WO1997008286A1 - Agent facilitant l'elimination des salissures et son utilisation dans des compositions de conditionnement de tissus - Google Patents

Agent facilitant l'elimination des salissures et son utilisation dans des compositions de conditionnement de tissus Download PDF

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Publication number
WO1997008286A1
WO1997008286A1 PCT/EP1996/003248 EP9603248W WO9708286A1 WO 1997008286 A1 WO1997008286 A1 WO 1997008286A1 EP 9603248 W EP9603248 W EP 9603248W WO 9708286 A1 WO9708286 A1 WO 9708286A1
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WO
WIPO (PCT)
Prior art keywords
groups
formula
integer
group
carbon atoms
Prior art date
Application number
PCT/EP1996/003248
Other languages
English (en)
Inventor
Abid Nadim Khan-Lodhi
Christopher Whaley
Original Assignee
Unilever Plc
Unilever N.V.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Unilever Plc, Unilever N.V. filed Critical Unilever Plc
Priority to EP96927048A priority Critical patent/EP0848748A1/fr
Priority to AU67016/96A priority patent/AU6701696A/en
Priority to BR9610021A priority patent/BR9610021A/pt
Publication of WO1997008286A1 publication Critical patent/WO1997008286A1/fr

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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
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0036—Soil deposition preventing compositions; Antiredeposition agents
    • 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
    • C11D1/38—Cationic compounds
    • C11D1/645—Mixtures of compounds all of which are cationic
    • 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

Definitions

  • the present invention relates to the use of a biodegradable quaternary ammonium material as a soil release agent, for example, in a fabric conditioning composition.
  • Rinse added fabric softener compositions are well known. Typically such compositions contain a water insoluble quaternary ammonium fabric softening agent dispersed in water at a level of softening agent up to 7% by weight in which case the compositions are considered dilute, or at levels from 7% to 50% in which case the compositions are considered concentrates.
  • fabric softening compositions desirably have other benefits. One is the ability to confer soil release properties to fabrics, particularly those woven from polyester or cotton fibres.
  • Soil release properties are generally imparted to fabrics by the use of a separate soil-release agent, usually a high molecular weight polymer, in a detergent composition or separate treatment.
  • a separate soil-release agent usually a high molecular weight polymer
  • a cationic polymeric soil release agent for use in a fabric conditioning composition.
  • a disadvantage of such compositions is that the soil release agent increases the number of components in the formulation, increasing cost and making the product less environmentally acceptable.
  • EP 0,234,311A (Henkel) describes the use of insoluble polyfunctional quaternary ammonium compounds as soil collectors, to regenerate soil-laden detergent solutions. The document contains no specific mention of the quaternary ammonium materials to which the present invention relates.
  • EP 0,309,052 (Procter and Gamble) describes the use of quaternary ammonium salts containing at least one ester linkage as softeners in shelf-stable and biodegradable fabric softening compositions. The compositions also include a linear alkoxylated alcohol.
  • EP 0,506,312 discloses the use as a soil release agent of a quaternary ammonium material comprising a compound having two C 12 . 18 alkyl or alkenyl groups connected via an ester link to a hydrocarbon chain which is connected to the quaternary nitrogen atom.
  • A is an (m + n) valent radical remaining after the removal of (m + n) hydroxy groups from an aliphatic polyol having p hydroxy groups and an atomic ration of carbon to oxygen in the range of 1,0 to 3,0 and up to 2 groups per hydroxy group selected from ethylene oxide and propylene oxide.
  • A is an (m + n) valent radical remaining after the removal of (m + n) hydroxy groups from an aliphatic polyol having p hydroxy groups and an atomic ration of carbon to oxygen in the range of 1,0 to 3,0 and up to 2 groups per hydroxy group selected from ethylene oxide and propylene oxide.
  • B is an alkylene or alkylidene group containing 1 to 4 carbon atoms
  • R 1 , R 2 , R 3 and R 4 are, independently from each other, straight or branched chain C ⁇ - C 48 alkyl or alkenyl groups, optionally with substitution by one ore more functional groups and/or interruption by at most 10 ethylene oxide and/or propylene oxide groups, or by at most two functional groups selected from O O O O O O
  • R 2 and R 3 may form a ring system containing 5 or 6 atoms in the ring, with the proviso that the average compound either has at least one R group having 22-48 carbon atoms, or at least two R groups having 16-20 carbon atoms, or at least three R groups having 10-14 carbon atoms.
  • the invention also provides the use as a soil release agent of a hydrolysis product of a compound of formula I.
  • the invention further provides a fabric conditioning composition comprising:
  • R 4 Formula I wherein X is an anion, A is an (m+n) valent radical remaining after the removal of (m+n) hydroxy groups from an aliphatic polyol having p hydroxy groups and an atomic ratio of carbon to oxygen in the range of 1,0 to 3,0 and up to 2 groups per hydroxy group selected from ethylene oxide and propylene oxide, 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 group containing 1 to 4 carbon atoms, R 1 , R 2 , R 3 and R 4 are, independently from each other straight or branched chain C -C 48 alkyl or alkenyl groups, optionally with substitution by one or more functional groups and/or interruption by at most 10 ethylene oxide and/or propylene oxide groups or by at most two functional groups selected from
  • R 2 and R 3 may form a ring system containing 5 or 6 atoms in the ring, with the proviso that the average compound has at least one R group having 22-48 carbon atoms, or at least two R groups having 16-20 carbon atoms, or at least three R groups having 10-14 carbon atoms.
  • X " represents a halide anion, more particularly a chloride, sulphate, methosulphate, carboxylate or sulphonate anion.
  • the compound of formula I is composed of: a) 1 equivalent of an aliphatic polyol having p hydroxy groups. b) m equivalents of an aliphatic carboxylic acid of the formula R I COOH, and c) n equivalents of a C 1-4 halocarboxylic acid, d) n equivalents of a tertiary amine of the formula R 2 R 3 R 4 N or n equivalents of a secondary amine of the formula R 2 R 3 H, converted with n equivalents of a quaternizing agent.
  • compositions comprising compounds corresponding to the first structural formula obtainable by reaction of a polyol having 2 to 8 hydroxy groups.
  • Optimum results are obtained when the polyol is selected from the group of ethyleneglycol, glycerol, pentaerythritol, sorbitol, glucose, saccharose, methylglucoside, and/or condensed derivatives thereof.
  • the polyol may be partially etherified and/or esterified.
  • ester forming derivative of the polyol or the carboxylic acid is a natural fat, preferably a glyceride.
  • condensed derivatives according to the invention are diglycerol, triglycerol, and dipentaerythritol.
  • Use may also be made of natural polyols such as starch, degraded starch, and oligomers and/or polymers containing repeating units of vinyl alcohol.
  • compositions comprising compounds corresponding to the first structural formula are obtainable by reacting of an aliphatic carboxylic acid of the formula R 1 -COOH or an ester thereof. Optimum results are obtained when said acid is tallow acid and/or at least partially hydrogenated tallow acid.
  • suitable quaternary ammonium compounds corresponding to the first structural formula are obtained by replacing tallow acid with, e.g., coconut acid, palmitic acid, lauric acid, oleic acid, stearic acid, or the like.
  • R 2 , R 3 , and R 4 groups are, independently from each other, straight or branched chain C 1 -C 48 alkyl or alkenyl groups, optionally with substitution by one or more functional groups and/or interruption by at most 10 ethylene oxide and/or propylene oxide groups, or by at most two functional groups selected from:
  • R 2 and R 3 may form a ring system containing 5 or 6 atoms in the ring .
  • Typical combinations of R 2 /R 3 /R 4 are :
  • R 2 , R 3 and R 4 groups can be introduced into the molecule by the use of appropriate tertiary amines such as trimethylamine, (hydrogenated) tallow fatty acid ester of
  • N,N-dimethylethanolamine (hydrogenated) tallow alcohol ester of N,N-dimethylglycine, (hydrogenated) tallow fatty acid amide of N,N-dimethylaminopropylamine, and dimethyl
  • the R 2 and R 3 groups can also be introduced by the use of appropriate secondary amines such as dimethylamine.
  • the R 4 group can then be introduced by quaternization of the thus obtained tertiary amine with halogenating agents such as methyl chloride and dimethylsulphate.
  • Tallow is a convenient and inexpensive source of long chain alkyl and alkenyl material.
  • PEQs polyolesterquats
  • the invention also provide the use of hydrolysis products of compounds of formula I as soil release agents.
  • Hydrophobic surfactants of general formula II are Hydrophobic surfactants of general formula II:
  • Preferred hydrolysis products are glycerol and pentaerythritol partial esters, especially glycerol mono-/di- stearate.
  • R is C 12 to C 18 .
  • hydrolysis products of formula I are zwitterionic.
  • the invention works particularly well when the PEQs and the hydrolysis products thereof are used in rinse conditioners. It is preferred if the rinse conditioners are liquids.
  • the invention may contain more conventional cationic softening compounds. It is advantageous if the cationic softening compound is a quaternary ammonium softening compound having a solubility in water at pH 2.5 and 20°C of less than lOg/1.
  • the cationic softening compound is a quaternary ammonium compound in which at least one long chain alkyl group is connected to the quaternary ammonium group via at least one ester link.
  • Preferred cationic softening compounds for use with the invention are compounds of formula (IV)
  • each R 5 group is independently selected from C ⁇ alkyl, alkenyl or hydroxalkyl groups; and wherein each R 6 group is independently selected from C 8 , 28 alkyl or alkenyl groups;
  • T is - O - C - or - C - O - ;
  • n is an integer from 0-5; and Y " is an anion. Also preferred are fabric conditioning compounds of formula (V)
  • each R 8 is independently selected from C ⁇ ,, alkyl, alkenyl or hydroxyalkyl groups; each R 9 is independently selected from C 8-28 alkyl or alkenyl groups; n is an integer from 0-5; and Y " is an anion.
  • the level of ester linked quaternary ammonium compounds is at least 1% by weight of the composition, more preferably more than 3% by weight of the composition; especially interesting are concentrated compositions which comprise more than 7% of ester-linked quaternary ammonium compound.
  • the level of ester-linked quaternary ammonium compounds preferably is between 1% and 80% by weight, more preferably 3% to 50%, most preferably 8% to 50%.
  • the composition can also contain one or more optional ingredients, selected from non-aqueous solvents, pH buffering agents, perfumes, perfume carriers, fluorescers, colorants, hydrotropes, antifoaming agents, antiredeposition agents, enzymes, optical brightening agents, opacifiers, anti- shrinking agents, anti-wrinkle agents, anti-spotting agents, germicides, fungicides, anti-oxidants, anti-corrosion agents, drape imparting agents, antistatic agents and ironing aids.
  • the composition may also contain nonionic fabric softening agents such as lanolin and derivatives thereof.
  • the softening composition may be stabilised at low temperatures by the addition of nonionic stabilisers.
  • Suitable nonionic stabilisers which can be used include the condensation products of C ⁇ -C 22 primary linear alcohols with 10 to 20 moles of ethylene oxide.
  • the alcohols may be saturated or unsaturated.
  • the level of nonionic stabiliser is within the range from 0.1 to 10% by weight, more preferably from 0.5 to 5% by weight, most preferably from 1 to 4% by weight.
  • the mole ratio of the quaternary ammonium compound to the nonionic stabilising agent is within the range from 40:1 to about 1:1, preferably within the range from 18.1 to about 3:1.
  • the composition can also contain fatty acids for example C 8 - C 24 alkyl or alkenyl monocarboxylic acids or polymers thereof.
  • fatty acids for example C 8 - C 24 alkyl or alkenyl monocarboxylic acids or polymers thereof.
  • saturated fatty acids are used, in particular, hardened tallow C 16 -C 18 fatty acids.
  • the fatty acid is non-saponified, more preferably the fatty acid is free for example oleic acid, lauric acid or tallow fatty acid.
  • the level of fatty acid material is preferably more than 0.1% by weight, more preferably more than 0.2% by weight. Especially preferred are concentrates comprising from 0.5 to 20% by weight of fatty acid, more preferably 1% to 10% by weight.
  • the weight ratio of quaternary ammonium material to fatty acid material is preferably from 50:1 to 1:10.
  • the compositions of the invention preferably have a pH in the range 1.2 to 5, more preferably a pH from 1.5 to 4.
  • Liquid fabric softening compositions were made as follows. The following materials were made up as 1% w/w dispersions of active material in demineralised water by heating the mixtures at 70°C, with occasional agitation, until homogeneous. Asterisks indicate Trade Marks.
  • Raw material contained 85% quat. , 2% fatty acid, and 13% isopropanol.
  • Raw material contained 80% quat., 20% solvent.
  • Raw material contained 90% quat., 10% solvent.
  • the soil release benefits of the various treatments were determined using the following method.
  • 16 3" x 3" cotton sheeting or knitted polyester squares were treated in a tergotometer pot (ambient temperature, 60 rpm) with 10 ml of a 1% w/w dispersion of the required material in IL of water. After 10 minutes, the fabric squares were removed and spun and line dried.
  • Table 1 shows the detergency results of the fabric softening compounds of the prior art. Results are for removal of oily soil from cotton. Table 1
  • Soil release test of PEQ softening actives on oily soil from cotton is shown in Table 2.
  • PEQs have thus been shown to have a soil release benefit when compared with both no treatment and when compared with conventional ester quats.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

On décrit l'utilisation, en tant qu'agent facilitant l'élimination des salissures, de composés de la formule (I), dans laquelle X représente un anion, A représente un radical valent (m + n) restant après l'enlèvement de groupes hydroxy (m + n) à partir d'un polyol aliphatique, lequel présente des groupes hydroxy (p) et un rapport atomique carbone/oxygène de l'ordre de 1,0 à 3,0, et jusqu'à deux groupes par groupe hydroxy choisis entre l'oxyde d'éthylène et l'oxyde de propylène, m vaut 0 ou est un nombre entier de 1 à p-n, n est un nombre entier de 1 à p-m, et p est un nombre entier d'au moins 2, B représente un groupe alkylène ou alkylidène contenant 1 à 4 atomes de carbone, R?1, R2, R3 et R4¿ représentant indépendamment des groupes alcényle ou alkyle C¿1?-C48 à chaîne droite ou ramifiée, éventuellement substitués par un ou plusieurs groupes fonctionnels et/ou interrompus par au moins 10 groupes d'oxyde d'éthylène et/ou d'oxyde de propylène, ou par au maximum deux groupes fonctionnels choisis parmi (a), (b), (c), (d) et (e); ou bien R?2 et R3¿ peuvent former un système de noyaux contenant 5 ou 6 atomes dans les noyaux, à la condition que le composé moyen possède soit au moins un groupe R comprenant 22 à 48 atomes de carbone, soit au moins deux groupes R comprenant 16 à 20 atomes de carbone, soit au moins trois groupes R comprenant 10 à 14 atomes de carbone.
PCT/EP1996/003248 1995-08-25 1996-07-20 Agent facilitant l'elimination des salissures et son utilisation dans des compositions de conditionnement de tissus WO1997008286A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP96927048A EP0848748A1 (fr) 1995-08-25 1996-07-20 Agent facilitant l'elimination des salissures et son utilisation dans des compositions de conditionnement de tissus
AU67016/96A AU6701696A (en) 1995-08-25 1996-07-20 Soil release agent and its use in fabric conditioning compositions
BR9610021A BR9610021A (pt) 1995-08-25 1996-07-20 Uso de um composto e de seu produto de hidrólise e composição de condicionamento de tecido

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9517433.0 1995-08-25
GBGB9517433.0A GB9517433D0 (en) 1995-08-25 1995-08-25 Soil release agent and its use in fabric conditioning compositions

Publications (1)

Publication Number Publication Date
WO1997008286A1 true WO1997008286A1 (fr) 1997-03-06

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Application Number Title Priority Date Filing Date
PCT/EP1996/003248 WO1997008286A1 (fr) 1995-08-25 1996-07-20 Agent facilitant l'elimination des salissures et son utilisation dans des compositions de conditionnement de tissus

Country Status (6)

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EP (1) EP0848748A1 (fr)
AU (1) AU6701696A (fr)
BR (1) BR9610021A (fr)
GB (1) GB9517433D0 (fr)
WO (1) WO1997008286A1 (fr)
ZA (1) ZA966462B (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0398133A2 (fr) * 1989-05-19 1990-11-22 The Procter & Gamble Company Polyesters cationiques comme agents polymères antisalissures
EP0506312A1 (fr) * 1991-03-25 1992-09-30 Unilever Plc Utilisation d'adoucissant pour le linge
EP0638639A1 (fr) * 1993-08-10 1995-02-15 Akzo Nobel N.V. Composition adoucissante biodégradable pour le linge

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0398133A2 (fr) * 1989-05-19 1990-11-22 The Procter & Gamble Company Polyesters cationiques comme agents polymères antisalissures
EP0506312A1 (fr) * 1991-03-25 1992-09-30 Unilever Plc Utilisation d'adoucissant pour le linge
EP0507478A1 (fr) * 1991-03-25 1992-10-07 Unilever Plc Composition adoucissante pour le linge
EP0638639A1 (fr) * 1993-08-10 1995-02-15 Akzo Nobel N.V. Composition adoucissante biodégradable pour le linge

Also Published As

Publication number Publication date
BR9610021A (pt) 1999-07-06
AU6701696A (en) 1997-03-19
EP0848748A1 (fr) 1998-06-24
ZA966462B (en) 1998-01-30
GB9517433D0 (en) 1995-10-25

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