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WO1994004642A2 - Composition de conditionnement de tissus - Google Patents

Composition de conditionnement de tissus Download PDF

Info

Publication number
WO1994004642A2
WO1994004642A2 PCT/US1993/007612 US9307612W WO9404642A2 WO 1994004642 A2 WO1994004642 A2 WO 1994004642A2 US 9307612 W US9307612 W US 9307612W WO 9404642 A2 WO9404642 A2 WO 9404642A2
Authority
WO
WIPO (PCT)
Prior art keywords
acid
fabric conditioning
conditioning composition
weight
mineral
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.)
Ceased
Application number
PCT/US1993/007612
Other languages
English (en)
Other versions
WO1994004642A3 (fr
Inventor
Subhash Harmalker
Jean-Paul Grandmaire
Viviane Tack
Alain Jacques
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.)
Colgate Palmolive Co
Original Assignee
Colgate Palmolive Co
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 Colgate Palmolive Co filed Critical Colgate Palmolive Co
Priority to EP93920022A priority Critical patent/EP0658185A1/fr
Publication of WO1994004642A2 publication Critical patent/WO1994004642A2/fr
Publication of WO1994004642A3 publication Critical patent/WO1994004642A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/04—Water-soluble compounds
    • C11D3/042—Acids
    • 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
    • C11D1/46—Esters of carboxylic acids with amino alcohols; Esters of amino carboxylic acids with alcohols
    • 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
    • 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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2075—Carboxylic acids-salts thereof
    • C11D3/2079—Monocarboxylic acids-salts thereof
    • 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
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2075—Carboxylic acids-salts thereof
    • C11D3/2082—Polycarboxylic acids-salts thereof
    • 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
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2075—Carboxylic acids-salts thereof
    • C11D3/2086—Hydroxy carboxylic acids-salts thereof

Definitions

  • This invention relates to fabric conditioning compositions which are suitable for softening in the rinse cycle of an automatic household washing machine, and which are especially adapted for use under European laundering conditions. More particularly, the present invention relates to fabric conditioning compositions comprising defined tertiary amine diester in combination with an acid and optionally a fatty alcohol, which compositions are characterized by superior environmental compatibility relative to conventional tertiary amine or quaternary ammonium fabric softening compositions concomitant with providing improved calcium salt solubilization and reduction of encrustation on treated fabrics.
  • the combination of organic acid with cationic fabric softener such as amines and quaternary ammonium compounds is extensively disclosed in the prior art.
  • 3,904,359 and 3,954,630 to Ramachandran disclose a fabric treating composition
  • a fabric treating composition comprising a complexing acid such as citric or maleic acid in combination with a quaternary ammonium compound or amines such as primary tallow and primary coco amine.
  • the function of the acid is to prevent yellowing of fabrics due to build-up of cationic softener and to provide a complexing site for metal ions contained in soils.
  • European Patent Publication No. 123,400 to Kardouch discloses detergent compositions containing salts of specified tertiary amines and carboxylic acids which are utilized in the form of modules that pass virtually unchanged through the wash and rinse and then condition the fabric when heated in a dryer.
  • European Patent Publication No. 417,987 describes fabric softening compositions comprised of tertiary amines and carboxylic acids.
  • the present invention provides environmentally compatible and biodegradable rinse cycle fabric conditioning compositions capable of providing improved softening with significant reduction and solubilization of unwanted mineral encrustations on fabrics to be softened, such encrustations having been generally deposited on the fabrics during the course of prior laundering in water having a high mineral content, which comprises a fabric conditioning mixture of:
  • R-, and R 2 are each independently hydrogenated tallow or soft tallow; and n and m are integers from 1 to 4; and
  • the fabric softening composition further contains from about 0.2 to about 5%, by weight, preferably from about 0.5 to about 3%, and most preferably from about 0.5 to 1%, by weight, of a fatty alcohol having from about 10 to about 24 carbon atoms.
  • the integers n and m in the general formula are 2, and R-, and R 2 are hydrogenated tallow to provide a methyl diethanolamine-diester.
  • the invention also encompasses a method for softening fabrics and removing unwanted mineral encrustations therefrom comprising rinsing the fabrics to be treated in an aqueous bath containing an effective amount of a composition comprised of the above-defined fabric conditioning mixture.
  • the present invention is predicated on the discovery that the combination of diester amine fabric softener as defined above with an organic or mineral acid provides a biodegradable softener which has the capability of removing mineral encrustations such as calcium and magnesium salts, and in particular, phosphates and carbonates of calcium and magnesium, which cumulatively deposits on the fabrics during the course of prior laundering in hard water, i.e. water having a mineral content above about 300 ppm, conditions generally associated with European laundering conditions.
  • mineral encrustations such as calcium and magnesium salts, and in particular, phosphates and carbonates of calcium and magnesium
  • a particularly preferred softening compound as described herein comprises methyl diethanol amine diester sold by Hoechst Company.
  • compositions of the present invention are environmentally compatible and biodegradable rinse cycle fabric conditioning compositions which contain as the active fabric softening compound a methyl diester amine as defined above.
  • the use of such fabric softening compound avoids the more traditional di-long chain, di-short chain quaternary ammonium softeners which are used extensively in commercial rinse cycle softeners, but which presently have become the focus of increasing legislative concerns, particularly in Europe, because of their lack of biodegradability in aqueous effluent streams.
  • a preferred diester amine in accordance with the invention is Methyl Diethanol Amine Diester which is commercially available from Hoechst Company under the designation E91/50G and is based on H-tallow acid. It has the general formula shown below:
  • the total amount of diester amine in the total composition is from about 1 to 20%, by weight, preferably from about 2 to 10%, by weight.
  • the second essential ingredient of the fabric conditioning composition is the acid which has a dual function, depending on the acid concentration.
  • the first function is preventive in nature and occurs when the acid in the diluted rinse cycle solution is present in sufficient amount to react with the insoluble salts of the water hardness ions (calcium and magnesium) to form soluble acid salts and to remove any mineral salts which may have deposited on fabrics during the washing step of the wash cycle.
  • the second function is more curative in nature and refers to the removal of mineral encrustations which have been cumulatively deposited during prior washing throughout the fabric's life.
  • a dosage of 110 to 150 ml of softening composition is typical for use in the rinse cycle; the water hardness varies from about 200 to 400 ppm, most typically about 300 ppm.
  • an acid concentration of from about 5 to about 25%, by weight, preferably from about 8 to 25%, by weight is required in the fabric softening composition.
  • the acid used may be an organic or mineral acid.
  • the organic acids are preferably saturated or unsaturated C 2 -C 6 carboxylic acids such as citric acid, formic acid, maleic acid, tartaric acid and succinic acid. Citric acid, malonic acid and maleic acid are particularly preferred.
  • a mineral acid, such as HCI, which is particularly effective to protonate the diester amine softening compound, may be advantageously combined with such organic acid, the amount of acid used in excess of protonation being referred to herein as "unreacted".
  • the concentration of unreacted mineral acid should not exceed about 5%, preferably not more than 2%, by weight, of the fabric conditioning composition so as to prevent unwanted product separation.
  • a carboxylic acid may then be used to supplement the mineral acid up to a total acid content of about 25% without adversely affecting product stability.
  • An optional fabric conditioning ingredient is a fatty alcohol wherein the hydrophobic group may be a straight or branched chain alkyl or alkenyl group having from about 10 to 24, preferably from about 10 to 20, especially preferably from about 12 to 20 carbon atoms.
  • Specific examples of the fatty alcohol include decanol, dodecanol, tetradecanol, pentadecanol, hexadecanol, octadecanol, lauryl alcohol, palmityl alcohol, stearyl alcohol, oleyl alcohol, and mixtures thereof.
  • the fatty alcohol may be of natural or synthetic origin and my include, for example, mixed alcohol, such as C ⁇ 6 -C ⁇ 8 alcohols prepared by Ziegler polymerization of ethylene.
  • the fatty alcohol may be present in the composition in a minor amount relative to the cationic fabric softener such that the ratio, by weight, of the cationic fabric softener to fatty alcohol is in the range of from about 6:1 to 2:1 , preferably about 5:1 to 3:1, and most preferably about 4:1.
  • a fabric conditioning composition in accordance with the invention was formulated to have the following composition:
  • Nonionic detergent purchased from ICI comprised of a C ⁇ 3 -C 16 fatty alcohol ethoxylate with 20 moles of ethylene oxide per mole of alcohol.
  • Nonionic detergent purchased from Shell comprised of a C ⁇ 2 -C ⁇ 5 fatty alcohol ethoxylate with 3 moles of ethylene oxide per mole of alcohol.
  • the above composition was prepared by dissolving citric acid in water and the solution heated to 65°C. To the above solution, there was added the ester amine in melted form while mixing at 200 rpm. The surfactants and defoamer were then added under agitation and the resulting emulsion allow to stand overnight at room temperature. The emulsion was then homogenized at a pressure of 15,000 psi in a high pressure homogenizer (such as the Micro-Fluidizer purchased from Microfluidics Corp. of Mass., USA) to form particles of about 0.25 microns.
  • a high pressure homogenizer such as the Micro-Fluidizer purchased from Microfluidics Corp. of Mass., USA
  • Example 2 To provide a softness comparison of a conventional fabric softening composition with the composition of Example 1, the following reference composition was prepared comprising a diesterified quaternary ammonium compound in combination with fatty alcohol as the active softening components.
  • Stepantex VHR90 purchased from Stepan Chemical Co. consisting of di(stearoyl-oxyethyl-) methyl- hydroxyethyl ammonium.
  • the reference softening composition described above, and the fabric conditioning composition of Example 1 were evaluated for their softening efficacy using a standard procedure as follows: A mini-softening machine to simulate a European Miehle washing machine was used containing tap water at 20°C, fabric softening composition and the fabric to be softened. The softening cycle was 5 minutes under tumbling. A six times-washed and hardened towel was used as the fabric.
  • the relative amounts of water fabric softening composition, and fabric introduced into the machine corresponded to the ratio of 110 ml of softening product to 25 liters water to 3Kg of laundry which is commonly used in European Miehle washing machines. Accordingly, typical proportions used were 2 ml of softening product with 380 ml of water to soften 45 grams of hardened towel fabric in the softening machine.
  • the conditioned towels were evaluated by a six-member panel, each member assigning a softness rating from 1 to 10 where a rating of 1 corresponds to unso tened, harsh fabric and a rating of 10 represents the highest degree of fabric softness.
  • the composite panel softness rating for fabrics conditioned with the composition of Example 1 was 7.3, and the rating for fabrics conditioned with the reference composition was 7.7. A difference of 0.5 is considered statistically significant.

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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)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Inorganic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Biological Depolymerization Polymers (AREA)

Abstract

Une composition de conditionnement de tissus biodégradable et non nuisible à l'environnement permet d'assouplir davantage des tissus tout en réduisant et en solubilisant de manière significative les incrustations indésirables de minéraux sur les tissus à assouplir. La composition comprend un mélange assouplisseur de tissus constitué de (a) une amine de diester de méthyle ayant la formule générale (I), dans laquelle R1 et R2 désignent indépendamment l'un de l'autre de la graisse hydrogénée ou de la graisse non durcie; et n et m sont des nombres entiers compris entre 1 et 4; et (b) un acide organique ou minéral n'ayant pas réagi.
PCT/US1993/007612 1992-08-21 1993-08-17 Composition de conditionnement de tissus Ceased WO1994004642A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP93920022A EP0658185A1 (fr) 1992-08-21 1993-08-17 Composition de conditionnement de tissus

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US93407092A 1992-08-21 1992-08-21
US07/934,070 1992-08-21
US8680593A 1993-07-02 1993-07-02
US08/086,805 1993-07-02

Publications (2)

Publication Number Publication Date
WO1994004642A2 true WO1994004642A2 (fr) 1994-03-03
WO1994004642A3 WO1994004642A3 (fr) 1994-03-31

Family

ID=26775166

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1993/007612 Ceased WO1994004642A2 (fr) 1992-08-21 1993-08-17 Composition de conditionnement de tissus

Country Status (2)

Country Link
EP (1) EP0658185A1 (fr)
WO (1) WO1994004642A2 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1840197A1 (fr) * 2006-03-31 2007-10-03 Kao Corporation, S.A. Composition de rinçage et de séchage de véhicules
WO2008121895A1 (fr) * 2007-03-30 2008-10-09 Medivas, Llc Réseaux de polymère élastomère bioabsorbable, agents de réticulation et procédés d'utilisation
WO2009011938A1 (fr) * 2007-07-17 2009-01-22 Medivas, Llc Dispositif de soutien artériel élastomère bioabsorbable et procédés d'utilisation
US8026206B2 (en) 2005-05-18 2011-09-27 Stepan Company Low solids, high viscosity fabric softener compositions and process for making the same
WO2011157490A1 (fr) * 2010-06-17 2011-12-22 Henkel Ag & Co. Kgaa Adoucissant textile épaissi
US9873765B2 (en) 2011-06-23 2018-01-23 Dsm Ip Assets, B.V. Biodegradable polyesteramide copolymers for drug delivery
US9873764B2 (en) 2011-06-23 2018-01-23 Dsm Ip Assets, B.V. Particles comprising polyesteramide copolymers for drug delivery
US10434071B2 (en) 2014-12-18 2019-10-08 Dsm Ip Assets, B.V. Drug delivery system for delivery of acid sensitivity drugs

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060177416A1 (en) 2003-10-14 2006-08-10 Medivas, Llc Polymer particle delivery compositions and methods of use
JP5192384B2 (ja) 2005-09-22 2013-05-08 メディバス エルエルシー ビス−（α−アミノ）−ジオール−ジエステル含有ポリ（エステルアミド）およびポリ（エステルウレタン）組成物および使用の方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1281984A (fr) * 1959-11-25 1962-01-19 Bayer Ag Perfectionnements aux moyens pour empêcher le chargement électrostatique des hauts polymères synthétiques
US4869836A (en) * 1988-05-03 1989-09-26 Colgate-Palmolive Co. Wash cycle fabric conditioning compositions: tertiaryamine-multi-functional carboxylic acid complex
GB8920468D0 (en) * 1989-09-11 1989-10-25 Unilever Plc Fabric softening
DE4111966A1 (de) * 1991-04-12 1992-10-15 Henkel Kgaa Verwendung von estern als textilweichmachender wirkstoff

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8026206B2 (en) 2005-05-18 2011-09-27 Stepan Company Low solids, high viscosity fabric softener compositions and process for making the same
EP1840197A1 (fr) * 2006-03-31 2007-10-03 Kao Corporation, S.A. Composition de rinçage et de séchage de véhicules
WO2008121895A1 (fr) * 2007-03-30 2008-10-09 Medivas, Llc Réseaux de polymère élastomère bioabsorbable, agents de réticulation et procédés d'utilisation
US7649022B2 (en) 2007-03-30 2010-01-19 Medivas, Llc Bioabsorbable elastomeric polymer networks, cross-linkers and methods of use
WO2009011938A1 (fr) * 2007-07-17 2009-01-22 Medivas, Llc Dispositif de soutien artériel élastomère bioabsorbable et procédés d'utilisation
US9090853B2 (en) 2010-06-17 2015-07-28 Henkel Ag & Co. Kgaa Thickened fabric softener comprising free palmitic acid to increase viscosity
WO2011157490A1 (fr) * 2010-06-17 2011-12-22 Henkel Ag & Co. Kgaa Adoucissant textile épaissi
US9873765B2 (en) 2011-06-23 2018-01-23 Dsm Ip Assets, B.V. Biodegradable polyesteramide copolymers for drug delivery
US9873764B2 (en) 2011-06-23 2018-01-23 Dsm Ip Assets, B.V. Particles comprising polyesteramide copolymers for drug delivery
US9896544B2 (en) 2011-06-23 2018-02-20 Dsm Ip Assets, B.V. Biodegradable polyesteramide copolymers for drug delivery
US9963549B2 (en) 2011-06-23 2018-05-08 Dsm Ip Assets, B.V. Biodegradable polyesteramide copolymers for drug delivery
US10434071B2 (en) 2014-12-18 2019-10-08 Dsm Ip Assets, B.V. Drug delivery system for delivery of acid sensitivity drugs
US10888531B2 (en) 2014-12-18 2021-01-12 Dsm Ip Assets B.V. Drug delivery system for delivery of acid sensitivity drugs
US11202762B2 (en) 2014-12-18 2021-12-21 Dsm Ip Assets B.V. Drug delivery system for delivery of acid sensitivity drugs

Also Published As

Publication number Publication date
WO1994004642A3 (fr) 1994-03-31
EP0658185A1 (fr) 1995-06-21

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