CA2122534A1 - Tri-carbamate-functional crosslinking agents - Google Patents
Tri-carbamate-functional crosslinking agentsInfo
- Publication number
- CA2122534A1 CA2122534A1 CA002122534A CA2122534A CA2122534A1 CA 2122534 A1 CA2122534 A1 CA 2122534A1 CA 002122534 A CA002122534 A CA 002122534A CA 2122534 A CA2122534 A CA 2122534A CA 2122534 A1 CA2122534 A1 CA 2122534A1
- Authority
- CA
- Canada
- Prior art keywords
- crosslinking agents
- carbamate
- tri
- functional crosslinking
- compounds
- 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.)
- Granted
Links
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
- C08G18/28—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
- 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
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/40—Chemically modified polycondensates
-
- 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
- C08G18/3842—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
- C08G18/3851—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing three nitrogen atoms in the ring
- C08G18/3853—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing three nitrogen atoms in the ring containing cyanurate and/or isocyanurate groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31942—Of aldehyde or ketone condensation product
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Compounds are described having the formula:
(See formula I), wherein Z represents a cyanuric ring nucleus or the residue of a polyol, L1, L2, and L3 each independently represents a divalent linking group or a covalent bond, and R1, R2, and R3 each independently represents H, alkyl, cycloalkyl, or aryl.
These compounds are useful as crosslinking agents for curable compositions such as coating compositions.
(See formula I), wherein Z represents a cyanuric ring nucleus or the residue of a polyol, L1, L2, and L3 each independently represents a divalent linking group or a covalent bond, and R1, R2, and R3 each independently represents H, alkyl, cycloalkyl, or aryl.
These compounds are useful as crosslinking agents for curable compositions such as coating compositions.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/056,514 | 1993-04-30 | ||
US08/056,514 US5336566A (en) | 1993-04-30 | 1993-04-30 | Tri-carbamate-functional crosslinking agents |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2122534A1 true CA2122534A1 (en) | 1994-10-31 |
CA2122534C CA2122534C (en) | 2003-03-11 |
Family
ID=22004909
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA 2122534 Expired - Lifetime CA2122534C (en) | 1993-04-30 | 1994-04-29 | Tri-carbamate-functional crosslinking agents |
Country Status (10)
Country | Link |
---|---|
US (1) | US5336566A (en) |
EP (1) | EP0622387B1 (en) |
JP (1) | JP3506764B2 (en) |
KR (1) | KR100326622B1 (en) |
CN (1) | CN1064054C (en) |
AU (1) | AU683046B2 (en) |
BR (1) | BR9401645A (en) |
CA (1) | CA2122534C (en) |
DE (1) | DE69411221T2 (en) |
ES (1) | ES2120535T3 (en) |
Families Citing this family (65)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5356669A (en) * | 1992-10-23 | 1994-10-18 | Basf Corporation | Composite color-plus-clear coating utilizing carbamate-functional polymer composition in the clearcoat |
JP2672031B2 (en) * | 1992-10-30 | 1997-11-05 | ピーピージー インダストリーズ,インコーポレイテッド | Aminoplast-curable film-forming composition that gives a film having acid etching resistance |
US5770650A (en) * | 1995-10-06 | 1998-06-23 | Basf Corporation | Curable compositions for coatings |
US5827930A (en) * | 1995-10-06 | 1998-10-27 | Basf Corporation | Curable coating composition |
US6165618A (en) * | 1994-11-03 | 2000-12-26 | Basf Corporation | Curable coating compositions containing carbamate resin and additives |
US6423788B1 (en) * | 1995-10-06 | 2002-07-23 | Basf Corporation | Curable coating composition |
US5792810A (en) * | 1995-10-06 | 1998-08-11 | Basf Corporation | Curable coating composition including compound having carbamate and hydroxyl functionality |
US5756213A (en) * | 1995-10-06 | 1998-05-26 | Basf Corporation | Curable coating composition having carbonate-containing component |
US5854385A (en) * | 1995-10-06 | 1998-12-29 | Basf Corporation | Coating compositions with low molecular weight carbamate or urea component |
EP0661315B1 (en) * | 1994-01-03 | 1999-03-31 | Basf Corporation | Extended isocyanurates for use as curing agents in coating compostitions |
WO1995029947A1 (en) * | 1994-04-29 | 1995-11-09 | Ppg Industries, Inc. | Flexible aminoplast-curable film-forming compositions providing films having resistance to acid etching |
US5976701A (en) * | 1994-04-29 | 1999-11-02 | Ppg Industries Ohio, Inc. | Flexible aminoplast-curable film-forming compositions and composite coating |
US5709950A (en) * | 1994-04-29 | 1998-01-20 | Ppg Industries, Inc. | Color-plus-clear composite coatings that contain polymers having carbamate functionality |
US5532061A (en) * | 1994-12-21 | 1996-07-02 | Basf Corporation | Carbamate-functional polyester polymer or oligomer having pendant carbomate groups |
US5451656A (en) * | 1994-12-21 | 1995-09-19 | Basf Corporation | Carbamate-functional polyester polymer or oligomer and coating composition |
US6498266B1 (en) | 1995-10-06 | 2002-12-24 | Basf Corporation | Method of preparing a carbamate- or urea-functional compound |
US5766769A (en) * | 1995-10-06 | 1998-06-16 | Basf Corporation | Curable composition for coatings |
US5593733A (en) * | 1995-11-21 | 1997-01-14 | Ppg Industries, Inc. | Coating composition containing polyester polymers with terminal carbamate groups and polymeric polyol derived from ethylenically unsaturated monomers |
US5959040A (en) * | 1996-09-04 | 1999-09-28 | Ppg Industries Ohio, Inc. | Film-forming composition suitable for use as a monocoat |
US5759694A (en) * | 1996-09-04 | 1998-06-02 | Ppg Industries, Inc. | Carbamate functional polymers and oligomers and coating compositions containing same |
US6258898B1 (en) * | 1996-12-23 | 2001-07-10 | Basf Corporation | Amino resins functionalized with carbamate groups and coating compositions containing the same |
DE19839453A1 (en) | 1998-08-29 | 2000-03-02 | Basf Coatings Ag | Oligomeric and high molecular weight reaction products of allophanate esters with nucleophilic compounds and low molecular weight, oligomeric and high molecular weight compounds with allophanate side and / or end groups and their use |
US6150465A (en) | 1998-10-01 | 2000-11-21 | Basf Corporation | Powder slurry compositions with solid particulate carbamate resin component dispersed in liquid aminoplast resin carrier |
BR9914138A (en) * | 1998-12-14 | 2001-06-19 | Basf Corp | Powder composition of slurry containing particulate compounds with carbamate function |
AU2027300A (en) * | 1998-12-14 | 2000-07-03 | Basf Corporation | Particulate carbamate functional compounds and powder coatings comprising the same |
JP2002532607A (en) * | 1998-12-14 | 2002-10-02 | ビー・エイ・エス・エフ、コーポレーション | Granular carbamate-functional compound and powder coating containing said compound |
AU761107B2 (en) | 1999-03-17 | 2003-05-29 | E.I. Du Pont De Nemours And Company | High solids clear coating composition |
US6635314B1 (en) | 1999-03-17 | 2003-10-21 | E. I. Du Pont De Nemours And Company | High solids clear coating composition |
DE60001162T3 (en) | 1999-03-17 | 2007-02-15 | E.I. Dupont De Nemours And Co., Wilmington | SCRATCH-RESISTANT AND ACID-CORROSION-RESISTANT CLEAR LACQUER COMPOSITION WITH HIGH SOLIDS CONTENT |
KR20020007330A (en) | 1999-03-17 | 2002-01-26 | 메리 이. 보울러 | High solids acid etch resistant clear coating composition |
US6855779B1 (en) | 1999-03-17 | 2005-02-15 | E. I. Du Pont De Nemours And Company | High solid epoxy, melamine and isocyanate compositions |
US6624275B2 (en) | 2001-11-02 | 2003-09-23 | Basf Corporation | Water- and organic-soluble carbamate material |
US6624279B2 (en) | 1999-05-21 | 2003-09-23 | Basf Corporation | Water-soluble carbamate materials |
US6624241B2 (en) | 1999-05-21 | 2003-09-23 | Basf Corporation | Waterborne coating compositions containing materials dispersed with water-soluble carbamate materials |
US6362285B1 (en) | 1999-12-15 | 2002-03-26 | Basf Corporation | Curable coating compositions containing carbamate functional reactive additives |
US6303690B1 (en) | 1999-12-15 | 2001-10-16 | Basf Corporation | Cathodic electrocoat having a carbamate functional resin and a carbamate functional reactive additive |
US6380323B1 (en) | 1999-12-15 | 2002-04-30 | Basf Corporation | Electrocoat resin compositions containing carbamate functional resins having one or more quaternary ammonium groups and at least one carbamate functional reactive additive |
US6391968B1 (en) | 1999-12-15 | 2002-05-21 | Basf Corporation | Curable coating compositions containing carbamate functional polymers and carbamate functional reactive additives |
WO2001049658A1 (en) * | 1999-12-30 | 2001-07-12 | Eastman Chemical Company | Beta-hydroxy butenyl carbamate, functional oligomers and coatings therefrom |
US6541577B2 (en) * | 2000-12-06 | 2003-04-01 | Basf Corporation | Carbamate functional polymers and oligomers |
US20030050388A1 (en) * | 2001-09-06 | 2003-03-13 | Strickland Debra S. | Aqueous coating composition |
EP1456311B1 (en) * | 2001-12-17 | 2012-09-26 | BASF Coatings GmbH | Urethane polymers that reduce the effect of polylactone linkages |
DE60225328T2 (en) * | 2001-12-17 | 2009-02-26 | Basf Corp., Southfield | ASYMMETRIC DIISOCYANATE MONOMERS IN URETANOLPOLYMERS AND OLIGOMERS FOR CRYSTALLINE INITIALIZATION LIGHTING |
US6927271B2 (en) * | 2002-01-10 | 2005-08-09 | Basf Corporation | Hydroxyl and carbamate functional resins |
US6716953B2 (en) * | 2002-05-16 | 2004-04-06 | Ppg Industries Ohio, Inc. | Etherified carbamate crosslinking agents and their use in curable compositions, particularly film-forming compositions |
US7060357B2 (en) * | 2002-10-04 | 2006-06-13 | Basf Corporation | Powder coatings containing symmetrical additives |
US7232863B2 (en) | 2002-10-31 | 2007-06-19 | Basf Corporation | Functional addition polymers and a method for their preparation |
US20040087728A1 (en) * | 2002-10-31 | 2004-05-06 | Donald Campbell | Carbamate functional addition polymers and a method for their preparation |
US8686090B2 (en) * | 2003-12-10 | 2014-04-01 | Basf Coatings Gmbh | Use of urea crystals for non-polymeric coatings |
DE102004018543A1 (en) | 2004-04-14 | 2005-11-10 | Basf Ag | Carbamate-containing triazine derivatives |
US7858190B2 (en) * | 2005-09-15 | 2010-12-28 | Basf Coatings Gmbh | Thermosetting coating compositions with multiple cure mechanisms |
US20080124532A1 (en) * | 2006-11-29 | 2008-05-29 | Basf Corporation | Materials and oligomers in low voc coatings |
US20080293901A1 (en) * | 2007-05-25 | 2008-11-27 | Basf Corporation | Polymers and compounds prepared with alpha-methylene lactones, methods therefor, and coatings |
US20090053420A1 (en) * | 2007-08-20 | 2009-02-26 | Basf Corporation | Thermosetting coating compositions with multiple cure mechanisms |
DE102008041654A1 (en) | 2007-08-31 | 2009-03-05 | Basf Se | Preparing carbamate and allophanate group, useful e.g. in coating substrate e.g. wood, comprises reacting isocyanate monomer with monohydroxyalkylcarbamate in the presence of catalyst to form bond between urethane group and catalyst |
US20090074978A1 (en) * | 2007-09-13 | 2009-03-19 | Basf Corporation | Method of making carbamate functional materials |
WO2009086253A1 (en) * | 2007-12-27 | 2009-07-09 | E. I. Du Pont De Nemours And Company | Hydroxy alkyl isocyanurates |
JP4871951B2 (en) | 2008-12-26 | 2012-02-08 | 大島工業株式会社 | Heat resistant paint |
US8735507B2 (en) | 2010-06-16 | 2014-05-27 | Dow Global Technologies Llc | Crosslinkable composition and method of producing the same |
EP2397506B1 (en) | 2010-06-16 | 2017-09-27 | Dow Global Technologies Inc. | Ambient temperature curable isocyanate-free compositions for preparing crosslinked polyurethanes |
US8889818B2 (en) | 2010-06-16 | 2014-11-18 | Dow Global Technologies Llc | Crosslinkable composition and method of producing the same |
EP2949678B1 (en) | 2014-05-29 | 2016-12-28 | Dow Global Technologies Llc | Ambient cure, fast dry automotive refinish primer surfacer compositions and methods of use |
US10669429B2 (en) | 2015-07-22 | 2020-06-02 | Dow Global Technologies Llc | Ambient cure compositions for making coatings having humidity and corrosion resistance and methods of use |
US10131813B2 (en) | 2015-07-22 | 2018-11-20 | Dow Global Technologies Llc | Ambient cure compositions for making coatings having humidity and corrosion resistance and methods of use |
US11053191B2 (en) * | 2018-01-09 | 2021-07-06 | Ppg Industries Ohio, Inc. | Hydroxy functional alkyl carbamate crosslinkers |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL260847A (en) * | 1960-02-03 | |||
GB974900A (en) * | 1962-05-30 | 1964-11-11 | Ici Ltd | Isocyanurates and polymeric materials therefrom |
US3479328A (en) * | 1966-11-18 | 1969-11-18 | Ashland Oil Inc | Novel monomers and polymers |
US3674838A (en) * | 1969-06-05 | 1972-07-04 | Ashland Oil Inc | Vinyl carbamyloxy carboxylates |
DE2602352A1 (en) * | 1976-01-22 | 1977-07-28 | Bayer Ag | NETWORKABLE FAEDS |
FR2361450A1 (en) * | 1976-08-13 | 1978-03-10 | Basf Ag | HARDENABLE COATING MATERIAL |
US4126747A (en) * | 1976-12-28 | 1978-11-21 | Union Carbide Corporation | Carbamoyloxy acrylate compounds |
US4279833A (en) * | 1979-12-17 | 1981-07-21 | Ashland Chemical Company | Acrylic monomers containing carbamate functionality |
US4340497A (en) * | 1980-03-21 | 1982-07-20 | Union Carbide Corporation | (N-Substituted carbamoyloxy) alkanoyloxyalkyl acrylate esters |
US4543276A (en) * | 1983-03-28 | 1985-09-24 | American Cyanamid Company | Thermosetting polyurethane compositions |
US4588783A (en) * | 1983-12-16 | 1986-05-13 | Ppg Industries, Inc. | Amide-containing polyhydroxyethyl carbamates |
US4581430A (en) * | 1984-02-01 | 1986-04-08 | Armstrong World Industries, Inc. | Acrylate and methacrylate polymers and processes for preparing them |
US4758632A (en) * | 1984-02-17 | 1988-07-19 | American Cyanamid Company | Self-cross-linkable acrylic polymer containing hydroxyalkyl carbamate groups and coating compositions containing the same |
EP0152820B1 (en) * | 1984-02-17 | 1996-04-17 | Cytec Technology Corp. | Carbamate compounds, compositions and method of making the same |
US4820830A (en) * | 1987-03-02 | 1989-04-11 | King Industries, Inc. | Certain hydroxyalkyl carbamates, polymers and uses thereof |
EP0318088B1 (en) * | 1987-11-27 | 1993-07-21 | ENICHEM SYNTHESIS S.p.A. | Thermosetting liquid composition containing a polyepoxide |
DE4101158C2 (en) * | 1991-01-14 | 1994-06-23 | Dainippon Ink & Chemicals | Thermosetting reaction resin mixtures, use of the reaction resins according to the invention for the production of moldings and coatings |
-
1993
- 1993-04-30 US US08/056,514 patent/US5336566A/en not_active Expired - Lifetime
-
1994
- 1994-04-27 AU AU60729/94A patent/AU683046B2/en not_active Ceased
- 1994-04-28 EP EP19940106627 patent/EP0622387B1/en not_active Expired - Lifetime
- 1994-04-28 KR KR1019940009085A patent/KR100326622B1/en not_active IP Right Cessation
- 1994-04-28 ES ES94106627T patent/ES2120535T3/en not_active Expired - Lifetime
- 1994-04-28 JP JP09200794A patent/JP3506764B2/en not_active Expired - Lifetime
- 1994-04-28 DE DE1994611221 patent/DE69411221T2/en not_active Expired - Lifetime
- 1994-04-29 BR BR9401645A patent/BR9401645A/en not_active IP Right Cessation
- 1994-04-29 CA CA 2122534 patent/CA2122534C/en not_active Expired - Lifetime
- 1994-04-29 CN CN94105379A patent/CN1064054C/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
DE69411221T2 (en) | 1999-02-18 |
AU6072994A (en) | 1994-11-03 |
EP0622387B1 (en) | 1998-06-24 |
KR100326622B1 (en) | 2002-09-05 |
JPH0726059A (en) | 1995-01-27 |
EP0622387A1 (en) | 1994-11-02 |
AU683046B2 (en) | 1997-10-30 |
ES2120535T3 (en) | 1998-11-01 |
DE69411221D1 (en) | 1998-07-30 |
BR9401645A (en) | 1995-03-07 |
US5336566A (en) | 1994-08-09 |
JP3506764B2 (en) | 2004-03-15 |
CN1064054C (en) | 2001-04-04 |
CA2122534C (en) | 2003-03-11 |
CN1112148A (en) | 1995-11-22 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKEX | Expiry |
Effective date: 20140429 |