EP0792337A1 - Agents assouplissants pour textiles - Google Patents
Agents assouplissants pour textilesInfo
- Publication number
- EP0792337A1 EP0792337A1 EP95937869A EP95937869A EP0792337A1 EP 0792337 A1 EP0792337 A1 EP 0792337A1 EP 95937869 A EP95937869 A EP 95937869A EP 95937869 A EP95937869 A EP 95937869A EP 0792337 A1 EP0792337 A1 EP 0792337A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- carbon atoms
- alkyl
- group
- alkenyl
- textile
- 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.)
- Granted
Links
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
- C11D3/001—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
- C11D1/66—Non-ionic compounds
- C11D1/835—Mixtures of non-ionic with cationic compounds
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/144—Alcohols; Metal alcoholates
- D06M13/148—Polyalcohols, e.g. glycerol or glucose
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
-
- 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
- C11D1/662—Carbohydrates or derivatives
-
- 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
- C11D1/667—Neutral esters, e.g. sorbitan esters
-
- 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
-
- 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
- C11D1/721—End blocked ethers
-
- 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
- C11D1/74—Carboxylates or sulfonates esters of polyoxyalkylene glycols
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/50—Modified hand or grip properties; Softening compositions
Definitions
- the invention lies in the general field of textile treatment agents for the household and in textile technology and relates to agents for textiles which give them excellent softness.
- the textile softening agents contain sugar derivatives which carry ecologically very well tolerated alkyl, alkenyl and / or acyl residues, as well as special combinations of non-ionic and cationic emulsifiers.
- the special combination of non-ionic emulsifiers and cationic emulsifiers has the effect that the softness of the plasticizers does not deteriorate and stable aqueous dispersions of the plasticizers are possible over a wide range of concentrations.
- Plasticizers are used in textile technology and in the home for finishing, for example to produce a pleasant, fluffy feel, to increase wearing comfort, to improve the processing properties or also to care for the textiles Quaternary ammonium compounds are used, since they are particularly easy to pull onto textiles.
- plasticizers which contain compounds as main plasticizing components which no longer have any quaternary nitrogen groups.
- the requirements are met if the textile softening agents contain sugar derivatives carrying alkyl, alkenyl and / or acyl residues as the main softening components, and special emulsifier combinations of nonionic emulsifiers and cationic emulsifiers.
- R5 is an aliphatic hydrocarbon radical having 1 to 4 carbon atoms or the group (CH2CHR7 ⁇ ) 0 H, where R7 * H or CH3 and 0 is a number from 1 to 20 and
- sucrose derivatives includes derivatives of mono- and / or disaccharides and of oligoglycosides. This also includes the derivatives of hydrogenated monosaccharides such as xylitol, sorbitol and sorbitan. Furthermore, the terms “main plasticizing component” and “plasticizer” are used synonymously in the present application.
- the mono- and / or disaccharides and the oligoglycosides carry at least one, preferably at least two, alkyl, alkenyl and / or acyl radicals which have 8 to 24 carbon atoms.
- the alkyl, alkenyl and / or acyl radicals having 8 to 24 carbon atoms can be glycosidically or linked to the sugars via an ester bond.
- the sugars it is possible for the sugars to carry, in addition to the two alkyl, alkenyl and / or acyl radicals having 8 to 24 carbon atoms, further alkyl, alkenyl and / or acyl radicals, these further radicals having no restriction on C.
- These further radicals which may also be glycosidically linked or linked to the sugars via an ester compound, preferably have 1 to 24 carbon atoms.
- the highest possible number of alkyl, alkenyl and / or acyl residues results from the number of free OH groups of the sugar, it being preferred for the mono- and disaccharides that at least one free OH group and Preferred at least 2 free OH groups remain. For the monosaccharides and disaccharides, it is recommended that about half of the free OH groups originally present remain free, and the rest, linked, carries the alkyl, alkenyl and / or acyl radicals.
- Suitable mono- and / or disaccharides are glucose, mannose, galactose, xylose, maltose, lactose, sucrose and Cl-C4-alkyl glycosides such as methyl glucoside.
- suitable hydrogenated monosaccharides are xylitol, sorbitan and sorbitol. Of these, glucose, methyl glucoside and sucrose are preferred.
- alkyl and / or alkenyl oligoglycosides are preferred which are derived from aldoses or ketoses and, because of their ready availability, in particular from glucose, so that [G] in formula (IV) preferably represents glucose.
- the index number p in the general formula (IV) indicates the degree of oligomerization (DP degree), ie the number of aldoses or ketoses linked to one another by glycosides.
- DP degree degree of oligomerization
- the value p is an analytically determined arithmetic parameter, which usually represents a fractional number.
- Alkyl and / or alkenyl oligoglycosides with an average degree of oligomerization p of 1.1 to 3.0 are preferred; those alkyl and / or alkenyl oligoglycosides whose degree of oligomerization is between 1.2 and 1.7 are particularly preferred.
- the sugars carry at least one, preferably at least two alkyl, alkenyl and / or acyl radicals which have 8 to 24 carbon atoms.
- R ⁇ in the formula (IV) is an alkyl or alkenyl radical having 1 to 7 carbon atoms, this means that those from the group of the alkyl and / or alkenyl glycosides of the formula (IV) are particularly preferred, the two further alkyl, alkenyl and / or acyl radicals with 8 to 24 carbon atoms in order to arrive at the particularly preferred sugar derivatives with at least two alkyl, alkenyl and / or acyl radicals with 8 to 24 carbon atoms.
- Very particularly preferred examples from the group of mono- and disaccharides are methyl glucoside difatty acid esters such as methyl glucoside distearate and sucrose tetrafatty acid esters such as sucrose tetrastearate.
- Suitable examples from the group of alkyl and / or alkenyl oligoglycosides are fatty alkyl oligoglucoside fatty acid monoesters such as lauryl oligoglucoside lauric acid ester, lauryl oligoglucoside stearic acid ester and stearyl oligoglucoside stearyl acid ester, the degree of oligomerization being between 1.2 and 1.7.
- Suitable examples from the group of hydrogenated monosaccharides are sorbitan ono and trifatty acid esters such as sorbitan mono and tristearate.
- the textile plasticizers according to the invention contain emulsifier combinations of nonionic and cationic emulsifiers as plasticizers.
- Quaternized alkoxylated alkylamines of the formula (I), quaternized fatty acid alkanolamine esters of the general formula (II) and / or quaternized alkylamines of the formula (III) are present as cationic emulsifiers.
- R represents an aliphatic hydrocarbon radical having 12 to 22 carbon atoms and x, y, z independently of one another represent a number from 1 to 10, the sum of x + y + z is in the range from 3 to 10.
- the quaternized ethoxylated alkylamines (R'-H) are particularly suitable.
- esterquats are also known compounds which can be obtained by the relevant methods of preparative chemistry and are usually referred to as "esterquats".
- WO 91/01295 describes a process for their preparation, according to which fatty acids are reacted with triethanolamine in the presence of reducing agents and with passage of air, and the diesters obtained are then quaternized with alkylating agents such as dimethyl sulfate, trimethyl phosphate or methyl halide. Since these are technical products, the ester quats of the general formula (II) are always mixtures of quaternized mono-, di- and tri-esters. If desired, the ester quats can be used in the form of organic solutions, for example dissolved in a branched lower alcohol such as isopropanol.
- R ⁇ O represents an acyl group which is derived from pure fatty acids or technical mixtures of fatty acids such as lauric, myristic, palmitic, stearic, derives oleic, elaidic, petroselinic, linoleic, linolenic, arachic, behenic and / or erucic acid.
- R C0 very particularly preferably stands for a saturated acyl group with 16 and / or 18 C atoms, R3 for a methyl group, m for the number 2, u, v and w for the number 1 and A ⁇ for a halide, methosulfate or methophosphate.
- the quaternized alkylamines of the formula (III) are also known compounds.
- the neutralized tertiary amines falling under this group (R8 stands for H) can be neutralized by trialkylamines (R5 and R *> standing for an aliphatic hydrocarbon residue) or alkoxyalkylamines (R-5 and / or R ⁇ standing for the group) (CH2CHR 7 0) n H).
- Inorganic acids such as hydrochloric acid are preferably used for neutralization.
- the neutralization is preferably carried out in situ, ie the non-neutralized amines are used and the pH of the aqueous dispersions of the plasticizer according to the invention is adjusted from neutral to acidic by adding inorganic acids, as a result of which the neutralization of the tertiary amines is achieved.
- Non-ionic emulsifiers are contained in the textile softening agents as a further emulsifier component.
- Non-ionic emulsifiers which can be used are those known from the prior art, especially those which have no tendency to swell when emulsified in water.
- Particularly suitable nonionic emulsifiers are compounds selected from the group consisting of b1) ethoxylated and / or propoxylated fatty acids and / or ethoxylated and / or propoxylated fatty acid esters and b2) fatty alcohol polyglycol ethers and / or end group-capped fatty alcohol polyglycol ethers and b3) alkyl and / or alkenyl oligoglycosides.
- Ethoxylated and / or propoxylated fatty acids or fatty acid esters are also known compounds which are obtained by ethoxy and / or propoxylation of the fatty acids or fatty acid esters in the presence of catalysts.
- a process is known from DE-A-40 10 606, according to which ethoxylated and / or propoxylated fatty acid esters with a narrow homolog distribution are obtained, provided that the work is carried out in the presence of hydrophobized hydrotalils as catalysts.
- the optionally end-capped fatty alcohol polyglycol ethers are also a known class of compounds which can be prepared by appropriate methods in organic chemistry, for example by reacting alkyl halides with ethoxylated and / or propoxylated fatty alcohols in the presence of a catalyst.
- the fatty alcohol polyglycol ethers can be prepared by known ethoxylation and / or propoxylation of fatty alcohols.
- R 12 is an aliphatic hydrocarbon radical having 12 to 22 C atoms
- s is a number from 2 to 8
- t is a number from 0 to 5
- R 13 represents hydrogen or an alkyl radical having 1 to 4 carbon atoms.
- R 12 can be derived from pure fatty alcohols or technical mixtures of fatty alcohols such as lauryl, myristyl, palmityl, stearyl, arachidyl, behenyl, oleyl, elaidyl, linoleyl and / or linolenyl alcohol.
- alkyl and / or alkenyl oligoglycosides are also a known class of compounds which can be prepared, for example, by the acid-catalyzed acetalization of glucose with fatty alcohols.
- EP-A-0 301 298 As a representative of the large number of literature, reference is made to the European patent application EP-A-0 301 298. Suitable alkyl and / or alkenyl oligoglycosides have been described in connection with formula (IV) of the present patent application.
- nonionic emulsifiers are added at least in the same weight ratio, but preferably in smaller amounts in relation to the cationic emulsifiers.
- Preferred weight ratios of nonionic emulsifiers to cationic emulsifiers are 1: 1 to 3: 1, preferably 1.5: 1 to 2: 1.
- the textile plasticizers contain the plasticizer in amounts of 60 to 95% by weight, the emulsifier combination in amounts of 5 to 40% by weight and, if appropriate, in amounts of 0 to 20% by weight of customary auxiliaries.
- the textile plasticizers preferably contain 70 to 90% by weight of the plasticizer, the emulsifier combination in amounts of 10 to 30% by weight and 0 to 20% by weight of customary auxiliaries.
- the amounts given relate to the active substance salary. Active substance content is understood to mean the content of plasticizers, emulsifiers and conventional auxiliaries, but not water.
- Typical auxiliaries are, for example, pH regulators such as organic and inorganic acids, foam inhibitors, viscosity regulators, antioxidants, colorants, fragrances and soil release active substances. If the not yet neutralized tertiary alkylamines are used as cationic emulsifiers, the addition of acids, as already described, is absolutely necessary to adjust the pH.
- the textile softening agents are generally used in the form of their aqueous dispersions.
- the usual concentrations of 3 to 6% by weight - based on the active substance content - are set.
- it is also possible to prepare higher concentrates with 10 to 30% by weight of active substance and either subsequently dilute to 3 to 6% by weight or correspondingly smaller amounts are added to the last rinsing bath.
- the textile softening agents can also be used in textile technology in the concentrations customary for this purpose, since they can easily be applied by customary methods such as pull-out, immersion centrifugal, padding or spraying methods.
- Another object of the present invention relates to a process for the production of textile softening agents according to claim 1, characterized in that the alkyl, alkenyl and / or acyl residues with 8 to 24 carbon atoms are melted and melted with the katio ⁇ African Emulsifiers are added before they are then added to the aqueous solutions or dispersions of the nonionic emulsifiers.
- Another subject relates to the use of alkyl, alkenyl and / or acyl radicals having sugar derivatives bearing 8 to 24 carbon atoms in a mixture with nonionic emulsifiers and cationic emulsifiers, selected from the group al), a2) and / or a3) from claim 1, in the form of their aqueous dispersions for softening household linen or as softening aftertreatment agent in textile technology.
- an aqueous dispersion was prepared, but with 5 g of sucrose tetrastearate instead of the glucoside derivative.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4440620A DE4440620A1 (de) | 1994-11-14 | 1994-11-14 | Textile Weichmachungsmittel |
DE4440620 | 1994-11-14 | ||
PCT/EP1995/004349 WO1996015213A1 (fr) | 1994-11-14 | 1995-11-06 | Agents assouplissants pour textiles |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0792337A1 true EP0792337A1 (fr) | 1997-09-03 |
EP0792337B1 EP0792337B1 (fr) | 1999-02-03 |
Family
ID=6533271
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP95937869A Expired - Lifetime EP0792337B1 (fr) | 1994-11-14 | 1995-11-06 | Agents assouplissants pour textiles |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0792337B1 (fr) |
AT (1) | ATE176494T1 (fr) |
DE (2) | DE4440620A1 (fr) |
ES (1) | ES2128785T3 (fr) |
WO (1) | WO1996015213A1 (fr) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR9713213A (pt) | 1996-09-19 | 2000-04-04 | Procter & Gamble | Composições amaciantes para tecido concentradas de amÈnio quaternário contendo polìmeros catiÈnicos. |
BR9711906A (pt) * | 1996-10-16 | 1999-08-24 | Unilever Nv | Composi-Æo amaciante de tecidos usos de um cpe ou rse e de um mono di ou trioleato de sorbitano e -ster de cido graxo l¡quido ou sÄlido mole de glicose |
GB9911437D0 (en) | 1999-05-17 | 1999-07-14 | Unilever Plc | Fabric softening compositions |
GB9911434D0 (en) * | 1999-05-17 | 1999-07-14 | Unilever Plc | Fabric softening compositions |
GB9930430D0 (en) * | 1999-12-22 | 2000-02-16 | Unilever Plc | A method of preparing fabric softening compositions |
GB9930435D0 (en) * | 1999-12-22 | 2000-02-16 | Unilever Plc | Fabric softening compositions |
GB9930436D0 (en) * | 1999-12-22 | 2000-02-16 | Unilever Plc | A method of stabilising fabric softening compositions |
GB9930437D0 (en) * | 1999-12-22 | 2000-02-16 | Unilever Plc | Fabric softening compositions and compounds |
GB0213263D0 (en) | 2002-06-10 | 2002-07-17 | Unilever Plc | Improvements relating to fabric detergent compositions |
US7135451B2 (en) | 2003-03-25 | 2006-11-14 | The Procter & Gamble Company | Fabric care compositions comprising cationic starch |
US7776813B2 (en) | 2004-09-15 | 2010-08-17 | The Procter & Gamble Company | Fabric care compositions comprising polyol based fabric care materials and deposition agents |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4804497A (en) * | 1985-09-26 | 1989-02-14 | A. E. Staley Manufacturing Company | Fine fabric detergent composition |
IL81353A (en) * | 1986-01-30 | 1990-08-31 | Colgate Palmolive Co | Liquid softergent having improved detergency containing alkyl glycoside |
DE3612479A1 (de) * | 1986-04-14 | 1987-10-15 | Henkel Kgaa | Waessriges konzentriertes textilweichmachungsmittel |
DE4125025A1 (de) * | 1991-07-29 | 1993-02-04 | Henkel Kgaa | Fluessiges waschmittel |
EP0659207B1 (fr) * | 1992-09-11 | 1999-03-24 | Henkel Kommanditgesellschaft auf Aktien | Utilisation de melanges de detergents |
DE4301459A1 (de) * | 1993-01-20 | 1994-07-21 | Huels Chemische Werke Ag | Wäßriges Weichspülmittel für die Behandlung von Textilien |
-
1994
- 1994-11-14 DE DE4440620A patent/DE4440620A1/de not_active Withdrawn
-
1995
- 1995-11-06 DE DE59505051T patent/DE59505051D1/de not_active Expired - Lifetime
- 1995-11-06 WO PCT/EP1995/004349 patent/WO1996015213A1/fr active IP Right Grant
- 1995-11-06 ES ES95937869T patent/ES2128785T3/es not_active Expired - Lifetime
- 1995-11-06 AT AT95937869T patent/ATE176494T1/de not_active IP Right Cessation
- 1995-11-06 EP EP95937869A patent/EP0792337B1/fr not_active Expired - Lifetime
Non-Patent Citations (1)
Title |
---|
See references of WO9615213A1 * |
Also Published As
Publication number | Publication date |
---|---|
ATE176494T1 (de) | 1999-02-15 |
DE59505051D1 (de) | 1999-03-18 |
WO1996015213A1 (fr) | 1996-05-23 |
DE4440620A1 (de) | 1996-05-15 |
ES2128785T3 (es) | 1999-05-16 |
EP0792337B1 (fr) | 1999-02-03 |
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