CN1196082A - Concentrated, stable fabric softening composition containing chelant - Google Patents

Abstract

Clear or translucent fabric softening compositions having a biodegradable fabric softening active and an added chelating agent are disclosed. The biodegradable fabric softening active preferably has formula (1), wherein each R substituent is hydrogen or a short chain C1-C6, preferably C1-C3 alkyl or hydroxyalkyl group, e.g., methyl (most preferred), ethyl, propyl, hydroxyethyl, and the like, benzyl, or mixtures thereof; each m is 2 or 3; each n is from 1 to about 4, preferably 2; each Y is -O-(O)C-, -(R)N-(O)C-, -C(O)-N(R)-, or -C(O)-O-, preferably -O-(O)C-; the sum of carbons in each R<1>, plus one when Y is -O-(O)C- or -(R)N-(O)C-, is C6-C22, preferably C12-22, more preferably C14-C20, but no more than one R<1> or YR<1> sum being less than about 12 and then the other R<1> or YR<1> sum is at least about 16, with each R<1> being a long chain C5-C21 (or C6-C22), preferably C9-C19 (or C9-C20), most preferably C11-C17 (or C12-C18), straight, branched, unsaturated or polyunsaturated alkyl, the average Iodine Value of the parent fatty acid of the R<1> being from about 20 to about 140. The chelating agent is preferably diaminetriaminepentaacetic acid. The compositions display excellent clarity with a percentage haze in the transmission mode of a Hunter Color analysis of less than 90 %, preferably less than 50 %.

Description

Concentrated stable fabric softening compositions comprising chelants

Technical Field

The present invention relates to a translucent or clear aqueous concentrated liquid softening composition comprising a chelant. It particularly relates to softening compositions for use in the rinse cycle of a laundering operation to impart excellent fabric softening/static control functions. These compositions are characterized by, for example, reduced fabric staining, excellent water dispersibility, rewettability, and/or storage stability and viscosity stability at sub-ambient (i.e., below room temperature, e.g., 25 ℃) temperatures. Background

The prior art discloses problems associated with formulating and manufacturing concentrated fabric finishing formulations that are translucent or clear. For example, Machin et al, European patent application No.404471, 1990, 12, 27, refers to isotropic liquid softening compositions containing at least 20% by weight of a softening agent and at least 5% by weight of a short chain organic acid.

Fabric softening compositions containing high amounts of solvent are well known in the art. However, aggregates of the softening agent are formed and deposited on the laundry, which may cause contamination and decrease softening performance. In addition, at low temperatures, i.e., about 40 ° F (about 4 ℃) to about 65 ° F (about 18 ℃), the composition may thicken and/or precipitate. Because of the high solvent content (required to make a concentrated, clear product), these compositions can also be expensive to the consumer.

The present invention provides concentrated aqueous liquid fabric softening compositions having a low organic solvent content (i.e., less than about 40% by weight of the composition) and containing a chelating agent, which exhibit improved stability (i.e., remain clear or translucent, and do not precipitate, gel, thicken or set) at ambient, i.e., room temperature and sub-room temperature and for extended storage conditions. The composition also reduces fabric staining, has good cold water dispersibility, while also having excellent softening properties, antistatic properties and fabric rewetting properties, as well as reducing formulation residue buildup and imparting excellent freeze-thaw recovery. Background

U.S. patent No.3756950 discloses the addition of a chelating agent to a fabric softening composition to prevent yellowing of fabrics treated with the composition. U.S. patent No.5399272 discloses clear liquid softening compositions. U.S. patent No.5525245 also discloses clear liquid fabric softening compositions. Summary of The Invention

According to a first embodiment of the present invention, there is provided a clear or translucent fabric softening composition. The composition comprises:

A. from about 2% to about 80% by weight of the composition, a biodegradable fabric softener active selected from the group consisting of:

i. a compound having the general formula:wherein each R substituent is hydrogen or short chain C₁-C₆Preferably C₁-C₃An alkyl or hydroxyalkyl group; such as methyl (most preferred), ethyl, propyl, hydroxyethyl, and the like, benzyl, or mixtures thereof; each m is 2 or 3; each n is 1 to 4, preferably 2; each Y is-O- (O) C-, - (R) N- (O) C-, -C (O) -N (R) -, or-C (O) -O-, preferably-O- (O) C-; when Y is O- (O) C-or- (R) N- (O) C-, each R¹The total number of carbon atoms in (B) plus 1 is C₆-C₂₂Preferably C₁₂-C₂₂More preferably C₁₄-C₂₀But the number may be up to the point that one R¹Or YR¹Is less than 12, and the other R¹Or YR¹A total of at least about 16; while each R¹Is a long chain C₅-C₂₁(or C)₆-C₂₂) Preferably C₉-C₁₆(or C)₉-C₂₀) Most preferably C₁₁-C₁₇(or C)₁₂-C₁₈) Linear, branched, unsaturated or polyunsaturated alkyl, R¹The parent fatty acid of (a) has an average iodine value of from about 20 to about 140;

a compound having the formula:wherein each Y, R¹And X^(-)Have the same meaning as described above; and

mixtures thereof;

B. less than about 40% by weight of the composition of principal solvent having a Clog P of about 0.15 to 0.64;

C. from about 0.001% to about 10%, by weight of the composition, of a chelate;

D. an effective amount of a low molecular weight water-soluble solvent sufficient to improve clarity may also be included, selected from the group consisting of: ethanol, isopropanol, propylene glycol, 1, 3-propanediol, propylene carbonate, and mixtures thereof, the water-soluble solvent being present in an amount such that it does not form a clear composition on its own; and

E. balance water.

In the fabric softening active, each R¹May comprise a long chain C₅-C₂₁Branched or unsaturated alkyl groups, which may also be substituted, and which may also optionally have a ratio of branched alkyl groups to unsaturated alkyl groups of from about 5: 95 to about 95: 5, and for unsaturated alkyl groups, R¹The parent fatty acid of the group has an average iodine value of about 20 to 140. Optionally, the composition may further comprise about 15% to about 70% of a softener active, wherein each R substituent in the softener active is hydrogen or short chain C₁-C₃An alkyl or hydroxyalkyl group; each n is 2; each Y is-O- (O) C-; each R¹The total number of carbon atoms plus 1 of (C) is C₁₂-C₂₂And R is¹Is a branched alkyl group or an unsaturated alkyl group, the ratio of branched alkyl group to unsaturated alkyl group being from about 75: 25 to about 25: 75, and for unsaturated alkyl groups, the R is¹The parent fatty acid of the group has an average iodine value of about 50 to 130; and wherein the counter ion X-is selected from the group consisting of chloride, bromide, methosulfate, ethosulfate, sulfate, and nitrate.

It is also optional for each R substituent to be hydrogen or short chain C₁-C₃An alkyl or hydroxyalkyl group; each n is 2; at each R¹Wherein the sum of the number of carbons plus 1 is C₁₂-C₂₀(ii) a And counter ion X^-Selected from the group consisting of chloride, bromide, methosulfate, ethosulfate, sulfate and nitrate, more preferably each R substituent is selected from the group consisting of methyl, ethyl, propyl, hydroxyethyl and benzyl; each m is 2; each n is 2; each R¹The sum of the number of carbons of (a) plus 1 is C₁₄-C₂₀Each R¹Is a long chain C₁₃-C₁₉Branched alkyl or unsaturated alkylA ratio of branched alkyl groups to unsaturated alkyl groups of about 50: 50 to about 30: 70; for unsaturated alkyl, the R¹The iodine value of the parent fatty acid of the group is about 70-115; and wherein the counter ion is chloride.

In addition, the fabric softening active containing a polyunsaturated olefin group can also be present in an amount of at least about 3% by weight of the total weight of the softener active present, and R is¹The parent fatty acid of the group has an average iodine value of about 60 to 140.

The chelating agent in the composition is selected from the group consisting of diethylenetriaminepentaacetic acid, ethylenediaminetetraacetic acid, ethylenediaminen, N '-disuccinic acid, diethylenetriaminen, N', N "-penta (methylphosphonic acid), nitrilotriacetic acid, and mixtures thereof, with diethylenetriaminepentaacetic acid being most preferred. Preferably, the composition comprises the chelant in an amount of from about 0.01% to about 5% by weight of the composition and/or the fabric softener active in an amount of from about 4% to about 50% by weight of the composition.

According to a second embodiment of the present invention there is provided a clear or translucent fabric softening composition comprising:

A. from about 2% to about 80% by weight of the composition of a biodegradable fabric softener active;

B. less than about 40% by weight of the composition of principal solvents having a Clog P of about 0.15 to 0.64;

C. a chelate in an amount of about 0.001 to about 10% by weight of the composition to improve the color and clarity of the composition; and

E. a balance of water; wherein the composition has a percent haze in the Hunter color analysis transmission mode of less than about 90%.

Preferably, the percent haze in the Hunter color transmission mode analysis is less than about 50%, most preferably less than about 25%. The chelating agent is preferably selected from the group consisting of diethylenetriaminepentaacetic acid, ethylenediaminetetraacetic acid, ethylenediamine-N, N '-disuccinic acid, diethylenetriamine-N, N', N "-penta (methylphosphonic acid), nitrilotriacetic acid, and mixtures thereof, with diethylenetriaminepentaacetic acid being most preferred. The fabric softening active may be as defined above.

Preferably, the composition is aqueous, translucent or clear (most preferably clear) and contains about 3 to 95%, preferably about 5 to 80%, more preferably about 15 to 70%, even more preferably about 40 to 60% water, and about 3 to 40%, preferably about 10 to 35%, more preferably about 12 to 25%, even more preferably about 14 to 20% of the above-described primary alcohol solvent B. In the absence of primary solvent B, these preferred products (compositions) are not translucent or clear, and the amount of primary solvent B required to make the composition translucent or clear is preferably greater than about 50%, more preferably greater than about 60%, and even more preferably greater than about 75% of all organic solvents present.

The amount of primary solvent should be kept at a minimum level that provides acceptable stability/clarity to the compositions of the present invention. The presence of water plays an important role in the main solvent necessary to enable the clarity of these compositions. The higher the water content, the more the main solvent (relative to the content of softener) is needed to obtain the clarity of the product. Conversely, the lower the water content, the less of the main solvent (relative to the softener) is needed. Thus, at water levels as low as about 5-15%, the weight ratio of softener active to primary solvent is preferably 55: 45 to 85: 15, more preferably 60: 40 to 80: 20. The weight ratio of softener active to primary solvent is preferably 45: 55 to 70: 30, more preferably 55: 45 to 70: 30 at a water content of about 15-70%. However, when the water content is up to about 70% to 80%, the weight ratio of softener active to primary solvent is preferably from 30: 70 to about 55: 45, more preferably from 35: 65 to about 45: 55. At higher water contents, the ratio of softener to main solvent should be higher.

The pH of the composition is preferably from about 1 to about 7, preferably from about 1.5 to about 5, more preferably from about 2 to about 3.5. Detailed Description

I. Fabric softening actives

The present invention comprises as an essential component a fabric softener activator in an amount of from about 2% to about 80%, preferably from about 13% to about 75%, more preferably from about 17% to about 70%, even more preferably from about 19% to about 65% by weight of the composition, the fabric softener activator being selected from the group consisting of the compounds defined below and mixtures thereof:

(A) diester quatemary ammonium fabric softening active (DEQA)

(1) Class 1 of DEQA preferably comprises as the primary active a compound of the formula: $[{\left(R\right)}_{4-m}-N^{(+)}-[{\left({\mathrm{CH}}_2\right)}_n-Y-R^1{]}_m]X^{(-)}.....\left(1\right)$ wherein each R substituent is hydrogen or short chain C₁-C₆(preferably C)₁-C₃) Alkyl or hydroxyalkyl groups such as methyl (most preferred), ethyl, propyl, hydroxyethyl, and the like, and benzyl, or mixtures thereof; each m is 2 or 3; each n is 1 to 4, preferably 2; each Y is-O- (O) C-, - (R) N- (O) C-, -C (O) -N (R) -, or-C (O) -O-, preferably-O- (O) C-; when Y is-O- (O) C-or- (R) N- (O) C-, each R¹The sum of the number of carbons plus 1 is C₆-C₂₂Is preferably C₁₂-C₂₂More preferably C₁₄-C₂₀However, the number can be up to the extent that 1R¹Or YR¹Less than about 12, and other R¹Or YR¹Is at least about 16; while each R¹Is a long chain C₅-C₂₁(or C)₆-C₂₂) Preferably C₉-C₁₉(or C)₉-C₂₀) Most preferably C₁₁-C₁₇(or C)₁₂-C₁₈) Linear, branched, unsaturated or polyunsaturated alkyl groups.

R¹Branched alkyl groups and unsaturated alkyl groups (including polyunsaturated alkyl groups) may be present, wherein the ratio of branched alkyl groups to unsaturated alkyl groups is from about 5: 95 to about 95: 5, preferably from about 75: 25 to about 25: 75, more preferably from about 50: 50 to about 30: 70, especially 35: 65.

The softener active may also contain alkyl groups, monounsaturated alkenyl groups, and polyunsaturated alkenyl groups,the softener active contains polyunsaturated alkenyl groups in an amount of at least about 3%, preferably at least about 5%, more preferably at least about 10%, and even more preferably at least 15%, based on the total weight of the softener active present. (Here, the given R is contained¹"percent softener active" is the percentage of total active that is given by the given R¹Based on all R¹Based on the percentage of the base).

Containing R¹The iodine value of the parent fatty acid of the group is preferably from about 20 to about 140, more preferably from about 50 to about 130, most preferably from about 70 to about 115; wherein the counter ion X^-Can be any anion compatible with the softening agent, preferably chloride, bromide, methosulfate, ethosulfate, sulfate, and/or nitrate, preferably chloride.

In another aspect, the fabric softening actives according to the present invention may have the general formula:wherein each Y, R¹And X^(-)Has the meaning as described above. The compounds include compounds having the general formula:

[CH₃]₃N⁽⁺⁾[CH₂CH(CH₂O(O)CR¹)O(O)CR¹]Cl^(-)Here-O (O) CR¹Part is derived from an unsaturated fatty acid such as oleic acid, and preferably each R is methyl or ethyl, preferably each R¹Are all at C₁₅To C₁₉Within the range, and with a certain degree of branching and substitution in the alkyl chain.

Mixtures of the general formulae (1) and (2) can also be prepared.

The above counterion X^(-)Any anion compatible with the softening agent may be used, preferably a strong acid anion such as chloride, bromide, methosulfate, ethosulfate, sulfate, nitrate, and the like, more preferably chloride. The anion may also, but is not preferred to, be doubly charged, in which case X^(-)Represents one half of the group.

The fabric softener active may comprise a mixture of compounds containing a branched compound and an unsaturated compound, respectively. Preferred biodegradable quaternary ammonium salt fabric softening compounds for use in making such mixtures may contain-O- (O) CR¹Groups derived from unsaturated and polyunsaturated fatty acids, e.g. oleic acid, and/or partially hydrogenated fatty acids, the latter in turnFrom vegetable oils and/or partially hydrogenated vegetable oils, such as Canola oil, safflower oil, peanut oil, sunflower oil, corn oil, soybean oil, tall oil, rice bran oil, and the like. Mixtures of unsaturated fatty acids and mixtures of DEQA derived from different unsaturated fatty acids can be used and are preferred. Non-limiting examples of DEQA prepared from preferred unsaturated fatty acids are the following DEQA¹To DEQA⁸Those disclosed.

DEQA⁶Prepared from soybean fatty acids, DEQA⁷From slightly hydrogenated tallow fatty acid, while DEQA⁸From slightly hydrogenated Canola fatty acids.

With R containing branched chains¹Radicals (e.g. at least a portion of R)¹Derived from isostearic acid) is the other part of the mixture. The fabric softener active itself comprises a mixture of branched and linear polymersChemical chain R¹Radical and unsaturated R¹Compounds of the group are also preferred. The total actives represented by branched chain groups are generally from about 5% to about 95%, preferably from about 25% to about 75%, more preferably from about 35% to about 50%.

Suitable branched chain fatty acids for use in preparing branched alkyl DEQA or DEQA containing both branched alkyl groups and unsaturated alkyl groups can be prepared by a variety of methods. The corresponding branched-chain fatty alcohols can be prepared by reducing the branched-chain fatty acids using borane-THF using standard reactions, such as the method described by Brown in j.amer.chem Soc (1970), 92, 1637 (incorporated herein by reference). The following are non-limiting examples of branched fatty acids.

Branched fatty acid 1: 2-n-heptylundecanoic acid

2-n-heptylundecanoic acid [22890-21-7 ]]From TCI america, catalog number IO 281. It is prepared by oxidizing Guerbet alcohol 2-heptyl undecyl alcohol, and 2-heptyl undecyl alcohol is aldol condensation product of nonanal. Guerbet alcohol is sold under the trade name ISOFOL by Condea^®Alcohols are commercially available.

Branched fatty acid 2: 2-n-hexyldecanoic acid

2-n-hexyldecanoic acid [25354-97-6] was obtained from TCI America under catalog number HO 507. It can be prepared from the Guerbet alcohol 2-hexyldecanol by oxidation. And 2-hexyldecanol is the aldol condensation product of octanal.

Branched fatty acid 3: 2-n-butyl octanoic acid

2-n-Butyloctanoic acid is available from Union Carbide under the tradename ISOCARB^®12 acid. It can be prepared from Guerbet alcohol 2-butyl octanol by oxidation.

Branched fatty acid 4: 5, 7, 9-trimethylnonanoic acid

5, 7, 9-Trimethylnonanoic acid and 3, 5, 7, 9-Tetramethylnonanoic acid were manufactured by Union Camp corporation using the oxo process published by N.E.Lawson et al, J.Am.oil.chem.Soc.1981, 58, 59.

Branched chain fatty acid 5: α -alkylated carboxylic acids

RR′CHCO₂H

α -substituted acids can be prepared by C-alkylation of enamines derived from linear aldehydes such as octanal or decanal the derivatized enamine will form a carbanion at the α carbon relative to the terminal nitrogen atom the enamine anion will react with a bromoalkane in the presence of a catalytic amount of NaI to form a branched enamine which will hydrolyze to a α -alkylated aldehyde the aldehyde can be oxidized to the corresponding carboxylic acid.

α Heptyldecanoic acid

The reaction mixture after alkylation (overnight) was poured onto ice and acidified with 20% HCl, this hydrolysis reaction converted the alkylated enamine to α -heptyl decanal, which can be separated, washed and then dried over a solvent layer, and then vacuum distilled to remove the solvent.

The separated branched aldehyde can then be converted to the desired carboxylic acid by oxidation in a suitable solvent. Examples of oxidizing agents are: aqueous potassium permanganate, Jones reagent in acetone (CrO)₃/H₂SO₄/H₂O)；CrO₃The high molecular weight of the acid will facilitate the separation of the desired α -heptyldecanoic acid from the oxidation medium.

Branched fatty acid 6: 9 and 10-alkoxyoctadecanoic acids, the other positional isomers, and the corresponding alkoxyoctadecanols.

9 and 10-methoxyoctadecanoic acid. Prepared as described by Siouffi et al, Chemistry and Physicsof Lipids, (1972), 8(2), 91-101. About 5 grams of methyl oleate is dissolved in about 8 grams of methanol and treated with t-butyl hypobromite to produce the mixed methoxy bromo derivative. It is separated off and debrominated with a Raney nickel catalyst, and the crude acid is separated off after acidification. The oil-based component of the crude acid was hydrogenated with platinum oxide in cyclohexane to produce the desired 9 and 10-methoxyoctadecanoic carboxylic acid.

9 and 10-isopropoxyoctadecanoic acid: the same procedure was used except that 2-propanol was used in place of methanol in the bromination step to produce the desired 9 and 10-isopropoxyoctadecanoic carboxylic acid.

Positional isomers of alkoxyoctadecanoic carboxylic acids: the same procedure was used except that oleic acid was first isomerized to a mixture of unsaturated acids by co-heating with methanesulfonic acid. In this case, the alkoxybromination-reduction produces an additional mixture of positional isomers of alkoxyoctadecanoic carboxylic acids.

The corresponding fatty alcohols: substituted octadecanoic carboxylic acids were reduced to the corresponding octadecanol with borane-THF according to the method described by Brown in j.amer.chem.soc. (1970), 92, 1637.

Branched fatty acid 7: phenyl octadecanoic acid, alkylphenyl octadecanoic acid, and the corresponding octadecanol.

Phenyl octadecanoic acid: the method described in Nakano and Foglia in Journal of the American oil chemists Society, (1984), 61(3), 569-73 was used. A single portion of about 5 grams oleic acid and about 6.91 grams benzene was treated dropwise with about 10.2 grams methanesulfonic acid at about 50 c and then stirred for about 6 hours. The reaction mixture was added to water and extracted with ether. The solvent was removed by vacuum stripping to yield a mixture of positional isomers of crude phenyloctadecanoic acid.

Methyl phenyl octadecanoic acid: this synthesis was repeated, but with toluene replacing the benzene, to produce mixed positional isomers of methylphenyloctadecanoic acid.

The corresponding octadecanol: substituted octadecanoic carboxylic acids were reduced to the corresponding octadecanols using borane-THF using the method described by Brown in j.amer.chem.soc. (1970), 92, 1637.

Branched fatty acid 8: phenoxy octadecanoic acid, hydroxyphenyl octadecanoic acid, and the corresponding octadecanol.

Hydroxyphenyl octadecanoic carboxylic acid: the method described by Nakano and Foglia in The Journal of The American Oil Chemists Society, (1984), 61(3), 569-73 was used. Oleic acid, phenol and methanesulfonic acid in a molar ratio of about 1: 5: 6 were allowed to react at about 25 ℃ for about 48 hours. The reaction mixture was added to water and extracted with diethyl ether. The extract was stripped of solvent and phenol to yield the desired crude product of the mixed positional isomer of hydroxyphenyl octadecanoic acid.

Phenoxy octadecanoic acid: this reaction was repeated with oleic acid, phenol and methanesulfonic acid in a molar ratio of about 1: 5: 2, and the crude product isolated was predominantly phenoxy octadecanoic acid but also hydroxyphenyl octadecanoic acid. The mixture of the positional isomers of phenoxy octadecanoic acid is obtained by chromatographic purification.

The corresponding octadecanol: substituted octadecanoic carboxylic acids were reduced to the corresponding octadecanols with borane-THF according to the method described by Brown in j.amer.chem.soc (1970), 92, 1637.

Branched chain fatty acid 9: isostearic acid

By the process described in U.S. Pat. No. 2812342 issued 11/5/1957 to R.M. Peters, incorporated herein by reference₁₈The monomeric acid obtained by the dimerization reaction of the fatty acid, isostearic acid is prepared.

Using the above-described branched chain fatty acids and/or corresponding branched chain fatty alcohols, suitable branched fabric softening actives can be formed which can be mixed with the above-described unsaturated fabric softening actives (DEQA) to form the fabric softening actives of the present invention. Similarly, branched fatty acids and/or alcohols may be used with unsaturated fatty acids and/or alcohols to form suitable mixed chain actives.

As noted above, other preferred DEQAs are prepared from mixtures of all of the different branched and unsaturated fatty acids present (total fatty acid mixture) as mono-DEQA, rather than blending mixtures of DEQA prepared separately from different portions of the total fatty acid mixture.

At least a major percentage of the fatty acyl groups may be unsaturated, for example from about 25 to 70%, preferably from about 50 to 65%. Polyunsaturated fatty acid groups may be used. The total amount of active containing polyunsaturated fatty acyl groups (TPU) may beAbout 3 to 30%, preferably about 5 to 25%, more preferably about 10 to 18%. Both cis and trans isomers can be used, with the cis/trans ratio preferably being from 1: 1 to about 50: 1, and the minimum being 1: 1, preferably at least 3: 1, and more preferably from about 4: 1 to about 20: 1. (as used herein, the term "comprising a given R¹"percent softener active" of radical, equal to the given R¹Relative to total R used to form total softener actives¹Percent of).

The unsaturated (including polyunsaturated) fatty acyl groups discussed above and below, when combined with branched fatty acyl groups, surprisingly produce effective softening, and also good rewet, good antistatic properties, and especially good recovery after thawing.

The combination of branched chain and unsaturated materials is easier to formulate than typical saturated branched fabric softener activators. They can form concentrated premixes that maintain their low viscosity and are therefore easy to process, e.g., pump, mix, etc. These materials, which typically contain only a small amount of solvent associated therewith, e.g., from about 5 to 20%, preferably from about 8 to 25%, more preferably from about 10 to 20% by weight of the total softener/solvent mixture, can be readily formulated into concentrated, stable compositions of the invention even at low temperatures. This ability to process actives at low temperatures is particularly important for polyunsaturated groups because it minimizes degradation. Additional protection against degradation is provided when the compound and softener composition contains an effective antioxidant and/or reducing agent as disclosed below. The use of branched chain aliphatic acyl groups improves the resistance to degradation and improves softening while maintaining flowability.

The present invention can also contain certain medium carbon chain biodegradable quaternary ammonium salt fabric softening compounds DEQA having the general formula (1) above and the general formula (2) below, wherein:

each Y is-O- (O) C-, or-C (O) -O-, preferably-O- (O) C-;

m is 2 or 3, preferably 2;

each n is 1 to 4, preferably 2;

each R substituent is C₁-C₆Alkyl, preferably methyl, ethyl, propyl, benzyl or mixtures thereof, more preferably C₁-C₃An alkyl group;

each R¹Or YR¹Is saturated C₈-C₁₄Alkyl, preferably C₁₂-C₁₄Hydrocarbyl, or substituted hydrocarbyl substituents (IV is preferably about 10 or less, more preferably less than about 5), (when Y is-O- (O) C-or- (R) N- (O) C-, the total number of carbon atoms in the acyl group is R¹+1), counterion X^-As above. Preferably X^-Phosphate is not included.

Saturated C₈-C₁₄The aliphatic acyl groups may be pure derivatives or may be of mixed chain length.

Suitable fatty acid sources for the fatty acyl groups are coconut acid, lauric acid, caprylic acid, capric acid.

To C₁₂-C₁₄(or C)₁₁-C₁₃) The hydrocarbyl groups are preferably saturated, e.g., the IV is preferably less than about 10, more preferably less than about 5.

It will be understood that the branched R and R¹The substituents may contain various groups, such as alkoxy (which acts as a branching), and a small percentage may be linear, provided that R¹Radical content maintenanceIt is substantially hydrophobic. The preferred compound can be considered as hardened ditallow dimethylammonium chloride (hereinafter "DTDMAC"), which is widely used as a fabric softener.

As is customary herein, when a diester is specified, it may in fact comprise an already present monoester. Preferably, at least about 80% of the DEQA is diester-type, and 0% to about 20% may be DEQA monoester. For example, a YR¹is-OH or-C (O) OH, and for formula 1, m is 2. The corresponding diamides and/or mixed ester-amides may also include actives bearing long-chain hydrophobic groups, e.g. a YR¹The radical is-N (R) H or-C (O) OH. Any of the disclosures, e.g., amounts, of monoester actives may be used below for the monoamide active. For softening, the percentage of monoester should be as low as possible, preferably no more than about 5%, under wash conditions with no/little detergent lingering. However, at high anionic detersive surface activityCertain monoesters may be preferred under extended conditions of detergent or laundry detergent. The total ratio of diester to monoester is from about 100: 1 to about 2: 1, preferably from about 50: 1 to about 5: 1, more preferably from 13: 1 to about 8: 1. In the case of high detergent content extensions, the diester/monoester ratio is preferably about 11: 1. The content of the monoester can be controlled in the production of DEQA.

In the practice of the present invention, the compounds described above for use as biodegradable quaternized ester-amine softeners, as exemplified below, can be prepared by standard reaction chemistry. A synthetic method for a diester-converting substance of DTDMAC, having the general formula RN (CH)₂CH₂OH)₂Two hydroxy groups of the amine of formula R¹C (O) Cl acid chloride, followed by quaternization with an alkyl halide RX to produce the desired product (wherein R and R¹As previously defined). However, it will be appreciated by those skilled in the chemical arts that this reaction procedure allows a wide selection of substrates.

Yet another DEQA softener active suitable for use in formulating fabric softening actives and the concentrated, clear liquid softener compositions of this invention has the general formula (1) above wherein one R group is C_1-4Hydroxyalkyl, preferably one in which one of the R groups is hydroxyethyl.

(2) The second type of DEQA active has the following general formula:

wherein each Y, R¹And X^(-)The meaning of (A) is as above. Such compounds include those having the general formula:

[CH₃]₃N⁽⁺⁾[CH₂CH(CH₂O(O)CR¹)O(O)CR¹]Cl^(-)where each R is methyl or ethyl, and preferably each R is¹At C₁₅～C₁₉Within the range of (1). The substitution may be present in the alkyl or unsaturated alkyl chain. Anion X in molecule^(-)The same as in DEQA (1) described above. As is conventional herein, when a diester is specified, it may actually include the monoester present. The monoester may be present in the same amount as in DEQA (1). Superior foodAn example of a compound selected from formula (2) DEQA is the "propyl" ester quaternary ammonium salt fabric softener active of the formula 1, 2-bis (acyloxy) -3-trimethylaminopropane chloride, wherein the acyl group is reacted with DEQA⁵Are the same as above.

The types of these agents and methods for their manufacture are disclosed in Naik et al, U.S. Pat. No.4137180, 1979, 30.6.9, which is hereby incorporated by reference.

In suitable softener actives (1) and (2), each R¹May be an alkyl group, a branched alkyl group, a monounsaturated unsaturated alkyl group, or a polyunsaturated alkyl group. The active may comprise branched alkyl and unsaturated alkyl groups R¹In particular in the proportions disclosed above, in a single molecule.

The DEQA herein may contain small amounts of fatty acids, which may be from unreacted raw materials used to make the DEQA, and/or as a by-product of any partial degradation (hydrolysis) of the softener active in the final composition. Preferably, the free fatty acid content should be low, preferably less than about 10%, more preferably less than about 5% by weight of the softener active.

Main solvent system

The compositions of the present invention contain less than about 40%, preferably less than about 1035%, more preferably less than about 12-25%, and still more preferably less than about 14-20% by weight of the composition of the primary solvent. The primary solvent is selected so as to minimize the impact of solvent odor in the composition and to provide a low viscosity to the final composition. For example, isopropanol is less effective and has a very strong odor, while n-propanol is more effective but still has a unique odor. Several butanols are also odorous, but can be used to achieve effective clarity/stability, especially when they are used as part of the main solvent system to reduce odor. Alcohols are selected to optimize low temperature stability. I.e., they form compositions having an acceptably low viscosity and translucency (preferably clarity) at as low as about 40F (about 4.4 c) and yet recover after storage at about 20F (about 6.7 c).

The suitability of any primary solvent for use in formulating a liquid concentrated, preferably clear, fabric softener composition with the desired stability is surprisingly selective. Suitable solvents can be selected according to 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 coefficient of the principal solvent component of the present invention is generally given in its log P log base 10.

Log P has been reported for many components; for example, the Pomona92 database from Daylight chemical information Systems, Inc. (Daylight CIS), Irvine, California holds many log P values, as well as the original references cited. However, the log P value can most conveniently be calculated from the "Clog P" program, which is available from Daylight CIS. The program also lists experimental log P values when the log P values are from the Pomona92 database. "calculated log P" (Clog P) was determined by the fragmentation method of Hansch and Leo (see A.Leo paper, published in Comprehensive medical Chemistry, Vol.4, C.Hansch, P.G.Sammens, J.B.Taylor and C.A.Ramsen, eds., p.295, Pergamon Press, 1990, incorporated herein by reference). The fragmentation method is based on the chemical structure of each component and takes into account the number and type of atoms, the attachment of atoms, and chemical bonds. The most reliable and widely used Clog P values for evaluating this physicochemical property are preferably employed in selecting the main solvent component suitable for use in the present invention. Without using experimental log P values. Other methods that can be used to calculate the Clog P value include, for example, the Crippen fragment method disclosed in j.chem.inf.comput.sci., 27, 21 (1987); viswanadhan's fragment method disclosed in j.chem.inf.comput sci., 29, 163 (1989); and Broto's method disclosed in eur.j.med.chem. -chim.Theor., 19, 71 (1984).

The principal solvent herein is selected from solvents having a Clog P value of about 0.15 to about 0.64, preferably about 0.25 to about 0.62, more preferably about 0.40 to about 0.60; the primary solvent is preferably asymmetric, and preferably has a melting point or a curing point that is liquid at about room temperature. For some purposes, low molecular weight and biodegradable solvents are also desirable. More asymmetric solvents appear to be desirable, while highly symmetric solvents with one center of symmetry, such as 1, 7-heptanediol or 1, 4-bis (hydroxymethyl) cyclohexane, when used alone, do not appear to produce a substantially clear composition even though their Clog P falls within the preferred range. One can select the most suitable primary solvent by determining whether a composition containing about 27% di (oleoyloxyethyl) dimethylammonium chloride, about 16-20% primary solvent, and about 2-4% ethanol will remain clear when stored at about 40 ° F (about 4.4 ℃) and will recover from freezing at about 0 ° F (about-18 ℃).

The most preferred primary solvent is determined from the appearance of the freeze-dried diluted composition used to treat the fabric. These diluted compositions appear to have the dispersibility of fabric softeners, exhibiting a more single layer appearance than conventional fabric softener compositions. The closer to a single layer appearance, the better the composition performance appears. These compositions have surprisingly good fabric softening properties, particularly when perfumes are added to the compositions at or near room temperature, as compared to similar compositions made by conventional methods having the same fabric softener active.

Useful primary solvents are listed below in categories such as aliphatic and/or cycloaliphatic diols having a given number of carbon atoms; a mono-alcohol; a glycerol derivative; alkoxides of glycols; and mixtures of the foregoing. Preferred primary solvents are shown in italics, and most preferred primary solvents are in bold. Reference number is the chemical Abstract service registry number (CAS No.) for compounds with this number of carbon atoms. The novel compounds are useful in methods for preparing these compounds, as identified and described below. For comparison, some of the unusable major solvents are listed below. However, unusable principal solvents can be used to make mixtures with the usable principal solvents. The primary solvents that can be used to make concentrated fabric softener compositions that meet the stability/clarity requirements described above.

Many of the primary solvents of diols having the same chemical formula can exist as a number of stereo and/or optical isomers. Each isomer is generally identified as a different CAS number. For example, 4-methyl-2, 3-hexanediol can be labeled at least as follows: 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.

For simplicity, each of the following formulas is listed as a CAS No. only. This description is intended for purposes of illustration only and is sufficient to enable the present invention. This disclosure is not intended to be limiting. Thus, it is understood that other isomers having other CAS numbers, as well as mixtures thereof, are also included. Similarly, while a CAS number is shown to contain certain specific isotopes such as deuterium, tritium, carbon-13, etc., it is understood that those species containing naturally occurring isotopes are also included, and vice versa.

TABLE I

Monohydric alcohol

CAS No. n-propanol 71-23-8

CAS No. 2-Butanol 15892-23-62-methyl-2-propanol 75-65-0 isomer unavailable 2-methyl-1-propanol 78-83-1

TABLE II

The isomers available for C6 diols CAS No.2, 3-butanediol, 2, 3-dimethyl-76-09-51, 2-butanediol, 2, 3-dimethyl-66553-15-91, 2-butanediol, 3, 3-dimethyl-59562-82-22, 3-pentanediol, 2-methyl-7795-80-42, 3-pentanediol, 3-methyl-63521-37-92, 3-pentanediol, 4-methyl-7795-79-12, 3-hexanediol 617-30-13, 4-hexanediol 922-17-81, 2-butanediol, 2-ethyl-66553-16-01, 2-pentanediol, 2-methyl-20667-05-41, 2-pentanediol, 3-methyl-159623-53-71, 2-pentanediol, the unusable isomer 1, 3-propanediol 4-methyl-72110-08-81, 2-hexanediol 6920-22-5, 2-ethyl-2-methyl-1, 3-propanediol, 2-isopropyl-1, 3-propanediol, 2-propyl-1, 3-butanediol, 2, 2-dimethyl-1, 3-butanediol, 2, 3-dimethyl-1, 3-butanediol, 2-ethyl-1, 4-butanediol, 2, 2-dimethyl-1, 4-butanediol, 2, 3-dimethyl-1, 4-butanediol, 2-Ethyl-1, 3-pentanediol, 2-methyl-1, 3-pentanediol, 3-methyl-1, 3-pentanediol, 4-methyl-1, 4-pentanediol, 2-methyl-1, 4-pentanediol, 3-methyl-1, 4-pentanediol, 4-methyl-1, 5-pentanediol, 2-methyl-1, 5-pentanediol, 3-methyl-2, 4-pentanediol, 2-methyl-2, 4-pentanediol, 3-methyl-1, 3-hexanediol, 1, 4-hexanediol, 1, 5-hexanediol, 2, 4-hexanediol, 2, 5-hexanediol

TABLE III

The C7 diols may be used as isomers CAS No.1, 3-propanediol, 2-butyl-2612-26-21, 3-propanediol, 2, 2-diethyl-115-76-41, 3-propanediol, 2- (1-methylpropyl) -33673-01-71, 3-propanediol, 2- (2-methylpropyl) -26462-20-81, 3-propanediol, 2-methylpropyl-264622-propyl-78-26-21, 2-butanediol, 2, 3, 3-trimethyl-method B1, 4-butanediol, 2-ethyl-2-methyl-76651-98-41, 4-butanediol, 2-ethyl-3-methyl-66225-34-11, 4-butanediol, 2-propyl-62946-68-31, 4-butanediol, 2-isopropyl-39497-66-01, 5-pentanediol, 2, 2-dimethyl-3121-82-21, 5-pentanediol, 2, 3-dimethyl-81554-20-31, 5-pentanediol, 2, 4-dimethyl-2121-69-91, 5-pentanediol, 3, 3-dimethyl-53120-74-42, 3-pentanediol, 2, 3-dimethyl-6931-70-02, 3-pentanediol, 2, 4-dimethyl-66225-53-42, 3-pentanediol, 3, 4-dimethyl-37164-04-82, 3-pentanediol, 4, 4-dimethyl-89851-45-63, 4-pentanediol, 2, 3-dimethyl-method B1, 5-pentanediol, 2-ethyl-14189-13-01, 6-hexanediol, 2-methyl-25258-92-81, 6-hexanediol, 3-methyl-4089-71-82, 3-hexanediol, 2-methyl-59215-55-32, 3-hexanediol, 3-methyl-139093-40-62, 3-hexanediol, 4-methyl-2, 3-hexanediol, 5-methyl-process B3, 4-hexanediol, 2-methyl-process B3, 4-hexanediol, 3-methyl-18938-47-11, 3-pentanediol 23433-04-71, 4-pentanediol 40646-07-91, 5-pentanediol 60096-09-51, 6-pentanediol 13175-27-4 is a preferred isomer of 1, 3-propanediol2-butyl-2612-26-21, 4-butanediol, 2-propyl-62946-68-31, 5-pentanediol, 2-ethyl-14189-13-02, 3-pentanediol, 2, 3-dimethyl-6931-70-02, 3-pentanediol, 2, 4-dimethyl-66225-53-42, 3-pentanediol, 3, 4-dimethyl-37164-04-82, 3-pentanediol, 4, 4-dimethyl-89851-45-63, 4-pentanediol, 2, 3-dimethyl-process B1, 6-hexanediol, 2-methyl-25258-92-81, 6-hexanediol, 3-methyl-4089-71-81, 3-heptanediol 23433-04-71, 4-heptanediol 40646-07-91, 5-heptanediol 60096-09-51, 6-heptanediol 13175-27-4, more preferably the isomer 2, 3-pentanediol, 2, 3-dimethyl-6931-70-02, 3-pentanediol, 2, 4-dimethyl-66225-53-42, 3-pentanediol, 3, 4-dimethyl-37164-04-82, 3-pentanediol, 4, 4-dimethyl-89851-45-63, 4-pentanediol, the 2, 3-dimethyl-process B-unavailable isomer 1, 3-propanediol, 2-methyl-2-isopropyl-1, 2-butanediol, 2-ethyl-2-methyl-1, 3-butanediol, 2, 2, 3-trimethyl-1, 3-butanediol, 2-ethyl-2-methyl-1, 3-butanediol, 2-ethyl-3-methyl-1, 3-butanediol, 2-isopropyl-1, 3-butanediol, 2-propyl-1, 4-butanediol, 2, 2, 3-trimethyl-1, 4-butanediol, 3-ethyl-1-methyl-1, 2-pentanediol, 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, 3-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, 4-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-2, 4-pentanediol, 2, 3-dimethyl-2, 4-pentanediol, 2, 4-dimethyl-2, 4-pentanediol, 3,3-dimethyl-1, 2-hexanediol, 2-methyl-1, 2-hexanediol, 3-methyl-1, 2-hexanediol, 4-methyl-1, 2-hexanediol, 5-methyl-1, 3-hexanediol, 2-methyl-1, 3-hexanediol, 3-methyl-1, 3-hexanediol, 4-methyl-1, 3-hexanediol, 5-methyl-1, 4-hexanediol, 2-methyl-1, 4-hexanediol, 3-methyl-1, 4-hexanediol, 4-methyl-1, 4-hexanediol, 5-methyl-1, 5-hexanediol, 2-methyl-1, 5-hexanediol, 3-methyl-1, 5-hexanediol, 4-methyl-1, 5-hexanediol, 5-methyl-2, 4-hexanediol, 2-methyl-2, 4-hexanediol, 3-methyl-2, 4-hexanediol, 4-methyl-2, 4-hexanediol, 5-methyl-2, 5-hexanediol, 2-methyl-2, 5-hexanediol, 3-methyl-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, 123807-34-1, 123807-33-0, 123807-32-9, 123807-31-8, and mixtures thereof.

TABLE IV

Octanediol isomer propanediol derivatives chemical name CAS No. available isomers 1, 3-propanediol, 2- (2-methylbutyl) -87194-40-91, 3-propanediol, 2- (1, 1-dimethylpropyl) -method D1, 3-propanediol, 2- (1, 2-dimethylpropyl) -method D1, 3-propanediol, 2- (1-ethylpropyl) -25462-28-61, 3-propanediol, 2- (1-methylbutyl) -22131-29-91, 3-propanediol, 2- (2, 2-dimethylpropyl) -method D1, 3-propanediol, 2- (3-methylbutyl) -25462-27-51, 3-propanediol, 2-butyl-2-methyl-3121-83-31, 3-propanediol, 2-ethyl-2-isopropyl-24765-55-71, 3-propanediol, 2-ethyl-2-propyl-25450-88-81, 3-propanediol, 2-methyl-2- (1-methylpropyl) -813-60-51, 3-propanediol, 2-methyl-2- (2-methylpropyl) -25462-42-41, 3-propanediol, 2-tert-butyl-2-methyl-25462-45-7 more preferably the isomer 1, 3-propanediol, 2- (1, 1-dimethylpropyl) -method D1, 3-propanediol, 2- (1, 2-dimethylpropyl) -method D1, 3-propanediol, 2- (1-ethylpropyl) -25462-28-61, 3-propanediol, 2- (2, 2-dimethylpropyl) -method D1, 3-propanediol, 2-ethyl-2-isopropyl-24765-55-71, 3-propanediol, 2-methyl-2- (1-methylpropyl) -813-60-51, 3-propanediol, 2-methyl-2- (2-methylpropyl) -25462-42-41, 3-propanediol, 2-tert-butyl-2-methyl-25462-45-7, isomer 1 which is not available, 3-propanediol, 2-pentyl-butanediol derivatives usable isomers 1, 3-butanediol, 2, 2-diethyl-99799-77-61, 3-butanediol, 2- (1-methylpropyl) -method C1, 3-butanediol, 2-butyl-83988-22-11, 3-butanediol, 2-ethyl-2, 3-dimethyl-method D1, 3-butanediol, 2- (1, 1-dimethylethyl) -67271-58-31, 3-butanediol, 2- (2-methylpropyl) -method C1, 3-butanediol, 2-methyl-2-isopropyl-method C1, 3-butanediol, 2-methyl-2-propyl-99799-79-81, 3-butanediol, 3-methyl-2-isopropyl-method C1, 3-butanediol, 3-methyl-2-propyl-method D1, 4-butanediol, 2, 2-diethyl-method H1, 4-butanediol, 2-methyl-2-propyl-method H1, 4-butanediol, 2- (1-methylpropyl) -method H1, 4-butanediol, 2-ethyl-2, 3-dimethyl-method F1, 4-butanediol, 2-ethyl-3, 3-dimethyl-method F1, 4-butanediol, 2- (1, 1-dimethylethyl) -36976-70-21, 4-butanediol, 2- (2-methylpropyl) -method F1, 4-butanediol, 2-methyl-3-propyl-90951-76-11, 4-butanediol, 3-methyl-2-isopropyl-99799-24-3 the preferred isomer 1, 3-butanediol, 2, 2-diethyl-99799-77-61, 3-butanediol, 2- (1-methylpropyl) -method C1, 3-butanediol, 2-butyl-83988-22-11, 3-butanediol, 2- (ethyl-2, 3-dimethyl) -method D1, 3-butanediol, 2- (1, 1-dimethylethyl) -67271-58-31, 3-butanediol, 2- (2-methylpropyl) -method C1, 3-butanediol, 2-methyl-2-isopropyl-method C1, 3-butanediol, 2-methyl-2-propyl-99799-79-81, 3-butanediol, 3-methyl-2-propyl-method D1, 4-butanediol, 2, 2-diethyl-method H1, 4-butanediol, 2-ethyl-2, 3-dimethyl-method F1, 4-butanediol, 2-ethyl-3, 3-dimethyl-method F1, 4-butanediol, 2- (1, 1-dimethylethyl) -36976-70-21, 4-butanediol, more preferably 3-methyl-2-isopropene-99799-24-3, isomer 1, 3-butanediol, 2- (1-methylpropyl) -method C1, 3-butanediol, 2- (2-methylpropyl) -method C1, 3-butanediol, 2-butyl-83988-22-11, 3-butanediol, 2-methyl-2-propyl 99799-79-81, 3-butanediol, 3-methyl-2-propyl-method D1, 4-butanediol, 2, 2-diethyl-method H1, 4-butanediol, 2-ethyl-2, 3-dimethyl-method F1, 4-butanediol, 2-ethyl-3, 3-dimethyl-method F1, 4-butanediol, isomer 1 which is not available as 2- (1, 1-dimethylethyl) -36976-70-2, 4-butanediol, 2-butyl-1, 2-butanediol, 2-ethyl-3, 3-dimethyl-1, 4-butanediol, 2-methyl-2-isopropyl-1, 2-butanediol, 3-methyl-2-isopropyl-1, 4-butanediol, the isomers 1, 3-pentanediol, 2, 2, 3, 3-tetramethyl-trimethylpentanediol isomers which are available, 2, 2, 3-trimethyl-35512-54-01, 3-pentanediol, 2, 2, 4-trimethyl-144-19-41, 3-pentanediol, 2, 3, 4-trimethyl-116614-13-21, 3-pentanediol, 2, 4, 4-trimethyl-109387-36, 3-pentanediol, 3, 4, 4-trimethyl-81756-50-51, 4-pentanediol, 2, 2, 3-trimethyl-process H1, 4-pentanediol, 2, 2, 4-trimethyl-80864-10-41, 4-pentanediol, 2, 3, 3-trimethyl-process H1, 4-pentanediol, 2, 3, 4-trimethyl-92340-74-41, 4-pentanediol, 3, 3, 4-trimethyl-16466-35-61, 5-pentanediol, 2, 2, 3-trimethyl-process F1, 5-pentanediol, 2, 2, 4-trimethyl-3465-14-31, 5-pentanediol, 2, 3, 3-trimethyl-Process A1, 5-pentanediol, 2, 3, 4-trimethyl-85373-83-72, 4-pentanediol, 2, 3, 3-trimethyl-24892-51-12, 4-pentanediol, the preferred isomer 1, 3-pentanediol of 2, 3, 4-trimethyl-24892-52-2, 2, 2, 3-trimethyl-35512-54-01, 3-pentanediol, 2, 2, 4-trimethyl-144-19-41, 3-pentanediol, 2, 3, 4-trimethyl-116614-13-21, 3-pentanediol, 2, 4, 4-trimethyl-109387-36-21, 3-pentanediol, 3, 4, 4-trimethyl-81756-50-51, 4-pentanediol, 2, 2, 3-trimethyl-process H1, 4-pentanediol, 2, 2, 4-trimethyl-80864-10-41, 4-pentanediol, 2, 3, 3-trimethyl-process F1, 4-pentanediol, 2, 3, 4-trimethyl-92340-74-41, 4-pentanediol, 3, 3, 4-trimethyl-16466-35-61, 5-pentanediol, 2, 2, 3-trimethyl-process A1, 5-pentanediol, 2, 2, 4-trimethyl-3465-14-31, 5-pentanediol, 2, 3, 3-trimethyl-process A2, 4-pentanediol, 2, 3, 4-trimethyl-24892-52-2, more preferably the isomer 1, 3-pentanediol, 2, 3, 4-trimethyl-116614-13-21, 4-pentanediol, 2, 3, 4-trimethyl-92340-74-41, 5-pentanediol, 2, 2, 3-trimethyl-method A1, 5-pentanediol, 2, 2, 4-trimethyl-3465-14-31, 5-pentanediol, the isomer 1, 2-pentanediol that is not available from 2, 3, 3-trimethyl-method A, 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-2, 3-pentanediol, 2, 3, 4-trimethyl-2, 3-pentanediol, 2, 4, 4-trimethyl-2, 3-pentanediol, the 1, 3-pentanediol, an available isomer of 3, 4, 4-trimethyl-ethylmethylpentanediol isomers, 2-ethyl-2-methyl-process C1, 3-pentanediol, 2-ethyl-3-methyl-process D1, 3-pentanediol, 2-ethyl-4-methyl-148904-97-61, 3-pentanediol, 3-ethyl-2-methyl 55661-71, 4-pentanediol, 2-ethyl-2-methyl-process H1, 4-pentanediol, 2-ethyl-3-methyl-process F1, 4-pentanediol, 2-ethyl-4-methyl-process G1, 4-pentanediol, 3-ethyl-2-methyl-process F1, 4-pentanediol, 3-ethyl-3-methyl-process F1, 5-pentanediol, 2-ethyl-2-methyl-process F1, 5-pentanediol, 2-ethyl-3-methyl-54886-83-81, 5-pentanediol, 2-ethyl-4-methyl-process F1, 5-pentanediol, 3-ethyl-3-methyl-57740-12-22, 4-pentanediol, the more preferred isomer of 3-ethyl-2-methyl-process G, 1, 3-pentanediol, 1, 2-ethyl-2-methyl-process C1, 3-pentanediol, 1, 2-ethyl-3-methyl-process D1, 3-pentanediol, 1, 2-ethyl-4-methyl-148904-97-61, 3-pentanediol, 3-ethyl-2-methyl-55661-05-71, 4-pentanediol, 2-ethyl-2-methyl-process H1, 4-pentanediol, 2-ethyl-3-methyl-process F1, 4-pentanediol, 2-ethyl-4-methyl-process G1, 5-pentanediol, 3-ethyl-3-methyl-57740-12-22, 4-pentanediol, 3-ethyl-2-methyl-process G the unusable isomers 1, 2-pentanediol, 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, 3-pentanediol, 3-ethyl-4-methyl-1, 4-pentanediol, 3-ethyl-4-methyl-1, 5-pentanediol, 3-ethyl-2-methyl-2, 3-pentanediol, 3-ethyl-4-methyl-2, 4-pentanediol, the isomers available as the 3-ethyl-3-methyl-propyl pentanediol isomers 1, 3-pentanediol, 2-isopropyl-process D1, 3-pentanediol, 2-propyl-process C1, 4-pentanediol, 2-isopropyl-process H1, 4-pentanediol, 2-propyl-process H1, 4-pentanediol, 3-isopropyl-process H1, 5-pentanediol, 2-isopropyl-90951-89-62, 4-pentanediol, the more preferred isomer 1, 3-pentanediol of 3-propyl-process C, 2-isopropyl-process D1, 3-pentanediol, 2-propyl-process C1, 4-pentanediol, 2-isopropyl-process H1, 4-pentanediol, 2-propyl-process H1, 4-pentanediol, 3-isopropyl-process H2, 4-pentanediol, the isomer 1, 2-pentanediol that is not available to 3-propyl-process C, 2-propyl-1, 2-pentanediol, 2-isopropyl-1, 4-pentanediol, 3-propyl-1, 5-pentanediol, 2-propyl-2, 4-pentanediol, the isomer 1 available to 3-isopropyl-dimethylhexanediol, 3-hexanediol, 2, 2-dimethyl-22006-96-81, 3-hexanediol, 2, 3-dimethyl-process D1, 3-hexanediol, 2, 4-dimethyl-78122-99-31, 3-hexanediol, 2, 5-dimethyl-process C1, 3-hexanediol, 3, 4-dimethyl-process D1, 3-hexanediol, 3, 5-dimethyl-process D1, 3-hexanediol, 4, 4-dimethyl-process C1, 3-hexanediol, 4, 5-dimethyl-process C1, 4-hexanediol, 2, 2-dimethyl-process F1, 4-hexanediol, 2, 3-dimethyl-process F1, 4-hexanediol, 2, 4-dimethyl-process G1, 4-hexanediol, 2, 5-dimethyl-22417-60-31, 4-hexanediol, 3, 3-dimethyl-process F1, 4-hexanediol, 3, 4-dimethyl-process E1, 4-hexanediol, 3, 5-dimethyl-process H1, 4-hexanediol, 4, 5-dimethyl-process E1, 4-hexanediol, 5, 5-dimethyl-38624-38-31, 5-hexanediol, 2, 2-dimethyl-process A1, 5-hexanediol, 2, 3-dimethyl-62718-05-21, 5-hexanediol, 2, 4-dimethyl-73455-82-01, 5-hexanediol, 2, 5-dimethyl-58510-28, 41, 5-hexanediol, 3, 3-dimethyl-41736-99-61, 5-hexanediol, 3, 4-dimethyl-process A1, 5-hexanediol, 3, 5-dimethyl-process G1, 5-hexanediol, 4, 5-dimethyl-process F1, 6-hexanediol, 2, 2-dimethyl-13622-91-81, 6-hexanediol, 2, 3-dimethyl-process F1, 6-hexanediol, 2, 4-dimethyl-process F1, 6-hexanediol, 2, 5-dimethyl-49623-11-21, 6-hexanediol, 3, 3-dimethyl-process F1, 6-hexanediol, 3, 4-dimethyl-65363-45-32, 4-hexanediol, 2, 3-dimethyl-26344-17-22, 4-hexanediol, 2, 4-dimethyl-29649-22-72, 4-hexanediol, 2, 5-dimethyl-3899-89-62, 4-hexanediol, 3, 3-dimethyl-42412-51-12, 4-hexanediol, 3, 4-dimethyl-90951-83-02, 4-hexanediol, 3, 5-dimethyl-159300-34-22, 4-hexanediol, 4, 5-dimethyl-process D2, 4-hexanediol, 5, 5-dimethyl-108505-10-82, 5-hexanediol, 2, 3-dimethyl-process G2, 5-hexanediol, 2, 4-dimethyl-process G2, 5-hexanediol, 2, 5-dimethyl-110-03-22, 5-hexanediol, 3, 3-dimethyl-process H2, 5-hexanediol, 3, 4-dimethyl-99799-30-12, 6-hexanediol, 3, 3-dimethyl-process A more preferably the isomer 1, 3-hexanediol, 2, 2-dimethyl-22006-96-81, 3-hexanediol, 2, 3-dimethyl-process D1, 3-hexanediol, 2, 4-dimethyl-78122-99-31, 3-hexanediol, 2, 5-dimethyl-process C1, 3-hexanediol, 3, 4-dimethyl-process D1, 3-hexanediol, 3, 5-dimethyl-process D1, 3-hexanediol, 4, 4-dimethyl-process C1, 3-hexanediol, 4, 5-dimethyl-process C1, 4-hexanediol, 2, 2-dimethyl-process H1, 4-hexanediol, 2, 3-dimethyl-process F1, 4-hexanediol, 2, 4-dimethyl-process G1, 4-hexanediol, 2, 5-dimethyl-22417-60-31, 4-hexanediol, 3, 3-dimethyl-process F1, 4-hexanediol, 3, 4-dimethyl-process E1, 4-hexanediol, 3, 5-dimethyl-process H1, 4-hexanediol, 4, 5-dimethyl-process E1, 4-hexanediol, 5, 5-dimethyl-38624-38-31, 5-hexanediol, 2, 2-dimethyl-process A1, 5-hexanediol, 2, 3-dimethyl-62718-05-21, 5-hexanediol, 2, 4-dimethyl-73455-82-01, 5-hexanediol, 2, 5-dimethyl-58510-28-41, 5-hexanediol, 3, 3-dimethyl-41736-99-61, 5-hexanediol, 3, 4-dimethyl-process A1, 5-hexanediol, 3, 5-dimethyl-process G1, 5-hexanediol, 4, 5-dimethyl-process F2, 6-hexanediol, 3, 3-dimethyl-hexanediol, the isomer 1, 2-hexanediol which is not usable for process A, 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-2, 3-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-3, 4-hexanediol, 2, 2-dimethyl-3, 4-hexanediol, 2, 3-dimethyl-3, 4-hexanediol, 2, 4-dimethyl-3, 4-hexanediol, 2, 5-dimethyl-3, 4-hexanediol, 3, 4-dimethyl-ethylhexanediol isomer, more preferably isomer 1, 3-hexanediol, 2-ethyl-94-96-21, 3-hexanediol, 4-ethyl-process C1, 4-hexanediol, 2-ethyl-148904-97-61, 4-hexanediol, 4-ethyl-1113-00-41, 5-hexanediol, 2-ethyl-58374-34-82, 4-hexanediol, 3-ethyl-process C2, 4-hexanediol, 4-ethyl-33683-47-52, 5-hexanediol, the isomer 1, 5-hexanediol which is not available in 3-ethyl-process F, 4-ethyl-1, 6-hexanediol, 2-ethyl-1, 4-hexanediol, 3-ethyl-1, 5-hexanediol, 3-ethyl-1, 6-hexanediol, 3-ethyl-1, 2-hexanediol, 2-ethyl-1, 2-hexanediol, 3-ethyl-1, 2-hexanediol, 4-ethyl-2, 3-hexanediol, 3-ethyl-2, 3-hexanediol, 4-ethyl-3, 4-hexanediol, 3-ethyl-1, 3-hexanediol, the usable isomer 1, 3-heptanediol of the 3-ethyl-methylheptanediol isomer, 2-methyl-109417-38-11, 3-heptanediol, 3-methyl-165326-88-51, 3-heptanediol, 4-methyl-process C1, 3-heptanediol, 5-methyl-process D1, 3-heptanediol, 6-methyl-process C1, 4-heptanediol, 2-methyl-15966-03-71, 4-heptanediol, 3-methyl-7748-38-11, 4-heptanediol, 4-methyl-72473-94-01, 4-heptanediol, 5-methyl-003-04-31, 4-heptanediol, 6-methyl-99799-25-41, 5-heptanediol, 2-methyl-141605-00-71, 5-heptanediol, 3-methyl-process A1, 5-heptanediol, 4-methyl-process A1, 5-heptanediol, 5-methyl-99799-26-51, 5-heptanediol, 6-methyl-57740-00-81, 6-heptanediol, 2-methyl-132148-22-21, 6-heptanediol, 3-methyl-process G1, 6-heptanediol, 4-methyl-156307-84-51, 6-heptanediol, 5-methyl-process A1, 6-heptanediol, 6-methyl-5392-57-42, 4-heptanediol, 2-methyl-38836-26-92, 4-heptanediol, 3-methyl-6964-04-12, 4-heptanediol, 4-methyl-165326-87-42, 4-heptanediol, 5-methyl-process C2, 4-heptanediol, 6-methyl-79356-95-92, 5-heptanediol, 2-methyl-141605-02-92, 5-heptanediol, 3-methyl-Process G2, 5-heptanediol, 4-methyl-156407-38-42, 5-heptanediol, 5-methyl-148843-72-52, 5-heptanediol, 6-methyl-51916-46-22, 6-heptanediol, 2-methyl-73304-48-02, 6-heptanediol, 3-methyl-29915-96-62, 6-heptanediol, 4-methyl-106257-69-63, 4-heptanediol, 3-methyl-18938-50-63, 5-heptanediol, 2-methyl-process C3, 5-heptanediol, 3-methyl-99799-27-63, 5-heptanediol, 4-methyl-156407-37-3, more preferably the isomer 1, 3-heptanediol, 2-methyl-109417-38-11, 3-heptanediol, 3-methyl-165326-88-51, 3-heptanediol, 4-methyl-process C1, 3-heptanediol, 5-methyl-process D1, 3-heptanediol, 6-methyl-process C1, 4-heptanediol, 2-methyl-15966-03-71, 4-heptanediol, 3-methyl-7748-38-11, 4-heptanediol, 4-methyl-72473-94-01, 4-heptanediol, 5-methyl-63003-04-31, 4-heptanediol, 6-methyl-99799-25-41, 5-heptanediol, 2-methyl-141605-00-71, 5-heptanediol, 3-methyl-process A1, 5-heptanediol, 4-methyl-process A1, 5-heptanediol, 5-methyl-99799-26-51, 5-heptanediol, 6-methyl-57740-00-81, 6-heptanediol, 2-methyl-132148-22-21, 6-heptanediol, 3-methyl-process G1, 6-heptanediol, 4-methyl-156307-84-51, 6-heptanediol, 5-methyl-Process A1, 6-heptanediol, 6-methyl-5392-57-42, 4-heptanediol, 2-methyl-38836-26-92, 4-heptanediol, 3-methyl-6964-04-12, 4-heptanediol, 4-methyl-165326-87-42, 4-heptanediol, 5-methyl-Process C2, 4-heptanediol, 6-methyl-79356-95-92, 5-heptanediol, 2-methyl-141605-02-92, 5-heptanediol, 3-methyl-Process H2, 5-heptanediol, 4-methyl-156407-38-42, 5-heptanediol, 5-methyl-148843-72-52, 5-heptanediol, 6-methyl-51916-46-22, 6-heptanediol, 2-methyl-73304-48-02, 6-heptanediol, 3-methyl-29915-96-62, 6-heptanediol, 4-methyl-106257-69-63, 4-heptanediol, 3-methyl-18938-50-63, 5-heptanediol, 2-methyl-process C3, 5-heptanediol, 4-methyl-156407-37-3 unusable isomer 1, 7-heptanediol, 2-methyl-1, 7-heptanediol, 3-methyl-1, 7-heptanediol, 4-methyl-2, 3-heptanediol, 2-methyl-2, 3-heptanediol, 3-methyl-2, 3-heptanediol, 4-methyl-2, 3-heptanediol, 5-methyl-2, 3-heptanediol, 6-methyl-3, 4-heptanediol, 2-methyl-3, 4-heptanediol, 4-methyl-3, 4-heptanediol, 5-methyl-3, 4-heptanediol, 6-methyl-1, 2-heptanediol, 2-methyl-1, 2-heptanediol, 3-methyl-1, 2-heptanediol, 4-methyl-1, 2-heptanediol, 5-methyl-1, 2-heptanediol, 6-methyl-octanediol isomer, more preferably isomer 2, 4-octanediol 90162-24-62, 5-octanediol 4527-78-02, 6-octanediol Process A2, 7-octanediol 19686-96-53, 5-octanediol 24892-55-53, 6-octanediol 24434-09-1 the unusable isomer 1, 2-octanediol 1117-86-81, 3-octanediol 23433-05-81, 4-octanediol 51916-47-31, 5-octanediol 2736-67-61, 6-octanediol 4060-76-61, 7-octanediol 13175-32-11, 8-octanediol 629-41-42, 3-octanediols such as 98464-24-53, 4-octanediols such as 99799-31-23, 5-octanediols such as 129025-63-4

TABLE V

Nonanediol isomer chemical name CAS No. preferred isomer 2, 4-pentanediol, 2, 3, 3, 4-tetramethyl-19424-43-2 the available isomer 2, 4-pentanediol, 3-tert-butyl-142205-14-92, 4-hexanediol, 2, 5, 5-trimethyl-97460-08-72, 4-hexanediol, 3, 3, 4-trimethyl-method D2, 4-hexanediol, 3, 3, 5-trimethyl-27122-58-32, 4-hexanediol, 3, 5, 5-trimethyl-method D2, 4-hexanediol, 4, 5, 5-trimethyl-method D2, 5-hexanediol, 3, 3, 4-trimethyl-method H2, more than 500 isomers are not available from 5-hexanediol, 3, 3, 5-trimethyl-process G, including the following: 2, 4-hexanediol, 2, 4, 5-trimethyl-36587-81-22, 4-hexanediol, 2, 3, 5-trimethyl-, erythro 26344-20-72, 4-hexanediol, 2, 3, 5-trimethyl-, threo 26343-49-71, 3-propanediol, 2-butyl-2-ethyl-115-84-42, 4-hexanediol, 2, 3, 5-trimethyl-, threo 26343-49-7

TABLE VI

Preferred monoglyceryl ethers and derivatives of alkyl glyceryl ethers, di (hydroxyalkyl) ethers, and aryl glyceryl ethers are 1, 2-propanediol, 3- (butoxy) -, triethoxylated 1, 2-propanediol, 3- (butoxy) -, more preferred monoglyceryl ethers and derivatives of tetraethoxylated CAS No.1, 2-propanediol, 3- (n-pentyloxy) -22636-32-41, 2-propanediol, 3- (2-pentyloxy) -1, 2-propanediol, 3- (3-pentyloxy) -1, 2-propanediol, 3- (2-methyl-1-butoxy) -1, 2-propanediol, 3- (isopentyloxy) -1, 2-propanediol, 3- (3-methyl-2-butoxy) -1, 2-propanediol, 3- (cyclohexyloxy) -1, 2-propanediol, 3- (1-cyclohex-1-enyloxy) -1, 3-propanediol, 2- (pentyloxy) -1, 3-propanediol, 2- (2-pentyloxy) -1, 3-propanediol, 2- (3-pentyloxy) -1, 3-propanediol, 2- (2-methyl-1-butoxy) -1, 3-propanediol, 2- (isopentyloxy) 1, 3-propanediol, 2- (3-methyl-2-butoxy) -1, 3-propanediol, 2- (cyclohexyloxy) -1, 3-propanediol, 2- (1-cyclohex-1-enyloxy) -1, 2-propanediol, 3- (butoxy) -, pentaethoxylated 1, 2-propanediol, 3- (butoxy) -, hexaethoxylated 1, 2-propanediol, 3- (butoxy) -, heptaethoxylated 1, 2-propanediol, 3- (butoxy) -, octaethoxylated 1, 2-propanediol, 3- (butoxy) -, nonaethoxylated 1, 2-propanediol, 3- (butoxy) -, monopropoxylated 1, 2-propanediol, 3- (butoxy) -, dibutoxylated 1, 2-propanediol, 3- (butoxy) -, tributoxylated more preferred bis (hydroxyalkyl) ether bis (2-hydroxybutyl) ether bis (2-hydroxycyclopentyl) ether the monoglyceryl ether 1, 2-propanediol, 3-ethoxy-1, 2-propanediol, 3-propoxy-1, 2-propanediol, 3-isopropoxy-1, 2-propanediol, 3-butoxy-1, 2-propanediol, 3-isobutoxy-1, 2-propanediol, 3-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, 3-propanediol, 2- (1-cyclohex-2-enyloxy) -

Aromatic Glycerol Ether usable are aromatic glycerol ether 1, 2-propanediol, 3-phenoxy-1, 2-propanediol, 3-benzyloxy-1, 2-propanediol, 3- (2-phenylethoxy) -1, 2-propanediol, 3- (1-phenyl-2-propoxy) -1, 3-propanediol, 2-phenoxy-1, 3-propanediol, 2- (m-tolyloxy) -1, 3-propanediol, 2- (p-tolyloxy) -1, 3-propanediol, 2-benzyloxy-1, 3-propanediol, 2- (2-phenylethoxy) -1, 3-propanediol, 2- (1-phenylethoxy) -preferably aromatic glycerol ether 1, 2-propanediol, 3-phenoxy-1, 2-propanediol, 3-benzyloxy-1, 2-propanediol, 3- (2-phenylethoxy) -1, 3-propanediol, 2- (m-tolyloxy) -1, 3-propanediol, 2- (p-tolyloxy) -1, 3-propanediol, 2- (benzyloxy) -1, 3-propanediol, 2- (2-phenylethoxy) -preferably aromatic glycerol ether 1, 2-propanediol, 3-phenoxy-1, 2-propanediol, 3-benzyloxy-1, 2-propanediol, 3- (2-phenylethoxy) -1, 3-propanediol, 2- (m-tolyl) -1, 3-propanediol, 2- (p-tolyl) -1, 3-propanediol, 2- (2-phenethyloxy) -

TABLE VII

Alicyclic diols and derivatives chemical name CAS No. preferred cyclic diols and derivatives 1-isopropyl-1, 2-cyclobutanediol 59895-32-83-ethyl-4-methyl-1, 2-cyclobutanediol 3-propyl-1, 2-cyclobutanediol 3-isopropyl-1, 2-cyclobutanediol 42113-90-61-ethyl-1, 2-cyclopentanediol 67396-17-21, 2-dimethyl-1, 2-cyclopentanediol 33046-20-71, 4-dimethyl-1, 2-cyclopentanediol 89794-56-92, 4, 5-trimethyl-1, 3-cyclopentanediol 3, 3-dimethyl-1, 2-cyclopentanediol 89794-57-03, 4-dimethyl-1, 2-cyclopentanediol 70051-69-33, 5-dimethyl-1, 2-cyclopentanediol 89794-58-13-ethyl-1, 2-cyclopentanediol 4, 4-dimethyl-1, 2-cyclopentanediol 70197-54-54-ethyl-1, 2-cyclopentanediol 1, 1-bis (hydroxymethyl) cyclohexane 2658-60-81, 2-bis (hydroxymethyl) cyclohexane 76155-27-61, 2-dimethyl-1, 3-cyclohexanediol 53023-07-71, 3-bis (hydroxymethyl) cyclohexane 13022-98-51, 3-dimethyl-1, 3-cyclohexanediol 128749-93-91, 6-dimethyl-1, 3-cyclohexanediol 164713-16-01-hydroxy-cyclohexylethanol 40894-17-51-hydroxy-cyclohexylmethanol 15753-47-61-ethyl-1, 3-cyclohexanediol 10601-18-01-methyl-1, 2-cyclohexanediol 52718-65-72, 2-dimethyl-1, 3-cyclohexanediol 114693-83-32, 3-dimethyl-1, 4-cyclohexanediol 70156-82-02, 4-dimethyl-1, 3-cyclohexanediol 2, 5-dimethyl-1, 3-cyclohexanediol 2, 6-dimethyl-1, 4-cyclohexanediol 34958-42-42-ethyl-1, 3-cyclohexanediol 155433-88-82-hydroxycyclohexaneethanol 24682-42-62-hydroxyethyl-1-cyclohexanol 2-hydroxymethylcyclohexanol 89794-52-53-hydroxyethyl-1-cyclohexanol 3-hydroxycyclohexaneethanol 86576-87-63-hydroxymethylcyclohexanol 3-methyl-1, 2-cyclohexanediol 23477-91-04, 4-dimethyl-1, 3-cyclohexanediol 14203-50-04, 5-dimethyl-1, 3-cyclohexanediol 4, 6-dimethyl-1, 3-cyclohexanediol 16066-66-34-ethyl-1, 3-cyclohexanediol 4-hydroxyethyl-1-cyclohexanol 4-hydroxymethyl-cyclohexanol 33893-85-54-methyl-1, 2-cyclohexanediol 23832-27-15, 5-dimethyl-1, 3-cyclohexanediol 51335-83-25-ethyl-1, 3-cyclohexanediol 1, 2-cycloheptanediol 108268-28-62-methyl-1, 3-cycloheptanediol 101375-80-82-methyl-1, 4-cycloheptanediol 4-methyl-1, 3-cycloheptanediol 5-methyl-1, 4-cycloheptanediol 90201-00-66-methyl-1, 4-cycloheptanediol 1, 3-cyclooctanediol 101935-36-81, 4-cyclooctanediol 73982-04-41, 5-cyclooctanediol 23418-82-81, 2-cyclohexanediol, 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, nonaethoxylate 1, 2-cyclohexanediol, monopropoxylate 1, 2-cyclohexanediol, monobutoxide 1, 2-cyclohexanediol, dibutoxylate 1, 2-cyclohexanediol, the tributoxylate chemical name CAS No. the more preferred cyclic diol and derivative 1-isopropyl-1, 2-cyclobutanediol 59895-32-83-ethyl-4-methyl-1, 2-cyclobutanediol 3-propyl-1, 2-cyclobutanediol 3-isopropyl-1, 2-cyclobutanediol 42113-90-61-ethyl-1, 2-cyclopentanediol 67396-17-21, 2-dimethyl-1, 2-cyclopentanediol 33046-20-71, 4-dimethyl-1, 2-cyclopentanediol 89794-56-93, 3-dimethyl-1, 2-cyclopentanediol 89794-57-03, 4-dimethyl-1, 2-Cyclopentanediol 70051-69-33, 5-dimethyl-1, 2-cyclopentanediol 89794-58-13-ethyl-1, 2-cyclopentanediol 4, 4-dimethyl-1, 2-cyclopentanediol 70197-54-54-ethyl-1, 2-cyclopentanediol 1, 1-bis (hydroxymethyl) cyclohexane 2658-60-81, 2-bis (hydroxymethyl) cyclohexane 76155-27-61, 2-dimethyl-1, 3-cyclohexanediol 53023-07-71, 3-bis (hydroxymethyl) cyclohexane 13022-98-51-hydroxy-cyclohexanemethanol 15753-47-61-methyl-1, 2-cyclohexanediol 52718-65-73-hydroxymethylcyclohexanol 3-methyl- 1, 2-cyclohexanediol 23477-91-04, 4-dimethyl-1, 3-cyclohexanediol 14203-50-04, 5-dimethyl-1, 3-cyclohexanediol 4, 6-dimethyl-1, 3-cyclohexanediol 16066-66-34-ethyl-1, 3-cyclohexanediol 4-hydroxyethyl-1-cyclohexanol 4-hydroxymethylcyclohexanol 33893-85-54-methyl-1, 2-cyclohexanediol 23832-27-11, 2-cycloheptanediol 108268-28-61, 2-cyclohexanediol, pentaoxide 1, 2-cyclohexanediol, hexaoxide 1, 2-cyclohexanediol, heptaoxide 1, 2-cyclohexanediol, octa-ethoxylate 1, 2-cyclohexanediol, nona-ethoxylate 1, 2-cyclohexanediol, monopropoxide 1, 2-cyclohexanediol, dibutoxide

Unsaturated alicyclic diols including the following known unsaturated alicyclic diols: unsaturated alicyclic diols which can be used are chemical names CAS No.1, 2-cyclobutanediol, 1-vinyl-2-ethyl-58016-14-13-cyclobutene-1, 2-diol, 1, 2, 3, 4-tetramethyl-90112-64-43-cyclobutene-1, 2-diol, 3, 4-diethyl-142543-60-03-cyclobutene-1, 2-diol, 3- (1, 1-dimethylethyl) -142543-56-43-cyclobutene-1, 2-diol, 3-butyl-142543-55-31, 2-cyclopentanediol, 1, 2-dimethyl-4-methylene-103150-02-31, 2-cyclopentanediol, 1-ethyl-3-methylene-90314-52-61, 2-cyclopentanediol, 4- (1-propenyl) -128173-45-53-cyclopentene-1, 2-diol, 1-ethyl-3-methyl-90314-43-51, 2-cyclohexanetriol, 1-vinyl-134134-16-01, 2-cyclohexanediol, 1-methyl-3-methylene-98204-78-51, 2-cyclohexanediol, 1-methyl-4-methylene-133358-53-91, 2-cyclohexanediol, 3-vinyl-55310-51-51, 2-cyclohexanediol, 4-vinyl-85905-16-43-cyclohexene-1, 2-diol, 2, 6-dimethyl-81969-75-73-cyclohexene-1, 2-diol, 6, 6-dimethyl-61875-93-24-cyclohexene-1, 2-diol, 3, 6-dimethyl-156808-73-04-cyclohexene-1, 2-diol, 4, 5-dimethyl-154351-54-93-cyclooctene-1, 2-diol 170211-27-54-cyclooctene-1, 2-diol 124791-61-35-cyclooctene-1, 2-diol 117468-07-2, unsaturated cyclic diol 1 which is not available, 2-cyclopentanediol, 1- (1-methylvinyl) -61447-83-41, 2-propanediol, 1-cyclopentyl-55383-20-51, 3-cyclopentanediol, 2- (1-methylethylidene) -65651-46-91, 3-propanediol, 2- (1-cyclopenten-1-yl) -77192-43-91, 3-propanediol, 2- (2-cyclopenten-1-yl) -25462-31-11, 2-ethanediol, 1- (1-cyclohexen-1-yl) -151674-61-21, 2-ethanediol, 1- (3-cyclohexen-1-yl) -64011-53-62-cyclohexen-1, 4-diol, 5, 5-dimethyl-147274-55-34-cyclohexene-1, 3-diol, 3, 6-dimethyl-127716-90-91, 3-cycloheptanediol, 2-methylene-132292-67-25-cycloheptene-1, 3-diol, 1-methyl-160813-33-25-cycloheptene-1, 3-diol, 5-methyl-160813-32-12-cyclooctene-1, 4-diol 37996-40-0

TABLE VIII

C₃-C₇Diol epoxidised derivatives

In the tables below, "EO" refers to the polyethoxylate, i.e., - (CH)₂CH₂O)_nH; Me-En methyl-terminated polyethoxylates- (CH)₂CH₂O)_nCH₃(ii) a "2 (Me-En)" means that two Me-En are required; "PO" refers to the polypropoxylate- (CH)₃)CH₂O)_nH; "BO" refers to poly-butoxy- (CH)₂CH₃)CH₂O)_nH; and "n-BO" means poly (n-butoxy or poly (tetramethylene) oxy- (CH)₂CH₂CH₂CH₂O)_nH. The alkoxylated derivatives indicated are all usable and those which are preferred are listed in bold type on the second row. Non-limiting exemplary synthetic methods for preparing alkoxylated derivatives are given below.

TABLE VIIIA

Basic substance (a)	Basic substance CAS No.	EO′s	1(Me -En)	2(Me -En)	PO′s	n- BO′s	BO′s
										(b)	(c)	(d)	(e)	(f)	(g)
1, 2-propanediol (C3)	57-55-6			1-4 3-4	4
								The concentration of 1, 2-propanediol is, 2-methyl- (C4)	558-43-0		4-10 8-10	1	3		1

1, 3-propanediol (C3)	504-63-2			6-8 8	5-6 6
								The concentration of 1, 3-propanediol is, 2, 2-diethyl- (C7)	115-76-4	1-7 4-7			1	1-2 2
The concentration of 1, 3-propanediol is, 2, 2-dimethyl- (C5)	126-30-7			1-2	3-4 4
								The concentration of 1, 3-propanediol is, 2- (1-methylpropyl) - (C7)	33673-01-7	1-7 4-7			1	1-2 2
The concentration of 1, 3-propanediol is, 2- (2-methylpropyl) - (C7)	26462-20-8	1-7 4-7			1	1-2 2
								The concentration of 1, 3-propanediol is, 2-ethyl- (C5)	2612-29-5		6-10 9-10	1	3
The concentration of 1, 3-propanediol is, 2-Ethyl-2-methyl- (C6)	77-84-9		1-6 3-6		2		1
								The concentration of 1, 3-propanediol is, 2-isopropyl- (C6)	2612-27-3		1-6 3-6		2		1
The concentration of 1, 3-propanediol is, 2-methyl- (C4)	2163-42-0			2-5 4-5	4-5 5		2
								The concentration of 1, 3-propanediol is, 2-methyl-2-isopropyl- (C7)	2109-23-1	2-9 6-9			1	1-3 2-3
The concentration of 1, 3-propanediol is, 2-methyl-2-propyl- (C7)	78-26-2	1-7 4-7			1	1-2 2
								The concentration of 1, 3-propanediol is, 2-propyl- (C6)	2612-28-4		1-4		2		1

(a) In both the above table and table VIII below, the number of alkoxylated groups shown are all useful, with the usual ranges listed in the first row and those preferred are shown in bold font, juxtaposed in the second row.

(b) The numbers in this column are those of the polyethoxylated derivatives of (CH)₂CH₂O) average number of radicals.

(c) The numbers in this column are for the (CH) mono-methyl terminated polyethoxylate substituent in each derivative₂CH₂O) average number of bases.

(d) The numbers in this column are for each bis-methyl terminated polyethoxylate substituent in each derivative (CH)₂CH₂O) average number of bases.

(e) The numbers in this column are those of (CH) in the polypropoxylated derivative₃)CH₂O) average number of radicals.

(f) The numbers in this column are (CH) in the polytetramethyleneoxylated derivatives₂CH₂CH₂CH₂O) average number of radicals.

(g) The numbers in this column are those of (CH) in the multibutoxylated derivatives₂CH₃)CH₂O) average number of radicals.

TABLE VIIIB

Basic substance (a)	Basic substance CAS No.	EO′s	1(Me -En)	2(Me -En)	PO′s	n- BO′s	BO′s
										(b)	(c)	(d)	(e)	(f)	(g)
1, 2-butanediol (C4)	584-03-2		2-8 6-8		2-3		1
								1, 2-butanediol, 2, 3-dimethyl- (C6)	66553-15-9	1-6 2-5				1-2 1
1, 2-butanediol, 2-ethyl- (C6)	66553-16-0	1-3				1
								1, 2-butanediol, 2-methyl- (C5)	41051-72-3		1-2		1
1, 2-butanediol, 3, 3-dimethyl- (C6)	59562-82-2	1-6 2-5				1-2 1
								1, 2-butanediol, 3-methyl- (C5)	50468-22-9		1-2		1
1, 3-butanediol (C4)	107-88-0			3-6 5-6	5		2

1, 3-butanediol, 2, 2, 3-trimethyl- (C7)	16343-75-2		1-3		1-2 2
								1, 3-butanediol, 2, 2-dimethyl- (C6)	76-35-7		3-8 6-8		3
1, 3-butanediol, 2, 3-dimethyl- (C6)	24893-35-4		3-8 6-8		3
								1, 3-butanediol, 2-ethyl- (C6)	66553-17-1		1-6 4-6		2to3		1
1, 3-butanediol, 2-Ethyl-2-methyl- (C7)	Method C		1		1	2-4 3
								1, 3-butanediol, 2-ethyl-3-methyl- (C7)	68799-03-1		1		1	2-4 3
1, 3-butanediol, 2-isopropyl- (C7)	66567-04-2		1		1	2-4 3
								1, 3-butanediol, 2-methyl- (C5)	684-84-4			1-3 2-3	4
1, 3-butanediol, 2-propyl- (C7)	66567-03-1	2-9 6-8			1	1-3 2-3
								1, 3-butanediol, 3-methyl- (C5)	2568-33-4			1-3 2-3	4
1, 4-butanediol (C4)	110-63-4			2-4 3-4	4-5 4-5		2
								1, 4-butanediol, 2, 2, 3-trimethyl- (C7)	162108-60-3	2-9 6-9			1	1-3 2-3
1, 4-butanediol, 2, 2-dimethyl- (C6)	32812-23-0		1-6 3-6		2		1
								1, 4-butanediol, 2, 3-dimethyl- (C6)	57716-80-0		1-6 3-6		2		1
1, 4-butanediol, 2-ethyl- (C6)	57716-79-7		1-4		2		1

1, 4-butanediol, 2-Ethyl-2-methyl- (C7)	76651-98-4	1-7 4-7			1	1-2 2
								1, 4-butanediol, 2-ethyl-3-methyl- (C7)	66225-34-1	1-7 4-7			1	1-2 2
1, 4-butanediol, 2-isopropyl- (C7)	39497-66-0	1-7 4-7			1	1-2 2
								1, 4-butanediol, 2-methyl- (C5)	2938-98-9		6-10 9-10	1	3		1
1, 4-butanediol, 2-propyl- (C7)	62946-68-3	1-5 2-5				1-2 1
								1, 4-butanediol, 3-ethyl-1-methyl- (C7)	Method F	2-9 6-8			1	1-3 2-3
2, 3-butanediol (C4)	513-85-9		6-10 9-10	1	3-4		1
								The content of the 2, 3-butanediol, 2, 3-dimethyl- (C6)	76-09-5	3-9 7-9			1	1-3 2-3
The content of the 2, 3-butanediol, 2-methyl- (C5)	5396-58-7		1-5 2-5		2		1

(a) The number of alkoxylated groups shown in the above table are all usable, with the usual ranges listed in the first row, while those preferred are shown in bold font, juxtaposed in the second row.

(b) The numbers in this column are those of the polyethoxylated derivatives of (CH)₂CH₂O) average number of radicals.

(c) The number in this column is each derivativeOf monomethyl-terminated polyethoxylate substituents (CH)₂CH₂O) average number of bases.

(d) The numbers in this column are for each bis-methyl terminated polyethoxylate substituent in each derivative (CH)₂CH₂O) average number of bases.

(e) The numbers in this column are those of (CH) in the polypropoxylated derivative₃)CH₂O) average number of radicals.

(f) The numbers in this column are (CH) in the polytetramethyleneoxylated derivatives₂CH₂CH₂CH₂O)The average number of radicals.

(g) The numbers in this column are those of (CH) in the multibutoxylated derivatives₂CH₃)CH₂O) average number of radicals.

TABLE VIIIC

Basic substance (a)	Basic substance CAS No.	EO′s	1(Me -En)	2(Me -En)	PO′s	n- BO′s	BO′s
										(b)	(c)	(d)	(e)	(f)	(g)
1, 2-pentanediol (C5)	5343-92-0	3-10 7-10			1	2-3 3
								The concentration of the 1, 2-pentanediol, 2-methyl- (C6)	20667-05-4	1-3				1
The concentration of the 1, 2-pentanediol, 3-methyl- (C6)	159623-53-7	1-3				1
								The concentration of the 1, 2-pentanediol, 4-methyl- (C6)	72110-08-8	1-3				1
1, 3-pentanediol (C5)	3174-67-2			1-2	3-4
								The concentration of 1, 3-pentanediol, 2, 2-dimethyl- (C7)	2157-31-5		1		1	2-4 3
The concentration of 1, 3-pentanediol, 2, 3-dimethyl- (C7)	66225-52-3		1		1	2-4 3
								The concentration of 1, 3-pentanediol, 2, 4-dimethyl- (C7)	60712-38-1		1		1	2-4 3
The concentration of 1, 3-pentanediol, 2-ethyl- (C7)	29887-11-4	2-9 6-8			1	1-3 2-3
								The concentration of 1, 3-pentanediol, 2-methyl- (C6)	149-31-5		1-6 4-6		2-3		1
The concentration of 1, 3-pentanediol, 3, 4-dimethyl- (C7)	129851-50-9		1		1	2-4 3

The concentration of 1, 3-pentanediol, 3-methyl- (C6)	33879-72-0		1-6 4-6		2-3		1
								The concentration of 1, 3-pentanediol, 4, 4-dimethyl- (C7)	30458-16-3		1		1	2-4 3
The concentration of 1, 3-pentanediol, 4-methyl- (C6)	54876-99-2		1-6 4-6		2-3		1
								1, 4-pentanediol (C5)	626-95-9			1-2	3-4
The concentration of 1, 4-pentanediol, 2, 2-dimethyl- (C7)	Method F		1		1	2-4 3
								The concentration of 1, 4-pentanediol, 2, 3-dimethyl- (C7)	Method F		1		1	2-4 3
The concentration of 1, 4-pentanediol, 2, 4-dimethyl- (C7)	Method F		1		1	2-4 3
								The concentration of 1, 4-pentanediol, 2-methyl- (C6)	6287-17-8		1-6 4-6		2-3		1
The concentration of 1, 4-pentanediol, 3, 3-dimethyl- (C7)	81887-62-9		1		1	2-4 3
								The concentration of 1, 4-pentanediol, 3, 4-dimethyl- (C7)	63521-36-8		1		1	2-4 3
The concentration of 1, 4-pentanediol, 3-methyl- (C6)	26787-63-3		1-6 4-6		2-3		1
								The concentration of 1, 4-pentanediol, 4-methyl- (C6)	1462-10-8		1-6 4-6		2-3		1
1, 5-pentanediol (C5)	111-29-5		4-10 8-10	1	3
								The concentration of 1, 5-pentanediol, 2, 2-dimethyl- (C7)	3121-82-2	1-7 4-7			1	1-2 2
The concentration of 1, 5-pentanediol, 2, 3-dimethyl- (C7)	81554-20-3	1-7 4-7			1	1-2 2

The concentration of 1, 5-pentanediol, 2, 4-dimethyl- (C7)	2121-69-9	1-7 4-7			1	1-2 2
								The concentration of 1, 5-pentanediol, 2-ethyl- (C7)	14189-13-0	1-5 2-5				1-2 1
The concentration of 1, 5-pentanediol, 2-methyl- (C6)	42856-62-2		1-4		2
								The concentration of 1, 5-pentanediol, 3, 3-dimethyl- (C7)	53120-74-4	1-7 4-7			1	1-2 2
The concentration of 1, 5-pentanediol, 3-methyl- (C6)	4457-71-0		1-4		2
								2, 3-pentanediol (C5)	42027-23-6		1-3		2
The content of 2, 3-pentanediol, 2-methyl- (C6)	7795-80-4	1-7 4-7			1	1-2 2
								The content of 2, 3-pentanediol, 3-methyl- (C6)	63521-37-9	1-7 4-7			1	1-2 2
The content of 2, 3-pentanediol, 4-methyl- (C6)	7795-79-1	1-7 4-7			1	1-2 2
								2, 4-pentanediol (C5)	625-69-4			1-4 2-4	4
The content of 2, 4-pentanediol, 2, 3-dimethyl- (C7)	24893-39-8		1-4 2-4		2
								The content of 2, 4-pentanediol, 2, 4-dimethyl- (C7)	24892-49-7		1-4 2-4		2
The content of 2, 4-pentanediol, 2-methyl- (C6)	107-41-5		5-10 8-10		3
								The content of 2, 4-pentanediol, 3, 3-dimethyl- (C7)	24892-50-0		1-4 2-4		2
The content of 2, 4-pentanediol, 3-methyl- (C6)	Method H		5-10 8-10		3

(a) The number of alkoxylated groups shown in the above table are all usable, with the usual ranges listed in the first row, while those preferred are shown in bold font, juxtaposed in the second row.

(b) The numbers in this column are those of the polyethoxylated derivatives of (CH)₂CH₂O) average number of radicals.

(c) The numbers in this column are for the (CH) mono-methyl terminated polyethoxylate substituent in each derivative₂CH₂O) average number of bases.

(d) The numbers in this column are for each bis-methyl terminated polyethoxylate substituent in each derivative (CH)₂CH₂O) average number of bases.

(e) The numbers in this column are those of (CH) in the polypropoxylated derivative₃)CH₂O) average number of radicals.

(f) The numbers in this column are (CH) in the polytetramethyleneoxylated derivatives₂CH₂CH₂CH₂O) average number of radicals.

(g) The numbers in this column are those of (CH) in the multibutoxylated derivatives₂CH₃)CH₂O) average number of radicals.

Table VIIID

Basic substance(a)	Basic substance CAS No.	EO′s	1(Me -En)	PO′s	n- BO′s	BO′s
									(b)	(c)	(e)	(f)	(g)
1, 3-hexanediol (C6)	21531-91-9		1-5 2-5	2		1
							The concentration of 1, 3-hexanediol, 2-methyl- (C7)	66072-21-7	2-9 6-8		1	1-3 2-3	1
The concentration of 1, 3-hexanediol, 3-methyl- (C7)	Method D	2-9 6-8		1	1-3 2-3
							The concentration of 1, 3-hexanediol, 4-methyl- (C7)	Method C	2-9 6-8		1	1-3 2-3
The concentration of 1, 3-hexanediol, 5-methyl- (C7)	109863-14-1	2-9 6-8		1	1-3 2-3

1, 4-hexanediol (C6)	16432-53-4		1-5 2-5	2		1
							The concentration of 1, 4-hexanediol, 2-methyl- (C7)	Method F	2-9 6-8		1	1-3 2-3
The concentration of 1, 4-hexanediol, 3-methyl- (C7)	66225-36-3	2-9 6-8		1	1-3 2-3
							The concentration of 1, 4-hexanediol, 4-methyl- (C7)	40646-08-0	2-9 6-8		1	1-3 2-3
The concentration of 1, 4-hexanediol, 5-methyl- (C7)	38624-36-1	2-9 6-8		1	1-3 2-3
							1, 5-hexanediol (C6)	928-40-5		1-5 2-5	2		1
The reaction product of 1, 5-hexanediol, 2-methyl- (C7)	Method F	2-9 6-8		1	1-3 2-3
							The reaction product of 1, 5-hexanediol, 3-methyl- (C7)	Method F	2-9 6-8		1	1-3 2-3
The reaction product of 1, 5-hexanediol, 4-methyl- (C7)	66225-37-4	2-9 6-8		1	1-3 2-3
							The reaction product of 1, 5-hexanediol, 5-methyl- (C7)	1462-11-9	2-9 6-8		1	1-3 2-3
1, 6-hexanediol (C6)	629-11-8		1-2	1-2	4
							The concentration of 1, 6-hexanediol, 2-methyl- (C7)	25258-92-8	1-5 2-5			1-2 1
The concentration of 1, 6-hexanediol, 3-methyl- (C7)	4089-71-8	1-5 2-5			1-2 1
							2, 3-hexanediol (C6)	617-30-1	1-5 2-5			1-2 1
2, 4-hexanediol (C6)	19780-90-6		3-8 5-8	3

The reaction mixture of 2, 4-hexanediol, 2-methyl- (C7)	66225-35-2		1-2	1-2
							The reaction mixture of 2, 4-hexanediol, 3-methyl- (C7)	116530-79-1		1-2	1-2
The reaction mixture of 2, 4-hexanediol, 4-methyl- (C7)	38836-25-8		1-2	1-2
							The reaction mixture of 2, 4-hexanediol, 5-methyl- (C7)	54877-00-8		1-2	1-2
2, 5-hexanediol (C6)	2935-44-6		3-8 5-8	3
							The reaction mixture of 2, 5-hexanediol, 2-methyl- (C7)	29044-06-2		1-2	1-2
The reaction mixture of 2, 5-hexanediol, 3-methyl- (C7)	Method H		1-2	1-2
							3, 4-hexanediol (C6)	922-17-8	1-5 2-5			1

(a) The number of alkoxylated groups shown in the above table are all usable, with the usual ranges listed in the first row, while those preferred are shown in bold font, juxtaposed in the second row.

(b) The numbers in this column are those of the polyethoxylated derivatives of (CH)₂CH₂O) average number of radicals.

(c) The numbers in this column are for the (CH) mono-methyl terminated polyethoxylate substituent in each derivative₂CH₂O) average number of bases.

(e) The numbers in this column are those of (CH) in the polypropoxylated derivative₃)CH₂O) average number of radicals.

(f) The numbers in this column are (CH) in the polytetramethyleneoxylated derivatives₂CH₂CH₂CH₂O) average number of radicals.

(g) The numbers in this column are those of (CH) in the multibutoxylated derivatives₂CH₃)CH₂O) average number of radicals.

TABLE VIIIE

Basic substance(a)	Basic substance CAS No.	EO′s	1(Me-En)	PO′s	n-BO′s
								(b)	(c)	(e)	(f)
1, 3-heptanediol (C7)	23433-04-7	1-7 3-6		1	1-2 2
						1, 4-heptanediol (C7)	40646-07-9	1-7 3-6		1	1-2 2
1, 5-heptanediol (C7)	60096-09-5	1-7 3-6		1	1-2 2
						1, 6-heptanediol (C7)	13175-27-4	1-7 3-6		1	1-2 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)	70444-25-6	3-10 7-10	1	1	3
						2, 6-heptanediol (C7)	5969-12-0	3-10 7-10	1	1	3
3, 5-heptanediol (C7)	86632-40-8	3-10 7-10	1	1	3

(a) The number of alkoxylated groups shown in the above table are all usable, with the usual ranges listed in the first row, while those preferred are shown in bold font, juxtaposed in the second row.

(b) The numbers in this column are those of the polyethoxylated derivatives of (CH)₂CH₂O) average number of radicals.

(c) The numbers in this column are for the (CH) mono-methyl terminated polyethoxylate substituent in each derivative₂CH₂O) average number of bases.

(e) The numbers in this column are those of (CH) in the polypropoxylated derivative₃)CH₂O) radicalAverage of (d).

(f) The numbers in this column are (CH) in the polytetramethyleneoxylated derivatives₂CH₂CH₂CH₂O) average number of radicals.

TABLE IX

Aromatic diols

Suitable aromatic diols include: chemical name CAS No. available aromatic diol 1-phenyl-1, 2-ethanediol 93-56-11-phenyl-1, 2-propanediol 1855-09-02-phenyl-1, 2-propanediol 87760-50-73-phenyl-1, 2-propanediol 17131-14-51- (3-methylphenyl) -1, 3-propanediol 51699-43-51- (4-methylphenyl) -1, 3-propanediol 159266-06-52-methyl-1-phenyl-1, 3-propanediol 139068-60-31-phenyl-1, 3-butanediol 118100-60-03-phenyl-1, 3-butanediol 68330-54-11-phenyl-1, 4-butanediol 136173-88-12-phenyl-1, 4-butanediol 95840-73-61-phenyl-2, 3-butanediol 169437-68-7 the preferred aromatic diol 1-phenyl-1, 2-ethanediol 93-56-11-phenyl-1, 2-propanediol 1855-09-02-phenyl-1, 2-propanediol 87760-50-73-phenyl-1, 2-propanediol 17131-14-51- (3-methylphenyl) -1, 3-propanediol 51699-43-51- (4-methylphenyl) -1, 3-propanediol 159266-06-52-methyl-1-phenyl-1, 3-propanediol 139068-60-31-phenyl-1, 3-butanediol 118100-60-03-phenyl-1, 3-butanediol 68330-54-11-phenyl-1, 4-butanediol 136173-88-1, more preferably aromatic diol 1-phenyl-1, 2-propanediol 1855-09-02-phenyl-1, 2-propanediol 87760-50-73-phenyl-1, 2-propanediol 17131-14-51- (3-methylphenyl) -1, 3-propanediol 51699-43-51- (4-methylphenyl) -1, 3-propanediol 159266-06-52-methyl-1-phenyl-1, 3-propanediol 139068-60-33-phenyl-1, 3-butanediol 68330-54-11-phenyl-1, 4-butanediol 136173-88-1 aromatic diol 1-phenyl-1, 3-propanediol 2-phenyl-1, 3-propanediol 1-phenyl-1, 2-butanediol 154902-08-62-phenyl-1, 2-butanediol 157008-55-43-phenyl-1, 2-butanediol 141505-72-84-phenyl-1, 2-butanediol 143615-31-02-phenyl-1, 3-butanediol 103941-94-24-phenyl-1, 3-butanediol 81096-91-52-phenyl-2, 3-butanediol 138432-94-7

X. the congeners or analogs of the main solvents of the above structure, having their total number of hydrogen atoms added by one or more CH₂The radicals are increased but the total number of hydrogen atoms is kept the same by introducing double bonds, so that these analogs are also useful, and they include the following known compounds.

Table X

Examples of unsaturated compounds usable are unsaturated diol 1, 3-propanediol, 2, 2-di-2-propenyl-55038-13-61, 3-propanediol, 2- (1-pentenyl) -138436-18-71, 3-propanediol, 2- (2-methyl-2-propenyl) -2- (2-propenyl) -121887-76-11, 3-propanediol, 2- (3-methyl-1-butenyl) -138436-17-61, 3-propanediol, 2- (4-pentenyl) -73012-46-11, 3-propanediol, 2-ethyl-2- (2-methyl-2-propenyl) -91367-61-21, 3-propanediol, 2-ethyl-2- (2-propenyl) -27606-26-41, 3-propanediol, 2-methyl-2- (3-methyl-3-butenyl) -132130-95-11, 3-butanediol, 2, 2-diallyl-103985-49-51, 3-butanediol, 2- (1-ethyl-1-propenyl) -116103-35-61, 3-butanediol, 2- (2-butenyl) -2-methyl-92207-83-51, 3-butanediol, 2- (3-methyl-2-butenyl) -98955-19-21, 3-butanediol, 2-ethyl-2- (2-propenyl) -122761-93-71, 3-butanediol, 2-methyl-2- (1-methyl-2-propenyl) -141585-58-21, 4-butanediol, 2, 3-bis (1-methylethylidene) -52127-63-61, 4-butanediol, 2- (3-methyl-2-butenyl) -3-methylene-115895-78-82-butene-1, 4-diol, 2- (1, 1-dimethylpropyl) -91154-01-72-butene-1, 4-diol, 2- (1-methylpropyl) -91154-00-62-butene-1, 4-diol, 2-butyl-153943-66-91, 3-pentanediol, 2-vinyl-3-ethyl-104683-37-61, 3-pentanediol, 2-vinyl-4, 4-dimethyl-143447-08-91, 4-pentanediol, 3-methyl-2- (2-propenyl) -139301-86-31, 5-pentanediol, 2- (1-propenyl) -84143-44-21, 5-pentanediol, 2- (2-propenyl) -134757-01-01, 5-pentanediol, 2-ethylene-3-methyl-42178-93-81, 5-pentanediol, 2-propylene-58203-50, 4-pentanediol, 3-ethylene-2, 4-dimethyl-88610-19-94-pentene-1, 3-diol, 2- (1, 1-dimethylethyl) -109788-04-74-pentene-1, 3-diol, 2-ethyl-2, 3-dimethyl-90676-97-41, 4-hexanediol, 4-ethyl-2-methylene-66950-87-61, 5-hexadiene-3, 4-diol, 2, 3, 5-trimethyl-18984-03-71, 5-hexadiene-3, 4-diol, 5-ethyl-3-methyl-18927-12-31, 5-hexanediol, 2- (1-methylvinyl) -96802-18-51, 6-hexanediol, 2-vinyl-66747-31-71-hexene-3, 4-diol, 5, 5-dimethyl-169736-29-21-hexene-3, 4-diol, 5, 5-dimethyl-120191-04-02-hexene-1, 5-diol, 4-vinyl-2, 5-dimethyl-70101-76-73-hexene-1, 6-diol, 2-vinyl-2, 5-dimethyl-112763-52-73-hexene-1, 6-diol, 2-ethyl-84143-45-33-hexene-1, 6-diol, 3, 4-dimethyl-125032-66-84-hexene-2, 3-diol, 2, 5-dimethyl-13295-61-94-hexene-2, 3-diol, 3, 4-dimethyl-135367-17-85-hexene-1, 3-diol, 3- (2-propenyl) -74693-24-65-hexene-2, 3-diol, 2, 3-dimethyl-154386-00-25-hexene-2, 3-diol, 3, 4-dimethyl-135096-13-85-hexene-2, 3-diol, 3, 5-dimethyl-134626-63-45-hexene-2, 4-diol, 3-vinyl-2, 5-dimethyl-155751-24-91, 4-heptanediol, 6-methyl-5-methylene-100590-29-21, 5-heptadiene-3, 4-diol, 2, 3-dimethyl-18927-06-51, 5-heptadiene-3, 4-diol, 2, 5-dimethyl-22607-16-51, 5-heptadiene-3, 4-diol, 3, 5-dimethyl-18938-51-71, 7-heptanediol, 2, 6-bis (methylene) -139618-24-91, 7-heptanediol, 4-methylene-71370-08-61-heptene-3, 5-diol, 2, 4-dimethyl-155932-77-71-heptene-3, 5-diol, 2, 6-dimethyl-132157-35-81-heptene-3, 5-diol, 3-vinyl-5-methyl-61841-10-91-heptene-3, 5-diol, 6, 6-dimethyl-109788-01-42, 4-heptadiene-2, 6-diol, 4, 6-dimethyl-102605-95-82, 5-heptadiene-1, 7-diol, 4, 4-dimethyl-162816-19-52, 6-heptadiene-1, 4-diol, 2, 5, 5-trimethyl-115346-30-02-heptene-1, 4-diol, 5, 6-dimethyl-103867-76-12-heptene-1, 5-diol, 5-ethyl-104683-39-82-heptene-1, 7-diol, 2-methyl-74868-68-13-heptene-1, 5-diol, 4, 6-dimethyl-147028-45-33-heptene-1, 7-diol, 3-methyl-6-methylene-109750-55-23-heptene-2, 5-diol, 2, 4-dimethyl-98955-40-93-heptene-2, 5-diol, 2, 5-dimethyl-24459-23-23-heptene-2, 6-diol, 2, 6-dimethyl-160524-66-33-heptene-2, 6-diol, 4, 6-dimethyl-59502-66-85-heptene-1, 3-diol, 2, 4-dimethyl-123363-69-95-heptene-1, 3-diol, 3, 6-dimethyl-96924-52-65-heptene-1, 4-diol, 2, 6-dimethyl-106777-98-45-heptene-1, 4-diol, 3, 6-dimethyl-106777-99-55-heptene-2, 4-diol, 2, 3-dimethyl-104651-56-16-heptene-1, 3-diol, 2, 2-dimethyl-140192-39-86-heptene-1, 4-diol, 4- (2-propenyl) -1727-87-36-heptene-1, 4-diol, 5, 6-dimethyl-152344-16-66-heptene-1, 5-diol, 2, 4-dimethyl-74231-27-96-heptene-1, 5-diol, 2-ethylidene-6-methyl-91139-73-06-heptene-2, 4-diol, 4- (2-propenyl) -101536-75-86-heptene-2, 4-diol, 5, 5-dimethyl-98753-77-66-heptene-2, 5-diol, 4, 6-dimethyl-134876-94-16-heptene-2, 5-diol, 5-vinyl-4-methyl-65757-31-51, 3-octanediol, 2-methylene-108086-78-81, 6-octadiene-3, 5-diol, 2, 6-dimethyl-91140-06-61, 6-octadiene-3, 5-diol, 3, 7-dimethyl-75654-19-21, 7-octadiene-3, 6-diol, 2, 6-dimethyl-51276-33-61, 7-octadiene-3, 6-diol, 2, 7-dimethyl-26947-10-41, 7-octadiene-3, 6-diol, 3, 6-dimethyl-31354-73-11-octene-3, 6-diol, 3-vinyl-65757-34-82, 4, 6-octatriene-1, 8-diol, 2, 7-dimethyl-162648-63-72, 4-octadiene-1, 7-diol, 3, 7-dimethyl-136054-24-52, 5-octadiene-1, 7-diol, 2, 6-dimethyl-91140-07-72, 5-octadiene-1, 7-diol, 3, 7-dimethyl-117935-59-82, 6-octadiene-1, 4-diol, 3, 7-dimethyl- (Rosiridol) 101391-01-92, 6-octadiene-1, 8-diol, 2-methyl-149112-02-72, 7-octadiene-1, 4-diol, 3, 7-dimethyl-91140-08-82, 7-octadiene-1, 5-diol, 2, 6-dimethyl-91140-09-92, 7-octadiene-1, 6-diol, 2, 6-dimethyl- (8-hydroxylinalool) 103619-06-32, 7-octadiene-1, 6-diol, 2, 7-dimethyl-60250-14-82-octene-1, 4-diol 40735-15-72-octene-1, 7-diol 73842-95-22-octene-1, 7-diol, 2-methyl-6-methylene-91140-16-83, 5-octadiene-1, 7-diol, 3, 7-dimethyl-62875-09-63, 5-octadiene-2, 7-diol, 2, 7-dimethyl-7177-18-63, 5-octadiene, 4-methylene-143233-15-23, 7-octadiene-1, 6-diol, 2, 6-dimethyl-127446-29-13, 7-octadiene-2, 5-diol, 2, 7-dimethyl-171436-39-83, 7-octadiene-2, 6-diol, 2, 6-dimethyl-150283-67-33-octene-1, 5-diol, 4-methyl-147028-43-13-octene-1, 5-diol, 5-methyl-19764-77-34, 6-octadiene-1, 3-diol, 2, 2-dimethyl-39824-01-64, 7-octadiene-2, 3-diol, 2, 6-dimethyl-51117-38-54, 7-octadiene-2, 6-diol, 2, 6-dimethyl-59076-71-04-octene-1, 6-diol, 7-methyl-84538-24-94-octene-1, 8-diol, 2, 7-bis (methylene) -109750-56-34-octene-1, 8-diol, 2-methylene-109750-58-55, 7-octadiene-1, 4-diol, 2, 7-dimethyl-105676-78-65, 7-octadiene-1, 4-diol, 7-methyl-105676-80-05-octene-1, 3-diol 130272-38-76-octene-1, 3-diol, 7-methyl-110971-19-26-octene-1, 4-diol, 7-methyl-152715-87-octene-1, 5-diol 145623-79-66-octene-1, 5-diol, 7-methyl-116214-61-06-octene-3, 5-diol, 2-methyl-65534-66-96-octene-3, 5-diol, 4-methyl-156414-25-47-octene-1, 3-diol, 2-methyl-155295-38-87-octene-1, 3-diol, 4-methyl-142459-25-47-octene-1, 3-diol, 7-methyl-132130-96-27-octene-1, 5-diol 7310-51-27-octene-1, 6-diol 159099-43-17-octene-1, 6-diol, 5-methyl-144880-56-87-octene-2, 4-diol, 2-methyl-6-methylene-72446-81-27-octene-2, 5-diol, 7-methyl-152344-12-27-octene-3, 5-diol, 2-methyl-98753-85-61-nonene-3, 5-diol 119554-56-21-nonene-3, 7-diol 23866-97-93-nonene-2, 5-diol 165746-84-94, 6-nonadiene-1, 3-diol, 8-methyl-124099-52-14-nonene-2, 8-diol 154600-80-36, 8-nonadiene-1, 5-diol 108586-03-47-nonene-2, 4-diol 30625-41-38-nonene-2, 4-diol 119785-59-08-nonene-2, 5-diol 132381-58-91, 9-decadiene-3, 8-diol 103984-04-91, 9-decadiene-4, 6-diol 138835-67-3 preferred unsaturated diol 1, 3-butanediol, 2, 2-diallyl-103985-49-51, 3-butanediol, 2- (1-ethyl-1-propenyl) -116103-35-61, 3-butanediol, 2- (2-butenyl) -2-methyl-92207-83-51, 3-butanediol, 2- (3-methyl-2-butenyl) -98955-19-21, 3-butanediol, 2-ethyl-2- (2-propenyl) -122761-93-71, 3-butanediol, 2-methyl-2- (1-methyl-2-propenyl) -141585-58-21, 4-butanediol, 2, 3-bis (1-methylethylidene) -52127-63-61, 3-pentanediol, 2-vinyl-3-ethyl-104683-37-61, 3-pentanediol, 2-vinyl-4, 4-dimethyl-143447-08-91, 4-pentanediol, 3-methyl-2- (2-propenyl) -139301-86-34-pentene-1, 3-diol, 2- (1, 1-dimethylethyl) -109788-04-74-pentene-1, 3-diol, 2-ethyl-2, 3-dimethyl-90676-97-41, 4-hexanediol, 4-ethyl-2-methylene-66950-87-61, 5-hexadiene-3, 4-diol, 2, 3, 5-trimethyl-18984-03-71, 5-hexanediol, 2- (1-methylvinyl) -96802-18-52-hexene-1, 5-diol, 4-vinyl-2, 5-dimethyl-70101-76-71, 4-heptadiene, 6-methyl-5-methylene-100590-29-22, 4-heptadiene-2, 6-diol, 4, 6-dimethyl-102605-95-82, 6-heptadiene-1, 4-diol, 2, 5, 5-trimethyl-115346-30-02-heptene-1, 4-diol, 5, 6-dimethyl-103867-76-13-heptene-1, 5-diol, 4, 6-dimethyl-147028-45-35-heptene-1, 3-diol, 2, 4-dimethyl-123363-69-95-heptene-1, 3-diol, 3, 6-dimethyl-96924-52-65-heptene-1, 4-diol, 2, 6-dimethyl-106777-98-45-heptene-1, 4-diol, 3, 6-dimethyl-106777-99-56-heptene-1, 3-diol, 2, 2-dimethyl-140192-39-86-heptene-1, 4-diol, 5, 6-dimethyl-152344-16-66-heptene-1, 5-diol, 2, 4-dimethyl-74231-27-96-heptene-1, 5-diol, 2-ethylene-6-methyl-91139-73-06-heptene-2, 4-diol, 4- (2-propenyl) -101536-75-81-octene-3, 6-diol, 3-vinyl-65757-34-82, 4, 6-octatriene-1, 8-diol, 2, 7-dimethyl-162648-63-72, 5-octadiene-1, 7-diol, 2, 6-dimethyl-91140-07-72, 5-octadiene-1, 7-diol, 3, 7-dimethyl-117935-59-82, 6-octadiene-1, 4-diol, 3, 7-dimethyl- (Rosiridol) 101391-01-92, 6-octadiene-1, 8-diol, 2-methyl-149112-02-72, 7-octadiene-1, 4-diol, 3, 7-dimethyl-91140-08-82, 7-octadiene-1, 5-diol, 2, 6-dimethyl-91140-09-92, 7-octadiene-1, 6-diol, 2, 6-dimethyl- (8-hydroxylinalool) 103619-06-32, 7-octadiene-1, 6-diol, 2, 7-dimethyl-60250-14-82-octene-1, 7-diol, 2-methyl-6-methylene-91140-16-83, 5-octadiene-2, 7-diol, 2, 7-dimethyl-7177-18-63, 5-octanediol, 4-methylene-143233-15-23, 7-octadiene-1, 6-diol, 2, 6-dimethyl-127446-29-14-octene-1, 8-diol, 2-methylene-109750-58-56-octene-3, 5-diol, 2-methyl-65534-66-96-octene-3, 5-diol, 4-methyl-156414-25-47-octene-2, 4-diol, 2-methyl-6-methylene-72446-81-27-octene-2, 5-diol, 7-methyl-152344-12-27-octene-3, 5-diol, 2-methyl-98753-85-61-nonene-3, 5-diol 119554-56-21-nonene-3, 7-diol 23866-97-93-nonene-2, 5-diol 165746-84-94-nonene-2, 8-diol 154600-80-36, 8-nonadiene-1, 5-diol 108586-03-47-nonene-2, 4-diol 30625-41-38-nonene-2, 4-diol 119785-59-08-nonene-2, 5-diol 132381-58-91, 9-decadiene-3, 8-diol 103984-04-91, 9-decadiene-4, 6-diol 138835-67-3; mixtures thereof.

None of C_1-2The mono-alcohol is capable of producing the clear and concentrated fabric softener compositions referred to in the text of the present invention. Only one kind of C₃The monohydric alcohol, n-propanol, has the acceptable property of producing a clear product and remaining clear up to a temperature of about 20 c, or of recovering the product when it is warmed to room temperature. At C₄Of the unit alcohols, only 2-butanol and 2-methyl-2-propanol have good properties, but the boiling point of 2-methyl-2-propanol is too low. As mentioned above and below, there is no C other than its unsaturated mono-alcohol_5-6The monoalcohol can produce clear product.

It has been found that some of the principal solvents in the formula having two hydroxyl groups are suitable for formulating the liquid concentrated and clear fabric softener compositions of the present invention. The suitability of each of the principal solvents has been found to be surprisingly selective, depending on the number of carbon atoms, the isomeric configuration of the molecules having the same number of carbon atoms, the degree of unsaturation, and the like. A primary solvent having the same solubility properties as the primary solvent described above, and having at least some asymmetry, would be of equal benefit. Suitable principal solvents have been found to have a Clog P value of from about 0.15 to about 0.64, preferably from about 0.25 to about 0.62, more preferably from about 0.40 to about 0.60.

For example, for the general formula HO-CH₂-CHOH-(CH₂)_n-H, 1, 2-alkanediol principal solvents wherein n is from 1 to 8, only 1, 2-hexanediol (where n is 4), having a Clog P value of about 0.53, which is within an effective range of Clog P values of about 0.15 to 0.64, is a good principal solvent, and within the scope of the present invention, while others such as 1, 2-propanediol, 1, 2-butanediol, 1, 2-pentanediol, 1, 2-octanediol, 1, 2-decanediol, which have Clog P values outside the effective range of 0.15 to 0.64, are not good principal solvents. Furthermore, 1, 2-hexanediol is a good primary solvent for the hexanediol isomers, while many other isomers, such as 1, 3-hexanediol, 1, 4-hexanediol, 1, 5-hexanediol, 1, 6-hexanediol, 2, 4-hexanediol and 2, 5-hexanediol, have Clog P values outside the effective range of 0.15 to 0.64 and are not good primary solvents. These are illustrated in the examples and comparative examples I-A and I-B (see below).

None of C₃-C₅Diols are capable of producing clear and concentrated compositions as described in the context of the present invention.

Although there are many possibilities of C₆The diol isomers, but only those listed above, are suitable for making clear products, only: 1, 2-butanediol, 2, 3-dimethyl-; 1, 2-butanediol, 3, 3-dimethyl-; 2, 3-pentanediol, 2-methyl-; 2, 3-pentanediol, 3-methyl-; 2, 3-pentanediol, 4-methyl-; 2, 3-hexanediol; 3, 4-hexanediol; 1, 2-butanediol, 2-ethyl-; 1, 2-pentanediol, 2-methyl-; 1, 2-pentanediol, 3 methyl-; 1, 2-pentanediol, 4-methyl-; and 1, 2-hexanediol are preferred, with the most preferred among them being: 1, 2-butanediol, 2-ethyl-; 1, 2-pentanediol, 2-methyl-; 1, 2-pentanediol, 3-methyl-; 1, 2-pentanediol, 4-methyl-; and 1, 2-hexanediol.

C₇The diol isomers are more numerous, but only the listed ones give clear products, and preferably: 1, 3-butanediol, 2-butyl-; 1, 4-butanediol, 2-propyl-; 1, 5-pentanediol, 2-ethyl-; 2, 3-pentanediol, 2, 3-dimethyl-; 2, 3-pentanediol, 2, 4-dimethyl-; 2, 3-pentanediol, 4, 4-dimethyl-; 3, 4-pentanediol, 2, 3-dimethyl-; 1, 6-hexanediol, 2-methyl-; 1, 6-hexanediol, 3-methyl-; 1, 3-heptanediol; 1, 4-heptanediol; 1, 5-heptanediol, 1, 6-heptanediol; most preferred among these are: 2, 3-pentanediol; 2, 3-dimethyl-; 2, 3-pentanediol, 2, 4-dimethyl-; 2, 3-pentanediol, 3, 4-dimethyl-; 2, 3-pentanediol, 4, 4-dimethyl; and 3, 4-pentanediol, 2, 3-dimethyl-.

Likewise, C₈The diol isomers are even more numerous, but only the listed ones give clear products, and preferably: 1, 3-propanediol, 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-butanediol, 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-propyl-; 1, 3-butanediol, 2-methyl-2-isopropyl-; 1, 3-butanediol, 3-methyl-2-propyl-; 1, 4-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, 3-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, 4-pentanediol, 2, 2, 3-triethyl-; 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-; 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-methyl-; 1, 4-pentanediol, 2-ethyl-3-methyl-; 1, 4-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-; 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, 4, 4-dimethyl-; 1, 3-hexanediol, 4, 5-dimethyl-; 1, 4-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, 5-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-; 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, 6-heptanediol, 2-methyl-; 1, 6-heptanediol, 3-methyl-; 1, 6-heptanediol, 4-methyl-; 1, 6-heptanediol, 5-methyl-; 1, 6-heptanediol, 6-methyl-; 2, 4-heptanediol, 2-methyl-; 2, 4-heptanediol, 3-methyl-; 2, 4-heptanediol, 4-methyl-; 2, 4-heptanediol, 5-methyl-; 2, 4-heptanediol, 6-methyl-; 2, 5-heptanediol, 2-methyl-; 2, 5-heptanediol, 3-methyl-; 2, 5-heptanediol, 4-methyl-; 2, 5-heptanediol, 5-methyl-; 2, 5-heptanediol, 6-methyl-; 2, 6-heptanediol, 2-methyl-; 2, 6-heptanediol, 3-methyl-; 2, 6-heptanediol, 4-methyl-; 3, 4-heptanediol, 3-methyl-; 3, 5-heptanediol, 2-methyl-; 3, 5-heptanediol, 4-methyl-; 2, 4-octanediol; 2, 5-octanediol; 2, 6-octanediol; 2, 7-octanediol; 3, 5-octanediol; and/or 3, 6-octanediol, among which the following are most preferred: 1, 3-propanediol, 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-butanediol, 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, 4-butanediol, 2, 2-diethyl-; 1, 4-butanediol, 2-ethyl-2, 3-dimethyl-; 1, 4-butanediol, 2-ethanediol-yl-3, 3-dimethyl-; 1, 4-butanediol, 2- (1, 1-dimethylethyl) -; 1, 3-pentanediol, 2, 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, 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-methyl-; 1, 4-pentanediol, 2-ethyl-3-methyl-; 1, 4-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-; 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, 4, 4-dimethyl-; 1, 3-hexanediol, 4, 5-dimethyl-; 1, 4-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, 5-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-; 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-a radical-; 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, 6-heptanediol, 2-methyl-; 1, 6-heptanediol, 3-methyl-; 1, 6-heptanediol, 4-methyl-; 1, 6-heptanediol, 5-methyl-; 1, 6-heptanediolAlcohol, 6-methyl-; 2, 4-heptanediol, 2-methyl-; 2, 4-heptanediol, 3-methyl-; 2, 4-heptanediol, 4-methyl-; 2, 4-heptanediol, 5-methyl-; 2, 4-heptanediol, 6-methyl-; 2, 5-heptanediol, 2-methyl-; 2, 5-heptanediol, 3-methyl-; 2, 5-heptanediol, 4-methyl-; 2, 5-heptanediol, 5-methyl-; 2, 5-heptanediol, 6-methyl-; 2, 6-heptanediol, 2-methyl-; 2, 6-heptanediol, 3-methyl-; 2, 6-heptanediol, 4-methyl-; 3, 4-heptanediol, 3-methyl-; 3, 5-heptanediol, 2-methyl-; 3, 5-heptanediol, 4-methyl-; 2, 4-octanediol; 2, 5-octanediol; 2, 6-octanediol; 2, 7-octanediol; 3, 5-octanediol; and/or 3, 6-octanediol.

Preferred eight carbon atom 1, 3-diols can be prepared as follows: condensing a mixture of butyraldehyde, isobutyraldehyde and/or methyl ethyl ketone (2-butanone) in the presence of a strong base catalyst, provided that at least two are present in the reaction mixture, and subsequently converting them by hydrogenation to a mixture of octacarbon-1, 3-diols, i.e., a mixture consisting essentially of 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, the 2, 2, 4-trimethyl-1, 3-pentanediol content being less than half of any of the mixtures, other minor isomers may also be present, these isomers being obtained by condensation of the methylene group of 2-butanone (when it is present) instead of the methyl group.

TABLE IISome less preferred C listed under-IV_6-8The formulability and other properties of the diols, such as odor, flowability, melting point depression, etc., can be improved by polyalkoxylation. In addition, some C's which have been alkoxylated_3-5Diols are preferred. C above_3-8Preferred alkoxylated derivatives of diols [ in the following disclosure, "EO" means polyethoxylate, "E_n"means (CH)₂CH₂O)_nH; Me-En methyl-terminated polyethoxylates- (CH)₂CH₂O)_nCH₃(ii) a "2 (Me-En)" means that two Me-En groups are required; "PO" refers to polypropoxide, - (CH)₃)CH₂O)_nH; "BO" refers to the multiple butoxy group (CH)₂CH₃)CH₂O)_nH; and "n-BO" refers to poly (n-butoxy) (CH)₂CH₂CH₂CH₂O)_nH]The method comprises the following steps: 1, 2-propanediol (C3)2 (Me-E)_3-4) (ii) a1, 2-propanediol (C3) PO₄(ii) a1, 2-propanediol, 2-methyl- (C4) (Me-E)_8-10) (ii) a1, 2-propanediol, 2-methyl- (C4)2 (Me-E)₁) (ii) a1, 2-propanediol, 2-methyl- (C4) PO₃(ii) a1, 3-propanediol (C3)2 (Me-E)₈) (ii) a1, 3-propanediol (C3) PO₆；1，3Propylene glycol, 2, 2-diethyl (C7) E_4-7(ii) a1, 3-propanediol, 2, 2-diethyl- (C7) PO₁(ii) a1, 3-propanediol, 2, 2-diethyl (C7) n-BO₂(ii) a1, 3-propanediol, 2, 2-dimethyl- (C5)2 (MeE)_1-2) (ii) a1, 3-propanediol, 2, 2-dimethyl- (C5) PO₄(ii) a1, 3-propanediol, 2- (1-methylpropyl) (C7) E_4-7(ii) a1, 3-propanediol, 2- (1-methylpropyl) - (C7) PO₁(ii) a1, 3-propanediol, 2- (1-methylpropyl) - (C7) n-BO₂(ii) a1, 3-propanediol, 2- (2-methylpropyl) - (C7) E_4-7(ii) a1, 3-propanediol, 2- (2-methylpropyl) - (C7) PO₁(ii) a1, 3-propanediol, 2- (2-methylpropyl) - (C7) n-BO₂(ii) a1, 3-propanediol, 2-ethyl (C5) (MeE)_9-10) (ii) a1, 3-propanediol, 2-ethyl- (C5)2 (MeE)₁) (ii) a1, 3-propanediol, 2-ethyl (C5) PO₃(ii) a1, 3-propanediol, 2-ethyl-2-methyl- (C6) (MeE)_3-6) (ii) a The concentration of 1, 3-propanediol is,2-Ethyl-2-methyl- (C6) PO₂(ii) a1, 3-propanediol, 2-ethyl-2-methyl- (C6) BO₁(ii) a1, 3-propanediol, 2-isopropyl- (C6) (MeE)_3-6) (ii) a1, 3-propanediol, 2-isopropanol- (C6) PO₂(ii) a1, 3-propanediol, 2-isopropyl- (C6) BO₁(ii) a1, 3-propanediol, 2-methyl- (C4)2 (MeE)_4-5) (ii) a1, 3-propanediol, 2-methyl- (C4) PO₅(ii) a1, 3-propanediol, 2-methyl- (C4) BO₂(ii) a1, 3-propanediol, 2-methyl-2-isopropyl- (C7) E_6-9(ii) a1, 3-propanediol, 2-methyl-2-isopropyl- (C7) PO₁(ii) a1, 3-propanediol, 2-methyl-2-isopropyl- (C7) n-BO_2-3(ii) a1, 3-propanediol, 2-methyl-2-propyl- (C7) E_4-7(ii) a1, 3-propanediol, 2-methyl-2-propyl- (C7) PO₁(ii) a1, 3-propanediol, 2-methyl-2-propyl- (C7) n-BO₂(ii) a1, 3-propanediol, 2-propyl- (C6) (MeE)_1-4) (ii) a1, 3-propanediol, 2-propyl- (C6) PO₂(ii) a2, 1, 2-butanediol, (C4) (MeE)_6-8) (ii) a1, 2-butanediol, (C4) PO_2-3(ii) a1, 2-butanediol, (C4) BO₁(ii) a1, 2-butanediol, 2, 3-dimethyl- (C6) E_2-5(ii) a1, 2-butanediol, 2, 3-dimethyl- (C6) n-BO₁(ii) a1, 2-butanediol, 2-Ethyl- (C6) E_1-3(ii) a1, 2-butanediol, 2-Ethyl- (C6) n-BO₁(ii) a1, 2-butanediol, 2-methyl- (C5) (MeE)_1-2) (ii) a1, 2-butanediol, 2-methyl- (C5) PO₁(ii) a1, 2-butanediol, 3, 3-dimethyl- (C6) E_2-5(ii) a1, 2-butanediol, 3, 3-dimethyl- (C6) n-BO₁(ii) a1, 2-butanediol, 3-methyl- (C5) (MeE)_1-2) (ii) a1, 2-butanediol, 3-methyl- (C5)PO₁(ii) a1, 3-butanediol, (C4)2 (MeE)_5-6) (ii) a1, 3-butanediol (C4) BO₂(ii) a1, 3-butanediol, 2, 2, 3-trimethyl- (C7) (MeE)_1-3) (ii) a1, 3-butanediol, 2, 2, 3-trimethyl- (C7) PO₂(ii) a1, 3-butanediol, 2, 2-dimethyl- (C6) (MeE)_6-8) (ii) a1, 3-butanediol, 2, 2-dimethyl- (C6) PO₃(ii) a1, 3-butanediol, 2, 3-dimethyl- (C6) (MeE)_6-8) (ii) a1, 3-butanediol, 2, 3-dimethyl- (C6) PO₃(ii) a1, 3-butanediol, 2-Ethyl- (C6) (MeE)_4-6) (ii) a1, 3-butanediol, 2-ethanediolRadical- (C6) PO_2-3(ii) a1, 3-butanediol, 2-Ethyl- (C6) BO₁(ii) a1, 3-butanediol, 2-ethyl-2-methyl- (C7) (MeE)₁) (ii) a1, 3-butanediol, 2-ethyl-2-methyl- (C7) PO₁(ii) a1, 3-butanediol, 2-ethyl-2-methyl- (C7) n-BO₃(ii) a1, 3-butanediol, 2-ethyl-3-methyl- (C7) (MeE)₁) (ii) a1, 3-butanediol, 2-ethyl-3-methyl- (C7) PO₁(ii) a1, 3-butanediol, 2-ethyl-3-methyl- (C7) n-BO₃(ii) a1, 3-butanediol, 2-isopropyl- (C7) (MeE)₁) (ii) a1, 3-butanediol, 2-isopropyl- (C7) PO₁(ii) a1, 3-butanediol, 2-isopropyl- (C7) n-BO₃(ii) a1, 3-butanediol, 2-methyl- (C5)2 (MeE)_2-3) (ii) a1, 3-butanediol, 2-methyl- (C5) PO₄(ii) a1, 3-butanediol, 2-propyl- (C7) E_6-8(ii) a1, 3-butanediol, 2-propyl- (C7) PO₁(ii) a1, 3-butanediol, 2-propyl- (C7) n-BO_2-3(ii) a1, 3-butanediol, 3-methyl- (C5)2 (MeE)_2-3) (ii) a1, 3-butanediol, 3-methyl- (C5) PO₄(ii) a1, 4-butanediol, (C4)2 (MeE)_3-4) (ii) a1, 4-butanediol, (C4) PO_4-5(ii) a1, 4-butanediol, 2, 2, 3-trimethyl- (C7) E_6-9(ii) a1, 4-butanediol, 2, 2, 3-trimethyl- (C7) PO₁(ii) a1, 4-butanediol, 2, 2, 3-trimethyl- (C7) n-BO_2-3(ii) a1, 4-butanediol, 2, 2-dimethyl- (C6) (MeE)_3-6) (ii) a1, 4-butanediol, 2, 2-dimethyl- (C6) PO₂(ii) a1, 4-butanediol, 2, 2-dimethyl (C6) BO₁(ii) a1, 4-butanediol, 2, 3-dimethyl- (C6) (MeE)_3-6) (ii) a1, 4-butanediol; 2, 3-dimethyl- (C6) PO₂(ii) a1, 4-butanediol, 2, 3-dimethyl- (C6) BO₁(ii) a1, 4-butanediol, 2-Ethyl- (C6) (MeE)_1-4) (ii) a1, 4-butanediol, 2-Ethyl- (C6) PO₂(ii) a1, 4-butanediol, 2-ethyl-2-methyl- (C7) E_4-7(ii) a1, 4-butanediol, 2-ethyl-2-methyl- (C7) PO₁(ii) a1, 4-butanediol, 2-ethyl-2-methyl- (C7) n-BO₂(ii) a1, 4-butanediol, 2-ethyl-3-methyl- (C7) E_4-7(ii) a1, 4-butanediol, 2-ethyl-3-methyl- (C7) PO₁；1, 4-butanediol, 2-ethyl-3-methyl- (C7) n-BO₂(ii) a1, 4-butanediol, 2-isopropyl- (C)7)E_4-7(ii) a1, 4-butanediol, 2-isopropyl (C7) PO₁(ii) a1, 4-butanediol, 2-isopropyl- (C7) n-BO₂(ii) a1, 4-butanediol, 2-methyl- (C5) (MeE)_9-10) (ii) a1, 4-butanediol, 2-methyl- (C5)2 (MeE)₁) (ii) a1, 4-butanediol, 2-methyl- (C5) PO₃(ii) a1, 4-butanediol, 2-propyl- (C7) E_2-5(ii) a1, 4-butanediol, 2-propyl- (C7) n-BO₁(ii) a1, 4-butanediol, 3-ethyl-1-methyl- (C7) E_6-8(ii) a1, 4-butanediol, 3-ethyl-1-methyl- (C7) PO₁(ii) a1, 4-butanediol, 3-ethyl-1-methyl (C7) n-BO_2-3(ii) a2, 3-butanediol (C4) (MeE)_9-10) (ii) a2, 3-butanediol (C4)2 (MeE)₁) (ii) a2, 3-butanediol (C4) PO_3-4(ii) a2, 3-butanediol, 2, 3-dimethyl- (C6) E_7-9(ii) a2, 3-butanediol, 2, 3-dimethyl- (C6) PO₁(ii) a2, 3-butanediol, 2, 3-dimethyl- (C6) BO_2-3(ii) a2, 3-butanediol, 2-methyl- (C5) (MeE)_2-5) (ii) a2, 3-butanediol, 2-methyl- (C5) PO₂(ii) a2, 3-butanediol, 2-methyl- (C5) BO₁；

3, 2-Pentanediol, (C5) E_7-10(ii) a1, 2-pentanediol, (C5) PO₁(ii) a1, 2-pentanediol, (C5) n-BO₃(ii) a1, 2-pentanediol, 2-methyl (C6) E_1-3(ii) a1, 2-pentanediol, 2-methyl (C6) n-BO₁(ii) a1, 2-pentanediol, 3-methyl (C6) E_1-3(ii) a1, 2-pentanediol, 3-methyl- (C6) n-BO₁(ii) a1, 2-pentanediol, 4-methyl (C6) E_1-3(ii) a1, 2-pentanediol, 4-methyl- (C6) n-BO₁(ii) a1, 3-pentanediol, (C5)2 (Me-E)_1-2) (ii) a1, 3-pentanediol, (C5) PO_3-4(ii) a1, 3-pentanediol, 2, 2-dimethyl- (C7) (Me-E)₁) (ii) a1, 3-pentanediol, 2, 2-dimethyl- (C7) PO₁(ii) a1, 3-pentanediol, 2, 2-dimethyl- (C7) n-BO₃(ii) a1, 3-pentanediol, 2, 3-dimethyl- (C7) (Me-E)₁) (ii) a1, 3-pentanediol, 2, 3-dimethyl- (C7) PO₁(ii) a1, 3-pentanediol, 2, 3-dimethyl (C7) n-BO₃(ii) a1, 3-pentanediol, 2, 4-dimethyl- (C7) (Me-E)₁) (ii) a1, 3-pentanediol, 2, 4-dimethyl- (C7) PO₁(ii) a1, 3-pentanediol, 2, 4-dimethyl- (C7) n-BO₃(ii) a1, 3-pentanediAlcohol, 2-ethyl- (C7) E_6-8(ii) a1, 3-pentanediol, 2-ethyl- (C7) PO₁(ii) a1, 3-pentanediol, 2-ethyl- (C7) n-BO_2-3(ii) a1, 3-pentanediol, 2-methyl- (C6)2 (Me-E)_4-6) (ii) a1, 3-pentanediol, 2-methyl- (C6) PO_2-3(ii) a1, 3-pentanediol, 3, 4-dimethyl- (C7) (Me-E)₁) (ii) a1, 3-pentanediol, 3, 4-dimethyl- (C7) PO₁；1，3-pentanediol, 3, 4-dimethyl- (C7) n-BO₃(ii) a1, 3-pentanediol, 3-methyl- (C6)2 (Me-E)_4-6) (ii) a1, 3-pentanediol, 3-methyl- (C6) PO_2-3(ii) a1, 3-pentanediol, 4, 4-dimethyl- (C7) (Me-E)₁) (ii) a1, 3-pentanediol, 4, 4-dimethyl- (C7) PO₁(ii) a1, 3-pentanediol, 4, 4-dimethyl- (C7) n-BO₃(ii) a1, 3-pentanediol, 4-methyl- (C6)2 (Me-E)_4-6) (ii) a1, 3-pentanediol, 4-methyl- (C6) PO_2-3(ii) a1, 4-pentanediol, (C5)2 (Me-E)_1-2) (ii) a1, 4-pentanediol, (C5) PO_3-4(ii) a1, 4-pentanediol, 2, 2-dimethyl- (C7) (Me-E)₁) (ii) a1, 4-pentanediol, 2, 2-dimethyl- (C7) PO₁(ii) a1, 4-pentanediol, 2, 2-dimethyl- (C7) n-BO₃(ii) a1, 4-pentanediol, 2, 3-dimethyl- (C7) (Me-E)₁) (ii) a1, 4-pentanediol, 2, 3-dimethyl- (C7) PO₁(ii) a1, 4-pentanediol, 2, 3-dimethyl- (C7) n-BO₃(ii) a1, 4-Pentanediol, 2, 4-dimethyl- (C7) (Me-E)₁) (ii) a1, 4-pentanediol, 2, 4-dimethyl- (C7) PO₁(ii) a1, 4-pentanediol, 2, 4-dimethyl- (C7) n-BO₃(ii) a1, 4-Pentanediol, 2-methyl- (C6) (Me-E)_4-6) (ii) a1, 4-Pentanediol, 2-methyl- (C6) PO_2-3(ii) a1, 4-pentanediol, 3, 3-dimethyl- (C7) (Me-E)₁) (ii) a1, 4-pentanediol, 3, 3-dimethyl- (C7) PO₁(ii) a1, 4-pentanediol, 3, 3-dimethyl- (C7) n-BO₃(ii) a1, 4-pentanediol, 3, 4-dimethyl- (C7) (Me-E)₁) (ii) a1, 4-pentanediol, 3, 4-dimethyl- (C7) PO₁(ii) a1, 4-pentanediol, 3, 4-dimethyl- (C7) n-BO₃(ii) a1, 4-pentanediol, 3-methyl- (C6)2 (Me-E)_4-6) (ii) a1, 4-Pentanediol, 3-methyl- (C6) PO_2-3(ii) a1, 4-pentanediol; 4-methyl (C6)2 (Me-E)_4-6) (ii) a1, 4-pentanediol, 4-methyl-(C6)PO_2-3(ii) a1, 5-pentanediol, (C5) (Me-E)_8-10) (ii) a1, 5-pentanediol, (C5)2 (Me-E)₁) (ii) a1, 5-pentanediol, (C5) PO₃(ii) a1, 5-pentanediol, 2, 2-dimethyl- (C7) E_4-7(ii) a1, 5-pentanediol, 2, 2-dimethyl- (C7) PO₁(ii) a1, 5-pentanediol, 2, 2-dimethyl- (C7) n-BO₂(ii) a1, 5-pentanediol, 2, 3-dimethyl- (C7) E_4-7(ii) a1, 5-pentanediol, 2, 3-dimethyl- (C7) PO₁(ii) a1, 5-pentanediol, 2, 3-dimethyl- (C7) n-BO₂(ii) a1, 5-pentanediol, 2, 4-dimethyl- (C7) E_4-7(ii) a1, 5-pentanediol, 2, 4-dimethyl- (C7) PO₁(ii) a1, 5-pentanediol, 2, 4-dimethyl- (C7) n-BO₂(ii) a1, 5-pentanediol, 2-ethyl- (C7) E_2-5(ii) a1, 5-pentanediol, 2-ethyl- (C7) n-BO₁(ii) a1, 5-Pentanediol, 2-methyl- (C6) (Me-E)_1-4) (ii) a1, 5-pentanediol, 2-methyl- (C6)PO₂(ii) a1, 5-pentanediol, 3, 3-dimethyl- (C7) E_4-7(ii) a1, 5-pentanediol, 3, 3-dimethyl- (C7) PO₁(ii) a1, 5-pentanediol, 3, 3-dimethyl- (C7) n-BO₂(ii) a1, 5-Pentanediol, 3-methyl- (C6) (Me-E)_1-4) (ii) a1, 5-Pentanediol, 3-methyl- (C6) PO₂(ii) a2, 3-pentanediol, (C5) (Me-E)_1-3) (ii) a2, 3-pentanediol, (C5) PO₂(ii) a2, 3-pentanediol, 2-methyl- (C6) E_4-7(ii) a2, 3-pentanediol, 2-methyl- (C6) PO₁(ii) a2, 3-pentanediol, 2-methyl (C6) n-BO₂(ii) a2, 3-pentanediol, 3-methyl- (C6) E_4-7(ii) a2, 3-pentanediol, 3-methyl- (C6) PO₁(ii) a2, 3-pentanediol, 3-methyl- (C6) n-BO₂(ii) a2, 3-pentanediol, 4-methyl- (C6) E_4-7(ii) a2, 3-Pentanediol, 4-methyl- (C6) PO₁(ii) a2, 3-pentanediol, 4-methyl- (C6) n-BO₂(ii) a2, 4-Pentanediol (C5)2 (Me-E)_2-4) (ii) a2, 4-Pentanediol- (C5) PO₄(ii) a2, 4-Pentanediol, 2, 3-dimethyl- (C7) (Me-E)_2-4) (ii) a2, 4-Pentanediol, 2, 3-dimethyl- (C7) PO₂(ii) a2, 4-Pentanediol, 2, 4-dimethyl- (C7) (Me-E)_2-4) (ii) a2, 4-Pentanediol, 2, 4-dimethyl- (C7) PO₂(ii) a2, 4-Pentanediol, 2-methyl- (C7) (Me-E)_8-10)；2，4-Pentanediol, 2, 4-dimethyl- (C7) PO₃(ii) a2, 4-pentanediol, 3, 3-dimethyl- (C7) (Me-E)_2-4) (ii) a2, 4-Pentanediol, 3, 3-dimethyl- (C7) PO₂(ii) a2, 4-Pentanediol, 3-methyl- (C6) (Me-E)_8-10) (ii) a2, 4-Pentanediol, 3-methyl- (C6) PO₃；

1, 3-hexanediol, (C6) (Me-E)_2-5) (ii) a1, 3-hexanediol, (C6) PO₂(ii) a1, 3-hexanediol, (C6) BO₁(ii) a1, 3-hexanediol, 2-methyl- (C7) E_6-8(ii) a1, 3-hexanediol, 2-methyl- (C7) PO₁(ii) a1, 3-hexanediol, 2 methyl- (C7) n-BO_2-3(ii) a1, 3-hexanediol, 3-methyl- (C7) E_6-8(ii) a1, 3-hexanediol, 3-methyl- (C7) PO₁(ii) a1, 3-hexanediol, 3-methyl (C7) n-BO_2-3(ii) a1, 3-hexanediol, 4-methyl- (C7) E_6-8(ii) a1, 3-hexanediol, 4-methyl- (C7) PO₁(ii) a1, 3-hexanediol, 4-methyl (C7) nBO_2-3(ii) a1, 3-hexanediol, 5-methyl- (C7) E_6-8(ii) a1, 3-hexanediol, 5-methyl- (C7) PO₁(ii) a1, 3-hexanediol, 5-methyl- (C7) n-BO_2-3(ii) a1, 4-hexanediol (C6) (Me-E)_2-5) (ii) a1, 4-hexanediol (C6) PO₂(ii) a1, 4-hexanediol (C6) BO₁(ii) a1, 4-hexanediol, 2-methyl- (C7) E_6-8(ii) a1, 4-hexanediol, 2-methyl- (C7) PO₁(ii) a1, 4-hexanediol, 2-methyl- (C7) n-BO_2-3(ii) a1, 4-hexanediol, 3-methyl- (C7) E_6-8(ii) a1, 4-hexanediol, 3-methyl- (C7) PO₁(ii) a1, 4-hexanediol, 3-methyl- (C7) n-BO_2-3(ii) a1, 4-hexanediol, 4-methyl- (C7) E_6-8(ii) a1, 4-hexanediol, 4-methyl- (C7) PO₁(ii) a1, 4-hexanediol, 4-methyl- (C7) n-BO_2-3(ii) a1, 4-hexanediol, 5-methyl- (C7) E_6-8(ii) a1, 4-hexanediol, 5-methyl- (C7) PO₁(ii) a1, 4-hexanediol, 5-methyl- (C7) n-BO_2-3(ii) a1, 5-hexanediol, (C6) (Me-E)_2-5) (ii) a1, 5-hexanediol- (C6) PO₂(ii) a1, 5-hexanediol (C6) BO₁(ii) a1, 5-hexanediol, 2-methyl- (C7) E_6-8(ii) a1, 5-hexanediol, 2-methyl- (C7) PO₁(ii) a1, 5-hexanediol, 2-methyl- (C7) nBO_2-3(ii) a1, 5-hexanediol, 3-methyl- (C7))E_6-8(ii) a1, 5-hexanediol, 3-methyl- (C7) PO₁(ii) a1, 5-hexanediol, 3-methyl- (C7) n-BO_2-3(ii) a1, 5-hexanediol; 4-methyl- (C7) E_6-8(ii) a1, 5-hexanediol; 4-methyl- (C7) PO₁(ii) a1, 5-hexanediol, 4-methyl- (C7) n-BO_2-3(ii) a1, 5-hexanediol, 5-methyl- (C7) E_6-8(ii) a1, 5-hexanediol, 5-methyl- (C7) PO₁(ii) a1, 5-hexanediol, 5-methyl- (C7) n-BO_2-3(ii) a1, 6-hexanediol, (C6) (Me-E)_1-2) (ii) a1, 6-hexanediol- (C6) PO_1-2(ii) a1, 6-hexanediol- (C6) n-BO₄(ii) a1, 6-hexanediol, 2-methyl- (C7) E_2-5(ii) a1, 6-hexanediol, 2-methyl- (C7) n-BO₁(ii) a1, 6-hexanediol, 3-methyl- (C7) E_2-5(ii) a1, 6-hexanediol, 3-methyl- (C7) n-BO₁(ii) a2, 3-hexanediol (C6) E_2-5(ii) a2, 3-hexanediol (C6) n-BO₁(ii) a2, 4-hexanediol- (C6) (Me-E)_5-8) (ii) a2, 4-hexanediol (C6) PO₃(ii) a2, 4-hexanediol, 2-methyl- (C7) (Me-E)_1-2) (ii) a2, 4-hexanediol, 2-methyl- (C7) PO_1-2(ii) a2, 4-hexanediol, 3-methyl- (C7) (Me-E)_1-2) (ii) a2, 4-hexanediol, 3-methyl- (C7) PO_1-2(ii) a2, 4-hexanediol, 4-methyl- (C7) (Me-E)_1-2) (ii) a2, 4-hexanediol, 4-methyl- (C7) PO_1-2(ii) a2, 4-hexanediol, 5-methyl- (C7) (Me-E)_1-2) (ii) a2, 4-hexanediol, 5-methyl- (C7) PO_1-2(ii) a2, 5-hexanediol (C6) (Me-E)_5-8) (ii) a2, 5-hexanediol (C6) PO₃(ii) a2, 5-hexanediol, 2-methyl- (C7) (Me-E)_1-2) (ii) a2, 5-hexanediol, 2-methyl- (C7) PO_1-2(ii) a2, 5-hexanediol, 3-methyl- (C7) (Me-E)_1-2) (ii) a2, 5-hexanediol, 3-methyl- (C7) PO_1-2(ii) a 3, 4-hexanediol (C6) EO_2-5(ii) a 3, 4-hexanediol (C6) n-BO₁；

5.1, 3-heptanediol (C7) E_3-6(ii) a1, 3-heptanediol (C7) PO₁；1，3-heptanediol (C7) n-BO₂(ii) a1, 4-Heptanediol (C7) E_3-6(ii) a1, 4-heptanediol (C7) PO₁(ii) a1, 4-heptanediol (C7) n-BO₂(ii) a1, 5-heptanediol (C7) E_3-6(ii) a1, 5-heptanediol (C7) PO₁(ii) a1, 5-heptanediol (C7) n-BO₂(ii) a1, 6-heptanediol (C7) E_3-6(ii) a1, 6-heptanediol (C7) PO₁(ii) a1, 6-heptanediol (C7) n-BO₂(ii) a1, 7-heptanediol (C7) E_1-2(ii) a1, 7-heptanediol (C7) n-BO₁(ii) a2, 4-Heptanediol (C7) E_7-10(ii) a2, 4-Heptanediol (C7) (Me-E)₁) (ii) a2, 4 heptanediol (C7) PO₁(ii) a2, 4-heptanediol (C7) n-BO₃(ii) a2, 5-Heptanediol (C7) E_7-10(ii) a2, 5-Heptanediol (C7) (Me-E)₁) (ii) a2, 5-heptanediol (C7) PO₁(ii) a2, 5-heptanediol (C7) n-BO₃(ii) a2, 6-Heptanediol (C7) E_7-10(ii) a2, 6-Heptanediol (C7) (Me-E)₁) (ii) a2, 6-heptanediol (C7) PO₁(ii) a2, 6-heptanediol (C7) n-BO₃(ii) a 3, 5-Heptanediol (C7) E_7-10(ii) a 3, 5-Heptanediol (C7) (Me-E)₁) (ii) a 3, 5-heptanediol (C7) PO₁(ii) a 3, 5-heptanediol (C7) n-BO₃；

6.1, 3-butanediol, 3-methyl-2-isopropyl- (C8) PO₁(ii) a2, 4-pentanediol, 2, 3, 3-trimethyl- (C8) PO₁(ii) a1, 3-butanediol, 2, 2-diethyl- (C8) E_2-5(ii) a2, 4-hexanediol, 2, 3-dimethyl- (C8) E_2-5(ii) a2, 4-hexanediol, 2, 4-dimethyl- (C8) E_2-5(ii) a2, 4-hexanediol, 2, 5-dimethyl- (C8) E_2-5(ii) a2, 4-hexanediol, 3, 3-dimethyl- (C8) E_2-5(ii) a2, 4-hexanediol, 3, 4-dimethyl- (C8) E_2-5(ii) a2, 4-hexanediol, 3, 5-dimethyl- (C8) E_2-5(ii) a2, 4-hexanediol, 4, 5-dimethyl- (C8) E_2-5(ii) a2, 4-hexanediol, 3, 5-dimethyl- (C8) E_2-5(ii) a2, 5-hexanediol, 2, 3-dimethyl- (C8) E_2-5(ii) a2, 5-hexanediol, 2, 4-dimethyl (C8) E_2-5(ii) a2, 5-hexanediol, 2, 5-dimethyl- (C8) E_2-5(ii) a2, 5-hexanediol, 3, 3-dimethyl- (C8) E_2-5(ii) a2, 5-hexanediol, 3, 4-dimethyl- (C8) E_2-5(ii) a 3, 5-heptanediol, 3-methyl- (C8) E_2-5(ii) a1, 3-butanediol, 2, 2-diethyl (C8) n-BO_1-2(ii) a2, 4-hexanediol, 2, 3-dimethyl- (C8) n-BO_1-2(ii) a2, 4-hexanediol, 2, 4-dimethyl- (C8) n-BO_1-2(ii) a2, 4-hexanediol, 2, 5 dimethyl- (C8) n-BO_1-2(ii) a2, 4-hexanediol, 3,3-dimethyl- (C8) n-BO_1-2(ii) a2, 4-hexanediol, 3, 4-dimethyl- (C8) n-BO_1-2(ii) a2, 4-hexanediol, 3, 5-dimethyl- (C8) n-BO_1-2(ii) a2, 4-hexanediol, 4, 5-dimethyl (C8) n-BO_1-2(ii) a2, 4-hexanediol, 5, 5-dimethyl- (C8) n-BO_1-2(ii) a2, 5-hexanediol, 2, 3-dimethyl- (C8) n-BO_1-2(ii) a2, 5-hexanediol, 2, 4-Dimethyl- (C8) n-BO_1-2(ii) a2, 5-hexanediol, 2, 5-dimethyl- (C8) n-BO_1-2(ii) a2, 5-hexanediol, 3, 3-dimethyl- (C8) n-BO_1-2(ii) a2, 5-hexanediol, 3, 4-dimethyl- (C8) n-BO_1-2(ii) a 3, 5-heptanediol, 3-methyl (C8) n-BO_1-2(ii) a1, 3-propanediol, 2- (1, 2-dimethylpropyl) - (C8) n-BO₁(ii) a1, 3-butanediol, 2-ethyl-2, 3-dimethyl- (C8) n-BO₁(ii) a1, 3-butanediol, 2-methyl-2-isopropyl- (C8) n-BO₁(ii) a1, 4-butanediol, 3-methyl-2-isopropyl- (C8) n-BO₁(ii) a1, 3-pentanediol, 2, 2, 3-trimethyl- (C8) n-BO₁(ii) a1, 3-pentanediol, 2, 2, 4-trimethyl- (C8) n-BO₁(ii) a1, 3-pentanediol, 2, 4, 4-trimethyl- (C8) n-BO₁(ii) a1, 3-pentanediol, 3, 4, 4-trimethyl- (C8) n-BO₁(ii) a1, 4-pentanediol, 2, 2, 3-trimethyl- (C8) n-BO₁(ii) a1, 4-pentanediol, 2, 2, 4-trimethyl- (C8) n-BO₁(ii) a1, 4-pentanediol, 2, 3, 3-trimethyl- (C8) n-BO₁(ii) a1, 4-pentanediol, 2, 3, 4-trimethyl- (C8) n-BO₁(ii) a1, 4-pentanediol, 3, 3, 4-trimethyl- (C8) n-BO₁(ii) a2, 4-pentanediol, 2, 3, 4-trimethyl (C8) n-BO₁(ii) a2, 4-hexanediol, 4-ethyl- (C8) n-BO₁(ii) a2, 4-heptanediol, 2-methyl- (C8) n-BO₁(ii) a2, 4-heptanediol, 3-methyl- (C8) n-BO₁(ii) a2, 4-heptanediol, 4-methyl- (C8) n-BO₁(ii) a2, 4-heptanediol, 5-methyl- (C8) n-BO₁(ii) a2, 4-heptanediol, 6-methyl- (C8) n-BO₁(ii) a2, 5-heptanediol, 2-methyl- (C8) n-BO₁(ii) a2, 5-heptanediol, 3-methyl- (C8) n-BO₁(ii) a2, 5-heptanediol, 4-methyl- (C8) n-BO₁(ii) a2, 5-heptanediol, 5-methyl- (C8) n-BO₁(ii) a2, 5-heptanediol, 6-methyl- (C8) n-BO₁(ii) a2, 6-heptanediol, 2-methyl- (C8) n-BO₁(ii) a2, 6-heptanediol, 3-methyl- (C8) n-BO₁(ii) a2, 6-heptanediol, 4-methyl- (C8) n-BO₁(ii) a 3, 5-heptanediol, 2-methyl- (C8) n-BO₁(ii) a1, 3-propanediol, 2- (1, 2-dimethylpropyl) - (C8) E_1-3(ii) a1, 3-butanediol, 2-ethyl-2, 3-dimethyl- (C8) E_1-3(ii) a1, 3-butanediol, 2-methyl-2-isopropyl- (C8) E_1-3(ii) a1, 4-butanediol, 3-methyl-2-isopropyl- (C8) E_1-3(ii) a1, 3-pentanediol, 2, 2, 3-trimethyl- (C8) E_1-3(ii) a1, 3-pentanediol, 2, 2, 4-trimethyl- (C8) E_1-3(ii) a1, 3-pentanediol, 2, 4, 4-trimethyl- (C8) E_1-3(ii) a1, 3-pentanediol, 3, 4, 4-trimethyl- (C8) E_1-3(ii) a1, 4-pentanediol, 2, 2, 3-trimethyl- (C8) E_1-3(ii) a1, 4-pentanediol, 2, 2, 4-trimethyl- (C8) E_1-3(ii) a1, 4-pentanediol, 2, 3, 3-Trimethyl- (C8) E_1-3(ii) a1, 4-pentanediol, 2, 3, 4-trimethyl- (C8) E_1-3(ii) a1, 4-pentanediol, 3, 3, 4-trimethyl- (C8) E_1-3(ii) a2, 4-pentanediol, 2, 3, 4-trimethyl- (C8) E_1-3(ii) a2, 4-hexanediol, 4-ethyl- (C8) E_1-3(ii) a2, 4-heptanediol, 2-methyl- (C8) E_1-3(ii) a2, 4-heptanediol, 3 methyl- (C8) E_1-3(ii) a2, 4-heptanediol, 4-methyl- (C8) E_1-3(ii) a2, 4-heptanediol, 5-methyl- (C8) E_1-3(ii) a2, 4-heptanediol, 6-methyl- (C8) E_1-3(ii) a2, 5-heptanediol, 2-methyl- (C8) E_1-3(ii) a2, 5-heptanediol, 3-methyl- (C8) E_1-3(ii) a2, 5-heptanediol, 4-methyl- (C8) E_1-3(ii) a2, 5-heptanediol, 5-methyl- (C8) E_1-3(ii) a2, 5-heptanediol, 6-methyl- (C8) E_1-3(ii) a2, 6-heptanediol, 2-methyl- (C8) E_1-3(ii) a2, 6-heptanediol, 3-methyl- (C8) E_1-3(ii) a2, 6-heptanediol, 4-methyl- (C8) E_1-3(ii) a And/or 3, 5-heptanediol, 2-methyl- (C8) E_1-3(ii) a And

7. mixtures thereof.

Of the isomers of nonane, only 2, 4-pentanediol, 2, 3, 3, -tetramethyl-is highly preferred.

In addition to the aliphatic glycol primary solvents and some of their alkoxylated derivatives discussed above and below, some specific glycol ethers have also been found to be the primary solvents suitable for use in formulating the liquid concentrated clear fabric softener compositions of the present invention. Similar to aliphatic diols, it has been found that the suitability of each principal solvent is very selective, depending on, for example, the number of carbon atoms in the molecule of the particular glycol ether. For example, as given in Table VI, for the general formula HOCH₂-CHOH-CH₂-O-R (wherein R is C)₂-C₈Alkyl) glycerol ether series, only the formula HOCH₂-CHOH-CH₂-O-C₅H₁₁(3-pentyloxy-1, 3-propanediol, wherein C₅H₁₁Containing different pentyl isomers) having a Clog P value within a preferred range of about 0.25 to 0.62, are suitable for formulating the liquid concentrated clear fabric softeners of the present invention. These have been illustrated by the examples and comparative examples XXXIIA-7-XXXIIA-7F. Cyclohexyl derivatives (but not cyclopentyl derivatives) have also been found to be useful. Also, selectivity is manifested in the selection of aryl glyceryl ethers. Of the many possible aryl groups, only a few phenol derivatives are suitable.

The same narrow range of selectivity was also found for bis (hydroxyalkyl) ethers. Bis (2-hydroxybutyl) ether (instead of bis (2-hydroxypentyl) ether) was found to be suitable. For bis (cyclic hydroxyalkyl) analogs, bis (2-hydroxycyclopentyl) ether is suitable, but bis (2 hydroxycyclohexyl) ether is not. Non-limiting examples of synthetic methods for preparing certain preferred di (hydroxyalkyl) ethers are given below.

Butyl monoglyceryl ether (also known as 3-butoxy-1, 2-propanediol) is not well suited for formulating the liquid concentrated clear fabric softeners of the present invention. However, its polyethoxylated derivative, preferably from about triethoxylated to about nonaethoxylated, more preferably from about pentaethoxylated to about octaethoxylated, is a useful primary solvent as shown in Table VI.

All preferred alkyl glycol ethers and/or di (hydroxyalkyl) ethers that have been identified are given in table VI, with 1, 2-propanediol, 3- (n-pentyloxy) -; 1, 2 propanediol, 3- (2-pentyloxy) -; 1, 2-propanediol, 3- (3-pentyloxy) -; 1, 2-propanediol, 3- (2-methyl-1-butoxy) -; 1, 2-propanediol, 3- (isopentyloxy) -; 1, 2-propanediol, 3- (3-methyl-2-butoxy) -; 1, 2-propanediol, 3- (cyclohexyloxy) -; 1, 2-propanediol, 3- (1-cyclohex-1-enyloxy) -; 1, 3-propanediol, 2- (pentyloxy) -; 1, 3-propanediol, 2- (2-pentyloxy) -; 1, 3-propanediol, 2- (3-pentyloxy) -; 1, 3 propanediol, 2- (2-methyl-1-butoxy); 1, 3-propanediol, 2- (isopentyloxy) -; 1, 3-propanediol, 2- (3-methyl-2-butoxy) -; 1, 3-propanediol, 2- (cyclohexyloxy) -; 1, 3-propanediol, 2- (1-cyclohex-1-enyloxy) -; 1, 2-propanediol, 3- (butoxy) -, pentaethoxylate; 1, 2-propanediol, 3- (butoxy) -, hexaethoxylate; 1, 2-propanediol, 3- (butoxy) -, heptaethoxylate; 1, 2-propanediol, 3- (butoxy) -, octaethoxylate; 1, 2-propanediol, 3- (butoxy) -, nonaethoxylate; 1, 2-propanediol, 3- (butoxy) -; a propoxylate; 1, 2-propanediol, 3- (butoxy) -; dibutenyloxy; and/or 1, 2-propanediol, 3- (butoxy) -, tributyleneoxy; preferred aromatic glycerol ethers include: 1, 2-propanediol, 3-phenoxy; 1, 2-propanediol, 3-benzyloxy; 1, 2-propanediol, 3- (2-phenethyloxy) -; 1, 2-propanediol; 1, 3-propanediol, 2- (m-tolyloxy) -; 1, 3-propanediol, 2- (p-tolyloxy) -; 1, 3-propanediol, 2-benzyloxy; 1, 3-propanediol, 2- (2-phenethyloxy) -; and mixtures thereof. More preferred aromatic glycerol ethers include: 1, 2-propanediol, 3-phenoxy; 1, 2-propanediol, 3-benzyloxy; 1, 2-propanediol, 3- (2-phenethyloxy) -; 1, 2-propanediol, 1, 3-propanediol, 2- (m-tolyloxy) -; 1, 3-propanediol, 2- (p-tolyloxy) -; 1, 3-propanediol, 2- (2-phenethyloxy) -; and mixtures thereof. The most preferred di (hydroxyalkyl) ethers include: bis (2-hydroxybutyl) ether, and bis (2-hydroxycyclopentyl) ether.

Illustrative and non-limiting examples of synthetic methods for preparing these preferred alkyl and aryl monoglyceryl ethers are given below.

Preferred alicyclic diols and derivatives thereof include: (1) saturated diols and derivatives thereof, 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; 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; 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; 4-methyl-1, 3-cycloheptanediol; 5-methyl-1, 3-cycloheptanediol; 5-methyl-1, 4-cycloheptanediol; 6-methyl-1, 4-cycloheptanediol; 1, 3-cyclooctadiene; 1, 4-cyclooctadiene; 1, 5-cyclooctadiene; 1, 2-cyclohexanediol, 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, nonaethoxylate; 1, 2-cyclohexanediol, a propoxylate; 1, 2-cyclohexanediol, monobutoxide; 1, 2-cyclohexanediol, dibutoxylate; and/or 1, 2-cyclohexanediol, tributoxylate. The most preferred saturated alicyclic diols and derivatives thereof are: 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; 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; 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; 1, 2-cyclohexanediol, octaethoxylate; 1, 2-cyclohexanediol, nonaethoxylate; 1, 2-cyclohexanediol, a propoxylate; and/or 1, 2-cyclohexanediol, dibutoxylate.

Preferred aromatic diols include: 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, among them, 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; and/or 1-phenyl-1, 4-butanediol are most preferred.

As discussed above, all those unsaturated species that are associated with other preferred primary solvents in the same relationship as described above, i.e., 1 CH more than the corresponding saturated primary solvent₂Those unsaturated species of the radical will also be preferred. However, particularly preferred unsaturated diol primary solvents are: 1, 3-butanediol, 2, 2-diallyl-; 1, 3-butanediol, 2- (1 ethyl-1-propenyl) -; 1, 3-butanediol, 2- (2-butenyl) -2-methan-a radical-; 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, 4-butanediol, 2, 3-bis (1-methylethylidene) -; 1, 3-pentanediol, 2-vinyl-3-ethyl-; 1, 3-pentanediol, 2-vinyl-4, 4-dimethyl-; 1, 4-pentanediol, 3-methyl-2- (2-propenyl) -; 4-pentene-1, 3-diol, 2- (1, 1-dimethylethyl) -; 4-pentene-1, 3-diol, 2-ethyl-2, 3-dimethyl-; 1, 4-hexanediol, 4-ethyl-2-methylene-; 1, 5-hexadiene-3, 4-diol, 2, 3, 5-trimethyl-; 1, 5-hexanediol, 2- (1-methylvinyl) -; 2-hexene-1, 5-diol, 4-vinyl-2, 5-dimethyl-; 1, 4-heptanediol, 6-methyl-5-methylene-; 2, 4-heptadiene-2, 6-diol, 4, 6-dimethyl-; 2, 6-heptadiene-1, 4-diol, 2, 5, 5-trimethyl-; 2-heptene-1, 4-diol, 5, 6-dimethyl-; 3-heptene-1, 5-diol, 4, 6-dimethyl-; 5-heptene-1, 3-diol, 2, 4-dimethyl-; 5-heptene-1, 3-diol, 3, 6-dimethyl-; 5-heptene-1, 4-diol, 2, 6-dimethyl-; 5-heptene-1, 4-diol, 3, 6-dimethyl-; 6-heptene-1, 3-diol, 2, 2-dimethyl-; 6-heptene-1, 4-diol, 5, 6-dimethyl-; 6-heptene-1, 5-diol, 2, 4-dimethyl-; 6-heptene-1, 5-diol, 2-ethylene-6-methyl-; 6-heptene-2, 4-diol, 4- (2-propenyl) -; 1-octene-3, 6-diol, 3-vinyl-; 2, 4, 6-octatriene-1, 8-diol, 2, 7-dimethyl-; 2, 5-octadiene-1, 7-diol, 2, 6-dimethyl-;2, 5-octadiene-1, 7-diol, 3, 7-dimethyl-; 2, 6-octadiene-1, 4-diol, 3, 7-dimethyl- (Rosiridol); 2, 6-octadiene-1, 8-diol, 2-methyl-; 2, 7-octadiene-1, 4-diol, 3, 7-dimethyl-; 2, 7-octadiene-1, 5-diol, 2, 6-dimethyl-; 2, 7-octadiene-1, 6-diol, 2, 6-dimethyl- (8-hydroxyllinalool); 2, 7-octadiene-1, 6-diol, 2, 7-dimethyl-; 2-octene-1, 7-diol, 2-methyl-6-methylene-; 3, 5-octadiene-2, 7-diol, 2, 7-dimethyl-; 3, 5-octanediol, 4-methylene-; 3, 7-octadiene-1, 6-diol, 2, 6-dimethyl-; 4-octene-1, 8-diol, 2-methylene-; 6-octene-3, 5-diol, 2-methyl-; 6-octene-3, 5-diol, 4-methyl-; 7-octene-2, 4-diol, 2-methyl-6-methylene-; 7-octene-2, 5-diol, 7-methyl-; 7-XinAlkene-3, 5-diol, 2-methyl-; 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.

The primary alcohol solvent may also preferably be 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 mixtures thereof. More preferably, the primary alcohol solvent is 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, the primary alcohol solvent is selected from the group consisting of 2-ethyl-1, 3-hexanediol, 1, 2-hexanediol, and mixtures thereof.

When several derivatives of the same diol with different alkenyloxy groups can be used, for example 2-methyl-2, 3-butanediol with 3-5 ethyleneoxy groups, or 2 propyleneoxy groups, or 1 buteneoxy group, it is preferred to use the derivative with the fewest number of groups, i.e. in this case, the derivative with one buteneoxy group. However, such derivatives are also preferred when only about 1 to 4 ethyleneoxy groups are required to provide good formulation properties.

Unsaturated diol

It has surprisingly been found that there is a significant similarity between the acceptability (formulatability) of a saturated diol and its unsaturated congener or analog having a higher molecular weight. When the unsaturated primary solvent has an additional methylene group (i.e., CH) added per double bond in its formula₂) In this case, the unsaturated congener/analog would have the same formulability as the parent saturated primary solvent. In other words, there is a clear "rule of addition", i.e. for each well saturated primary solvent suitable for formulating clear concentrated fabric softener compositions, there is a suitable unsaturated primary solvent to which one or more CH's are added₂When adding each CH₂And (ii) removing two hydrogen atoms from two adjacent atoms of the molecule to form a carbon-carbon double bond, thus maintaining the number of hydrogen atoms in the molecule constant for the chemical formula of the "parent" saturated main solvent. This is due to the surprising fact that adding a CH₂To the solvent, the ClogP value is increased by about 0.53, and the removal of two hydrogen atoms to form a double bond decreases the ClogP value by a similar value, i.e., about 0.48, thereby compensating for the CH₂Is added. So, each time one CH is added₂A double bond is inserted as long as the Clog P value of the new solvent is maintainedWithin an effective range of 0.15 to 0.64, preferably 0.25 to 0.62, more preferably 0.40 to 0.60, one can prepare higher molecular weight unsaturated analogues/congeners containing at least one more carbon atom starting from a preferably saturated principal solvent, with one addition of each CH₂A double bond is inserted so that the total number of hydrogen atoms is the same as the total number of hydrogen atoms of the parent saturated primary solvent. The following are some illustrative examples.

2, 2-dimethyl-6-heptene-1, 3-diol (CAS No.140192-39-8) is the preferred C9-diol principal solvent and is believed to be produced by adding 2-methyl-1, 3-heptanediol or 2, 2-dimethyl-1, 3-hexanediol, as the preferred C8-diol principal solvent, suitably plus one CH₂A radical and a double bond.

2, 4-dimethyl-5-heptene-1, 3-diol (CAS No.123363-69-9) is the preferred C9-diol principal solvent, which can be considered to be obtained by adding the following preferred C8-diol principal solvents 2-methyl-1, 3-heptanediol or 2, 4-dimethyl-1, 3-hexanediol, suitably together with a CH₂A radical and a double bond.

2- (1-Ethyl-1-propenyl) -1, 3-butanediol (CAS No.116103-35-6) is the preferred C9-diol principal solvent, and is believed to be produced by adding 2- (1-ethylpropyl) -1, 3-propanediol or 2- (1-methylpropyl) -1, 3-butanediol, the preferred C8-diol principal solvent, to one CH, as appropriate₂A radical and a double bond.

2-vinyl-3-ethyl-1, 3-pentanediol (CAS No.104683-376) is the preferred C9-diol principal solvent, which can be considered to be the solvent obtained by adding suitably one CH to the following preferred C8-diol principal solvents, 3-ethyl-2-methyl-1, 3-pentanediol or 2-ethyl-3-methyl-1, 3-pentanediol₂A radical and a double bond.

3, 6-dimethyl-5-pentene-1, 4-diol (e.g. CAS No.106777-99-5) is the preferred C9-diol principal solvent, which can be considered to be by adding suitably one CH to either the following preferred C8-diol principal solvents 3-methyl-1, 4-heptanediol, 6-methyl-1, 4-heptanediol or 3, 5-dimethyl-1, 4-hexanediol₂A radical and a double bond.

5, 6-dimethyl-6-heptene-1, 4-diol (e.g., CAS No.152344-16-6) is the preferred C9-diol principal solvent, and can be considered by adding suitably one CH to either of the following preferred C8-diol principal solvents 5-methyl-1, 4-heptanediol, 6-methyl-1, 4-heptanediol or 4, 5-dimethyl-1, 3-hexanediol₂A radical and a double bond.

4-methyl-6-octene-3, 5-diol (CAS No.156414-25-4) is a preferred C9-diol principal solvent, which can be considered to be obtained by adding any of the following preferred C8-diol principal solvents 3, 5-octanediol, 3-methyl-2, 4-heptanediol or 4-methyl-3, 5-heptanediol, suitably with one CH₂Derived from radicals and a double bond。

Rosiridol (CAS No.101391-01-9) and isospiridol (CAS No149252-15-3) are two isomers of 3, 7-dimethyl-2, 6-octadiene-1, 4-diol, the preferred C10-diol primary solvent. They can be considered to be derived by adding, to any of the following preferred C8-diol primary solvents, 2-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, where appropriate, two CH2 groups and two double bonds.

8-Hydroxylinalool (CAS No.103619-06-3, 2, 6-dimethyl-2, 7-octadiene-1, 6-diol) is the preferred C10-diol principal solvent, which can be considered by adding suitably two CH's to any one of the following preferred C8-diol solvents 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-hexanediol₂Radicals and two double bonds.

2, 7-dimethyl-3, 7-octadiene-2, 5-diol (CAS No.171436-39-8) is the preferred C10-diol principal solvent, and can be considered by adding suitably two CH's to any of the following preferred C8-diol solvents 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-hexanediol₂Radicals and two double bonds.

4-butyl-2-butene-1, 4-diol (CAS No.153943-66-9) is the preferred C8-diol principal solvent and can be thought of as prepared by adding suitably one CH to either the following preferred C7-diol solvents 2-propyl-1, 4-butanediol or 2-butyl-1, 3-propanediol₂A radical and a double bond.

For the same reason, a higher molecular weight unsaturated congener is itself a poor solvent when it is derived from a poorly unavailable saturated solvent. For example, 3, 5-dimethyl-5-hexene-2, 4-diol (e.g., CAS No.160429-40-3) is a poorly unsaturated C8 solvent and can be considered to be derived from the following poorly saturated C7 solvents: 3-methyl-2, 4-hexanediol, 5-methyl-2, 4-hexanediol, or 2, 4-dimethyl-1, 3-pentanediol, while 2, 6-dimethyl-5-heptene-1, 2-diol (e.g., CAS No.141505-71-7) is a poorly unsaturated C9 solvent and can be considered to be derived from the following poorly saturated C8 solvents: 2-methyl-1, 2-heptanediol, 6-methyl-1, 2-heptanediol, or 2, 5-dimethyl-1, 2-hexanediol.

It has also been surprisingly found that the above addition rule, i.e. the saturated primary solvent, often has the exception of unsaturated analogues/congeners with equal acceptability, which exception relates to saturated diol primary solvents with two hydroxyl groups on two adjacent carbon atoms. In some cases (but not always), one or more CH groups are inserted between two adjacent hydroxyl groups of the poor solvent₂Groups, resulting in higher molecular weight unsaturated congeners that are more suitable for formulating clear, concentrated fabric softeners. For example, a preferred unsaturated 6, 6-dimethyl-1-heptene-3, 5-diol (CAS No.109788-01-4) without adjacent hydroxyl groups can be considered to be derived from an unusable 2, 2-dimethyl-3, 4-hexanediol with adjacent hydroxyl groups. In this case, it is believed that the 6, 6-dimethyl-1-heptene-3, 5-diol is derived from 2-methyl-3, 5-heptanediol or 5, 5-dimethyl-2, 4-hexanediol, which are also preferred, and are the primary solvents having no adjacent hydroxyl groups, is more reliable. In contrast, CH is inserted between two adjacent hydroxyl groups of the preferred primary solvent₂Groups, which can lead to the formation of unusable higher molecular weight unsaturated diol solvents. For example, a non-useful unsaturated 2, 4-dimethyl-5-hexene-2, 4-diol having no adjacent hydroxyl group (CAS No.87604-24-8) can be considered to be derived from the preferred 2, 3-dimethyl-2, 3-pentanediol having adjacent hydroxyl groups. In this case, it is more reliable if it is considered to be derived from 2-methyl-2, 4-hexanediol or 4-methyl-2, 4-hexanediol which never has adjacent hydroxyl groups and is not available at the same time. There are also instances where an unusable unsaturated solvent, which does not have an adjacent hydroxyl group, can be considered to be derived from an unusable solvent which has an adjacent hydroxyl group, such as the pair of 4, 5-dimethyl-6-hexene-1, 3-diol and 3, 4-dimethyl-1, 2-pentanediol. Therefore, the temperature of the molten metal is controlled,to infer the formulability of unsaturated solvents that do not have adjacent hydroxyl groups, one should start with a low molecular weight saturated congener that also does not have adjacent hydroxyl groups. That is, in general, when the distance/relationship between two hydroxyl groups is maintained constant, the relationship is more reliable. That is, the formulatability of higher molecular weight unsaturated congeners that also have adjacent hydroxyl groups is more reliable as inferred from saturated solvents that also have adjacent hydroxyl groups.

It has been found that the use of these particular primary alcohol solvents enables clear, low viscosity stable fabric softener compositions to be prepared at surprisingly low levels, i.e. below about 40% by weight of the composition. It has also been found that the use of such primary alcohol solvents allows for the preparation of highly concentrated fabric softener compositions which are stable and which can be diluted, for example from 2: 1 to 10: 1, to produce compositions having a lower fabric softener content but which are still stable.

As discussed previously, it is feasible to maintain the primary solvent at a minimum level as desired for the compositions of the present invention to achieve transparency or clarity. The presence of water plays an important role as to how much of the primary solvent is needed to obtain clarity in these compositions. The higher the water content, the higher the content of primary solvent (relative to the softener content) is needed to obtain the clarity of the product. Conversely, the lower the water content, the less the primary solvent (relative to the softener) is required. Thus, at low water levels of about 5% to 15%, the weight ratio of softener active to primary solvent is preferably from about 55: 45 to about 85: 15, more preferably from about 60: 40 to about 80: 20. At water levels of about 15% to about 70%, the weight ratio of softener to primary solvent is preferably about 45: 55 to about 70: 30, more preferably about 55: 45 to about 70: 30. However, at high water levels of about 70% to about 80%, the weight ratio of softener to primary solvent is preferably about 30: 70 to about 55: 45, more preferably about 35: 65 to about 45: 55. If the water content is further higher, the ratio of the softening agent to the main solvent should be higher.

Mixtures of the above-mentioned principal solvents are particularly preferred, since the problems associated with large amounts of solvent are safety-related problems. The mixture reduces the amount of either material present. The use of mixtures also reduces odor and flammability, particularly when one of the primary solvents is volatile and/or odorous (which is more likely for low molecular weight materials). Suitable solvents which may be used at low levels, which are insufficient to give a clear product, are 2, 2, 4-trimethyl-1, 3-pentanediol; an ethoxylate, diethoxylate or triethoxylate derivative of 2, 2, 4-trimethyl-1, 3-pentanediol; and/or 2-ethyl-1, 3-hexanediol. For the purposes of the present invention, these solvents can only be used in amounts which do not lead to stable or clear products. Preferred mixtures should be those whose solvent body is one or more of the solvents already defined above as the most preferred solvent. Preferably, mixtures of solvents are used, particularly when one or more of the preferred primary solvents are solid at room temperature, in which case the mixture is liquid or has a lower melting point, thus improving the processability of the softener composition.

It has also been found that a second solvent or mixture of second solvents can be substituted for a portion of the primary solvent or mixture of primary solvents of the present invention, while the second solvent itself is not useful as a primary solvent of the present invention, so long as an effective amount of the useful primary solvent of the present invention is still present in the liquid, concentrated, clear fabric softener composition. When at least about 15% softener active is present, an effective amount of the principal solvent of the present invention is at least greater than about 5%, preferably greater than about 7%, and most preferably greater than about 10% of the composition. The solvent used in place can be used in any amount, but is preferably about equal to or less than the amount of the principal solvent available in the fabric softener composition.

For example, although according to the invention, 1, 2-pentanediol, 1, 3-octanediol, and hydroxypivalyl hydroxypivalate of the general formula:

HO-CH₂-C(CH₃)₂-CH₂-O-CO-C(CH₃)₂-CH₂OH (CAS #1115-20-4) is a non-useful solvent, but these solvents, when mixed with a primary solvent, such as the preferred 1, 2-hexanediol primary solvent (where the 1, 2-hexanediol primary solvent is present in an effective amount), also produce liquid, concentrated, clear fabric softener compositions.

The primary solvent can be used to formulate translucent or clear compositions, or to reduce the temperature at which the composition appears translucent or clear. Thus, the present invention also includes methods of adding the principal solvent, in the amounts previously indicated, to a composition that is not translucent or opaque, or, if the transition temperature required to make the composition translucent or clear is too high, to lower it, or if the composition is clear, for example, at ambient temperature or at a particular low temperature, to lower its modified temperature, preferably by at least about 5 ℃, more preferably by at least about 10 ℃. The main advantage of the principal solvent is that it yields the greatest benefit for a given weight of solvent. It should be understood that the term "solvent" as used herein refers to the action of the principal solvent, and not to the physical form at a given temperature, since some principal solvents are solid at ambient temperature.

Alkyl lactate

Certain alkyl lactate esters, such as ethyl lactate or isopropyl lactate, have a Clog P value in the effective range of about 0.15 to 0.64 and form liquid, concentrated, clear fabric softener compositions with the fabric softener actives of the present invention, but in slightly higher amounts than more effective glycol solvents such as 1, 2-hexanediol. They may also be used to replace a portion of the other primary solvents of the present invention to form liquid, concentrated, clear fabric softener compositions. This is illustrated in examples I-C.

Novel compounds

Several of the above-mentioned primary solvents are novel compounds, which include: 1, 2-butanediol, 2, 3, 3-trimethyl-; 3, 4-pentanediol, 2, 3-dimethyl-; 2, 3-hexanediol, 4-methyl-; 2, 3-hexanediol, 5-methyl-; 3, 4-hexanediol, 2-methyl-; 3, 4-pentanediol, 2, 3-dimethyl-; 1, 3-propanediol, 2- (1, 1-dimethylpropyl) -; 1, 3-propanediol, 2- (1, 2-dimethylpropyl) -; 1, 3-propanediol, 2- (2, 2-dimethylpropyl) -; 1, 3-butanediol, 2- (1-methylpropyl) -; 1, 3-butanediol, 2-ethyl-2, 3-dimethyl-; 1, 3-butanediol, 2- (2-methylpropyl) -; 1, 3-butanediol, 2-methyl-2-isopropyl-; 1, 3-butanediol, 3-methyl-2-isopropyl-; 1, 3-butanediol, 3-methyl-2-propyl-; 1, 4-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- (2-methylpropyl) -; 1, 4-pentanediol, 2, 2, 3-trimethyl-; 1, 4-pentanediol, 2, 3, 3-trimethyl-; 1, 5-pentanediol, 2, 2, 3-trimethyl-; 1, 5-pentanediol, 2, 3, 3-trimethyl-; 1, 3-pentanediol, 2-ethyl-2-methyl-; 1, 4-pentanediol, 2-ethyl-2-methyl-; 1, 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-4-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-; 2, 4-pentanediol, 3-propyl-; 1, 3-hexanediol, 3, 3-dimethyl-; 1, 3-hexanediol, 2, 5-dimethyl-; 1, 3-hexanediol, 3, 4-dimethyl; 1, 3-hexanediol, 3, 5-dimethyl-; 1, 3-hexanediol, 4, 5-dimethyl-; 1, 4-hexanediol, 2, 2-dimethyl-; 1, 4-hexanediol, 2, 3-dimethyl-; 1, 4-hexanediol, 2, 4-dimethyl-; 1, 4-hexanediol, 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, 5-hexanediol, 2, 2-dimethyl-; 1, 5-hexanediol, 3, 4-dimethyl-; 1, 5-hexanediol, 3, 5-dimethyl-; 1, 5-hexanediol, 4, 5-dimethyl-; 1, 6-hexanediol, 2, 3-dimethyl-; 1, 6-hexanediol, 2, 4-dimethyl-; 1, 6-hexanediol, 3, 3-dimethyl-; 2, 4-hexanediol, 4, 5-dimethyl-; 2, 5-hexanediol, 2, 3-dimethyl-; 2, 5-hexanediol, 2, 4-dimethyl-; 2, 5-hexanediol, 3, 3-dimethyl-; 2, 6-hexanediol, 3, 3-dimethyl-; 1, 3-hexanediol, 4-ethyl-; 2, 4-hexanediol, 3-ethyl-; 2, 5-hexanediol, 3-ethyl-; 1, 3-heptanediol, 4-methyl-; 1, 3-heptanediol, 5-methyl-; 1, 3-heptanediol, 6-methyl-; 1, 5-heptanediol, 3-methyl-; 1, 5-heptanediol, 4-methyl-; 1, 6-heptanediol, 3-methyl-; 1, 6-heptanediol, 5-methyl-; 2, 4-heptanediol, 3-methyl-; 2, 5-heptanediol, 3-methyl-; 3, 5-heptanediol, 2-methyl-; 2, 6-octanediol; 2, 4-hexanediol, 3, 3, 4-trimethyl-; 2, 4-hexanediol, 3, 5, 5-trimethyl-; 2, 4-hexanediol, 4, 5, 5-trimethyl-; 2, 5-hexanediol, 3, 3, 4-trimethyl-; 2, 5-hexanediol, 3, 3, 5-trimethyl-; 1, 2-propanediol, 3- (butoxy) -, triethoxylate; 1, 2-propanediol, 3- (butoxy) -, tetraethoxylate; 1, 2-propanediol, 3- (2-pentyloxy) -; 1, 2-propanediol, 3- (3-pentyloxy) -; 1, 2-propanediol, 3- (2-methyl-1-butoxy) -; 1, 2-propanediol, 3- (isopentyloxy) -; 1, 2-propanediol, 3- (3-methyl-2-butoxy) -; 1, 2-propanediol, 3- (cyclohexyloxy) -; 1, 2-propanediol, 3- (1-cyclohex-1-enyloxy) -; 1, 3-propanediol, 2- (pentyloxy) -; 1, 3-propanediol, 2- (2-pentyloxy) -; 1, 3-propanediol, 2- (3-pentyloxy) -; 1, 3-propanediol, 2- (2-methyl-1-butoxy) -; 1, 3-propanediol, 2- (isopentyloxy) -; 1, 3-propanediol, 2- (3-methyl-2-butoxy) -; 1, 3-propanediol, 2- (cyclohexyloxy) -; 1, 3-propanediol, 2- (1-cyclohex-1-enyloxy) -; 1, 2-propanediol, 3- (butoxy) -, pentaethoxylate; 1, 2-propanediol, 3- (butoxy) -, hexaethoxylate; 1, 2-propanediol, 3- (butoxy) -, heptaethoxylate; 1, 2-propanediol, 3- (butoxy) -, octaethoxylate; 1, 2-propanediol, 3- (butoxy) -, nonaethoxylate; bis (2-hydroxybutyl) ether; and bis (2-hydroxycyclopentyl) ether.

Chelating agents

The compositions of the present invention each contain one or more chelating agents such as copper and/or nickel chelating agents. The addition of the chelating agent of the present invention aids in the reduction of the color former, thereby facilitating the clarity of clear or translucent compositions and reducing malodor. While not wishing to be bound by theory, it is believed that the addition of a chelating agent may reduce or reduce the presence of couplers that may be present in the fabric softening active. Furthermore, the presence of the chelating agent reduces or mitigates malodour caused by the fabric softening active.

Therefore, the composition of the present invention contains a chelating agent as an essential component of the present invention. The chelating agent is present in the composition in a range of about 0.001% to about 10% by weight of the composition, with a more preferred range of about 0.01% to about 5% by weight of the composition, and a most preferred range of about 0.01% to about 3% by weight of the composition.

Such water soluble chelating agents may be selected from the group consisting of amino carboxylates, amino phosphonates, multifunctional substituted aromatic chelating agents, and mixtures thereof. Defined and preferred below all refer to their acid forms. Aminocarboxylic acids suitable for use herein as chelating agents include ethylenediaminetetraacetic acid (EDTA), N-hydroxyethylethylenediaminetriacetic acid, nitrilotriacetic acid salt (NTA), ethylenediaminetetrapropionic acid salt, ethylenediamine-N, N '-diglutamate, 2-hydroxypropenediamine-N, N' -disuccinate, triethylenetetramine hexaacetate, Diethylenetriaminepentaacetate (DETPA) such as diethylenetriaminepentaacetic acid (DTPA), and ethanoldiglycine, including water soluble salts thereof such as alkali metal salts, ammonium salts, and substituted ammonium salts thereof, and mixtures thereof.

Amino phosphonates are also suitable chelating agents for use in the compositions of the present invention when at least low phosphorus levels are permitted in detergent compositions and include ethylenediamine tetra (ethylene phosphonate), diethylenetriamine-N, N', N "-penta (methanephosphonate) (DETMP), and 1-hydroxyethyl-1, 1-diphosphonate (HEDP). Preferably, these amino phosphonates do not contain alkyl or alkenyl groups with more than about 6 carbon atoms.

Chelating agents are typically used in the rinse process of the present invention in amounts of from about 2ppm to about 25ppm for a soak time of from 1 minute to several hours.

EDDS chelants (also known as ethylenediamine-N, N' -disuccinate) useful in the present invention are the materials disclosed in the above-cited U.S. patent 4704233 and have the following general formula (represented as the free acid):

as disclosed in this patent, EDDS can be prepared from maleic anhydride and ethylenediamine. The biodegradable [ S, S ] isomer of EDDS can be obtained by reacting 1, 2-dibromoethane with L-aspartic acid. EDDS used herein as a chelating agent is generally in its salt form, i.e. one or more of the four acid hydrogen atoms are replaced by a water-soluble cation M, such as sodium, potassium, ammonium, triethanolammonium and the like. As previously mentioned, the chelating agent is generally used in the rinse method of the present invention in an amount of from about 2ppm to about 25ppm for a soak time of from 1 minute to several hours. EDDS can be used with zinc cations at certain pH values.

As can be seen from the above, a wide variety of chelating agents can be used herein. Indeed, simple polycarboxylates such as citrates, oxosuccinates, and the like may be used, although such chelants are less effective by weight than aminocarboxylates and phosphonates. Thus, the amount can be adjusted to accommodate different chelating efficiencies. These chelating agents have a stability constant (complete dissociation of the chelating agent) for copper ions of at least 5, preferably at least 7. Typically the chelating agent will comprise from about 0.5% to 10%, more preferably from about 0.75% to 5% by weight of the composition. Preferred chelating agents include DETMP, DETPA, DTPA, NTA, EDDS and mixtures thereof, most preferably DTPA.

Clarity of the composition

The compositions of the present invention comprise a clear translucent fabric softening composition added by liquid rinse. By clear composition, it is intended that the composition of the present invention be virtually free of noticeable color, so that the composition is generally as clear as water. Of course, one of ordinary skill in the art will recognize that minor amounts of color may be present in the compositions of the present invention. In such a case, the composition of the invention, if contained in a suitable container having a compensating hue, causes the color of the composition to cancel and the composition becomes clear when viewed through the container.

The color or clarity of the compositions of the present invention can be determined by the Hunter color analysis method. The Hunter color analysis method is well known to each of ordinary skill in the art. This analysis was performed using a Hunter Lab color detector supplied by Hunter Labs of Reston, Va. To determine the color or clarity of the compositions of the present invention, a Hunter Lab color detector was able to perform two separate measurements, i.e., CIELAB color measurement and percent haze (%) in solution in instrumental transmission. Both measurements were measured in total transmission using a Hunter Lab color detector. Set conditions of the apparatus: the viewing area was 0.25 ", the pore size 0.25", UV filtered off, no UV lamp, deionized water as standard, using a 30mm cell.

CIELAB is a scale used to determine the color of a solution. Those of ordinary skill in the art are familiar with the CIELAB scale. The measurement of color difference comprises measuring the composition at a time point when mixing is started under specific conditions and then measuring the color of the composition after a set time. The difference between the starting point and the end point is the CIELAB color difference. Preferably, for the compositions of the present invention, the clear compositions have a CIELAB color difference of about 5 or less, more preferably about 1 or less, and most preferably about 0.1 or less, after storage for 10 days from the start to 130 ° F.

The percent haze, measured in transmission, determines the haze, i.e., the clarity of the composition. Preferably, the compositions of the present invention have a percent haze of about 90% or less, more preferably 50% or less, and most preferably about 25% or less, as measured by Hunter color Analyzer Transmission.

Optional Components

(A) Low molecular weight water-soluble solvents can also be used, and are used in amounts of 0% to about 12%, preferably about 1% to 10%, more preferably about 2% to 8%. When the content of the water-soluble solvent is at the same low level as the aforementioned main solvent, a clear product cannot be formed, but when the main solvent is insufficient to form a completely clear product, it can form a clear product. Such water-soluble solvents are therefore highly desirable. These solvents include: ethanol, isopropanol, 1, 2-propanediol, 1, 3-propanediol, propylene carbonate, and the like, but does not include any major solvent (B). These water-soluble solvents, when present in hydrophobic materials, such as softener actives, have a greater affinity for water than the primary solvent.

(J) Other optional Components

Other components that may also be added suitable for use in the present invention include, but are not limited to, dye transfer inhibiting agents, polymeric dispersing agents, soil release agents, scum dispersing agents, suds suppressors, optical brighteners or other brighteners or brighteners, dye fixatives, photobleach protectors, oxygen bleach protectors, fabric softening clays, antistatic agents, carriers, hydrotropes, processing aids, dyes or pigments, bactericides, colorants, perfumes, preservatives, opacifiers, antishrinking agents, anti-wrinkle agents, fabric edge levelers, stain removing agents, antimicrobials, anti-corrosion agents, and the like.

Particularly preferred optional components include water-soluble calcium and/or magnesium compounds that provide additional stability. Chloride salts are preferred, but salts such as acetate, nitrate, etc. can also be used. The calcium and/or magnesium salt is present in an amount of from 0% to about 2%, preferably from about 0.05% to 0.5%, more preferably from about 0.1% to 0.25%.

The present invention may also comprise other compatible components, including those disclosed in pending application Ser. No. 08/372068 filed by Rusche et al, 12.1.1995, application Ser. No. 08/372490 filed by Shaw et al, 12.1.1995, and application Ser. No. 08/277558 filed by Hartman et al, 19.7.1994, which are incorporated herein by reference.

Preparation of the principal solvent

Main solvent for preparing diol

The diol principal solvent of the present invention can be made by a variety of synthetic methods. The preparation method is selected according to the specific structure of each main solvent. In addition, most of the primary solvents can also be made by more than one process. Thus, the methods of preparation recited herein for each particular principal solvent are illustrative only and should not be considered as limiting.

The method A comprises the following steps: preparation of 1, 5-, 1, 6-and 1, 7-diols

Method 1

The synthetic process is a general process for the preparation of α, omega-type diols derived from substituted cyclic olefins, examples of which are alkylated isomers of cyclopentene, cyclohexene and cyclohepteneGeneral procedure for the alkylation of cyclic olefinsIs of the formula

Wherein each R is hydrogen or C₁-C₄Alkyl and x is 3, 4 or 5.

The cyclic olefin can be converted into the final product diol by a three-step reaction.

Step 1 is a reaction of a cycloolefin with ozone (O)₃) In a solvent such as anhydrous ethyl acetate to produce an intermediate ozonide. Step 2 ozonide is coated with palladium catalyst/H₂And the like to a dialdehyde which is then reduced in step 3 by boron hydride reduction to the desired diol.

1, 2-diols are generally prepared by the direct hydroxylation of suitable substituted olefins. For example

Wherein each R is hydrogen, alkyl, or the like.

In a typical reaction, an olefin is reacted with hydrogen peroxide (30%) and a catalytic amount of osmium tetroxide in t-butanol or other suitable solvent. The reaction was cooled to about 0 ℃ and allowed to stand overnight. Unreacted compounds and solvent are removed by distillation and the desired 1, 2-diol is isolated by distillation or crystallization.

The method 2 comprises the following steps: another method is to convert the olefin to an epoxide by reaction with m-chloroperbenzoic acid or peracetic acid in a solvent such as methylene chloride at a temperature of less than about 25 ℃. The epoxide produced by this chemical reaction is then ring-opened, for example by hydrolysis with alkene sulfuric acid, to produce a diol.

And step 3: the target product is produced by boron hydride reduction reaction.

Method 3

Another method for preparing these compounds is the direct hydroxylation of cyclic olefins using hydrogen peroxide and a catalytic amount of osmium tetroxide. This reaction produces a cyclic diol which is then converted to an open chain dialdehyde by periodate or lead tetraacetate. The dialdehyde is then reduced by boron hydride as in method 1 to produce the desired 1, 5-or 1, 6-diol, and the like.

The method B comprises the following steps: preparation of 1, 2-diols

Method 1

The method C comprises the following steps: preparation of 1, 3-diols

Acylation of enamines

The process is directed to the production of the common class of 1, 3-diols and to the adaptation to various structural features. Enamines are prepared from ketones and aldehydes, which react with acid chlorides to form acylation products. The acylated amine derivative is hydrolyzed back to the acylcarbonyl compound, which is the 1, 3-dicarbonyl precursor to the desired 1, 3-diol. The diol is formed by the reduction of a1, 3-dicarbonyl compound with boron hydride.

Thus, acetaldehyde (aldehydes) is reacted with a secondary amine, preferably a cyclic amine such as pyrrolidine or morpholine, in a solvent such as toluene under heating to reflux with the addition of a catalytic amount of p-toluenesulfonic acid. As the amine reacts (condenses) with the carbonyl compound, water is generated and removed, for example by refluxing through a water trap. After removal of the theoretical amount of water, the reaction mixture is stripped if necessary (e.g. under vacuum) to remove the solvent (in most cases the acylation reaction can be carried out in the same solvent system).

The anhydrous crude enamine containing excess amine is reacted at about 20 ℃ with the appropriate acid chloride to form the acylated enamine. The reaction is typically allowed to stir at room temperature overnight. The entire reaction product was then poured into crushed ice, stirred, and the mixture was made acidic with 20% HCl. This treatment hydrolyzes the enamine to the acylated dicarbonyl compound. The intermediate is then isolated by extraction and distillation to remove low boiling impurities, which are subsequently reduced with sodium borohydride to yield the desired 1, 3-diol.

The method D comprises the following steps: preparation of 1, 4-diols by aldol reaction and reduction

This typical reaction involves one or more aldehydes, one or more ketones, and mixtures thereof, which contain at least one α -hydrogen atom on the carbon atom adjacent to the carbonyl group, examples of certain reactants and certain possible end products thereof being as follows:

the aldehyde, ketone or mixture thereof to be condensed is placed in an autoclave under an inert atmosphere together with a solvent such as butanol or with a phase transfer medium such as polyethylene glycol. When the object is, for example, a mixed condensation of a ketone and an aldehyde, the two reactants are generally used in a molar ratio of 1: 1. A catalytic amount of a strongly basic catalyst, such as sodium methoxide, is added, typically about 0.5 to 10 mole% of the reactants. The autoclave is closed and the mixture is heated at about 35-100 c until most of the reactants are converted, which typically takes about 5 minutes to about 3 hours. This crude mixture is neutralized and the resulting carbonyl functionality is reduced by hydrogenation with raney nickel at about 100 c and about 50 atmospheres for about 1 hour. Volatile matter is removed by distillation, and the main solvent of the needed diol is obtained by vacuum distillation.

More information on this process is disclosed in Synthesis (3), 164-5(1975), a.pochini and r.ungaro; PCT int.appl.wo 9,507,254, Kulmala et al, 16 mar.1995; japan Pat.Appl.No.40,333, Sato et al, 9 Feb.1990, Japan Pat.Appl.No.299,240, Satc et al, 4 Dec.1989; eur. Pat. appl.no.367,743, Ankner, 9 May 1990, all of which articles and patents are incorporated herein by reference.

Illustrative examples: condensation and conversion of butyraldehyde and/or isobutyraldehyde to form octa-carbon-1, 3-diol

An aliquot of n-butanol (about 148 g, about 2 mol, from Aldrich) was placed in a 500 ml three neck round bottom flask equipped with a stir bar, internal thermometer, condenser and nitrogen seal and treated with sodium metal (about 2.3 g, about 0.1 mol, from Aldrich) until the sodium was completely dissolved. Then, a mixture of butyraldehyde (about 72 g, about 1 mole, from Aldrich) and isobutyraldehyde (about 72 g, about 1 mole, from Aldrich) was added and the system was maintained at about 40 ℃ until most of the starting aldehyde was reacted. Sulfuric acid was carefully added to neutralize the base catalyst, all salts were filtered off, and the solution was hydrogenated with raney nickel at about 100 c and about 50 atmospheres for about 1 hour to produce a mixture of eight carbon-1, 3-diols. The butanol solvent and any isobutanol formed in the hydrogenation are removed by distillation to form a mixture of octa-1, 3-diols such as 2, 2, 4-trimethyl-1, 3-pentanediol, 2-ethyl-1, 3-hexanediol, 2, 2-dimethyl-1, 3-hexanediol and 2-ethyl-4-methyl-1, 3-pentanediol. The mixture can be further purified by vacuum distillation or decolorization with activated carbon. The recovered solvent is used to produce the next batch of diol.

When only butyraldehyde was used in the reaction, the major product obtained was 2-ethyl-1, 3-hexanediol.

When only isobutyraldehyde was used in the reaction, the main product obtained was 2, 2, 4-trimethyl-1, 3-pentanediol. Mixed condensation reaction of butyraldehyde and methyl ethyl ketone and conversion to form a mixture of octa-carbon-1, 3-diols

Condition a. a portion of n-butanol (about 148 g, about 2 mol, from Aldrich) placed in a 500 ml three-necked round bottom flask equipped with a stir bar, internal thermometer, condenser and nitrogen seal was treated with sodium metal (about 2.3 g, about 0.1 mol, from Aldrich) until all the sodium was dissolved. Then, add butyraldehyde (about 72 grams, about 1 mole, Aldrich) and 2-butanone (about 72 grams, about 1 mole, Aldrich) mixture, and the system is maintained at about 40 degrees C until all of the starting butyraldehyde reaction. Sulfuric acid was carefully added to neutralize the base catalyst and filtered to remove all salts. Unreacted starting materials may also be removed by distillation together with the reaction solvent. The mixture containing the condensation reaction product is hydrogenated with raney nickel at about 100 c and about 50 atmospheres for about 1 hour to produce a mixture comprising 2-ethyl-1, 3-hexanediol, 2-ethyl-3-methyl-1, 3-pentanediol, 3, 5-octanediol, 3-methyl-3, 5-heptanediol, and small amounts of other 1, 3-diol isomers, e.g., eight carbon 1, 3-diols such as 3-methyl-2, 4-heptanediol and 3, 4-dimethyl-2, 4-hexanediol. This crude diol mixture may be further purified by fractional distillation.

Condition B: the above reaction was repeated except that 2 moles of butyraldehyde were used per 1 mole of 2-butanone. The reaction product contains a high proportion of such diols due to self-condensation of the aldehyde: i.e. 2-ethyl-1, 3-hexanediol, and the reaction products contain a high proportion of this diol due to the mixed condensation of aldehyde and 2-butanone: such as 2-ethyl-3-methyl-1, 3-pentanediol and 3, 5-octanediol, and also because of the self-condensation of 2-butanone, the products contain a low proportion of such diols: such as 3-methyl-3, 5-heptanediol and 3, 4-dimethyl-2, 4-hexanediol.

Condition C: the above condensation was repeated except that about 1 mole of 2-butanone was placed in the reaction vessel together with the solvent and the catalyst, and about 1 mole of butyraldehyde was gradually added. The reaction conditions are adjusted so that the self-condensation reaction of 2-butanone upon addition is slowed and the more reactive carbonyl group of the aldehyde reacts rapidly, which results in a higher proportion of diol formed by the condensation of 2-butanone with butyraldehyde and by the self-condensation reaction of 2-butanone and a lower proportion of diol formed by the self-condensation reaction of butyraldehyde in the reaction product.

Condition D: the above condensation reaction is repeated under low temperature conditions. 1.0 mole of 2-butanone was dissolved in 5 volumes of anhydrous tetrahydrofuran. The solution was cooled to about-78 ℃ and 0.95 moles of potassium hydride added in portions. When the evolution of hydrogen had ceased, the solution was left to stand for 1 hour to allow the equilibrium of the reaction to shift to the more stable enolate, and then 1 mole of n-butyraldehyde was slowly added with good stirring while maintaining the temperature at-78 ℃. After the addition was complete, the solution was gradually warmed to room temperature and sulfuric acid was carefully added for neutralization. The salts are filtered off. Unreacted raw materials and reaction solvent may be removed by distillation. The condensation product-containing mixture is hydrogenated with raney nickel at about 100 c and about 50 atmospheres for about 1 hour to produce the predominant diol from the condensation of the enolate of 2-butanone with butyraldehyde, i.e., 3, 5-octanediol, which can be purified by distillation. Mixed condensation of isobutyraldehyde and methyl ethyl ketone and conversion to octacarbon 1, 3-diol mixture

The above condensation reaction conditions A were repeated except that isobutyraldehyde was used instead of butylaldehyde. The condensation and reduction processes are similar. The final diol products 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 reaction of butyraldehyde, isobutyraldehyde and methyl ethyl ketone and conversion of butyraldehyde, isobutyraldehyde and methyl ethyl ketone into mixture of octa-carbon-1, 3-diol

The above condensation reaction conditions A were repeated except that each of butylaldehyde, isobutyraldehyde and 2-butanone was used in an amount of about 1 mole. Condensation and reduction reactions are similarly carried out to produce an eight carbon-1, 3-diol consisting essentially of: 2, 2, 4-trimethyl-1, 3-pentanediol, 2-ethyl-1, 3-hexanediol, 2-dimethyl-1, 3-hexanediol, 2-ethyl-4-methyl-1, 3-pentanediol, 2-ethyl-3-methyl-1, 3-pentanediol, 3, 5-octanediol, 2, 3-trimethyl-1, 3-pentanediol, 2-methyl-3, 5-heptanediol, and 3-methyl-3, 5-heptanediol, and further contains a small amount of other isomers produced by condensation reaction of methylene groups (not methyl groups) of 2-butanone.

Preferably, the mixture produced by condensing butyraldehyde, isobutyraldehyde, and/or methyl ethyl ketone contains no more than about 90 wt%, preferably no more than about 80 wt%, more preferably no more than about 70 wt%, still more preferably no more than about 60 wt%, and most preferably no more than about 50 wt% of any particular compound. In addition, the reaction mixture should not contain greater than about 95% by weight, preferably not greater than about 90% by weight, more preferably not greater than about 85% by weight, and most preferably not greater than about 80% by weight butyraldehyde or isobutyraldehyde.

Preparation method E

Preparation of 1, 4-diols by addition of acetylides to carbonyl compounds

Bimetallic acetylide Na^+-：C≡C：^-Na⁺With aldehydes or ketones to form unsaturated alcohols, e.g.

The acetylene diol is then reduced to an ene diol or completely reduced to a saturated diol. The reaction can also be carried out as follows: the slurry of acetylene monosodium salt, at a level of about 18%, is reacted with the carbonyl compound to form acetylene alcohol, which is converted to the sodium salt, and reacted with another mole of carbonyl compound to form the unsaturated 1, 4-diol. Where a mixture of carbonyl compound and diacetylene is used, a mixture of diols will be formed, whereas if a monoacetylene is used, a specific structure can be formed in high yield. Illustrative examples: preparation of 6-methyl-2, 5-heptanediol

Sodium acetylene slurry (at about 18% concentration in xylene) was reacted with isobutyraldehyde to form acetylene alcohols:

acetylene alcohols are converted with a base into sodium acetylene R-CHOH-C.ident.CNa, which is then reacted with 1 mole of acetaldehyde to form the acetylene diols R-CHOH-C.ident.C-CHOH-R'. If desired, this Compound (CH)₃)₂CH-CHOH-C≡C-CHOH-CH₃Can be isolated as an unsaturated diol and reduced by catalytic hydrogenation to the corresponding double bond-containing (instead of acetylene) species, or further reduced by catalytic hydrogenation to the saturated 1, 4-diol.

Method F

Preparation of substituted diols from cyclic anhydrides, lactones and esters of dicarboxylic acids

The process is useful for the preparation of diols, especially 1, 4-diols, from dicarboxylic anhydrides, diesters and lactones, but it is not limited to 1, 4-diols or tetracarboxylates.

Such diols are typically synthesized by reducing the parent anhydride, lactone or diester by hydrogenating sodium bis (2-methoxyethoxy) aluminum (Red-Al) with a reducing agent. Such a reducing agent is commercially available as a 3.1 mole solution of toluene, producing 1 mole of hydrogen per 1 mole of the reagent. Diesters and cyclic anhydrides require about 3 moles of Red-Al (for each mole of substrate). When alkyl substituted succinic anhydrides are used to illustrate this preparation, this typical reduction proceeds as follows:

the anhydride was first dissolved in anhydrous toluene and placed in a reaction vessel equipped with a dropping funnel, mechanical stirrer, thermometer and reflux condenser connected to calcium chloride and soda lime tubes to remove moisture and carbon dioxide. The reducing agent in toluene was placed in the dropping funnel and slowly added to the stirred anhydrous solution. The reaction was exothermic, bringing the temperature to about 80 ℃. This temperature was maintained at about 80 ℃ for the remainder of the dropwise addition, and after the addition was completed, this temperature was maintained for 2 hours.

The reaction mixture was then allowed to cool to room temperature. The mixture is then added to a stirred aqueous HCl solution (about 20% strength) cooled in an ice bath, the temperature being maintained at about 20-30 ℃. After acidification, the mixture was separated in a separatory funnel and the organic layer was washed with dilute saline solution until neutral as determined by pH paper. This neutral diol solution was dried over anhydrous magnesium sulfate, filtered, and then stripped under vacuum to give the desired diol.

Process G preparation of diols having one or both secondary or tertiary alcohol groups

This is a common method for preparing substituted diols from lactones and/or diesters by alkylation of the carboxyl group with methylmagnesium bromide (Grignard) or alkyllithium compounds (usually methyllithium), for example:

such alkylation can be generalized to diesters. An excess of methylating agent will produce a diol whose two alcohol groups are both tertiary alcohol groups.

Process H for the preparation of substituted 1, 3-, 1, 4-and 1, 5-diols

This method is a general method for producing some 1, 3-, 1, 4-and 1, 5-diols by utilizing the chemical reactions summarized in method A-1 and method A-2. The change is that the cycloalkene used in process A is replaced by a cycloalkadiene. The general formula of the raw material is:

wherein each R is H or C₁-C₄Alkyl and x is 1, 2 or 3.

The reaction is of process A type except that the primary solvent is produced in 1 mole of ethylene glycol per mole of diol required, for example 2, 2-dimethyl-1, 4-hexanediol from 1-ethyl-5, 5-dimethyl-1, 3-cyclohexanediol (CAS No. 79419-18-4):

preparation of polyethoxylated derivatives

The polyethoxylated derivative of the principal solvent for the diol is generally prepared in a high pressure reactor under a nitrogen atmosphere. An appropriate amount of ethylene oxide is added to the mixture of glycol solvent and potassium hydroxide at elevated temperature (about 80 c to about 170 c). The amount of ethylene oxide is calculated relative to the amount of glycol solvent so that the correct number of ethylene oxide groups are added per glycol molecule. When the reaction is complete, for example after 1 hour, residual unreacted ethylene oxide is removed in vacuo. Illustrative examples: preparation of tetraethoxylated 3, 3-dimethyl-1, 2-butanediol

To a 2 liter parr reactor equipped with a temperature controller, about 354 moles (about 3.0 moles) of 3, 3-dimethyl-1, 2-butanediol and about 0.54 moles of potassium hydroxide were charged. The reactor was purged with nitrogen and evacuated three times to a pressure of about 30mm hg. Nitrogen was then re-introduced to atmospheric pressure and heated to about 130 ℃. The pressure in the reactor was then adjusted to slightly below atmospheric pressure by slight vacuum. After ethylene oxide (about 528 grams, about 12.0 moles) was added over 1 hour while controlling the temperature to about 130 ℃ and reacting for about 1 hour, the contents were cooled to about 90 ℃ and vacuum was applied to remove any residual ethylene oxide.

Preparation of methyl-terminated polyethoxylated derivatives

The methyl-terminated polyethoxylated derivatives of glycols are generally prepared as follows: with selected diols in combination with methoxy poly (ethoxy) chloroethanes (i.e. CH) of desired chain length₃O-(CH₂CH₂O)_n-CH₂CH₂-Cl), or with an epoxy precursor of a diol and a methyl-terminated polyethylene glycol of desired chain length (i.e., CH)₃O-(CH₂CH₂O)_n-CH₂CH₂-OH), or a combination of the two methods. Illustrative examples: synthesis of methyl-terminated tetraethoxylated derivative (CH) of 2-methyl-2, 3-butanediol₃)₂C(OH)CH(CH)₃(OCH₂CH₂)₄OCH₃

One equipped with a magnetic stir bar, condenser, thermometer and temperature controller (Thermowatch)^®，I²R)^®Into a 1 liter three-necked round-bottomed flask of (1 liter), tetraethyleneglycol methyl ether (about 208 g, about 1.0 mol) and metallic sodium (produced by Aldrich, about 2.3 g, about 0.10 mol) were added,and the mixture was heated to about 100 ℃ under argon. After the sodium had dissolved, 2-methyl-2, 3-epoxybutane (about 86 grams, about 1.0 mole) was added and the solution was stirred overnight at about 120 ℃ under argon. It is composed of¹³C-NMR(dmso-d₆) Indicating that the reaction was complete because the epoxy peak had disappeared. The reaction mixture was 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 yield the desired crude polyether alcohol. Can be purified by vacuum fractional distillation.

Synthesis of methoxy triethoxy chloroethane

To a reactor equipped with a magnetic stir bar, condenser and temperature controller (Thermowatch, I)²R)^®To a 1 liter three neck round bottom flask, tetraethylene glycol methyl ether (about 208 grams, about 1.0 mole) was added under argon. Thionyl chloride (about 256.O g, about 2.15 moles) was added dropwise over 3 hours with good stirring, maintaining the temperature in the range of 50-60 ℃. The reaction mixture was then heated at about 55 ℃ overnight. Measurement of¹³C-NMR(D₂O), indicating a small 66ppm peak with only one unreacted alcohol and representing the chlorinated product (-CH)₂Cl) of 43.5 ppm. To this was slowly added saturated sodium chloride solution until thionyl chloride was destroyed. This was treated with about 300ml of saturated sodium chloride solution and extracted with 500ml of dichloromethane. The organic layer was dried and the solvent was removed on a rotary evaporator to yield crude methoxyethoxy chloroethane. It can also be purified by vacuum fractional distillation. Methyl-terminated tetraethoxylated derivative C of 2-methyl-1, 3-pentanediol₂H₅CH(OH)CH(CH₃)CH₂(OCH₂CH₂)₄OCH₃Synthesis of (2)

Alcohol C₂H₅CH(OH)CH(CH₃)CH₂OH (about 116 g, about 1.0 mol) was placed in a flask equipped with a magnetic stir bar, condenser and temperature controller (Thermowatch) along with solvent about 100ml tetrahydrofuran^®，I²R) in a 1 l three-necked flask. To this solution was added sodium hydride (about 32 g, about 1.24 mol) in portions and the system was kept at reflux until gas evolution ceased. Methoxytriethoxy chloroethane (about 242 g, about 1.2 moles, prepared as above) was added and the system was maintained at reflux for about 48 hours. The reaction mixture was cooled to room temperature and water was carefully added with stirring to decompose excess hydrogenThe tetrahydrofuran was removed on a rotary evaporator. The crude product is dissolved in about 400ml of water and sufficient sodium chloride is dissolved in the water to bring it to near saturation, and the mixture is extracted twice with about 300ml portions of dichloromethane. The combined dichloromethane layers were dried over sodium sulfate and the solvent was removed by rotary evaporator to yield crude product, which was further purified by bulb tube apparatus at about 150 ℃ under vacuum to remove unreacted starting materials and low molecular weight by-products. Further purification can also be performed by evaporation in vacuo to yield the title polyether.

Preparation of polypropoxylated derivatives

A magnetic stirring rod and solid CO₂The condenser, the addition funnel, the thermometer and the three-necked round-bottomed flask of the temperature control apparatus (thermo-O-Watch, 12R) were cooled, the air of the system was blown off with a stream of nitrogen and the reaction mixture was then closed with nitrogen. The reaction flask is charged with anhydrous alcohol or glycol to be propoxylated. Carefully add about 0.1-5 mole% metallic sodium in portions to the reaction vessel, with heating if necessary, to react all of the sodium. Then the reaction mixture is heated to about 80-130 ℃ and propylene oxide (from Aldrich) is added dropwise from a dropping funnel at such a rate that solid CO is maintained₂The cooling condenser produced a small amount of reflux. The addition of propylene oxide is continued until the amount needed to achieve the desired degree of propoxylation has been added. Heating was continued until all reflux of propylene oxide had ceased and the temperature was maintained for an additional about 1 hour to ensure completion of the reaction. The reaction mixture is then cooled to room temperature and a readily available acid, such as methanesulfonic acid, is carefully added to neutralize. Filtration removed all salts to give the desired propoxylated product. The average degree of propoxylation is generally as follows¹And (4) determining an integral value of the H-NMR spectrum.

Preparation of multibutoxylated derivatives

A magnetic stirring rod and solid CO₂The condenser, addition funnel, thermometer and temperature control device (thermo-O-Watch, 12R) three-necked round bottom flask were cooled, the air of the system was blown off with a nitrogen stream, and then the reaction mixture was closed with nitrogen.The reaction mixture was then heated to about 80-130 deg.C and α -butylene oxide (Aldrich) was added dropwise from a dropping funnel at such a rate that solid CO was maintained₂The cooling condenser produced a small amount of reflux. The addition of butylene oxide is continued until the amount required to effect the desired degree of butoxylation is complete. And continuing to heat until all reflux of the epoxy butane is stopped, and preserving the heat for about 1-2 hours to ensure the reaction to be complete. The reaction mixture is then cooled to room temperature and neutralized by careful addition of a readily available acid such as methanesulfonic acid. All salts were removed by filtration to give the desired butoxylated product. The average degree of butoxylation is generally as follows¹And (4) determining an integral value of the H-NMR spectrum.

Preparation of polytetramethyleneoxy derivatives

A portion of about 0.1 mole of the desired starting material, anhydrous alcohol or glycol, was placed in a three-necked round bottom flask equipped with a magnetic stirrer, condenser, internal thermometer, and argon seal system. If the desired average degree of "tetramethelenylation" is about one per hydroxyl group, about 0.11 moles of 2- (4-chlorobutoxy) tetrahydropyran (ICI) are added per mole of alcohol functional group. If desired, a solvent such as tetrahydrofuran, dioxane or dimethylformamide is added. Then, sodium hydride (about 5 mol% excess relative to the chlorine compound) was added in small portions with good stirring while maintaining the temperature at about 30-120 ℃. After the hydride has reacted, the temperature is maintained until all alcohol groups have been hexylated for about 4 to 24 hours. After the reaction is complete, it is cooled and methanol is carefully added in small portions to decompose the excess hydride. Approximately equal volumes of water were then added and the pH adjusted to about 2 with sulfuric acid. After heating to about 40 ℃ and incubation for about 15 minutes to hydrolyze the protecting group of tetrahydropyranyl, the reaction mixture was neutralized with sodium hydroxide, and the solvent was removed with a rotary evaporator. The residue was dissolved in ether or dichloromethane and filtered to remove salts. The crude product, after stripping, is a tetramethyleneoxylated alcohol or diol. Further purification can be achieved by vacuum distillation. If an average degree of final tetramethyleneoxidation of less than 1 is desired, then correspondingly smaller amounts of chloride and hydride are used. To achieve an average degree of tetramethylene formation greater than 1, the entire process is repeated in cycles until the accumulation reaches the target level.

Preparation of alkyl and aryl monoglyceryl ethers

The general process for preparing alkyl and/or aryl monoglycidyl ethers involves first preparing an alkyl glycidyl ether precursor, then converting it to a ketal, which is then hydrolyzed to the monoglycidyl ether (diol). The preferred n-pentylglyceryl ether (i.e., 3- (pentyloxy) -1, 2-propanediol) n-C is illustrated below₅H₁₁-O-CHOH-CH₂And (4) preparing OH.

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

To a three-neck two-liter round bottom flask equipped with a head stirrer, cold water condenser, mercury thermometer and addition funnel was added about 546 grams of aqueous NaOH (about 50% strength) and about 38.5 grams of tetrabutylammonium hydrogen sulfate (PTC, phase transfer catalyst). The contents of the flask were stirred to dissolve and then about 400ml of hexane (mixture of isomers, containing about 85% n-hexane) and about 200 grams of 1-pentanol were added. To the addition funnel was added about 418 grams of epichlorohydrin, which was then slowly added (dropwise) to the stirring reaction mixture. The temperature was gradually raised to about 68 ℃ due to the exothermic reaction. After the epichlorohydrin addition was complete, the reaction was allowed to continue for 1 hour (no exotherm).

The crude reaction mixture was diluted with about 500ml of warm water, stirred slowly, the aqueous layer was then settled and removed, the hexane layer was mixed and diluted with about 1ml of warm water, and the pH of the mixture was adjusted to about 6.5 by addition of dilute sulfuric acid. The aqueous layer was separated again and discarded, and then the hexane layer was washed three times with fresh water. The hexane layer was then separated and evaporated to dryness on a rotary evaporator to obtain crude n-amyl glycidyl ether.

Acetonide (conversion to ketal)

To a three-necked 2-liter round bottom flask (equipped with a head stirrer, cold water condenser, mercury temperature)A dial and addition funnel) about 1 liter of acetone was added. To this acetone was added about 1ml of SnCl with stirring₄. To the addition funnel located above the reaction flask, about 200 grams of the as-prepared n-amyl glycidyl ether was added. The glycidyl ether was added very slowly to the stirring acetone solution (adjusting its rate to control the exotherm). The reaction was allowed to proceed for about 1 hour after the glycidyl ether addition was complete (maximum temperature about 52 ℃).

Hydrolysis

The equipment is modified to carry out distillation, and a heating cover and a temperature controller are arranged. The crude reaction mixture was concentrated by evaporating about 600ml of acetone. To this cold concentrated solution was added about 1 liter of aqueous sulfuric acid (concentration about 20%) and about 500ml of hexane. The contents of the flask were then heated to about 50 ℃ with stirring (the equipment was adjusted to collect and separate the acetone that had evolved). The hydrolysis reaction was continued until TLC (thin layer chromatography) analysis confirmed that the reaction was completed.

The crude reaction mixture was cooled and the aqueous layer was separated and discarded. The organic layer was then diluted with about 1 liter of warm water and the pH adjusted to about 7 by the addition of dilute aqueous NaOH (1N). The aqueous layer was separated again and the organic phase was washed three times with fresh water. The organic phase is then separated off and evaporated using a rotary evaporator. The residue was then diluted with fresh hexane and the desired product was extracted into a methanol/water solution (weight ratio of about 70/30). The methanol/water solution was then evaporated to dryness by a rotary evaporator (further methanol was added to accelerate the evaporation of water). The residue was then filtered hot through a glass microfiber filter paper to obtain n-pentylmonoglyceryl ether.

Preparation of bis (hydroxyalkyl) ethers to Synthesis of bis (2-hydroxybutyl) ethers

A1 liter round bottom three neck flask equipped with a magnetic stirrer, internal thermometer, addition funnel, condenser, argon supply and heating mantle was purged with argon, then 1, 2-butanediol (about 1.2g, about 0.05 mol, from Aldrich) and metallic sodium were added and the sodium was dissolved. Heated to about 100 ℃ and added dropwise with stirring butylene oxide (about 71g, about 1 mole available from Aldrich). Heating was continued until the butylene oxide reflux ceased and continued for 1 hour to allow complete conversion. The mixture was neutralized with sulfuric acid, filtered to remove salts, and the liquid was vacuum fractionated to remove excess butanediol. The residue was the desired ether and was further purified by vacuum distillation. Synthesis of bis (2-hydroxycyclopentyl) ether

A1 liter three neck round bottom flask equipped with a magnetic stirrer, internal thermometer, addition funnel, condenser, argon supply and heating mantle was purged with argon. 1, 2-cyclopentanediol (about 306 g, about 3 moles, available from Aldrich) was then added, along with boron trifluoride etherate (about 0.14 g, about 0.01 moles, available from cis-trans isomer mixture, available from Aldrich). The reaction mixture is then incubated at about 10-40 ℃ while the cyclopentene oxide (about 84 g, about 1 mole available from Aldrich) is added dropwise with stirring until all the cyclopentene has reacted. The reaction mixture was neutralized with sodium hydroxide and the liquid was fractionated under vacuum to recover the excess cyclopentanediol. The desired ether is obtained as a residue. Further vacuum distillation may be carried out for purification.

The above disclosed methods are illustrative only and are not intended to be limiting, as they may be used to assist those skilled in the art in practicing the present invention.

All percentages, ratios and proportions herein are by weight unless otherwise specified. All documents cited are hereby incorporated by reference in their relevant part.

The following are non-limiting examples of the invention:

the following examples show clear or translucent products having acceptable viscosities.

The compositions in the following examples were made as follows: an oil stock solution of DEQA softener active was first made at room temperature. If the softener active is not liquid at room temperature, the softener active can be melted by heating to, for example, about 130-150F (about 55-66℃). Using IKA RW 25^®The mixer mixes the softener active at about 150rpm for about 2 to 5 minutes. On the other hand, HCl is mixed with Deionized (DI) water at room temperature to make an acid/water stock. The chelating agent is then added to the aqueous stock. If the softener active and/or primary solvent are not liquid at room temperature and heating is desired, the acid/water stock is also heated to a suitable temperature, for example about 100F (about 38℃) and maintained at that temperature with a water bath. Adding a primary solvent (which melts at a suitable temperature if its melting point is above room temperature) to the pre-mixture of softeners, andthis premix is mixed for about 5 minutes, then the acid/water stock is added to the softener stock and mixed for about 20 to 30 minutes, or mixed so that the composition becomes clear and homogeneous. The composition was air cooled to ambient temperature.

The following are suitable N, N-di (fatty acyl-oxyethyl) -N, N-dimethylammonium chloride fabric softener actives (DEQA's) having approximately the given fatty acyl distribution, from which the following compositions were made.Fatty acyl DEQA¹ DEQA² DEQA³ DEQA⁴ DEQA⁵C12 Trace 000C 1433000C 1644555C 1800566C 14: 13300C 16: 1117003C 18: 17473716867C 18: 24881111C 18: 301122C 20: 100222C 20 and higher 00200 unknown 00667 Total 9999100100102 IV 86-9088-20-3020-30455 TPU 49101313 TPU is the total number of polyunsaturated fatty acyl groups by weight.Fatty acyl DEQA⁶ DEQA⁷ DEQA⁸C14010C 1611255C 1842014C 14: 1000C 16: 1101C 18: 1274574C 18: 25063C 18: 3700 No Provisioning cis/trans (C18: 1) No Provisioning 7 No Provisioning TPU 576 No Provisioning 100IV 125-

Example I Components 12345678

Wt% DEQA¹ 26.6 43.2 - 26.6 - 26.6 26.6 26.6DEQA⁶-27.5-27.5-ethanol 6105.163.16462-Ethyl-1, 38-8989-hexanediol 1, 2-hexanediol 82016898916 DTPA 0.010.010.10.12.52.50.10.01 HCl (pH2-3.5) 0.0050.0050.0050.0050.0050.0050.0050.005 fragrance-10-Kathon-3 ppm 3 ppm-deionized water equilibrium

DEQA⁶N, N-di (coco-acyl-oxyethyl) -N, N-dimethylammonium chloride

The 2-ethyl-1, 3-hexanediol and 1, 2-hexanediol have Clog P values of 0.60 and 0.53, respectively, both within the preferred range of Clog P values.

The above examples demonstrate clear or translucent products with acceptable particle size.

Example IA

Comparative examples

Component 88A 8B 8C 8D 8E 8F

Wt% DEQA¹26.626.626.626.626.626.626.61, 2-hexanediol 16- - -1, 2-propanediol-16- - -1, 2-butanediol- -16- - -1, 2-pentanediol- - -16- - -1, 2-heptanediol- - -16- - -1, 2-octanediol- - -16-1, 2-octanediol- - -16-1, 2-decanediol- - -16 ethanol 6666666 HCl (pH2-3.5) 0.0050.0050.0050.0050.0050.0050.005 deionized water equilibrium

All of the 1, 2-alkyl diols of example IA, except 1, 2-hexanediol, had Clog P values in the effective range of 0.15 to 0.64. The composition of example I-8, containing only 1, 2-hexanediol, was a clear composition with acceptable viscosity at room temperature and at about 40F (about 4℃); the compositions of comparative examples I-8A to I-8F were not clear and/or did not have an acceptable viscosity.

Example IB

Comparative examples

Component 88G 8H 8I 8J 8K 8L

Wt% DEQA¹26.626.626.626.626.626.626.61, 2-hexanediol 16- - -1, 3-hexanediol-16- - -1, 4-hexanediol- -16- - -1, 5-hexanediol- - -16- - -1, 6-hexanediol- - -16- - -2, 4-hexanediol- - -16-2, 5-hexanediol- - -16 ethanol 66666- -16 ethanol66 HCl (pH2-3.5) 0.0050.0050.0050.0050.0050.0050.005 deionized water equilibrium

All the hexanediol isomers of example IB, except 1, 2-hexanediol, had Clog P values in the effective range of 0.15 to 0.64. The only 1, 2-hexanediol-containing composition of examples I-8 was a clear composition with acceptable viscosity at both room temperature and about 40F (about 4℃); the compositions of comparative examples I-8G to I-8L were not clear and/or did not have an acceptable viscosity.

Examples I to C

Comparative example

Component 88M 8N 8O 8P 8Q

Wt% DEQA¹26.626.626.626.626.626.61, 2-hexanediol 169.21399-1, 2-pentanediol-6.82- -6.81, 2-octanediol- -1- -9.2 ethyl lactate- - -9- -isopropyl lactate- - -9-ethanol 666666HCl (pH2-3.5) 0.0050.0050.0050.0050.0050.005 deionized water equilibrium

The compositions of examples I-8, I-8M and I-8N, which contain an effective amount of 1, 2-hexanediol, a preferred primary solvent, are clear compositions having acceptable viscosities at both room temperature and at about 40F (about 4℃). The compositions of examples I-8O and I-8P, which contain an effective amount of 1, 2-hexanediol, a preferred primary solvent, are clear compositions with acceptable viscosity and are also clear at about 40F (about 4℃) but leave a small layer on top but return to clear when returned to room temperature. The compositions of comparative examples I-8Q that did not contain an effective amount of the preferred 1, 2-hexanediol were not clear and/or did not have an acceptable viscosity.

Example II

1234567 component wt% DEQA¹ - 26.6 - 20.0 20.0 26.6 -DEQA⁶27.5-27.56.86.8-27.5 ethanol 5.165.13.8-45.1 Isopropanol- - -2-2-ethyl-1, 3- - -1618- - -hexanediol 1, 2-hexanediol 16- - -16-2, 5-dimethyl- - -162, 5-hexanediol 2-methyl-2-propyl-1616- - -1, 3-propanediol DTPA 0.010.050.090.10.010.10.05 HCl (pH about 2-3.5) 0.0050.0050.0050.0050.0050.0050.005 deionized Water equilibria

Example III

1234567 component wt% DEQA¹ - 26.6 - 26.6 26.6 26.6 -DEQA²26-26- - -26 ethanol 5.165.13.8-45.1 isopropanol- - -2-n-propanol 18- - -2-butanol-16- - -2-methyl-1-propanol- -18- - -2-2-methyl-2-propanol- - -20- - -2, 3-butanediol- - -18- -2, 3-dimethyl-1, 2-butanediol-16-2, 3-dimethyl-1, 2-butanediol, 183, 3-dimethyl-DTPA 0.10.12.50.010.012.50.1 CaCl₂Deionized water equilibrium of-0.25- - -HCl (pH about 2-3.5) 0.0050.0050.0050.0050.0050.0050.005

Example IV

A clear fabric softener having the following composition was manufactured and its clarity was determined. Clarity, field of view 0.25 ", pore size 0.25", UV filtered, no UV lamp, deionized water standard, 30mm cell was measured in total transmission mode using a Hunter Lab color detector. The CIELAB differences for this composition from the start to 10 days after storage at 120 ℃ F. were 0.04 (with DTPA) and 20.37 (without DTPA). The percent haze of this composition in transmission mode, when DTPA was added, was 1.51%.

The weight of the components

DEQA 26.00

Ethanol 2.00

Hexanediol 2.00

1, 2 hexanediol 17.00

HCl(1N) 0.25

Kathon(1.5％) 0.02

DTPA 0.01

Deionized water 52.72

Method profile

As previously mentioned, primary solvent B, and certain mixtures of primary solvent B with secondary solvents, can be formulated to contain softener active a (about 55% to 85%, preferably about 60% to 80%, more preferably about 65% to 75% by weight of the premix); primary solvent B (about 10% to 30%, preferably about 13% to 25%, more preferably about 15% to 20% by weight of the premix); and optionally a premix which may also contain a water soluble solvent in an amount of from about 5% to about 20%, preferably from about 5% to about 17%, more preferably from about 5% to about 15% of the amount of the premix. The primary solvent B may also be replaced by a mixture of an effective amount of primary solvent B with some of the previously disclosed unusable solvents. These premixes contain the desired amount of fabric softening active a, and a sufficient amount of primary solvent B, and optionally solvent C, to provide the premix with the desired viscosity at the desired temperature range. Typical viscosities suitable for processing are less than about 1000cps, preferably less than about 500cps, more preferably less than about 300 cps. The low temperature use improves safety by reducing solvent evaporation, reduces degradation and/or loss of biodegradable fabric softener actives, perfumes, and the like, reduces the need for heat, and thus saves processing costs. The result is an improved environmental impact and improved safety in manufacturing operations.

Examples of premixes and the processing methods in which they are used include premixes (which generally contain from about 55% to 85%, preferably from about 60% to 80%, more preferably from about 65% to 75% of fabric softener active A-referred to in the examples as DEQA)¹And DEQA⁸) Mixing with about 10% to 30%, preferably about 13% to 25%, more preferably about 15% to 20% of a primary solvent such as 1, 2-hexanediol, and about 5% to 20%, preferably about 5% to 15% of a water-soluble solventAnd (C) an agent such as ethanol and/or isopropanol.

When DEQA containing about 13% ethanol as described below is used¹1, 2-hexanediol as a fabric softening activeAs the primary solvent, the temperature at which the premix exhibits a clear and/or liquid state when it contains different amounts of the primary solvent is as follows:

about 25% 1, 2-hexanediol is clear below about-5 ℃ and liquid below about-10 ℃.

About 17% 1, 2-hexanediol is clear as low as about 0 ℃ and liquid as low as about-10 ℃.

About 0% 1, 2-hexanediol is clear as low as about 17 ℃ and liquid as low as about 0 ℃.

These premixes can be used to formulate the final composition in a process comprising the following steps:

1. making premixes of fabric softening actives, e.g. containing about 72% DEQA¹About 11% ethanol, and about 17% primary solvent, such as 1, 2-hexanediol, were allowed to cool to ambient temperature.

2. The premix is admixed with a perfume.

3. Water, chelate and HCl are made up as aqueous stock at room temperature.

4. The premix was added to water with good stirring.

5. With CaCl₂The solution is adjusted to the desired viscosity.

6. Dyes are added to obtain the desired color.

The fabric softening active (DEQA), primary solvent B, and optionally water soluble solvents may be used to formulate a premix which may be used in the subsequent preparation of the composition.

For commercial purposes, the above compositions are filled into containers, in particular bottles, more particularly transparent bottles made of polypropylene (although glass, oriented polyethylene may be substituted) although translucent bottles are also possible. The bottle may have a light blue hue to compensate for the yellow colour already present or that may be produced during storage. For short-term storage and very clear products, bottles with no or other shades can also be used. Bottles containing uv absorbers may also be used to reduce the effect of uv light on the contents, particularly highly unsaturated actives (uv absorbers may also be on the surface). Clarity and overall effectiveness of the container indicate the clarity of the composition, which reassures the consumer as to product quality.

Claims (22)

1. A clear fabric softening composition comprising:

A. from about 2% to about 80%, by weight of the composition, of a biodegradable fabric softener active selected from the group consisting of:

i. a compound having the formula:

wherein each R substituent is hydrogen or short chain C₁-C₆An alkyl or hydroxyalkyl group; each m is 2 or 3; each n is 1 to about 4; each Y is-O- (O) C-, - (R) N- (O) C-, -C (O) -N (R) -or-C (O) -O-; when Y is-O- (O) C-or- (R) N- (O) C-, each R¹The total number of carbon plus 1 in (A) is C₆-C₂₂But at most to the extent that: a R¹Or YR¹Is less than 12, and the other R¹Or YR¹Is at least about 16, and each R¹Comprising a long chain C₅-C₂₁Linear, branched, unsaturated or polyunsaturated alkyl, R¹The parent fatty acid of (a) has an average iodine value of from about 20 to about 140;

a compound having the formula:

wherein each Y, R¹And X^(-)Have the same meanings as described above; and

mixtures thereof;

B. less than about 40% by weight of the composition of principal solvent having a Clog P value of about 0.15 to about 0.64;

C. from about 0.001% to about 10%, by weight of the composition, of a chelate;

D. optionally, a low molecular weight water-soluble solvent sufficient to improve clarity, selected from the group consisting of: ethanol, isopropanol, propylene glycol, 1, 3-propanediol, propylene carbonate, and mixtures thereof, the water-soluble solvent being present in an amount such that it does not form a clear composition on its own; and

E. balance water.

2. A composition as claimed in claim 1 wherein each R in the fabric softening active¹Comprising a long chain C₅-C₂₁Branched or unsaturated alkyl, optionally substituted, in a ratio of branched alkyl to unsaturated alkyl of from 5: 95 to about 95: 5, and R for unsaturated alkyl¹The parent fatty acid of (a) has an average iodine value of from about 20 to about 140.

3. The composition of claim 2, wherein the composition comprises from about 15% to about 70% of the softener active, wherein each R substituent in the softener active is hydrogen or short chain C₁-C₃An alkyl or hydroxyalkyl group; each n is 2; each Y is-O- (O) C-; each R¹The sum of carbon (a) plus 1 is C₁₂-C₂₂And R is¹Is a branched alkyl group or an unsaturated alkyl group, the ratio of branched alkyl group to unsaturated alkyl group being from about 75: 25 to about 25: 75, and for unsaturated alkyl groups, R is¹The average iodine value of the parent fatty acid of (a) is from about 50 to about 130; and wherein the counter ion X-is selected from the group consisting of chloride, bromide, methosulfate, ethosulfate, sulfate, and nitrate.

4. A composition as claimed in claim 3 wherein each R substituent is hydrogen or short chain C₁-C₃An alkyl or hydroxyalkyl group; each n is 2; each R¹The sum of carbon plus 1 in (A) is C₁₂-C₂₀(ii) a And wherein the counter ion X-is selected from the group consisting of chloride, bromide, methosulfate, ethosulfate, sulfate, nitrate.

5. A composition as in claim 3 wherein each R substituent is selected from the group consisting of methyl, ethyl, propyl, hydroxyethyl and benzyl; each m is 2; each n is 2; each R¹The sum of carbon plus 1 in (A) is C₁₄-C₂₀While each R is¹Is a long carbon chain C₁₃-C₁₉Branched or unsaturated alkyl radicals, branchesThe ratio of alkylated alkyl groups to unsaturated alkyl groups is from about 50: 50 to about 30: 70; for unsaturated alkyl groups, this R¹The parent fatty acid of the group has an iodine value of from about 70 to about 115; wherein the counter ion X^-Is chloride.

6. A composition as in claim 1, wherein the polyunsaturated olefin group-containing fabric softening active is present in an amount of at least about 3% by weight of the total weight of the softener active present, and R¹The parent fatty acid of the base has an average iodine value of from about 60 to about 140.

7. The composition of claim 1 wherein said chelating agent is selected from the group consisting of diethylenetriaminepentaacetic acid, ethylenediaminetetraacetic acid, ethylenediamine-N, N '-disuccinic acid, diethylenetriamine-N, N', N "-penta (methylphosphonic acid), nitrilotriacetic acid, and mixtures thereof.

8. A composition as claimed in claim 7 wherein said chelating agent is diethylenetriaminepentaacetic acid.

9. The composition of claim 1, comprising from about 0.01% to about 5% by weight of the composition of said chelating agent.

10. A composition as claimed in claim 4 comprising from about 4% to about 50% of said fabric softener active.

11. A composition as claimed in claim 4 comprising from about 10% to about 40% of said fabric softener active.

12. A clear fabric softening composition comprising:

A. from about 2% to about 80%, by weight of the composition, of a biodegradable fabric softener active;

B. less than about 40% by weight of the composition of a principal solvent having a Clog P value of from about 0.15 to about 0.64;

C. from about 0.001 to about 10% by weight of the composition of a chelate; and

E. a balance of water; wherein the composition has a percent haze in the Hunter color analysis transmission mode of less than about 90%.

13. The composition of claim 12, wherein the Hunter color transmission mode has a percent haze of less than about 50%.

14. The composition of claim 13, wherein the Hunter color transmission mode has a percent haze of less than about 25%.

15. The composition of claim 12 wherein said chelating agent is selected from the group consisting of diethylenetriaminepentaacetic acid, ethylenediaminetetraacetic acid, ethylenediamine-N, N '-disuccinic acid, diethylenetriamine-N, N', N "-penta (methylphosphonic acid), nitrilotriacetic acid, and mixtures thereof.

16. A composition as claimed in claim 15 wherein said chelating agent is diethylenetriaminepentaacetic acid.

17. A composition as claimed in claim 12 wherein the biodegradable fabric softener active is selected from the group consisting of:

i. a compound having the formula:

wherein each R substituent is hydrogen or short chain C₁-C₆An alkyl or hydroxyalkyl group; each m is 2 or 3;each n is 1 to about 4; each Y is-O- (O) C-, - (R) N- (O) C-, -C (O) -N (R) -, or-C (O) -O-; when Y is-O- (O) C-or- (R) N- (O) C-, each R¹The sum of carbon plus 1 in (A) is C₆-C₂₂But the number is at its maximum: a R¹Or YR¹Is less than 12, and the other R¹Or YR¹Is at least 16 in total, and each R¹Comprising a long chain C₅-C₂₁Straight-chain, branched, unsaturated or polyunsaturated alkanesA group;

a compound having the formula:wherein each Y, R¹And X^(-)Have the same meanings as described above; and

mixtures thereof.

18. A composition as in claim 17 wherein each R in the fabric softening active¹Is a long chain C₅-C₂₅Branched alkyl or unsaturated alkyl, optionally substituted, in a ratio of branched alkyl to unsaturated alkyl of from 5: 95 to about 95: 5, and for unsaturated alkyl R¹The parent fatty acid of the base has an average iodine value of from about 20 to about 140.

19. The composition of claim 18, wherein the composition comprises about 15% to about 70% of the softener active, wherein each R substituent in the softener active is hydrogen or short chain C₁-C₃An alkyl or hydroxyalkyl group; each n is 2; each Y is-O- (O) C-; each R¹The sum of carbon (a) plus 1 is C₁₂-C₂₂And R is¹Is a branched alkyl group or an unsaturated alkyl group, the ratio of branched alkyl group to unsaturated alkyl group being from about 75: 25 to about 25: 75, and for unsaturated alkyl groups, R is¹The average iodine value of the parent fatty acid of (a) is from about 50 to about 130; and wherein the counter ion X-is selected from the group consisting of chloride, bromide, methosulfate, ethosulfate, sulfate, and nitrate.

20. A composition as claimed in claim 19 wherein each R substituent is hydrogen or short chain C₁-C₃An alkyl or hydroxyalkyl group; each n is 2; each R¹The sum of carbon plus 1 in (A) is C₁₂-C₂₀(ii) a And wherein the counterion X^-Selected from the group consisting of chloride, bromide, methosulfate, ethosulfate, sulfate, nitrate.

21. The composition as claimed in claim 19Wherein each R substituent is selected from the group consisting of methyl, ethyl, propyl, hydroxyethyl and benzyl; each m is 2; each n is 2;each R¹The sum of carbon plus 1 in (A) is C₁₄-C₂₀While each R is¹Is a long carbon chain C₁₃-C₁₉A branched alkyl group or an unsaturated alkyl group, the ratio of branched alkyl group to unsaturated alkyl group being from about 50: 50 to about 30: 70; for unsaturated alkyl groups, this R¹The parent fatty acid of the group has an iodine value of from about 70 to about 115; wherein the counter ion X^-Is chloride.

22. A composition as in claim 19, wherein the polyunsaturated olefin group-containing fabric softening active is present in an amount of at least about 3% by weight of the total weight of the softener active present, and R¹The parent fatty acid of the base has an average iodine value of from about 60 to about 140.