WO2009080441A1 - Prépoly(siloxane-uréthane) réactif et émulsion de poly(siloxane-uréthane) réactif sans solvant préparée à partir de celui-ci - Google Patents

Prépoly(siloxane-uréthane) réactif et émulsion de poly(siloxane-uréthane) réactif sans solvant préparée à partir de celui-ci Download PDF

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Publication number
WO2009080441A1
WO2009080441A1 PCT/EP2008/066351 EP2008066351W WO2009080441A1 WO 2009080441 A1 WO2009080441 A1 WO 2009080441A1 EP 2008066351 W EP2008066351 W EP 2008066351W WO 2009080441 A1 WO2009080441 A1 WO 2009080441A1
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WO
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Prior art keywords
siloxane
urethane
prepoly
reactive
minutes
Prior art date
Application number
PCT/EP2008/066351
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English (en)
Inventor
Kan Chengyou
Hou Zhao Sheng
Li Zeping
Xie Wei
Zhao Zhiqing
Yon Zhang
Thomas Fay-Oy Lim
Original Assignee
Henkel Ag & Co. Kgaa
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
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Application filed by Henkel Ag & Co. Kgaa filed Critical Henkel Ag & Co. Kgaa
Publication of WO2009080441A1 publication Critical patent/WO2009080441A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C14—SKINS; HIDES; PELTS; LEATHER
    • C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
    • C14C11/00—Surface finishing of leather
    • C14C11/003—Surface finishing of leather using macromolecular compounds
    • C14C11/006—Surface finishing of leather using macromolecular compounds using polymeric products of isocyanates (or isothiocyanates) with compounds having active hydrogen
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
    • C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
    • C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4833—Polyethers containing oxyethylene units
    • C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/6692—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/34
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/08—Polyurethanes from polyethers
    • 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
    • D06M15/653—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain modified by isocyanate compounds
    • 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
    • C08G2190/00—Compositions for sealing or packing joints

Definitions

  • the present invention is related to the field of material sience, more particularly, the present invention is related to a reactive prepoly(siloxane-urethane) and a process for preparing the same as well as a solvent-free reactive poly(siloxane-urethane) emulsion obtained by dispersing said prepoly(siloxane-urethane), and a process for preparing said emulsion.
  • WPU waterborne polyurethane
  • Incorporating a reactive organosilicon compound into WPU may render the material with the properties of both the organosilicon and the polyurethane.
  • Organosilicon-modified WPU products generally take shorter time to form a film, have long life and excellent properties such as binder, strength, tenacity, wear resistance as well as water resistance and solvent resistance.
  • the amounts of the reactive organosilicon components in these reactive poly(siloxane-urethane) emulsions are generally lower and may be only of 2-5wt% based on the solid content of the dispersions, but the amount of the reactive organosilicon is in intimate relation to the properties of the latex film.
  • the present invention provides a reactive prepoly- (siloxane-urethane) and a process for preparing the same.
  • the present invention further provides a solvent-free reactive poly(siloxane-urethane) emulsion obtained by dispersing said reactive prepoly(siloxane-urethane) and a process for preparing said emulsion.
  • the inventive reactive prepoly(siloxane-urethane) is prepared by bulk polymerization technology.
  • the amount of the reactive organosilicon in the reactive prepoly(siloxane-urethane) can be up to 15wt%, thus being improved greatly over the prior art.
  • the inventive solvent-free reactive poly(siloxane-urethane) emulsion is prepared by phase inversion emulsification technology with simple procedure, easy operation and low production cost.
  • said solvent-free reactive poly- (siloxane-urethane) emulsion does not comprise any organic solvent, thus favoring to the environmental protection.
  • the solid content of this emulsion can be up to 55wt%, and the latex particle size can be of about 200nm, thus being improved significantly over the prior art.
  • This emulsion has excellent storage stability and freeze-thaw stability. Specifically, this emulsion can be stored stably at ambient temperature over 180 days, and can be stored stably at 50 0 C over 150 days.
  • inventive solvent-free reactive poly(siloxane-urethane) emulsion not only can be directly used in the fields such as leather processing, paper making and texile finishing etc, but also can be widely used in the production of environmental friendly aqueous sealing agents and aqueous coatings.
  • the inventive solvent-free reactive poly(siloxane-urethane) emulsion can have a minium film-forming temperature of below 0 0 C and can crosslink quickly to form a film at ambient temperature with the evaporation of moisture at a crosslinkage degree of about 90wt%.
  • the film-forming rate is much higher than that of a usual aqueous polyurethane emulsion; and the obtained latex film has excellent mechanical properties such as excellent adhesion, flexibility and impact strength etc.
  • the present invention provides a reactive prepoly- (siloxane-urethane), wherein the prepoly(siloxane-urethane) has a weight average molecular weight from 3000 to 200000, preferably from 5000 to 100000, most preferably from 8000 to 50000, and has the following schematic formula:
  • n is 0 or 1
  • m is an integer from 5 to 1000
  • R 1 , R 2 each independently are methyl or ethyl
  • R 3 is methylene or is H or
  • R 5 is -(CH 2 J 6 -, H or , R 6 is methyl or H, provided that not all R 6 are H, R 7 is methyl, ethyl, propyl, butyl or benzyl, and R 8 is methyl and/or ethyl.
  • the amount of reactive organosilicon may be up to 15wt%, preferably 9-12.5wt%.
  • the present invention further provides a process for preparing the reactive prepoly(siloxane-urethane) using bulk polymerization technology, comprising the following steps: a. mixing diisocyanate, polyether and hydrophilic monomer, then heating the mixture with sufficient stirring to get molten; b. polymerizing sufficiently the molten mixture from step a by adding catalyst thereinto; c. continuing the reaction with stirring for some time by adding tertiary amine into the reaction mixture from step b; and d. continuing the reaction at the temperature for some time by adding reactive organosilicon monomer into the reaction mixture from step c, and finally obtaining the reactive prepoly(siloxane-urethane).
  • the diisocyanate is selected from the group consisting of toluene- 2,4-diisocyanate (TDI), biphenyl methane-2,4'-diisocyanate (MDI), 1 ,6-hexa- methylene diisocyanate (HDI), isophorone diisocyanate (IPDI) and mixtures thereof;
  • the polyether is selected from the group consisting of polyethylene oxide (PEO), polypropylene oxide (PPO), copolymer of ethylene oxide and propylene oxide (PEO-co-PPO) and mixture of polyethylene oxide and polypropylene oxide, and the molecular weight of the polyether is controlled as from 200 to 40000, preferably from 200 to 20000, most preferably from 300 to 10000; and the hydrophilic monomer is selected from the group consisting of 2,2-dimethylol propionic acid (TDI), biphenyl methane-2,4'-diisocyanate (MDI), 1 ,6-hex
  • the catalyst to be used is an organic tin compound selected from the group consisting of dibutyltin dilaurate (DBTDL) and stannous octoate (SO) and/or a tertiary amine compound selected from the group consisting of triethyl amine and trimethyl amine, preferably the organic tin compound;
  • the catalyst is used in an amount of 0.01 -5wt%, preferably 0.01 -3wt%, most preferably 0.05-1 .5wt%, based on the total weight of all monomers; and after the addition of the catalyst, the molten mixture is polymerized, preferably polymerized at the given temperature, for a time from 0.5 to 24 hours, preferably from 0.5 to 12 hours, most preferably from 1 .5 to 4 hours.
  • the tertiary amine to be added is selected from the group consisting of trimethyl amine, triethyl amine, tripropyl amine, tributyl amine and benzyl-containing tertiary amine, preferably trimethyl amine and triethyl amine, most preferably triethyl amine; preferably the tertiary amine is added dropwise, and the molar ratio between the tertiary amine and the hydrophilic monomer is from 0.8:1 to 3:1 , preferably from 1 :1 to 2:1 , most preferably from 1 :1 to 1 .5:1 ; and after the addition of the tertiary amine, the reaction is continued with stirring for a time from 5 minutes to 10 hours, preferably from 10 minutes to 3 hours, most preferably from 15 mimutes to 1 .5 hours.
  • the reactive organosilicon monomer to be added is selected from the group consisting of ⁇ -aminopropyl triethoxy silane (APTES), ⁇ -aminopropyl methyldiethoxy silane (APMDES), ⁇ -aminopropyl trimethoxy silane (APTMS), ⁇ -aminopropyl methyldimethoxy silane (APMDMS), anilinomethyl triethoxy silane (PAMTES), anilinomethyl methyl diethoxy silane (PAMMDES), anilinomethyl trimethoxy silane (PAMTMS) and anilinomethyl methyl dimethoxy silane (PAMMDMS);
  • the molar ratio between the reactive organosilicon monomer and the diisocyanate is from 1 :1 .1 to 1 :5, preferably from 1 :1 .2 to 1 :4, most preferably
  • the present invention further provides a solvent-free reactive poly(siloxane-urethane) emulsion comprising said prepoly(siloxane-urethane) as well as protecting colloid and emulsifying agent dispersed in water.
  • the solid content of this emulsion is of 25-55wt%, preferably of 30-45wt%, and the latex particle size of this emulsion is of less than 500nm, preferably of 100-300nm.
  • the present invention further provides a process for preparing the solvent-free reactive poly(siloxane-urethane) emulsion through phase inversion emulsification without any organic solvent, comprising the following steps: a1 . adding protecting colloid into the inventive prepoly(siloxane-urethane), then homogenizing the mixture with stirring; b1 . cooling down the mixture from step a1 naturally, then adding thereinto an aqueous solution of emulsifying agent with stirring; and c1 .
  • step a1 the mixing is carried out at a temperature same as that for the polymerization for preparing the prepoly(siloxane-urethane), and the mixing is continued with stirring for a time from 5 to 240 minutes, preferably from 10 to 120 minutes, most preferably from 15 to 60 minutes, so that the prepoly(siloxane-urethane) is mixed with the protecting colloid thoroughly;
  • the protecting colloid is used in an amount of 0.1 -20wt%, preferably 0.5-10wt%, most preferably 1 -7wt%, based on the total solid content; and the protecting colloid is a polyether-modified polysiloxane having the following schematic formula:
  • x is an integer from 10 to 10000
  • y is an integer from 0 to 10000
  • n is an integer from 5 to 2000
  • m is an integer from 0 to 2000
  • R is H, CH 3 , C 2 H 5 Or OCCH 3 ;
  • said protecting colloid is prepared according to the process described in literature (Cai Zhenyun et al., organosilicon materials, 2005, 19 (4):20-22).
  • step b1 the mixture from step a1 is cooled down naturally and the temperature of the mixture is controlled in the range of 20-90 0 C and this temperature is generally lower than that for the polymerization for preparing the prepoly(siloxane-urethane), then an aqueous solution of emulsifying agent is added into the mixture dropwise or in batch;
  • the emulsifying agent is an anionic emulsifying agent or a mixture of anionic emulsifying agent and nonionic emulsifying agent;
  • the anionic emulsifying agent is selected from the group consisting of aliphatic sulphate, aromatic sulphate, aliphatic sulphonate and aromatic sulphonate, preferably aliphatic sulphate such as sodium dodecyl sulphate (SDS);
  • the nonionic emulsifying agent is selected from the group consisting of aliphatic sulphate, aromatic sulphate, aliphatic sulphonate
  • the stirring rate is initially of 5-100rpm, preferably 5-75rpm, most preferably 10-50rpm, and increasing gradually with the prepoly(siloxane-urethane) being dispersed into the water, then finally of 150-3000rpm, preferably 200-2500rpm, most preferably 200-2000rpm; after the prepoly(siloxane-urethane) being dispersed sufficiently, a dilute acid of 2-10wt% is added dropwise with stirring to adjust the emulsion to a pH value in the range of 5-9, preferably 5.5-8.5, most preferably 6-8, and said dilute acid is an inorganic acid such as dilute hydrochloric acid, dilute sulfuric acid etc or an organic acid such as dilute acetic acid etc, preferably dilute hydrochloric acid.
  • the prepoly(siloxane-urethane) and the poly(siloxane-urethane) emulsion thus being cost- and energy-economic and environmental friendly.
  • the molecular weight, hydrophilicity and stiffness etc of the prepoly(siloxane-urethane) can be controlled by the raw materials as well as the ratio thereof.
  • the protecting colloid is used in the phase inversion emulsification of the prepoly(siloxane-urethane), the freeze-thaw stability as well as the storage stability of the poly(siloxane-urethane) emulsion at ambient temperature and at 50 0 C are improved greatly.
  • the solid content of the emulsion is measued by weight method
  • the latex particle size is measued at 25°C using Zetasize-3000HS Laser Particle Sizer from Malvern Company, Great Britain
  • the viscosity of the emulsion is measured at 25 0 C using domestic digital rotary viscometer NDJ-8S
  • the freeze-thaw stability of the emulsion is measured according to the national standard of People's Republic of China GB9268-88
  • the storage stability of the emulsion at ambient temperature and at 50 0 C is measured in a climatic chamber by static method.
  • the latex film is made according to the national standard of People's Republic of China GB1727-92; the adhesion, flexibility and impact strength of the latex film are measured according to the national standards of People's Republic of China GB1720-79, GB/T1731 -93 and GB/T1732-93 respectively; the temperature at 1 wt% of weight loss of the latex film is measured in thermogravimetric analyzer TGA2050 from Universal Company (USA) with temperature increasing rate of 20 °C/min by thermogravimetric analysis under nitrogen atomosphere; and the crosslinkage degree of the latex film is defined as the polymer weight percents remaining after extracting the latex film by the Soxhlet method with butanone as solvent for 24 hours.
  • protecting colloid in the schematic formula:
  • the poly(siloxane-urethane) emulsion according to present invention is with high solid content, small latex particle size, high theoretical amount of organosilicon as well as excellent storage stability and freeze-thaw stability, and the latex film made from the poly(siloxane-urethane) emulsion is with high crosslinkage degree, high decomposition temperature as well as excellent mechanical properties such as excellent adhesion, flexibility and impact strength etc.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Manufacturing & Machinery (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne un prépoly(siloxane-uréthane) réactif synthétisé par polymérisation brute au moyen d'organosilicium réactif, d'isocyanate, de polyéther, de monomère hydrophile etc. en tant que matières premières, puis une émulsion de poly(siloxane-uréthane) hautement stable préparée par émulsification par inversion de phase sans solvant organique; cette émulsion peut être réticulée rapidement avec l'évaporation d'humidité à température ambiante en vue de former une pellicule de latex présentant d'excellentes propriétés. Le procédé de l'invention présente quelques avantages, parmi lesquels, un faible investissement de capitaux pour les équipements, une procédure simple et un faible coût de production, et l'émulsion obtenue peut être largement utilisée dans des domaines tels que la production écologique de gommes de scellement à l'eau et de peintures à l'eau ainsi que dans le traitement du cuir, la fabrication du papier, la finition des textiles etc.
PCT/EP2008/066351 2007-12-26 2008-11-27 Prépoly(siloxane-uréthane) réactif et émulsion de poly(siloxane-uréthane) réactif sans solvant préparée à partir de celui-ci WO2009080441A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CNA2007103002846A CN101469055A (zh) 2007-12-26 2007-12-26 活性有机硅-聚氨酯预聚体及由其制备的无溶剂活性有机硅-聚氨酯乳液
CN200710300284.6 2007-12-26

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Publication Number Publication Date
WO2009080441A1 true WO2009080441A1 (fr) 2009-07-02

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Cited By (4)

* Cited by examiner, † Cited by third party
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CN102174167A (zh) * 2011-02-17 2011-09-07 陈华 一种合成革用有机硅改性聚氨酯树脂及其制备方法
KR20160089921A (ko) 2015-01-20 2016-07-29 주식회사 비아이티범우연구소 반응성 실란기를 갖는 우레탄 올리고머 및 코어/쉘 구조의 수분산 폴리우레탄 수지 조성물 및 이의 제조방법
CN111995730A (zh) * 2020-09-03 2020-11-27 东来涂料技术（上海）股份有限公司 一种水性聚氨酯、水性聚氨酯涂料及其制备方法
CN112313285A (zh) * 2018-06-27 2021-02-02 Dic株式会社 氨基甲酸酯树脂组合物、表面处理剂及物品

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CN102408870B (zh) * 2011-08-16 2014-06-11 北京天山新材料技术股份有限公司 硅烷封端聚合物的密封胶及制备方法
ES2714429T3 (es) * 2011-09-29 2019-05-28 Covestro Deutschland Ag Prepolímero terminado en alfa-alcoxisilano para espumas para pulverización de endurecimiento rápido con solubilidad de gas propelente mejorada
CN103012721A (zh) * 2012-12-21 2013-04-03 青岛海尔软件有限公司 一种氨基硅烷改性水性聚氨酯乳液
CN108623778B (zh) * 2017-03-15 2020-05-05 中国科学院福建物质结构研究所 一种无有机溶剂制备水性聚氨酯分散体的方法
CN109503842A (zh) * 2018-11-16 2019-03-22 天津工业大学 一种用于三聚氰胺检测的溶胶凝胶分子印迹微球的制备方法
CN111054283B (zh) * 2019-12-06 2021-03-12 深圳先进电子材料国际创新研究院 一种聚氨酯改性有机硅树脂为壳材的相变储能微胶囊及其制备方法
CN111732708B (zh) * 2020-06-04 2022-04-12 旭川化学（苏州）有限公司 一种软质高回弹水性聚氨酯树脂及其制备方法和应用

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US5760123A (en) * 1994-04-19 1998-06-02 Herberts Gesellschaft Mit Beschrankter Haftung Aqueous dispersion of polyurethanes containing siloxane linkages, production thereof and use in coating compositions
US6437041B1 (en) * 1998-02-07 2002-08-20 E. I. Du Pont De Nemours & Company Aqueous coating agent, preparation of the same and use thereof for multi-layered lacquering

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5760123A (en) * 1994-04-19 1998-06-02 Herberts Gesellschaft Mit Beschrankter Haftung Aqueous dispersion of polyurethanes containing siloxane linkages, production thereof and use in coating compositions
US6437041B1 (en) * 1998-02-07 2002-08-20 E. I. Du Pont De Nemours & Company Aqueous coating agent, preparation of the same and use thereof for multi-layered lacquering

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102174167A (zh) * 2011-02-17 2011-09-07 陈华 一种合成革用有机硅改性聚氨酯树脂及其制备方法
KR20160089921A (ko) 2015-01-20 2016-07-29 주식회사 비아이티범우연구소 반응성 실란기를 갖는 우레탄 올리고머 및 코어/쉘 구조의 수분산 폴리우레탄 수지 조성물 및 이의 제조방법
CN112313285A (zh) * 2018-06-27 2021-02-02 Dic株式会社 氨基甲酸酯树脂组合物、表面处理剂及物品
CN111995730A (zh) * 2020-09-03 2020-11-27 东来涂料技术（上海）股份有限公司 一种水性聚氨酯、水性聚氨酯涂料及其制备方法

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