CA2329959A1 - Stable quaternary ammonium compositions - Google Patents

Stable quaternary ammonium compositions Download PDF

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Publication number
CA2329959A1
CA2329959A1 CA002329959A CA2329959A CA2329959A1 CA 2329959 A1 CA2329959 A1 CA 2329959A1 CA 002329959 A CA002329959 A CA 002329959A CA 2329959 A CA2329959 A CA 2329959A CA 2329959 A1 CA2329959 A1 CA 2329959A1
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CA
Canada
Prior art keywords
quaternary ammonium
ammonium material
stabilising agent
weight
alkyl
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
Application number
CA002329959A
Other languages
French (fr)
Other versions
CA2329959C (en
Inventor
David William Thornthwaite
Christopher Whaley
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.)
Sun Products Corp
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2329959A1 publication Critical patent/CA2329959A1/en
Application granted granted Critical
Publication of CA2329959C publication Critical patent/CA2329959C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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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
    • C11D3/26Organic compounds containing nitrogen
    • C11D3/30Amines; Substituted amines ; Quaternized amines
    • 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
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2003Alcohols; Phenols
    • C11D3/2065Polyhydric alcohols
    • 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
    • C11D3/26Organic compounds containing nitrogen
    • C11D3/32Amides; Substituted amides
    • C11D3/323Amides; Substituted amides urea or derivatives thereof

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Detergent Compositions (AREA)

Abstract

The invention provides stable compositions comprising ester-containing quaternary ammonium material and one or more stabilising agent(s) chosen from: a) urea, b) urea derivatives, c) organic compounds with at least one free lone pair of electrons chosen from: i) primary amines, ii) secondary amines, and/or iii) tertiary amines, iv) glycerol wherein the composition is a liquid, molten or semi-solid containing % or less water, and when glycerol is used the ammonium material has 2 or less CH3 groups attached to the quaternary nitrogen atom.

Claims (10)

1. Stable compositions comprising quaternary ammonium material materials containing at least one ester group characterised in that they further comprise one or more stabilising agent(s) chosen from;
a) urea b) urea derivatives c) one or more organic compounds having at least one free lone pair of electrons chosen from;
i) primary amines RNH2, where R is a C3-17 alkyl, alkenyl, hydroxyalkyl or substituted derivative thereof, ii) secondary amines, and/or iii) tertiary amines NR1R2R3 wherein R1R2R3 are independently C1-C22 alkyl, alkenyl or hydroxyalkyl groups or substituted derivatives thereof, and wherein when both R1 and R2 are -CH2CH2OH or both R1 and R2 are -CH2CH2OCOR4, R4CO is C16-18, then R3 is not a methyl group with the proviso that the composition is in a liquid, molten or semi-solid form containing 10% or less water, and wherein the stabilising agent is present at levels of 0.05 to 10% by weight of the weight of the quaternary ammonium material, preferably 0.5 to 8.5%, even more preferably 0.75 to 5%.
2. A composition according to claim 1 wherein the stabilising agent is urea or a tertiary amine wherein R1 and R2 are C1-C2 alkyl groups and R3 is a C2 - C4 hydroxyalkyl, preferably N-N-dimethyl ethanolamine.
3. A composition according to any one of the preceding claims wherein the quaternary ammonium material is of formula where each R1 group is independently selected from C1-4 alkyl, hydroxyalkyl or C2-4 alkenyl groups; and each R2 group is independently selected from C8-28 alkyl or alkenyl groups; X is any suitable counterion,~~

T is and n is an integer from 1-5 or is 0.
4. A composition according to claim 3 wherein where each R1 group is methyl, each R2 group is tallow, X- is chloride and n is 2.
5. A process of stabilising quaternary ammonium material containing at least one ester group via the steps of adding at least one stabilising agent of claim 1 to the quaternary ammonium material wherein the stabilising agent is present at levels of 0.05 to 10% by weight of the weight of the quaternary ammonium material, preferably 0.5 to 8.5%, even more preferably 0.75 to 5%.
6. Process according to claim 5 wherein addition of the stabilising agent occurs during the manufacture of the quaternary ammonium material, preferably following the quaternisation step in the synthesis of the quaternary ammonium material.
7. Process according to either claim 5 or claim 6 wherein addition of the stabilising agent occurs after manufacture of the quaternary ammonium material, preferably during storage thereof.
8, A solid rinse conditioner comprising a composition as defined in cry of claims 1-4, preferably in granular or powdered form.
9. A liquid rinse conditioner made by dilution of a composition as defined in any of claims 1-4, with water.
10. Method of reducing the alkyl halide levels in quaternary ammonium material containing at least one ester group over time by the addition of a stabilising agent as defined in claim 1 wherein the stabilising agent is present at levels of 0.05 to 10% by weight of the weight of the quaternary ammonium material, preferably 0.5 to 8.5%, even more preferably 0.75 to 5%.
CA2329959A 1998-05-18 1999-05-12 Stable quaternary ammonium compositions Expired - Fee Related CA2329959C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB9810656.0 1998-05-18
GBGB9810656.0A GB9810656D0 (en) 1998-05-18 1998-05-18 Stable ammonium compositions
PCT/EP1999/003367 WO1999060082A1 (en) 1998-05-18 1999-05-12 Stable quaternary ammonium compositions

Publications (2)

Publication Number Publication Date
CA2329959A1 true CA2329959A1 (en) 1999-11-25
CA2329959C CA2329959C (en) 2010-04-27

Family

ID=10832261

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2329959A Expired - Fee Related CA2329959C (en) 1998-05-18 1999-05-12 Stable quaternary ammonium compositions

Country Status (12)

Country Link
EP (1) EP1080172B1 (en)
CN (1) CN1280389C (en)
AR (1) AR019556A1 (en)
AU (1) AU4604599A (en)
BR (1) BR9910550B1 (en)
CA (1) CA2329959C (en)
DE (1) DE69925119T2 (en)
ES (1) ES2241289T3 (en)
GB (1) GB9810656D0 (en)
HU (1) HUP0101902A3 (en)
TR (1) TR200003385T2 (en)
WO (1) WO1999060082A1 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2003236327A1 (en) * 2002-04-08 2003-10-20 Kao Corporation Cosmetic hair preparation
EP1584674B1 (en) * 2004-03-29 2007-08-15 Clariant Produkte (Deutschland) GmbH Easy-dispersible concentrate ester quat compositions
US20090312428A1 (en) 2008-06-13 2009-12-17 Fernando Figueredo Biocide Compositions Comprising Quaternary Ammonium and Urea and Methods for Their Use
US8257720B2 (en) 2009-04-20 2012-09-04 Conopco, Inc. Stabilized cationic ammonium compounds and compositions comprising the same
US8324255B2 (en) * 2009-09-15 2012-12-04 Conopco, Inc. Chelator stabilized cationic ammonium compounds and compositions comprising the same

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2454465A1 (en) * 1974-11-16 1976-05-20 Hoechst Ag Powdery germ inhibiting soft rinsing compsns for textiles - contg cationic soft rinse, cationic disinfectant, urea and non ionic dispersant
EP0258923B1 (en) * 1986-09-02 1993-10-06 Akzo Nobel N.V. Fabric softening composition and detergent-composition comprising the same
GB8805837D0 (en) * 1988-03-11 1988-04-13 Unilever Plc Fabric conditioning composition
US5282983A (en) * 1990-08-22 1994-02-01 Kao Corporation Fabric softener composition and ammonium salt
US5259964A (en) * 1991-12-18 1993-11-09 Colgate-Palmolive Co. Free-flowing powder fabric softening composition and process for its manufacture
US5543067A (en) * 1992-10-27 1996-08-06 The Procter & Gamble Company Waterless self-emulsiviable biodegradable chemical softening composition useful in fibrous cellulosic materials
DE4307186A1 (en) * 1993-03-08 1994-09-15 Henkel Kgaa Aqueous fabric softener composition
DE19629666A1 (en) * 1996-07-23 1998-01-29 Henkel Kgaa Process for the hydrophilic finishing of fibers or nonwovens

Also Published As

Publication number Publication date
EP1080172B1 (en) 2005-05-04
HUP0101902A2 (en) 2001-10-28
CN1280389C (en) 2006-10-18
AR019556A1 (en) 2002-02-27
ES2241289T3 (en) 2005-10-16
TR200003385T2 (en) 2001-02-21
BR9910550A (en) 2001-01-30
DE69925119D1 (en) 2005-06-09
HUP0101902A3 (en) 2002-08-28
AU4604599A (en) 1999-12-06
GB9810656D0 (en) 1998-07-15
BR9910550B1 (en) 2009-05-05
CA2329959C (en) 2010-04-27
EP1080172A1 (en) 2001-03-07
CN1301292A (en) 2001-06-27
DE69925119T2 (en) 2005-10-06
WO1999060082A1 (en) 1999-11-25

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Effective date: 20190513