KR100467354B1 - High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine - Google Patents

Abstract

The present invention relates to a fabric softening composition consisting of a quaternary ammonium salt composed of a monoester component, a diester component and a triester component as a softener, and a method of preparing the same.

The amount of diester quaternary is at least about 55% by weight based on the total amount of quaternary ammonium salt and the amount of triester quaternary is less than about 25% by weight.

Description

HIGH DI (ALKYL FATTY ESTER) QUATERNARY AMMONIUM COMPOUND FROM TRIETHANOL AMINE} From Triethanol Amine

The present invention relates generally to softener compositions containing quaternary ammonium compounds having a high diester content and a low triester content and to methods of making the same.

The present invention relates to quaternized ester-based softener compositions containing high diester content and low triester content. Compositions of this type have very good softening performance and stability compared to compositions of the prior art.

Fabric softener compositions suitable for softening the fibers during washing and providing the benefits of static control are well known in the art. The composition usually contains, as a softening component, a quaternary ammonium compound which is actually insoluble in water with two long alkyl chains.

And the use of various quaternized esteramines which are used as fabric softeners are also known in the art. US Patent 4,339,391 to Hoffmann et al describes a series of quaternized ester-amines useful as fabric softeners.

U.S. Pat.No. 5,296,622 discloses fiber-softening properties obtained by reaction of unsaturated fatty acids containing at least 40 mol-% of trans-coordinated double bonds or their esters with alkanolamines and subsequent quaternization of the reaction product with alkylating agents. And quaternary ester amines having hydrophilicity are described.

Henkel WO / 93/21291 claims a textile treatment which contains a quaternary ammonium compound having 1, 2 or 3 acyloxyalkyl groups bonded to a nitrogen atom as a softener. If the so-called all or part of the acyl groups are derived from unsaturated fatty acids with at least 30% in cis form, this compound has a low viscosity.

US Pat. No. 5,023,003 to KAO describes emollient compositions comprising at least one quaternary ammonium salt of a compound of the structure:

Wherein R ¹ and R ² represent hydrocarbon radicals each having one unsaturated bond and 12-22 carbon atoms, preferably 16-22 carbon atoms, and R ³ and R ⁴ represent methyl, ethyl or Indicates:

Where n is an integer from 1 to 5 and Y is H or methyl; R ⁵ and R ⁶ each represent a hydrocarbon radical having one unsaturated bond and 11-21 carbon atoms; X represents halogen, CH ₃ SO ₄ , C ₂ H ₅ SO ₄ ; Wherein, in the stereoisomeric structure, if the salt comprises both cis- and trans-isomers, the ratio of cis-isomer and trans-isomer is in the range of 25/75 to 90/10)

US Patent No. 4,767,547 describes fiber softener compositions containing rapidly biodegradable quaternary ammonium softeners of the structure:

(In the above structural formula, R ₁ is (CH ₂ ) _n -QT ₂ or T ₃ ; R ₂ is (CH ₂ ) _n -QT ₄ or T ₅ or R ₃ ; R ₃ is C ₁ -C ₄ alkyl; T ₁ , T ₂ , T ₃ , T ₄ , T ₅ (identical or different) are C ₁₂ -C ₂₂ alkyl or alkenyl; n is an integer from 1 to 4; And X ⁻ is a softener-compatible anion and the composition has a pH of 2.5 to 4.2 at 20 ° C. in demineralized water when diluted to a concentration of 0.5% to 1% of the rapidly biodegradable quaternary ammonium compound)

WO 94/20597 to Procter & Gamble relates to softening compounds containing diester quaternary ammonium compounds, wherein fatty acid acyl groups have an Iodine Value of about 5 or more and less than about 100. When the iodine value is less than about 25, it has a cis-trans isomer weight ratio of about 30/70 or more, an unsaturation level of less than about 65 weight percent, and the compound is other than a normal polar organic solvent present in the raw material of the compound or the added electrolyte Without a viscosity modifier, it is possible to form concentrated aqueous compositions having a concentration of at least about 13% by weight at at least about 10 iodines.

Stephan EP 0 550 361 describes a cationic textile treatment composition comprising a quaternary ammonium compound which is a reaction product of a long chain fatty acid with a tertiary amine having a fatty acid to amine ratio of 1.85 to 1.4.

WO 91/01295 to Henkel describes quaternary ammonium compounds useful as a textile treatment agent in which fatty acids are reacted with alkanolamines and then alkylated to give quaternary compounds. The esterification reaction is carried out in the presence of an acid catalyst such as hypophosphoric acid. The final product contains the monoester, diester and triester components in a ratio of 10: 62: 28%. However, it does not describe a method for producing the final product having a high diester content of about 55% by weight or more and a low triester content of about 20% by weight or less.

Finally, WO 94/14935 by Henkel describes quaternary ammonium compounds derived from triethanolamine and concentrated fabric softener dispersions containing one, two or three fatty acid acyloxyethyl groups. When the proportion of the compound having two fatty acid acyloxyethyl groups is 50 mol% or more, the compound has a particularly low viscosity. However, the document does not describe how to raise the level of diesters, and does not mention any triester content in the final product.

It is therefore evident that the prior art described above does not consider or suggest quaternary diester-based softener compositions having high diester content and low triester content. Methods of preparing such products are also not considered.

Accordingly, it is an object of the present invention to provide quaternary diester products having high diester content and low triester content. It is a further object of the present invention to provide a fabric softener composition comprising the quaternary diester compound of the present invention as a main component. It is a further object of the present invention to provide a fabric softener composition which does not yellow and has desirable fabric softening properties such as improved biodegradability, viscosity, water absorption, stability and the like and improved softening performance. These and other objects are readily apparent from the following description.

Summary of the Invention

The present invention relates to a fabric softener composition comprising as a softener a quaternary ammonium salt mixture consisting of monoester, diester and triester components, wherein the amount of diester quaternary is 55% by weight based on the total amount of the quaternary ammonium salt mixture Above, the amount of the triester quaternary is less than 20% by weight. The present invention also relates to a process for preparing the softener.

The present invention relates generally to fabric softener compositions containing quaternary ammonium-based softeners having a high diester content and low triester content, and methods of making the same.

Quaternary ammonium compounds with particularly good performance and stability profiles are obtained by reacting C ₁₂ -C ₂₂ fatty acids or their hydrogenated products or mixtures of these acids with alkanolamines in the presence of an acid catalyst, wherein the fatty acids for alkanolamines The ratio of is 1.60 to 1.80. Subsequently, the obtained esteramine reaction product is quaternized to obtain the quaternary ammonium salt of the present invention.

Fatty acids are preferably C ₁₆ -C ₂₂ acids having a degree of unsaturation such that the iodine number (“IV”) is within the range of 20-90, more preferably 40-60 and more preferably 45-55. Preferred fatty acids include, but are not limited to, oleic acid, palmitic acid, erucic acid, icoic acid and mixtures thereof. Soybeans, iron oil, palms, palm kernels, rapeseeds, pig oil, mixtures thereof and the like are typical raw materials of fatty acids that can be used in the present invention. Partial hydrogenation may be applied if necessary to minimize polyunsaturation levels to improve the stability of the final product. It is also preferred that the fatty acids used in the process have a cis to trans ratio of 80:20 to 95: 5. More preferably, the trans isomer content of the fatty acid is less than 10%. The optimal trans-isomer content is 0.5-9.9%. Most preferred fatty acids are a mixture of iron oil / distilled iron oil with a cis: trans isomer ratio of at least 9: 1.

Alkanolamines usable in the present invention generally correspond to formula (I):

(In Formula 1, R ₃ , R ₁ and R ₂ are individually selected from C ₂ -C ₄ hydroxyalkyl groups.)

Preferred alkanolamines include, but are not limited to, triethanolamine, propanol diethanolamine, ethanol diisopropanolamine, triisopropanol amine and mixtures thereof. Triethanolamine is the most preferred alkanolamine.

The molar ratio of fatty acids to alkanolamines is in the range of 1.60-1.80, more preferably in the range of 1.65-1.75. Usually the best results are obtained when the molar ratio is 1.70.

Acid catalysts usable in the process include, but are not limited to, sulfonic acid, phosphorous acid, p-toluene sulfonic acid, methane sulfonic acid, oxalic acid, hypophosphoric acid or acceptable Lewis acids. Preferred acid catalysts are hypophosphorous acid. Typically 0.02-0.2% by weight, more preferably 0.1 to 0.15% by weight of the acid catalyst, based on the weight of fatty acid is used in the process.

The esterification reaction of a fatty acid with an alkanolamine is carried out at a temperature of 170 ° C. to 210 ° C. until the reaction product has an acid value of 5 or less. Triester formation in the final product can also be minimized by controlling the heating rate to form the esteramine mixture. A heating rate of 0.8 ° C.-3 ° C./min, preferably a heating rate of 1.25 ° C. to 3 ° C./min, and a temperature in the range of 170 ° C. to 210 ° C. at a temperature of 70 ° C. is effective to minimize triester formation.

After esterification, the crude product is reacted with an alkylating agent to obtain a quaternary ammonium product. Preferred alkylating agents include C ₁ -C ₃ straight or branched chain alkyl halides, phosphates, carbonates or sulfates, C ₇ -C ₁₀ aralkyl halides, phosphates or sulfates and mixtures thereof. Examples of preferred alkylating agents include, but are not limited to, methyl chloride, benzyl chloride, diethyl sulfate, dimethyl carbonate, trimethyl phosphate, dimethyl sulfate or mixtures thereof. The choice of type and amount of alkylating agent used is well known to those of ordinary skill in the art. Typically, when dimethyl sulfate is an alkylating agent, 0.7 to 1.0 mol of dimethyl sulfate per mole of ester is sufficient to produce a quaternary product.

The quaternization reaction is carried out in bulk or in a solvent in the temperature range of 60 ° C-120 ° C. If a solvent is used, then the starting materials and / or products can be dissolved in the solvent to the extent necessary for the reaction. Solvents of this kind are commonly known in the art. Suitable examples include, for example, lower alcohols, ie polar solvents such as C ₁ -C ₆ alcohols. Other solvents that may be used include, but are not limited to, monoglycerides, diglycerides and triglycerides, fatty acids, glycols, and mixtures thereof.

The quaternary ammonium salt mixture obtained comprises a mixture of the monoester of formula (2), the diester of formula (3) and the triester component of formula (4):

(In Formulas 2, 3 and 4, R has 12-22 carbon atoms, preferably 16-22 carbon atoms, and total IV in the range 20-90, preferably 40-60, more preferably 45-55. Having a hydrocarbon radical, wherein X ⁻ represents a softener compatible anion comprising, but not limited to, halogen, CH ₃ SO ₄ or C ₂ H ₅ SO ₄ )

The reaction product also contains small amounts of methyl trialkanolamine quaternary and other impurities. And the amount of diester in the final product is at least 55% by weight based on the total amount of quaternary ammonium salt product and the amount of triester is less than 25% by weight, preferably less than 20% by weight.

Typical product compositions contain less than 60-65 weight percent diester and less than 18 weight percent triester, more preferably less than 15 weight percent triester. And the ratio of the cis double bond to the trans double bond in the salt is preferably in the range of 80:20 to 95: 5. In the most preferred embodiment, the amount of trans isomer is less than 10%, ideally in the range of 5 to 9.5%.

There are several conventional methods for obtaining the desired cis: trans ratio of the quaternary ammonium salt product. A preferred method is to produce a quaternary ammonium salt mixture from fatty acids of the cis- and trans-isomers after adjusting the acid to the desired ratio.

Another method is to generate a quaternary ammonium salt mixture from the mixture after isomerizing some of the cis-isomer fatty acids or their esters with trans-isomers in the presence of a metallic catalyst to adjust their proportions. Other methods are well known to those of ordinary skill in the art.

The fabric softener compositions of the present invention with high diester content and low triester content show superior performance compared to typical esteramine quaternary compounds and further allow good color and odor stability in the formulation in producing high quality softening products. Let's do it. The composition is an aqueous liquid, preferably concentrated and contains 3-50% by weight, preferably 10-45% by weight, even more preferably 15-40% by weight of the quaternary ammonium compound of the present invention. The composition of the present invention can, if desired, be concentrated to a particulate solid containing 50-95%, preferably 60-90% quaternary ammonium softening compound.

Water may be added to the particulate solid composition to prepare a diluted or concentrated liquid fabric softener composition according to the present invention. Solid particulate compositions may also be added directly to the cleaning bath to provide a suitable concentration of use in the range of 10-1000 ppm, more preferably in the range of 50-500 ppm.

Quaternary ammonium compounds according to the invention can be prepared by reacting at least one C ₁₂ -C ₂₂ fatty acid having an IV of 20-90 with an alkanol amine, generally in the presence of an acid catalyst. The ratio of acid to amine is in the range of 1.6 to 1.8, and the reaction is carried out at a temperature of 175 ° C to 210 ° C until the reaction product has an acid value of 5 or less. Heating rates of 0.8 ° C. to 3.0 ° C. per minute are used to minimize triester formation. The esterified product is subsequently alkylated to obtain a quaternary ammonium product.

Standard cleansing-cycle softener compositions according to the invention can be prepared by preheating the water to a temperature of 45 ° C. to 60 ° C. in a suitable container and acidifying it to a pH of 2.7-3.2. The warmed quaternary ammonium salt mixture is added to acidic water with stirring while maintaining the temperature at 45 ° C to 60 ° C. The odorant and other optional ingredients can be dissolved into the emollient dispersion and then weighted by demineralized water. Such dispersions are typically storage stable in the temperature range of 4 ° C to 50 ° C.

Quaternary ammonium salt mixtures of the present invention may also be used in products other than fiber softener compositions. Such products include hair protection formulations, skin care formulations, and the like for softening, lubricating, softening and conditioning hair and / or skin when used in effective amounts. Such and other uses are well known to those skilled in the art.

The stability of the fabric softener composition of the present invention will be included with a wide variety of other optional ingredients even though stabilization of the cosurfactant is not required. A non-limiting brief description of any of the components used in the fabric softener composition of the present invention is provided below.

I ) Viscosity / Dispersion Aid

As already mentioned, the relatively concentrated compositions of the quaternary esters of the invention can be prepared stably without the addition of a concentration aid. However, the compositions of the present invention require organic and / or inorganic thickening aids to achieve high concentrations and / or to meet high stability criteria depending on other ingredients. Such thickening aids, typically viscosity modifiers, are necessary or desirable to maintain stability under extreme conditions when there is a specific softener activity level for IV.

Surfactants  Thickening aids

Surfactant thickening aids typically fall into four categories:

(1) single long chain alkyl cationic surfactants;

(2) nonionic surfactants;

(3) amine oxides; And

(4) fatty acids.

Mixtures of the above surfactant concentration aids can of course be used.

(1) single Long chain Alkyl  Cation Surfactants

Preferred single-long chain alkyl or ester based water soluble cationic surfactants are usually within the range of formula (5)

^{[R 2 N + (R)} 3] X -

(In Formula 5, the R ² group is a C ₈ -C ₂₂ hydrocarbon group, preferably a C ₁₂ -C ₁₈ alkyl group or a corresponding ester bond blocker having a short chain alkylene (C ₁ -C ₄ ) group between the ester bond and N and Having similar hydrocarbon groups, each R is (eg, by hydroxy) C ₁ -C ₆ unsubstituted or substituted alkyl or hydrogen, preferably methyl, and the counterion X ⁻ is, for example, chloride, bromide , Softeners such as methyl sulphate and compatible anions)

Cationic surfactants are usually added to the solid composition at a level of 0% to about 15%, preferably about 3% to about 15%, more preferably about 5% to about 15%. In liquid compositions, they are usually used at levels of from 0% to about 15%, preferably from about 0.5% to about 10%.

Usually, the total amount of single long chain cationic surfactant is added in an amount effective to obtain a stable composition.

This level represents the amount of single long chain alkyl cationic surfactant added to the composition of the present invention. This range does not include the amount of monoester already present in the diester quaternary ammonium compound.

The long chain group (R ² ) of the single long chain alkyl cationic surfactant is preferably from about 10 to about 22 carbon atoms for the solid composition, preferably from about 12 to about 16 carbon atoms and preferably about 12 to the liquid composition. To alkylene groups having from about 18 carbon atoms. The R ² group can be bonded to the cationic nitrogen atom via a group containing a crosslinking group, one or more esters, amides, ethers, amines, etc., preferably esters, which are preferred for increased hydrophilicity, biodegradability, and the like. The crosslinking group is preferably in about three carbon atoms of the nitrogen atom. Suitable biodegradable single long chain alkyl cationic surfactants containing ester linkages in the long chain are described in US Pat. No. 4,840,738, which is hereby incorporated by reference. If a corresponding non-quaternary amine is used, the particular acid added (preferably mineral or polycarboxylic acid) to keep the ester group stable will also retain the protonated amine in the composition, preferably during cleaning The amine has a cationic group. The composition is buffered (a pH of about 2 to about 5, preferably about 2 to about 4) to maintain a suitable and effective charge density in the aqueous liquid concentrated product, and upon dilution, for example, a less concentrated product is formed. And / or added to the cleaning cycle of the cleaning process.

The main function of the water soluble cationic surfactant is to increase the dispersibility of the diester softener, to lower the viscosity, and even if this is the case, the cationic surfactant itself does not need to have substantial softening properties. In addition, since it has a large solubility in water, a surfactant having only a single alkyl long chain can protect the diester softener reacting with the anionic surfactant and / or the detergent which enters the washing. Other cationic materials with ring structures such as alkyl imidazolines, imidazolimium, pyridine and pyridinium salts having a single C ₁₂ -C ₃₀ alkyl chain can also be used. Very low pH is required to stabilize the imidazoline ring structure. Several alkyl imidazolinium salts useful in the present invention have a structure of Formula 6:

(In Formula 6, Y ² is -C (O) -O-, -O- (O) C-, -C (O) -N (R ⁵ ), or -N (R ⁵ ) -C (O ), Wherein R ⁵ is hydrogen or a C ₁ -C ₄ alkyl radical; R ⁶ is a C ₁ -C ₄ alkyl radical; R ⁷ and R ⁸ are R as defined above for a single long chain cationic surfactant And R ² are each individually selected and only one is R ² )

Several alkyl pyridinium salts useful in the present invention have the structure of Formula 7:

(In Formula 7, R ² and X ⁻ are as defined above.)

Typical materials of this type are cetyl pyridinium chloride.

(2) Non-ion Surfactants - Alkoxylation  matter

Nonionic surfactants suitable as viscosity / dispersion modifiers include addition products of ethylene and / or propylene oxides with fatty alcohols, fatty acids, fatty amines, and the like. One of the alkoxylated materials described below can be used as nonionic surfactants. Usually, nonionic surfactants can be used at a level of about 5% to about 20%, preferably about 8% to about 15%, in a solid composition, and 0% to about 5%, preferably about 0.1 in a liquid composition. % To about 5%, more preferably about 0.2% to about 3%.

Suitable water soluble nonionic surfactants fall within the range of Formula 8:

R ² -Y- (C ₂ H ₄ O) _z -C ₂ H ₄ OH

(In Formula 8, R ² for solid and liquid compositions is primary, secondary and branched chain alkenyl hydrocarbyl groups; and primary, secondary and branched chain alkyl- and alkenyl-substituted phenolic. A hydrocarbyl group having a hydrocarbyl chain length having from about 8 to about 20, preferably from about 10 to about 18 carbon atoms)

More preferably, the hydrocarbyl chain length for the liquid composition has about 16 to about 18 carbon atoms and for the solid composition about 10 to about 14 carbon atoms. In Formula 8 for ethoxylated nonionic surfactants, Y is typically -O-, -C (O)-, -C (O) N (R)-or -C (O) N (R) R- Where R has the above meaning when present, and / or R can be hydrogen, and z is at least about 8, preferably at least about 10-11. The performance and stability of the softener composition decreases when there are few ethoxylate groups.

Nonionic surfactants are characterized by HLB (hydrophilic-lipophilic balance) of about 7 to about 20, preferably about 8 to about 15. By defining the number of ethoxylate groups and R ² , the HLB of most surfactants is measured. However, for concentrated liquid compositions, it is preferred that the nonionic surfactants contain relatively long chain R ² groups and be relatively ethoxylated. Shorter alkyl chain surfactants with short ethoxylated groups, while having the necessary HLB, are not effective. Nonionic surfactants as viscosity / dispersion modifiers are preferred over the other modifiers described herein for compositions having a high level of aromaticity.

Nonionic surfactants that may be used in the present invention include, but are not limited to, the following examples. In an embodiment, the number of ethoxyl groups in the molecule (EO) is defined as an integer.

(Iii) straight-chain, primary alcohols Alkoxylate

Decaethoxylates, undecaethoxylates, dodecaethoxylates, tetradecaethoxylates and pentadecaethoxylates of n-octadecanol and n-hexadecanol having HLB in the preferred range are It is useful as a viscosity / dispersion modifier. Preferred examples of ethoxylated primary alcohols useful herein as viscosity / dispersion modifiers of the composition include, but are not limited to, nC ₁₈ EO (10); And nC ₁₀ EO (11). Also useful herein are ethoxylates of natural or synthetic alcohols mixed within the “tallow” chain length range. Specific examples of such materials include Uji alcohol-EO (11), Uji alcohol-EO (18), and Uji alcohol-EO (25).

(Ii) straight-chain secondary alcohols Alkoxylates

Decaethoxylates, undecaethoxylates, dodecaethoxylates, tetradecaethoxylates of 3-hexadecanol, 2-octadecanol, 4-ecosanol and 5-icosanol having HLB in the preferred range , Pentadecaethoxylate, octadecaethoxylate and nonadecaethoxylate are useful as viscosity / dispersity modifiers of the present invention. Examples of ethoxylated secondary alcohols useful herein as viscosity / dispersity modifiers of the composition include, but are not limited to, 2-C ₁₆ EO (11); 2-C ₂₀ EO (11); And 2-C ₁₆ EO 14.

( Ⅲ ) Alkyl  phenol Alkoxylates

In the case of alcohol alkoxylates, hexa-octadecaethoxylates of alkylated phenols with HLB, in particular monovalent alkylphenols, in the preferred range, are useful as viscosity / dispersion modifiers. Hexa-ethoxylates to octadecaethoxylates such as p-tridecylphenol and m-pentadecylphenol are useful here. Preferred examples of ethoxylated alkylphenols useful as viscosity / dispersion modifiers include, but are not limited to, p-tridecylphenol EO (11) and p-pentadecylphenol EO (18).

It is generally recognized by those of ordinary skill in the art that phenylene groups in nonionic blends are equivalent to alkylene groups containing 2 to 4 carbon atoms. For this purpose, nonionic surfactants containing a phenylene group are considered to include the equivalent value of the carbon atom calculated as the sum of the carbon atoms of about 3.3 and the carbon atoms in the alkyl group for each phenylene group.

( Ⅳ ) Olefin Alkoxylates

Primary and secondary alkenyl alcohols, and alkenyl phenols corresponding to those described above, may be ethoxylated with HLB within the ranges recited above, and may be used as viscosity / dispersity modifiers in the compositions of the present invention. .

(Iii) branched chains Alkoxylates

Branched chain primary and secondary alcohols useful in the known “OXO” process can be ethoxylated and used as viscosity / dispersity modifiers in the present compositions.

The ethoxylated nonionic surfactants summarized above may be usefully used in the present compositions, either alone or in particular mixtures.

(3) amine Oxid

Suitable amine oxides include, but are not limited to, one alkyl or hydroxyalkyl component having about 8 to about 28 carbon atoms, preferably about 8 to about 16 carbon atoms, and about 1 to about 3 carbon sources Two alkyl components selected from the group consisting of hydroxyalkyl groups and alkyl groups having a valence. If used, the amine oxide is usually present in the solid composition at a level of from 0% to about 15%, preferably from about 3% to about 15%, and from 0% to about 5%, preferably from about 0.25% to about 2%. Present in the liquid composition. The total amine oxide amount is usually present in an amount effective to provide a stable composition.

Preferred examples of the amine oxide that can be used in the present invention include, but are not limited to, dimethyloctylamine oxide, diethyldecylamine oxide, bis- (2-hydroxyethyl) dodecylamine oxide, dimethyl dodecyl Amine oxides, dipropyltetedecylamine oxide, methylethylhexadecylamine oxide, dimethyl-2-hydroxyoctadecylamine oxide and coconut fatty alkyl dimethylamine oxide.

(4) fatty acids

Suitable fatty acids have fatty components containing about 10 to about 22, preferably about 10 to about 18, more preferably about 10 to about 14 carbon atoms, and about 12 to about 25 total carbon atoms. , Preferably containing from about 13 to about 22, more preferably from about 16 to about 20. The shorter component contains about 1 to 4, preferably about 1 to about 2 carbon atoms. Fatty acids are typically present at approximately the above defined levels for amine oxides. Fatty acids are preferred thickening aids for compositions which require a thickening aid and contain fragrance.

Electrolyte Concentration Formulation

Inorganic viscosity modifiers that can act similar to or increase the effect of surfactant thickening aids include water soluble ionization salts. The salts may also be optionally incorporated into the compositions of the present invention. A wide range of ionization salts can be used. Examples of suitable salts include, but are not limited to, halides of Group IA and IIA metals such as calcium chloride, magnesium chloride, sodium chloride, potassium bromide, and lithium chloride. Ionization salts are particularly useful during the process of preparing the compositions and mixing the components to achieve the desired viscosity.

The amount of ionization salt used depends on the amount of active ingredient used in the composition. Typical salt levels used to adjust the composition viscosity are from about 20 to about 20,000 ppm, preferably from about 20 to about 11,000 ppm, based on the weight of the composition.

Alkylene polyammonium salts can be incorporated into the composition to add to or instead of adjust the viscosity. In addition, the formulation may act as a scavenger to form ion pairs with the anion cleaner that moves during the main wash to clean, and may improve softening performance. The formulations can stabilize the viscosity over a wider temperature range, especially at low temperatures, compared to inorganic electrolytes. Specific examples of alkylene polyammonium salts include, but are not limited to, 1-lysine monohydrochloride and 1,5-diammonium-2-methylpentane dihydrochloride.

Ⅱ) Stabilizer

Stabilizers can also optionally be used in the compositions of the present invention. The term "stabilizer" as used herein includes antioxidants and reducing agents. The formulations are at levels of 0% to about 2%, preferably from 0.01% to about 0.2%, more preferably from about 0.05% to about 0.1% and more preferably from about 0.01% to about 0.2% for antioxidants. exist. The use of stabilizers ensures good odor stability under prolonged storage conditions. In addition, the use of antioxidant and reducing agent stabilizers is particularly important for unscented or low odor products.

Examples of antioxidants that may be used in the compositions of the present invention include, but are not limited to, those of ascorbic acid, ascorbic acid palmitate, propyl gallate, available from Eastman Chemical Products Inc. sold under Tenox PG and Tenox S-1 ™. mixture; A mixture of BHT (butylated hydroxytoluene), BHA (butylated hydroxyanisole), propyl gallate and citric acid, available from Eastman Chemical Products Inc., available under the trademark Tenox-6; Butylated hydroxytoluene from UOP Process Division, marketed under Sustane BHT; Tertiary butylhydroquinone from Eastman Chemical.

Tenox® TBHQ from Products, Inc .; Natural tocopherols available from Tenox® GT-1 / GT-2 from Eastman Chemical Products, Inc .; Butylated hydroxyanisole available from Eastman Chemical Products Inc. as BHA; Long chain esters of gallic acid such as dodecyl gallate (C ₈ -C ₂₂ ); Irganox® 1010; Irganox 1035; Irganox B 1171; Irganox 1425; Irganox 3114; Irganox 3125; And mixtures thereof; Preferably Irganox 3125, Irganox 1425; Irganox 3114 and mixtures thereof; And more preferably Dequest (trade name) available from Irganox 3125, Monsanto, 1-hydroxyethylidene-1, alone or in combination with citric acid and / or other chelators such as isopropyl citrate. ) 2010, 1-diphosphonic acid (ethidronic acid), Tiron (TM) and Aldrich available from Kodak, chemical name 4,5-dihydroxy-m-benzene-sulfonic acid / sodium salt DTPA ™ (diethylenetriaminepentaacetic acid). The chemical names and CAS numbers of some of the stabilizers are shown in the table below.

Antioxidant CAS number Chemical Names Used as Codes of Federal Regulations Irganox 1010 6683-19-8 Tetrakis [methylene (3,5-di-tert-butyl-4-hydroxyhydrocinnamate)] methane Irganox 1035 41484-35-9 Thiodiethylene bis (3,5-di-tert-butyl-4-hydroxyhydrocinnamate Irganox 1098 23128-74-7 N, N'-hexamethylene bis (3,5-di-tert-butyl-4-hydroxy hydrocinnamamide Irganox® B 1171 31570-04-4 1: 1 mixture of Irganox 1098 23128-74-7 and Irgafos 168 Irganox® 1425 65140-91-2 Calcium bis [monoethyl (3,5-di-tert-butyl-4-hydroxybenzyl) phosphonate] Irganox (trade name) 3114 27676-62-6 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) -s-triazine-2,4,6- (1H, 3H, 5H) trione Irganox ™ 3125 34137-09-2 3,5-di-tert-butyl-4-hydrate with 1,3,5-tris (2-hydroxyethyl) -S-triazine-2,4,6- (1H, 3H, 5H) -trione Roxy-hydrocinnamic acid triester Irgafos (trade name) 168 31570-04-4 Tris (2,4-di-tert-butylphenyl) phosphite

Examples of reducing agents include, but are not limited to, sodium borohydride, sodium bisulfide, hypophosphoric acid and mixtures thereof. The stability of the compounds and compositions can be improved by using stabilizers, but also the preparation of the compounds used and the source of hydrophobic groups can be important. Sources of hydrophobic groups such as, for example, fatty acids from tallow have a fragrance that remains with the compound despite chemical and mechanical process steps that convert the raw tallow into the final product. The source must be deodorized by, for example, absorption, distillation, dipping and the like known in the art. In addition, the addition of antioxidants, antibacterial agents and the like should be minimized to bring the resulting fatty acyl groups into contact with oxygen and / or bacteria.

Additional optional ingredients

Antifouling agent (soil release agent)

The composition of the present invention may optionally contain 0.1% to 10%, preferably 0.2% to 5% antifouling agent. Preferably the antifouling agent is a polymerizable antifouling agent such as containing a copolymerizable block of terephthalate and polyethylene oxide or polypropylene oxide, cationic guar gum and the like. US Pat. No. 4,956,447 describes a preferred antifouling agent composed of cationic functionalities, which is hereby incorporated by reference.

Preferred antifouling agents are those of polyethylene oxide and terephthalate consisting of repeating units of ethylene terephthalate and polyethylene oxide terephthalate having a molar ratio of ethylene terephthalate units to polyethylene oxide terephthalate units of from about 25:75 to about 35:65. A copolymer having blocks, wherein the polyethylene oxide terephthalate contains polyethylene oxide blocks having a molecular weight of about 300 to about 2,000. The molecular weight of the polymerizable antifouling agent is in the range of about 5,000 to about 55,000.

Another preferred polymeric antifouling agent is a repetition of ethylene terephthalate units containing from about 10% to about 15% of ethylene terephthalate units with from about 10% to about 50% of polyoxyethylene glycols having an average molecular weight of about 300 to about 6,000. It is a crystalline polyester having units, wherein the molar ratio of ethylene terephthalate units to polyoxyethylene terephthalate units in the polymerizable compound which can be crystallized is from 2: 1 to 6: 1. Examples of such polymers include, but are not limited to, Zelcon 4780 from DuPont and Milease T from ICI. Very preferred antifouling agents are polymers of formula (9):

(In Formula 9, X is a suitable capping group, each X is selected from the group consisting of H and alkyl or acyl groups containing from about 1 to about 4 carbon atoms, with methyl being preferred. It is selected to be water soluble, and is usually about 6 to about 113, preferably about 20 to about 50, and u is important for liquid formulations having a relatively high ionic strength, while the amount of material with u of at least 10 should be minimized, while material having a range of u from about 3 to about 5 should be at least 20%, preferably at least 40%)

The R ¹ component is originally a 1,4-phenylene component. As used herein, the term " R ¹ component is essentially a 1,4-phenylene component " means that the R ¹ component consists entirely of 1,4-phenylene components, or that other arylene or alkaliylene components, alkyl A compound partially substituted with a lene component, an alkenylene component or a mixture thereof. Alkaylene and arylene components which may be partially substituted with 1,4-phenylene include 1,3-phenylene, 1,2-phenylene, 1,8-naphthylene, 1,4-naphthylene, 2, 2-biphenylene, 4,4-biphenylene and mixtures thereof. Alkylene and alkenylene components which may be partially substituted are ethylene, 1,2-propylene, 1,4-butylene, 1,5-pentylene, 1,6-hexamethylene, 1,7-heptamethylene, 1 , 8-octamethylene, 1,4-cyclohexylene and mixtures thereof.

In the R ¹ component, the degree of partial substitution with a component other than 1,4-phenylene should be such that the antifouling properties of the compound are not adversely affected to a considerable extent. Generally, the degree of partial substitution that can be tolerated has a long main chain with a greater degree of partial substitution for the 1,4-phenylene component and depends on the main chain length of the compound. Usually compounds having R ¹ composed of about 50% to about 100% 1,4-phenylene components (0% to about 50% components other than 1,4-phenylene) have adequate antifouling activity. For example, a polyester having a molar ratio of 40:60 of isophthalic acid (1,3-phenylene) to terephthalic acid (1,4-phenylene) has a suitable antifouling activity. However, since most polyesters used in the fabrication are composed of ethylene terephthalate units, it is usually desirable to minimize the degree of partial substitution with components other than 1,4-phenylene for the best antifouling properties.

The R ¹ component is preferably composed entirely of 1,4-phenylene components (ie, comprised of 100%), ie, the R ¹ component is 1,4-phenylene.

For the R ² component, suitable ethylene or substituted ethylene components include, but are not limited to, ethylene, 1,2-propylene, 1,2-butylene, 1,2-hexylene, 3-methoxy-1,2 -Propylene and mixtures thereof. Preferably, the R ² component is essentially an ethylene component, a 1,2-propylene component or a mixture thereof. When the content rate of an ethylene component becomes high, there exists a tendency for the antifouling activity of a compound to improve. When the content ratio of the 1, 2- propylene component becomes high, there exists a tendency for a compound to improve water solubility.

The use of 1,2-propylene components or similar branched chain equivalents is preferred for incorporating a substantial portion of the antifouling component in the liquid fiber softener composition. Preferably about 75% to about 100%, more preferably about 90% to about 100% of the R ² component is a 1,2-propylene component. The value of each n is at least about 6, preferably at least about 10.

The value for each n is in the range of about 12 to about 113. Typically the value for each n is in the range of about 12 to about 43.

Cellulose derivatives also function as antifouling agents. Examples of the antifouling agent include, but are not limited to, hydroxyether of cellulose such as Methocel ™ by Dow Chemical; And cationic cellulose ether derivatives such as polymer JU-125 (trade name), JR-400 (trade name) and JR-30M (trade name) from Union Carbide.

Additional examples of cellulose polymerizable antifouling agents include methyl cellulose, hydroxypropyl methylcellulose, hydroxybutyl methylcellulose, or mixtures thereof, wherein the cellulose polymer has a viscosity of 15 to 75,000 centipoise in a 2% aqueous solution at 20 ° C. . Other effective antifouling agents are cationic guar gums such as Jaguar Plus ™ from Stein Hall and Gendrive 458 ™ from General Mills. A more complete description of highly desirable antifouling agents is described in Gosselink's European Patent Application No. 185,427, issued June 25, 1986, and US Patent No. 5,207,933, registered May 4, 1993. Later incorporated by reference.

disinfectant

Examples of fungicides that may be used in the compositions of the present invention include, but are not limited to, methyl, glutaraldehyde, formaldehyde, 2-bromo-2-nitropropane-1,3 sold by Bronopol (trade name) manufactured by Inolex Chemical. Of dimethyl and 2-methyl-4-isothiazolin-3-one and 5-chloro-2-methyl-4-isothiazolin-3-one sold by Kathon® CG / ICP from Rohm and Hass Company. Mixtures. Typical levels of fungicides used in the compositions are from about 1 ppm to about 2,000 ppm based on the weight of the composition, depending on the type of fungicide selected. Methyl paraben is less than 10% by weight of the diester component and is particularly effective for mold growth in aqueous fiber softener compositions.

silicon

In order to improve the softening properties and water absorption of the unsaturated quaternary ammonium salt mixtures of the formulas (2), (3) and (4), dimethylpolysiloxane (silicon) or modified silicone can be added to the composition of the present invention. Preferred are modified silicone or dimethylpolysiloxanes having a viscosity of 20-10000 cps at 25 ° C.

Modified silicones useful in the present invention include, for example, polyoxetylene modified silicones and amino-modified silicones, with the amount of modification being preferably less than 10%.

Dimethylpolysiloxanes or modified silicones are preferably emulsified with polyoxyethylene type nonionic surfactants or monoalkyl cation type or dialkyl cation type cationic surfactants before use.

Other optional ingredients

The present invention relates to other optional ingredients conventionally used in textile treatment compositions, for example, colorants, preservatives, optical bleaches, milk whites, fiber conditioners, surfactants, stabilizers such as guar gum, shrinkage agents, anti-wrinkle agents, fiber criss Ping agents, anti-spot agents, fungicides, preservatives, antifoams and the like.

Any further softener of the present invention is a nonionic fabric softener material. Typically the nonionic fiber softener material has an HLB of about 2 to about 9, more typically about 3 to about 7. The nonionic fiber softener materials are easily dispersed by themselves or in combination with other materials, such as one-long chain alkyl cationic surfactants, using hot water, and / or a mixture with other materials when further stirred. Easily distributed In general, the material of choice is relatively crystalline, has a high melting point (ie, above 50 ° C.), and is relatively insoluble in water.

The level of any nonionic softener in the solid composition is typically about 10% to about 40%, preferably about 15% to about 30%, and the ratio of any nonionic softener to the ester quaternary (TEQ) of the present invention. Is about 1: 6 to about 1: 2, preferably about 1: 4 to about 1: 2. The level of any nonionic softener in the liquid composition is typically from about 0.5% to about 10%, preferably from about 1% to about 5%. Preferred nonionic softeners are fatty acid partial esters of polyhydric alcohols or anhydrides thereof, the alcohols or anhydrides containing about 2 to about 18, preferably about 2 to about 8 carbon atoms, each fatty acid component of about 12 to about It contains about 30, preferably about 16 to about 20 carbon atoms. Typically the emollients contain about 1 to about 3, preferably about 2 fatty acid groups per molecule.

The polyhydric alcohol portion of the ester may be ethylene glycol, glycerol, poly (eg, di-, tri-, tetra-, penta-, and / or hexa-) glycerol, xylitol, sucrose, erythritol, pentaerythritol, It may be sorbitol or sorbitan. Particular preference is given to sorbitan esters and polyglycerol monostearate. The fatty acid portion of the ester is usually derived from fatty acids having from about 12 to about 30, preferably from about 16 to about 20 carbon atoms, and typical examples of such fatty acids are lauric acid, myristic acid, palmitic acid, stearic acid. Mountains and behenic acid.

Any highly nonionic softener that can be used in the present invention includes, but is not limited to, sorbitan esters and glycerol esters, esterified dehydration products of sorbitol. Sorbitol, typically prepared by catalytic hydrogenation of glucose, can be dehydrated in a known manner to form a mixture of 1,4-sorbitol anhydride and 1,5-sorbitol anhydride with a small amount of isosorbide. A typical method is described in US Pat. No. 2,322,821, which is hereby incorporated by reference. The kind of complex mixture of sorbitol anhydrides is referred to collectively as "sorbitan". And one of ordinary skill in the art will appreciate that the "sorbitan" mixture will also contain some free acyclic sorbitol.

Preferred sorbitan softeners can be prepared by esterifying the "sorbitan" mixture with a fatty acyl group in a standard reaction, ie by reaction with a fatty acid halide or fatty acid. The esterification reaction can take place in any of the useful hydroxyl groups, and esters of various monoesters, diesters and the like can be prepared. Mixtures of esters such as monoesters, diesters, triesters and the like are almost always obtained from the reaction, and the stoichiometric proportions of the reactants can be simply adjusted to obtain the desired reaction product.

To commercially prepare sorbitan ester materials, etherification and esterification are usually carried out in the same reaction step by directly reacting sorbitol with fatty acids. The method is described in MacDonald's "Emulsifiers:" Processing and Quality Control: Journal of the American Oil Chemists' Society, Vol. 45, October 1968, fully described. A detailed description including the chemical formula of the preferred sorbitan esters can be found in US Pat. No. 4,128,484, which is hereby incorporated by reference.

Certain derivatives of preferred sorbitan esters containing one or more non-esterified -OH groups from one to about 20 oxyethylene components [Tweens], in particular their "lower" ethoxylates (ie monoesters) , Diesters and triesters) are also useful in the compositions of the present invention. Therefore, for the purposes of the present invention, the term "sorbitan ester" includes such derivatives.

For the purposes of the present invention, if sorbitan esters are used, it is preferred that a significant amount of dissolbitan esters and trisolbitan esters are present in the ester mixture. Preference is given to ester mixtures having 20-50% di-esters and 10-35% tri-esters and tetra-esters. Commercially available materials such as sorbitan mono-esters (eg monostearate) contain significant amounts of diesters and triesters, and typical assays for sorbitan monostearate are about 27% monoesters, 32 It is composed of% diester and 30% triester and tetraester. Therefore commercial sorbitan monostearate is the preferred material. Mixtures of sorbitan stearate with sorbitan palmitate and 1,5-sorbitan esters having various stearate / palmitate weight ratios of 10: 1 to 1:10 are useful. 1,4-sorbitan esters and 1,5-sorbitan esters are also useful.

Other alkyl sorbitan esters useful for use in softener compositions include sorbitan monolaurate, sorbitan monomyristate, sorbitan monopalmitate, sorbitan monobehenate, sorbitan monooleate, sorbitan dilaurate, sorbitan Tan dimyristate, sorbitan dipalmitate, sorbitan distearate, sorbitan dibehenate, sorbitan dioleate and mixtures thereof and mixed ujialkyl sorbitan monoesters and ujialkyl sorbitan diesters. The mixture is readily prepared by reacting hydroxy-substituted sorbitan, in particular 1,4-sorbitan and 1,5-sorbitan, with the corresponding acid or acid chloride in a simple esterification reaction.

It is of course also known that commercial materials prepared by this method will usually consist of mixtures containing small amounts of acyclic sorbitol, fatty acids, polymers, isosorbide structures and the like. In the present invention, the impurities are preferably present at as low levels as possible.

Preferred sorbitan esters may contain small amounts of C ₈ , lower fatty acid esters as well as up to about 15% by weight of C ₂₀ -C ₂₆ esters and higher fatty acids. Glycerol and polyglycerol esters, in particular glycerol, diglycerol, triglycerol and polyglycerol monoesters and / or diesters, preferably monoesters. Glycerol esters can be prepared from naturally occurring triglycerides by the usual extraction, purification and / or interesterification methods or esterification methods of this kind for sorbitan esters. Partial esters of glycerin may also be ethoxylated to form usable derivatives encompassed within the term "glycerol ester".

Useful glycerol and polyglycerol esters include mono-esters and stearic acid, oleic acid, palmitic acid, lauric acid with stearic acid, oleic acid, palmitic acid, lauric acid, isostearic acid, myristic acid and / or behenic acid. Diesters of isostearic acid, behenic acid and / or myristic acid. Typical mono-esters include di-esters, tri-esters, and the like.

"Glycerol esters" also includes polyglycerols such as diglycerols to octaglycerol esters. Polyglycerol polyols are formed by condensation of glycerin or epichlorohydrin, which binds the glycerol component via ether linkages. Monoesters and / or diesters of polyglycerol polyols are preferred, and fatty acid acyl groups have been described above for sorbitan and glycerol esters.

The invention will be illustrated by the following non-limiting examples.

Example  One

Process for preparing 90% active softener composition

matter- TEEA Balance

BHT = 1.42 g

Hypophosphoric acid (50% solution) = 1.24 g

C ₁₆ -C ₁₈ or distilled tallow with C ₁₈ unsaturated fatty acids = 710 g

Triethanolamine (TEA) = 231.8 g

TEEA (fatty acid ester amine of TEA) was prepared in a 2 L-resin barrel connected to a top stirrer, a three-ball synthesizer column, an addition funnel, a distillation unit, a nitrogen sparger and a thermostat. The system was vacuum-leak tested before beginning the experiment.

Molten fatty acid, antioxidant and hypophosphorous acid were charged to the reaction flask and maintained at 65-75 ° C. under nitrogen. The vacuum was then purged with 29 "Hg (3742.1 Pa, 0.0374 bar) to remove air from the system, and the reactor was cleaned by rupturing the vacuum three times with nitrogen. Then, TEA was added and the reaction mixture was added after the addition. Heated at a ramp rate of 1.75 ° C. per minute. When the reaction temperature reached 105 ° C., the vacuum was brought to 26 ”Hg (3355.0 Pa, 0.0335 bar) and heated to 195-200 ° C. to continue the reaction. . At this temperature and pressure, the reaction was held for about 20 minutes. The free fatty acid was about 0.07 meq / g. The moisture level should be <0.1% or drying is required before quaternization.

Material-Ester 4 of the Invention Car ( TEQ Balance

TEEA = 306.3 g

Isopropanol = 41.3 g

DMS = 62.1 g

EDTA (40% solution) = 0.26 g

BHT = 0.21 g

TEEA was charged to the reactor, heated to 80 ° C. under nitrogen and dried for about 30 minutes. The dried TEEA was then cooled to 60 ° C. and isopropanol was added (5% batch weight). The heating net was then removed and DMS was added dropwise for a period of about 20 minutes. Because of the exothermic reaction, the reaction temperature is increased from about 50 ° C to about 85 ° C. The contents of the reactor were decomposed at 85-90 ° C. for about 2 hours. EDTA and BHT were then added and the remaining isopropanol (5%) was added to the mixture.

The product obtained had the following characteristics:

Appearance: viscous liquid at room temperature

Solvent: Isopropanol (IPA)

Activity: 90% active

Color (Gardner Scale): 2

pH (50/50 IPA: 1% in water) 3-4

Specific gravity: 0.978 g / cc

Cloud Point: 38-39 ℃

Pour Point: 19-21 ℃

Water: less than 0.5%

Ester Distribution (wt%): Mono: D: Tri is 26.5: 59.5: 10.5

Viscosity as a function of temperature of the product:

Example  2

"Standard" cleaning cycle softener formulation (7.5% active agent)

Raw material:

8.40% of quaternary salts of the present invention

DI-water 91.60%

1N HCl pH 2.7-3.2

Fragrance q.s.

Dye / colorants q.s.

Antibacterial q.s.

The water was preheated to 45-60 ° C. and the preheated water was placed in a suitable vessel and acidified to pH 2.7-3.2 with 1N HCl. A warmed quaternary salt was added to the acidified water and the temperature was maintained at 45-60 ° C. while stirring. The dispersion was cooled with stirring and the fragrance was dissolved at 40 ° C. with a softener dispersion. Preference is given to adding dyes and preservatives. The weight was adjusted with Dl-water. The dispersion is stored stably within the temperature range of 4-50 ° C.

Example  3

"Ultra" cleaning cycle softener formulation (24% active agent)

Raw material:

26.80% of quaternary salts of the present invention

DI-water 73.20%

1N HCl pH 2.7-3.2

10% aqueous calcium chloride (CaCl ₂ ) solution

Fragrance q.s.

Dye / colorants q.s.

Antibacterial q.s.

The DI-water was preheated to 50-60 ° C., the DI-water was placed in a mixing vessel and the acid was acidified to pH 2.7-3.2 with 1N HCl. A warmed quaternary salt was added to the acidified water and the temperature was maintained at 50-60 ° C. while stirring. After addition of 73% of the active agent, CaCl ₂ solution was added to the stirring dispersion. A second salt was added after 84% of the active agent was added, and a third small amount of salt was added when the active agent was added. Stirring was continued to make the dispersion soft and homogeneous. It stirred and cooled to 40 degreeC. The odorant was dissolved in the emollient dispersion. CaCl ₂ solution was added to adjust the viscosity to the desired level. Dye and preservatives were added. The weight was adjusted with Dl-water. The dispersion is stored stably within the temperature range of 4-50 ° C. For higher levels of softening, dispersions containing 28-40% active agent can be easily formulated using techniques similar to those shown above.

Example  4

Ultra-clean cycle softener formulation (28% active agent)

Raw material:

156 g of quaternary salt of the present invention

DI-water 315 g

1N HCl pH 2.7-3.2

10% aqueous calcium chloride (CaCl ₂ ) solution

Fragrance q.s.

Dye / colorants q.s.

Antibacterial q.s.

DI-water was preheated to 50-60 ° C., the DI-water was placed in a mixing vessel and acidified to pH 2.7-3.2 with 1N HCl. The molten quaternary salt was slowly added to the mixing vessel, and the temperature was maintained at about 60 ° C during mixing. The mixture was cooled to 40 ° C. with stirring and the odorant was dissolved with a softener dispersion. CaCl ₂ solution was added to adjust the viscosity to the desired level and colorants and preservatives were added. Finally the weight was adjusted with Dl-water. The dispersion is stored stably within the temperature range of 4-50 ° C.

Viscosity profile as a function of time at different temperatures

Viscosity as a function of time at different temperatures for 28% dispersion of ARMOSOFT TEQ

Claims (32)

A fabric softener composition having improved stability and softening performance comprising an effective amount of fabric softening, comprising a quaternary ammonium salt mixture having a monoester of formula (2), a diester of formula (3) and a triester component of formula (4): (Formula 2) (Formula 3) (Formula 4) (In Formula 2, 3, 4, R may be the same or different, and represents a substituted or unsubstituted hydrocarbon radical having 12-22 carbon atoms, wherein R ₁ ', R ₂ ' and R ₃ 'are Individually selected from C ₂ -C ₄ alkyl groups, R ₄ ′ is C ₁ -C ₃ straight or branched chain alkyl or C ₇ -C ₁₀ aralkyl) Based on the total amount of the quaternary ammonium salt mixture, the diester component (Formula 3) is 55 to 100% by weight, the triester component (Formula 4) is characterized in that it comprises more than 0% by weight less than 25% by weight Fabric softener composition. The method of claim 1, The cis / trans isomer ratio of the quaternary ammonium salt mixture is in the range of 80/20 to 95/5. The method of claim 1, And the cis / trans ratio is at least 90/10. The method of claim 1, The quaternary ammonium salt mixture is 3 to 50% by weight based on the total weight of the composition of the fabric softener composition. The method of claim 1, The quaternary ammonium salt mixture is a fabric softener composition comprising at least 55% by weight 100% by weight of the diester component (Formula 3) and more than 0% by weight less than 20% by weight of the triester (Formula 4). The method of claim 1, The quaternary ammonium salt mixture fabric softener composition, characterized in that it comprises at least 60% by weight 100% by weight of the diester component (Formula 3) and more than 0% by weight less than 15% by weight of the triester component (Formula 4). The method of claim 1, And wherein the R group represents a hydrocarbon radical having 16 to 22 carbon atoms and an iodine number of 30 to 60. The method of claim 1, Wherein the R group represents a hydrocarbon radical having from 16 to 22 carbon atoms and an iodine number of from 45 to 55 A process for preparing a quaternary ammonium salt mixture, comprising reacting the following materials at a temperature of 170 ° C. to 210 ° C., I) C ₁₂ -C ₂₂ substituted or unsubstituted fatty acids or fatty acid mixtures having more than 0% and less than 20% trans double bonds; And II) alkanolamines of the general formula: (Formula 1) (In Formula 1, R ₃ , R ₁ and R ₂ are independently selected from C ₂ -C ₄ hydroxyalkyl group.) The molar ratio of fatty acid to alkanolamine is 1.6 to 1.8, the reaction temperature is increased in the range of 70 to 170 ℃ to 210 ℃, the reaction temperature is 170 ℃ to 210 until the reaction product has an acid value of 5 or less Maintained in the range of &lt; RTI ID = 0.0 &gt; Obtaining an ester composition having; And Characterized in that it is quaternized with C ₁ -C ₃ straight or branched chain alkyl halides, phosphates, carbonates or sulfates, C ₇ -C ₁₀ aralkyl halides, phosphates or sulfates or mixtures thereof to obtain quaternary ammonium salt mixtures. Method for preparing quaternary ammonium salt mixture. The method of claim 9, The reaction temperature is a method for producing a quaternary ammonium salt mixture, characterized in that at a rate of 1.25 ℃ -3 ℃ per minute from the starting temperature of 70 ℃ to 170 ℃ to 210 ℃. The method of claim 9, Said fatty acid is a substituted or unsubstituted C ₁₆ -C ₂₂ fatty acid having an iodine number of 30 to 60. The method of claim 9, Wherein said fatty acid is a substituted or unsubstituted C ₁₆ -C ₂₂ fatty acid having an iodine number of 45 to 55. The method of claim 11, The fatty acid is a method of producing a quaternary ammonium salt mixture, characterized in that derived from tallow, soybeans, palm, palm kernel, rapeseed, pig oil, or mixtures thereof. The method of claim 11, Wherein said fatty acid is derived from partially hydrogenated tallow, soybean, palm, palm kernel, rapeseed, pig oil or mixtures thereof. The method of claim 9, The alkanolamine is a method for producing a quaternary ammonium salt mixture, characterized in that selected from the group consisting of triethanolamine, propanol diethanolamine, ethanol diisopropanolamine, triisopropanol amine and mixtures thereof. The method of claim 9, Wherein the molar ratio of fatty acid to alkanol amine is 1.7. The method of claim 9, Wherein said fatty acid has a trans isomer of less than 10%. The method of claim 9, The alkylating agent is selected from the group consisting of methyl chloride, benzyl chloride, diethyl sulfate, dimethyl carbonate, trimethyl phosphate, dimethyl sulfate or mixtures thereof. The method of claim 9, A process for preparing a quaternary ammonium salt mixture, characterized in that no solvent is used during quaternization. The method of claim 9, A process for preparing a quaternary ammonium salt mixture, characterized in that a solvent is used during quaternization. The method of claim 20, The solvent is selected from the group consisting of C ₁ -C ₆ alcohols, glycols, fatty acids, monoglycerides, diglycerides or triglycerides and mixtures thereof. A quaternary ammonium salt mixture comprising a monoester component, a diester component and a triester component, The quaternary ammonium salt mixture comprises at least 55% diester component and less than 25% triester component, and The quaternary ammonium salt mixture is quaternary ammonium salt mixture, characterized in that the reaction product of the following components: A) is a reaction product of substituted or unsubstituted C ₁₂ -C ₂₂ fatty acids having a trans double bond of less than 20% with a trialkanolamine of the formula (I), wherein the molar ratio of fatty acids: trialkanolamine is 1.6-1.8 Phosphorus esters; And (Formula 1) (In Formula 1, R ₃ , R ₁ and R ₂ are independently selected from C ₂ -C ₄ hydroxyalkyl group.) B) an alkylating agent selected from C ₁ -C ₃ straight or branched chain alkyl halides, phosphates, carbonates or sulfates, C ₇ -C ₁₀ aralkyl halides, phosphates or sulfates or mixtures thereof. The method of claim 22, The fatty acid is a quaternary ammonium salt mixture, characterized in that derived from tallow, soybeans, palm, palm kernels, rapeseed, pig oil and mixtures thereof. The method of claim 23, The fatty acid is quaternary ammonium salt mixture, characterized in that derived from partially cured tallow, soybeans, palms, palm kernels, rapeseeds, pig oil and mixtures thereof. The method of claim 22, The alkanolamine is quaternary ammonium salt mixture, characterized in that selected from the group consisting of triethanolamine, propanol diethanolamine, ethanol diisopropanolamine, triisopropanol amine and mixtures thereof. The method of claim 22, Said alkylating agent is selected from the group consisting of methyl chloride, diethyl sulfate, benzyl chloride, trimethyl phosphate, dimethyl carbonate, dimethyl sulfate or mixtures thereof. The method of claim 22, The quaternary ammonium salt mixture, characterized in that the molar ratio of the fatty acid and the alkanolamine is 1.7. (Twice correction) The method of claim 22, A quaternary ammonium salt mixture, characterized in that it comprises at least 60 wt% and up to 100 wt% diester component and more than 0 wt% and less than 15 wt% triester component. A quaternary ammonium salt mixture comprising a monoester component of formula (2), a diester component of formula (3) and a triester component of formula (4), derived from the reaction of fatty acids with alkanolamines, (Formula 2) (Formula 3) (Formula 4) (In Formula 2, 3, 4, R represents a hydrocarbon radical having 12-22 carbon atoms, wherein R ₁ ', R ₂ ', and R ₃ 'are independently selected from C ₂ -C ₄ alkyl group, R ₄ ′ is C ₁ -C ₃ straight or branched chain alkyl or C ₇ -C ₁₀ aralkyl) The diester component (Formula 3) is contained in more than 60% by weight 100% by weight based on the total amount of the quaternary ammonium salt mixture, the triester component (Formula 4) is contained more than 0% by weight less than 25% by weight A quaternary ammonium salt mixture. A fabric softening method comprising the step of adding a softening effective amount of the softener composition of claim 1 to a fabric. A method of softening, conditioning, or lubricating or conditioning hair or skin, comprising applying to the hair or skin an effective amount of the quaternary ammonium salt mixture of claim 22, thereby softening, conditioning and lubricating. The method of claim 9, The reaction temperature is a method for producing a quaternary ammonium salt mixture, characterized in that maintained for 20 minutes in the range of 170 ℃ to 210 ℃.