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WO2005035631A1 - Cires siliconees aminees - Google Patents

Cires siliconees aminees 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
Authority
WO
WIPO (PCT)
Prior art keywords
waxes
formula
silicone waxes
silicone
amino
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/IB2004/003227
Other languages
English (en)
Inventor
Bernard Danner
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.)
Clariant International Ltd
Clariant Finance BVI Ltd
Original Assignee
Clariant International Ltd
Clariant Finance BVI Ltd
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 Ltd filed Critical Clariant International Ltd
Priority to US10/575,154 priority Critical patent/US7511165B2/en
Priority to BRPI0415170-4A priority patent/BRPI0415170A/pt
Priority to EP04769548A priority patent/EP1678239A1/fr
Priority to HK07103001.4A priority patent/HK1095846B/xx
Publication of WO2005035631A1 publication Critical patent/WO2005035631A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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.

Landscapes

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

Abstract

L'invention concerne des cires siliconées portant plusieurs groupements amine tertiaire ou quaternaire, leur préparation et leur utilisation comme assouplissants dans l'industrie textile. Ces cires peuvent être transformées en dispersions aqueuses stables et donner des produits ayant un toucher doux et agréable.
PCT/IB2004/003227 2003-10-07 2004-10-04 Cires siliconees aminees Ceased WO2005035631A1 (fr)

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
BRPI0415170-4A BRPI0415170A (pt) 2003-10-07 2004-10-04 ceras de silicone amino-funcionais
EP04769548A EP1678239A1 (fr) 2003-10-07 2004-10-04 Cires de silicone aminofonctionnels
HK07103001.4A HK1095846B (en) 2003-10-07 2004-10-04 Amino-functional silicone waxes

Applications Claiming Priority (2)

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

Publications (1)

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

Family

ID=34429232

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2004/003227 Ceased WO2005035631A1 (fr) 2003-10-07 2004-10-04 Cires siliconees aminees

Country Status (4)

Country Link
EP (1) EP1678239A1 (fr)
CN (1) CN100384913C (fr)
BR (1) BRPI0415170A (fr)
WO (1) WO2005035631A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009280813A (ja) * 2008-05-19 2009-12-03 Wacker Chemie Ag 第４級アンモニウム基を有するオルガノポリシロキサンの製造方法
EP2689804A3 (fr) * 2012-07-27 2015-05-06 Henkel AG&Co. KGAA Produit de teinture et de soin des cheveux avec des silicone(s) et des polymère(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
WO2015191326A1 (fr) * 2014-06-12 2015-12-17 The Chemours Company Fc, Llc Mélanges de cire et de matière de charge à base d'uréthane pour des compositions à effet de surface

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0415698A2 (fr) * 1989-08-31 1991-03-06 Unilever Plc Composition adoucissante pour textile
EP0738511A1 (fr) * 1995-04-18 1996-10-23 Rhone-Poulenc Chimie Utilisation de cires silicones à fonctions esters pour épaissir des milieux huileux
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 (fr) * 1996-06-07 1998-07-10 Oreal Composition de maquillage ou de soin sans transfert a alkylpolysiloxane

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0415698A2 (fr) * 1989-08-31 1991-03-06 Unilever Plc Composition adoucissante pour textile
EP0738511A1 (fr) * 1995-04-18 1996-10-23 Rhone-Poulenc Chimie Utilisation de cires silicones à fonctions esters pour épaissir des milieux huileux
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 (ja) * 2008-05-19 2009-12-03 Wacker Chemie Ag 第４級アンモニウム基を有するオルガノポリシロキサンの製造方法
US9352289B2 (en) 2010-12-28 2016-05-31 Conopco, Inc. Method for production of an emulsion
EP2689804A3 (fr) * 2012-07-27 2015-05-06 Henkel AG&Co. KGAA Produit de teinture et de soin des cheveux avec des silicone(s) et des polymère(s)

Also Published As

Publication number Publication date
CN100384913C (zh) 2008-04-30
HK1095846A1 (zh) 2007-05-18
CN1863844A (zh) 2006-11-15
EP1678239A1 (fr) 2006-07-12
BRPI0415170A (pt) 2006-11-28

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