CZ20014054A3 - Fabric softening composition - Google Patents

Abstract

The invention provides a fabric softening composition which has an increased resistance to malodour developement and which comprises: i) a liquid or soft solid derivative of a cyclic polyol (CPE) or of a reduced saccharide (RSE) resulting from 35 to 100 % of the hydroxyl groups in the polyol or saccharide being esterified or etherified, the CPE or RSE having 2 or more ester or ether groups independently attached to a C8-C22 alkyl or alkenyl chain, wherein at least one of the chains attached to the ester or ether groups has at least one unsaturated bond; and ii) a deposition aid; and iii) one or more antioxidant(s), wherein the weight ratio of i) to iii) is 20:1 or greater. The invention also provides a method of reducing malodour in a composition comprising a CPE or RSE as defined above by the addition of at least one antioxidant.

Description

Fabric softening agent

Technical field

The present invention relates to fabric softening compositions, particularly those which soften without adversely affecting the absorbency of the fabric and which have a reduced tendency to produce odor during manufacture, storage and use.

BACKGROUND OF THE INVENTION

The rinse-added fabric softening compositions are well known. However, a disadvantage of conventional rinse conditioners is that although they increase the softness of fabrics, they often simultaneously reduce their absorbency. This means that their ability to absorb water is reduced. This phenomenon is particularly disadvantageous in towels where the customer wishes the towel to be soft and still have high absorbency.

WO98 / 16538 (Unilever) discloses fabric conditioning compositions (fabric conditioners) comprising liquid or soft solid cyclic polyol derivatives or reduced sugar, providing good softening and preserving absorbency of the fabrics.

EP 0 380 406 (Colgate-Palmolive) discloses cleaning compositions comprising a sugar or a reduced sugar ester containing at least one fatty acid chain.

WO 95/00614 (Kao Corporation) discloses softening compositions comprising polyhydric alcohol esters and cationized cellulose.

US 5,447,643 (Huls) discloses aqueous fabric softeners comprising a nonionic surfactant and mono-, di- or triesters of fatty acids derived from certain polyols.

»♦

• «4 • · ► · · 4 4 • 4 • 4 • 4 * 4 • · 4 4 • 4 44 · 4 • · 4 44

Μ 4

WO 96/15213 (Henkel) discloses fabric softening agents containing sugar derivatives with an alkyl, acenyl and / or acyl group that are solid after esterification in conjunction with nonionic and cationic emulsifiers.

A fabric softening agent, liquid or in the form of a soft solid, eg, a cyclic polyol derivative (CPE) or reduced sugar (RSE) as defined herein, which is addressed by the above absorbency problem, is often obtained using unsaturated, usually predominantly unsaturated, fatty acid chains on ester or ether functional groups. However, such compositions may suffer from the fact that they produce odors during manufacture, storage or consumption. This is, of course, highly undesirable.

WO 97/13828 (P&G) discloses fabric treatment compositions comprising heavy metal sequestering agents.

WO 96/21714 and WO 96/21715 (P&G) disclose fabric conditioning compositions containing chelating agents.

WO 96/03481 (P&G) discloses fabric conditioning compositions containing 1 to 20% by weight of an antioxidant.

The present invention is directed to solving the above problems.

SUMMARY OF THE INVENTION

According to one aspect of the invention there is provided a fabric softening composition comprising:

(i) a liquid or soft solid derivative of a cyclic polyol (CPE) or reduced sugar (RSE), formed by the esterification or etherification of 35 to 100% of the hydroxyl groups of a polyol or sugar, the cyclic derivatives being

• * · • * «* • 4 • · • · 4 • ·> • • 9 • 4 · »· 4 4 · * 4

The 4 polyols or sugar have two or more ester or ether groups independently bonded to a C ₈ -C ₂₂ alkyl or alkenyl chain, wherein at least one of the chains attached to the ester or ether groups has at least one unsaturated bond; and ii) a deposition aid; and iii) one or more antioxidants, wherein the weight ratio of i) to iii) is 20: 1 or greater.

Surprisingly, it has been found that the above compositions provide an unexpected combination of simultaneous fabric softening and absorbency retention and exhibit improved odor release resistance, even at elevated temperatures.

According to another aspect of the invention there is provided a method of reducing odor in the manufacture, storage or use of a composition comprising CPE or RSE as described herein by adding at least one antioxidant.

In the context of the present invention, the abbreviations CPE or RSE refer to a cyclic polyol or reduced sugar derivative resulting from 35 to 100% of the hydroxyl groups of a polyol or reduced sugar being esterified or etherified, the CPE or RSE having two or more ester or ether groups independently linked to a C ₈ -C ₂₂ alkyl or alkenyl chain and at least one of the chains attached to the ester or ether groups has at least one unsaturated bond.

CPE or RSE

The CPE or RSE used according to the invention has no significant crystalline character at 20 ° C. Instead, it is preferably at a temperature of 20 ° C in a liquid state or a soft solid state as defined herein.

-4 <* 1 1 * 1 * * * * * * * * * * 1 1 1 1 1 1 1 1 1 1

The liquid or soft solids (as defined herein) of the CPS or RSE of the present invention are the result of esterification or etherification of 35 to 100% hydroxyl groups of the starting cyclic polyol or reduced sugar such that the CPS or RSE are in the desired liquid or soft solid state. Such groups typically include unsaturation, branching or mixed chain lengths.

The CPS or RSE typically has 3 or more ester or ether groups or mixtures thereof, for example 3 to 8 and especially 3 to 5. It is preferred that two or more of the ester or ether groups of the CPS or RSE are independently attached to a C ₈ -C ₂₉ alkyl or alkenyl chain. The C ₈ -C ₂₂ alkyl or alkenyl groups may be branched or straight carbon chains.

Preferably, 35 to 85% of the hydroxyl groups, more preferably 40 to 80%, and even more preferably 45 to 75%, such as 45 to 70%, are esterified or etherified.

Preferably, the CPS or RSE comprises at least 35% triesters or higher esters, e.g. at least 40%.

CPS or RSE have at least one of the chains independently attached to ester or ether groups having at least one unsaturated bond. This provides a cost effective way to produce CPS or RSE as a liquid or soft solid. It is preferred that the predominantly unsaturated fatty chains obtained, for example, from rapeseed oil, cottonseed oil, soybean oil, oil, tallow, palmitoleic, linoleic, erucous or other unsaturated vegetable fatty acid sources, are attached to ester and / or ether groups.

These chains are referred to below as the CPE or RSE ester or ether chains.

The ester or ether chains of CPE or RSE are preferably predominantly unsaturated. Preferred CPE or RSE include sucrose tetraester derived from tallow fatty acids, sucrose tetraester derived from fatty acids from rapeseed oil, sucrose tetraoleate, sucrose tetraesters derived from soybean oil or cottonseed oil, cellobiose tetraoleate, sucrose trioleate, sucrose trioleate peanut oil, sucrose pentaoleate, sucrose pentaester derived from rapeseed fatty acids, sucrose hexaoleate, sucrose hexaester derived from rapeseed fatty acids, sucrose triesters, pentaester and hexaesters derived from fatty acids from soybean oil or cottonseed trioleate, glucose tetraoleate, xylose trioleate, or sucrose tetra-, tri-, pentane or hexaesters with any mixture of predominantly unsaturated fatty acid chains. The most preferred CPE or RSE are those having mono-saturated fatty acid chains, i.e., in which any multiple double bond (polyunsaturation) has been removed by partial hydrogenation. Of course, some CPE or RSE having polyunsaturated fatty acid chains, such as sucrose tetralinolate, can be used provided that most unsaturated bonds have been removed by hydrogenation.

The most preferred liquid CPE or RSE are any of the above compounds, but with polyunsaturated bonds removed by partial hydrogenation.

Preferably, the unsaturated bond comprises 40% or more fatty acid chains, more preferably 50% or more, and most preferably 60% or more. In most cases, the unsaturated bond contains 65% to 100%, for example 65% to 95%, chains.

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

In the context of the present invention, the term cyclic polyol includes all forms of sugars. In fact, sugars are particularly preferred for use in the present invention. Examples of preferred sugars for CPS and RSE derived therefrom are monosaccharides and disaccharides.

Examples of monosaccharides include xylose, arabinose, galactose, fructose, sorbose and glucose. Glucose is particularly preferred. Examples of disaccharides include maltose, lactose, cellobiose and sucrose. Sucrose is particularly preferred. An example of a reduced sugar is sorbitan.

Liquid or soft solid CPEs can be prepared by methods well known to those skilled in the art. These include acylation of the cyclic polyol or reduced sugar with acid chloride; transesterifying cyclic polyol fatty acid esters or reduced sugar using a variety of catalysts; acylating the cyclic polyol or reduced sugar with an acid anhydride; and acylating the cyclic polyol or reduced sugar with a fatty acid. See, for example, U.S. Patents 4,386,213 and AU 14416/88 (both P&G).

It is preferred that the CPE or RSE have 3 or more preferably 4 ester or ether groups or more. If the CPE is a disaccharide, it is preferred that the disaccharide has 3 ester or ether groups or more. Particularly preferred CPEs are esters having a degree of esterification of 3 to 5, for example sucrose tri-, tetra- and pentaesters.

When the cyclic polyol is a reduced sugar, it is preferred that each CPE ring has one ester or ether group, preferably in the Cl position. Suitable examples of such compounds include methylglucose derivatives.

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

• · ·

-7 • it

The length of the unsaturated chains (and even saturated chains, if present) in the CPE or RSE is C ₈ -C ₂₂ , preferably C ₁₂ -C ₂₂ . It is possible to include one or more C 1 -C ₈ chains, but these are less preferred.

Liquid or soft solid CPE or RSE according to the present invention are characterized as having a solid to liquid ratio at 20 ° C between 50:50 and 0: 100 as determined by T ₂ NMR relaxation time, preferably between 43:57 and 0: 100 and more preferably between 40:60 and 0: 100, such as 20:80 and 0: 100. T ₂ NMR relaxation time is commonly used to characterize solid to liquid ratios in soft solid products such as fats and margarines. For the purposes of the present invention, any T ₂ signal component less than 100 με is considered a solid component and any T ₂ component> 100 με is considered a liquid component.

The prefixes (eg tetra- and penta-) of CPE and RSE indicate only average degrees of esterification. The compounds exist as a mixture of materials from the monoester to the fully esterified ester. It is the average degree of esterification used here to define CPE and RSE.

The equilibrium state of hydrophilic and lipophilic components, HLB (hydrophilic-lopophilic balance) is typically between 1 and 3 in CPE and RSE.

The CPE or RSE is preferably present in the composition in an amount of from 0.5 to 50% by weight based on the total weight of the composition, and more preferably from 1 to 30% by weight, such as from 2 to 25%, e.g. means.

CPE and RSE for use in the compositions include the compounds exemplified in the following examples, including sucrose tetraoleate, sucrose pentaerucate, sucrose tetraerucate and sucrose pentaoleate.

Storage aid

In the context of the present invention, the deposition aid is defined as any material that aids the deposition of selected CPE or RSE onto the fabric during the laundering process.

The deposition aid may be selected from cationic compounds such as cationic surfactants, nonionic surfactants, anionic surfactants, polymeric deposition aids or mixtures of such agents. Quaternary ammonium compounds have been found to be particularly effective. A class of preferred deposition aids are fabric softeners.

It is preferred that the deposition aid be cationic in nature. If the composition does not contain a cationic surfactant or cationic deposition aid, the presence of a cationic polymeric deposition aid is preferred. Preferably, the deposition aid is both cationic and fabric softener.

Mixtures of deposition aids can be used, for example mixtures of a cationic surfactant and a nonionic surfactant, or fabric softeners and polymeric deposition aids.

Suitable cationic deposition aids include single-chain water-soluble quaternary ammonium compounds. Examples include cetyltrimethylammonium chloride, cetyltrimethylammonium bromide, or any of the materials disclosed in Akzo Nobel European Patent No. 258 923.

However, it is preferred that the deposition aid be a substantially water-insoluble fabric softener. Particularly preferred are substantially water-insoluble quaternary ammonium materials containing a single alkyl or alkenyl chain having an average length equal to _C20 or _C20 ;

-9big. Even more preferred are compounds comprising a polar warhead group (the hydrophilic portion of an amphiphilic molecule) and two alkyl or alkenyl chains, each having an average chain length equal to or greater than C ₄ or greater.

Preferred deposition aids and fabric softeners have two long alkyl or alkenyl chains with an average chain length equal to or greater than C ₁₄ . More preferably, each chain has an average chain length greater than _C16 . Preferably at least 50% of the alkyl or alkenyl group has a long chain length of the chain C in _{the 18th}

It is preferred that the long-chain alkyl or alkenyl groups of the deposition and softening fabric are predominantly straight (linear).

The deposition and fabric softening agents used in the compositions of the invention are excellent softening molecules.

Substantially water-insoluble fabric softeners in the context of the present invention are defined as fabric softeners having a solubility of less than 1 x 10 ^-3 % by weight. in demineralized water at 20 ° C. Deposition aids and fabric softeners preferably have a solubility of less than 1 x 10 ⁴ % by weight. Top are deposition aids, fabric softening and dissolution in demineralised water at 20 ° C of from 1 x 10 ⁸ to 1 x 10 ^-6 wt%.

Preferred deposition aids and fabric softeners are quaternary ammonium compounds, preferably those having at least one ester bond.

It is particularly preferred that the deposition and softening fabric is a water-insoluble quaternary ammonium material which:

- 10 includes a compound having two _C12 . _an alkyl or alkenyl group attached to the molecule via at least one ester bond. Even more preferably, the quaternary ammonium material has two ester bonds.

A particularly preferred ester-linked quaternary ammonium material for use in the invention may be represented by the formula (I):

R ¹

I _{R 1} - N- (CH ₂ ) _n - T - R ² X '

I _(CH2) "- t - R ² (I) wherein each R is independently selected from alkyl, hydroxyalkyl or C _{2nd 4} alkenyl groups; and wherein each R group is independently selected from C _g . _2g alkyl or alkenyl groups;

O O

T is -O-C- or-C-O-;

X 'is any suitable anion and n is 0 or an integer from 1 to 5.

Preferred materials in this class include:

di (alkanoyloxyethyl) -dimethylammonium chloride and methyl bis- [ethyl (alkynoyl)] - 2-hydroxyethylammonium methylsulfate, wherein the alkane is derived from tallow fatty acids.

The second preferred type of quaternary ammonium material may be represented by formula (II):

OOCR ²

I (R ^') 3 N ⁺ - (CH2) _n - CH X

AND

CH ₂ OOCR ² (II)

- 11 fcfc ♦ fcfcfc fcfcfc fcfcfc fcfcfc fcfc fcfcfc where R ¹ , η, X 'and R ¹ correspond to the above definition.

It is advantageous for the environment if the quaternary ammonium material is biodegradable.

Preferred materials of this class, such as 1,2-bis (alkanoyloxy) -3-trimethylammonium propane chloride, wherein the alkane is derived from tallow hardened fatty acids, and a process for their preparation, are described, for example, in U.S. Patent 4,137,180 to Lever Brothers. These materials preferably contain small amounts of the corresponding monoester, as described in US 4,137,180 for 1-alkanoyloxy-2-hydroxy-3-trimethylammonium propane chloride, wherein the alkane is derived from tallow hardened fatty acids.

The deposition and softening fabrics included in the composition may also be compounds of formula (III):

OOR ⁴

II II i

R ³ - C - O -) mA (- O - C - B - N ⁺ - R ⁵ ) n X '

AND

R ⁶ (III) wherein X is an anion, A is (n + m) a powerful radical remaining after removal of (n + m) hydroxy groups from an aliphatic polyol having p hydroxy groups, carbon to oxygen ratio ranging from 1.0 to 3 , 0 and for one hydroxyl group having at most 2 groups selected from ethylene oxide and propylene oxide, m is 0 or an integer from 1 to pn, n is an integer from 1 to pn, p is an integer equal to at least 2,

B is an alkylene or alkylidene group containing from 1 to 4 carbon atoms,

R ³ , R ⁴ , R ⁵ and R ⁶ are, independently of each other, straight or branched C 1 -C ₄₈ alkyl or alkenyl groups optionally substituted with one or more functional groups and / or with a break of not more than ten

ethylene oxide and / or propylene oxide groups, or at most two functional groups selected from

O O O 0 0

II II 1

- C - O -, - O -, - C -, - N -, and - O - C - O or R ¹¹ and R ¹² can form a ring system containing 5 or 6 ring atoms, with provided that the average compound has either at least one R group having 22 to 48 carbon atoms, or at least two R groups having 16 to 20 carbon atoms, or at least three R groups having 10 to 14 carbon atoms. Preferred compounds of this type are described in EP 638 639 (Akzo).

The deposition aid may also include a mixture of different fabric softeners, for example, a mixture of compounds of Formula (I) and Formula (II).

The deposition aid may also be a nonionic surfactant, such as a nonionic ethoxylated surfactant having an HLB of from 10 to 20. Preferably, the surfactant alkyl group contains at least 12 carbon atoms.

Suitable deposition aids for use in the invention include cationic and nonionic deposition aids.

Suitable cationic polymeric deposition aids include cationic guar polymers such as the Jaguar series (from Rhodia), cationic cellulose derivatives such as Celquats (from National Starch), Ucare polymers (from Amerchol), cationic starches such as potato starch such as SoftGels and Solvitose such as BDA (from Avebe), a C * bonded polymer series from Cerestar, cationic polyacrylamides such as PCG (from Allied Colloids), a series of polymers Flocaid (from National Starch) and cationic chitosan and its derivatives. Cationic polymeric aids

13 deposition is particularly preferred if the composition does not contain any other cationic material.

Suitable nonionic deposition aids include Pluronics (from BASF), dialkylated polyethylene glycols, cellulose derivatives as described in GB 213 73 (Unilever), hydroxyethylcellulose, starch, and hydrophobically modified nonionic polyols such as Acusol 880/882 (from Rohm & Haas) ).

Mixtures of any of the foregoing deposition aids can be used.

In fabric softening compositions, the weight ratio of CPE or RSE to deposition aid is preferably in the range of 15: 1 to 1:10, more preferably in the range of 10: 1 to 1: 5 and most preferably in the range of 8: 1 to 1: 3.

If the composition is desired to impart a particularly high absorbency to the fabrics, it is preferred that the weight ratio of CPE or RSE to the deposition aid is at least 1: 1 (especially when the deposition aid is a fabric softener).

If a high emollient is desired, it is preferred that the weight ratio of the emollient to CPE or RSE be at least 2: 3, and more preferably at least 1: 1.

In order to impart excellent fabric softening and absorbency, it is preferred that the weight ratio of the deposition softener to CPE or RSE be in the range of from 3: 2 to 1: 10 and more preferably from 2: 3 to 1:10.

Fabric softening compositions include one or more antioxidants in a weight ratio to CPE or RSE of 20: 1 or greater.

The deposition aid is preferably present in the compositions in an amount of 0.05 to 15% by weight based on the total weight of the composition, more preferably 0.1 to 10%, such as 0.5 to 7.5% by weight based on the total weight means.

Antioxidant

Any suitable antioxidant may be used according to the invention. Preferably, the antioxidant comprises at least one antioxidant initiation inhibitor and at least one propagation inhibitor. Mixtures of these two types of antioxidants have been shown to be particularly beneficial, particularly for reducing moderate to long-lasting odors. Any of the antioxidants mentioned in the following examples can be used.

The compositions preferably comprise 0.0001% to 1% by weight (total), based on the total weight of the composition, of antioxidants, more preferably 0.00015% to 0.75% and even more preferably 0.002 to 0.5, for example 0.002 to 0.45% by weight relative to the total weight of the composition.

It has been found that short-term and long-lasting odors can well suppress initiation of antioxidant inhibition, but a mixture of propagation-inhibiting and initiation-inhibiting antioxidants can provide surprisingly good short-lasting odor control.

Suitable initiation inhibiting antioxidants include peroxide decomposers (e.g., sulfides, aryl and alkyl phosphites, metal salts of some thiodipropionates, xanthates, and dithiophosphates).

Suitable peroxide decomposing agents include (RO ₂ CCH ₂ CH ₂ ) ₂ S, wherein R is C ₁₂ H ₂₅ , C _h H ₂₉ or C ₁₈ H ₃₇ , ie TNPP (tris-nonylphenyl phosphite), available as Irgafos 186; Sandostab P-EPQ; and Irgafos P-EPQ. If used, they are substances

- 15 • * 9 9 9 ·· ·

9 · 9 9 999 9 9 9 9 9 9 9 9 9 9

The peroxide-decomposing peroxide is preferably present in an amount of between 0.001% and 0.5% by weight, and most preferably between 0.005 and 0.1% by weight.

Another type of suitable initiation inhibiting antioxidant is metal sequestering agents or deactivators. Suitable substances of this type include

N, N'-disalicylidene-1,2-propanediamine; oxalyl bis (benzylidene hydrazide); ethylenediaminetetraacetic acid (EDTA), ethylenediamine-N, N'-disuccinic acid (EDDS); N-hydroxyethylenediaminetriacetic acid; nitrilotriacetic acid (NTA); ethylenediaminetetrapropionic acid; ethylenediamine-N, N'-diglutamic acid; 2-hydroxypropylenediamine-N, N'-disuccinic acid; triethylenetriamine hexaacetic acid; diethylenetriaminepentaacetic acid (DETPA); trans-1,2-diaminecyclohexane-N, N, Ν ', N'-tetraacetic acid; ethanoldiglycine; ethylenediaminetetrakis (methylenephosphonic acid) (EDTMP); 1-hydroxyethane-1,1-diphosphonic acid (HEDP); hydroxyethyldimethylenephosphonic acid; gluconic acid; citric acid; tartaric acid, isopropylcitronic acid; oxydisuccinic acid; dipicolinic acid;

4,5-dihydroxy-m-benzenesulfonic acid; 8-hydroxyquinoline; sodium dithiocarbamate; sodium tetrafenylborane, ammonium nitrosophenylhydroxylamine; ethylenediamine succinic acid (EDMS); Iminodisuccinic acid sodium salt (Na salt IDS); tetrakis [methylene (3,5-di-tert-butyl-4-hydroxyhydrogen sulphate)] methane (Irganox 1010); 1,3,5-trimethyl-2,4,6-tris- (3 ', 5'-di-tert-butyl-4'-hydroxybenzyl) benzene (Irganox 1330) and diethylene triaminpenta (methylene phosphonate) (Dequest 2066) .

The metal sequestering agents are preferably present in an amount between

0.0100% and 0.5% by weight based on the total weight of the composition, and most preferably between 0.005% and 0.1% by weight based on the total weight of the composition.

Propagation inhibiting antioxidants consist primarily of inhibited phenols / polyphenols. These may include those commonly used in the food or plastics industry, such as butylated hydroxyanisole

(BHA); butylated hydroxytoluene (BHT); tert-butyl hydroquinone (TBHQ); tocopherols; tocotrienols; ascorbic acid; ascorbyl palmitate, octyl gallate; propyl gallate; lauryl gallate; N, N-bis (ethyl-3 ', 5'-di-tert-butyl-4-hydroxybenzoate; 2- (N, N-dimethylamino) ethyl-3', 5'-di-tert-butyl-4-hydroxybenzoate -N-amine, wherein the amine contains coconut-derived fatty acid, 2- (N-methyl-N-amino) ethyl-3 ', 5'-di-tert-butyl-4-hydroxybenzoate, wherein the amine contains fatty acid derived from coconut oil; 2,2'-methylenebis (4-methyl-6-t-butylphenol), 4,4'-butylidene-bis (2-tert-butyl-5-methylphenol), n-octadecyl-3,5- di-tert-butyl-4-hydroxyhydrogen sulphate, 1,1,3-tris (3-tert-butyl-4-hydroxy-6-methylphenyl) butane.

The inhibitory antioxidants are preferably present in an amount of 0.0001% to 0.5% by weight based on the total weight of the composition, more preferably between 0.0002% and 0.05% by weight, and most preferably between 0.0002% and 0.02% by weight relative to the total weight of the composition. to the total weight of the composition.

The weight ratio of the initiation inhibitor (i) to the propagation inhibitor (ii) is preferably in the range from 10: 1 to 1:10, more preferably from 10: 1 to 1: 5 and even more preferably from 8: 1 to 1: 1, for example from 6: 1 to 1: 1.

The weight ratio of CPE or RSE to the total amount of antioxidant is 20: 1 or greater, preferably 50: 1 or greater, more preferably 75: 1 or greater. The weight ratio can be up to 1500: 1 or greater. It is preferred that the weight ratio has an upper limit of 3000: 1, for example 2500: 1.

pH of the composition

The compositions of the present invention preferably have a pH of from 1.5 to 7, and more preferably from about 1.5 to about 7

1,5 to 5.

Other ingredients

- 17 · to to to to to 17 17 17 17 17 17 17 17 17

The compositions may also contain fatty acids, for example, C ₈ -C ₂₄ alkyl or alkenyl monocarboxylic acids, or polymeric carboxylic acids. Preferably, saturated fatty acids are used, especially _{C16- C18} fatty acids from hardened tallow.

The compositions may also contain one or more of an optional additive selected from electrolytes, non-aqueous solvents, buffering agents, perfumes, perfume carriers, fluorescent agents, colorants, hydrotropes, antifoams, antifoaming agents, polymeric and other fillers, enzymes, optical brighteners, opacifiers, anti-clotting agents, anti-wrinkling agents, anti-staining agents, anti-staining agents, germicides, fungicides, anti-rusting agents, dampeners, antistatic agents, sunscreens, color retardants and ironing agents.

If the article is liquid, it may be advantageous if the viscosity controlling agent is present. Any such agent used with rinse conditioners is suitable for use with the present invention; for example, biological polymers such as xanthan gum (Kelco from Kelsan and Rhodopol from Rhone-Poulenc), starches and cellulose ethers. Suitable viscosity control agents are synthetic polymers such as polyacrylic acid, polyvinylpyrrolidone, polyethylene, carbomers, crosslinked polyacrylamides such as Acosol 880/882 polyethylene and polyethylene glycols.

It is preferred that the compositions be substantially free of bleaching agents. Preferably, the compositions are then completely free of bleaching agents.

Eliminating polymers are also suitable as viscosity modifiers. bonding and deflocculating polymers.

- 18 * 4

Product form

The compositions may be in any form commonly used for fabric softeners, for example, as a powder, paste, gel, or liquid. Fluids and especially emulsions are preferred.

The compositions may be prepared by any suitable method. If the antioxidant is oil soluble, for example a propagation inhibitor, it is suitably added in advance with CPE or RSE. If the antioxidant is water-soluble, for example an initiation inhibitor, in particular a metal sequestering agent, such an inhibitor is typically added additionally to the preformed emulsion containing CPE or RSE.

DETAILED DESCRIPTION OF THE INVENTION

The invention is illustrated by the following non-limiting examples. Other examples outside the scope of the present invention will be apparent to those skilled in the art.

Examples 1 to 13 and 14 to 24

Below is the effect of the antioxidant on reducing odor formation in fabric softening compositions containing CPE and a storage aid when stored.

All percentages are by weight based on the total weight of the composition and are the amount of active compound. Examples 1 and 14 are controls that do not contain an antioxidant. In Ryoto 0-170 (sucrose pentaoleate, available from Mitsubishi-Kagaku Food Corporation), 85% or more of the fatty acid chains contain an unsaturated bond.

- 9 • 9 9

• 9

9 9 • 9 9 ·· 999

Examples 2-13 were prepared by dissolving propagation-inhibiting antioxidants (Irganox 1330 or Irganox 1010) in CPE (Ryoto 0-170) and adding the resulting mixture to a separate cationic / water mixture (in an amount to make up the composition to 100% by weight). The resulting formulation was mixed using a Heidolph low shear mixer to form an emulsion.

In Examples 6 to 13, the initiation-inhibiting antioxidant (Dequest 2066, diethylenetriaminpenta (methylene phosphonate) was added to this emulsion additionally.

Examples 14 to 24 were prepared by mixing cationic surfactant (CTAC, cetyltrimethylammonium chloride) with water and then adding CPE (Ryoto 0-170) to this mixture at room temperature under high shear conditions to form an emulsion.

In Examples 15 and 22-24, the antioxidant propagation inhibition (Irganox 1010) was dissolved in CPE prior to emulsification.

In Examples 16 to 24, the antioxidant initiation inhibition (Dequest 2066, DTPA or Na salt IDS) was additionally added to the final emulsion.

The compositions of Examples 1-13 and 14-24 are set forth in Tables 1 and 2.

Table 1

example % Ryoto O-170 ^a % CTAC ^b % inh. initiation DEQUEST 2066 ^c % inh. promotion % inh. propagace B 1 (control) 4,5 1.0 - - - 2 4,5 1.0 - 0.00225 - 3 4,5 1.0 - 0.0045 - 4 4,5 1.0 - - 0.00225 5 4,5 1.0 - - 0.0045 6 4,5 1.0 0.01 0.00225 - 7 4,5 1.0 0.01 0.0045 - 8 4,5 1.0 0.01 - 0.00225 9 4,5 1.0 0.01 - 0.0045 10 4,5 1.0 0.05 0.00225 - 11 4,5 1.0 0.05 0.0045 - 12 4,5 1.0 0.05 - 0.00225 13 4,5 1.0 0.05 - 0.0045

^and sucrose pentaoleate (from Mitsubishi-Kagaku Food Corporation) ^b cetyltrimethylammonium chloride (from Aldrich, as a 25% solution) ^c diethylenetriaminpenta (methylene phosphonate) available from solutions A is Irganox 1330; 1,3,5-trimethyl-2,4,6-tris- (3 ', 5'-di-tert-butyl-4'-hydroxybenzyl) benzene.

B is Irganox 1010; tetrakis [methylene (3,5-di-tert-butyl-4'-hydroxyhydrogen sulphate)] methane; both fabrics are supplied by Ciba Geigy.

4 «4

-21 * 44 · ·· 4 4 44 * · * · * 4 4 4 4 4

4,444 444

Table 2

example % Ryoto 0-170 % CTAC % inhibitor promotion Irganox 1010 inh. initiation (type and%) water (%) 14 (control) 4,5 0.5 - - to 100 15 Dec 4,5 0.5 0.0045 - to 100 16 4,5 0.5 - 0.01 - Dequest 2066 ^a to 100 17 4,5 0.5 - 0.01 - DTPA ^b to 100 18 4,5 0.5 - 0.01 NA salt of IDS ° to 100 19 Dec 4,5 0.5 - 0.05 - Dequest 2066 ^a to 100 20 May 4,5 0.5 - 0.05 - DTPA ^b to 100 21 4,5 0.5 - 0.05 NA salt of IDS ^C to 100 22nd 4,5 0.5 0.0045 0.01 - Dequest 2066 ^a to 100 23 4,5 0.5 0.0045 0.01 - DTP A ^b to 100 24 4,5 0.5 0.0045 0.01 NA EDS salt ^C to 100

^and diethylenetriamine-N, N, N ', N, N-pentacismethylene phosphoric acid (from Solutia) ^b diethylenetriamine pentaacetate (from Akzo Nobel) ^c iminodisuccinic acid sodium salt (from Bayer)

The samples were stored in glass vials with screw cap at 37-45 ° C. At the intervals indicated in Tables 3 and 4, the vials were removed from storage and samples were evaluated for odor formation (as determined by determining the level of repulsive fat odor present). Prior to each assay, samples were allowed to equilibrate at room temperature. The odor was determined at room temperature by smelling the odor from the equilibrated sample and determining a value from 0 to 5 to indicate

-22 odor levels. A sample showing no perceptible repulsive odor and a very strong repellent odor were marked with zero. Each sample was evaluated by at least 10 people and the data were averaged.

An emulsion containing 1% CTAC and 4.5% by weight of Priolube 1446 (neopentyl glycol dioleate from Unichema) was stored at 45 ° C for 4 weeks as a measure of 5 for the repellent fat odor.

The odor assessment for Examples 1 to 13 and 14 to 24 is shown in Tables 3 and 4. Table 3 below gives the values set for Examples 1 to 13 during a test period of 27 weeks when stored between 37 and 45 ° C.

Table 3

ex. week 1 Week 2 week 4 week 6 week 8 week 12 week 15 week 27 1 (cont.) 1.7 2.00 2.20 3.53 4.00 4.53 4.22 4.31 2 1.1 1.64 1.80 2.71 3.06 3.42 4.16 4.69 3 1.7 1.86 1.53 2.5 2.94 3.32 4.16 4.38 4 1.4 1.71 1.40 2.43 2.82 2.89 4.05 4.38 5 1.4 2.07 1.87 2.79 2.94 3.26 4,11 4.69 6 0.9 0.85 1.13 1.20 1.47 1.50 1.72 2.13 7 0.8 1.15 1.13 1.20 1.47 1,22 1.61 1.94 8 1.4 1.46 1,27 1.40 1.60 1.56 1.42 2.06 9 1.3 1.31 1.33 1.47 1.67 1.50 1.69 2.00 10 2.3 2.50 2.27 3.00 2.61 2.84 2.67 3.19 11 2.1 2.14 2.00 2.73 2.44 2.74 2.39 3.19 12 2,0 2.21 2.07 2.73 2.56 2.84 2.28 3.19 13 2,0 2.00 1.67 2.73 2.33 2.95 2.56 3.44

The above results show odor suppression for a sample containing predominantly unsaturated CPE and a sedimentation aid in the form of an addition

-23,949 9 4 4 4

999 · · · ··

9 9 9 · 9 • 9 9999 * 9 9 9 9 9

944 9 · 4 · »99 449 99 9 Antioxidants. Where the antioxidant is a mixture of a propagation inhibitor and an initiation inhibitor, longer-term odor control has been achieved.

Favorable consistent results were further obtained using 0.01% by weight initiation inhibitor together with 0.0025 to 0.0045% by weight propagation inhibitor (see Examples 6-9).

Table 4 below gives the odor values determined for Examples 14 to 24 during 4 weeks of testing when stored at 45 ° C.

Table 4

example week 1 Week 2 week 3 week 4 14 (control) 2.50 2.71 2.76 3.00 15 Dec - 2.43 2.75 2.83 16 1.83 1.86 1.17 1.75 17 1.67 1.79 1.33 1.83 18 1.58 1.93 2.17 1.50 19 Dec 2.17 1.86 1.58 1.83 20 May 2.25 2.00 1.50 1.67 21 1.75 1.93 1.42 1.83 22nd 1.60 1.07 1.00 1.42 23 1.17 1.57 1,25 0.83 24 1.00 1,21 1.75 1,25

The results shown in Table 4 show that when the only antioxidant used is an initiation inhibitor, odor control was achieved. When the antioxidant contained both a propagation inhibitor and an initiation inhibitor, significantly improved odor control was obtained. This is surprising given that

* 4 4 « 44 • 4 44 4 4 4 4 4 4 4 4 • 4 • 4 • • 4 4 4 4 4 • 4 4 • 4 4 4 4 4 4 4 44

when only a propagation inhibitor was used as an antioxidant, little or no odor control was achieved.

Thus, there is a significant concordant (synergistic) effect between the propagation inhibitor and the initiation inhibitor.

In the following examples, additional compositions are shown showing improved odor control in the presence of a propagation inhibitor and an initiation inhibitor.

Examples 25 to 34

Table 5 (mixtures with CTAC)

example 25 26 27 Mar: 28 cetyltrimethylammonium chloride (CTAC) 1 1 1 1 sucrose pentaoleate (Ryoto 0-170) 4 Sucrose tetraoleate (oily liquid) 4 sucrose pentaerucate (Ryoto R-190) (slow flowing liquid) 4 Tetraureate (Ryoto ER-290) (slow flowing liquid) 4 Irganox 1010 0,002 0,002 0,002 0,002 Dequest 2066 0.01 0.01 0.01 0.01 water 95 95 95 95 CTAC ratio 1: 4 1: 4 1: 4 1: 4

Iranox 1010. Dequest 2066 and CTAC have been described above.

-25 ♦ · »♦ 0 * 0 0 * * * *

0 · 0 0 0 0

0 0 0 0

0000,000,000 · 0 0

Ryoto products are available from Mitsubishi-Kagaku Food Corporation. The examples in Tables 6-9 below were prepared by heating the ingredients together at 80 ° C and mixing them at high shear.

Table 6: HEQ (fabric softener) blends

example 29 30 31 HEQ ¹ 0.86 2.57 £ 71 fatty acid 0.14 0.43 0.39 sucrose pentaoleate (Ryoto 0-170) (oil-like liquid) 4 2 3 Irganox 1010 0.004 0,002 0.003 Dequest 2066 0.01 0.01 0.01 water 95 95 95 HEQ ratio 1: 4 3 - 2 2 - 3

^! HEQ is 1,2-bis [alkanoyloxy] -3-trimethylammonium propane, wherein the alkane is derived from tallow hardened fatty acids and is supplied by Hoechst.

♦ tt · • · < tt · tt tt • tt • · • tt tt • · • · • tt Tt tt tt tt tt tt · tttt · «• tt • tt

Table 7: mixtures with Arquad 2-HT

example 32 33 34 Arquad 2-HT ^a 1 1 1 Sucrose tetraoleate (oily liquid) 4 sucrose penteurate (Ryoto ER-190) (oily liquid) 4 sucrose tetraureate (Ryoto ER-290) (oily liquid) 4 Irganox 1010 0.004 0.004 0.004 Dequest 2066 0.01 0.01 0.01 water 95 95 95 ratio Arquad 2-HT: oil 1: 4 1: 4 1: 4

^and Arquad 2-HT is dimethylammonium chloride, tallow, having tallow-derived fatty acids.

Example 35

Example 35 was prepared as a 5% emulsion / dispersion of total active ingredient in water containing 4.5% sucrose tetraerucate (oily liquid, Ryoto ER 290), 0.5% CTAC, 0.01% Dequest 2066, 0.0045% Irganox 1010 and 0.2% polymer compound to aid deposition as shown below:

in Example 35a: FlocAid 34 (from National Starch) in Example 35b: Softgel BDA (from Avebe).

Example 36

Example 36 was prepared as a 1: 4 mixture of emulsion / dispersion (with 5% total active ingredient) di (alkanoyloxyethyl) dimethylammonium chloride, wherein the alkyl is derived from tallow fatty acids (DEEDMAC) and sucrose pentaoleate (Ryoto

0-170) by mixing at high temperatures. To this mixture were added Dequest 2066 in an amount of 0.01% and Irganox 1010 in an amount of 0.004%.

Example 37

The fully formed fabric softening composition of the present invention was prepared as follows:

• ·· ·· · « ♦ fc w 1 • * 4 • · • · · • · ··· ···· • • * «Fcfc • • • fcfcfc fc · fcfc · • · • fc •

component % by weight GenapolC150 ^a 1.6 ABS ^b 0.4 Ryoto 0-170 15.4 Cationic potato starch ^c 2,0 perfume 0.96 preservative small amount dye small amount For salt IDS 0.01 Irganox 1330 0.015 water balance

^and alcohol 15 EO, removal, from coconut oil, from Glariant ^b dodecylbenzenesulfonic acid salt (from Aldrich Chemical

Company) ^c Softgel BDA (by Avebe)

Example 38

• ·· · · • © 9 · © 99 • 9 • • · · • • · • ·· © ··· ··· ··

·· · · · · · · ·

Table 8 shows the solid / liquid ratio for T2 NMR of CPE and RSE used in the present invention. The ratios were measured at 20 ° C. The degree of esterification / etherification is also indicated.

Table 8

material fixed ratio substance: liquid at 20 ° C degree and% esterification physical form 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 sucrose tetraoleate 0: 100 4/8 50% liquid sucrose octaoleate 0: 100 8/8 100% liquid

Ryoto materials have been described above.

Examples 39 to 52

All of the compositions in Table 9 were prepared as follows: The propagation inhibitor was dissolved in sucrose tetraoleate at a weight ratio of 99.9: 0.1. This mixture was then melted together with TEA (triethanolamine) and coconut-15EO alcohol and then added to water at 60 ° C with stirring using a Heidolph low shear mixer. The resulting mixture was stirred for 10 minutes and then cooled to room temperature. If an initiation inhibitor was used, it was added additionally, with stirring, to the resulting mixture as a 5% solution in water.

Table 9

př · % TEA ^and % sucrose tetraoleate ^b % coconut. 15 EO % ihib. promotion 1330) Inic Inhibitor. (% and type) % water 39 10.6 3.6 0.1 0.0036 0.01 EDDS ^C to 100 40 10.6 3.6 0.1 0.0036 0.01 Dequest 2066 to 100 41 10.6 3.6 0.1 0.0036 0.01 Na salt IDS to 100 42 10.6 3.6 0.1 0.0036 0.01 DTPA to 100 43 10.6 3.6 0.1 0.0036 0.01 EDTA ^d to 100 44 10.6 3.6 0.1 0.0036 0.01 Dequest 2047 ^e to 100 45 10.6 3.6 0.1 0.0036 none to 100 46 7.5 7.5 0.1 0.0075 0.001 EDDS to 100 47 7.5 7.5 0.1 0.0075 0.01 Dequest 2066 to 100 48 7.5 7.5 0.1 0.0075 0.01 Na salt IDS to 100 49 7.5 7.5 0.1 0.0075 0.01 DTPA to 100 50 7.5 7.5 0.1 0.0075 0.01 EDTA to 100 51 7.5 7.5 0.1 0.0075 0.01 Dequest 2047 to 100 52 7.5 7.5 0.1 0.0075 none to 100

^and methyl-bis- [ethylalkanoyl)] - 2-hydroxyethylammonium methyl sulfate, wherein the alkane is derived from tallow fatty acids (available as a 90% paste under the trade name Rewoquat WE18 from Goldschmidt, formerly Witco).

sucrose polyoleate with an approximate degree of esterification of 4. ^c ethylenediamine-N, N'-disuccinic acid (from Associated Octel). ^d ethylenediaminetetraacetic acid (from Contract Chemicals). ^and ethylene diamine tetra (methylene phosphonate) (from Solutia).

Table 10 below shows the odor values determined for samples 39-52 during the nine week test period when stored at 45 ° C.

-30All samples were stored in loosely sealed glass vials at 45 ° C. At weekly intervals, samples were removed from the heated oven and allowed to cool to room temperature before testing. Odor scores were from 0 to 5, where 0 = odorless and 5 = extremely strong odor. The results are shown in Table 10.

Table 10

ex. week 1 Week 2 week 3 week 4 week 6 week 9 35 0.88 1.37 1,28 1.18 1.38 1.30 36 1.59 1.63 1.00 1,27 1.31 1.10 37 1.29 1.47 1.43 1.82 1,23 1.40 38 1.18 1.32 1.07 1.64 1,23 1.65 39 1.12 1.47 1.29 1.36 1.15 1.60 40 1.41 1.32 1,21 1.45 1.08 1.70 41 2.12 1.89 1.71 2.09 1.77 2.50 42 1.65 1.76 1.75 1.73 1.62 1.70 43 1.65 1.47 1.75 1.82 1.62 1.50 44 1.71 1.18 1.92 1.55 1.08 1.10 45 1.82 1.47 1.83 1.18 1.46 1.00 46 1.65 1.53 1.50 1.45 1.38 1.50 47 1.82 1.59 1.75 1.64 1.31 1.40 48 2.12 1.65 2.25 2.27 2.38 2.20

The results show that when only a propagation inhibitor was used in the softening compositions, good odor control was observed over a nine week period. When a mixture of propagation and initiation inhibitors was used in the emollients, a significantly better odor control was observed over the nine-week period.

Claims (11)

CLAIMS 1. A fabric softening composition comprising: (i) a liquid or soft solid derivative of a cyclic polyol or reduced sugar, formed by esterification or etherification of 35 to 100% of the hydroxyl groups of a polyol or sugar, wherein the cyclic polyol or sugar derivatives have two or more ester or ether groups independently bonded to C ₈ -C ₂₂ an alkyl or alkenyl chain, wherein at least one of the chains attached to the ester or ether groups has at least one unsaturated bond; and ii) a deposition aid; and iii) one or more antioxidants, comprising at least one initiation inhibitor and at least one propagation inhibitor, wherein the weight ratio of i) to iii) is 20: 1 or greater. 2. A fabric softening composition according to claim 1 wherein the cyclic polyol or reduced sugar comprises at least 35% triesters or higher esters. The fabric softening composition according to claim 1 or 2, characterized in that the cyclic polyol or reduced sugar has 40 to 80%, and preferably 45 to 75% of the hydroxyl groups esterified and / or etherified. The fabric softening composition according to any one of the preceding claims, wherein the cyclic polyol or reduced sugar has 4 or more hydroxyl groups esterified or etherified. 9 9 9 · -325. The fabric softening composition of any preceding claim, wherein the cyclic polyol or reduced sugar is derived from a monosaccharide or a disaccharide. The fabric softening composition of any one of the preceding claims, wherein the deposition aid is selected from cationic surfactants, nonionic surfactants, anionic surfactants, polymeric deposition aids, fabric softening compounds, or mixtures thereof. . 7. The fabric softening composition of claim 6, wherein the fabric softening compounds are quaternary ammonium compounds. Fabric softening composition according to any one of the preceding claims, characterized in that it comprises 0.5% to 50% by weight of a cyclic polyol or reduced sugar, preferably 1% to 30% by weight. The fabric softening composition of any one of the preceding claims, wherein the composition comprises 0.0001% to 1% by weight of one or more of the antioxidants. The fabric softening composition according to any one of the preceding claims, wherein the weight ratio of the cyclic polyol or reduced sugar to the antioxidants or antioxidants is 50: 1 or greater, preferably 75: 1 or greater. -33 · ♦ • ♦ Fabric softening composition according to any one of the preceding claims, characterized in that it is a liquid, preferably an emulsion. A method of reducing odor in a composition comprising a cyclic polyol or reduced sugar as defined in claim 1, characterized in that at least one initiation inhibitor and at least one propagation inhibitor are added.