AU732817B2 - Amine-blocked polyisocyanates and their use in one-component stoving compositions - Google Patents
Amine-blocked polyisocyanates and their use in one-component stoving compositions Download PDFInfo
- Publication number
- AU732817B2 AU732817B2 AU83064/98A AU8306498A AU732817B2 AU 732817 B2 AU732817 B2 AU 732817B2 AU 83064/98 A AU83064/98 A AU 83064/98A AU 8306498 A AU8306498 A AU 8306498A AU 732817 B2 AU732817 B2 AU 732817B2
- Authority
- AU
- Australia
- Prior art keywords
- polyisocyanate
- component
- blocked
- equivalent
- nco
- 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.)
- Ceased
Links
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 71
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 71
- 239000000203 mixture Substances 0.000 title claims abstract description 25
- 239000004922 lacquer Substances 0.000 claims abstract description 18
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 11
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 150000001412 amines Chemical class 0.000 claims abstract description 7
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 7
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 5
- 150000002429 hydrazines Chemical class 0.000 claims abstract description 5
- 239000012948 isocyanate Substances 0.000 claims abstract description 4
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 4
- 238000009835 boiling Methods 0.000 claims abstract description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 3
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical compound N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 claims abstract 2
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 42
- 239000003381 stabilizer Substances 0.000 claims description 15
- 229940043279 diisopropylamine Drugs 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 6
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- 150000005619 secondary aliphatic amines Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- -1 2,2,6,6-tetramethyl-piperidin-4-yl compound Chemical class 0.000 abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 238000000576 coating method Methods 0.000 description 18
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 13
- YXRKNIZYMIXSAD-UHFFFAOYSA-N 1,6-diisocyanatohexane Chemical compound O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O YXRKNIZYMIXSAD-UHFFFAOYSA-N 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 11
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 9
- 239000005058 Isophorone diisocyanate Substances 0.000 description 8
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 7
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 description 6
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000013638 trimer Substances 0.000 description 6
- 238000004566 IR spectroscopy Methods 0.000 description 4
- 239000002981 blocking agent Substances 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- WHIVNJATOVLWBW-PLNGDYQASA-N (nz)-n-butan-2-ylidenehydroxylamine Chemical compound CC\C(C)=N/O WHIVNJATOVLWBW-PLNGDYQASA-N 0.000 description 2
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- VUCWMAJEUOWLEY-UHFFFAOYSA-N 1-$l^{1}-azanylpiperidine Chemical compound [N]N1CCCCC1 VUCWMAJEUOWLEY-UHFFFAOYSA-N 0.000 description 1
- BTZVKSVLFLRBRE-UHFFFAOYSA-N 2-methoxypropyl acetate Chemical compound COC(C)COC(C)=O BTZVKSVLFLRBRE-UHFFFAOYSA-N 0.000 description 1
- HXXOPVULXOEHTK-UHFFFAOYSA-N 4-methyl-1,3-dioxol-2-one Chemical compound CC1=COC(=O)O1 HXXOPVULXOEHTK-UHFFFAOYSA-N 0.000 description 1
- 229920005789 ACRONAL® acrylic binder Polymers 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- FCSHMCFRCYZTRQ-UHFFFAOYSA-N N,N'-diphenylthiourea Chemical compound C=1C=CC=CC=1NC(=S)NC1=CC=CC=C1 FCSHMCFRCYZTRQ-UHFFFAOYSA-N 0.000 description 1
- ACFYSEDQILLVPH-UHFFFAOYSA-N NN.C(C)(C)NC(C)C Chemical compound NN.C(C)(C)NC(C)C ACFYSEDQILLVPH-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 150000005676 cyclic carbonates Chemical class 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009863 impact test Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000011527 polyurethane coating Substances 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000003678 scratch resistant effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/10—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- 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
- 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
- C08G18/3225—Polyamines
- C08G18/3228—Polyamines acyclic
- C08G18/3231—Hydrazine or derivatives thereof
-
- 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
- C08G18/80—Masked polyisocyanates
-
- 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
- C08G18/80—Masked polyisocyanates
- C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
- C08G18/8054—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/38
- C08G18/8058—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/38 with compounds of C08G18/3819
-
- 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
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
- C08G18/808—Monoamines
-
- 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
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)
- Paints Or Removers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Organic Insulating Materials (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19738497A DE19738497A1 (de) | 1997-09-03 | 1997-09-03 | Amin-blockierte Polyisocyanate |
| DE19738497 | 1997-09-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU8306498A AU8306498A (en) | 1999-03-18 |
| AU732817B2 true AU732817B2 (en) | 2001-05-03 |
Family
ID=7841065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU83064/98A Ceased AU732817B2 (en) | 1997-09-03 | 1998-09-03 | Amine-blocked polyisocyanates and their use in one-component stoving compositions |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5961878A (enExample) |
| EP (1) | EP0900814B1 (enExample) |
| JP (1) | JP4106135B2 (enExample) |
| KR (1) | KR100570587B1 (enExample) |
| AT (1) | ATE313579T1 (enExample) |
| AU (1) | AU732817B2 (enExample) |
| CA (1) | CA2246167C (enExample) |
| DE (2) | DE19738497A1 (enExample) |
| DK (1) | DK0900814T3 (enExample) |
| ES (1) | ES2255120T3 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10062411A1 (de) * | 2000-12-14 | 2002-06-20 | Bayer Ag | Blockierte Polyisocyanate auf HDI-Basis |
| DE10134238A1 (de) * | 2001-07-13 | 2003-01-23 | Bayer Ag | Wässrige und/oder wasserverdünnbare mit Diisopropylamin blockierte Polyisocyanat-Vernetzer und deren Verwendung |
| JP2003048949A (ja) * | 2001-08-03 | 2003-02-21 | Yokohama Rubber Co Ltd:The | 硬化性樹脂組成物 |
| DE10156897A1 (de) * | 2001-11-20 | 2003-05-28 | Bayer Ag | Mit epsilon-Caprolactam und DIPA bzw. 1,2,4-Triazol mischblockierte Polyisocyanate, deren Herstellung und Verwendung |
| DE10160570A1 (de) * | 2001-12-10 | 2003-06-18 | Bayer Ag | Anreagierte PUR-Bindemittel für Coil-Coating-Lacke |
| DE10201546A1 (de) * | 2002-01-17 | 2003-07-31 | Bayer Ag | Stabilisierte wässrige Polyurethan-Polyharnstoff Dispersionen |
| DE10226924A1 (de) * | 2002-06-17 | 2003-12-24 | Bayer Ag | Schlichtezusammensetzung |
| US6784243B2 (en) * | 2002-06-17 | 2004-08-31 | Bayer Aktiengesellschaft | Polyurethane-polyurea dispersions |
| DE10228730A1 (de) * | 2002-06-27 | 2004-01-22 | Bayer Ag | Zusammensetzung enthaltend ein blockiertes Polyisocyanat |
| US20040079477A1 (en) * | 2002-10-25 | 2004-04-29 | Lear Corporation | Method of making an interior trim part |
| DE10253482A1 (de) * | 2002-11-18 | 2004-06-03 | Bayer Ag | Verfestigungsstabile blockierte Polyisocyanate |
| DE10322911A1 (de) * | 2003-05-21 | 2004-12-16 | Bayer Materialscience Ag | Verfestigungsstabile blockierte Polyisocyanate |
| US7772307B2 (en) * | 2003-08-27 | 2010-08-10 | Great Eastern Resins Industrial Co., Ltd. | Water dispersible polyisocyanate composition and its uses |
| DE10348380A1 (de) * | 2003-10-17 | 2005-06-02 | Bayer Materialscience Ag | Mit sekundären Aminen blockierte Polyisocyanate mit Biuretstruktur |
| US20060089481A1 (en) * | 2004-10-21 | 2006-04-27 | Roesler Richard R | Blocked biuretized isocyanates |
| US20060089480A1 (en) * | 2004-10-21 | 2006-04-27 | Roesler Richard R | Biuretized isocyanates and blocked biuretized isocyanates |
| JP2012530801A (ja) * | 2009-06-18 | 2012-12-06 | ダウ グローバル テクノロジーズ エルエルシー | 色の安定なハロゲンフリー難燃性組成物 |
| EP4282894A1 (de) | 2022-05-25 | 2023-11-29 | Covestro Deutschland AG | Einkomponenten- einbrennsystem |
| EP4282893A1 (de) | 2022-05-25 | 2023-11-29 | Covestro Deutschland AG | Blockierte polyisocyanate |
| EP4559946A1 (de) | 2023-11-21 | 2025-05-28 | Covestro Deutschland AG | Blockierte polyisocyanate |
| CN119569993A (zh) * | 2024-12-04 | 2025-03-07 | 万华化学集团股份有限公司 | 一种改性hdi三聚体固化剂的制备方法及其应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3039824A1 (de) * | 1980-10-22 | 1982-05-27 | Bayer Ag, 5090 Leverkusen | Neue lackpolyisocyanate, ein verfahren zu ihrer herstellung, sowie ihre verwendung als isocyanatkomponente in hitzehaertbaren zweikomponenten-polyurethanlacken |
| US4495229A (en) * | 1982-06-08 | 1985-01-22 | Chemische Werke Huls A.G. | One-component, heat-curing polyurethane-coatings, stable in storage |
| DE3434881A1 (de) * | 1984-09-22 | 1986-04-03 | Hüls AG, 4370 Marl | Lagerstabile polyurethanharz-pulverlacke |
| DE3922767A1 (de) * | 1989-07-11 | 1991-01-17 | Bayer Ag | Hitzehaertbare gemische und ihre verwendung zur herstellung von beschichtungen auf hitzehaertbaren substraten |
| DE4015302A1 (de) * | 1990-05-12 | 1991-11-14 | Bayer Ag | Verfahren zur herstellung von aminen, die so erhaltenen amine und ihre verwendung als haerter fuer epoxidharze |
| DE4218184A1 (de) * | 1992-06-02 | 1993-12-09 | Bayer Ag | Wäßriges Bindemittelgemisch und seine Verwendung |
| DE4240480A1 (de) * | 1992-12-02 | 1994-08-25 | Bayer Ag | Organische Polyisocyanate mit zumindest teilweise blockierten Isocyanatgruppen |
| DE4339367A1 (de) * | 1993-11-18 | 1995-05-24 | Bayer Ag | Blockierte Polyisocyanate |
| DE19516400A1 (de) * | 1995-05-04 | 1996-11-07 | Bayer Ag | Blockierte Polyisocyanate und ihre Verwendung |
-
1997
- 1997-09-03 DE DE19738497A patent/DE19738497A1/de not_active Withdrawn
-
1998
- 1998-08-21 DE DE59813288T patent/DE59813288D1/de not_active Expired - Lifetime
- 1998-08-21 EP EP98115771A patent/EP0900814B1/de not_active Expired - Lifetime
- 1998-08-21 DK DK98115771T patent/DK0900814T3/da active
- 1998-08-21 AT AT98115771T patent/ATE313579T1/de active
- 1998-08-21 ES ES98115771T patent/ES2255120T3/es not_active Expired - Lifetime
- 1998-08-31 CA CA002246167A patent/CA2246167C/en not_active Expired - Fee Related
- 1998-09-01 JP JP26103498A patent/JP4106135B2/ja not_active Expired - Fee Related
- 1998-09-02 US US09/145,740 patent/US5961878A/en not_active Expired - Lifetime
- 1998-09-02 KR KR1019980036051A patent/KR100570587B1/ko not_active Expired - Fee Related
- 1998-09-03 AU AU83064/98A patent/AU732817B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| DE59813288D1 (de) | 2006-01-26 |
| US5961878A (en) | 1999-10-05 |
| CA2246167A1 (en) | 1999-03-03 |
| JPH11147928A (ja) | 1999-06-02 |
| EP0900814A1 (de) | 1999-03-10 |
| JP4106135B2 (ja) | 2008-06-25 |
| DK0900814T3 (da) | 2006-03-06 |
| EP0900814B1 (de) | 2005-12-21 |
| ATE313579T1 (de) | 2006-01-15 |
| DE19738497A1 (de) | 1999-03-04 |
| KR100570587B1 (ko) | 2006-07-25 |
| AU8306498A (en) | 1999-03-18 |
| ES2255120T3 (es) | 2006-06-16 |
| CA2246167C (en) | 2007-10-23 |
| KR19990029444A (ko) | 1999-04-26 |
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| FGA | Letters patent sealed or granted (standard patent) |