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EP1154068A1 - Softener composition - Google Patents

Softener composition Download PDF

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Publication number
EP1154068A1
EP1154068A1 EP00974874A EP00974874A EP1154068A1 EP 1154068 A1 EP1154068 A1 EP 1154068A1 EP 00974874 A EP00974874 A EP 00974874A EP 00974874 A EP00974874 A EP 00974874A EP 1154068 A1 EP1154068 A1 EP 1154068A1
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EP
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Prior art keywords
group
alkyl
weight
formula
represent
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EP00974874A
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German (de)
French (fr)
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EP1154068B1 (en
EP1154068A4 (en
Inventor
Hiromitsu Kao Corporation Research Labs. HAYASHI
Noriko Kao Corporation Research Labs. YAMAGUCHI
Shuji Kao Corporation Research Labs. TAGATA
Ikuo Kao Corporation Research Labs. SUGANO
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Kao Corp
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Kao Corp
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Priority claimed from JP2000102428A external-priority patent/JP3389549B2/en
Priority claimed from JP2000114097A external-priority patent/JP3389550B2/en
Application filed by Kao Corp filed Critical Kao Corp
Publication of EP1154068A1 publication Critical patent/EP1154068A1/en
Publication of EP1154068A4 publication Critical patent/EP1154068A4/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/835—Mixtures of non-ionic with cationic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/86—Mixtures of anionic, cationic, and non-ionic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or salts thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols

Definitions

  • the present invention relates to a softener composition.
  • JP-A 10-512015 discloses a softener composition comprising a water-insoluble quaternary ammonium salt as a softener and a water-soluble quaternary ammonium salt as an antimicrobial agent compounded therein.
  • JP-A 7-3649 discloses a fiber product-softener composition, having pH 2 to 5, comprising a di-long-chain-alkyl amine (C 6-24 alkyl or alkenyl group which may be interrupted by an ether linkage, ester linkage or acid amide linkage) and a mono-long-chain-alkyl quaternary ammonium salt (C 6-24 alkyl or alkenyl group which may be interrupted by an ether linkage, ester linkage or acid amide linkage), at a weight ratio of from 9 : 1 to 5 : 5.
  • a di-long-chain-alkyl amine C 6-24 alkyl or alkenyl group which may be interrupted by an ether linkage, ester linkage or acid amide linkage
  • a mono-long-chain-alkyl quaternary ammonium salt C 6-24 alkyl or alkenyl group which may be interrupted by an ether linkage, ester linkage or acid amide linkage
  • WO 98/56886 discloses an antimicrobial fiber softener composition, being suitable for conferring antimicrobial performance on fibers, comprising a conventional fiber softener composition and one or more cationic antimicrobial agents in a larger amount than required for antimicrobial performance. It, however, is a problem that the antimicrobial water-soluble quaternary ammonium salt lowers the softening effect. The softening effect is necessarily sacrificed in order to attain a satisfactory antimicrobial effect. In particular, it is difficult to achieve a composition demonstrating both a high softening effect and antimicrobial performance being capable of suppressing for long nasty smell attributable to microorganisms when clothes are dried in a room and body smell derived from sweat at the time of wearing.
  • the purpose of the present invention is to provide a softener composition which suppresses for long body smell derived from sweat etc. and is excellent in the softening effect.
  • the present invention relates to a softener composition
  • a softener composition comprising:
  • linkage refers to a covalent bond directly linking R 13 with R 17 .
  • the component (a) of the present invention is a compound having the formula (1): in which R 1 and R 2 independently represent a C 12-22 , preferably C 14-22 and more preferably C 14-18 alkyl or alkenyl group, X and Y independently represent a group selected from -COO-, -CONR 7 -, -OCO- and -NR 7 CO-, and preferably at least one of X and Y is -COO- or -OCO-; X and Y are preferably -COO- or -OCNR 7 -.
  • R 7 represents a hydrogen atom or a C 1-3 alkyl or hydroxyalkyl group.
  • R 3 and R 4 independently represent a C 1-5 alkylene group
  • R 5 and R 6 represent a C 1-3 alkyl or hydroxyalkyl group or R 1 -X-R 3 -
  • Z - is an anionic group.
  • Z - is preferably a halogen ion, sulfate ion, phosphate ion, a C 1-3 alkyl sulfate ion or a C 1-12 fatty acid ion.
  • the component (a) is particularly preferably the following compound.
  • R' and R'' may be the same as or different from each other and represent a C 12-18 alkyl or alkenyl group;
  • R''' is a C 1-3 alkyl or hydroxyalkyl group; and
  • R'''' is a C 1-3 alkyl group.
  • the component (b) of the present invention is a compound represented by formula (2) : wherein R 8 represents a C 12-22 , preferably C 14-22 and more preferably C 14-18 alkyl or alkenyl group, W is -COO-, -CONR 7 -, -OCO- or -NR 7 CO-, preferably -COO- or -OCNR 7 -.
  • R 7 represents a hydrogen atom or a C 1-3 alkyl or hydroxyalkyl group, preferably a hydrogen atom.
  • R 9 is a C 1-5 alkylene group and R 10 and R 11 independently represent a C 1-3 alkyl or hydroxyalkyl group.
  • R 12 is a C 1-3 alkyl group or -R 26 -OH.
  • R 26 is a C 1-5 alkylene group.
  • Z - is an anionic group, preferably a halogen ion, a fatty acid ion or a C 1-3 alkyl sulfate
  • the component (c) of the present invention is a compound of the formula (3) or (4) above shown.
  • the most preferable component (c) the following compounds can be exemplified.
  • Z - has the meanings as defined above.
  • R is a C 12-16 alkyl group.
  • R is an optionally branched C 6-10 alkyl group and m is an integer of 1 to 5.
  • R is a C 8-18 alkyl group.
  • the component (d) of the present invention is a compound of the formula (5) above shown and the anionic group represented by W of the formula (5) is preferably a sulfate ion, a halogen ion, a C 1-12 fatty acid ion or a C 1-3 alkyl sulfate ion.
  • the softener composition of the present invention comprises the component (a) in an amount of preferably 3 to 50 % by weight, more preferably 3 to 40 % by weight and particularly preferably 5 to 35 % by weight. Further, the amount of the component (b) is 0.5 to 10 % by weight, preferably 0.5 to 5 % by weight. In addition, it is preferable to the softening effect and the deodorizing effect that a weight ratio of the component (a)/the component (b) is from 80/20 to 99/1, particularly from 85/15 to 95/1.
  • the component (c) is contained in an amount of 0.1 to 15 % by weight, preferably 1 to 15 % by weight and particularly preferably 3 to 10 % by weight. Further, it is desirable to the feeling in touch of clothes and the deodorizing effect that the ratio of (c)/(a) by weight is from 1/30 to 1/1, preferably from 1/10 to 1/1.
  • the amount of the component (d) is preferably 0.1 to 15 % by weight, more preferably 0.2 to 10 % by weight, and a weight ratio of (a)/(d) is from 50/1 to 2/1, preferably from 30/1 to 2/1, and more preferably from 20/1 to 2/1.
  • the softener composition of the present invention is preferably in the form of an aqueous solution comprising at least the component (a) and the component (c) or the component (b) and the component (d), diluted in water.
  • the water used is preferably distilled water or deionized water. It is desirable for storage stability that water is incorporated in an amount of 40 to 90 % by weight, more preferably 50 to 85 % by weight and particularly preferably 60 to 85 % by weight into the composition.
  • composition of the present invention is adjusted to a pH value of 1 to 6, further 2 to 5, and particularly 2.5 to 4 at 20 °C.
  • the nonionic surfactant is preferably a polyoxyethylene alkyl ether containing one or more C 8-20 alkyl or alkenyl group, particularly preferably a nonionic surfactant of the formula (6): R 24 -U-[(R 25 O) p -H] q wherein R 24 is a C 10-18 , preferably C 12-18 , alkyl or alkenyl group, R 25 is a C 2 or C 3 alkylene group, preferably an ethylene group; p is an integer of 2 to 100, preferably 5 to 80, more preferably 10 to 80 and particularly preferably 20 to 60; and U is -O-, -CON- or -N-, and when U is -O-, q is 1, and when U is -CON-or -N-, q is 2.
  • the compound of the formula (6) includes for example the following compounds: R 24 -O- (C 2 H 4 O)r-H wherein R 24 has the same meanings as defined above; and when the component (c) is contained, r is an integer of 8 to 100, and when the component (d) is contained, r is an integer of 5 to 100, preferably 10 to 80 and more preferably 20 to 80.
  • R 24 -O- (C 2 H 4 O)s (C 3 H 6 O) t-H wherein R 24 has the same meanings as defined above; s and t are independently an integer of 2 to 40, preferably 5 to 40, and the sum of s and t is preferably an integer of 10 to 80, and the ethylene oxide and propylene oxide units may be a random-or block-addition product. wherein R 24 has the same meanings as defined above; and when the component (c) is contained, the sum in total of u and v is an integer of 5 to 100 and when the component (d) is contained, the sum in total thereof is an integer of 10 to 80, preferably 5 to 80.
  • the amount of the nonionic surfactant incorporated is 0.5 to 10 % by weight, preferably 1 to 8 % by weight.
  • a C 8-22 fatty acid or a salt thereof is preferably added in an amount of 0.1 to 5 % by weight, particularly 0.5 to 3 % by weight.
  • the fatty acid or a salt thereof includes caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid or a mixture thereof.
  • One or more members selected from lauric acid, stearic acid and oleic acid are particularly preferable.
  • fatty acids having an alkyl composition derived from coconut oil, palm oil, palm seed oil or tallow are also preferable.
  • an ester compound of a C 8-22 saturated or unsaturated fatty acid and a polyvalent alcohol is incorporated in an amount of 0.1 to 10 % by weight, particularly 0.5 to 5 % by weight into the composition.
  • the ester compound is preferably triglycerides, diglycerides, monoglyceride, a mono-, di- or tri-ester of pentaerythritol and sorbitan ester.
  • inorganic salts such as calcium chloride are added in an amount of 0 to 1000 ppm, preferably 1 to 1000 ppm, and more preferably 10 to 500 ppm.
  • Sodium salts and potassium salts are contained in surfactants such as fatty acid salts and the inorganic salts mixed in the composition by using such surfactants are not subject to the above limitation.
  • a solvent component selected from ethanol, isopropanol, glycerin, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol and polyoxyethylene phenyl ether is further preferably incorporated for storage stability.
  • These solvent components are incorporated in an amount of preferably 0 to 20 % by weight, more preferably 0.1 to 20 % by weight and particularly preferably 0.5 to 10 % by weight into the composition.
  • ethanol it is desirable to use a polyoxyethylene alkyl ether sulfate-modified ethanol or an 8-acetylated sucrose-modified ethanol.
  • silicone being ordinarily incorporated into a fiber-treating agent, a perfume (particularly preferably a combination of aroma components shown as the components (c) and (d) described in JP-A 8-11387) and a coloring matter may be incorporated into the softener composition of the present invention.
  • R: a mixed C 18 and C 16 saturated alkyl group (ratio by weight of C 18 group/C 16 group 60/40)
  • R: a mixed C 17 and C 15 saturated alkyl group (ratio by weight of C 17 group/C 15 group 60/40)
  • R: a mixted C 17 and C 15 saturated alkyl group (ratio by weight of C 17 group/C 15 group 60/40) (a-5) Dioleoyl hydroxyethyl dimethyl ammonium methyl sulfate.
  • R: a mixed C 18 and C 16 saturated alkyl group (ratio by weight of C 18 group/C 16 group 60/40)
  • R: a mixed C 17 and C 15 saturated alkyl group (ratio by weight of C 17 group/C 15 group 60/40) (d-1) Didecyl dimethyl ammonium chloride.
  • e-1) An addition product of a saturated alcohol containing 12 carbon atoms to which 21 moles on the average of ethylene oxide have been added.
  • (e-2) An addition product of lauric acid diethanolamide to which 20 moles on the average of ethylene oxide have been added.
  • (f-1) LunackTM S-50 (stearic acid produced by Kao Corporation).
  • (f-2) Lauric acid.
  • (f-3) Myristic acid.
  • (g-2) Calcium chloride.
  • (h-1) Coloring matter (Acid blue 9).
  • the softener compositions shown in Table 1 were prepared (invention products 1 to 6 and comparative products 1 to 3).
  • Two sweaters 100 % cotton
  • a washing machine two-tank system laundering machine VH-360S1 manufactured by Toshiba Corp.; detergent concentration, 0.0667 % by weight; 30 L tap water used; water temperature of 20 °C; 10 minutes
  • the washing water was discharged and the clothes were dehydrated for 1 minute.
  • 30 L tap water was poured into the tank, the clothes were rinsed for 5 minutes, the water was discharged, and the clothes were dehydrated for 1 minute.
  • the softener compositions of Table 1 and the corresponding compositions to them, except that the antimicrobial component, the component (c) or (d), was not added, were used in the softening treatment described above. They were evaluated in a paired comparison test using the following criteria by a panel of 10 persons to determine a ⁇ mean value.
  • the softener compositions (invention products 7 to 11) shown in Table 2 were prepared in the same manner as in Example 1.
  • As the perfume a mixture of 100 parts by weight of a composition of Table 3 and 10 parts by weight of dipropylene glycol was used.
  • These softener compositions were evaluated in the same manner as in Example 1. As results they were all recognized to exhibit an excellent smell-preventing effect and softening performance.
  • Perfume Ingredient (wt%) Perfume 1 Perfume 2 Perfume 3 Perfume 4 Perfume 5 hexyl cinnamic aldehyde 0 0 13 0 0 Nerolin yarayara 0 0 3 0 0 tricyclodecenyl acetate 0 0 3 0 0 benzyl acetate 0 0 7 0 0 musk ketone 0 0 3 0 0 0 anisyl acetone 0 0 1 0 0 0 0 0 Sandalmysore core 0 0 1 0 0 Aldehyde C14 peach 0 0 1 0 0 Metyl ionone- ⁇ 7 0 0 3 0 Iso E Super 7 0 0 3 0 Tentarome 14 0 0 7 0 4-t-butylcyclohexylacetate 14 0 0 7 0 Lilial 20 0
  • the softener compositions shown in Table 4 were prepared. Five shirts (100 % cotton) and 5 towels (100 % cotton) (total weight of the clothes: 1.5 kg) were washed using a commercial weakly alkaline detergent (AttackTM, Kao Corporation) in a laundry machine (two-tank system laundering machine VH-360S1 manufactured by Toshiba Corp.; detergent concentration, 0.0667 % by weight; 30 L tap water used; water temperature of 20 °C; 10 minutes) . Thereafter, the washing water was discharged and the clothes were dehydrated for 1 minute. After 30 L tap water was poured into the tank, the clothes were rinsed for 5 minutes, the water was discharged, and the clothes were dehydrated for 1 minute. Then, 30 L tap water was again poured into the tank and 7 ml of each composition of Table 1 was added thereto. It was stirred with the clothes for 5 minutes. Thereafter the clothes were dehydrated and air-dried.
  • AttackTM commercial weakly alkaline detergent
  • VH-360S1
  • the clothes treated as above were worn for 12 hours by 5 males aged twenties, and the smell generated from the shirts worn were judged using the following criteria by a panel of 10 persons (10 males aged thirties), to determine a mean value.
  • ⁇ was assigned to a mean value of less than 0.8, ⁇ to a mean value of 0.8 to less than 1.2, ⁇ to a mean value of 1.2 to less than 1.7, and X to a mean value of 1.7 or more. Results are shown in Table 1.

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Abstract

The purpose of the present invention is to provide a softener composition which suppresses for a long time body smell derived from sweat etc. and is excellent in the softening effect. That is, the present invention relates to a softener composition comprising:
  • (a) a quaternary ammonium compound represented by the formula (1) :
    Figure 80000001
    wherein R1 and R2 independently represent a C12-22 alkyl or alkenyl group, X and Y are independently -COO-, -CONR7-, -OCO- or - NR7CO-, provided that at least one of X and Y is -COO- or - OCO-, R7 represents a hydrogen atom or a C1-3 alkyl or hydroxyalkyl group, R3 and R4 independently represent a C1-5 alkylene group, R5 and R6 represent a C1-3 alkyl or hydroxyalkyl group or R1-X-R3- and Z- is an anionic group,
  • (b) a quaternary ammonium compound represented by the formula (2) :
    Figure 80000002
    wherein R8 represents a C12-22 alkyl or alkenyl group, W is a group selected from -COO-, -CONR7-, -OCO- and -NR7CO-, R7 represents a hydrogen atom or a C1-3 alkyl or hydroxyalkyl group, preferably a hydrogen atom, R9 represents a C1-5 alkylene group, R10 and R11 represent a C1-3 alkyl or hydroxyalkyl group, R12 represents a C1-3 alkyl group or -R26-OH, R26 is a C1-5 alkylene group and Z- is an anionic group, and
    a compound selected from the following component (c) or (d) :
  • (c) 0.1 to 15 % by weight of a compound represented by the formula (3) and/or formula (4) :
    Figure 80010001
    Figure 80010002
    wherein R13 and R18 independently represent a C5-19 alkyl or alkenyl group, R14 and R15 independently represent a C1-3 alkyl or hydroxyalkyl group and T is -COO-, -OCO-, -CONH-, -NHCO-,
    Figure 80010003
    or a linkage, R16 represents a C1-3 alkylene group, R17 represents a C1-6 alkylene group or -(O-R19)n-, R19 is ethylene group or propylene group and n is a number of 1 to 10 and W- is an anionic group, and
  • (d) 0.01 to 15 % by weight of a compound represented by the formula (5) :
    Figure 80020001
    wherein 2 or 3 groups out of R20, R21, R22 and R23 represent a C8-12 alkyl group, the remainder of them represent a C1-3 alkyl group, a C1-3 hydroxyalkyl group or a C7-15 arylalkyl group and Z- is an anionic group.
    •

    Description

    Technical Field
    The present invention relates to a softener composition.
    Background Art
    Heretofore, quaternary ammonium salts having long-chain alkyl group, acid salts of tertiary amines, etc. have been used for softeners. Further, compounding of a softener composition with an antimicrobial agent has been attempted for sanitation and deodorization of fiber products. JP-A 10-512015 discloses a softener composition comprising a water-insoluble quaternary ammonium salt as a softener and a water-soluble quaternary ammonium salt as an antimicrobial agent compounded therein. In addition, JP-A 7-3649 discloses a fiber product-softener composition, having pH 2 to 5, comprising a di-long-chain-alkyl amine (C6-24 alkyl or alkenyl group which may be interrupted by an ether linkage, ester linkage or acid amide linkage) and a mono-long-chain-alkyl quaternary ammonium salt (C6-24 alkyl or alkenyl group which may be interrupted by an ether linkage, ester linkage or acid amide linkage), at a weight ratio of from 9 : 1 to 5 : 5. WO 98/56886 discloses an antimicrobial fiber softener composition, being suitable for conferring antimicrobial performance on fibers, comprising a conventional fiber softener composition and one or more cationic antimicrobial agents in a larger amount than required for antimicrobial performance. It, however, is a problem that the antimicrobial water-soluble quaternary ammonium salt lowers the softening effect. The softening effect is necessarily sacrificed in order to attain a satisfactory antimicrobial effect. In particular, it is difficult to achieve a composition demonstrating both a high softening effect and antimicrobial performance being capable of suppressing for long nasty smell attributable to microorganisms when clothes are dried in a room and body smell derived from sweat at the time of wearing.
    Disclosure of Invention
    Accordingly, the purpose of the present invention is to provide a softener composition which suppresses for long body smell derived from sweat etc. and is excellent in the softening effect.
    The present invention relates to a softener composition comprising:
  • (a) a quaternary ammonium compound represented by the formula (1) :
    Figure 00020001
    wherein R1 and R2 independently represent a C12-22 alkyl or alkenyl group, X and Y are independently -COO-, -CONR7-, -OCO- or - NR7CO-, preferably provided that at least one of X and Y is -COO-or -OCO-. R7 represents a hydrogen atom or a C1-3 alkyl or hydroxyalkyl group. R3 and R4 independently represent a C1-5 alkylene group, R5 and R6 represent a C1-3 alkyl or hydroxyalkyl group or R1-X-R3-, and Z- is an anionic group,
  • (b) a quaternary ammonium compound represented by formula (2) :
    Figure 00030001
    wherein R8 represents a C12-22 alkyl or alkenyl group, W is a group selected from -COO-, -CONR7-, -OCO- and -NR7CO-, R7 represents a hydrogen atom or a C1-3 alkyl or hydroxyalkyl group, preferably a hydrogen atom, R9 represents a C1-5 alkylene group, R10 and R11 represent a C1-3 alkyl or hydroxyalkyl group, R12 represents a C1-3 alkyl group or -R26-OH, R26 is a C1-5 alkylene group and Z- is an anionic group, and
    a compound selected from the following component (c) or (d):
  • (c) 0.1 to 15 % by weight of a compound represented by formula (3) and/or formula (4):
    Figure 00030002
    Figure 00030003
    wherein R13 and R18 independently represent a C5-19 alkyl or alkenyl group, R14 and R15 independently represent a C1-3 alkyl or hydroxyalkyl group, and T is -COO-, -OCO-, -CONH-, -NHCO-,
    Figure 00040001
    or a linkage; R16 represents a C1-3 alkylene group, R17 represents a C1-6 alkylene group or -(O-R19)n, R19 is ethylene group or propylene group and n is a number of 1 to 10 and W- is an anionic group, and
  • (d) 0.01 to 15 % by weight, preferably 0.1 to 15 % by weight of a compound represented by formula (5):
    Figure 00040002
    wherein 2 or 3 groups of R20, R21, R22 and R23 represent a C8-12 alkyl group while the remainder(s) represents a C1-3 alky group, C1-3 hydroxyalkyl group or C7-15 arylalkyl group, and Z- is an anionic group.
    • As used herein, the "linkage" refers to a covalent bond directly linking R13 with R17.
    Best Mode for Carrying Out the Invention
    The component (a) of the present invention is a compound having the formula (1):
    Figure 00040003
    in which R1 and R2 independently represent a C12-22, preferably C14-22 and more preferably C14-18 alkyl or alkenyl group, X and Y independently represent a group selected from -COO-, -CONR7-, -OCO- and -NR7CO-, and preferably at least one of X and Y is -COO- or -OCO-; X and Y are preferably -COO- or -OCNR7-. R7 represents a hydrogen atom or a C1-3 alkyl or hydroxyalkyl group. R3 and R4 independently represent a C1-5 alkylene group, R5 and R6 represent a C1-3 alkyl or hydroxyalkyl group or R1-X-R3-, and Z- is an anionic group. Z- is preferably a halogen ion, sulfate ion, phosphate ion, a C1-3 alkyl sulfate ion or a C1-12 fatty acid ion.
    The component (a) is particularly preferably the following compound.
    Figure 00050001
    R' and R'' may be the same as or different from each other and represent a C12-18 alkyl or alkenyl group; R''' is a C1-3 alkyl or hydroxyalkyl group; and R'''' is a C1-3 alkyl group.
    The component (b) of the present invention is a compound represented by formula (2) :
    Figure 00050002
    wherein R8 represents a C12-22, preferably C14-22 and more preferably C14-18 alkyl or alkenyl group, W is -COO-, -CONR7-, -OCO- or -NR7CO-, preferably -COO- or -OCNR7-. R7 represents a hydrogen atom or a C1-3 alkyl or hydroxyalkyl group, preferably a hydrogen atom. R9 is a C1-5 alkylene group and R10 and R11 independently represent a C1-3 alkyl or hydroxyalkyl group. R12 is a C1-3 alkyl group or -R26-OH. R26 is a C1-5 alkylene group. Z- is an anionic group, preferably a halogen ion, a fatty acid ion or a C1-3 alkyl sulfate ion.
    The component (c) of the present invention is a compound of the formula (3) or (4) above shown. As the most preferable component (c), the following compounds can be exemplified. In the formulae, Z- has the meanings as defined above.
    Figure 00060001
    (R is a C12-16 alkyl group.)
    Figure 00060002
    (R is an optionally branched C6-10 alkyl group and m is an integer of 1 to 5.)
    Figure 00060003
    (R is a C8-18 alkyl group.)
    The component (d) of the present invention is a compound of the formula (5) above shown and the anionic group represented by W of the formula (5) is preferably a sulfate ion, a halogen ion, a C1-12 fatty acid ion or a C1-3 alkyl sulfate ion.
    (Softener composition)
    The softener composition of the present invention comprises the component (a) in an amount of preferably 3 to 50 % by weight, more preferably 3 to 40 % by weight and particularly preferably 5 to 35 % by weight. Further, the amount of the component (b) is 0.5 to 10 % by weight, preferably 0.5 to 5 % by weight. In addition, it is preferable to the softening effect and the deodorizing effect that a weight ratio of the component (a)/the component (b) is from 80/20 to 99/1, particularly from 85/15 to 95/1.
    When the component (c) is used in the present invention, the component (c) is contained in an amount of 0.1 to 15 % by weight, preferably 1 to 15 % by weight and particularly preferably 3 to 10 % by weight. Further, it is desirable to the feeling in touch of clothes and the deodorizing effect that the ratio of (c)/(a) by weight is from 1/30 to 1/1, preferably from 1/10 to 1/1. Further, when the component (d) is used in the present invention, it is desirable to the feeling in touch of clothes and the deodorizing effect that the amount of the component (d) is preferably 0.1 to 15 % by weight, more preferably 0.2 to 10 % by weight, and a weight ratio of (a)/(d) is from 50/1 to 2/1, preferably from 30/1 to 2/1, and more preferably from 20/1 to 2/1.
    The softener composition of the present invention is preferably in the form of an aqueous solution comprising at least the component (a) and the component (c) or the component (b) and the component (d), diluted in water. The water used is preferably distilled water or deionized water. It is desirable for storage stability that water is incorporated in an amount of 40 to 90 % by weight, more preferably 50 to 85 % by weight and particularly preferably 60 to 85 % by weight into the composition.
    Further, it is preferable to the deodorizing effect and for storage stability that the composition of the present invention is adjusted to a pH value of 1 to 6, further 2 to 5, and particularly 2.5 to 4 at 20 °C.
    In the present invention, incorporation of a nonionic surfactant (e) in addition to the above components (a), (b), (c) and (d) is preferable for storage stability. The nonionic surfactant is preferably a polyoxyethylene alkyl ether containing one or more C8-20 alkyl or alkenyl group, particularly preferably a nonionic surfactant of the formula (6): R24-U-[(R25O)p-H] q wherein R24 is a C10-18, preferably C12-18, alkyl or alkenyl group, R25 is a C2 or C3 alkylene group, preferably an ethylene group; p is an integer of 2 to 100, preferably 5 to 80, more preferably 10 to 80 and particularly preferably 20 to 60; and U is -O-, -CON- or -N-, and when U is -O-, q is 1, and when U is -CON-or -N-, q is 2.
    The compound of the formula (6) includes for example the following compounds: R24-O- (C2H4O)r-H wherein R24 has the same meanings as defined above; and when the component (c) is contained, r is an integer of 8 to 100, and when the component (d) is contained, r is an integer of 5 to 100, preferably 10 to 80 and more preferably 20 to 80. R24-O- (C2H4O)s (C3H6O) t-H wherein R24 has the same meanings as defined above; s and t are independently an integer of 2 to 40, preferably 5 to 40, and the sum of s and t is preferably an integer of 10 to 80, and the ethylene oxide and propylene oxide units may be a random-or block-addition product.
    Figure 00090001
    wherein R24 has the same meanings as defined above; and when the component (c) is contained, the sum in total of u and v is an integer of 5 to 100 and when the component (d) is contained, the sum in total thereof is an integer of 10 to 80, preferably 5 to 80.
    From the viewpoint of stability, the amount of the nonionic surfactant incorporated is 0.5 to 10 % by weight, preferably 1 to 8 % by weight.
    For the purpose of improving the feeling in touch of fiber products, in the present invention, (f) a C8-22 fatty acid or a salt thereof is preferably added in an amount of 0.1 to 5 % by weight, particularly 0.5 to 3 % by weight.
    The fatty acid or a salt thereof includes caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid or a mixture thereof. One or more members selected from lauric acid, stearic acid and oleic acid are particularly preferable. Further, fatty acids having an alkyl composition derived from coconut oil, palm oil, palm seed oil or tallow are also preferable.
    In the present invention, it is preferable for storage stability that an ester compound of a C8-22 saturated or unsaturated fatty acid and a polyvalent alcohol is incorporated in an amount of 0.1 to 10 % by weight, particularly 0.5 to 5 % by weight into the composition. The ester compound is preferably triglycerides, diglycerides, monoglyceride, a mono-, di- or tri-ester of pentaerythritol and sorbitan ester.
    In the present invention, it is desirable for storage stability that inorganic salts such as calcium chloride are added in an amount of 0 to 1000 ppm, preferably 1 to 1000 ppm, and more preferably 10 to 500 ppm. Sodium salts and potassium salts are contained in surfactants such as fatty acid salts and the inorganic salts mixed in the composition by using such surfactants are not subject to the above limitation.
    In the present invention, a solvent component selected from ethanol, isopropanol, glycerin, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol and polyoxyethylene phenyl ether is further preferably incorporated for storage stability. These solvent components are incorporated in an amount of preferably 0 to 20 % by weight, more preferably 0.1 to 20 % by weight and particularly preferably 0.5 to 10 % by weight into the composition. If ethanol is used, it is desirable to use a polyoxyethylene alkyl ether sulfate-modified ethanol or an 8-acetylated sucrose-modified ethanol.
    Ingredients such as silicone being ordinarily incorporated into a fiber-treating agent, a perfume (particularly preferably a combination of aroma components shown as the components (c) and (d) described in JP-A 8-11387) and a coloring matter may be incorporated into the softener composition of the present invention.
    Examples <Compounding ingredients>
    The ingredients used in the present invention are shown below.
    Figure 00110001
    R: a mixed C18 and C16 saturated alkyl group (ratio by weight of C18 group/C16 group = 60/40)
    Figure 00120001
    R: a mixed C18 and C16 saturated alkyl group (ratio by weight of C18 group/C16 group = 60/40)
    Figure 00120002
    R: a mixed C17 and C15 saturated alkyl group (ratio by weight of C17 group/C15 group = 60/40)
    Figure 00120003
    R: a mixted C17 and C15 saturated alkyl group (ratio by weight of C17 group/C15 group = 60/40)
    (a-5) Dioleoyl hydroxyethyl dimethyl ammonium methyl sulfate.
    Figure 00120004
    R: a mixed C17 and C15 saturated alkyl group (ratio by weight of C17 group/C15 group = 60/40)
    (a'-1) Dioleyl dimethyl ammonium chloride.
    Figure 00130001
    R: a mixed C18 and C16 saturated alkyl group (ratio by weight of C18 group/C16 group = 60/40)
    Figure 00130002
    R: a mixed C17 and C15 saturated alkyl group (ratio by weight of C17 group/C15 group = 60/40)
    Figure 00130003
    Figure 00130004
    Figure 00130005
    (d-1) Didecyl dimethyl ammonium chloride.
    (e-1) An addition product of a saturated alcohol containing 12 carbon atoms to which 21 moles on the average of ethylene oxide have been added.
    (e-2) An addition product of lauric acid diethanolamide to which 20 moles on the average of ethylene oxide have been added.
    (f-1) Lunack™ S-50 (stearic acid produced by Kao Corporation).
    (f-2) Lauric acid.
    (f-3) Myristic acid.
    (f-4) Palmitic acid.
    (g-1) Excel™ 150 [a mixture of stearic mono-, di- and
    triglycerides (mono : di : tri = 60 : 35 : 5) produced by Kao Corporation].
    (g-2) Calcium chloride.
    (g-3) Ethylene glycol.
    (h-1) Coloring matter (Acid blue 9).
    (h-2) Perfume [a mixture of hexyl cinnamic aldehyde (18), nerolin yarayara (4), tricyclodecenyl acetate (4), benzyl acetate (10), musk ketone (5), anisyl acetone (2), sandal mysolcore (2), aldehyde C14 peach (1), linalool (18), dihydroxy myrcenol (8), borneol (4), cedrol (4), mugoal (5), benzyl alcohol (5) and dipropylene glycol (10), the figures shown in the parentheses meaning a percent by weight in the perfume mixture.].
    (h-3) Silicone (TSA730 produced by Toshiba Silicone Co., Ltd.). Example 1
    Using the above compounds, the softener compositions shown in Table 1 were prepared (invention products 1 to 6 and comparative products 1 to 3). Two sweaters (100 % cotton) were washed using a commercial weakly alkaline detergent (Attack™, Kao Corporation) in a laundering machine (two-tank system laundering machine VH-360S1 manufactured by Toshiba Corp.; detergent concentration, 0.0667 % by weight; 30 L tap water used; water temperature of 20 °C; 10 minutes) . Thereafter, the washing water was discharged and the clothes were dehydrated for 1 minute. After 30 L tap water was poured into the tank, the clothes were rinsed for 5 minutes, the water was discharged, and the clothes were dehydrated for 1 minute. Then, 30 L tap water was again poured into the tank, and 5 g of each softener composition of Table 1 was added thereto. It was stirred for 5 minutes. Thereafter, the clothes were dehydrated and dried for 12 hours in a thermostatic chamber at 70 % RH at 25 °C.
    (Evaluation of softening performance)
    The softener compositions of Table 1 and the corresponding compositions to them, except that the antimicrobial component, the component (c) or (d), was not added, were used in the softening treatment described above. They were evaluated in a paired comparison test using the following criteria by a panel of 10 persons to determine a·mean value.
  • +1: Finished to be the softer in the presence of component (c) or (d).
  • 0: No difference in finish regardless of the presence or absence of the component (c) or (d).
  • -1: Finished to be the softer in the absence of the component (c) or (d).
    • (Evaluation of smell)
    The smell of the clothes dried in a thermostatic chamber and the smell of the same clothes worn for 12 hours by 5 males, aged twenties, were judged using the following criteria by a panel of 10 persons (10 males aged thirties), to determine a mean value.
    0:
    Hardly smelled.
    1:
    Slightly smelled but not annoying.
    2:
    Smelled.
    3:
    Significantly smelled.
    Figure 00170001
    Example 2
    The softener compositions (invention products 7 to 11) shown in Table 2 were prepared in the same manner as in Example 1. As the perfume, a mixture of 100 parts by weight of a composition of Table 3 and 10 parts by weight of dipropylene glycol was used. These softener compositions were evaluated in the same manner as in Example 1. As results they were all recognized to exhibit an excellent smell-preventing effect and softening performance.
    Figure 00180001
    Perfume Ingredient (wt%) Perfume 1 Perfume 2 Perfume 3 Perfume 4 Perfume 5
    hexyl cinnamic aldehyde 0 0 13 0 0
    Nerolin yarayara 0 0 3 0 0
    tricyclodecenyl acetate 0 0 3 0 0
    benzyl acetate 0 0 7 0 0
    musk ketone 0 0 3 0 0
    anisyl acetone 0 0 1 0 0
    Sandalmysore core 0 0 1 0 0
    Aldehyde C14 peach 0 0 1 0 0
    Metyl ionone-γ 7 0 0 3 0
    Iso E Super 7 0 0 3 0
    Tentarome 14 0 0 7 0
    4-t-butylcyclohexylacetate 14 0 0 7 0
    Lilial 20 0 0 10 0
    Herional 3 0 0 2 0
    coumarin 3 0 0 1 0
    Ambroxan 1 0 0 0 0
    α-Terpinyl acetate 0 12 0 0 20
    cedryl acetate 0 8 0 0 13
    Lyral 0 8 0 0 13
    Pearlide 0 4 0 0 7
    Sandal synth 0 4 0 0 7
    phenylacetoaldehyde 50% PEA 0 0 0 0 1
    aldehyde C12MNA 0 0 0 0 1
    cinnamyl cinnamate 0 2 0 0 3
    benzyl isoeugenol 0 2 0 0 3
    linalool 0 0 0 0 13
    dihydromyrcenol 0 0 0 0 7
    borneol 0 0 0 0 3
    cedrol 0 0 0 0 3
    Muguol 0 0 0 0 3
    benzyl alcohol 0 0 0 0 3
    phenylethyl alcohol 12 0 29 0 0
    citronellol 6 0 13 0 0
    terpineol 6 0 13 0 0
    phenylethyldimethyl carbinol 3 0 7 0 0
    styrallyl alcohol 2 0 3 0 0
    cinnamic alcohol 2 0 3 0 0
    1-menthol 0 24 0 27 0
    geraniol 0 12 0 13 0
    dihydromyrcenol 0 12 0 13 0
    Phenyl hexanol 0 6 0 7 0
    dimethylbenzyl carbinol 0 6 0 7 0
    Total (wt%) 100 100 100 100 100
    Example 3
    Using the above compounds, the softener compositions shown in Table 4 were prepared. Five shirts (100 % cotton) and 5 towels (100 % cotton) (total weight of the clothes: 1.5 kg) were washed using a commercial weakly alkaline detergent (Attack™, Kao Corporation) in a laundry machine (two-tank system laundering machine VH-360S1 manufactured by Toshiba Corp.; detergent concentration, 0.0667 % by weight; 30 L tap water used; water temperature of 20 °C; 10 minutes) . Thereafter, the washing water was discharged and the clothes were dehydrated for 1 minute. After 30 L tap water was poured into the tank, the clothes were rinsed for 5 minutes, the water was discharged, and the clothes were dehydrated for 1 minute. Then, 30 L tap water was again poured into the tank and 7 ml of each composition of Table 1 was added thereto. It was stirred with the clothes for 5 minutes. Thereafter the clothes were dehydrated and air-dried.
    (Evaluation of deodorizing effect)
    The clothes treated as above were worn for 12 hours by 5 males aged twenties, and the smell generated from the shirts worn were judged using the following criteria by a panel of 10 persons (10 males aged thirties), to determine a mean value. ○ was assigned to a mean value of less than 0.8, □ to a mean value of 0.8 to less than 1.2, Δ to a mean value of 1.2 to less than 1.7, and X to a mean value of 1.7 or more. Results are shown in Table 1.
    0:
    Hardly smelled.
    1:
    Slightly smelled but not annoying.
    2:
    Smelled.
    3:
    Significantly smelled.
    (Evaluation of softness)
    The towels treated as above and towels (control) treated in the same way, except for using no composition of Table 4, were judged using the following criteria by a panel of 10 persons (10 males aged thirties), to determine a mean value. ○ was assigned to a mean value of 2 or more, □ to a mean value of 1 to less than 1.5, Δ to a mean value of 0.5 to less than 1, and X to a mean value of less than 0.5. Results are shown in Table 1.
  • +3: much softer than the control.
  • +2: Softer than the control.
  • +1: Slightly softer than the control.
  • 0: Equal to the control.
    • Figure 00220001

    Claims (3)

    1. A softener composition comprising:
      (a) a quaternary ammonium compound represented by the formula (1) :
      Figure 00230001
      wherein R1 and R2 independently represent a C12-22 alkyl or alkenyl group, X and Y are independently -COO-, -CONR7-, -OCO- or - NR7CO-, provided that at least one of X and Y is -COO- or - OCO-, R7 represents a hydrogen atom or a C1-3 alkyl or hydroxyalkyl group, R3 and R4 independently represent a C1-5 alkylene group, R5 and R6 represent a C1-3 alkyl or hydroxyalkyl group or R1-X-R3- and Z- is an anionic group,
      (b) a quaternary ammonium compound represented by the formula (2) :
      Figure 00230002
      wherein R8 represents a C12-22 alkyl or alkenyl group, W is a group selected from -COO-, -CONR7-, -OCO- and -NR7CO-, R7 represents a hydrogen atom or a C1-3 alkyl or hydroxyalkyl group, preferably a hydrogen atom, R9 represents a C1-5 alkylene group, R10 and R11 represent a C1-3 alkyl or hydroxyalkyl group, R12 represents a C1-3 alkyl group or -R26-OH, R26 is a C1-5 alkylene group and Z- is an anionic group, and
      a compound selected from the following component (c) or (d) :
      (c) 0.1 to 15 % by weight of a compound represented by formula (3) and/or formula (4):
      Figure 00240001
      Figure 00240002
      wherein R13 and R18 independently represent a C5-19 alkyl or alkenyl group, R14 and R15 independently represent a C1-3 alkyl or hydroxyalkyl group, and T is -COO-, -OCO-, -CONH-, -NHCO-,
      Figure 00240003
      or a linkage, R16 represents a C1-3 alkylene group, R17 represents a C1-6 alkylene group or -(O-R19)n-, R19 is ethylene group or propylene group and n is a number of 1 to 10 and W- is an anionic group, and
      (d) 0.01 to 15 % by weight of a compound represented by formula (5) :
      Figure 00240004
      wherein 2 or 3 groups out of R20, R21, R22 and R23 represent a C8-12 alkyl group, the remainder of them represent a C1-3 alkyl group, a C1-3 hydroxyalkyl group or a C7-15 arylalkyl group and Z- is an anionic group.
    2. The softener composition according to claim 1, which further comprises (e) a nonionic surfactant.
    3. The softener composition according to claim 1 or 2, which further comprises 0.1 to 5 % by weight of (f) a C8-22 fatty acid or a salt thereof.
    EP00974874A 1999-11-12 2000-11-09 Softener composition Expired - Lifetime EP1154068B1 (en)

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    JP2000114097A JP3389550B2 (en) 2000-04-14 2000-04-14 Softener composition
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    EP2134825A4 (en) * 2007-03-13 2011-10-19 Elementis Specialties Inc Biodegradable cleaning compositions

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    JP5394215B2 (en) 2008-12-11 2014-01-22 花王株式会社 Softener composition

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    DE2928141A1 (en) * 1979-07-12 1981-02-05 Hoechst Ag SOFT SOFTENER
    JPH03287867A (en) * 1990-03-30 1991-12-18 Kao Corp Flexibilizing finish
    JP2970132B2 (en) * 1991-10-04 1999-11-02 ライオン株式会社 Liquid softener composition
    CN1066188C (en) * 1993-03-01 2001-05-23 普罗格特-甘布尔公司 Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing medium iodine value unsaturated fatty acid chains
    US5399272A (en) * 1993-12-17 1995-03-21 The Procter & Gamble Company Clear or translucent, concentrated biodgradable quaternary ammonium fabric softener compositions
    JP3476608B2 (en) * 1995-11-13 2003-12-10 花王株式会社 Soft finish composition
    IL121037A0 (en) * 1997-06-09 1997-11-20 Innoscent Ltd Laundry fabric softener which inhibits bacterial growth and odor formation
    JPH1161640A (en) * 1997-08-06 1999-03-05 Nof Corp Softening agent composition

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    * Cited by examiner, † Cited by third party
    Publication number Priority date Publication date Assignee Title
    EP2134825A4 (en) * 2007-03-13 2011-10-19 Elementis Specialties Inc Biodegradable cleaning compositions

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    WO2001036737A1 (en) 2001-05-25
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