol, 3-hydroxycyclohexanethanol, 3-hydroxymethylcyclohexanol, 3-methyl-1,2-cyclohexanediol, 4,4-dimethyl-1,3-cyclohexanediol, 4,5-dimethyl-1,3-cyclohexanediol, 4,6-dimethyl- 1,3-cyclohexanediol, 4-ethyl-1,3-cyclohexanediol, 4-hydroxyethyl-1-cyclohexanol, 4-methyl-1,2-cyclohexanediol, 5.5-dimethyl-1,3-cyclohexanediol, 5-ethyl-1,3-cyclohexanediol, 1,2-cycloheptanediol, 2-methyl-1,3-cycloheptanediol, 2-methyl-1,4-cycloheptanediol, 4-methyl-1,3-cycloheptanediol, 5-met5-methyl-1,4-cycloheptanediol, 6-methyl, 3-cyclooctanediol, 1,4-cyclooctanediol, 1,5-cyclooctanediol, 1,2-cyclohexanediol diethoxylate, 1,2-cyclohexanediol triethoxylate, tetraethoxylate 1,2-cyclohexanediol, 1,2-cyclohexanediol pentaethoxylate, 1,2-cyclohexanediol hexaethoxylate, 1,2-cyclohexanediol heptaethoxylate, 1,2-cyclohexanediol octaethoxylate, nonaethoxylate 1,2-cyclohexanediol, 1,2-cyclohexanediol monopropoxylate, 1,2-cyclohexanediol monobutyleneoxylate, dibutyleneoxylate 1,2-cyclohexanediol, and / or 1,2-cyclohexanediol tributyleneoxylate, and (b) unsaturated alicyclic diols including: 1-ethenyl-2-ethylethyl-1,3-cycloheptanediol, hyl-1,4-cycloheptanediol, - 161 -1,2-cyclobutanediol, 1,2,3,4-tetramethyl-3-cyclobutene-1,2-diol, 3,4-diethyl-3-cyclobutene-1,2-diol, 3- (1,1- dimethylethyl) -3-cyclobutene-1,2-diol, 3-butyl-3-cyclobutene-1,2-diol, 1,2-dimethyl-4-methylene-1,2-cyclopentanediol, 1-ethyl-3-methylene-1,2-cyclopentanediol, 4- (1-propenyl) -1,2-cyclopentanediol, 3-cyclopentene-1,2-diol, 1-ethyl-3-methyl-1,2-cyclohexanediol, 1-ethenyl-; 1,2-cyclohexanediol, 1-methyl-3-methylene-; 1,2-cyclohexanediol, 1-methyl-4-methylene-1,2-cyclohexanediol, 3-ethenyl-1,2-cyclohexanediol, 4-ethenyl-3-cyclohexene-1,2-diol, 2,6-dimethyl-3-cyclohexene-1,2-diol, 6,6-dimethyl-4- cyclohexene-1,2-diol, 3,6-dimethyl-4-cyclohexene-1,2-diol, 4,5-dimethyl-3-cyclooctene-1,2-diol; 4-cyclooctene-1,2-diol; and / or 5-cyclooctene-1,2-diol; VIII. Alkoxylated derivatives of diols, C ₃ _ _g including: First 1,2-propanediol (C3) 2 (Me-E ₁ _ _4), 1,2-propanediol (C3) P0 ₄ 2- methyl-l, 2-propanediol (C4) (Me-E ₄ _ _10), 2-methyl-1,2-propanediol (C4) 2 (Me-E _4), 2-methyl-l, 2-propanediol (C4) P0 _g , 2-methyl-1,2-propanediol (C4) BO-1, 1,3-propanediol (C3) 2 (Me-E _{g- g} ), 1,3-propanediol (C3) PO _{5 - g} , 2,2-diethyl-1,3-propanediol (C7) EN] γ, 2,2-diethyl-1,3-propanediol (C7) PO ₄ , 2,2- diethyl1.3- propanediol (C7) n-bO- _ _{L 2,} 2,2-dimethyl-1,3-propanediol (C5) 2 (Me-E ₁ _ _2), 2,2-dimethyl-l, 3-propanediol (5) _ ₃ PO _4, 2- (1-methylpropyl) -1,3-propanediol (C7) EN _1-7 , 2- (1-methylpropyl) -1,3-propanediol (C7) PO-1, 2- (1-methylpropyl) -1 3-propanediol, (C7) n-BO ₄ _ _2, 2- (2-methylpropyl) -1,3-propanediol (7) E _1-7 2- (2-methylpropyl) -1,3-propanediol (7) P0 _4, 2- (2-methylpropyl) -1,3-propanediol (7) η-ΒΟ ₄ _ _2, 2-ethyl-1,3- propanediol (C5) (Me E _{g- 10} ), 2-ethyl-1,3-propanediol (C5) 2 (Me EJ, 2-ethyl-1,3-propanediol (C5) P0 _g , 2-ethyl-2-methyl-1,3-propanediol (C6) (Me-E _{4 g} ), 2-ethyl-2-methyl-1, 3-propanediol (6) P0 ₂ 2-ethyl-2-methyl-l, 3-propanediol (6) B0 _4, 2-isopropyl-l, 3-propanediol (C6) (Me E ₄ _ _g), 2-isopropyl-l, 3-propanediol (6 ) P0 _2, 2-isopropyl-l, 3-propanediol (6) B0 _1; 2-methyl-l, 3-propanediol (C4) 2 (Me-E ₂ _ _5), 2-methyl-l, 3-propanediol (4) PO ₄ _ ₅ 2-methyl-l, 3-propanediol (4) B0 _2, 2-methyl-2-isopropyl-l, 3-propanediol (7) E ₂ _ _9, 2-methyl-2-isopropyl-l, 3-propanediol ( C7) PO-j, 2-methyl-2-isopropyl-l, 3-propanediol (C7) n-BO ₁ _ _3, 2-methyl • · 162 fl · fl fl fl fl fl fl fl -2-propyl-l, 3-propanediol (7) E ₁ _ _7, 2-methyl-2-propyl-l, 3-propanediol (7) p PO-2-methyl-2-propyl-l, 3-propanediol (C7) n-BO ₁ _ _2, 2-propyl-l, 3-propanediol (C6) (Me-E _{4 4} _) 2-propyl-1,3-propanediol (C6) _{PO 2} , 2-propyl-1,3-propanediol (C6) B0 · 2. 1,2-butanediol (C4) (Me E _{2 -Q} ); 1,2-butanediol (C4) PO ₂ _ ₃ , 1,2- butanediol (C4) BO beta-2,3-dimethyl-1,2-butanediol (6) E ₁ _ _g 2,3- dimethyl-1,2-butanediol (C6) n-BO ₁ _ _2, 2-ethyl-2-butene (6) El-3, 2-ethyl-2-butene (6) n-BO -p 2-methyl-1,2-butanediol (C5) (MeE- _{L- 5} ), 2-methyl-1,2-butanediol (C5) PO-p 3,3- dimethyl-1,2-butanediol (6) Ε ₄ _ _6, 3-dimethyl-1,2-butanediol (C6) n-BO ₁ _ _2, 3-methyl-1,2-butanediol (C5) (MEE - _L _ ₂ ), 3-methyl-1,2-butanediol (C5) PO-p 1,3-butanediol (C4) 2 (MeE _{3- g} ), 1,3-butanediol (C4) PO ₅ , 1,3-butanediol (C4) BO ₂ , 2,2,3-trimethyl-1,3-butanediol (C7) (MeEl-3), 2,2,3-trimethyl- 1,3-butanediol (C7) PO-p _2, 2,2-dimethyl-1,3-butanediol (C6) (MeE _{3- g} ), 2,2-dimethyl-l, 3-butanediol (6) P0 _3, 2,3-dimethyl-1,3-butanediol (C6) (MEE ₃ _G), 3-dimethyl-l, 3-butanediol (6) P0 ₃ , 2-ethyl-l, 3-butanediol, (C6) (MEE ₁ _ _g), 2-ethyl-l, 3-butanediol (6) PO ₂ _ _3, 2-ethyl-l, 3-butanediol (6) BO -p 2-ethyl-2-methyl-1,3-butanediol (C7) (MeE4), 2-ethyl-2-methyl-1,3-butanediol (C7) PO-p 2-ethyl-2-methyl- 1,3-butanediol (C7) n-B0 ₂ _ ₄ 2-ethyl-3-methyl-1,3-butanediol (C7) (MeE-1,2) -ethyl-3-methyl-1,3-butanediol (C7) PO-p 1,3-butanediol (C7) n- BO _{2 - 4} , 2-isopropyl-1,3-butanediol (C7) (MeE ₄ ), 2-isopropyl-1,3-butanediol (C7) PO-p 2-isopropyl-1,3-butanediol (C7) n -BO _{2, 4} , 2-methyl-1,3-butanediol (C5) 2 (MeE1-3), 2-methyl-1,3-butanediol (C5) PO ₄ , 2-propyl-1,3-butanediol ( C7) _ E _{2 g} of 2-propyl-1,3-butanediol (7) p PO-2-propyl-l, 3-butanediol (C7) _n-BO-3 beta, 3-methyl-1,3-butanediol (C5) 2 (MEE ₁ _ _3), 3-methyl-1,3-butanediol (5) P0 ₄ 1,4-Butanediol (04) 2 (MEE ₂ _ ₄₎ 1,4-butanediol (04) PO ₄ cp 1,4-butanediol (C4) BO ₂ , 2,2,3-trimethyl-1,4-butanediol (C7) E _{2 - 9} , 2,2,3- trimethyl-1,4-butanediol (07) PO-p 2.2.3- trimethyl-l, 4-butanediol (C7) n-P _B0-3, 2,2-dimethyl-1,4-butanediol (C6) (MEE-j__ _g), 2,2-dimethyl-l, 4-butanediol (6) P0 _2, 2,2-dimethyl-l, 4-butanediol (6) B0 beta-2,3-dimethyl-1,4-butanediol (6) (p-Mee _g), 2.3 -dimethyl-1,4-butanedio-0 - 163 • 0 · 0 < • 0 < 0 (0) 0 (1) (C6) PO ₂ , 2,3-dimethyl-1,4-butanediol (C6) B0 _1-2 -ethyl-1,4-butanediol (C6) (MeE _{4 - 4} ), 2-ethyl- 1,4-butanediol (C6) PO ₂ , 2-ethyl-1,4-butanediol (C6) BOp 2-ethyl-2-methyl-1,4-butanediol (C7) EN _1-7 , 2-ethyl-2 methyl-1,4-butanediol (7) pOP 2-ethyl-2-methyl-l, 4-butanediol (C7) n-BO ₁ _ _2; 2-ethyl-3-methyl -1, 4-butanediol ( C7) E 2-ethyl-3-methyl-1,4-butanediol _1-2 -ethyl-3-methyl-1,4-butanediol (C7) n-BO- _{L- 2} , 1-7 'lu (C7) PO 2 -isopropyl-1,4-butanediol (C7 lu (C7) PO ₁ -yl-1,4-butanediol (C5) (MeE ^E 1-7' 2-isopropyl-1,4) -butandio2-isopropyl-1,4-butanediol (C7) n-BO ₁ _ _2, 2-methyl) -2-methyl-4-butandio6-10 isoxazole (C5) 2 (MEE _1), 2-methyl-1 4-butanediol (C5) PO ₃ , 2-methyl-1,4-butanediol (C5) BO ₁ 2-propyl-1,4-butanediol (C7) Ep ₅ , 2-propyl-1,4-butanediol (C7) ) _n-1 B0 _ _2, 3-ethyl-l-methyl-1,4-butanediol (7) E 2-9 3-ethyl-1-methyl-1,4-butanediol (C7) POp 3-ethyl-2,3-butanedioE1), 2,3-butanedio-1-methyl-1,4-butanediol (C7) n-B0p ₃ LU (4) (MeEg_ _10), 2,3-butanediol (C4) isoxazole (4) ₃ PO ₄ _, 2,3-butanediol (C4), BOP · 2,3-dimethyl-2,3-butanediol (C6 ) _G E _3, 2,3-dimethyl-2,3-butanediol (6) PO _4, 2-methyl-2,3-butanediol (C5) (Me ^E 1_ _5), 2-methyl-2,3-butandio2 (Me lu (C5) PO. Of 2-methyl-2,3-butanediol (C5) BOp 3. 1,2-pentanediol (C5) E1,2-pentanediol (C5) n-BO ₂ _ ₃ ol (6) E ^ BO 3-methyl-1,2-pentanediol (C6) n-BOp 1,2-pentanediol (C5) POp 2-methyl-1,2-pentanedioic ₃ 2-methylpropyl, 2-methyl-l, 2-pentanediol (C6) n BOP -1,2-pentanediol (6) BOP 3-methyl-1,2-pentanediol (6 Ep ₃ , ol (C6) E 1-3 · 4-methyl-1,2-pentanediol 4-methyl-1,2-pentanedioic (C6) n BOP-1,3-pentanediol (C5) 2 (Me-EP _2), 1,3-pentanediol (C5) PO ₃ _ _4, 2,2-dimethyl- 1,3-pentanediol (C7) _(Me-E4), 2,2-dimethyl-1,3-pentandi2,2-dimethyl-l, 3-pentanediol (C7) n-BO ol (7) pOP 2,3-dimethyl-1,3-pentanediol (C7) (Me-E ₄ ), 2,3-dimethyl-1,3-pentanediol (C7) POp 2,3-dimethyl-1,3-pentanediol (C7) n- BO ₂ _ ₄ 2,4-dimethyl-1,3-pentanediol (C7) (Me-E4) 2,4-dimethyl-1,3-pen-4-tandiol (C7) PO-, 2,4-dimethyl-1,3-pentanediol (C7 E D 2-ethyl-1,3-pentanediol (C7) n-B0p _3, 2-methyl-l, 3-pentanedioic n-BO 2-4 ' 2-ethyl-1,3-pentanediol (C7) ^E 2-9 '1,3-pentanediol (C7) POp 2-methyl-l, 3-pentanediol (6) PO ol (C6) 2 (Me-E ₁ _ _g); 2-methyl-1,3-pentanediol (C6) BOp 3,4-dimethyl-1,3-pentanedio2-3 164 · 4 · 4 · 4 · 4 · 4 · 1 · 4 (Me7) (Me-Ep; 3,4-dimethyl-1,3- pentanediol (C7) PO-p 3,4-dimethyl-1,3-pentanediol (07) n-BO _{2, 4} , 3-methyl-1,3-pentanediol (06) (Me-Epg) 3-methyl-1,3-pentanediol (06) PO ₂ _ ₃ 3-methyl-1,3-pentanediol (06) of BOP 4,4-dimethyl-l, 3-pentanediol (C7) (Me-E _1), 4,4-dimethyl-1,3-pentanediol (7) pop 4,4-dimethyl-l, 3 -pentandiolu (C7) n-B0 ₂ _ _4, 4-methyl-1,3-pentanediol (06) (Me-EPG), 4-methyl-1,3-pentanediol ( 06) PO ₂ _ _3, 4-methyl-1,3-pentanediol (6) BOP 1,4-pentanediol (05) 2 (Me-E ₁ _ ₂₎ 1,4-pentanediol (C5) PO _{3, 4} , 2,2-dimethyl-1,4-pentanediol (07) (Me-E-J, 2,2-dimethyl-1,4-pentanediol (07) POp 2,2 -dimethyl-1,4-pentanediol (07) n-BO _{2, 4} , 2,3-dimethyl-1,4-pentanediol (07) (β-E, 2,3-dimethyl-1,4-pentanediol) (07) ) pOP 2,3-dimethyl-1,4-pentanediol (07) n-BO ₂ _ _4, 2,4-dimethyl-1,4-pentanediol (07) (Me-E ij; 2,4-dimethyl- 1,4-pentanediol (07) POp 2,4-dimethyl-1,4-pentanediol (07) n-BO _{2, 4} , 2-methyl-1,4-pentanediol (06) (Me-Epg), 2-methyl-1,4-pentanediol (06) PO ₂ _ ₃ , 2-methyl-1,4-pentanediol (06) BOp of 3,3-dimethyl-1,4-pentanediol (07) (Me-E-), 3,3-dimethyl-1,4-pentanediol (07) pop 3,3-dimethyl-1,4-pentanediol (C7) n-B0 ₂ _ _4, 3,4-dimethyl-l, 4-pentanediol (C7) (Me-E ij, 3,4-dimethyl-l , 4-pentanediol (7) pOP 3,4dimethyl-1,4-pentanediol (C7) n-BO ₂ _ _4, 3-methyl-1,4-pentanediol (06) 2 (Me-EPG), 3-methyl- 1,4-pentanediol (6) PO ₂ _ _3; 3-methyl-1,4-pentanediol (06) of BOP, 4-methyl-1,4-pentanediol (06) 2 (Me-EPG), 4-methyl-1 4-pentanediol (06) PO ₂ _ ₃ , 4-methyl-1,4-pentanediol (06) of BOP 1,5-diol (05) (Me-E ₄ _ _10), 1,5-pentanediol (05) 2 (Me-E _1), 1,5- pentanediol (05) PO ₃ , 2,2-dimethyl-1,5-pentanediol (07) Ep ₇ , 1,5-pentanediol, 2,2-dimethyl- (07) POp · 2,2-dimethyl-1,5-pentanediol (07) n-B0p ₂ '2,3-dimethyl-1,5-pentanediol (07) Ep ₇ , 2,3- dimethyl-l, 5-pentanediol (07) POP 2,3-dimethyl-1,5-pentanediol (C7) n-B0p _2, 2,4-dimethyl-1,5-pentanediol (07) Ep _7; 2,4- dimethyl-1,5-pentanediol (07) POP 2,4-dimethyl-l, 5-pentanediol (C7) n-B0p _2, 2-ethyl-1,5-pentanediol (7) Ep _5, 2-ethyl -1,5-pentanediol (07) n B0p _2, 2-methyl-1,5-pentanediol (06) (Me-EP _4), 2-methyl-1,5-pentanediol (06) P0 _2, 3, 3-dimethyl-l, 5-pentanediol (07) Ep _7, 3,3-dimethyl-1,5-pentanediol (07) pOP 3,3-dimethyl-l, 5-pentanediol (07) n B0p ₂ 165 3- methyl-l, 5-pentanediol (C6) (Me-E ₁ _ _4), 3-methyl-l, 5-pentanediol (6) P0 _2, 2,3-pentanediol (C5) (Me-El-3 ), 2,3-pentanediol (C5) ₂ P0, 2-methyl-2,3-pentanediol (6) _E-L _ _7, 2-methyl-2,3-pentanediol (6) _Ρ0 χ 2-methyl- 2,3-pentanediol (C6) n-BO ₁ _ _2, 3-methyl-2,3-pentanediol (6) _ ₇ E _L, 3-methyl-2,3-pentanediol (6) P0 _1-methyl-3 -2,3-pentanediol (C6) n-BO- _{L- 2} , 4-methyl-2,3-pentanediol (6) _E-L _ _7, 4-methyl-2,3-pentanediol (6) p PO-4-methyl-2,3-pentanediol (C6) _n-L bO- _ _2, 2,4-pentanediol (C5) 2 (Me-E ₁ _ _4), 2,4-pentanediol (C5) P0 _4, 2,3-dimethyl-2,4-pentanediol (C7) (Me-E ₁ _ _4, 2,3-dimethyl-2,4-pentanediol (7) P0 _2, 2,4-dimethyl-2,4-pentanediol (C7) (Me-E ₁ _ ₄₎ 2,4-dimethyl-2,4-pentanediol (7) P0 _2, 2-methyl-2,4-pentanediol (C7) (Me-E ₅ _ _10), 2-methyl-2,4-pentanediol (7) P0 _3, 3,3-dimethyl-2,4-pentanediol (C7) (Me-E ₁ _ _4), 3,3-dimethyl-2,4-pentanediol (7) P0 _2, 3-methyl-2 4-pentanediol (C6) (Me-E ₅ _ ₁₀₎ 3-methyl-2,4-pentanediol (C6) PO3; 4th 1,3-hexanediol (C6) (Me-Ej.g), 1,3-hexanediol (C6) P0 ₂ 1,3-hexanediol (C6) B0 _LR 2-methyl-1,3-hexanediol (7) E ₂ _ _g 2- methyl-1,3-hexanediol (7) P0 _LZ 2-methyl-1,3-hexanediol (C7) n-BO j__ _3, 2-methyl-1,3-hexanediol (7) _FS B0 3-methyl 1,3-hexanediol (C7) _ E _{2 g} of 3-methyl-l, 3-diol (7) p PO 3- methyl-l, 3-hexanediol (C7) n BOP _3, 4-methyl-l, 3-diol (7) _ E _{2 g} of 4-methyl-l, 3-diol (7) p PO 4 methyl-l, 3-hexanediol (C7) n-B0 - [__ 3, 5-methyl-l, 3-diol (7) E ₂ _ _g 5- methyl-l, 3-diol (7) POP 5-methyl-l, 3-hexanediol (C7) n-BO ₁ _ _3, 1,4-hexanediol (C6) (Me-E-j__ _5), 1 , 4-hexanediol (C6) P0 _2, 1,4-hexanediol (6) BO-2-methyl-1,4-hexanediol (C7) _ E _{2 g} of 2-methyl-1,4-diol (7) _P 1 from 2-methyl-1,4-hexanediol (C7) n-B0- _L , 3,3-methyl-1,4-hexanediol (C7) E _{2 g} , 3-methyl-1,4-hexanediol (C7) PO ρ-3-methyl-l, 4-diol (C7) n-BO ₁ _ _3, 4-methyl-l, 4-diol (7) _ E _{2 g} of 4-methyl-1,4-hexanediol (C7 ) PO-j, 4-methyl-l, 4-diol, (C7) n-BO ₁ _ ₃ 5-methyl-l, 4-diol (7) E ₂ _ _g 5-methyl-l, 4-diol (7) PO p 5-methyl-l, 4-diol (C7) n-BO ₁ _ ₃ 1,5-hexanediol (C6) (Me-E _{4 - 5} ), 1,5-hexanediol (C6) PO ₂ 1,5-hexanediol (C6) BO-p 2-methyl-1,5-hexanediol (C7) ) _ E _{2 g} of 2-methyl-l, 5-diol (7) p PO-2-methyl-l, 5-hexanediol (C7) n-BOpj, φ · I * «> 4 4 4« 166 3-Methyl-1,5-diol (7) E ₂ _ _g ·· »« ·· 3-methyl-1,5-hexanediol _(C7) PO _FS 3-methyl-1,5-hexanediol (C7) n-BO-1,5-diol (7) E ₂ _ ₉ 4-methyl-1,5-hexanediol (C7) n-BO 4-methyl-4-methyl-1,5-hexanediol (C7) PO _{1 # 3} of 5-methyl-1,5-hexanediol (C7) E 5-Methyl-1,5-diol (7) -methyl-PA5> -j__ _3, 1,6-hexanediol (C6) (Me-E ₁ _ _2), 1,6-hexanediol (C6) ₂ PO- _L _ 1,6-hexanediol (C6) n-BO _4, 2-methyl-1,6-hexanediol (C7) E-j__ _5, 2-methyl-l, 6-hexanediol (C7) n-BO 2-9 1,5-hexanediol (C7) n-BO3-methyl-1,6-hexanediol (C7) E ol (C7) n-BO ₁ _ ₂ ol (C6) n-bO- | _. 1-5 ' 2,3-hexanediol (C6) E _1-5 , 2,3-hexanediol (C6) BO-,, 1-2 ' 3-methyl-1,6-hexandi2.3- hexandi2.4- hexanediol (C6) (Me-E _ _{3 g),} 2,4-hexanediol (C6) _PO3; 2-methyl-2,4-hexanediol (C7) (Me-E ₁ _ _2), 2-methyl-2,4-hexanediol (C7) PO _{j__-2,} 3-methyl-2,4-diol (7) (Me-E ₁ _ _2), 3-methyl-2,4-hexanediol (7) ΡΟχ _] _ ζ 4-methyl-2,4-hexanediol (C7) (Me-E ₁ _ _2), 4-methyl-2 4-diol (7) ΡΟ- | __ ₂ 5-methyl-2,4-hexanediol (C7) (Me-E ₁ _ _2), 5-methyl-2,4-hexanediol (C7) _ _{1 2} P0 2,5-hel _q _3), 2,5-hexanediol (C6i xandiolu (C6) (Me-E -2,5-hexanediol (C7) (Me-E ₁ _ _2), 2-methyl-2,5 hexanediol (C7) P0 ₁ _ _2, 3-methyl-2,5-hexanediol (C7) (Me-E ₁ _ _2), 3-methyl-2,5-hexanediol (7) PO- | __ _2, 3 Of 4-hexanediol (C6) EO 3,4-hexanediol (C6) n-BO4, 3,4-hexanediol (C6) BO4; 5. 1,3-heptanediol (C7) Ε _1-7 , 1,3-heptanediol (C7) P0 _lz PO ₃ , 2-methyl-1-5 1,3-heptanediol (C7) n-BO-j 1,4-heptanediol (C7) 1 _ν 1 Of 1,5-heptanediol (C7) ^E 1-7 ' Of 1,5-heptanediol (C7) η-Β0 - ^ _ Of 1,6-heptanediol (C7) po _1z 1 1,7-heptanediol (C7) ^E 1 - 2 ' 2,4-heptanediol (C7) ^E 3-10 ' 2,4-heptanediol (C7) P0 _lø 2 2,5-heptanediol (C7) ^E 3-10 ' 2,5-heptanediol (C7) PO _lz 2 2,6-heptanediol (C7) ^E 3-10 ' 2,6-heptanediol (C7) P0 _lz 2 3,5-heptanediol (C7) ^E 3-10 ' 3,5-heptanediol (C7) PO-1 3, Ύ-2 1,6-heptanediol (C7) E ₄ _ _7, 1,6-heptanediol (C7) n-BO _{j__-2,} 7-heptanediol (C7) n-fight, 5-heptanediol (C7) (Me-E- ^); 2,5-heptanediol (C7) n-BO _3; 2,6-heptanediol (C7) (Me-Ej), 3-10 ' ³ ' of 5-heptanediol (C7) (Me-E-1, leptanediol (C7) n-BO ₃ ; • 9 · 9 · 9 · 9 · 9 · 167 9999 8 · ·· 6. 3-methyl-2-isopropyl-1,3-butanediol (C8) PO-p 2,3,3-trimethyl-2,4-pentanediol (C8) PO-, 2,2-diethyl-1,3 -butanediol (C8) E _{2, 5} , 2,3-dimethyl-2,4-hexanediol (C8) E _{2, 5} , 2,4-dimethyl-2,4-hexanediol (C8) E _{2, 5} , 2, 5-dimethyl-2,4-hexanediol (C8) E _{2, 5} , 3,3-dimethyl-2,4-hexanediol (C8) E _{2, 5} , 3,4-dimethyl-2,4-hexanediol (C8) E _{2 - 5} , 3,5-dimethyl-2,4-hexanediol (C8) E _{2 - 5} , 4,5-dimethyl-2,4-hexanediol (C8) E _{2 - 5} , 5,5-dimethyl-2 , 4-hexanediol (C8) E ₂ _ _5, 2,3-dimethyl-2,5-hexanediol (C8) E ₂ _ _5, 2,4-dimethyl-2,5-hexanediol (C8) E ₂ _ ₅ 2,5-dimethyl-2,5-hexanediol (C8) E _{2, 5} , 3,3-dimethyl-2,5-hexanediol (C8) E _{2, 5} , 3,4-dimethyl-2,5-hexanediol ( C8) _ E _{2 5,} 3-methyl-3,5-heptanediol (C8) E ₂ _ _5, 2,2-diethyl-l, 3-butanediol (C8) n-BO ₁ _ _2, 2,3-dimethyl -2,4-hexanediol (C8) n-BO ₁ _ ₂ 2,4- dimethyl-2,4-hexanediol (C8) n-BO ₁ _ _2, 2,5-dimethyl-2,4-hexanediol (C8) n-BO ₁ _ _2, 3,3-dimethyl-2,4- hexanediol (C8) n-BO- _{L- 2} , 3,4- dimethyl-2,4-hexanediol (C8) n-bO- _ _{L 2,} 3,5-dimethyl-2,4-hexanediol (C8) n-BO ₁ _ _2, 4,5-dimethyl-2 4-hexanediol (C8) n-BO- _{L- 2} , 5,5- dimethyl-2,4-hexanediol, n-bO- _ _{L 2,} 2,3-dimethyl-2,5-hexanediol (C8) n-BO ₁ _ _2, 2,5-dimethyl-2,5-hexanediol ( C8) n-BO ₁ _ ₂ 2.5- dimethyl-2,5-hexanediol (C8) n-BO ₁ _ _2, 3,3-dimethyl-2,5-hexanediol (C8) n-BO ₁ _ _2, 3,4-dimethyl-2,5- hexanediol (C8) n-BO- _{L- 2} , 3-methyl-3,5-heptanediol (C8) n-BO ₁ _ _2, 2- (1,2-dimethylpropyl) -1,3-propanediol (C8) n-BO _LR 2-ethyl-2,3-dimethyl- -1,3-butanediol, (C8) n-BO-β-2-methyl-2-isopropyl-1,3-butanediol (C8) n-BO-β-3-methyl-2-isopropyl-1,4-butanediol ( C8) n-BO _1, 2,2,3-trimethyl-1,3-pentanediol (C8) n-BO _1, 2,2,4-trimethyl-1,3-pentanediol (C8) n-BO-2 p 4,4-trimethyl-1,3-pentanediol (C8) n-BO4, 3,4,4-trimethyl-1,3-pentanediol (C8) η-ΒΟ-ρ · 2,2,3-trimethyl-1,4-pentanediol, (C8) η-ΒΟ-ρ 2,2,4-trimethyl- 1,4-pentanediol (C8) n-BO-p 2,3,3-trimethyl-1,4-pentanediol (C8) η-ΒΟ-ρ 2,3,4-trimethyl-1,4-pentanediol (C8) n-BO-p 3,3,4-trimethyl-1,4-pentanediol, (C8) n-BO-p 2,3,4-trimethyl-2 4-pentanediol (C8) n-BO-p 4-ethyl-2,4-hexanediol (C8) n-BO-p 2-methyl-2,4-heptanediol (C8) n-BO-p 3-methyl- 2,4-heptanediol (C8) n-BO, 4-methyl-2,4-heptanediol (C8) n-BO-p 5-methyl-2,4-heptanediol (C8) n-BO-p 6-methyl- 2,4-heptanediol (C8) n-BO-β 2-methyl-2,5-heptanediol (C8) η-ΒΟ-ρ 3-methyl-2,5-heptanediol · · 168 «• · ·· ·· · · · * · · · ·· • • 9999 • · · · · · ·« ·· · 99 9 ol (C8) n-BO _LZ 4-methyl-2,5- heptanediol (C8) n-BO _1, 5-methyl-2,5-heptanediol (C8) n-BC, 6-methyl-2,5-heptanediol (C8) n-BO-, 2-methyl-2, 6-heptanediol (C8) n- _BO1-3 -methyl-2,6-heptanediol (C8) n-BO- _p4 -methyl-2,6-heptanediol (C8) n- _{BO1 #} 2-methyl-3, 5-heptanediol (C8) n-BO-p 2- (1,2-dimethylpropyl) -1,3-propanediol (C8) Ε-β, 2-ethyl-2,3-dimethyl-1,3-butanediol (C8) ) E- _L _ ₃ , 2-methyl-2-isopropyl-1,3-butanediol (C8) E ₁ _ _3, 3-methyl-2-isopropyl-1,4-butanediol (8) E ^ _ _3, 2,2,3-trimethyl- 1,3-pentanediol (C8) Ep ₃ , 2,2,4-trimethyl-1,3-pentanediol (C8) Ε _1-3 , 2,4,4-trimethyl-1,3-pentanediol (C8) E ₁ _ _3, 3,4,4-trimethyl-1,3-pentanediol (C8) E ₁ _ _3, 2,2,3-trimethyl- 1,4-pentanediol (C8) E ₁ _ _3, 2,2,4-trimethyl-1,4-pentanediol (C8) E ₁ _ ₃ 2,3,3-trimethyl-1,4-pentanediol (8) Ερ _3, 2,3,4-trimethyl-1,4-pentanediol (C8) E ₁ _ _3, 3,3,4-trimethyl-1, 4-pentanediol (C8) Ep ₃ , 2,3,4-trimethyl-2,4-pentanediol (C8) E- _{L- 3} , 4-ethyl-2,4-hexanediol (8) Ερ _3, 2-methyl-2,4-heptanediol (8) Ep _3, 3-methyl-2,4-heptanediol (C8) E _L _ _3, 4- methyl-2,4-heptanediol (8) E-j__ _3, 5-methyl-2,4-heptanediol (C8) E ₁ _ ₃ 6-methyl-2,4-heptanediol (8) Ep _3, 2-methyl-2,5-heptanediol (8) Ep _3, 3-methyl-2,5-heptanediol (C8) E _1-3, 4-methyl 2,5-heptanediol (8) Ep _3, 5-methyl-2,5-heptanediol (8) Ep ₃ 6-methyl-2,5-heptanediol (C8) E ₁ _ _3, 2-methyl-2,6-heptanediol (C8) E ₁ _ _3, 3-methyl-2,6-heptanediol (C8) E ₁ _ ₃ 4-methyl-2,6-heptanediol (C8) Ep ₃ and / or 2-methyl-3,5-heptanediol (C8) Ep ₃ ; and 7. mixtures; IX aromatic diols including 1-phenyl-1,2-ethanediol, 1-phenyl-1,2-propanediol, 2-phenyl-1,2-propanediol, 3-phenyl-1,2-propanediol, 1- (3-methylphenyl) -1,3-propanediol, 1- (4-methylphenyl) -1,3-propanediol, 2-methyl-1-phenyl-1,3-propanediol, 1-phenyl-1,3-butanediol, 3-phenyl-1,3 -butanediol, 1-phenyl-1,4-butanediol, 2-phenyl-1,4-butanediol and / or 1-phenyl-2,3-butanediol; X. solvents having a ClogP of 0.15 to 0.64 and which are homologues or analogs of the above compounds derived from these compounds by the addition of one or more CH ₂ groups while simultaneously removing two hydrogen atoms from two adjacent carbon atoms for each an added CH ₂ group to form one double 0 · • 0 I 0 · 0 • 0 «0 < 0 0 « 00 00 0 ·> «00 169 carbon-carbon bonds, i.e., but not limited to: 2,2-di-2-propenyl-1,3-propanediol, 2- (1-pentenyl) -1,3-propanediol, 2- (2-methyl-2-propenyl) -2- (2-propenyl) -1,3-propanediol, 2- (3-methyl-1-butenyl) -1,3-propanediol, 2- (4-pentenyl) -1,3-propanediol, 2-ethyl-2- (2-methyl-2-propenyl) -1,3-propanediol, 2-ethyl-2- (2-propenyl) -1,3-propanediol, 2- methyl 2- (3-methyl-3-butenyl) -1,3-propanediol, 2,2-diallyl-1,3-butanediol, 2- (1-ethyl-1-propenyl) -1,3-butanediol, 2- (2-Butenyl) -2-methyl-1,3-butanediol 2- (3-methyl-2-butenyl) -1,3-butanediol, 2-ethyl-2- (2-propenyl) -1,3-butanediol, 2-methyl-2- (1-methyl-2-propenyl) ) -1,3-butanediol, 2,3-bis (1-methylethylidene) -1,4-butanediol, 2- (3-methyl-2-butenyl) -3-methylene-1,4-butanediol, 2- (1,1-dimethylpropyl) -2 -butene-1,4-diol, 2- (1-methylpropyl) -2-butene-1,4-diol, 2-butyl-2-butenyl-1,4-diol, 2-ethenyl-3-ethyl-1 , 3-pentanediol, 2-ethenyl-4,4-dimethyl-1,3-pentanediol, 3-methyl-2- (2-propenyl) -1,4-pentanediol, 2- (1-propenyl) -1,5 -pentanediol, 2- (2-propenyl) -1,5-pentanediol, 2-ethylidene-3-methyl-1,5-pentanediol, 2-propylidene-1,5-pentanediol, 3-ethylidene-2,4-dimethyl -2,4-pentanediol, 2- (1,1-dimethylethyl) -4-pentene-1,3-diol, 2-ethyl-2,3-dimethyl-4-pentene-1,3-diol, 4-ethyl -2-methylene-1,4-hexanediol, 2,3,5-trimethyl-1,5-hexadiene-3,4-diol, 5-ethyl-3-methyl-1,5-hexadiene-3,4-diol , 2- (1-methylethenyl) -1,5-hexanediol, 2-ethenyl-1,6-hexanediol, 5,5-dimethyl-1-hexene-3,4-diol, 5,5-dimethyl-1-hexene-3,4-diol, 4-ethenyl-2,5-dimethyl-2-hexene-1,5-diol, 2-ethenyl-2,5-dimethyl-3-hexene-1,6-diol, 2-ethyl-3-hexene-1,6- diol, 3,4-dimethyl-3-hexene-1,6-diol, 2,5-dimethyl-4-hexene-2,3-diol, 3,4-dimethyl-4-hexene-2,3-diol, 3- (2-propenyl) -5-hexene-1,3-diol, 2,3-dimethyl-5-hexene-2,3-diol, 3,4-dimethyl-5-hexene-2,3-diol, 3,5-dimethyl-5-hexene-2,3-diol, 3-ethenyl-2,5-dimethyl-5-hexene-2,4-diol, 6-methyl-5-methylene-1,4-heptanediol, 2,3-dimethyl-1,5-heptadiene-3,4-diol, 2,5-dimethyl-1,5-heptadiene-3,4-diol, 3,5-dimethyl-1,5-hepta-diene- 3,4-diol, 2,6-bis (methylene) 1,7-heptanediol, 4-methylene-1,7-heptanediol, 2,4-dimethyl-1-heptene-3,5-diol, 2,6-dimethyl-1-hepten-3,5-diol, 3-ethenyl-5-methyl-1-hepten-3,5-diol, 6,6-dimethyl-1-hepten-3,5-diol, 4, 6-dimethyl-2,4-heptadiene-2,6-diol, 4,4-dimethyl-2,5-heptadiene-1,7-diol, 2,5,5-trimethyl-2,6-heptadiene-1, 4-diol, 5,6-dimethyl-2-heptene-1,4-diol; 170 toto * * * * * * * * * * to < 5-ethyl-2-hepten-1,5-diol, 2-methyl-2-hepten-1,7-diol, 4,6-dimethyl-3-hepten-1,5-diol, 3-methyl-6- methylene-3-heptene-1,7-diol, 2,4-dimethyl-3-hepten-2,5-diol, 2,5-dimethyl-3-hepten-2,5-diol, 2,6-dimethyl-3-heptene-2,6-diol, 4,6-dimethyl-3-heptene-2,6-diol, 2,4-dimethyl-5-heptene-1,3-diol, 3,6-dimethyl-5-heptene-1,3-diol, 2,6-dimethyl-5-heptene-1,4-diol, 3,6-dimethyl-5-heptene-1,4-diol, 2,3-dimethyl-5-heptene-2,4-diol, 2,2-dimethyl-6-heptene-1,3-diol, 4- (2-propenyl) -6-heptene-1,4-diol, 5,6-dimethyl-6-heptene-1,4-diol, 2,4-dimethyl-6-heptene-1,5-diol, 2-ethylidene-6-methyl-6-heptene-1,5-diol, 4- (2-propenyl) -6-heptene-2,4-diol, 5,5-dimethyl-6-heptene-2,4- diol, 4,6-dimethyl-6-heptene-2,5-diol, 5-ethenyl-4-methyl-6-heptene-2,5-diol, 2-methylene-1,3-octanediol, 2,6- dimethyl-1,6-octadiene-3,5-diol, 3,7-dimethyl-1,6-octadiene-3,5-diol, 2,6-dimethyl-1,7-octadiene-3,6-diol, 2,7-dimethyl-1,7-octadiene-3,6-diol, 3,6-dimethyl-1,7-octadiene-3,6-diol, 3-ethenyl-1-octene-3,6-diol, 2,7-dimethyl-2,4,6-octatriene-1, 8-diol, 3,7-dimethyl-2,4-octadiene-1,7-diol, 2,6-dimethyl-2,5-octadiene-1,7-diol, 3,7-dimethyl-2,5-octadiene-1,7- diol, 3,7-dimethyl-2,6-octadiene-1,4-diol (Rosiridol), 2-methyl-2,6-octadiene-1,8-diol, 3,7-dimethyl-2,7-octadiene -1,4-diol, 2,6-dimethyl-2,7-octadiene-1,5-diol, 2,6-dimethyl-2,7-octadiene-1,6-diol (8-Hydroxylinalool), 2, 7-dimethyl-2,7-octadiene-1,6-diol, 2-octene-1,4-diol, 2-octene-1,7-diol, 2-methyl-6-methylene-2-octene-1,7-diol, 3,7-dimethyl-3,5-octadiene- 1,7-diol, 2,7-dimethyl-3,7-octadiene-2,7-diol, 4-methylene-3,7-octadiene, 2,6-dimethyl-3,7-octadiene-1,6- diol, 2,7-dimethyl-3,7-octadiene-2,5-diol, 2,6-dimethyl-3,7-octadiene-2,6-diol, 4-methyl-3-octene-1,5-diol, 5-methyl-3-octene-1,5-diol, 2,2-dimethyl-4,6-octadiene-1,3-diol, 2,6-dimethyl-4,7-octadiene-2,3-diol, 2,6-dimethyl-4,7-octadiene-2,6-diol, 7-methyl-4-octene-1,6-diol, 2, 7-Bis (methylene) -2-methylene-2,7-dimethyl-5,7-octadiene-1,4-diol, 7-methyl-5,7-octadiene-1,4-diol, 6-octen-1 3-diol; 7-methyl-6-octene-1,3-diol, 7-methyl-6-octene-1,4-diol, 6-octene-1,5-diol, 7-methyl-6-octene-1,5- diol, 2-methyl-6-octene-3,5-diol, 4-methyl-6-octene-3,5-diol, 2-methyl-7-octene-1,3-diol, 4-methyl-7-octene-1,3-diol, 7-methyl-7-octene-1,3-diol, 7-octen-1,5-diene diol; 7-octene-1,6-diol, 5-methyl-7-octene-1,6-diol, 2-methyl-6-methylene-7-octene-2,4-diol, 7-meth · 171 7-octene-2,5-diol, 2-methyl-7-octene-3,5-diol, 1-nonene 3,5-diol; 1-nonene-3,7-diol; 3-nonene-2,5-diol, 8-methyl-4,6-nonadiene-1,3-diol, 4-nonene-2,8-diol, 6,8-nonadiene-1,5-diol, 7- nonene-2,4-diol; 8-Nonene-2,4-diol, 8-Nonene-2,5-diol, 1, 9-decadiene-3,8-diol and / or 1,9-decadiene-4,6-diol a XI. mixtures of said solvents, said major solvents comprising solvents selected from the group consisting of 2,2,4-trimethyl-1,3-pentanediol, ethoxy, diethoxy or triethoxy-2,2,4-trimethyl-1,3-pentanediol and / or 2-ethylhexyl-1,3-diol, in amounts which are insufficient to form a stable aqueous product. A fabric softening composition in the form of a stable aqueous dispersion comprising 4 to 50%, preferably 10 to 40% and more preferably 15 to 30% of the active ingredient according to any one of claims 1 to 4. A premix comprising the active ingredient of the fabric softening composition of any one of claims 1 to 4a, an effective amount of a perfume. A premix comprising components A, B and C of the formulations according to any one of claims 5 to 9. A solid fabric softening composition comprising an effective amount of the fabric softening active ingredient of any one of claims 1 to 4. 14. A clear fabric softening composition comprising an effective amount of the fabric softening active ingredient of claim 1. A process for preparing a fabric softening composition comprising adding a premix of claim 12 to water, adjusting the pH to 1.5 to 5 and adding an amount of a water-soluble calcium or magnesium salt sufficient to improve viscosity and / or - 172 • ·· φ · φ φ φ φ φ · ΦΦ ΦΦ · · φ · »φ φ φ φ φ Φφφ φ φφ φφ φ φ φ φ φ φ φ φ φφ the clarity of this preparation