RU2007117704A - Способ производства полиуретанди(мет)акрилатов - Google Patents
Способ производства полиуретанди(мет)акрилатов Download PDFInfo
- Publication number
- RU2007117704A RU2007117704A RU2007117704/04A RU2007117704A RU2007117704A RU 2007117704 A RU2007117704 A RU 2007117704A RU 2007117704/04 A RU2007117704/04 A RU 2007117704/04A RU 2007117704 A RU2007117704 A RU 2007117704A RU 2007117704 A RU2007117704 A RU 2007117704A
- Authority
- RU
- Russia
- Prior art keywords
- mol
- diisocyanate
- diol
- component
- omega
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title 1
- 150000002009 diols Chemical class 0.000 claims abstract 20
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract 10
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 8
- 238000000034 method Methods 0.000 claims abstract 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims abstract 4
- 239000004814 polyurethane Substances 0.000 claims abstract 4
- 229920002635 polyurethane Polymers 0.000 claims abstract 4
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims abstract 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims abstract 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract 2
- 239000005058 Isophorone diisocyanate Substances 0.000 claims abstract 2
- OMRDSWJXRLDPBB-UHFFFAOYSA-N N=C=O.N=C=O.C1CCCCC1 Chemical compound N=C=O.N=C=O.C1CCCCC1 OMRDSWJXRLDPBB-UHFFFAOYSA-N 0.000 claims abstract 2
- JTDWCIXOEPQECG-UHFFFAOYSA-N N=C=O.N=C=O.CCCCCC(C)(C)C Chemical compound N=C=O.N=C=O.CCCCCC(C)(C)C JTDWCIXOEPQECG-UHFFFAOYSA-N 0.000 claims abstract 2
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 claims abstract 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims abstract 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000002904 solvent Substances 0.000 claims abstract 2
- 239000011230 binding agent Substances 0.000 claims 1
- 238000004140 cleaning Methods 0.000 claims 1
- 239000008199 coating composition Substances 0.000 claims 1
- TWLCPLJMACDPFF-UHFFFAOYSA-N cyclohexane;1,2-diisocyanatoethane Chemical compound C1CCCCC1.O=C=NCCN=C=O TWLCPLJMACDPFF-UHFFFAOYSA-N 0.000 claims 1
- -1 diol isocyanate Chemical class 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- AAMSQLYHKQGAEL-UHFFFAOYSA-N 1-(isocyanatomethyl)-2-(5-isocyanatopentyl)benzene Chemical compound O=C=NCCCCCC1=CC=CC=C1CN=C=O AAMSQLYHKQGAEL-UHFFFAOYSA-N 0.000 abstract 1
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 abstract 1
- 238000011403 purification operation Methods 0.000 abstract 1
Classifications
-
- 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/81—Unsaturated isocyanates or isothiocyanates
- C08G18/8141—Unsaturated isocyanates or isothiocyanates masked
- C08G18/815—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen
- C08G18/8158—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen
- C08G18/8175—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen with esters of acrylic or alkylacrylic acid having only one group containing 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3212—Polyhydroxy compounds containing cycloaliphatic 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
- 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
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- 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
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
-
- 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
- C08G2150/00—Compositions for coatings
- C08G2150/20—Compositions for powder coatings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Claims (6)
1. Способ получения полиуретанди(мет)акрилатов, включающий взаимодействие диизоцианатного компонента, диольного компонента и гидрокси-С2-С4-алкил(мет)акрилата в отсутствие растворителя и без последующих действий по очистке в мольном соотношении х:(х-1):2, где х означает любое значение от 2 до 5, в котором от 50 до 80 мол.% диизоцианатного компонента составляет 1,6-гександиизоцианат, а от 20 до 50 мол.% составляет(ют) один или два диизоцианата, причем каждый составляет, по меньшей мере, 10 мол.% диизоцианатного компонента, и выбраны из группы, состоящей из толуилендиизоцианата, дифенилметандиизоцианата, дициклогексилметандиизоцианата, изофорондиизоцианата, триметилгександиизоцианата, циклогександиизоцианата, циклогександиметилендиизоцианата и тетраметиленксилилен диизоцианата, где мол.% соответствующих диизоцианатов составляют в сумме 100 мол.%, в котором диольный компонент включает в себя не более четырех различных диолов и от 20 до 100 мол.% диольного компонента составляет, по меньшей мере, один линейный алифатический альфа,омега-С2-С12-диол, а от 0 до 80 мол.% составляет, по меньшей мере, один (цикло)алифатический диол, который отличается от линейных алифатических альфа,омега-С2-С12-диолов, в котором каждый диол диольного компонента составляет, по меньшей мере, 10 мол.% в диольном компоненте и где мол.% соответствующих диолов составляют в сумме 100 мол.%.
2. Способ по п. 1, в котором от 80 до 100 мол.% диольного компонента составляет, по меньшей мере, один линейный алифатический альфа,омега-С2-С12-диол, а от 0 до 20 мол.% составляет, по меньшей мере, один (цикло)алифатический диол, который отличается от линейных алифатических альфа,омега-С2-С12-диолов.
3. Способ по п. 1, в котором диольный компонент состоит из от одного до четырех линейных алифатических альфа,омега-С2-С12-диолов.
4. Способ по п. 1, в котором диольный компонент состоит из одного линейного алифатического альфа,омега-С2-С12-диола.
5. Полиуретанди(мет)акрилаты, полученные согласно любому из предшествующих пунктов.
6. Композиции порошковых покрытий, содержащие полиуретанди(мет)акрилаты, полученные согласно способу по любому из пп.1-4, в качестве связующих.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/963,907 US7071242B2 (en) | 2004-10-13 | 2004-10-13 | Process for the production of polyurethane di(meth)acrylates |
| US10/963,907 | 2004-10-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2007117704A true RU2007117704A (ru) | 2008-11-20 |
| RU2355714C2 RU2355714C2 (ru) | 2009-05-20 |
Family
ID=35539295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2007117704/04A RU2355714C2 (ru) | 2004-10-13 | 2005-10-13 | Способ производства полиуретанди(мет)акрилатов |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7071242B2 (ru) |
| EP (1) | EP1828275B1 (ru) |
| CN (1) | CN101035828A (ru) |
| AT (1) | ATE397633T1 (ru) |
| CA (1) | CA2578528A1 (ru) |
| DE (1) | DE602005007382D1 (ru) |
| ES (1) | ES2308568T3 (ru) |
| NO (1) | NO20072309L (ru) |
| RU (1) | RU2355714C2 (ru) |
| WO (1) | WO2006044506A1 (ru) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060173122A1 (en) * | 2005-02-01 | 2006-08-03 | Carmen Flosbach | Non-aqueous, liquid coating compositions curable by free-radical polymerization of olefinic double bonds |
| EP1966262B1 (en) * | 2005-12-09 | 2016-03-09 | Coatings Foreign IP Co. LLC | Non-aqueous, liquid coating compositions |
| EP2003174B1 (en) * | 2006-03-31 | 2018-05-02 | Fujikura Kasei Co., Ltd. | Hard coating composition for metal base |
| US9095878B2 (en) | 2006-08-02 | 2015-08-04 | Ford Motor Company | Coating compositions and methods of applying the same |
| US8227038B2 (en) | 2007-01-12 | 2012-07-24 | E I Du Pont De Nemours And Company | Adhesion promoting cleaner solution |
| TWI434902B (zh) * | 2007-06-26 | 2014-04-21 | Fujikura Kasei Kk | 金屬薄膜用塗料組成物以及以此形成之亮光性複合塗膜 |
| US20090012202A1 (en) * | 2007-07-03 | 2009-01-08 | Henkel Corporation | Acrylated Urethanes, Processes for Making the Same and Curable Compositions Including the Same |
| EP2055749A2 (en) | 2007-10-30 | 2009-05-06 | E. I. Du Pont de Nemours and Company | Process for the production of powder coating compositions |
| US8653185B2 (en) | 2010-04-30 | 2014-02-18 | Hewlett-Packard Development Company, L.P. | Method of forming ionically-charged, encapsulated colorant nanoparticles |
| US20140343221A1 (en) | 2011-12-21 | 2014-11-20 | Axalta Coatng Systems Ip Co., Llc | Powder coating composition |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4232013A1 (de) * | 1992-09-24 | 1994-03-31 | Bayer Ag | Acryloylgruppen aufweisende Polyurethane, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Bindemittel für Überzugsmassen |
| GB2290793B (en) * | 1994-06-20 | 1998-05-06 | Cray Valley Ltd | Powder coating compositions |
| DE19947522A1 (de) | 1999-10-02 | 2001-04-05 | Basf Ag | Polymerisierbare olefinisch ungesättigte Doppelbindungen enthaltende feste aliphatische Polyurethane auf der Basis linearer Diisocyanate und ihre Verwendung |
| US20050187341A1 (en) * | 2004-02-19 | 2005-08-25 | Carmen Flosbach | Process for the production of polyurethane di(meth)acrylates |
-
2004
- 2004-10-13 US US10/963,907 patent/US7071242B2/en not_active Expired - Fee Related
-
2005
- 2005-10-13 ES ES05804253T patent/ES2308568T3/es active Active
- 2005-10-13 CN CNA2005800343566A patent/CN101035828A/zh active Pending
- 2005-10-13 AT AT05804253T patent/ATE397633T1/de not_active IP Right Cessation
- 2005-10-13 EP EP05804253A patent/EP1828275B1/en not_active Not-in-force
- 2005-10-13 CA CA002578528A patent/CA2578528A1/en not_active Abandoned
- 2005-10-13 RU RU2007117704/04A patent/RU2355714C2/ru active
- 2005-10-13 WO PCT/US2005/036765 patent/WO2006044506A1/en active Application Filing
- 2005-10-13 DE DE602005007382T patent/DE602005007382D1/de active Active
-
2007
- 2007-05-04 NO NO20072309A patent/NO20072309L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US7071242B2 (en) | 2006-07-04 |
| ATE397633T1 (de) | 2008-06-15 |
| DE602005007382D1 (de) | 2008-07-17 |
| NO20072309L (no) | 2007-05-04 |
| US20060079659A1 (en) | 2006-04-13 |
| RU2355714C2 (ru) | 2009-05-20 |
| ES2308568T3 (es) | 2008-12-01 |
| EP1828275A1 (en) | 2007-09-05 |
| WO2006044506A1 (en) | 2006-04-27 |
| CA2578528A1 (en) | 2006-04-27 |
| EP1828275B1 (en) | 2008-06-04 |
| CN101035828A (zh) | 2007-09-12 |
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