DE2550156C2 - Verfahren zur Herstellung von Polyisocyanatgemischen mit blockierten Isocyanatgruppen und ihre Verwendung in Polyuretan-Einbrennlacken - Google Patents
Verfahren zur Herstellung von Polyisocyanatgemischen mit blockierten Isocyanatgruppen und ihre Verwendung in Polyuretan-EinbrennlackenInfo
- Publication number
- DE2550156C2 DE2550156C2 DE2550156A DE2550156A DE2550156C2 DE 2550156 C2 DE2550156 C2 DE 2550156C2 DE 2550156 A DE2550156 A DE 2550156A DE 2550156 A DE2550156 A DE 2550156A DE 2550156 C2 DE2550156 C2 DE 2550156C2
- Authority
- DE
- Germany
- Prior art keywords
- weight
- isocyanate
- groups
- reaction
- blocked
- 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.)
- Expired
Links
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- 238000000034 method Methods 0.000 title claims description 21
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- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 210000003298 dental enamel Anatomy 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 32
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- 239000002904 solvent Substances 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 3
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 21
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
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- 235000014113 dietary fatty acids Nutrition 0.000 description 3
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- 150000004665 fatty acids Chemical class 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
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- 239000004721 Polyphenylene oxide Substances 0.000 description 2
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- 125000003118 aryl group Chemical group 0.000 description 2
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- 238000004132 cross linking Methods 0.000 description 1
- VKONPUDBRVKQLM-UHFFFAOYSA-N cyclohexane-1,4-diol Chemical compound OC1CCC(O)CC1 VKONPUDBRVKQLM-UHFFFAOYSA-N 0.000 description 1
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- JBSLOWBPDRZSMB-BQYQJAHWSA-N dibutyl (e)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C\C(=O)OCCCC JBSLOWBPDRZSMB-BQYQJAHWSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- PYBNTRWJKQJDRE-UHFFFAOYSA-L dodecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O PYBNTRWJKQJDRE-UHFFFAOYSA-L 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- PRWXGRGLHYDWPS-UHFFFAOYSA-L sodium malonate Chemical compound [Na+].[Na+].[O-]C(=O)CC([O-])=O PRWXGRGLHYDWPS-UHFFFAOYSA-L 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 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
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
- C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
- C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
- C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203
- C08G18/8032—Masked aliphatic or cycloaliphatic polyisocyanates not provided for in one single of the groups C08G18/8016 and C08G18/8025
-
- 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
- C08G18/8093—Compounds containing active methylene groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paints Or Removers (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2550156A DE2550156C2 (de) | 1975-11-07 | 1975-11-07 | Verfahren zur Herstellung von Polyisocyanatgemischen mit blockierten Isocyanatgruppen und ihre Verwendung in Polyuretan-Einbrennlacken |
| US05/734,832 US4101530A (en) | 1975-11-07 | 1976-10-22 | Process for the production of polyisocyanate mixtures containing blocked isocyanate groups |
| GB45475/76A GB1498615A (en) | 1975-11-07 | 1976-11-02 | Process for the production of polyisocyanate mixtures containing blocked isocyanate groups |
| SE7612309A SE7612309L (sv) | 1975-11-07 | 1976-11-04 | Sett att framstella polyisocyanatblandningar med blockerade isocyanatgrupper. |
| FR7633511A FR2330731A1 (fr) | 1975-11-07 | 1976-11-05 | Procede de preparation de melanges de polyisocyanates a groupes isocyanate bloques, solubles dans les solvants pour peintures ou vernis a cuire au four |
| JP51132529A JPS5944310B2 (ja) | 1975-11-07 | 1976-11-05 | ブロツクトイソシアネ−ト基を有するポリイソシアネ−ト混合物の製造方法 |
| IT52044/76A IT1066672B (it) | 1975-11-07 | 1976-11-05 | Procedimento per produrre miscugli di poliisocianati |
| ES453056A ES453056A1 (es) | 1975-11-07 | 1976-11-05 | Procedimiento para la obtencion de mezclas de poliisocianto con grupos de isocianatos bloqueados. |
| BE172114A BE848036A (fr) | 1975-11-07 | 1976-11-05 | Procede de preparation de melanges de polyisocyanates a groupes isocyanate bloques, solubles dans les solvants pour peintures ou vernis a cuire au four |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2550156A DE2550156C2 (de) | 1975-11-07 | 1975-11-07 | Verfahren zur Herstellung von Polyisocyanatgemischen mit blockierten Isocyanatgruppen und ihre Verwendung in Polyuretan-Einbrennlacken |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2550156A1 DE2550156A1 (de) | 1977-05-18 |
| DE2550156C2 true DE2550156C2 (de) | 1983-12-15 |
Family
ID=5961233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2550156A Expired DE2550156C2 (de) | 1975-11-07 | 1975-11-07 | Verfahren zur Herstellung von Polyisocyanatgemischen mit blockierten Isocyanatgruppen und ihre Verwendung in Polyuretan-Einbrennlacken |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4101530A (enExample) |
| JP (1) | JPS5944310B2 (enExample) |
| BE (1) | BE848036A (enExample) |
| DE (1) | DE2550156C2 (enExample) |
| ES (1) | ES453056A1 (enExample) |
| FR (1) | FR2330731A1 (enExample) |
| GB (1) | GB1498615A (enExample) |
| IT (1) | IT1066672B (enExample) |
| SE (1) | SE7612309L (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3004876A1 (de) * | 1980-02-09 | 1981-08-20 | Chemische Werke Hüls AG, 4370 Marl | Blockierte polyisocyanate mit hoher reaktionsfaehigkeit, ihre herstellung und verwendung |
| DE3030554A1 (de) * | 1980-08-13 | 1982-03-25 | Chemische Werke Hüls AG, 4370 Marl | Einbrennlacke |
| DE3046409A1 (de) | 1980-12-10 | 1982-07-15 | Bayer Ag, 5090 Leverkusen | Beschichtungsmittel und ein verfahren zur herstellung von ueberzuegen |
| US4439593A (en) * | 1983-05-26 | 1984-03-27 | Mobay Chemical Corporation | Polyurethane compositions with improved storage stability |
| DE3322721A1 (de) * | 1983-06-24 | 1985-01-03 | Chemische Werke Hüls AG, 4370 Marl | Einkomponenten-einbrennlacke |
| US4518522A (en) * | 1983-09-19 | 1985-05-21 | Mobay Chemical Corporation | Blocked polyisocyanates with improved storage stability |
| DE3337394A1 (de) * | 1983-10-14 | 1985-05-02 | Herberts Gmbh, 5600 Wuppertal | Steinschlagschutzschicht-lack, verfahren zu seiner herstellung und dessen verwendung |
| DE3337395A1 (de) * | 1983-10-14 | 1985-05-02 | Herberts Gmbh, 5600 Wuppertal | Nichtwaessriger lack mit hohem steinschlagschutz, verfahren zu seiner herstellung und dessen verwendung |
| JPS61211322A (ja) * | 1985-03-15 | 1986-09-19 | Asahi Denka Kogyo Kk | ポリウレタン組成物 |
| DE3606513C2 (de) * | 1986-02-28 | 1998-05-07 | Basf Coatings Ag | Dispersionen von vernetzten Polymermikroteilchen in wäßrigen Medien und Verfahren zur Herstellung dieser Dispersionen |
| US4677180A (en) * | 1986-07-16 | 1987-06-30 | Mobay Corporation | Polyurethane compositions with improved storage stability |
| CH669955A5 (enExample) * | 1986-08-04 | 1989-04-28 | Sika Ag | |
| DE3734916A1 (de) * | 1987-10-15 | 1989-04-27 | Hoechst Ag | Haertungskomponente fuer kunstharze, diese enthaltende haertbare mischungen sowie deren verwendung |
| US5221707A (en) * | 1989-11-30 | 1993-06-22 | Gencorp Inc. | Coating blend compositions |
| DE4022660A1 (de) * | 1990-07-17 | 1992-01-23 | Bayer Ag | Bindemittelkombination, ihre verwendung in einbrennlacken und ein verfahren zur herstellung von ueberzuegen |
| US5064896A (en) * | 1990-08-08 | 1991-11-12 | Tanner Chemical Company, Inc. | Adhesive compositions |
| DE4100204A1 (de) * | 1991-01-05 | 1992-07-09 | Bayer Ag | Beschichtungsmittel und seine verwendung zur herstellung von beschichtungen |
| DE4114800A1 (de) * | 1991-05-07 | 1992-11-12 | Bayer Ag | Neue polyesterpolyole sowie deren verwendung als haftvermittler fuer polymersysteme und als polymerweichmacher |
| US5488092A (en) * | 1994-04-26 | 1996-01-30 | Gencorp Inc. | Low VOC, primerless, polyurethane compostions |
| DE19534624A1 (de) * | 1995-09-18 | 1997-03-20 | Bayer Ag | Allophanatgruppen aufweisende Polyisocyanate auf Basis Diphenylmethandiisocyanat mit überwiegend oder vollständig blockierten Isocyanatgruppen |
| JP3712295B2 (ja) * | 1996-04-12 | 2005-11-02 | 旭化成ケミカルズ株式会社 | ブロックポリイソシアネート組成物及びそれを用いた一液性熱硬化組成物 |
| DE10003319A1 (de) | 2000-01-27 | 2001-08-02 | Bayer Ag | Neue Bindemittelkombinationen für wetterbeständige Coil-Coating-Beschichtungen |
| US8445555B2 (en) * | 2006-07-13 | 2013-05-21 | Air Products And Chemicals, Inc. | Stabilized carbanions as trimerization catalysts |
| DE102008063085A1 (de) | 2008-12-24 | 2010-07-01 | Basf Coatings Ag | Lackzusammensetzung |
| US11798799B2 (en) * | 2021-08-09 | 2023-10-24 | Applied Materials, Inc. | Ultraviolet and ozone clean system |
| EP4289878A1 (de) | 2022-06-08 | 2023-12-13 | Evonik Operations GmbH | Ein-komponentensystem umfassend blockierte polyurethanprepolymere |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE666023A (enExample) * | 1964-07-21 | |||
| DE1795417A1 (de) * | 1968-09-27 | 1972-01-05 | Bayer Ag | Verfahren zur Herstellung physiologisch unbedenklicher,aliphatischer Polyisocyanate |
| JPS5420560B2 (enExample) * | 1971-11-20 | 1979-07-24 | ||
| DE2200342A1 (de) * | 1972-01-05 | 1973-07-12 | Basf Ag | Verfahren zur herstellung von ueberzuegen durch auftragen pulverfoermiger ueberzugsmittel |
| GB1434445A (en) * | 1973-06-27 | 1976-05-05 | Bayer Ag | Physiologically harmless polyisocyanate solutions |
| DE2436872C3 (de) * | 1974-07-31 | 1980-04-10 | Basf Ag, 6700 Ludwigshafen | 1 -(Bis-äthoxycarbonyl)-acetylamino-S-bis-äthoxycarbonyO-acetyl-aminomethyl-333-trimethyl-cyclohexan |
-
1975
- 1975-11-07 DE DE2550156A patent/DE2550156C2/de not_active Expired
-
1976
- 1976-10-22 US US05/734,832 patent/US4101530A/en not_active Expired - Lifetime
- 1976-11-02 GB GB45475/76A patent/GB1498615A/en not_active Expired
- 1976-11-04 SE SE7612309A patent/SE7612309L/xx unknown
- 1976-11-05 FR FR7633511A patent/FR2330731A1/fr active Granted
- 1976-11-05 JP JP51132529A patent/JPS5944310B2/ja not_active Expired
- 1976-11-05 IT IT52044/76A patent/IT1066672B/it active
- 1976-11-05 ES ES453056A patent/ES453056A1/es not_active Expired
- 1976-11-05 BE BE172114A patent/BE848036A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2330731B1 (enExample) | 1983-10-28 |
| BE848036A (fr) | 1977-05-05 |
| ES453056A1 (es) | 1977-11-01 |
| FR2330731A1 (fr) | 1977-06-03 |
| JPS5259139A (en) | 1977-05-16 |
| US4101530A (en) | 1978-07-18 |
| GB1498615A (en) | 1978-01-25 |
| DE2550156A1 (de) | 1977-05-18 |
| IT1066672B (it) | 1985-03-12 |
| JPS5944310B2 (ja) | 1984-10-29 |
| SE7612309L (sv) | 1977-05-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: C07C125/07 |
|
| 8126 | Change of the secondary classification |
Ipc: C08G 18/00 |
|
| 8126 | Change of the secondary classification |
Free format text: C08G 18/80 C09D 3/72 C09D 3/727 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |