AU737520B2 - Thermosetting compositions containing carbamate-functional polymers prepared using atom transfer radical polymerization - Google Patents
Thermosetting compositions containing carbamate-functional polymers prepared using atom transfer radical polymerization Download PDFInfo
- Publication number
- AU737520B2 AU737520B2 AU57927/99A AU5792799A AU737520B2 AU 737520 B2 AU737520 B2 AU 737520B2 AU 57927/99 A AU57927/99 A AU 57927/99A AU 5792799 A AU5792799 A AU 5792799A AU 737520 B2 AU737520 B2 AU 737520B2
- Authority
- AU
- Australia
- Prior art keywords
- carbamate
- group
- functional polymer
- polymer
- composition
- 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.)
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- 239000000203 mixture Substances 0.000 title claims description 127
- 229920001002 functional polymer Polymers 0.000 title claims description 114
- 229920001187 thermosetting polymer Polymers 0.000 title claims description 60
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 title claims description 39
- 229920000642 polymer Polymers 0.000 claims description 127
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 103
- 239000000178 monomer Substances 0.000 claims description 85
- -1 polycyclic aromatic compounds Chemical class 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 58
- 239000008199 coating composition Substances 0.000 claims description 52
- 239000003999 initiator Substances 0.000 claims description 48
- 238000000576 coating method Methods 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000007787 solid Substances 0.000 claims description 26
- 239000002131 composite material Substances 0.000 claims description 24
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 239000000758 substrate Substances 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 239000003431 cross linking reagent Substances 0.000 claims description 18
- 229920002554 vinyl polymer Polymers 0.000 claims description 15
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- 125000000524 functional group Chemical group 0.000 claims description 13
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
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- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
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- 239000002585 base Substances 0.000 description 23
- 239000003054 catalyst Substances 0.000 description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 14
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- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 10
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
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- 230000015572 biosynthetic process Effects 0.000 description 8
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 8
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- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- BSBQJOWZSCCENI-UHFFFAOYSA-N 3-hydroxypropyl carbamate Chemical compound NC(=O)OCCCO BSBQJOWZSCCENI-UHFFFAOYSA-N 0.000 description 3
- OAOABCKPVCUNKO-UHFFFAOYSA-N 8-methyl Nonanoic acid Chemical compound CC(C)CCCCCCC(O)=O OAOABCKPVCUNKO-UHFFFAOYSA-N 0.000 description 3
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- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 3
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- XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
-
- 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
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3823—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups
- C08G18/3831—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups containing urethane groups
-
- 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
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
- C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
- C09D201/025—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Paints Or Removers (AREA)
- Graft Or Block Polymers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerization Catalysts (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9861698P | 1998-08-31 | 1998-08-31 | |
| US60/098616 | 1998-08-31 | ||
| US09/375020 | 1999-08-16 | ||
| US09/375,020 US6306965B1 (en) | 1998-08-31 | 1999-08-16 | Thermosetting compositions containing carbamate-functional polylmers prepared using atom transfer radical polymerization |
| PCT/US1999/019797 WO2000012566A1 (en) | 1998-08-31 | 1999-08-30 | Thermosetting compositions containing carbamate-functional polymers prepared using atom transfer radical polymerization |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU5792799A AU5792799A (en) | 2000-03-21 |
| AU737520B2 true AU737520B2 (en) | 2001-08-23 |
Family
ID=26794930
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU57927/99A Ceased AU737520B2 (en) | 1998-08-31 | 1999-08-30 | Thermosetting compositions containing carbamate-functional polymers prepared using atom transfer radical polymerization |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6306965B1 (enExample) |
| EP (1) | EP1112290B1 (enExample) |
| JP (3) | JP2002523569A (enExample) |
| KR (1) | KR100420816B1 (enExample) |
| AU (1) | AU737520B2 (enExample) |
| BR (1) | BR9913485A (enExample) |
| CA (1) | CA2340703C (enExample) |
| DE (1) | DE69919180T2 (enExample) |
| ES (1) | ES2226436T3 (enExample) |
| MX (1) | MX224470B (enExample) |
| WO (1) | WO2000012566A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6306965B1 (en) * | 1998-08-31 | 2001-10-23 | Ppg Industries Ohio, Inc. | Thermosetting compositions containing carbamate-functional polylmers prepared using atom transfer radical polymerization |
| US6355729B1 (en) | 1998-08-31 | 2002-03-12 | Ppg Industries Ohio, Inc. | Electrodepositable coating compositions comprising amine salt group-containing polymers prepared by atom transfer radical polymerization |
| US7205029B2 (en) * | 2000-12-19 | 2007-04-17 | Basf Corporation | Method of providing cured coating films free of popping defects |
| JP4012058B2 (ja) * | 2001-12-21 | 2007-11-21 | キヤノン株式会社 | リサイクル性重合体、その製造方法、ならびにリサイクル処理方法 |
| AU2003209067A1 (en) * | 2002-02-15 | 2003-09-09 | Ppg Industries Ohio, Inc. | Compositions containing copolymers of post-polymerization reacted (meth)acrylate monomers |
| US6784248B2 (en) | 2002-02-15 | 2004-08-31 | Ppg Industries Ohio, Inc. | Thermosetting compositions containing alternating copolymers of isobutylene type monomers |
| EP1474478B1 (en) * | 2002-02-15 | 2008-12-31 | PPG Industries Ohio, Inc. | Waterborne thermosetting compositions containing alternating copolymers of isobutylene type monomers |
| ES2290444T3 (es) * | 2002-02-15 | 2008-02-16 | Ppg Industries Ohio, Inc. | Composiciones de formacion de pelicula de soporte acuoso que comprende copolimeros que contienen monomeros de tipo isobutileno. |
| US6890994B2 (en) * | 2002-10-31 | 2005-05-10 | Basf Corporation | Curable coating compositions with carbamate-containing acrylic polymers |
| US20050032978A1 (en) * | 2003-08-06 | 2005-02-10 | O'dwyer James B. | Etherified carbamate functional copolymers of isobutylene type monomers, and their use in curable compositions |
| US7342077B2 (en) | 2004-06-04 | 2008-03-11 | Basf Corporation | Acrylic composition and a method of forming the same via free-radical polymerization |
| US7250480B2 (en) | 2004-03-04 | 2007-07-31 | Basf Corporation | Acrylic composition and a curable coating composition including the same |
| US7220811B2 (en) | 2004-03-04 | 2007-05-22 | Basf Corporation | Acrylic composition and a curable coating composition including the same |
| US7375174B2 (en) | 2004-03-04 | 2008-05-20 | Basf Corporation | Acrylic composition and a curable coating composition including the same |
| US7144966B2 (en) | 2004-03-04 | 2006-12-05 | Basf Corporation | Acrylic composition for use in coating applications and a method of forming the same |
| JP4528333B2 (ja) * | 2008-01-25 | 2010-08-18 | 株式会社有沢製作所 | 立体画像表示装置およびその製造方法 |
| JP5094578B2 (ja) * | 2008-06-17 | 2012-12-12 | 花王株式会社 | グラフトポリマーの製造方法 |
| US9334234B2 (en) * | 2014-05-08 | 2016-05-10 | Basf Coatings Gmbh | Method using titanium catalyst for producing carbamate-functional materials |
| RU2562267C1 (ru) * | 2014-12-24 | 2015-09-10 | Сергей Вячеславович Штепа | Способ получения защитного композиционного термопластичного покрытия и способ его нанесения |
| EP3363835B1 (en) * | 2017-02-20 | 2023-10-11 | The Gillette Company LLC | Article comprising a polymer layer |
| CN110964175A (zh) * | 2019-11-20 | 2020-04-07 | 武汉科技大学 | 基于氨基甲酸叔醇酯交换的类玻璃聚氨酯弹性体、制备方法及应用 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5605965A (en) * | 1992-10-23 | 1997-02-25 | Basf Corporation | High gloss and/or high DOI coating utilizing carbamate-functional polymer composition |
| WO1997018247A1 (en) * | 1995-11-15 | 1997-05-22 | Carnegie Mellon University | Improved processes based on atom (or group) transfer radical polymerization and novel (co)polymers having useful structures and properties |
| WO1997026305A1 (en) * | 1996-01-16 | 1997-07-24 | Ppg Industries, Inc. | Color-plus-clear composite coatings that contain polymers having carbamate functionality |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3479328A (en) | 1966-11-18 | 1969-11-18 | Ashland Oil Inc | Novel monomers and polymers |
| US4147679A (en) | 1976-06-02 | 1979-04-03 | Ppg Industries, Inc. | Water-reduced urethane coating compositions |
| DE3166673D1 (en) | 1980-04-14 | 1984-11-22 | Ici Plc | Multi-layer coating process involving use of aqueous basecoat composition containing crosslinked polymer microparticles and having a pseudoplastic or thixotropic character |
| US5071904A (en) | 1989-05-30 | 1991-12-10 | Ppg Industries, Inc. | Waterborne coating compositions for automotive applications |
| ES2101353T3 (es) * | 1992-10-30 | 1997-07-01 | Ppg Industries Inc | Composiciones filmogenas endurecibles con aminoplastico que producen peliculas resistentes al ataque del acido. |
| US5384367A (en) * | 1993-04-19 | 1995-01-24 | Ppg Industries, Inc. | Carbamate urea or urethane-functional epoxy acrylic with polyacid |
| US5373069A (en) * | 1993-07-28 | 1994-12-13 | Basf Corporation | Curable carbamate-functional polymers |
| DE4432897C2 (de) * | 1994-09-15 | 1999-05-20 | Dainippon Ink & Chemicals | Vernetzende Massen sowie Verfahren zur Herstellung vernetzter Materialien |
| US5552497A (en) * | 1994-12-29 | 1996-09-03 | Basf Corporation | Method of preparing carbamate-functional polymer |
| US5763548A (en) | 1995-03-31 | 1998-06-09 | Carnegie-Mellon University | (Co)polymers and a novel polymerization process based on atom (or group) transfer radical polymerization |
| US5789487A (en) | 1996-07-10 | 1998-08-04 | Carnegie-Mellon University | Preparation of novel homo- and copolymers using atom transfer radical polymerization |
| TW593347B (en) | 1997-03-11 | 2004-06-21 | Univ Carnegie Mellon | Improvements in atom or group transfer radical polymerization |
| US6306965B1 (en) * | 1998-08-31 | 2001-10-23 | Ppg Industries Ohio, Inc. | Thermosetting compositions containing carbamate-functional polylmers prepared using atom transfer radical polymerization |
-
1999
- 1999-08-16 US US09/375,020 patent/US6306965B1/en not_active Expired - Fee Related
- 1999-08-30 CA CA002340703A patent/CA2340703C/en not_active Expired - Fee Related
- 1999-08-30 AU AU57927/99A patent/AU737520B2/en not_active Ceased
- 1999-08-30 KR KR20017002612A patent/KR100420816B1/ko not_active Expired - Fee Related
- 1999-08-30 BR BR9913485-3A patent/BR9913485A/pt not_active Application Discontinuation
- 1999-08-30 JP JP2000567579A patent/JP2002523569A/ja active Pending
- 1999-08-30 ES ES99945306T patent/ES2226436T3/es not_active Expired - Lifetime
- 1999-08-30 WO PCT/US1999/019797 patent/WO2000012566A1/en not_active Ceased
- 1999-08-30 DE DE69919180T patent/DE69919180T2/de not_active Expired - Lifetime
- 1999-08-30 EP EP99945306A patent/EP1112290B1/en not_active Expired - Lifetime
- 1999-09-01 MX MXPA01001967 patent/MX224470B/es not_active IP Right Cessation
-
2004
- 2004-09-24 JP JP2004278575A patent/JP3894933B2/ja not_active Expired - Fee Related
-
2006
- 2006-10-27 JP JP2006293357A patent/JP2007070639A/ja not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5605965A (en) * | 1992-10-23 | 1997-02-25 | Basf Corporation | High gloss and/or high DOI coating utilizing carbamate-functional polymer composition |
| WO1997018247A1 (en) * | 1995-11-15 | 1997-05-22 | Carnegie Mellon University | Improved processes based on atom (or group) transfer radical polymerization and novel (co)polymers having useful structures and properties |
| WO1997026305A1 (en) * | 1996-01-16 | 1997-07-24 | Ppg Industries, Inc. | Color-plus-clear composite coatings that contain polymers having carbamate functionality |
Also Published As
| Publication number | Publication date |
|---|---|
| AU5792799A (en) | 2000-03-21 |
| CA2340703A1 (en) | 2000-03-09 |
| US6306965B1 (en) | 2001-10-23 |
| KR100420816B1 (ko) | 2004-03-02 |
| MX224470B (es) | 2004-11-24 |
| ES2226436T3 (es) | 2005-03-16 |
| EP1112290A1 (en) | 2001-07-04 |
| CA2340703C (en) | 2004-11-02 |
| WO2000012566A1 (en) | 2000-03-09 |
| DE69919180D1 (de) | 2004-09-09 |
| EP1112290B1 (en) | 2004-08-04 |
| MXPA01001967A (es) | 2001-08-01 |
| BR9913485A (pt) | 2001-05-22 |
| JP3894933B2 (ja) | 2007-03-22 |
| KR20010074871A (ko) | 2001-08-09 |
| JP2002523569A (ja) | 2002-07-30 |
| DE69919180T2 (de) | 2005-07-28 |
| JP2005089760A (ja) | 2005-04-07 |
| JP2007070639A (ja) | 2007-03-22 |
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| FGA | Letters patent sealed or granted (standard patent) |