CN1005735B - Textile finishing agent - Google Patents

Textile finishing agent Download PDF

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Publication number
CN1005735B
CN1005735B CN86102993.3A CN86102993A CN1005735B CN 1005735 B CN1005735 B CN 1005735B CN 86102993 A CN86102993 A CN 86102993A CN 1005735 B CN1005735 B CN 1005735B
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Prior art keywords
alkyl
dispersion
senior
amine
acid
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CN86102993.3A
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CN86102993A (en
Inventor
阿克塞尔·康尼格
弗朗切斯科·德·布扎卡里尼
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Procter and Gamble Co
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Procter and Gamble Co
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Priority claimed from GB858508130A external-priority patent/GB8508130D0/en
Priority claimed from GB858520803A external-priority patent/GB8520803D0/en
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Publication of CN86102993A publication Critical patent/CN86102993A/en
Publication of CN1005735B publication Critical patent/CN1005735B/en
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/61Polyamines polyimines
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/645Mixtures of compounds all of which are cationic
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005Other compounding ingredients characterised by their effect
    • C11D3/001Softening compositions
    • C11D3/0015Softening compositions liquid
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M7/00Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Contains a Bronstedt acid having a PKa value of up toLess than 6 of aqueous dispersion containing amine, and the performance is stable. Is added in the process of washing the fabric and is used as a fabric softener. C 1, application number 86102993.3 int.4D06M 13/46 approval notice day 1989.11.08

Description

Textile finish
What the present invention relates to is textile finish.In the circulation flushing process, make fabric sofetening when this textile finish is particularly useful for textile washing, help Electrostatic Control.Its constructional feature is fabulous flexibility, water dispersible and storage property.It can be higher or lower than long storage under the condition of normal temperature.
In the fabric washing process, make fabric sofetening, and help controlling the electrostatic textile finish and will carefully state in this article.The concurrent widespread commercial purposes that having now.The softening agent that is added on the fabric when washing usually comprises an active group, comes down to have the water-fast cationic substance of two chain alkyls.Material commonly used is the dimethyl oronain that two animal tristearin are arranged, or with two animals tristearin group substituted imidazolines.The material of these preparations is aqueous dispersion usually.Generally speaking, prepare the viscosity that the watery dispersion that contains the 10% above cationic softener of having an appointment will have a strong impact on product, also can produce the problem of stability storage period.Though at European patent NO.0,000,406 and English Patent NO.1601360 in stated when the softening agent of preparation high density, can add in softening agents in conjunction with some non-ionic type additives, but from the soft effect of unit weight promoting agent, the efficient of this structure is lower.In addition, the viscosity of denseer water dispersion product and stability problem also become more outstanding, are difficult to control, and the commercial applications scope dictates active agent content of softening agent is 15%~20%.
People such as MacGilp disclosed on United States Patent (USP) 4454049 and concentrated aqueous fabric softener on June 12nd, 1984, and it is to contain 10% and organic solvent water immiscible phase at least, generally contains 30%~40% approximately.
On August 8th, 1961, people such as luvisi published the Barbiturates that adopts certain imidazolidine derivatives on United States Patent (USP) 2995520, and it is used for the softness of filamentary materials such as cotton, paper.Be used for the treatment trough of textile finishing, containing the hydrochlorate of a kind of imidazolidine derivatives of 0.001%~1% concentration, will be placed on product in the low molecular weight aliphatic alcohol, freezing to prevent it in order to transport allegedly.
Disclosed other patents of upgrading than United States Patent (USP) 2995520 are a kind of imidazolidine derivatives hydrochlorates, make fabric sofetening with it.Yet, the statement of pressing this paper, from the soft angle of fabric, the quaternary ammonium salt ratio resembles hydrochlorate better effects if such as no cyclic tertiary amine or cyclammonium.
Therefore, target of the present invention provides the fabric softener of liquid, and it can be formed in dilution or enrichment stage all need not add the water dispersion of organic solvent.Product of the present invention is being higher or lower than under the situation of normal temperature, even long storage, and fabulous stability is also arranged, and these syntheticss can further provide fabulous flexibility, and characteristics such as static resistance and fabric rewetting lubricant nature can be widely used among the various fabrics.
The invention provides a kind of stable water dispersion comprises:
(a) contain two (senior alkyl) cyclammonium in the indication molecular formula I, choose 1%~40% and contain the amine amount.Then with its mixing.
(b) from the softening agent of the quaternary amines of routine, select a kind of compound; It contains two senior alkyls, and each contains 8~30 carbon atoms.
Basis of the present invention is the preparation of stable water dispersion, and it has certain cyclammonium, in addition in the amine of high density also can with two (senior alkyl) quaternary ammonium salt preparation in the routine, and do not need a large amount of organic solutions.
(a) amine:
The amine that product of the present invention uses is to choose from the group class that contains the molecular formula I, as composition (I).
The molecular formula I
Figure 86102993_IMG4
N represents 2,3 or 4 in the formula, and is the most handy 2, R 1And R 2Being independently, is alkyl or the alkenyl that contains 8~30 carbon atoms, better selects the alkyl of 11~22 carbon atoms for use, preferably selects the alkyl that contains 15~18 carbon atoms for use, or with the mixture that has this type of alkyl atomic group.For example can from Oleum Cocois, " soft " (not being hard) Tallow, beef and hard Tallow, beef, obtain the alkyl atomic group of this compounds.
Q is CH, CH 2, NL or N.The most handy N.
X is
T is 0 or NR in the following formula 5, R 5Be H or the alkyl that contains 1~4 carbon atom, preferable with H.R 4Be a divalent alkyl group or (a C who contains 1~3 carbon atom 2H 4O) m, m gets 1~8 here.The also desirable R of X 4
It is 1%~40% that synthetics of the present invention contains the amine amount, better selects 2%~35% for use, and the best is to select 2%~20% for use.
In washing process, may produce the washing composition residuum.Particularly under the situation of using U.S.'s popular washing machine, the tendency that adds the softening agent effect in a kind of negative water is arranged.Amine is difficult for working to the washing composition residuum in the molecular formula I as can be seen.For example resemble two Tallow, beef dimethyl chloride ammonium compounds.
(b) quaternary ammonium salt:
Two (senior alkyl) quaternary ammonium salt softening agent that contains a routine in the described dispersion is as second kind of composition.Here the senior alkyl in the quaternary ammonium salt of context indication is the groups that has 8~30 carbon atoms.Preferably select 11~20 carbon atoms for use.For example Chang Gui quaternary ammonium salt comprises (I) acyclic quaternary ammonium salt, and its molecular formula is:
Figure 86102993_IMG6
Here R 2It is the acyclic aliphatic alkyl that contains 15~22 carbon atoms.R 3It is a saturated alkyl or a hydroxyalkyl that contains 1~4 carbon atom.R 4From R 2Or R 3In choose.A is a negatively charged ion.
(II) diamide based quaternary ammonium salt molecular formula is:
Figure 86102993_IMG7
Here R 1Be acyclic aliphatic alkyl, contain 15~21 carbon atoms.R 2Be the alkylidene group of a divalence, contain 1~3 carbon atom.R 5And R 8Be saturated alkyl or the hydroxyalkyl that contains 1~4 carbon atom.A -It is a negatively charged ion.
(III) diamide alkoxy quaternary ammonium salinity minor:
(the n value is got 1-about 5 here.R 1, R 2, R 5, A -The same with above-mentioned definition.)
(VI) quaternary ammonium salt imidazolinium compounds:
Composition in the example (I) is that everybody knows.
Dialkyl dimethyl ammonium salt is as two Tallow, beef dimethyl oronains, two Tallow, beef Dimethyl Ammonium methylsulfuric acid esters, two (hydrogenated tallow) dimethyl oronain, distearyl dimethyl oronain, dibehendyl dimethyl oronain.
Composition in the example (II) is methyl two (buserelin Tallow, beef) (2-hydroxyethyl) ammonium methylsulfuric acid ester, methyl two (ethyl hydride acid amides Tallow, beef) (2-hydroxyethyl) amine methylsulfuric acid ester.Here R 1It is the acyclic aliphatic alkyl that contains 15~17 carbon atoms.R 2It is a vinyl.R 5It is a methyl.R 8It is a hydroxyalkyl.A is the methylsulfuric acid negatively charged ion.These compounds all can have been bought from Sherex chemical company, and its trade name is respectively Uarisoft(R) 222 and Uarisoft(R) 110.
(IV) is in the example:
1-methyl isophthalic acid-tallow amides base-ethyl-2-Tallow, beef tetrahydroglyoxaline ethyl methylsulphonate and 1-methyl isophthalic acid-(hydrogenated tallow acid amides ethyl)-methylsulfuric acid ester.
Quaternary ammonium salt (b) content should be got 1%~20% of product gross weight, preferably gets 2%~20%.
Part by weight, amine (a): its scope of quaternary ammonium salt (b) should adopt 3: 1 to 1: 3 from 10: 1 to 1: 10.
This paper preferentially selects two (senior alkyl) imidazolinium compounds for use, especially 1-(low alkyl group)-and the 1-(senior alkyl) acid amides ethyl-2-(senior alkyl) imidazole-based compounds, " low alkyl group " of indication is meant the alkyl that contains 1~4 carbon atom, and " senior base " is the alkyl that contains 11~22 carbon atoms.
(c) choose cloth Leinster (Bronstedt) acid.
It is 6 or less that dispersion is selected cloth Leinster acid PKa value for use.
It is to guarantee that the pH value that mixes the back dispersion agent is not more than 5 that acid content requires, and should adopt and be not more than 4, and only pH value scope is 2.5~4.1%~50% of the weight that typical sour content is amine should adopt 2%~30%, and the best is 3%~15%.
The kind of suitable acid comprises inorganic mineral acid, carboxylic acid.The particularly low-molecular-weight carboxylic acid that contains 1~5 carbon atom, the carboxylic acid of aromatics is as phenylformic acid and alkylsulphonic acid.
The mineral acid that is suitable for comprises hydrochloric acid, Hydrogen bromide, and sulfuric acid, nitric acid, phosphoric acid, appropriate organic comprises phenylformic acid, formic acid, acetic acid, methylsulphonic acid and ethylsulfonic acid.Preferentially select phosphoric acid for use, formic acid and methylsulphonic acid.
(d) organic solvent
The preparation of product of the present invention need not any organic solvent.Yet organic solvent (as low-molecular-weight Fatty Alcohol(C12-C14 and C12-C18) that can be molten with water) can not influence the stability of storage, the flexibility of viscosity or this product.
Usually the amine major part derives from solid-state chemical substance, and it is dissolved in becomes solution in the organic solvent.Virahol organic solvent for example.When this product of preparation, needn't remove organic solvent in any case.In fact adding a little ideal annex solutions allows fully.
In addition, more expensive with water than organic solution price, and combustibility is arranged, even toxicity, be difficult to management.Ideal preparation of the present invention is to use a small amount of organic solution, promptly is lower than 10%, is preferably lower than 2%.
(e) select the organo-siloxane composition
This product is selected watery emulsion for use, mainly is the polydialkysiloxane or the alkylaryl siloxanes of straight chain type, and alkyl can contain 1~5 carbon atom here, can all or part ofly fluoridize.The organo-siloxane that is suitable for is a polydimethylsiloxane, in the time of 25 ℃ its range of viscosities from 100~100,000 centistoke, best use range is 300~6000 centistokes.
Found that used organo-siloxane ion live-wire characteristic is very important, it plays a decisive role to the homogeneity of organosilyl precipitation degree and distribution, influences the performance after the textile finishing.
Have cationic organo-siloxane and can accelerate precipitation.Found that organo-siloxane helps improving fabric feeling, it has a main straight chain, and preferably uses polydialkysiloxane, and alkyl is selected methyl usually for use.The emulsus polymkeric substance of organosiloxane polymer general merchandise manufacturing is in the nonionic surface active agent emulsifying agent or non-ionic type-anionic blended surfactant emulsifiers system in, with strong acid or highly basic as catalyzer.
The organo-siloxane that the present invention selects for use is decided by its cationic characteristic.Its implication is as follows.
(a) a main straight chain is two and contains the alkyl of 1~5 carbon atom or the alkylaryl siloxanes of 1~5 carbon atom, and the most handy cats product is as the emulsion polymer emulsifying agent.
(b) α-ω-2 through quaternization and two contain the alkyl of 1~5 carbon atom or 1~5 carbon atom alkyl aryl siloxanes polymkeric substance or
(c) two of an ammonia functional group alkyl or effects of alkylaryl siloxane polymer that contain 1~5 carbon atom.Amino can be used as substituting group or quaternization takes place, and its substitution value (d.s) remains in 0.001~0.1 scope, and preferably 0.1~0.075.
The viscosity of organo-siloxane is 100~100 in the time of 25 ℃, 000 centistoke.
This product siloxanes and amine content ratio can adopt 5: 1 to 1: 100, preferably adopted 2: 1 to 1: 10 scopes.
Abundant disclosed organo-siloxane composition is applicable to this product among the English Patent NO.1549180.
(f) select nonionic surface active agent for use
It is open to select for use nonionic surface active agent to make softening agent.On June 12nd, 1984, people such as Mac Gilp disclosed nonionic surface active agent and their consumption on United States Patent (USP) 4454049.Here with reference to its disclosed part.
The special nonionic surface active agent that is applicable to this product comprises glyceride (for example glycerine Monostearate), Fatty Alcohol(C12-C14 and C12-C18) (as Stearyl alcohol) and alkoxyl group Fatty Alcohol(C12-C14 and C12-C18).Content commonly used when nonionic surface active agent uses is 0.5%~10% of product gross weight.
(g) other selects composition for use
In order further to improve stability, further adjust their viscosity, this product can contain small amount of electrolyte.Best ionogen is calcium chloride (CaCl 2).Found that the few calcium chloride of consumption (routine 600PPm) can make the extremely viscous degree of Brooker Fei Er (Brookfield) of the dispersion of high density reduce to below 100 centistokes.
This product can be selected the soft auxiliary of some other textiless for use, comprises resembling perfume, and sanitas, sterilant, tinting material, dyestuff, fungicide, stablizer, brightening agent and opalizer, these auxiliarys are measured adding routinely.
In addition, for increasing a certain effect of arrangement back fabric, for example, the consumption of perfume products auxiliary (for product concentration) can be suitably big.
Example I-IV
The preparation of several products:
Example 1 example 2 examples 3 examples 4
DTI 1)20% 10% 8% -
DTDMAC 2)- 10% 12% 15%
PDMS 3)- - 1% -
Acid 0.2% 4)--0.4% 5)
Calcium chloride (PPm) 600 800 900 1200
GMS 6)- 1% - -
Stearyl alcohol--1%-
Amine 7)10% 8% 5% 10%
Perfume 0.9% 0.9% 0.9% 0.7%
Water Yu amount Yu amount Yu amount Yu amount
1) two Tallow, beef tetrahydroglyoxalines
(1-methyl isophthalic acid-Tallow, beef-amide group-ethyl-2-tetrahydroglyoxaline chlorine)
2) two Tallow, beef dimethyl chloride ammonium salts
3) polydimethylsiloxane, viscosity are 500 centistokes
4) formic acid
5) methylsulphonic acid
6) single stearate glycerine
7) 1-tallow amides ethyl-2-Tallow, beef imidazoles
Hydrolysis can take place in two Tallow, beef tetrahydroglyoxaline composition work in-processes, but little to the soft effect influence of product.
Example V-VIII
Below in several formulation examples, each routine pH value scope 2.5~5.
Composition * example V example VI example VII example VIII
DTDMAC 12.33 7.0 1.26 3.78
PDMS 21.33 5.0 0.333 1.0
Amine 34.33 13 2.34 7.02
Hydrochloric acid 0.268 0.805 0.145 0.435
Calcium chloride 0.005 0.17-0.1
Emulsifying agent 40.133 0.5 0.033 0.1
Perfume/dyestuff 0.252 0.753 0.251 0.752
Water is fitted on
100% 100% 100% 100%
*Ingredients listed content refers to account for the per-cent of product gross weight.
1.DTDMAC implication is identical with routine II, III and IV
2.PDMS be meant polydimethylsiloxane, viscosity is 5000 centistokes.
3. amine-1-(2-C 14-C 18-acid amides ethyl)-2-C 13-C 17-alkyl-4,5 glyoxalidine quinoline, CAS number is 72623-82-6.
4. emulsifying agent " Sapogenat T-100 " (article number) is triisobutyl phenol decagly eolether Hoechst.

Claims (18)

1, a kind of stable water dispersion, this water dispersion comprises
(a) amine mixt of two (senior alkyl) cyclammonium that is selected from following general formula of 1%~40%;
(n is 2,3 or 4 in the formula, R 1And R 2Be respectively C 8-C 30The mixture of alkyl or alkenyl or these groups; Q is CH, CH 2, NH or N, X is
Figure 86102993_IMG2
,
T is NR in the formula 5, R 5Be H or C 1-4Alkyl, R 4C for divalence 1-C 3Alkenyl or (C 2H 4O) m, m are the integer of 1-8, X or be R 4;
(b) 1% to 20% compound that is selected from conventional quaternary ammonium softener, this quaternary ammonium softener has two senior alkyls that respectively contain 8-30 carbon atom;
(c) about 1% of amine weight to about 50% dispersing auxiliary, this dispersing auxiliary are cloth Leinster (Bronstedt) acid, and its pKa value is not more than 6, and it is 5 or littler that this acid consumption makes the pH of composition;
(d) 0% to the organic solvent that is lower than 10%;
(e) rest part of composition is a water.
2, dispersion according to claim 1, wherein (a): weight ratio (b) is 3: 1 to 1: 3 a scope.
3, dispersion according to claim 2, this dispersion contains 2% to 35% amine.
4, dispersion according to claim 3, Q wherein is N, and n is 2, and X is
Figure 86102993_IMG3
5, dispersion according to claim 4, amine wherein are the 1-(senior alkyl) acid amides ethyl-2-(senior alkyl) tetrahydroglyoxaline, this senior alkyl is represented the alkyl of 11 to 22 carbon atoms.
6, dispersion according to claim 5, wherein (b) is selected from the 1-(low alkyl group)-the 1-(senior alkyl) acid amides ethyl-2-(senior alkyl) imidazolinium compounds, this low alkyl group is represented the alkyl of 1 to 4 carbon atom, and this senior alkyl is represented the alkyl of 11 to 22 carbon atoms.
7, according to the described dispersion of above-mentioned each claim, this dispersion also contains with straight chain type two (C 1-C 5) alkyl or C 1-C 5The alkaryl siloxanes is the emulsion of main component, alkyl wherein can partly or entirely be fluoridized, also can replace by the cationic nitrogenous group, the viscosity of siloxanes (25 ℃) is at least 100 centistokes, reach as high as 100,000 centistoke, the weight ratio of content of siloxane and amine is 5: 1 to 1: 100 in the emulsion.
8, dispersion according to claim 7, siloxanes wherein is a polydimethylsiloxane.
9, dispersion according to claim 7, this dispersion also contain 0.5% to 10% the non-release sub-compound that is selected from glyceryl ester, Fatty Alcohol(C12-C14 and C12-C18) or oxyalkylated Fatty Alcohol(C12-C14 and C12-C18).
10, dispersion according to claim 7, wherein the pH of dispersion is 2.5 to 4.
CN86102993.3A 1985-03-28 1986-03-28 Textile finishing agent Expired CN1005735B (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB8508130 1985-03-28
GB858508130A GB8508130D0 (en) 1985-03-28 1985-03-28 Textile treatment composition
GB8520803 1985-08-20
GB858520803A GB8520803D0 (en) 1985-08-20 1985-08-20 Textile treatment compositions

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CN86102993A CN86102993A (en) 1986-10-01
CN1005735B true CN1005735B (en) 1989-11-08

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8508129D0 (en) * 1985-03-28 1985-05-01 Procter & Gamble Ltd Textile treatment composition
US4668234A (en) * 1985-08-15 1987-05-26 E. I. Du Pont De Nemours And Company Aromatic polyamide fibers and process for stabilizing such fibers with surfactants
US4661267A (en) * 1985-10-18 1987-04-28 The Procter & Gamble Company Fabric softener composition
GB2188653A (en) * 1986-04-02 1987-10-07 Procter & Gamble Biodegradable fabric softeners
DE3720331A1 (en) * 1987-06-19 1988-12-29 Huels Chemische Werke Ag CONCENTRATED SOFT SOFTENER
EP0316996A3 (en) * 1987-11-18 1990-04-04 The Procter & Gamble Company Method for preparing textile treatment compositions
EP0345842A3 (en) * 1988-05-27 1990-04-11 The Procter & Gamble Company Fabric softening compositions containing mixtures of substituted imidazoline esters and quartenized ester-ammonium salts
US5254269A (en) * 1991-11-26 1993-10-19 Lever Brothers Company, Division Of Conopco, Inc. Fabric conditioning composition containing an emulsified silicone mixture
US5723426A (en) 1996-02-29 1998-03-03 Zhen; Yueqian Liquid laundry detergent compositions containing surfactants and silicone emulsions

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2995520A (en) * 1956-06-11 1961-08-08 Nalco Chemical Co Treatment of fibrous materials and compositions therefor
NL7609621A (en) * 1975-09-04 1977-03-08 Hoechst Ag TEXTILE TREATMENT AGENT.
DE2722079C3 (en) * 1977-05-16 1979-12-06 Basf Ag, 6700 Ludwigshafen Liquid softener for textiles
DE3263800D1 (en) * 1981-01-16 1985-07-04 Procter & Gamble Textile treatment compositions
GB8508129D0 (en) * 1985-03-28 1985-05-01 Procter & Gamble Ltd Textile treatment composition

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EG17723A (en) 1990-10-30
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GB2174422B (en) 1989-01-11
CA1279447C (en) 1991-01-29
CN86102993A (en) 1986-10-01
MA20655A1 (en) 1986-10-01
IE59115B1 (en) 1994-01-12
MX165248B (en) 1992-11-04
DK139886A (en) 1986-09-29
MY100080A (en) 1989-08-18
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FI861341A0 (en) 1986-03-27
EP0197578A3 (en) 1987-12-02
EP0197578A2 (en) 1986-10-15
GB2174422A (en) 1986-11-05
DE3679927D1 (en) 1991-08-01
KR860007415A (en) 1986-10-13
GB8607691D0 (en) 1986-04-30
KR930008698B1 (en) 1993-09-13
FI861341A (en) 1986-09-29
EP0197578B1 (en) 1991-06-26
DK139886D0 (en) 1986-03-25
TR23492A (en) 1990-02-01
AU5535386A (en) 1986-10-02

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