CN1293086C - Fabric softening compositio - Google Patents

Abstract

A fabric softening composition is provided which does not affect the hygroscopicity of the fabric. The softener contains: (1) a liquid or soft solid derivative (CPE) of a cyclic polyol or a liquid or soft solid derivative (RSE) of a reducing sugar, which is composed of a cyclic polyol or a reduced The 35-100% hydroxyl group of sugar is obtained by esterification or etherification, and the derivative (CPE or RSE) contains at least 2 or more esters connected to _C8-22 alkyl or alkenyl chains or their mixed chains group or ether group, and contain at least 35% triester or higher ester; (2) deposition aids. Also provided are liquid or soft solid glucose fatty acid esters containing C ₂ -C ₂₂ alkyl or alkenyl compounds, which are obtained from the above-mentioned cyclic polyols.

Description

fabric softening composition

                                   

The present invention relates to fabric softening compositions. In particular, the present invention relates to compositions which soften fabrics without affecting the absorbency of the fabrics.

Background technique

Rinse added fabric softening compositions are known. However, conventional rinse conditioners have the disadvantage that although they increase the soft feel of fabrics, they simultaneously reduce the hygroscopicity of fabrics. Decreasing the hygroscopicity of a fabric means its ability to absorb moisture is reduced. This is especially detrimental to towels, as users demand softness but also high moisture absorption.

Co-pending application GB 9518012.1 (Unilever) discloses a liquid fabric conditioning composition comprising a substantially water-insoluble fabric softening compound. The phase structure of the composition was shown by X-ray crystallography to be larger than the unidirectional long-range rule. The composition has good softening properties and hydrophobicity.

EP 0380406 (Colgate-Palmolive) discloses detergents containing sugars or reducing sugar esters containing at least one fatty acid chain.

WO 91/10719 (Novo) discloses detergent compositions containing pentose and hexose derivatives containing long-chain acyl or aroyl groups, and one or more glycosidic bonds linked to long-chain Linked short-chain alkyl groups.

Fabric treatment compositions containing mixtures of cationic and nonionic surfactants are disclosed in GB 1601359 (Procter & Gamble).

US 4800038 (Colgate-Palmolive) discloses the use of acylated sugar ethers as bleach activators in nonionic detergent compositions.

WO 9500614 (Kao Corporation) discloses softening compositions containing polyol esters and cationized cellulose.

JP 06264049 (Mitsubishi Kasei Corporation) discloses sucrose long-chain fatty acid esters with improved viscosity contained in cosmetic and topical skin care compositions with an average degree of substitution of 4-7.

Aqueous fabric softeners containing nonionic surfactants and certain mono-, di- or tri-fatty acid esters of polyols are disclosed in US 5447643 (Hüls).

Fabric softeners are disclosed in WO 96/15213 (Henkel), which contain carbohydrate derivatives containing alkyl, alkenyl and/or acyl groups, which are solidified through esterification, and the softener Also contains nonionic and cationic emulsifiers.

JP 08 158258 (Kao) discloses antimicrobial fabric softening compositions containing polyhydric alcohol fatty acid esters. Fabric softeners containing _C10 - _C26 mono- and diesters are disclosed in BE 827986 (P&G).

The present invention aims at how to alleviate the above-mentioned problems in the prior art.

The main advantage of the present invention is that the composition of the present invention effectively softens fabrics without compromising the hygroscopicity of fabrics, and the composition is easy to prepare.

Invention Summary

One aspect of the invention provides:

A fabric softening composition comprising:

(1) A liquid or soft solid derivative of cyclic polyol (CPE) or reducing sugar (RSE), said derivative is esterified or etherified by 35-100% hydroxyl of cyclic polyol or reducing sugar Obtained, the derivative (CPE or RSE) contains at least 2 or more ester groups or ether groups connected to C _8-22 alkyl or alkenyl chains or their mixed chains respectively, and also contains at least 35% triester or higher esters; and

(2) Deposition aids.

In another aspect, the present invention also provides:

A fabric softening composition comprising:

(1) Liquid or soft solid derivatives of cyclic polyols or liquid or soft solid derivatives of reducing sugars, which are obtained by esterification or etherification of 35-100% hydroxyl groups of cyclic polyols or reducing sugars Yes, the derivative contains at least 2 or more ester groups or ether groups respectively connected to _C8-22 alkyl or alkenyl chains or mixed chains thereof, including at least 35% triesters or higher esters, and derived from disaccharide;

(2) Deposition aids selected from cationic surfactants, nonionic surfactants, anionic surfactant compositions, polymeric deposition aids, fabric softening compounds or mixtures thereof.

Preferably, the liquid or soft solid derivatives are obtained by etherification or esterification of 4 or more hydroxyl groups of cyclic polyols or reducing sugars;

Preferably, wherein said liquid or soft solid derivative is sugar polyester, sugar polyether or sugar polyester/polyether; further, said liquid or soft solid derivative is selected from sucrose pentalaurate, sucrose Tetraoleate, Sucrose Pentaerucate, and Sucrose Tetraerucate.

The present invention also relates to a method for conditioning a fabric, comprising conditioning the fabric with a composition containing CPE or RSE, wherein the CPE or RSE is a liquid or a soft solid, and the ratio between the solid and the liquid at 20°C is measured by nuclear magnetic resonance _T2 relaxation time The ratio is 50:50 to 0:100.

The present invention also discloses the use of CPE or RSE as fabric softening aids which do not reduce the hygroscopicity of the fabric.

The present invention also relates to liquid or soft solid glucose fatty acid esters, whose solid: liquid ratio is 50:50 to 0:100 as measured by the above-mentioned determination method, with C ₂ -C ₂₂ alkyl or alkenyl chains The ester group of the mixture, the fatty acid ester is obtained by esterifying 35-100% of the hydroxyl groups of the cyclic polyol. Also provided is the use of sorbitan monooleate, dioleate or trioleate as a hydrophilic softener. Surprisingly, the above compositions have been found to soften fabrics while maintaining their original absorbency.

                      Invention Details

In the context of the present invention, capital letters CPE or RSE respectively represent cyclic polyol derivatives or reducing sugar derivatives, which are obtained through esterification and/or etherification of 35-100% hydroxyl groups of cyclic polyols or reducing sugars, wherein at least Two or more ester groups or ether groups each connected to a C _8-22 alkyl or alkenyl chain.

In the fabric softener compositions of the present invention, the ratio of CPE or RSE to deposition aid is preferably from 1:10 to 15:1, more preferably from 1:5 to 10:1, most preferably from 1:1 to 10:1.

A CPE or RSE to deposition ratio of at least 1:1 is preferred if the composition is required to render fabrics highly absorbent (especially when the deposition aid itself is a fabric softening compound).

When a highly softening composition is desired, the ratio of deposition aid to CPE or RSE is 2:3, preferably 1:1.

For fabrics with excellent softening and hydrophobic properties, the preferred ratio of softening deposition aid to CPE or RSE is 3:2 ester 1:10, more preferably 2:3 to 1:10.

CPE or RSE

The liquid or soft solid (as defined above) CPE or RSE of the present invention is obtained by esterification and/or etherification of 35-100% hydroxyl groups of cyclic polyols or reducing sugar raw materials. CPE or RSE generally contains 3 or more ester or ether groups or mixtures thereof, for example 4 or more, or 5 or more. Preferably, 2 or more ester groups or ether groups are respectively connected to C _8-22 alkyl or alkenyl groups, and the alkyl or alkenyl groups may be straight chain or branched.

Preferably 40-100% of the hydroxyl groups, most preferably 50-100% of the hydroxyl groups are esterified or etherified.

CPE is preferred for use in the present invention. Inositol is a preferred example of cyclic polyol. Inositol derivatives are particularly preferred.

The term "cyclic polyols" in the context of the present invention includes all forms of sugars. Indeed carbohydrates are particularly preferred for use in the present invention. CPE or RSE preferably have sugars derived from monosaccharides and disaccharides.

Examples of monosaccharides include xylose, arabinose, galactose, fructose, sorbose and glucose. Glucose is particularly preferred.

An example of a reducing sugar is sorbitan.

Examples of disaccharides include maltose, lactose, cellobiose and sucrose. Sucrose is particularly preferred.

The liquid or soft solid CPE or RSE of the present invention can be prepared by various methods known to those skilled in the art. These methods include acylation of cyclic polyols or reducing sugars with acid chlorides; transesterification of cyclic polyols or reducing sugar fatty acid esters with various catalysts; acylation of cyclic polyols or reducing sugars with acid anhydrides; Fatty acids acylate cyclic polyols or reducing sugars. General preparations of these materials are disclosed in US 4386213 (Procter and Gamble) and AU 14416/88 (Procter and Gamble).

Preferably, CPE or RSE contains 4 or more ester groups or ether groups. Of course, sometimes some of these compounds contain 3 ester groups or ether groups to produce excellent results. At this time, it is preferred to contain 3 ester groups or ether groups. Ether based. If the cyclic CPE is a disaccharide, preferably the disaccharide contains 4 or more ester or ether groups. Particularly preferred CPEs are esters with a degree of esterification of 4 or more, such as sucrose esters.

It is advantageous if the sugar or reducing sugar contains 3 or more ester groups.

Where the cyclic polyol is a reducing sugar, each ring of the CPE suitably contains one ether group, preferably at the _C1 position, while the remaining hydroxyl groups are esterified. Examples of suitable compounds of this type include methyl glucose derivatives.

Examples of suitable CPEs include alkyl (poly)glucoside esters, especially alkyl glucoside esters having a degree of polymerization of 1-2.

It is preferred that the ester or ether groups of cyclic polyols or reducing sugars are respectively connected to linear or branched alkyl or alkenyl chains, or to C ₂ -C ₈ chains, wherein C ₈ -C ₂₂ chains are connected to C ₂ - The ratio of C _chains is 5:3 to 3:5. This is because in this case these products are mainly oily (liquid) and thus easy to formulate. It has also been found that excellent results can be achieved from this oily (liquid) product.

Examples of suitable sugar esters include fatty acid esters of glucose, the ester group having a C ₂ -C ₁₈ alkyl or alkenyl chain, the degree of esterification being 5. In specific sugars mainly containing C ₂ alkyl chains and C ₈ -C ₁₂ straight chain alkyl chain ester groups, the molar ratio of short chain C ₂ alkyl groups to C ₈ -C ₁₂ straight chain alkyl groups is 2:1 to 1:2, more preferably about 1:1. More preferably the degree of esterification is at least 5.

The liquid or soft solid (as defined above)-like CPE or RSE material of the present invention is characterized in that the solid at 20°C is measured by the NMR _T2 relaxation time: the liquid ratio is 50:50 to 0:100, preferably 43:57 to 0:100, most preferably 40:60 to 0:100, such as 20:80 to 0:100. The _T2 NMR relaxation time is often used to characterize the ratio of solid to liquid in soft solid products such as fats and margarines. For the present invention, the components whose relaxation time T ₂ of the nuclear magnetic resonance signal is less than 100 μs are considered as solid components, and the components with T ₂ ≥ 100 μs are considered as liquid components.

The prefixes four-, five- for CPE and RSE represent only the average degree of esterification. The compounds present in the feed mixture range from monomeric to fully esterified esters. The present invention uses the average degree of esterification to define CPE and RSE.

CPEs and RSEs containing unsaturated or mixed alkyl chain lengths were found to work well.

The factors that determine the applicability of CPE and RSE are the presence and degree of branching, mixed chain length and degree of unsaturation.

deposition aid

In the context of the present invention, a deposition aid means any substance which facilitates the deposition of selected CPEs and RSEs on the surface of fabrics during the laundering process.

The deposition aid may be selected from fabric softening compounds, cationic compounds, nonionic surfactants, anionic surfactants, polymeric deposition aids or mixtures thereof.

Preferably the deposition aid is cationic. Cationic polymeric deposition aids are preferred if no cationic surfactants or cationic softeners are employed in the composition. Most preferably the deposition aid is cationic and is a fabric softening compound.

Mixtures of deposition aids may be used, such as mixtures of cationic and nonionic surfactants, or mixtures of fabric softeners and polymeric deposition aids.

Suitable cationic deposition aids include water-soluble single chain quaternary ammonium compounds such as cetyltrimethylammonium chloride, cetyltrimethylammonium bromide, or the compounds disclosed in European Patent 258923 (Akzo).

Preferably, however, the deposition aid is a fabric softening compound. In particular, substantially water-insoluble quaternary ammonium materials containing mono-chain alkyl or alkenyl groups with an average chain length preferably greater than or equal to _C20 are preferred. More preferred are compounds containing polar end groups and two alkyl or alkenyl chains, wherein the average chain length of the alkyl or alkenyl chains is greater than or equal to _C14 .

Preferably, the fabric softening deposition aids of the present invention contain two long chain alkyl or alkenyl groups with an average chain length greater than or equal to _C14 . More preferably, the average chain length of each chain is greater than C ₁₆ . Most preferably at least 50% of each alkyl or alkenyl chain length is _C18 .

Preferably the long chain alkyl or alkenyl groups in the fabric softening deposition aid are predominantly linear.

Molecules of fabric softening deposition aids suitable for use in the compositions of the present invention have excellent softening properties and are characterized by chain melting Lβ to Lα transition temperatures above 25°C, preferably above 35°C, most preferably above 45°C. The transition temperature of Lβ to Lα can be determined by differential scanning calorimetry (DSC) as defined in "Handbook of Lipid Bilayers, D Marsh, Published by CRC, Boca Raton Florida, 1990 (pp. 137-337)".

"Essentially water-insoluble" textile compound in the context of the present invention means that its solubility in demineralized water is less than 1 x ^10-3 % by weight at 20°C. Preferably the solubility of the fabric softening deposition aid is less than 1 x ^10-4 % by weight. Most preferably the fabric softening deposition aid has a solubility in demineralized water of 1 x 10 ^-8 to 1 x 10 ^-6 at 20°C.

Preferred fabric softening deposition aids are quaternary ammonium compounds, preferably containing at least one ester linkage.

Particularly preferred fabric softening deposition aids are water insoluble quaternary ammonium materials containing compounds bearing two _C12-18 alkyl or alkenyl groups attached to the molecule by at least one ester bond. More preferably the quaternary ammonium material contains two ester linkages. A particularly preferred ester bond-containing quaternary ammonium substance suitable for use in the present invention can be represented by the following formula (I):

式(I)

Formula (I)

Wherein each R ¹ group is independently selected from C _1-4 alkyl, hydroxyalkyl or C _2-4 alkenyl; wherein each R ² group is independently selected from C _8-28 alkyl or alkenyl;

T is

X- is any suitable anion, and n is an integer from 0-5.

Particular preference is given to bis(tallowyloxyethyl)dimethylammonium chloride.

Another preferred quaternary ammonium substance can be represented by the following formula (II):

式(II)

Formula (II)

wherein R ¹ , n, X- and R ² are as defined above.

For environmental protection considerations, the quaternary ammonium substance should be biodegradable.

Preferred materials of this type such as 1,2-bis[hardened tallow acyloxy]-3-trimethylpropaneammonium chloride and methods for their preparation are described in US Patent 4,137,180 (Lever Brothers) and others. These materials preferably contain small amounts of the corresponding monoesters described in US Patent 4,137,180, such as 1-hardened tallowyloxy-2-hydroxy 3-trimethylpropaneammonium chloride.

The fabric softening deposition aid in the composition may also be a compound represented by the following formula (III):

Formula (III)

Where X is an anion, and A is the remaining (m+n) valent group after removing (m+n) hydroxyl groups from the aliphatic polyol, which contains p hydroxyl groups, and the distance between its carbon atom and oxygen atom having a ratio of 1.0-3.0, further containing a group selected from ethylene oxide and propylene oxide, with respect to each hydroxyl group, the group is at most two,

m is 0 or an integer from 1 to p-n, n is an integer from 1 to p-m, and p is an integer of at least 2,

B is an alkylene or alkylidene having 1 to 4 carbon atoms.

R ³ , R ⁴ , R ⁵ and R ⁶ are independently of each other linear or branched C ₁ -C ₄₈ alkyl or alkenyl, which may or may not be substituted by one or more functional groups, and/or are substituted by up to 10 units The ethylene oxide and/or propylene oxide is interrupted, or interrupted by up to 2 functional groups selected from the following formulae:

Or ^R11 and ^R12 may form a ring system containing 5 or 6 atoms, provided that the compound contains on average at least one R group with 22-48 carbon atoms, or at least two R groups with 16-20 carbon atoms Atomic R groups, or at least 3 R groups with 10-14 carbon atoms. Preferred compounds of this type are described in EP 638 639 (Akzo).

Deposition aids can also be nonionic surfactants. Preferred nonionic ethoxylated surfactants have an HLB of about 10-20. The alkyl group of the surfactant preferably contains at least 12 carbon atoms.

Polymeric deposition aids suitable for use in the present invention include cationic and nonionic polymeric deposition aids.

Suitable cationic polymeric deposition aids include cationic guar polymers such as Jaguar (from Rhone Poulenc), cationic cellulose derivatives such as Celquats (from National Starch), Flocaid (from National Starch), cationic potato starches such as SoftGel (from Aralose) , cationic polyacrylamide such as PCG (produced by Allied Colloids). Preferred compositions employ cationic polymerization aids in the absence of other cationic materials.

Suitable nonionic deposition aids include Pluronics (from BASF), dialkyl PEGs, cellulose derivatives as described in UK Patent Application 213730 (Unilever), hydroxyethylcellulose, starch and hydrophobically modified nonionic polyols Such as Acusol 880/882 (produced by Rohn & Haas).

Various mixtures of the above deposition aids may be employed.

pH of the composition

The pH of the fabrics of the present invention is preferably 1.5-7, more preferably 1.5-5.

other ingredients

Fatty acids such as C ₈ -C ₂₄ alkyl or alkenyl monocarboxylic acids, or polymeric carboxylic acids, preferably saturated fatty acids, especially hardened tallow C ₁₆ -C ₁₈ fatty acids, may also be present in the compositions of the invention.

The composition may also contain one or more optional ingredients selected from the group consisting of electrolytes, non-aqueous solvents, pH buffers, fragrances, fragrance carriers, fluorescers, colorants, hydrotropes, defoamers, anti-soil re- Sedimentants, polymeric thickeners and other thickeners, enzymes, optical brighteners, opacifiers, anti-shrinkage agents, anti-wrinkle agents, anti-staining agents, bactericides, anti-fungal agents, antioxidants, anti-corrosion agents, Agents for imparting drape to fabrics, antistatic agents, sunscreens, color protectants and ironing aids.

If the product is liquid, it is suitable to add a viscosity modifier. Viscosity modifiers that can be used in conjunction with rinse conditioners are suitable for use herein, such as biopolymers such as xanthan gum (Kelco by Kelsan and Rhodopol by Rhone-Poulenc), guar gum (Rhodopol by Rhone-Poulenc ), starch and cellulose ethers. Synthetic polymers are also suitable viscosity modifiers, such as polyacrylic acid, polyvinylpyrrolidone, polyethylene, carbomer, cross-linked acrylamides such as Acosol 880/882 polyethylene, and polyethylene glycols.

Decoupling polymers and deflocculating polymers are also suitable viscosity modifiers.

Product dosage form

The composition may be in any physical form commonly used in fabric softening compositions, such as powders, pastes, gels or liquids. Preferably the product is a liquid, and particularly preferably it is an emulsion.

Example

The invention is illustrated by the following non-limiting examples. Other embodiments suitable within the scope of the present invention will also be apparent to those of ordinary skill in the art.

A. Preparation of CPE and RSE

Compound 1

Glucopentaester was prepared in which 50% (approximately) of the ester groups were acetyl and 50% (approximately) decanoyl.

α-D Glucose (0-111M) was added to pyridine at room temperature. Acetyl chloride (0.254M) and decanoyl chloride (0.278M) were mixed, and the acid chloride mixture was added dropwise to the glucose solution, and the acid chloride was added slowly over about 1.5 hours. During the course of the reaction, a large amount of white turbid precipitate was formed, and ethyl acetate was added to maintain the fluidity of the reaction mixture.

The reaction mixture was stirred overnight (>16 hours) at room temperature. The reaction mixture was filtered to remove solid pyridine hydrochloride and excess pyridine was removed under reduced pressure. The remaining product was taken up in ethyl acetate and mixed with water via a separatory funnel. The mixture was shaken and the layers were separated.

The organic layer was washed with water, diluted hydrochloric acid (to remove remaining pyridine), saturated sodium bicarbonate (to remove remaining carboxylic acid), water (twice) and saturated sodium chloride, respectively. The organic layer was dried overnight over magnesium sulfate (anhydrous), filtered and stripped with heat under high vacuum to leave a beige oily residue.

Infrared spectrum shows that the product only has a sharp single peak at 1749cm ^-1 in the carbonyl region. This confirms that no fatty acid chlorides or fatty acids are present in the product. In addition, there is no intensity caused by unreacted hydroxyl groups in the region of 3000-3500 cm ^-1 .

Analysis by ¹ H NMR spectroscopy gave a α:β anomer ratio of 34:66. Integration gave a ratio of cyclic protons (3.5-6.5 ppm) to alkyl chain protons (0.8-2.5 ppm) of 0.127. This is consistent with the theoretical value of 0.127 obtained by esterification of glucose molecules with an average of 2.5 acetyl groups and 2.5 decanoyl groups per ring.

Hydroxyl value 8.5

Density 1.0300g/ ^cm3

Viscosity 810mPa·s

Compound 2

Glucopentaester is prepared in which 50% (approximately) of the ester groups are acetyl and 50% (approximately) are lauryl.

The same procedure was used for the preparation of compound 1, substituting dodecanoyl chloride for decanoyl chloride.

Infrared spectrum shows that the product only has a sharp single peak at 1748cm ^-1 in the carbonyl region. This confirms that no fatty acid chlorides or fatty acids are present in the product. In addition, there is no intensity caused by unreacted hydroxyl groups in the region of 3000-3500 cm ^-1 .

Analysis by ¹ H NMR spectroscopy gave a α:β anomer ratio of 67:33. Integration gave a ratio of cyclic protons (3.5-6.5 ppm) to alkyl chain protons (0.8-2.5 ppm) of 0.1039. This is consistent with the theoretical value of 0.1076 obtained by esterifying glucose molecules with an average of 2.5 acetyl groups and 2.5 dodecanoyl groups per ring.

Hydroxyl value 19.5

Density 1.0078g/ ^cm3

Viscosity 693mPa·s

Compound 3

Glucopentaester is prepared in which 50% (approximately) of the ester groups are acetyl and 50% (approximately) are octanoyl.

Using the same procedure for the preparation of compound 1, substituting octanoyl chloride for decanoyl chloride, a dark brown viscous oily liquid was obtained.

Infrared spectroscopy showed that the product only had a strong sharp peak at 1748 cm ^-1 in the carbonyl region and a much smaller peak at 1644 cm ^-1 . This confirms that no fatty acid chlorides or fatty acids are present in the product. In addition, there is no intensity caused by unreacted hydroxyl groups in the region of 3000-3500 cm ^-1 . Hydroxyl value not detected

Density 1.0535g/ ^cm3

Viscosity 3500mPa·s

Compound 4

Glucopentaester was prepared in which 70% (approximately) of the ester groups were acetyl and 30% (approximately) octanoyl.

Using the same method for the preparation of compound 1, using acetyl chloride (0.388m) and octanoyl chloride (0.156m) gave a dark brown viscous oily liquid.

Infrared spectroscopy showed that the product only had a strong sharp peak at 1749 cm ^-1 in the carbonyl region and a much smaller peak at 1673 cm ^-1 . This confirms that no fatty acid chlorides or fatty acids are present in the product. In addition, there is no intensity caused by unreacted hydroxyl groups in the region of 3000-3500 cm ^-1 .

Viscosity 11450mPa·s

Density 1.1034g/ ^cm3

Compound 5

Preparation of sucrose octaester in which all ester groups are oleate groups.

Oleic acid (0.40M) (90% technical grade) was mixed with dichloromethane in a large round bottom flask, to which was added oxalyl chloride (0.44M) in dichloromethane. The remaining dichloromethane and excess oxalyl chloride were removed by high vacuum extraction to obtain 120 g of oleoyl chloride.

To a mixture of pyridine, ethyl acetate and dimethylformamide was added sucrose (0.044M) via a separatory funnel. The oleoyl chloride prepared above was added dropwise to the mixture, and the mixture was stirred overnight at 80° C., and a small amount of 4-dimethylaminopyridine catalyst was used in the mixture.

The resulting dark brown transparent solution was extracted under vacuum, and then absorbed with ether. The organic layer was washed with water (2 times), diluted hydrochloric acid, saturated sodium bicarbonate, water (4 times) and saturated brine, and then the organic layer was dried over magnesium sulfate overnight. The magnesium sulfate was removed by filtration and the ether was removed by high vacuum to give a yellow oily liquid.

Infrared spectrum shows that the product only has a sharp peak at 1740cm ^-1 in the carbonyl region. This confirms that no fatty acid chlorides or fatty acids are present in the product.

Hydroxyl value not detected

Viscosity 568mPa·s

Density 0.9446g/ ^cm3

Compound 6

Preparation of cellobiose octaester in which all ester groups are oleate groups.

The same method was used for the preparation of compound 5, wherein cellobiose was used instead of sucrose. The minor changes in terms of steps are that the reaction solvent only contains pyridine and dimethylformamide, and the final reaction needs to be heated with activated carbon before drying with magnesium sulfate.

Infrared spectrum shows that the product only has a sharp peak at 1744cm ^-1 in the carbonyl region. This confirms that no fatty acid chlorides or fatty acids are present in the product.

Gel permeation chromatography showed only one strong signal. This means that almost all components are octaesters.

Hydroxyl value not detected

Viscosity 1040mPa·s

Density 0.9459g/ ^cm3

Compound 7

Methyl [alpha]-D-glucopyranoside tetraester was prepared in which 37.5% (approximately) of the ester groups were acetyl and 62.5% (approximately) were dodecanoyl.

The same method was used for the preparation of compound 2, wherein methyl α-D-glucopyranoside was used instead of glucose.

Infrared spectrum shows that the product only has a sharp single peak at 1747cm ^-1 in the carbonyl region, which confirms that the product does not contain fatty acid chlorides or fatty acids.

Hydroxyl: 1.5

Viscosity 225mPa·s

Density 0.9930g/ ^cm3

Compound 8

A phytate is prepared in which 50% (approximately) of the ester groups are acetyl and 50% (approximately) are lauryl.

The same method was used for the preparation of compound 2, wherein inositol was used instead of glucose.

Infrared spectrum shows that the product only has a strong single peak at 1755cm ^-1 in the carbonyl region, which confirms that the product does not contain fatty acid chlorides or fatty acids.

Hydroxyl: 0.04

Viscosity 20500Pa·s

Density 1.0227g/ ^cm3

B. Examples of compositions

The above compounds selected in Table 1 were placed in ethanol or acetone solution (0.9 g/l) and placed on the fabric so as to deposit 0.2% by weight of the compound on the fabric.

Table 1 Example Fabric Softening Actives solvent 1 Glucose perester 50:50 C ₂ :C ₁₀ compound 1 (oily liquid) ethanol 2 Glucose perester 50:50 C ₂ :C ₁₂ compound 2 (oily liquid) ethanol 3 Glucose perester 50:50 C ₂ :C ₈ compound 3 (oily liquid) ethanol 4 Sucrose octaoleate compound 5 (oily liquid) acetone 5 Sucrose pentaoleate (Ryoto 0-170) (oily liquid) acetone 6 Sucrose Pentaester (Ryoto POS-135 ^* ) (soft solid) acetone 7 Sucrose pentataurate (Ryoto L-195) (soft solid) acetone A Sucrose tetrastearate (Ryoto S-270) (white powder) ethyl acetate

^* Contains a mixture of palmitate, stearate and oleate groups.

The following components were mixed with water to prepare the compounds of Examples 8-21 (Table 2). All examples contain 5% active substance.

Table 2: Mixtures containing cetyltrimethylammonium chloride (CTAC) (fabric softening compositions) Example B 8 9 10 11 12 13 14 15 16 17 18 19 20 twenty one Cetyltrimethylammonium Chloride (CTAC) 1 3 2 1 3 2 1 1 1 1 1 1 1 1 1 Glucose perester 50:50 C ₂ :C ₁₂ compound 2 (oily liquid) 2 3 4 Glucose perester 50:50 C ₂ :C ₁₀ compound 1 (oily liquid) 2 3 4 Sucrose Pentaoleate (Ryoto 0-170) 4 Sucrose pentaester (Ryoto POS-135) 4 Sucrose Pentalaurate (Ryoto L-195) 4 Sucrose tetrastearate (Ryoto S-270) 4 Sucrose tetraoleate (oily liquid) 4 Sucrose Pentaerinate (Ryoto ER-190) (soft solid) 4 Sucrose tetraerucate (Ryoto ER-290) (soft solid) 4 Sorbitan Monooleate (Span 80) (oily liquid) 4 Sorbitan Trioleate (Span 85) (oily liquid) 4 water 95 95 95 95 95 95 95 95 95 95 95 95 95 95 95 CTAC:Oil Ratio 1:4 3:2 2:3 1:4 3:2 2:3 1:4 1:4 1:4 1:4 1:4 1:4 1:4 1:4 1:4

Span 80 and Span 85 are surfactants available from ICI.

CTAC was purchased from Aldrich (25% solution).

Ryoto products were purchased from Mitsibushi-Kagku Foods Corporation.

Heat each component together to 80°C and mix with high-speed stirring to prepare the compounds of each example in Table 3 below

Table 3: Blends containing HEQ (fabric softening compounds) Example twenty two twenty three twenty four 25 26 27 C 28 29 30 31 32 D. HEQ ¹ 2.57 1.71 0.86 2.57 1.71 0.86 4.28 0.86 0.86 0.86 2.57 1.71 0.86 fatty acid 0.43 0.39 0.14 0.43 0.29 0.14 0.72 0.14 0.14 0.14 0.43 0.39 0.14 Glucose perester 50:50 C ₂ :C ₁₂ compound 2 (oily liquid) 2 3 4 - - - - Glucose perester 50:50 C ₂ :C ₁₀ compound 1 (oily liquid) - - - 2 3 4 - Sucrose pentaoleate (Ryoto 0-170) (oily liquid) 4 2 3 Sucrose pentaester (Ryoto POS-135) (soft solid) 4 Sucrose Pentalaurate (Ryoto L-195) (Acidic Solid) 4 Sucrose tetrastearate (Ryoto S-270) (white powder) 4 water 95 95 95 95 95 95 95 95 95 95 95 95 95 HEQ: ratio of oil 1.285:1 1:1.45 1:4.65 1:13.75 1:1.75 1:4.65 - 1:4 1:4 1:4 3:2 2:3 -

HEQ ¹ is 1,2 bis(hardened tallowyloxy)-3-trimethylpropaneammonium chloride available from Hoechst.

Each component was heated to 80° C. and mixed with high-speed stirring to prepare the compounds of each example listed in Table 4.

Table 4: Mixtures containing Prapagen 34453

Each component was heated to 80° C. and mixed with high-speed stirring to prepare the compounds of each example listed in Table 4. Example 33 34 35 36 37 38 E. Prapagen 3445 ² 3 2 1 3 2 1 5 Glucose perester 50:50 C ₂ :C ₁₂ compound 2 (oily liquid) 2 3 4 - Glucose perester 50:50 C ₂ :C ₁₀ compound 1 (oily liquid) - - - 2 3 4 - water 95 95 95 95 95 95 95 Prapagen: oil ratio 3:2 2:3 1:4 3:2 2:3 1:4

² Dimethyl ditallow ammonium chloride.

Table 5: Mixtures containing Accosoft 460 HC

Each component was heated to 80°C and mixed with high-speed stirring to prepare each component listed in Tables 5, 6 and 7.

Example compounds. Example 39 40 41 f Accosoft 460HC 3 2 1 5 Sucrose pentaoleate Ryoto 0-170 (oily liquid) 2 3 4 0 water 95 95 95 95 Accosoft: Oil Ratio 3:2 2:3 1:4 -

Table 6: Mixtures containing Accosoft 550 HC Example 42 43 44 G Accosoft 550HC 3 2 1 5 Sucrose pentaoleate Ryoto 0-170 (oily liquid) 2 3 4 0 water 95 95 95 95 Accosoft: Oil Ratio 3:2 2:3 1:4 -

Accosoft 460 and Accosoft 550 HC were purchased from Stepan.

Table 7: Mixtures containing Arquad HT Example 45 46 47 Arquad HT 1 1 1 Sucrose tetraoleate (oily liquid) 4 Sucrose pentaerucate (Ryoto ER-190) (oily liquid) 4 Sucrose tetraerucate (Ryoto ER-290) (oily liquid) 4 water 95 95 95 Arquad HT: Oil Ratio 1:4 1:4 1:4

Evaluation of softening

The softening properties were assessed by adding 0.1 g of fabric softening compound (2 ml of a 5% active liquid dispersion) to 1 liter of tap water in a tergotometer at room temperature. Three terry towels (8 cm x 8 cm, weighing 40 grams) were added to the tergotometer jar. The fabric was treated at 65 rpm for 5 minutes, wrung to remove excess solution, aired overnight and conditioned at 21°C/65°C for 24 hours.

Terry towels were treated with the compounds of Examples 1-7 and A, and the compositions were placed directly on the fabric.

Fabric softening was evaluated by a panel of 4 experts using a round robin paired comparison test protocol. Each panel member evaluates four sets of tested fabrics. Each set of fabrics tested includes one piece of fabric from each test system evaluated. The panelists were asked to rate softening using 8 scales. Softening values were calculated using the "Analysis of Variance" method. Lower values indicate better softening properties.

Hygroscopicity Assessment

Hygroscopicity is determined using the wicking (Klemm) test in the textile and paper industry. A piece of fabric to be tested is hung with clips, and the hanging free end is weighted with a piece of rubber. Drape the cloth strip down into the pan containing the 0.02% diphenyl red dye solution with the weighted rubber just below the surface of the water. Measure the height of the liquid on the strip after 1 hour (unless otherwise stated). Six strips of cloth were measured for each treatment. The active ingredients in Table 8 are deposition aids.

Table 8

Example Oil active ingredient Moisture absorption height (cm) softening value 14 Ryoto 0-170 CTAC 15.88 3.07 15 Ryoto POS-135 CTAC 8.82 3.05 16 Ryoto L-195 CTAC 7.18 3.57 17 Sucrose Tetraoleate CTAC 14.04 4.00 18 Ryoto ER-190 CTAC 15.21 3.90 19 Ryoto ER-290 CTAC 13.35 3.75 20 Span 80 CTAC 13.43 4.56 twenty one Span 85 CTAC 13.70 4.25 B Ryoto S-170 CTAC 6.33 3.17 twenty two Compound 2 HEQ 5.33 2.67 twenty three Compound 2 HEQ 8.50 2.70 twenty four Compound 2 HEQ 11.59 3.29 25 Compound 2 HEQ 3.12 3.325 26 Compound 2 HEQ 5.79 3.875 27 Compound 2 HEQ 11.79 4.75 28 Ryoto 0-170 HEQ 11.04 3.08 29 Ryoto POS-135 HEQ 9.41 4.50 30 Ryoto L-195 HEQ 9.95 4.25 31 Ryoto 0-170 HEQ 8.19 2.31 32 Ryoto 0-170 HEQ 9.89 2.65 C - HEQ 2.20 2.5 D Ryoto S-270 HEQ 6.25 3.75 33 Compound 2 Prapagen 3445 11.25 4.12 34 Compound 2 Prapagen 3445 11.83 4.87 35 Compound 2 Prapagen 3445 13.08 4.87 36 Compound 1 Prapagen 3445 13.21 4.37 37 Compound 1 Prapagen 3445 13.75 4.75 38 Compound 1 Prapagen 3445 15.12 4.625

Example Oil active ingredient Moisture absorption height (cm) softening value E - Prapagen 34452 12.71 5.38 39 Ryoto 0-170 Accosoft 460HC 6.78 3.67 40 Ryoto 0-170 Accosoft 460HC 9.3 3.5 41 Ryoto 0-170 Accosoft 460HC 13.01 3.87 F Ryoto 0-170 Accosoft 460HC 3.34 4.17 42 Ryoto 0-170 Accosoft 550HC 10.97 3.92 43 Ryoto 0-170 Accosoft 550HC 12.76 3.8 44 Ryoto 0-170 Accosoft 550HC 15.23 4.17 G Ryoto 0-170 Accosoft 550HC 9.9 5.15 45 Sucrose Tetraoleate Arquad HT 14.00 3.94 46 Ryoto ER-190 Arquad HT 14.73 4.25 47 Ryoto ER-290 Arquad HT 13.58 4.00 desized towels 20.00 8.0

仅经30分钟后测定出的吸湿高度

Moisture absorption height measured after only 30 minutes

The aforementioned softening and hygroscopic effects indicate that the tested compounds have superior hydrophilic softening properties compared to prior art compounds.

Examples 48 and 49

Examples 48 and 49 Prepare aqueous emulsions/dispersions containing 5% active ingredient containing a mixture of fabric softener and sucrose ester in a ratio of 1:4. 0.3% fragrance was added to the composition and the persistence of the fragrance was determined. See Table 11 below.

Table 11 Example fabric softener Sucrose esters essence moisturizing oil 5 hours 24 hours 48 CTAC Sucrose Pentaoleate (Ryoto 0-170) Liquid suitable suitable suitable 49 HEQ Sucrose pentastearate above 3.0 2.4 1.76 h HEQ - 3.1 1.9 1.19

Fragrance intensity was measured by a trained panel, with Example 48 being measured alone. The fabrics were scored on a scale of 0-5. 5 being extremely strong scent and 0 being no perceptible scent. Perfume concentration was evaluated immediately after application (when the fabric was wet), 5 hours and 24 hours after application.

It can be seen that the presence of oil can increase the retention time of fragrance.

Example 50

A series of emulsions/dispersions in water were prepared in Example 50 containing 5% active ingredient 4.5% sucrose tetraerucate (oily liquid, Ryoto ER 290), 0.5% CTAC and 0.2% Polymeric deposition aids (some are cationic):

Example 50a Celquat SC240 (available from National Starch & Chemical)

Example 50b Coltide HQS (available from Croda Coloids)

Example 50c Crodacel QS (purchased from Croda Coloids)

Example 50d FlocAid 34 (available from National Starch)

Example 50e Bermacoll CST 035 (available from Berol Nobel) Nonionic

Example 50f Merquat 100 (available from Chemviron)

Embodiment 50g Softgel BDA (purchased from Avebe)

Example 51

A series of water emulsions/dispersions containing 5% active ingredient were prepared in Example 51, containing 4.5% sucrose tetraerucate (same as Example 50) in the active ingredient, 0.5% nonionic surfactant deposition aid ( Synperonic A7) and less than 0.2% of deflocculant polymers (both cationic):

Example 51a Celquat SC240 (available from National Starch & Chemical)

Example 51b Coltide HQS (available from Croda Colloids)

Example 51c Coltide QS (available from Croda Colloids)

Example 51d Poly Poly DMDAAC: EHA (purchased from National Starch)-10:1

Molar ratio copolymer (molecular weight is about 2400)

Example 52

A 1:4 emulsion/dispersion (5% active ingredient) of DEEDMAC to sucrose pentaoleate (Ryoto 0-170) was prepared by mixing Example 52 at elevated temperature.

Softness and hygroscopicity were evaluated as described above. The composition was stable and was evaluated as follows:

Softening 4.00

Moisture absorption height: 11.74cm

Example 53

Fully formulated fabric softening compositions of the present invention are prepared from the following ingredients.

% by weight

Cetyltrimethylammonium Chloride 1.0

Sucrose Ester Oil 4.0

Cationic polymerization deposition aid 0.2

Dye 0.0025

Fragrance 0.3

Trace ingredients 0.02

Water balance

Sucrose ester was Ryoto ER290 from Mitsubishi Kagaku Foods. The deposition aid was Floc Aid 34 from National Starch & Chemical.

Example 54

Table 9 below shows the solid to liquid ratio of the CPE and RSE used in the present invention as measured by _T2 NMR. A control group of crystalline solid sugar esters was also included. The ratio is measured at 20°C. The degree of esterification/etherification is listed. materials Solid: liquid ratio at 20°C Degree of Esterification and Percentage of Esterification physical form Ryoto S270 (control) 96:4 4/8 50% crystalline solid liquid Ryoto 0-170 0:100 5/8 62.5% liquid Ryoto ER-290 0:100 4/8 50% liquid Ryoto ER-190 0:100 5/8 50% soft solid Ryoto POS-135 30:70 5/8 62.5% soft solid Ryoto L-195 43:57 5/8 62.5% liquid Sucrose Tetraoleate 0:100 4/8 50% liquid Compound 1 Oleate 0:100 5/5 100% liquid Compound 2 0:100 5/5 100% liquid Compound 3 0:100 5/5 100% liquid Compound 4 0:100 5/5 100% liquid Compound 5 0:100 8/8 100% liquid Compound 6 0:100 8/8 100% liquid Compound 7 0:100 4/4 100% liquid Compound 8 0:100 6/6 100% liquid Span 80 0:100 1/4 25% liquid Span 85 0:100 3/4 75% liquid

The ingredients of Ryoto are mentioned above. Compounds 1-8 are described above. Span 80 and 85 are sorbitan oleate and trioleate oily liquid surfactants, respectively, available from ICI.

Claims (10)

1. fabric softening compositions, wherein contain:

(1) liquid of the liquid of cyclopolyol or soft solid derivative or reducing sugar or soft solid derivative, this derivative are that the 40-70% hydroxyl by cyclopolyol or reducing sugar obtains through esterification or etherificate, this derivative contain at least 2 or a plurality of respectively with C _8-22Ester group or ether that alkyl or alkenyl chain or its combination chain link to each other comprise at least 35% three ester or higher ester and derived from disaccharides, and the liquid of the liquid of this cyclopolyol or soft solid derivative or reducing sugar or soft solid derivative are through nucleus magnetic resonance T ₂Relaxation time measure 20 ℃ down the ratio of its solids and liquid be 50: 50 to 0: 100; With

(2) deposition aid is selected from cats product, nonionogenic tenside, anion surfactant, polymerization deposition aid, fabric softening compound or their mixture.

2. the fabric softening compositions of claim 1, wherein said liquid or soft solid derivative are to be obtained by cyclopolyol or reducing sugar 4 or 4 above hydroxyl etherificates or esterification.

3. the fabric softening compositions of claim 1, wherein said liquid or soft solid derivative are sugared polyester, sugared polyethers or sugared polyester and polyether.

4. the fabric softening compositions of claim 1, wherein said liquid or soft solid derivative are selected from sucrose cinnamic acid in May ester, sucrose four oleic acid esters, sucrose five eruciate and sucrose four eruciate.

5. the fabric softening compositions of claim 1, the ester of wherein said liquid or soft solid derivative or ether respectively with C ₈-C ₂₂Alkyl or alkenyl chain or C ₂-C ₈Chain links to each other, and C wherein ₈-C ₂₂Group and C ₂-C ₈The ratio of group is 5: 3 to 3: 5.

6. the fabric softening compositions of claim 1, wherein the solubleness of 20 ℃ of following fabric-softening immunomodulator compounds in softening water is lower than 1 * 10 ^-3% weight.

7. the fabric softening compositions of claim 6, wherein said fabric-softening immunomodulator compounds is a quaternary ammonium compound.

8. the fabric softening compositions of claim 1, wherein said liquid or soft solid derivative are 1: 10 to 15: 1 with the ratio of deposition aid.

9. the fabric softening compositions of claim 1, wherein said composition is liquid or emulsified body form.

10. the fabric softening compositions of claim 1 wherein also contains viscosity modifier.