EP1678239A1 - Aminofunktionelle silikonwachse - Google Patents

Aminofunktionelle silikonwachse

Info

Publication number
EP1678239A1
EP1678239A1 EP04769548A EP04769548A EP1678239A1 EP 1678239 A1 EP1678239 A1 EP 1678239A1 EP 04769548 A EP04769548 A EP 04769548A EP 04769548 A EP04769548 A EP 04769548A EP 1678239 A1 EP1678239 A1 EP 1678239A1
Authority
EP
European Patent Office
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.)
Withdrawn
Application number
EP04769548A
Other languages
English (en)
French (fr)
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 Finance BVI Ltd
Original Assignee
Clariant International 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 filed Critical Clariant International Ltd
Priority to EP04769548A priority Critical patent/EP1678239A1/de
Publication of EP1678239A1 publication Critical patent/EP1678239A1/de
Withdrawn legal-status Critical Current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)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Silicon Polymers (AREA)
EP04769548A 2003-10-07 2004-10-04 Aminofunktionelle silikonwachse Withdrawn EP1678239A1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP04769548A EP1678239A1 (de) 2003-10-07 2004-10-04 Aminofunktionelle silikonwachse

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP03022447 2003-10-07
PCT/IB2004/003227 WO2005035631A1 (en) 2003-10-07 2004-10-04 Amino-functional silicone waxes
EP04769548A EP1678239A1 (de) 2003-10-07 2004-10-04 Aminofunktionelle silikonwachse

Publications (1)

Publication Number Publication Date
EP1678239A1 true EP1678239A1 (de) 2006-07-12

Family

ID=34429232

Family Applications (1)

Application Number Title Priority Date Filing Date
EP04769548A Withdrawn EP1678239A1 (de) 2003-10-07 2004-10-04 Aminofunktionelle silikonwachse

Country Status (5)

Country Link
EP (1) EP1678239A1 (de)
CN (1) CN100384913C (de)
BR (1) BRPI0415170A (de)
HK (1) HK1095846A1 (de)
WO (1) WO2005035631A1 (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102008001867A1 (de) * 2008-05-19 2009-11-26 Wacker Chemie Ag Verfahren zur Herstellung von quartäre Ammoniumgruppen aufweisenden Organopolysiloxanen
EA024947B1 (ru) 2010-12-28 2016-11-30 Юнилевер Нв Способ получения эмульсии
DE102012213248A1 (de) * 2012-07-27 2014-01-30 Henkel Ag & Co. Kgaa Pflegende Haarfärbemittel mit Silicon(en) und Polymer(en)
EP3155164B1 (de) * 2014-06-12 2021-03-17 The Chemours Company FC, LLC Auf wachs und urethan-streckmittel basierende mischungen für oberflächeneffektzusammensetzungen

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8919669D0 (en) * 1989-08-31 1989-10-11 Unilever Plc Fabric-softening compositions
FR2733245B1 (fr) * 1995-04-18 1997-05-23 Rhone Poulenc Chimie Utilisation de cires silicones a fonctions esters pour epaissir des milieux huileux
FR2739284B1 (fr) * 1995-09-29 1997-11-07 Oreal Composition pour le traitement des matieres keratiniques comprenant au moins un polymere silicone greffe et au moins un amide a chaine grasse et utilisations
FR2749505B1 (fr) * 1996-06-07 1998-07-10 Oreal Composition de maquillage ou de soin sans transfert a alkylpolysiloxane

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2005035631A1 *

Also Published As

Publication number Publication date
HK1095846A1 (en) 2007-05-18
BRPI0415170A (pt) 2006-11-28
CN100384913C (zh) 2008-04-30
CN1863844A (zh) 2006-11-15
WO2005035631A1 (en) 2005-04-21

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