DE2353151A1 - 1-isocyanato-2-isocyanatomethyl-cyclopentan - Google Patents
1-isocyanato-2-isocyanatomethyl-cyclopentanInfo
- Publication number
- DE2353151A1 DE2353151A1 DE19732353151 DE2353151A DE2353151A1 DE 2353151 A1 DE2353151 A1 DE 2353151A1 DE 19732353151 DE19732353151 DE 19732353151 DE 2353151 A DE2353151 A DE 2353151A DE 2353151 A1 DE2353151 A1 DE 2353151A1
- Authority
- DE
- Germany
- Prior art keywords
- isocyanato
- cyclopentane
- isocyanatomethyl
- cyclopentylamine
- aminomethyl
- 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.)
- Pending
Links
- AFVMPODRAIDZQC-UHFFFAOYSA-N 1-isocyanato-2-(isocyanatomethyl)cyclopentane Chemical compound O=C=NCC1CCCC1N=C=O AFVMPODRAIDZQC-UHFFFAOYSA-N 0.000 title claims description 12
- SRGQQZYVZFJYHJ-UHFFFAOYSA-N 2-(aminomethyl)cyclopentan-1-amine Chemical compound NCC1CCCC1N SRGQQZYVZFJYHJ-UHFFFAOYSA-N 0.000 claims description 10
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 7
- RXGUIWHIADMCFC-UHFFFAOYSA-N 2-Methylpropyl 2-methylpropionate Chemical compound CC(C)COC(=O)C(C)C RXGUIWHIADMCFC-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- -1 amine hydrochloride Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 125000005442 diisocyanate group Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 239000004972 Polyurethane varnish Substances 0.000 description 2
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- FRMJZJUVLPFLAB-UHFFFAOYSA-N 2-iminocyclopentane-1-carbonitrile Chemical compound N=C1CCCC1C#N FRMJZJUVLPFLAB-UHFFFAOYSA-N 0.000 description 1
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- ZTAJGBTZFGMBRC-UHFFFAOYSA-N cyclopentylmethyl cyanate Chemical compound O(C#N)CC1CCCC1 ZTAJGBTZFGMBRC-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 238000001577 simple distillation 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
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7237512A FR2204189A5 (enExample) | 1972-10-23 | 1972-10-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2353151A1 true DE2353151A1 (de) | 1974-04-25 |
Family
ID=9106071
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732353151 Pending DE2353151A1 (de) | 1972-10-23 | 1973-10-23 | 1-isocyanato-2-isocyanatomethyl-cyclopentan |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3904665A (enExample) |
| JP (1) | JPS4993344A (enExample) |
| BE (1) | BE806365A (enExample) |
| DE (1) | DE2353151A1 (enExample) |
| FR (1) | FR2204189A5 (enExample) |
| GB (1) | GB1395470A (enExample) |
| IT (1) | IT998886B (enExample) |
| NL (1) | NL7314181A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0153561A1 (de) * | 1984-01-26 | 1985-09-04 | Bayer Ag | Neue Diisocyanate und ihre Verwendung zur Herstellung von Polyurethankunststoffen |
| EP0394058A1 (en) * | 1989-04-21 | 1990-10-24 | MITSUI TOATSU CHEMICALS, Inc. | Alicyclic diamines, alicyclic diisocyanates and polyisocyanato-isocyanurates and method for the preparation thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2953590A (en) * | 1953-04-11 | 1960-09-20 | Mobay Chemical Corp | Production of alkylene diisocyanates |
| DE1110859B (de) * | 1959-09-22 | 1961-07-13 | Bayer Ag | Verfahren zur Herstellung von hochmolekularen, vernetzten und gegebenenfalls verschaeumten Kunststoffen |
| DE1202785B (de) * | 1964-07-21 | 1965-10-14 | Scholven Chemie Ag | Verfahren zur Herstellung von 1-Isocyanato-3-(isocyanatomethyl)-3, 5, 5-trimethylcyclohexan |
-
1972
- 1972-10-23 FR FR7237512A patent/FR2204189A5/fr not_active Expired
-
1973
- 1973-10-15 NL NL7314181A patent/NL7314181A/xx unknown
- 1973-10-19 JP JP48117700A patent/JPS4993344A/ja active Pending
- 1973-10-19 US US408047A patent/US3904665A/en not_active Expired - Lifetime
- 1973-10-22 BE BE136939A patent/BE806365A/xx unknown
- 1973-10-23 IT IT30464/73A patent/IT998886B/it active
- 1973-10-23 DE DE19732353151 patent/DE2353151A1/de active Pending
- 1973-10-23 GB GB4909973A patent/GB1395470A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0153561A1 (de) * | 1984-01-26 | 1985-09-04 | Bayer Ag | Neue Diisocyanate und ihre Verwendung zur Herstellung von Polyurethankunststoffen |
| EP0394058A1 (en) * | 1989-04-21 | 1990-10-24 | MITSUI TOATSU CHEMICALS, Inc. | Alicyclic diamines, alicyclic diisocyanates and polyisocyanato-isocyanurates and method for the preparation thereof |
| US5126426A (en) * | 1989-04-21 | 1992-06-30 | Mitsui Toatsu Chemicals, Incorporated | Alicyclic diamines, alicyclic diisocyanates and polyisocyanato-isocyanurates and method for the preparation thereof |
| US5336749A (en) * | 1989-04-21 | 1994-08-09 | Mitsui Toatsu Chemicals, Incorporated | Alicyclic diamines, alicyclic diisocyanates and polyisocyanato-isocyanurates and method for the preparation thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| BE806365A (fr) | 1974-04-22 |
| FR2204189A5 (enExample) | 1974-05-17 |
| US3904665A (en) | 1975-09-09 |
| JPS4993344A (enExample) | 1974-09-05 |
| NL7314181A (enExample) | 1974-04-25 |
| GB1395470A (en) | 1975-05-29 |
| IT998886B (it) | 1976-02-20 |
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