CA1276745C - Procede de preparation de polyisocyanate a groupement biuret - Google Patents
Procede de preparation de polyisocyanate a groupement biuretInfo
- Publication number
- CA1276745C CA1276745C CA000539085A CA539085A CA1276745C CA 1276745 C CA1276745 C CA 1276745C CA 000539085 A CA000539085 A CA 000539085A CA 539085 A CA539085 A CA 539085A CA 1276745 C CA1276745 C CA 1276745C
- Authority
- CA
- Canada
- Prior art keywords
- water
- weight
- acetate
- ethyl
- reaction
- 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 - Lifetime
Links
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 29
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 15
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 15
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 12
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 11
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims description 24
- -1 alkoxy-alkane carboxylates Chemical class 0.000 claims description 9
- ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 150000001983 dialkylethers Chemical class 0.000 claims description 3
- 150000004702 methyl esters Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 claims description 2
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 229920002396 Polyurea Polymers 0.000 abstract description 5
- 238000003860 storage Methods 0.000 abstract description 4
- 239000002244 precipitate Substances 0.000 abstract description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- AHBNSOZREBSAMG-UHFFFAOYSA-N 1,5-diisocyanato-2-methylpentane Chemical compound O=C=NCC(C)CCCN=C=O AHBNSOZREBSAMG-UHFFFAOYSA-N 0.000 description 1
- JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-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
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 206010038743 Restlessness Diseases 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003756 stirring Methods 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
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/7806—Nitrogen containing -N-C=0 groups
- C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
- C08G18/7831—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing biuret groups
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyurethanes Or Polyureas (AREA)
- Image Analysis (AREA)
- Color Printing (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8609947A FR2601007B1 (fr) | 1986-07-04 | 1986-07-04 | Procede de preparation de polyisocyanate a groupement biuret |
| FR8609947 | 1986-07-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1276745C true CA1276745C (fr) | 1990-11-20 |
Family
ID=9337215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000539085A Expired - Lifetime CA1276745C (fr) | 1986-07-04 | 1987-06-08 | Procede de preparation de polyisocyanate a groupement biuret |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4983762A (Direct) |
| EP (1) | EP0251952B1 (Direct) |
| JP (1) | JPS6322554A (Direct) |
| KR (1) | KR900008134B1 (Direct) |
| AT (1) | ATE81117T1 (Direct) |
| BR (1) | BR8703375A (Direct) |
| CA (1) | CA1276745C (Direct) |
| DE (1) | DE3781951T2 (Direct) |
| ES (1) | ES2033911T3 (Direct) |
| FR (1) | FR2601007B1 (Direct) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0766076B2 (ja) * | 1990-08-14 | 1995-07-19 | 動力炉・核燃料開発事業団 | マイクロ波による連続加熱脱硝装置 |
| DE4443885A1 (de) | 1994-12-09 | 1996-06-13 | Basf Ag | Verfahren zur Herstellung von Biuretgruppen enthaltenden Polyisocyanaten |
| DE19525474A1 (de) * | 1995-07-12 | 1997-01-16 | Basf Ag | Verfahren und Vorrichtung zur Herstellung von (cyclo)aliphatische Biuretgruppen enthaltenden Polyisocyananten |
| TWI530510B (zh) | 2012-11-01 | 2016-04-21 | 旭化成化學股份有限公司 | 聚異氰酸酯組成物及異氰酸酯聚合物組成物 |
| KR101493269B1 (ko) * | 2014-09-17 | 2015-02-16 | 애경화학 주식회사 | 저장성이 향상된 뷰렛 그룹 함유 알리파틱 폴리이소시아네이트의 제조방법 |
| WO2018070539A1 (ja) | 2016-10-14 | 2018-04-19 | 旭化成株式会社 | イソシアネート組成物及びイソシアネート重合体の製造方法 |
| TW201829375A (zh) | 2016-10-14 | 2018-08-16 | 日商旭化成股份有限公司 | 異氰酸酯組成物、異氰酸酯組成物的製造方法及異氰酸酯聚合物的製造方法 |
| WO2023080258A1 (ja) | 2021-11-08 | 2023-05-11 | 旭化成株式会社 | カルボニル化合物、カルボニル化合物の製造方法、イソシアネート化合物の製造方法、及びイソシアネート組成物 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4218390A (en) * | 1979-05-09 | 1980-08-19 | Brusilovsky Mikhail G | Method for preparing biuret-structure polyisocyanates |
| DE3403278A1 (de) * | 1984-01-31 | 1985-08-01 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von polyisocyanaten mit biuretstruktur |
-
1986
- 1986-07-04 FR FR8609947A patent/FR2601007B1/fr not_active Expired
-
1987
- 1987-06-08 CA CA000539085A patent/CA1276745C/fr not_active Expired - Lifetime
- 1987-07-01 ES ES198787420184T patent/ES2033911T3/es not_active Expired - Lifetime
- 1987-07-01 AT AT87420184T patent/ATE81117T1/de not_active IP Right Cessation
- 1987-07-01 EP EP87420184A patent/EP0251952B1/fr not_active Expired - Lifetime
- 1987-07-01 DE DE8787420184T patent/DE3781951T2/de not_active Expired - Fee Related
- 1987-07-02 JP JP62164131A patent/JPS6322554A/ja active Granted
- 1987-07-02 BR BR8703375A patent/BR8703375A/pt not_active IP Right Cessation
- 1987-07-04 KR KR1019870007156A patent/KR900008134B1/ko not_active Expired
-
1990
- 1990-04-23 US US07/512,604 patent/US4983762A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ATE81117T1 (de) | 1992-10-15 |
| FR2601007B1 (fr) | 1988-11-10 |
| KR900008134B1 (ko) | 1990-10-31 |
| FR2601007A1 (fr) | 1988-01-08 |
| EP0251952A3 (en) | 1988-09-07 |
| ES2033911T3 (es) | 1993-04-01 |
| DE3781951D1 (de) | 1992-11-05 |
| JPH0262545B2 (Direct) | 1990-12-26 |
| BR8703375A (pt) | 1988-03-15 |
| US4983762A (en) | 1991-01-08 |
| EP0251952A2 (fr) | 1988-01-07 |
| JPS6322554A (ja) | 1988-01-30 |
| DE3781951T2 (de) | 1993-03-11 |
| KR880001582A (ko) | 1988-04-25 |
| EP0251952B1 (fr) | 1992-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |