EP0503155A1 - Adoucissant pour textile à base d'esters de poly(oxyalkylène)-alkanolamines quaternaires - Google Patents
Adoucissant pour textile à base d'esters de poly(oxyalkylène)-alkanolamines quaternaires Download PDFInfo
- Publication number
- EP0503155A1 EP0503155A1 EP19910121957 EP91121957A EP0503155A1 EP 0503155 A1 EP0503155 A1 EP 0503155A1 EP 19910121957 EP19910121957 EP 19910121957 EP 91121957 A EP91121957 A EP 91121957A EP 0503155 A1 EP0503155 A1 EP 0503155A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- compounds
- general formula
- weight
- radicals
- carbon atoms
- 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
- RIRARCHMRDHZAR-UHFFFAOYSA-N CC1C(C)CCC1 Chemical compound CC1C(C)CCC1 RIRARCHMRDHZAR-UHFFFAOYSA-N 0.000 description 1
- SDLWJGWWYARDEO-UHFFFAOYSA-N CC[O](C)CCN Chemical compound CC[O](C)CCN SDLWJGWWYARDEO-UHFFFAOYSA-N 0.000 description 1
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
- 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
- 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
- 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 fabric softeners in the form of aqueous solutions, emulsions or dispersions.
- Cationic compounds are usually used as fabric softeners, for example quaternary ammonium compounds which, in addition to long-chain alkyl radicals, can also contain ester or amide groups. Mixtures of various softening components which are added to the rinsing bath in the form of aqueous dispersions are also advantageously used.
- Backwetting capacity is generally understood to mean the absorption of moisture by the fiber. Poor network assets have an adverse effect where larger amounts of moisture are to be absorbed from the skin surface by textile fabrics, e.g. B. with hand or bath towels as well as with body or bed linen.
- fabric softening agents consisting of ammonium compounds containing ester groups and a liquid carrier material meet these requirements.
- the polyoxyalkylene alcohols are prepared by adding an alkylene oxide, essentially propylene oxide, ethylene oxide or a mixture of both, using a conventional method to a compound containing one or more active hydrogen atoms or by polymerizing alkylene oxides.
- Monoalcohols such as ethanol, isopropanol, butanol, lauryl alcohol, stearyl alcohol, but especially methanol or glycols such as ethylene glycol, propylene glycol, diethylene glycol, glycerol, trimethylolpropane, pentaerythritol, sorbitol, polyglycerol, polyvinyl alcohols can be used as compounds which contain one or more active hydrogen atoms.
- the polyoxyalkylene alcohols have molecular weights in the range from approximately 100 to 10,000, preferably approximately 130 to 5000 and particularly preferably approximately 150 to 2000.
- the further conversion to the amines is carried out according to methods known per se by aminolysis of the free hydroxyl groups or their esters, in particular the sulfuric acid esters.
- the OH group is replaced by the amino group by means of homogeneous, but in particular heterogeneous, catalysis on fixed contacts.
- two methods are available here. The one works with dehydrating, the other with hydrodehydrogenating catalysts.
- the following compounds of formula (2) were preferred:
- the compounds of the formula (2) are then alkoxylated, ie preferably ethoxylated or propoxylated, by processes known per se.
- the procedure is such that the amines in a pressure reactor at 120-160 ° C., optionally in the presence of basic, in particular alkaline, catalysts at 1-4 bar with an amount of alkylene oxide corresponding to the desired degree of alkoxylation; ethylene oxide and propylene oxide are preferred according to the invention or their mixtures, reacted.
- the fatty acids for the esterification or the transesterification are the monobasic synthetic fatty acids known and customary in this field, but in particular the fatty acids based on natural vegetable and animal oils with 6-22 C atoms, in particular with 8-18 C atoms, such as coconut fatty acids, palm, tallow, castor fatty acids. These can be used both as glycerides, as esters with short-chain alcohols or as free acids.
- the alkanolamines of the formula (4) are reacted with an amount of fatty acid or fatty acid ester corresponding to the desired degree of esterification, if appropriate in the presence of a catalyst, at 160-240 ° C. and the water of reaction or alcohol which is formed is distilled off continuously, to complete the If necessary, a negative pressure is applied.
- the salts are generally prepared by adding the acids, if appropriate as aqueous or alcoholic solutions in an amount corresponding to the desired degree of salt formation, to the poly (oxyalkylene) alkanolamine esters at 20 ° -80 ° C. and, if necessary with stirring, in portions with cooling.
- the quaternization is carried out in accordance with the generally known processes, the poly (oxyalkylene) alkanolamine esters, optionally with the use of a solvent, being heated to 40-80 ° C. and the quaternizing agent being added in portions in an amount corresponding to the desired degree of quaternization.
- the anions are particularly preferred according to the invention where several anions can also be present side by side and are added in an amount such that the resulting pH of the total mixture of a 30% mixture is between 2-6, preferably 3-5.
- the compounds of the general formula (1) which are also used according to the invention can be used alone or as mixtures, with - in a certain dependence on the structure of the compounds of the general formula (3) - the triesters of the general formula (1) predominantly in dispersions, the diesters of the general formula (1) can be converted into solutions.
- the diester compounds are prepared by simply dissolving in cold or accelerated in heated water, as described, the triester compounds are emulsified or dispersed by the known processes, with the customary equipment and the known auxiliaries and additives also being used.
- the compounds according to the invention can also be used at room temperature (20-25 ° C.) be incorporated. While stirring well, the dye solution, then the antifoam emulsion that may be required and finally the individual plasticizers are dispersed in succession or in a mixture. After adding a portion of an electrolyte solution (if necessary), perfume oil is added, followed by the remaining amount of the electrolyte solution. According to the invention, it is preferred to work without adding electrolyte solutions.
- the customary auxiliaries and additives can also be used to prepare the fabric softening agents according to the invention.
- these are, in particular, dyes and fragrances, electrolytes and higher molecular weight ether compounds for viscosity regulation, small amounts of organic solvents and - provided they do not adversely affect the rewetting capacity - customary cationic and / or nonionic surfactants.
- fabric softeners By combining the components according to general formula (1) and, if appropriate, the commercially available quaternary ammonium compounds and optionally auxiliaries, fabric softeners can be produced which are clearly soluble in water or have good emulsifying or dispersing properties and give textile materials, in particular those made from natural and regenerated cellulose, as well as wool and terry cloth, an improved softness and an improved rewetting capacity.
- the fabric softeners according to the invention are therefore used in particular where larger amounts of moisture and moisture are to be removed from the body surface within a short time, such as in the case of hand towels or bath towels.
- the fabric softeners according to the invention can also be used successfully where moisture has to be absorbed directly by the skin within a relatively long period of time, such as for bedclothes or bed linen.
- the fabric softeners according to the invention are added in the last rinse cycle after the actual washing process.
- the application concentration after dilution with water is in the range of 0.1 - 10 g of fabric softener per liter of treatment liquor.
- GAZ Total amine number
- TEZ tertiary amine number
- the total amine number indicates the number of milligrams of potassium hydroxide equivalent to the total amine basicity of 1 g of the amine compound (mg KOH / g).
- the tertiary amine number indicates the number of milligrams of potassium hydroxide equivalent to the tertiary amine basicity of 1 g of the amine compound.
- the values are determined according to AOCS Official Method Tf 2a - 64.
- the saponification number is a measure of the free and bound acids contained in fats and technical fatty acids. It specifies the number of milligrams of potassium hydroxide required to saponify 1 gram of fat or technical fatty acids (mg KOH / g). The values are determined according to the standard methods of the German Society for Fat Chemistry (DGF): DGF C-V3.
- the hydroxyl number is used to determine the hydroxyl group content and indicates the number of milligrams of potassium hydroxide required to neutralize the acetic acid consumed by 1 gram of fat in acetylation (mg KOH / g). The values are determined according to the DGF standard method C-V17a.
- the acid number is a measure of the fat or technical fatty acid content of free acids and gives the milligrams of potassium hydroxide that are necessary to neutralize 1 gram of substance.
- the values are determined according to the DGF standard method C-V4.
- Cation-active substances are long-chain compounds which contain quaternary ammonium groups.
- the content is given in% quaternary compound, calculated as an SO3 equivalent with a molecular weight of 80 g / mol.
- the content is determined by a two-phase titration according to ISO standards 2871-1 and 2871-2 (1988 E).
- the mixture results in a homogeneous emulsion or solution.
- add further portions of electrolyte during emulsification. Stir the mixture to approx. 25 ° C.
- add the perfume oil while stirring and, if necessary, adjust the viscosity with the remaining amount of electrolyte.
- the mixture results in a homogeneous emulsion or solution.
- the textile material made of wool, cotton, polyester / cotton 50: 3 and polyester is soaked for about 10 minutes with a liquor of tap water (about 9 ° dH and a temperature of 15-20 ° C) and an emulsion according to the invention, Dispersion or solution treated.
- the concentration of the compounds according to the invention in the liquor is 0.025% by weight, based on the total active substance.
- the dried textiles were checked by nine people with appropriate experience in assessing the softness of textiles for their soft feel and compared to textiles not treated with fabric softeners. The assessment is based on a graded point system, with the final assessment being represented by the arithmetic mean. After drying, the textile goods treated in this way have an excellent soft, fluffy feel and a greatly improved rewetting capacity compared to commercially available agents.
Landscapes
- 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)
- Detergent Compositions (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4108025 | 1991-03-13 | ||
DE4108025A DE4108025A1 (de) | 1991-03-13 | 1991-03-13 | Waescheweichspuelmittel auf basis von quaternaeren poly(oxyalkylen)alkanolaminestern |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0503155A1 true EP0503155A1 (fr) | 1992-09-16 |
EP0503155B1 EP0503155B1 (fr) | 1996-05-01 |
Family
ID=6427124
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP91121957A Expired - Lifetime EP0503155B1 (fr) | 1991-03-13 | 1991-12-20 | Adoucissant pour textile à base d'esters de poly(oxyalkylène)-alkanolamines quaternaires |
Country Status (5)
Country | Link |
---|---|
US (1) | US5254270A (fr) |
EP (1) | EP0503155B1 (fr) |
CA (1) | CA2062848A1 (fr) |
DE (2) | DE4108025A1 (fr) |
ES (1) | ES2089104T3 (fr) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995004184A1 (fr) * | 1993-08-02 | 1995-02-09 | The Procter & Gamble Company | Emulsions super concentrees renfermant des agents actifs d'adoucissant textile |
EP0669391A2 (fr) * | 1994-02-23 | 1995-08-30 | Witco Surfactants GmbH | Adoucissants aqueux très concentré ayant une stabilité au stockage améliorée |
US5750491A (en) * | 1993-08-02 | 1998-05-12 | The Procter & Gamble Company | Super concentrate emulsions with fabric actives |
WO2001002523A1 (fr) * | 1999-07-06 | 2001-01-11 | The Procter & Gamble Company | Compositions aqueuses adoucissantes limpides ou translucides pour textiles, a l'ammonium polyquaternaire, contenant une faible quantite de solvant |
US6884767B1 (en) | 1999-07-06 | 2005-04-26 | The Procter & Gamble Company | Clear or translucent aqueous polyquaternary ammonium fabric softener compositions containing low solvent |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7371718B2 (en) * | 2005-04-22 | 2008-05-13 | The Dial Corporation | Liquid fabric softener |
MX2010002308A (es) * | 2007-08-31 | 2010-03-18 | Procter & Gamble | Composiciones y metodos para cambiar la percepcion visual. |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0295386A2 (fr) * | 1987-06-19 | 1988-12-21 | Hüls Aktiengesellschaft | Compositions adoucissantes concentrées |
EP0296995A1 (fr) * | 1987-06-16 | 1988-12-28 | Cotelle S.A. | Compositions adoucissantes concentrées |
EP0345842A2 (fr) * | 1988-05-27 | 1989-12-13 | The Procter & Gamble Company | Compositions adoucissantes pour le linge contenant des mélanges des esters d'imidazoline substitués et des sels quaternaires d'ammonium ester |
EP0413249A1 (fr) * | 1989-08-12 | 1991-02-20 | Witco Surfactants GmbH | Adoucissant pour textile |
EP0461419A1 (fr) * | 1990-06-12 | 1991-12-18 | REWO Chemische Werke GmbH | Esters de poly(oxyalkylène)aminoalkanols, leurs sels d'ammonium, procédés pour leur préparation et leur utilisation comme lessives, agents de nettoyage, désinfectants et conservateurs |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB384714A (en) * | 1930-08-27 | 1932-12-15 | Du Pont | Improvements in or relating to the catalytic production of amines from alcohols and a |
US2017051A (en) * | 1931-02-06 | 1935-10-15 | Du Pont | Synthesis of amines |
US2078922A (en) * | 1934-06-28 | 1937-05-04 | Du Pont | Synthesis of higher amines |
MY103439A (en) * | 1987-10-29 | 1993-06-30 | Kao Corp | Detergent composition |
DE68919236T2 (de) * | 1988-01-28 | 1995-04-06 | Unilever Nv | Textilbehandlungszubereitung und deren Herstellung. |
US4946627A (en) * | 1989-07-19 | 1990-08-07 | National Starch And Chemical Investment Holding Corporation | Hydrophobically modified polycarboxylate polymers utilized as detergent builders |
-
1991
- 1991-03-13 DE DE4108025A patent/DE4108025A1/de not_active Withdrawn
- 1991-12-20 ES ES91121957T patent/ES2089104T3/es not_active Expired - Lifetime
- 1991-12-20 DE DE59107766T patent/DE59107766D1/de not_active Expired - Lifetime
- 1991-12-20 EP EP91121957A patent/EP0503155B1/fr not_active Expired - Lifetime
-
1992
- 1992-03-12 CA CA002062848A patent/CA2062848A1/fr not_active Abandoned
- 1992-03-13 US US07/850,578 patent/US5254270A/en not_active Expired - Fee Related
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0296995A1 (fr) * | 1987-06-16 | 1988-12-28 | Cotelle S.A. | Compositions adoucissantes concentrées |
EP0295386A2 (fr) * | 1987-06-19 | 1988-12-21 | Hüls Aktiengesellschaft | Compositions adoucissantes concentrées |
EP0345842A2 (fr) * | 1988-05-27 | 1989-12-13 | The Procter & Gamble Company | Compositions adoucissantes pour le linge contenant des mélanges des esters d'imidazoline substitués et des sels quaternaires d'ammonium ester |
EP0413249A1 (fr) * | 1989-08-12 | 1991-02-20 | Witco Surfactants GmbH | Adoucissant pour textile |
EP0461419A1 (fr) * | 1990-06-12 | 1991-12-18 | REWO Chemische Werke GmbH | Esters de poly(oxyalkylène)aminoalkanols, leurs sels d'ammonium, procédés pour leur préparation et leur utilisation comme lessives, agents de nettoyage, désinfectants et conservateurs |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995004184A1 (fr) * | 1993-08-02 | 1995-02-09 | The Procter & Gamble Company | Emulsions super concentrees renfermant des agents actifs d'adoucissant textile |
US5750491A (en) * | 1993-08-02 | 1998-05-12 | The Procter & Gamble Company | Super concentrate emulsions with fabric actives |
EP0669391A2 (fr) * | 1994-02-23 | 1995-08-30 | Witco Surfactants GmbH | Adoucissants aqueux très concentré ayant une stabilité au stockage améliorée |
EP0669391A3 (fr) * | 1994-02-23 | 1998-08-19 | Witco Surfactants GmbH | Adoucissants aqueux très concentré ayant une stabilité au stockage améliorée |
WO2001002523A1 (fr) * | 1999-07-06 | 2001-01-11 | The Procter & Gamble Company | Compositions aqueuses adoucissantes limpides ou translucides pour textiles, a l'ammonium polyquaternaire, contenant une faible quantite de solvant |
US6884767B1 (en) | 1999-07-06 | 2005-04-26 | The Procter & Gamble Company | Clear or translucent aqueous polyquaternary ammonium fabric softener compositions containing low solvent |
US7018974B2 (en) | 1999-07-06 | 2006-03-28 | The Procter & Gamble Company | Clear or translucent aqueous polyquaternary ammonium fabric softener compositions containing low solvent |
Also Published As
Publication number | Publication date |
---|---|
ES2089104T3 (es) | 1996-10-01 |
CA2062848A1 (fr) | 1992-09-14 |
DE4108025A1 (de) | 1992-09-17 |
EP0503155B1 (fr) | 1996-05-01 |
US5254270A (en) | 1993-10-19 |
DE59107766D1 (de) | 1996-06-05 |
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