EP0335404A2 - Flüssige Weichspülerzusammensetzung - Google Patents

Flüssige Weichspülerzusammensetzung Download PDF

Info

Publication number
EP0335404A2
EP0335404A2 EP89105663A EP89105663A EP0335404A2 EP 0335404 A2 EP0335404 A2 EP 0335404A2 EP 89105663 A EP89105663 A EP 89105663A EP 89105663 A EP89105663 A EP 89105663A EP 0335404 A2 EP0335404 A2 EP 0335404A2
Authority
EP
European Patent Office
Prior art keywords
component
softener composition
liquid softener
carbon atoms
group
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP89105663A
Other languages
English (en)
French (fr)
Other versions
EP0335404A3 (de
Inventor
Hisami Sasaki
Syouzi Takeda
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lion Corp
Original Assignee
Lion Corp
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 Lion Corp filed Critical Lion Corp
Publication of EP0335404A2 publication Critical patent/EP0335404A2/de
Publication of EP0335404A3 publication Critical patent/EP0335404A3/de
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C11D3/16Organic compounds
    • C11D3/37Polymers
    • C11D3/3746Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3757(Co)polymerised carboxylic acids, -anhydrides, -esters in solid and liquid compositions
    • C11D3/3765(Co)polymerised carboxylic acids, -anhydrides, -esters in solid and liquid compositions in liquid compositions
    • 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
    • C11D1/66Non-ionic compounds
    • C11D1/835Mixtures of non-ionic with cationic compounds
    • 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
    • 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
    • C11D1/62Quaternary ammonium compounds
    • 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
    • C11D1/66Non-ionic compounds
    • C11D1/72Ethers of polyoxyalkylene glycols

Definitions

  • the present invention relates to a softener composition which can impart, for example, an excellent softness and antistatic property to fiber, clothing, and hair. More specifically, it relates to an aqueous liquid softener composition which can impart an excellent softness and antistatic property to chemical textile products such as of acryl, nylon, polyester, and also has an excellent dispersion stability.
  • a softener containing a quaternary ammonium salt having two long chain alkyl groups or alkenyl groups in the molecule as the main component has been employed.
  • Representative examples of the quaternary ammonium salts include di-hardened tallow alkyldimethylammonium chloride, and methyl-1-tallow amidoethyl-2-alkylimidazolinium methylsulfate, but these single products, although they are capable of imparting excellent softness to cotton products, have no sufficient effect from the view point of imparting softness and an antistatic property to chemical fiber products.
  • an object of the present invention is to obviate the above-mentioned problems in the prior art and to provide an aqueous liquid softener composition which can impart the same softness to cotton as that of the prior art products, but a much greater softness and antistatic property to chemical fibers, compared with the prior art products in softening treatment practiced in the washing and rinsing steps at home, and further, has an excellent dispersion stability.
  • liquid softener composition comprising:
  • the slightly water-soluble quaternary ammonium salt of the component (A) usable in the present invention may be exemplified by those represented by the formula (I) or (II) shown below. These compounds can be used alone or as a mixture of two or more compounds, and these are cationic surfactants having 2 or 3 straight or branched alkyl or alkenyl groups with 14 to 24 carbon atoms in the molecule which may be respectively optionally substituted or intermingled with functional groups such as -OH, -O-, - -NH-, - -O-.
  • R1 - R4 represent straight or branched alkyl or alkenyl groups which may be unsubstituted or optionally substituted by -OH-, -O-, - -NH-, - -O-, etc., the remainder of the groups of R1 - R4 represent an alkyl group with 1 to 3 carbon atoms, a hydroxyalkyl group or a group represented by the formula -(C2H4) l H (where l is an integer of 1 to 5, and X represents a halogen or a monoalkylsulfate group represented by R5SO4 where R5 represents an alkyl group with 1 to 3 carbon atoms).
  • R6 represents an alkyl group with 1 to 4, preferably 1 to 2 carbon atoms
  • R7 and R8 each represent an alkyl or alkenyl group with 14 to 24 carbon atoms
  • R9 represents hydrogen or an alkyl group with 1 to 4 carbon atoms
  • X has the same meaning as in the formula (I).
  • At least two groups of R1 - R4 in the above formula (I) have 14 to 24, preferably 16 to 22 carbon atoms, R7 and R8 in the above formula (II) have 14 to 24, preferably 15 to 21 carbon atoms, each group may have a distribution within these ranges, and the respective groups may be either the same or different from each other.
  • the carbon number is lower than this range, for example, when a mixture of quaternary ammonium salts of (I) or (II) synthesized from coconut fatty acids is used, the softness will be poor.
  • component (A) include one or a mixture of two or more of di-hardened tallow alkyldimethylammonium chloride, di-tallow alkyldimethyl­ammonium bromide, dioleyldimethylammonium chloride, dipalmitylhydroxyethylammonium methylsulfate, distearyl­methylpolyoxyethylene (average degree of polymerization is 3)ammonium chloride, diisostearyldimethylammonium methylsulfate, dieicosyldimethylammonium chloride, dibehenylmethylpolyoxyethylene (average degree of polymerization is 5)ammonium chloride, dierucyldimethylammonium chloride, di[2-dodecanoylamino)ethyl]-dimethylammonium chloride, di[2-stearoylamino)propyl]dimethylammonium ethylsulfate, di(2-ethylpalmitoy
  • carboxylic acid type anionic polymer of the component (B) homopolymers of ethylenically unsaturated carboxylic acids or anhydrides thereof or copolymers of said monomers can be used.
  • the salts of these homopolymers and copolymers may be used.
  • these polymers may be used either as such or in the form of water soluble neutral salts such as alkali metal salts or alkaline earth metal salts.
  • the component (B) has an average molecular weight generally of 500 to 50,000, preferably 500 to 20,000, and more preferably 500 to 10,000.
  • the above-mentioned anionic polymrs to be used as the component (B) should be the so-called "oligomers" which have a relatively low molecular weight.
  • the molecular weight thereof is higher, the desired sufficient dispersion stability obtained from the addition of the component (C) as mentioned hereinbelow is prevented. Contrarily, when the molecular weight is lower, the effect obtained from addition of the component (B) as mentioned hereinbelow becomes insufficient.
  • component (B) may include one or a mixture of two or more of polyacrylic acid, polymethacrylic acid, polycrotonic acid, polyacotinic acid, poly- ⁇ -hydroxyacrylic acid, polymaleic acid, polysorbic acid, polyitaconic acid, poly(maleic anhydride), poly(itaconic anhydride) their copolymers, or salts of these homopolymers or copolymers.
  • the reason why excellent effect can be obtained by using the component (A) and the component (B) in combination is not clear, but it may be considered to be as follows. That is, although the ion bonding between the both may not be so strong, by forming a cation-anion complex with a part of the dispersed particles of the component (A), the component (A) can be made further hydrophobic to promote adsorption of the component (A) onto chemical fibers such as acrylic or polyester fibers which are hydro­phobic fibers, whereby softness and antistatic property of the chemical fibers can be consequently further improved as compared with the case of the component (A) alone.
  • chemical fibers such as acrylic or polyester fibers which are hydro­phobic fibers
  • the component (B) which is a water soluble polymer will not be incorporated into the dispersed particles of the component (A) and will not destroy the adsorption structure of the component (A), as different from a some kinds of anionic surfactant, and consequently will not give any adverse effect on the softness of cotton fibers.
  • these compounds are formulated, in terms of the ratio of positive charge mols (a) of the component (A) to the negative charge mols (b) of the component (B), at a ratio (a)/(b) of 1/0.2 to 1/2.0, preferably 1/0.5 to 1/1.0. If the ratio of the component (B) to the component (A) is outside this range, the above effect of combined use is difficult to obtain.
  • the third essential component for accomplishing the object of the present invention is the component (C). That is, a sufficient dispersion stability is an essential condition for use as a softener for domestic use, but only with the components (A), (B), (D), the required dispersibility cannot be obtained, and accordingly the emulsifying stabilizing action of the component (C) is necessary.
  • the component (C) usable in the present invention may be exemplified by polyoxyethylene alkylphenyl ether, polyoxyethylene alkyl (or alkenyl) ether, polyoxyethylene fatty acid amide, polyoxyethylene alkyl (or alkenyl) amine, and polyoxyethylene sorbitane fatty acid ester.
  • Preferable average additional moles of ethylene oxide are at least 20, more preferably 20 to 100.
  • each POE represents polyoxyethylene
  • p denotes the average adducted mols of ethylene oxide
  • C the carbon number of the alkyl or alkenyl group (hereinafter the same).
  • the component (C) improves the emulsifying dispersion of the dispersed particles of the component (A) alone and the anion-cation complex of the dispersed particles of the component (A) with the component (B), which may be considered to form a random coil structure dissolved in the aqueous phase in the composition, and thus the amount of the component (C) formulated is preferably 100/1 to 3/1 as a weight ratio of (A)/(C), more preferably 50/1 to 5/10. If the ratio of the component (C) to the component (A) is outside of this range, the above effect cannot be exhibited, and conversely, the above effect of combined use of the component (A) and the component (B) is frequently inhibited.
  • the component (D) is used as the carrier for the essential components and the optional components of the present invention, and the amount thereof in the composition is the balance which makes up the total amount to 100%, in addition to the essential components and the optional components formulated.
  • the softener composition of the present invention can include optional components in addition to the above essential components, including viscosity controllers such as inorganic electrolytes like sodium chloride, potassium chloride, magnesium chloride, aluminum chloride, sodium sulfate, ammonium sulfate, sodium nitrate, or magnesium nitrate; and polyethylene glycol or other water soluble organic polymers; hydrotropes such as lower alcohols like ethanol, or isopropanol, ethylene glycol, glycerine, and urea; and pH controllers, sterilizers, pigment dyes, perfumes, antioxidants, UV-ray absorbers, and fluorescent brighteners.
  • viscosity controllers such as inorganic electrolytes like sodium chloride, potassium chloride, magnesium chloride, aluminum chloride, sodium sulfate, ammonium sulfate, sodium nitrate, or magnesium nitrate
  • polyethylene glycol or other water soluble organic polymers such as lower alcohols like ethanol, or isopropanol
  • the softener composition of the present invention can be prepared according to known methods. More specifically, it is desirable that the component (A) should be finely and uniformly dispersed, and for this purpose, it is preferable to use the method in which the components (B), (C) and optical components are previously dissolved in an aqueous vehicle, and to this solution is successively added, under heating to 40°C to 80°C if desired, the component (A) in a molten state to be mixed under stirring. On the other hand, when optional components susceptible to denaturation at high temperature are used, it is desirable to cool the above dispersion to about room temperature, followed by addition while stirring.
  • a pH controller can be added to the softener composition of the present invention, but the pH of the composition is not limited. Usually, the pH is that when the respective components are formulated, but it is desirable to control pH to 4 to 8. For this purpose, an organic or inorganic acid or a basic compound can be formulated, as desired.
  • the softener composition of the present invention which can impart an excellent softness to not only cotton fibers but also chemical fibers, and further gives an excellent antistatic property to chemical fibers is valuable.
  • the present composition is excellent in practical application.
  • the above component (A) is available as a mixture with isopropanol, and therefore, the compositions were contaminated with about 1.7 (%) thereof.
  • the softener compositions of the present invention have excellent performance and dispersion stability. More specifically, although considerable softness is exhibited in the case of di-hardened tallow alkyldimethylammonium chloride alone, the softness and antistatic property of the acrylic cloth are clearly improved by addition of the component (B). Particularly, No. 1 and No. 5 can be appreciated to exhibit a very excellent antistatic property.
  • a rise in viscosity under the above storage conditions may be permissible up to about 1500 centipoise in commercial product value, and it can be seen that the products of the present invention satisfy this condition without causing phase separation due to the addition effect of the component (C) and the presence of ethylene glycol in the component (D).
  • the above component (A), is provided as a mixture with isopropanol, and therefore, the compositions were contaminated with about 3 (%) thereof.
  • the carboxylic acid type anionic polymers used in the present invention have performance improvement effects on all of the slightly water soluble quaternary ammonium salts having different structures from each other. More specifically, in Table 4, it can be seen that by an addition of sodium polyacrylate in equivalent amount to the component (A), in all cases, the performances, particularly softness and antistatic property of the acrylic cloths are greatly improved. Also, all of the above compositions of the present invention have good dispersion stability.

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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)
  • Cosmetics (AREA)
EP19890105663 1988-03-31 1989-03-30 Flüssige Weichspülerzusammensetzung Withdrawn EP0335404A3 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP79228/88 1988-03-31
JP7922888A JPH01250473A (ja) 1988-03-31 1988-03-31 液体柔軟剤組成物

Publications (2)

Publication Number Publication Date
EP0335404A2 true EP0335404A2 (de) 1989-10-04
EP0335404A3 EP0335404A3 (de) 1990-12-27

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP19890105663 Withdrawn EP0335404A3 (de) 1988-03-31 1989-03-30 Flüssige Weichspülerzusammensetzung

Country Status (2)

Country Link
EP (1) EP0335404A3 (de)
JP (1) JPH01250473A (de)

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0425853A3 (en) * 1989-10-30 1991-12-11 Lang & Co., Chemisch-Technische Produkte Kommanditgesellschaft Aqueous cleaning agent for compressors, particularly gas turbines
WO1992015664A1 (en) * 1991-03-04 1992-09-17 Ciba-Geigy Ag Aqueous textile auxiliary composition
WO1992019714A1 (en) * 1991-04-30 1992-11-12 The Procter & Gamble Company Fabric softener containing substituted imidazoline and highly ethoxylated compounds
US5242607A (en) * 1990-10-05 1993-09-07 Kao Corporation Concentrated softener
US5356443A (en) * 1992-09-08 1994-10-18 Ciba-Geigy Corporation Stabilization of dyeings of polyamide fibres
EP0590604A3 (en) * 1992-09-29 1996-03-27 Amerchol Corp Hairsprays and acrylic polymer compositions for use therein
WO1998040452A1 (en) * 1997-03-11 1998-09-17 Unilever Plc Hard-surface cleaning compositions
GB2323391A (en) * 1997-03-20 1998-09-23 Akzo Nobel Nv Dryer-activated fabric conditioning and antistatic compositions
US6017860A (en) * 1996-04-15 2000-01-25 Stepan Company Cleaning, conditioning and styling hair care compositions
WO2001025387A1 (en) * 1999-10-01 2001-04-12 Unilever Plc Fabric care composition
US6254859B1 (en) 1995-09-18 2001-07-03 Stepan Company Hair and skin conditioning compositions
WO2004024856A3 (en) * 2002-09-13 2004-06-10 Nippon Catalytic Chem Ind Liquid detergent builder and liquid detergent containing the same
WO2006124338A1 (en) * 2005-05-12 2006-11-23 The Procter & Gamble Company Fabric softening compositions stable under freeze-thaw conditions
US8728530B1 (en) 2012-10-30 2014-05-20 The Clorox Company Anionic micelles with cationic polymeric counterions compositions thereof
US8728454B1 (en) 2012-10-30 2014-05-20 The Clorox Company Cationic micelles with anionic polymeric counterions compositions thereof
US8765114B2 (en) 2012-10-30 2014-07-01 The Clorox Company Anionic micelles with cationic polymeric counterions methods thereof
KR101424551B1 (ko) * 2006-01-18 2014-08-01 인비스타 테크놀러지스 에스.에이 알.엘. 비-섬유 중합체 조성물 및 방법
US8883706B2 (en) 2012-10-30 2014-11-11 The Clorox Company Anionic micelles with cationic polymeric counterions systems thereof
US8883705B2 (en) 2012-10-30 2014-11-11 The Clorox Company Cationic micelles with anionic polymeric counterions systems thereof
CN104762812A (zh) * 2015-03-11 2015-07-08 刘晓 一种衣物柔顺剂
WO2018044639A1 (en) * 2016-08-31 2018-03-08 The Procter & Gamble Company Fabric enhancer composition
WO2022042277A1 (en) * 2020-08-28 2022-03-03 Ecolab Usa Inc. Method and extraction agent for methanol to olefins wash water system antifouling

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9011785D0 (en) * 1990-05-25 1990-07-18 Unilever Plc Fabric treatment compositions
KR100389684B1 (ko) * 2000-05-10 2003-07-04 김진원 대전방지제가 흡착된 신규한 비스코스레이온섬유 부직포 및 그 제조방법
JP4956821B2 (ja) * 2007-12-27 2012-06-20 ライオン株式会社 液体柔軟剤組成物
WO2013185346A1 (en) * 2012-06-15 2013-12-19 Rhodia Operations Method to recover or increase water absorbency of polyester textile
JP6053507B2 (ja) * 2012-12-26 2016-12-27 花王株式会社 柔軟剤組成物
CN105803775A (zh) * 2014-12-30 2016-07-27 上海氟聚化学产品有限公司 一种涤纶缝纫线用柔软剂
JP6913862B2 (ja) * 2017-01-30 2021-08-04 白元アース株式会社 帯電防止性組成物およびスプレー式帯電防止剤

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3537993A (en) * 1966-06-21 1970-11-03 Procter & Gamble Detergent compositions
CH574005B5 (de) * 1973-12-15 1976-03-31 Ciba Geigy Ag
DE2846047A1 (de) * 1977-10-26 1979-05-03 Unilever Nv Schmutzabweisende mittel, verfahren zu ihrer herstellung und ihre verwendung
FR2556364B1 (fr) * 1983-12-10 1989-10-27 Sandoz Sa Compositions detergentes liquides exemptes de phosphate

Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0425853A3 (en) * 1989-10-30 1991-12-11 Lang & Co., Chemisch-Technische Produkte Kommanditgesellschaft Aqueous cleaning agent for compressors, particularly gas turbines
US5242607A (en) * 1990-10-05 1993-09-07 Kao Corporation Concentrated softener
WO1992015664A1 (en) * 1991-03-04 1992-09-17 Ciba-Geigy Ag Aqueous textile auxiliary composition
WO1992019714A1 (en) * 1991-04-30 1992-11-12 The Procter & Gamble Company Fabric softener containing substituted imidazoline and highly ethoxylated compounds
US5356443A (en) * 1992-09-08 1994-10-18 Ciba-Geigy Corporation Stabilization of dyeings of polyamide fibres
EP0590604A3 (en) * 1992-09-29 1996-03-27 Amerchol Corp Hairsprays and acrylic polymer compositions for use therein
US5589157A (en) * 1992-09-29 1996-12-31 Amerchol Corporation Hairsprays and acrylic polymer compositions for use therein
US6254859B1 (en) 1995-09-18 2001-07-03 Stepan Company Hair and skin conditioning compositions
US6218346B1 (en) 1996-04-15 2001-04-17 Stepan Company Methods for cleaning, conditioning and styling hair
EP0904052B1 (de) * 1996-04-15 2002-12-11 Stepan Company Präparate zum reinigen, konditionieren und frisieren der haare
US6017860A (en) * 1996-04-15 2000-01-25 Stepan Company Cleaning, conditioning and styling hair care compositions
WO1998040452A1 (en) * 1997-03-11 1998-09-17 Unilever Plc Hard-surface cleaning compositions
AU734919B2 (en) * 1997-03-11 2001-06-28 Unilever Plc Hard-surface cleaning compositions
GB2323391A (en) * 1997-03-20 1998-09-23 Akzo Nobel Nv Dryer-activated fabric conditioning and antistatic compositions
WO2001025387A1 (en) * 1999-10-01 2001-04-12 Unilever Plc Fabric care composition
US6793684B1 (en) 1999-10-01 2004-09-21 Unilever Home & Personal Care Usa, Division Of Conopco, Inc. Fabric care composition
WO2004024856A3 (en) * 2002-09-13 2004-06-10 Nippon Catalytic Chem Ind Liquid detergent builder and liquid detergent containing the same
US7390776B2 (en) 2002-09-13 2008-06-24 Nippon Shokubai Co., Ltd. Liquid detergent builder and liquid detergent containing the same
WO2006124338A1 (en) * 2005-05-12 2006-11-23 The Procter & Gamble Company Fabric softening compositions stable under freeze-thaw conditions
KR101424551B1 (ko) * 2006-01-18 2014-08-01 인비스타 테크놀러지스 에스.에이 알.엘. 비-섬유 중합체 조성물 및 방법
US8728454B1 (en) 2012-10-30 2014-05-20 The Clorox Company Cationic micelles with anionic polymeric counterions compositions thereof
US8765114B2 (en) 2012-10-30 2014-07-01 The Clorox Company Anionic micelles with cationic polymeric counterions methods thereof
US8728530B1 (en) 2012-10-30 2014-05-20 The Clorox Company Anionic micelles with cationic polymeric counterions compositions thereof
US8883706B2 (en) 2012-10-30 2014-11-11 The Clorox Company Anionic micelles with cationic polymeric counterions systems thereof
US8883705B2 (en) 2012-10-30 2014-11-11 The Clorox Company Cationic micelles with anionic polymeric counterions systems thereof
US8933010B2 (en) 2012-10-30 2015-01-13 The Clorox Company Cationic micelles with anionic polymeric counterions compositions thereof
CN104762812A (zh) * 2015-03-11 2015-07-08 刘晓 一种衣物柔顺剂
WO2018044639A1 (en) * 2016-08-31 2018-03-08 The Procter & Gamble Company Fabric enhancer composition
US10487292B2 (en) 2016-08-31 2019-11-26 The Procter & Gamble Company Fabric enhancer composition
WO2022042277A1 (en) * 2020-08-28 2022-03-03 Ecolab Usa Inc. Method and extraction agent for methanol to olefins wash water system antifouling

Also Published As

Publication number Publication date
JPH024709B2 (de) 1990-01-30
JPH01250473A (ja) 1989-10-05
EP0335404A3 (de) 1990-12-27

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