DE2356213C2 - Durch Ketimingruppen terminierte Prepolymere und Verfahren zu ihrer Herstellung - Google Patents
Durch Ketimingruppen terminierte Prepolymere und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2356213C2 DE2356213C2 DE19732356213 DE2356213A DE2356213C2 DE 2356213 C2 DE2356213 C2 DE 2356213C2 DE 19732356213 DE19732356213 DE 19732356213 DE 2356213 A DE2356213 A DE 2356213A DE 2356213 C2 DE2356213 C2 DE 2356213C2
- Authority
- DE
- Germany
- Prior art keywords
- stage
- reaction
- cooling
- aliphatic
- adduct
- 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
- 150000004658 ketimines Chemical group 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 23
- 150000002513 isocyanates Chemical class 0.000 claims description 23
- 125000001931 aliphatic group Chemical group 0.000 claims description 16
- 150000001875 compounds Chemical group 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 238000001816 cooling Methods 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 9
- 229920001451 polypropylene glycol Polymers 0.000 claims description 7
- 125000005442 diisocyanate group Chemical group 0.000 claims description 6
- 150000003997 cyclic ketones Chemical class 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 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 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- -1 aliphatic aldehydes Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- XPZBNIUWMDJFPW-UHFFFAOYSA-N 2,2,3-trimethylcyclohexan-1-one Chemical compound CC1CCCC(=O)C1(C)C XPZBNIUWMDJFPW-UHFFFAOYSA-N 0.000 description 1
- AVFZQHWFGFKQIG-UHFFFAOYSA-N 2,2,3-trimethylcyclopentan-1-one Chemical compound CC1CCC(=O)C1(C)C AVFZQHWFGFKQIG-UHFFFAOYSA-N 0.000 description 1
- VZDIRINETBAVAV-UHFFFAOYSA-N 2,4-diisocyanato-1-methylcyclohexane Chemical compound CC1CCC(N=C=O)CC1N=C=O VZDIRINETBAVAV-UHFFFAOYSA-N 0.000 description 1
- SUTWPJHCRAITLU-UHFFFAOYSA-N 6-aminohexan-1-ol Chemical compound NCCCCCCO SUTWPJHCRAITLU-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001240 enamine group Chemical group 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000013008 moisture curing Methods 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/3271—Hydroxyamines
- C08G18/3296—Hydroxyamines being in latent form
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)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732356213 DE2356213C2 (de) | 1973-11-10 | 1973-11-10 | Durch Ketimingruppen terminierte Prepolymere und Verfahren zu ihrer Herstellung |
| SU742061351A SU743583A3 (ru) | 1973-11-10 | 1974-09-18 | Способ получени полимерного материала |
| US05/520,356 US3941753A (en) | 1971-04-06 | 1974-11-01 | Prepolymers of polyisocyanates with hydroxy-enamines or hydroxy-ketimines |
| AT890474A AT339606B (de) | 1973-11-10 | 1974-11-06 | Verfahren zur herstellung von neuen, ketimingruppen enthaltenden prapolymeren |
| SE7414020A SE421523B (sv) | 1973-11-10 | 1974-11-07 | Nya prepolymerer, innehallande ketimingrupper, till anvendning som aminavspeljkande foreningar vid framstellning av polyuretaner |
| JP49128497A JPS5811894B2 (ja) | 1973-11-10 | 1974-11-07 | ケチミンキオユウスル シンキプレポリマ−ノ セイホウ |
| NL7414636A NL7414636A (nl) | 1973-11-10 | 1974-11-08 | Werkwijze ter bereiding van ketimine-groepen- -bevattende prepolymeren. |
| FR7437062A FR2257620B2 (enrdf_load_stackoverflow) | 1973-11-10 | 1974-11-08 | |
| GB4848474A GB1486790A (en) | 1973-11-10 | 1974-11-08 | Compounds derivable from polyisocyanates and compounds containing ketimine and hydroxyl group |
| BE150350A BE822013A (fr) | 1973-11-10 | 1974-11-08 | Prepolymeres comprenant des groupes cetimines et leur preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732356213 DE2356213C2 (de) | 1973-11-10 | 1973-11-10 | Durch Ketimingruppen terminierte Prepolymere und Verfahren zu ihrer Herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2356213A1 DE2356213A1 (de) | 1975-05-15 |
| DE2356213C2 true DE2356213C2 (de) | 1986-11-13 |
Family
ID=5897734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732356213 Expired DE2356213C2 (de) | 1971-04-06 | 1973-11-10 | Durch Ketimingruppen terminierte Prepolymere und Verfahren zu ihrer Herstellung |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5811894B2 (enrdf_load_stackoverflow) |
| AT (1) | AT339606B (enrdf_load_stackoverflow) |
| BE (1) | BE822013A (enrdf_load_stackoverflow) |
| DE (1) | DE2356213C2 (enrdf_load_stackoverflow) |
| FR (1) | FR2257620B2 (enrdf_load_stackoverflow) |
| GB (1) | GB1486790A (enrdf_load_stackoverflow) |
| NL (1) | NL7414636A (enrdf_load_stackoverflow) |
| SE (1) | SE421523B (enrdf_load_stackoverflow) |
| SU (1) | SU743583A3 (enrdf_load_stackoverflow) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2546536A1 (de) | 1975-10-17 | 1977-04-28 | Bayer Ag | Hochmolekulare polyamine und verfahren zu ihrer herstellung |
| DE2651479C2 (de) * | 1976-11-11 | 1986-03-20 | Schering AG, 1000 Berlin und 4709 Bergkamen | Elastisches Klebemittel |
| JPS59161292U (ja) * | 1983-03-24 | 1984-10-29 | スタンレー電気株式会社 | Ｅｌ素子用取出し電極 |
| DE4311901A1 (de) * | 1993-04-10 | 1994-10-13 | Huels Chemische Werke Ag | Neue Azeomethine, ein Verfahren zu ihrer Herstellung sowie deren Verwendung |
| US20140275464A1 (en) * | 2005-09-15 | 2014-09-18 | The Government Of The United States Of America, As Represented By The Secretary Of The Navy | Polyenureas and method of making the same |
| US8735526B2 (en) | 2005-09-15 | 2014-05-27 | The United States Of America, As Represented By The Secretary Of The Navy | Polyenureas and method of making the same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2116882C3 (de) * | 1971-04-06 | 1985-05-15 | Schering AG, 1000 Berlin und 4709 Bergkamen | Enaminverbindungen und deren Herstellung |
-
1973
- 1973-11-10 DE DE19732356213 patent/DE2356213C2/de not_active Expired
-
1974
- 1974-09-18 SU SU742061351A patent/SU743583A3/ru active
- 1974-11-06 AT AT890474A patent/AT339606B/de not_active IP Right Cessation
- 1974-11-07 SE SE7414020A patent/SE421523B/xx not_active IP Right Cessation
- 1974-11-07 JP JP49128497A patent/JPS5811894B2/ja not_active Expired
- 1974-11-08 FR FR7437062A patent/FR2257620B2/fr not_active Expired
- 1974-11-08 BE BE150350A patent/BE822013A/xx not_active IP Right Cessation
- 1974-11-08 GB GB4848474A patent/GB1486790A/en not_active Expired
- 1974-11-08 NL NL7414636A patent/NL7414636A/xx active Search and Examination
Also Published As
| Publication number | Publication date |
|---|---|
| AT339606B (de) | 1977-10-25 |
| SE7414020L (enrdf_load_stackoverflow) | 1975-05-12 |
| SE421523B (sv) | 1982-01-04 |
| NL7414636A (nl) | 1975-05-13 |
| JPS5811894B2 (ja) | 1983-03-05 |
| GB1486790A (en) | 1977-09-21 |
| FR2257620A2 (enrdf_load_stackoverflow) | 1975-08-08 |
| ATA890474A (de) | 1977-02-15 |
| DE2356213A1 (de) | 1975-05-15 |
| BE822013A (fr) | 1975-05-09 |
| FR2257620B2 (enrdf_load_stackoverflow) | 1978-06-23 |
| JPS5079599A (enrdf_load_stackoverflow) | 1975-06-28 |
| SU743583A3 (ru) | 1980-06-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8162 | Independent application | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |