CA2266886A1 - Novel zirconium urethane catalysts - Google Patents

Novel zirconium urethane catalysts

Info

Publication number
CA2266886A1
CA2266886A1 CA002266886A CA2266886A CA2266886A1 CA 2266886 A1 CA2266886 A1 CA 2266886A1 CA 002266886 A CA002266886 A CA 002266886A CA 2266886 A CA2266886 A CA 2266886A CA 2266886 A1 CA2266886 A1 CA 2266886A1
Authority
CA
Canada
Prior art keywords
polyol
coating
adhesive film
group
polyisocyanate
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
Application number
CA002266886A
Other languages
French (fr)
Other versions
CA2266886C (en
Inventor
Werner J. Blank
Marie E. Picci
Zhiqiang Alex He
John J. Florio
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.)
King Industries Inc
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2266886A1 publication Critical patent/CA2266886A1/en
Application granted granted Critical
Publication of CA2266886C publication Critical patent/CA2266886C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
    • B01J31/2234—Beta-dicarbonyl ligands, e.g. acetylacetonates
    • 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
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/222—Catalysts containing metal compounds metal compounds not provided for in groups C08G18/225 - C08G18/26
    • 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
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
    • C08G18/6225—Polymers of esters of acrylic or methacrylic acid
    • 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
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
    • B01J2231/14—Other (co) polymerisation, e.g. of lactides, epoxides
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
    • B01J2531/48—Zirconium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
    • B01J2531/49—Hafnium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2540/00—Compositional aspects of coordination complexes or ligands in catalyst systems
    • B01J2540/20—Non-coordinating groups comprising halogens
    • B01J2540/22—Non-coordinating groups comprising halogens comprising fluorine, e.g. trifluoroacetate
    • B01J2540/225—Non-coordinating groups comprising halogens comprising fluorine, e.g. trifluoroacetate comprising perfluoroalkyl groups or moieties
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
    • B01J31/38—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of titanium, zirconium or hafnium

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Inorganic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Paints Or Removers (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

The present invention is directed to novel metal organocomplexes as catalysts for the reaction of compounds with isocyanate and hydroxy functional groups to form urethane and/or polyurethane and the proces employing such catalysts. More particularly, the present invention is directed to novel complexes of zirconium or hafnium with diketones or alkylacetoacetoates. These novel catalysts are useful for the production of urethanes and polyurethanes which are important in many industrial applications, such as: coatings, foams, adhesives, sealants, and reaction injection molding (RIM) plastics.

Claims (37)

1. An isocyanate-hydroxy reaction catalyst having the chemical structure:
Me(X1,X2,X3,X4) (I) wherein Me is zirconium (Zr) or hafnium (Hf) and X1, X2, X3, and X4, are the same or different and selected from the group consisting of a diketone having the structure:
R1COCH2COR2 (II) and an alylacetoacetate having the structure:
R1OCOCH2COR2 (III) wherein each of R1 and R2 is a branched or linear C1-C20 hydrocarbon and at least one of X1, X2, X3, and X4 is a diketone with structure (II) and wherein the total number of carbons in R1 + R2 in (II) and (III) is 4-21.
2. An isocyanate-hydroxy reaction catalyst according to Claim 1, wherein Me is zirconium.
3. An isocyanate-hydroxy reaction catalyst according to Claim 2, wherein the total number of carbons in R1 +
R2 is 5-18.
4. An isocyanate-hydroxy reaction catalyst composition comprising a mixture, wherein each component of the mixture is a catalyst of Claim 1, and wherein Me(X1, X2, X3, X4) of each component in the mixture is different.
5. An isocyanate-hydroxy reaction catalyst composition comprising a mixture of tetrakis-(2,4-pentanedionato) zirconium and a compound selected from the group consisting of a diketone having the structure:
R1COCH2COR2 (II) and and an alkylacetoacetate having the structure:
R1OCOCH2COR2 (III) wherein each of R1 and R2 is a branched or linear C1-C20 hydrocarbon and the total number of carbons in R1 + R2 is at least 4.
6. A composition comprising a polyol, a polyisocyanate and a catalyst of Claim 4.
7. A composition comprising a polyol, a polyisocyanate and a catalyst of Claim 5.
8. A composition according to Claim 6 wherein the polyol is selected from the group consisting hydroxy containing compounds having a molecular weight in the range of between 62 to 1,000,000 and the polyisocyanate is selected from the group consisting diisocyante, isocyanurate, allophanate, biuret compounds and polyurethane products derived from monomeric diisocyanato compounds.
9. A composition according to Claim 7 wherein the polyol is selected from the group consisting hydroxy containing compounds having a molecular weight in the range of between 62 to 1,000,000 and the polyisocyanate is selected from the group consisting diisocyante, isocyanurate, allophanate, biuret compounds and polyurethane products derived from monomeric diisocyanato compounds.
10. A composition according to Claim 8 wherein the molecular weight of the hydroxy containing compound is in the range of between 400 to 2,000.
11. A composition according to Claim 9 wherein the molecular weight of the hydroxy containing compound is in the range of between 400 to 2,000.
12. A composition according to Claim 8 wherein the polyol further contain carboxyl, amine, carbamate, amide and epoxy functional groups.
13. A composition according to Claim 9 wherein the polyol further contain carboxyl, amine, carbamate, amide and epoxy functional groups.
14. A process of preparing a coating or adhesive film by blending a composition according to Claim 6.
15. A process of preparing a coating or adhesive film by blending a composition according to Claim 7.
16. A process of preparing a coating or adhesive film by blending a composition according to Claim 8.
17. A process of preparing a coating or adhesive film by blending a composition according to Claim 9.
18. A process of preparing a coating or adhesive film by blending a composition according to Claim 10.
19. A process of preparing a coating or adhesive film by blending a composition according to Claim 11.
20. A process of preparing a coating or adhesive film by blending a composition according to Claim 12.
21. A process of preparing a coating or adhesive film by blending a composition according to Claim 13.
22. A coating or adhesive film prepared according to Claim 14.
23. A coating or adhesive film prepared according to Claim 15.
24. A coating or adhesive film prepared according to Claim 16.
25. A coating or adhesive film prepared according to Claim 17.
26. A coating or adhesive film prepared according to Claim 18.
27. A coating or adhesive film prepared according to Claim 19.
28. A coating or adhesive film prepared according to Claim 20.
29. A coating or adhesive film prepared according to Claim 21.
30. A coating or adhesive film prepared according to Claim 14 wherein the polyol is selected from the group consisting a polyester polyol, an alkyd polyol, an acrylic polyol, a polyether polyol or a mixture thereof and the polyisocyanate is selected from a group consisting of an aliphatic polyisocyanate.
31. A coating or adhesive film prepared according to Claim 15 wherein the polyol is selected from the group consisting a polyester polyol, an alkyd polyol, an acrylic polyol, a polyether polyol or a mixture thereof and the polyisocyanate is selected from a group consisting of an aliphatic polyisocyanate.
32. A coating or adhesive film prepared according to Claim 16 wherein the polyol is selected from the group consisting a polyester polyol, an alkyd polyol, an acrylic polyol, a polyether polyol or a mixture thereof and the polyisocyanate is selected from a group consisting of an aliphatic polyisocyanate.
33. A coating or adhesive film prepared according to Claim 17 wherein the polyol is selected from the group consisting a polyester polyol, an alkyd polyol, an acrylic polyol, a polyether polyol or a mixture thereof and the polyisocyanate is selected from a group consisting of an aliphatic polyisocyanate.
34. A coating or adhesive film prepared according to Claim 18 wherein the polyol is selected from the group consisting a polyester polyol, an alkyd polyol, an acrylic polyol, a polyether polyol or a mixture thereof and the polyisocyanate is selected from a group consisting of an aliphatic polyisocyanate.
35. A coating or adhesive film prepared according to Claim 19 wherein the polyol is selected from the group consisting a polyester polyol, an alkyd polyol, an acrylic polyol, a polyether polyol or a mixture thereof and the polyisocyanate is selected from a group consisting of an aliphatic polyisocyanate.
36. A coating or adhesive film prepared according to Claim 20 wherein the polyol is selected from the group consisting a polyester polyol, an alkyd polyol, an acrylic polyol, a polyether polyol or a mixture thereof and the polyisocyanate is selected from a group consisting of an aliphatic polyisocyanate.
37. A coating or adhesive film prepared according to Claim 21 wherein the polyol is selected from the group consisting a polyester polyol, an alkyd polyol, an acrylic polyol, a polyether polyol or a mixture thereof and the polyisocyanate is selected from a group consisting of an aliphatic polyisocyanate.
CA002266886A 1997-03-19 1998-03-16 Novel zirconium urethane catalysts Expired - Fee Related CA2266886C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/820,120 1997-03-19
US08/820,120 US5846897A (en) 1997-03-19 1997-03-19 Zirconium urethane catalysts
PCT/US1998/004997 WO1998041322A1 (en) 1997-03-19 1998-03-16 Novel zirconium urethane catalysts

Publications (2)

Publication Number Publication Date
CA2266886A1 true CA2266886A1 (en) 1998-09-24
CA2266886C CA2266886C (en) 2010-01-19

Family

ID=25229942

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002266886A Expired - Fee Related CA2266886C (en) 1997-03-19 1998-03-16 Novel zirconium urethane catalysts

Country Status (10)

Country Link
US (2) US5846897A (en)
EP (2) EP1021245A4 (en)
JP (1) JP4180119B2 (en)
KR (1) KR100524335B1 (en)
AT (1) ATE258825T1 (en)
AU (1) AU729058B2 (en)
CA (1) CA2266886C (en)
DE (2) DE69821536T2 (en)
ES (1) ES2215831T3 (en)
WO (1) WO1998041322A1 (en)

Families Citing this family (49)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030050425A1 (en) * 1996-03-01 2003-03-13 Spalding Sports Worldwide, Inc. Quick-cure game ball coating system
EP1116501A3 (en) * 1999-12-14 2005-09-28 Dunlop Sports Group Americas Inc. Method for coating golf balls with a dry-on-line clear polyurethane composition
GB0000569D0 (en) * 2000-01-12 2000-03-01 Ici Plc Organometallic compositions
CN1187388C (en) * 2000-05-26 2005-02-02 阿克佐诺贝尔股份有限公司 Photoactivatable coating compsn.
US7750109B2 (en) 2000-09-01 2010-07-06 Cyclics Corporation Use of a residual oligomer recyclate in the production of macrocyclic polyester oligomer
US7767781B2 (en) 2000-09-01 2010-08-03 Cyclics Corporation Preparation of low-acid polyalkylene terephthalate and preparation of macrocyclic polyester oligomer therefrom
GB0112901D0 (en) * 2001-05-29 2001-07-18 Ici Plc Organometallic compositions
CN1547577A (en) 2001-06-27 2004-11-17 Isolation, formulation, and shaping of macrocyclic oligoesters
GB0120743D0 (en) * 2001-08-25 2001-10-17 Ici Plc Catalysts and curable compositions
US6831138B2 (en) 2002-01-07 2004-12-14 Cyclics Corporation Polymer-containing organo-metal catalysts
CN1675004A (en) * 2002-08-13 2005-09-28 阿克佐诺贝尔国际涂料股份有限公司 Multilayer coating system comprising thiol-functional compounds
JP2006509070A (en) * 2002-12-04 2006-03-16 ジョンソン、マッセイ、パブリック、リミテッド、カンパニー Organometallic catalyst composition and polyurethane production process using said catalyst
DE10308106A1 (en) * 2003-02-26 2004-09-09 Bayer Aktiengesellschaft New 2K PUR systems
EP1460094B1 (en) * 2003-03-18 2007-01-31 Tosoh Corporation Catalyst composition for production of a polyurethane resin, and method for producing a polyurethane resin
US20050154109A1 (en) * 2004-01-12 2005-07-14 Minyu Li Floor finish with lightening agent
US20050154107A1 (en) * 2004-01-12 2005-07-14 Minyu Li Floor finish with lightening agent
US7655718B2 (en) * 2004-01-12 2010-02-02 Ecolab Inc. Polyurethane coating cure enhancement using zinc carbonate initiators
US20050153139A1 (en) * 2004-01-12 2005-07-14 Levitt Mark D. Aqueous polyurethane coating system containing zinc crosslinked acrylic dispersion
US20050154108A1 (en) * 2004-01-12 2005-07-14 Minyu Li Floor finish with lightening agent
US7527861B2 (en) * 2004-01-12 2009-05-05 Ecolab, Inc. Jobsite-renewable multilayer floor finish with enhanced hardening rate
WO2005070985A1 (en) * 2004-01-12 2005-08-04 Ecolab Inc. Polyurethane coating cure enhancement using zirconium carbonate
US8128998B2 (en) * 2004-01-12 2012-03-06 Ecolab Usa Inc. Polyurethane coating cure enhancement using ultrafine zinc oxide
JP2007519785A (en) * 2004-01-12 2007-07-19 イーコラブ インコーポレイティド Floor finish composition, laminate and floor treatment method
US20050154084A1 (en) * 2004-01-12 2005-07-14 Ecolab Inc. Floor finish with lightening agent
CN1333029C (en) * 2004-11-17 2007-08-22 上海市涂料研究所 Acetacetic acid alkyl ester metal chelate coating drier and production thereof
GB0513616D0 (en) * 2005-07-04 2005-08-10 Johnson Matthey Plc Novel zirconium compound, catalyst and its use for polyurethane manufacture
US20070010644A1 (en) * 2005-07-08 2007-01-11 Basf Corporation. Elastomeric urethane composition
US7691480B1 (en) 2005-07-08 2010-04-06 Basf Corporation Elastomeric urethane composition
MY146917A (en) * 2006-07-24 2012-10-15 Basf Se Low-emission polyurethane backing layer, spray polyurethane system for producing such a backing layer, and use of such a backing layer
EP2084198B1 (en) * 2006-11-20 2010-02-10 Akzo Nobel Coatings International BV Coating composition
PA8785001A1 (en) * 2007-06-18 2008-06-17 Johnson Matthey Plc STABLE COMPOUNDS IN WATER, CATALYZERS AND NEW CATALYZED REACTIONS
WO2009050115A1 (en) * 2007-10-17 2009-04-23 Basf Se Photolatent catalysts based on organometallic compounds
DE102008012085A1 (en) 2008-02-29 2009-09-10 Basf Coatings Ag Cathodic electrodeposition paint containing organometallic compound
EP2305727A1 (en) 2009-10-05 2011-04-06 Bayer MaterialScience AG New 2K PUR systems
JP5998660B2 (en) * 2012-06-08 2016-09-28 東ソー株式会社 Two-component polyurethane adhesive, laminate using the same, and protective sheet for solar cell
JP2013253192A (en) * 2012-06-08 2013-12-19 Tosoh Corp Two-component polyurethane-based adhesive, laminate using the same, and protective sheet for solar battery
JP5996985B2 (en) * 2012-09-24 2016-09-21 日東電工株式会社 Manufacturing method of pressure-sensitive adhesive sheet, and pressure-sensitive adhesive sheet obtained by the manufacturing method
CN105473640B (en) * 2013-08-15 2019-12-31 陶氏环球技术有限责任公司 Method for manufacturing polyurethane, polyurethane manufactured thereby, and coating composition comprising the polyurethane
ES2651140T3 (en) * 2013-12-10 2018-01-24 Covestro Deutschland Ag Polyisocyanates with iminooxadiacin dione groups
JP6264953B2 (en) * 2014-03-06 2018-01-24 凸版印刷株式会社 Lithium battery exterior materials
JP6264954B2 (en) * 2014-03-06 2018-01-24 凸版印刷株式会社 Lithium battery exterior materials
WO2015133368A1 (en) * 2014-03-06 2015-09-11 凸版印刷株式会社 Sheathing material for lithium batteries
US9376378B2 (en) 2014-05-08 2016-06-28 Basf Coatings Gmbh Method using zirconium catalyst for producing carbamate-functional materials
DE102015223948B3 (en) * 2015-12-01 2017-03-30 TE Connectivity Sensors Germany GmbH Substrate for a sensor arrangement for a resistance thermometer, sensor arrangement, resistance thermometer and method for producing such a substrate
US11306174B2 (en) 2017-05-08 2022-04-19 Ppg Industries Ohio, Inc. Curable film-forming compositions demonstrating decreased cure time with stable pot life
WO2019112707A1 (en) 2017-12-08 2019-06-13 Carbon, Inc. Shelf stable, low tin concentration, dual cure additive manufacturing resins
JP6428906B2 (en) * 2017-12-27 2018-11-28 凸版印刷株式会社 Lithium battery exterior materials
WO2020068720A1 (en) 2018-09-25 2020-04-02 Carbon, Inc. Dual cure resins for additive manufacturing
WO2020263480A1 (en) 2019-06-28 2020-12-30 Carbon, Inc. Dual cure additive manufacturing resins for the production of objects with mixed tensile properties

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE577999A (en) * 1958-04-25
GB890280A (en) * 1959-02-25 1962-02-28 Ici Ltd Improvements in or relating to the manufacture of foamed polyurethanes
GB908949A (en) * 1960-09-12 1962-10-24 Ici Ltd Improvements in or relating to the manufacture of polymers
GB1573071A (en) * 1977-02-10 1980-08-13 Mitsubishi Rayon Co Process for producing unsaturated carbocylic acid esters
FR2549037B1 (en) * 1983-07-11 1985-10-18 Saint Gobain Vitrage SAFETY SHEET GLAZING
US5306759A (en) * 1992-02-13 1994-04-26 Japan Synthetic Rubber Co., Ltd. Coating composition and process for manufacturing the same
DE4304679C2 (en) * 1992-02-17 1996-03-21 Mitsubishi Electric Corp Process for producing a thin dielectric layer of an oxide system using the CVD process
FI92897C (en) * 1993-07-20 1995-01-10 Planar International Oy Ltd Process for producing a layer structure for electroluminescence components

Also Published As

Publication number Publication date
WO1998041322A1 (en) 1998-09-24
EP1163956B8 (en) 2005-06-15
DE1021245T1 (en) 2001-04-19
US5846897A (en) 1998-12-08
EP1021245A4 (en) 2001-11-14
DE69821536D1 (en) 2004-03-11
EP1163956A1 (en) 2001-12-19
AU729058B2 (en) 2001-01-25
KR100524335B1 (en) 2005-10-28
JP4180119B2 (en) 2008-11-12
EP1163956B1 (en) 2004-02-04
JP2001524142A (en) 2001-11-27
CA2266886C (en) 2010-01-19
EP1021245A1 (en) 2000-07-26
KR20000076424A (en) 2000-12-26
DE69821536T2 (en) 2004-07-08
ATE258825T1 (en) 2004-02-15
US5965686A (en) 1999-10-12
ES2215831T3 (en) 2004-10-16
AU6555098A (en) 1998-10-12

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