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WO2005035631A1 - Amino-functional silicone waxes - Google Patents

Amino-functional silicone waxes Download PDF

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Publication number
WO2005035631A1
WO2005035631A1 PCT/IB2004/003227 IB2004003227W WO2005035631A1 WO 2005035631 A1 WO2005035631 A1 WO 2005035631A1 IB 2004003227 W IB2004003227 W IB 2004003227W WO 2005035631 A1 WO2005035631 A1 WO 2005035631A1
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WO
WIPO (PCT)
Prior art keywords
waxes
formula
silicone waxes
silicone
amino
Prior art date
Application number
PCT/IB2004/003227
Other languages
French (fr)
Inventor
Bernard Danner
Original Assignee
Clariant International Ltd
Clariant Finance (Bvi) Limited
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 Clariant International Ltd, Clariant Finance (Bvi) Limited filed Critical Clariant International Ltd
Priority to US10/575,154 priority Critical patent/US7511165B2/en
Priority to EP04769548A priority patent/EP1678239A1/en
Priority to BRPI0415170-4A priority patent/BRPI0415170A/en
Publication of WO2005035631A1 publication Critical patent/WO2005035631A1/en
Priority to HK07103001A priority patent/HK1095846A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/045—Polysiloxanes containing less than 25 silicon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/28—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen sulfur-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/452—Block-or graft-polymers containing polysiloxane sequences containing nitrogen-containing sequences
    • C08G77/455—Block-or graft-polymers containing polysiloxane sequences containing nitrogen-containing sequences containing polyamide, polyesteramide or polyimide sequences
    • 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 present invention concerns silicone waxes having plural tertiary or quaternary amino groups, their preparation and their use as softeners in the textile industry.
  • the invention accordingly provides amino-functional silicone waxes of the formulae (I) to (IV)
  • R is Cn-C 22 -alkyl, linear or branched
  • R1 is C C 7 -alkyl or benzyl, preferably methyl or benzyl,
  • R2 is -OH, -CH 3> -OCH 3 , -OC 2 H 5 ,
  • a " is CH 3 OSO 3 " , chloride, bromide, iodide or tosylsulfate, preferably CH 3 OSO 3 " or chloride, n is 2 or 3, p is 10-200, preferably 20-50, q+z is 10-400, preferably 15-200, and q/z is 5-50, preferably 10-30.
  • waxes whether in the quaternized form (II) and (IV) or in the non-quaternized form (I) and (III), exhibit good properties when used as softeners. Their great advantage is that they can be used in the form of dispersions which, compared with emulsions, have a higher shearing force stability.
  • the present invention further provides for the preparation of the aforementioned silicone waxes.
  • the initial step is to prepare fatty acid diamides by condensation of fatty acids, for example stearic acid or lauric acid, with diethylenetriamine or dipropylenediamine.
  • the resultant fatty acid diamide is subsequently quaternized with the customary, aforementioned quaternizing agents.
  • the present invention further provides for the use of the aforementioned silicone waxes as softeners in the textile industry.
  • the silicone waxes obtained can be converted by means of dispersants into aqueous dispersions which have a higher shearing force stability than emulsions and are very useful for softening textiles in that the material acquires a pleasant, soft hand.
  • the waxes have the following structure:
  • n 2 or 3
  • R C ⁇ -C ⁇ alkyl radical
  • n 2 or 3
  • R C 11 -C 21 alkyl radical are obtained.
  • the products W E to W 12 -E and also WQ E to WQ 12 -E are very stable to shearing force; they can be applied to textile material (cotton and synthetic fibres) both in the padding process and in the exhaust process.
  • the finished textile materials possess an excellent, soft, pleasant, smooth hand.
  • the finished substrate is added to an aqueous liquor which, based on the substrate, contains 0.5% to 4.0% of the end products described in the examples, at about 40°C and a liquor ratio of 6:1 to 20:1 , in a laboratory jet. After 20 minutes at pH 5.0 to 6.0 (40°C) and continuous agitation of the substrate, the substrate is removed from the liquor, whizzed and dried tensionlessly at 140°C for 70-90 seconds.
  • the finished substrate is padded at room temperature, to a 100% dry weight increase, with an aqueous liquor which contains 15 to 60 g/l of the end products W-E or WQ-E.
  • the padded material is subsequently dried at 140°C for 70-90 seconds.
  • Substrate Exhaust process: Tricot fabric, dyed, with or without setting - 100% cotton - polyester (50%) / cotton (50%)
  • Padding process Tricot or woven fabric, dyed, with or without setting - 100% cotton - polyester (50%) / cotton (50%) - polyester (100%) - polyacrylonitrile (100%) - nylon 6 (100%)
  • Softness can be tested pairwise or using a handle-O-meter (for example a 211-5 Twing Albert).
  • the finished samples are first conditioned (24 hours, 20°C, 65% relative humidity) before being assessed.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Silicon Polymers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

The present invention relates to silicone waxes having plural tertiary or quaternary amino groups, their preparation and their use as softeners in the textile industry. These waxes can be processed into stable aqueous dispersions and lead to products having a pleasant, soft hand.

Description

AMINO-FUNCTIONAL SILICONE WAXES
The present invention concerns silicone waxes having plural tertiary or quaternary amino groups, their preparation and their use as softeners in the textile industry.
There is extensive literature on amino-functional silicone compounds. These compounds are used for example as plasticizers in the textile industry, as surface- treating agents, as thickeners or in the cosmetic industry. Nonetheless, there is a demand in the textile industry for softening substances which lead to products having a superior hand and which do not have the disadvantage of unstable emulsions in use.
It has now been found that certain silicone waxes having plural tertiary or quaternary nitrogen atoms can be processed into stable aqueous dispersions and have surprisingly good properties when used as softeners in the textile industry and lead to products having a pleasant, soft hand.
The invention accordingly provides amino-functional silicone waxes of the formulae (I) to (IV)
Figure imgf000002_0001
Figure imgf000003_0001
Figure imgf000003_0002
where
R is Cn-C22-alkyl, linear or branched,
R1 is C C7-alkyl or benzyl, preferably methyl or benzyl,
R2 is -OH, -CH3> -OCH3, -OC2H5,
A" is CH3OSO3 ", chloride, bromide, iodide or tosylsulfate, preferably CH3OSO3 " or chloride, n is 2 or 3, p is 10-200, preferably 20-50, q+z is 10-400, preferably 15-200, and q/z is 5-50, preferably 10-30.
These waxes, whether in the quaternized form (II) and (IV) or in the non-quaternized form (I) and (III), exhibit good properties when used as softeners. Their great advantage is that they can be used in the form of dispersions which, compared with emulsions, have a higher shearing force stability.
The present invention further provides for the preparation of the aforementioned silicone waxes. The initial step is to prepare fatty acid diamides by condensation of fatty acids, for example stearic acid or lauric acid, with diethylenetriamine or dipropylenediamine.
The resultant fatty acid diamide is reacted with silicone oils of the general formula (V)
Figure imgf000004_0001
where p has the same meaning as in formula (I) or (II), to prepare the waxes of formula (I) or (II),
or subsequently quaternized with the customary quaternizing agents such as methyl sulfate, ethyl sulfate, methyl halide, benzyl chloride or tosyl sulfate to prepare the waxes of the formula (II). The starting materials and their preparation will be known to one skilled in the art.
To prepare the waxes of the formula (III) or (IV), the resultant fatty acid diamide is reacted with silicone oils of the general formula (VI)
Figure imgf000004_0002
where R2, (q+z) and q/z have the same meaning as in formula (III) or (IV),
and to prepare the waxes of the formula (IV), the resultant fatty acid diamide is subsequently quaternized with the customary, aforementioned quaternizing agents.
The present invention further provides for the use of the aforementioned silicone waxes as softeners in the textile industry. The silicone waxes obtained can be converted by means of dispersants into aqueous dispersions which have a higher shearing force stability than emulsions and are very useful for softening textiles in that the material acquires a pleasant, soft hand.
EXAMPLES 1. Preparation of fatty acid diamides (Fatty acid: RCOOH)
1.1 Preparation of R-CONH(CH2)2NH(CH2)2NHCO-R 2 mol of fatty acid are heated to 105°C under nitrogen; 1 mol of diethylenetri- amine is then added dropwise while at the same time the temperature is raised to 130°C. This is followed by 24 hours of condensation at 130°C under a slow stream of nitrogen using a distillation bridge. The reaction mixture is subsequently discharged. The acid number of the reaction mixture (number of mg of KOH to neutralize 1 g of product) is less than 7. The resultant amount of condensation product requires less than 1.1 mol of perchloric acid to titrate the free amino groups.
1.2 Preparation of R-CONH(CH2)3NH(CH2)3NHCO-R 1.1 is repeated using dipropylenediamine instead of diethylenediamine.
Figure imgf000006_0002
2. Preparation of silicone waxes 2.1 Silicone waxes W. - W6 661.5 parts of the silicone oil of the formula
Figure imgf000006_0001
are reacted at 150°C under nitrogen for 14 hours with x parts of the diamides D-i to D6. A check is subsequently carried out to see that glycidyl groups are no longer present. The following waxes are obtained:
Figure imgf000006_0003
The waxes have the following structure:
Figure imgf000007_0001
2.2 Silicone waxes W7 - W12 661.5 parts of the silicone oil of the formula
Figure imgf000007_0002
are reacted at 150°C under nitrogen for 14 hours with x parts of the diamides D^ to D6. A check is subsequently carried out to see that glycidyl groups have reacted quantitatively. The following waxes are obtained:
Figure imgf000007_0003
The waxes have the following structure:
Figure imgf000008_0001
n = 2 or 3, R = C^-C^ alkyl radical
Preparation of quaternized silicone waxes WQi - WQ 2 x parts of silicone wax W are melted and allowed to react with 25.2 parts of dimethyl sulfate for 2 hours at about 70-75°C.
Figure imgf000008_0002
Waxes having the structures:
Figure imgf000009_0001
and
Figure imgf000009_0002
n = 2 or 3, R = C11-C21 alkyl radical are obtained.
4. Preparation of end products 4.1 Based on silicone waxes \N^ - W12 125.0 parts of silicone wax (W) are melted. 25.0 parts of a 70% solution of
CH, C17H35CONH(CH2)3— N-CH3 ? CH3OS03 Θ CH,
(dispersant 1 ) in propylene glycol and also 37.5 parts of stearyl poly-10-glycol ether (dispersant 2) are then added. As soon as there is a homogeneous melt, 800.0 parts of water are added in increments with stirring. Finally, 12.5 parts of glacial acetic acid are added. This gives 1000.0 parts of a 12.5% silicone wax dispersion (W-E). 4.2 Based on quaternary silicone waxes WQi - WQ12 4.1 is repeated except that the silicone waxes (WQ) are used instead of the silicone waxes (W) and 12.5 parts of water are added at the end instead of 12.5 parts of glacial acetic acid. This gives 1000.0 parts of a 12.5% silicone wax dispersion (WQ-E).
The products W E to W12-E and also WQ E to WQ12-E are very stable to shearing force; they can be applied to textile material (cotton and synthetic fibres) both in the padding process and in the exhaust process. The finished textile materials possess an excellent, soft, pleasant, smooth hand.
APPLICATION EXAMPLES The following finishing operations were carried out:
• Exhaust process The finished substrate is added to an aqueous liquor which, based on the substrate, contains 0.5% to 4.0% of the end products described in the examples, at about 40°C and a liquor ratio of 6:1 to 20:1 , in a laboratory jet. After 20 minutes at pH 5.0 to 6.0 (40°C) and continuous agitation of the substrate, the substrate is removed from the liquor, whizzed and dried tensionlessly at 140°C for 70-90 seconds.
• Padding process The finished substrate is padded at room temperature, to a 100% dry weight increase, with an aqueous liquor which contains 15 to 60 g/l of the end products W-E or WQ-E. The padded material is subsequently dried at 140°C for 70-90 seconds.
Substrate: Exhaust process: Tricot fabric, dyed, with or without setting - 100% cotton - polyester (50%) / cotton (50%) Padding process: Tricot or woven fabric, dyed, with or without setting - 100% cotton - polyester (50%) / cotton (50%) - polyester (100%) - polyacrylonitrile (100%) - nylon 6 (100%)
Testing: Softness can be tested pairwise or using a handle-O-meter (for example a 211-5 Twing Albert). The finished samples are first conditioned (24 hours, 20°C, 65% relative humidity) before being assessed.
All the finishes show a distinct improvement in softness compared with unfinished fabric.

Claims

1. Amino-functional silicone waxes of the formulae (I) to (IV)
Figure imgf000012_0001
Figure imgf000012_0002
Figure imgf000012_0003
where
R is Cn-C22-alkyl, linear or branched,
R1 is CτC7-alkyl or benzyl,
R2 is -OH, -CH3> -OCH3> -OC2H5,
A" is CH3OSO3 ", chloride, bromide, iodide or tosylsulfate, n is 2 or 3, p is 10-200, q+z is 10-400, and q/z is 5-50.
Amino-functional silicone waxes according to Claim 1 wherein
R, R2 and n are each as defined above,
R1 is methyl or benzyl,
A" is CH3OSO3 " or chloride, p is 20-50, q+z is 15-200, and q/z is 10-30.
Process for preparating amino-functional silicone waxes of the formulae (I) or (III) according to Claim 1, characterized in that fatty acid diamides are prepared by condensation of fatty acids with diethylenetriamine or dipropylenediamine and then reacted with silicone oils of the general formula (V)
Figure imgf000013_0001
where p has the same meaning as in formula (I) or (II), to prepare the waxes of the formula (I)
or with silicone oils of the formula (VI) 13
Figure imgf000014_0001
where R2, (q+z) and q/z have the same meaning as in formula (III) or (IV), to prepare the waxes of the formula (III).
Process according to Claim 3, characterized in that the resultant silicone waxes of the formula (I) or (III) are quaternized to the compounds of the formulae (II) or (IV).
Process according to Claim 3 or 4, characterized in that the fatty acids are stearic acid, behenic acid or lauric acid.
6. Use of the silicone waxes according to Claims 1 or 2 as softeners in the textile industry.
7. Use according to Claim 7, characterized in that the silicone waxes are used in the form of aqueous dispersions.
PCT/IB2004/003227 2003-10-07 2004-10-04 Amino-functional silicone waxes WO2005035631A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US10/575,154 US7511165B2 (en) 2004-10-04 2004-10-04 Amino-functional silicone waxes
EP04769548A EP1678239A1 (en) 2003-10-07 2004-10-04 Amino-functional silicone waxes
BRPI0415170-4A BRPI0415170A (en) 2003-10-07 2004-10-04 amino-functional silicone waxes
HK07103001A HK1095846A1 (en) 2003-10-07 2007-03-20 Amino-functional silicone waxes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP03022447.1 2003-10-07
EP03022447 2003-10-07

Publications (1)

Publication Number Publication Date
WO2005035631A1 true WO2005035631A1 (en) 2005-04-21

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EP (1) EP1678239A1 (en)
CN (1) CN100384913C (en)
BR (1) BRPI0415170A (en)
HK (1) HK1095846A1 (en)
WO (1) WO2005035631A1 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009280813A (en) * 2008-05-19 2009-12-03 Wacker Chemie Ag Method of producing oragno-polysiloxane with quaternary ammonium group
EP2689804A3 (en) * 2012-07-27 2015-05-06 Henkel AG&Co. KGAA Protective hair dye with silicone(s) and polymer(s)
US9352289B2 (en) 2010-12-28 2016-05-31 Conopco, Inc. Method for production of an emulsion

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6633551B2 (en) * 2014-06-12 2020-01-22 ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー Wax and urethane based extender blends for surface effect compositions

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0415698A2 (en) * 1989-08-31 1991-03-06 Unilever Plc Fabric softening composition
EP0738511A1 (en) * 1995-04-18 1996-10-23 Rhone-Poulenc Chimie Use of silicone waxes containing ester functions as thickeners in oily media
US6165444A (en) * 1995-09-29 2000-12-26 L'oreal Composition for treating keratinous material, including at least one silicone-grafted polymer and at least one fatty-chain amide, and uses thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2749505B1 (en) * 1996-06-07 1998-07-10 Oreal ALKYLPOLYSILOXANE NON-TRANSFER MAKEUP OR CARE COMPOSITION

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0415698A2 (en) * 1989-08-31 1991-03-06 Unilever Plc Fabric softening composition
EP0738511A1 (en) * 1995-04-18 1996-10-23 Rhone-Poulenc Chimie Use of silicone waxes containing ester functions as thickeners in oily media
US6165444A (en) * 1995-09-29 2000-12-26 L'oreal Composition for treating keratinous material, including at least one silicone-grafted polymer and at least one fatty-chain amide, and uses thereof

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009280813A (en) * 2008-05-19 2009-12-03 Wacker Chemie Ag Method of producing oragno-polysiloxane with quaternary ammonium group
US9352289B2 (en) 2010-12-28 2016-05-31 Conopco, Inc. Method for production of an emulsion
EP2689804A3 (en) * 2012-07-27 2015-05-06 Henkel AG&Co. KGAA Protective hair dye with silicone(s) and polymer(s)

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BRPI0415170A (en) 2006-11-28
CN1863844A (en) 2006-11-15
CN100384913C (en) 2008-04-30
EP1678239A1 (en) 2006-07-12
HK1095846A1 (en) 2007-05-18

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