DE2726749A1 - Verfahren zur herstellung von 2,4,6- triketohexahydrotriazinen - Google Patents
Verfahren zur herstellung von 2,4,6- triketohexahydrotriazinenInfo
- Publication number
- DE2726749A1 DE2726749A1 DE19772726749 DE2726749A DE2726749A1 DE 2726749 A1 DE2726749 A1 DE 2726749A1 DE 19772726749 DE19772726749 DE 19772726749 DE 2726749 A DE2726749 A DE 2726749A DE 2726749 A1 DE2726749 A1 DE 2726749A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- isocyanate
- aryl
- isocyanates
- groups
- 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.)
- Granted
Links
- 239000012948 isocyanate Substances 0.000 title claims abstract description 27
- 239000003054 catalyst Substances 0.000 title claims abstract description 22
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 22
- 230000003197 catalytic effect Effects 0.000 title claims abstract description 5
- 150000001412 amines Chemical class 0.000 title abstract description 4
- 150000002118 epoxides Chemical class 0.000 title abstract description 4
- 239000000543 intermediate Substances 0.000 title abstract description 3
- 239000011248 coating agent Substances 0.000 title abstract 2
- 238000000576 coating method Methods 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 9
- 239000004593 Epoxy Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 239000010409 thin film Substances 0.000 claims abstract description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
- 238000005829 trimerization reaction Methods 0.000 claims description 11
- -1 alkyl radical Chemical class 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000000178 monomer Substances 0.000 abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 229910052717 sulfur Inorganic materials 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 5
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 5
- 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 5
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 4
- 239000005056 polyisocyanate Substances 0.000 description 4
- 229920001228 polyisocyanate Polymers 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 3
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- JXHQHIGDDYSAJH-UHFFFAOYSA-N 1-isocyanato-1-(isocyanatomethyl)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(CN=C=O)(N=C=O)C1 JXHQHIGDDYSAJH-UHFFFAOYSA-N 0.000 description 2
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 2
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229960002887 deanol Drugs 0.000 description 2
- 239000012972 dimethylethanolamine Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- DDPRYTUJYNYJKV-UHFFFAOYSA-N 1,4-diethylpiperazine Chemical compound CCN1CCN(CC)CC1 DDPRYTUJYNYJKV-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- FWWWRCRHNMOYQY-UHFFFAOYSA-N 1,5-diisocyanato-2,4-dimethylbenzene Chemical compound CC1=CC(C)=C(N=C=O)C=C1N=C=O FWWWRCRHNMOYQY-UHFFFAOYSA-N 0.000 description 1
- VAGFVLBAZGSOAC-UHFFFAOYSA-N 1,6,11-triisocyanatoundecane Chemical compound O=C=NCCCCCC(N=C=O)CCCCCN=C=O VAGFVLBAZGSOAC-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- BCMYXYHEMGPZJN-UHFFFAOYSA-N 1-chloro-2-isocyanatoethane Chemical compound ClCCN=C=O BCMYXYHEMGPZJN-UHFFFAOYSA-N 0.000 description 1
- MKMMDUNWJMDPHL-UHFFFAOYSA-N 1-chloro-6-isocyanatohexane Chemical compound ClCCCCCCN=C=O MKMMDUNWJMDPHL-UHFFFAOYSA-N 0.000 description 1
- JZRKHDXSWFGREU-UHFFFAOYSA-N 1-isocyanato-4-methylpentane Chemical compound CC(C)CCCN=C=O JZRKHDXSWFGREU-UHFFFAOYSA-N 0.000 description 1
- YIDSTEJLDQMWBR-UHFFFAOYSA-N 1-isocyanatododecane Chemical compound CCCCCCCCCCCCN=C=O YIDSTEJLDQMWBR-UHFFFAOYSA-N 0.000 description 1
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 1
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 description 1
- QHTUMQYGZQYEOZ-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)ethanol Chemical compound CN1CCN(CCO)CC1 QHTUMQYGZQYEOZ-UHFFFAOYSA-N 0.000 description 1
- LKMJVFRMDSNFRT-UHFFFAOYSA-N 2-(methoxymethyl)oxirane Chemical compound COCC1CO1 LKMJVFRMDSNFRT-UHFFFAOYSA-N 0.000 description 1
- CWNOEVURTVLUNV-UHFFFAOYSA-N 2-(propoxymethyl)oxirane Chemical compound CCCOCC1CO1 CWNOEVURTVLUNV-UHFFFAOYSA-N 0.000 description 1
- HACRKYQRZABURO-UHFFFAOYSA-N 2-phenylethyl isocyanate Chemical compound O=C=NCCC1=CC=CC=C1 HACRKYQRZABURO-UHFFFAOYSA-N 0.000 description 1
- QNSNSOWOZZVZDQ-UHFFFAOYSA-N 3-isocyanatopropanenitrile Chemical compound O=C=NCCC#N QNSNSOWOZZVZDQ-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
- ASZFCDOTGITCJI-UHFFFAOYSA-N 6-oxabicyclo[3.1.0]hex-2-ene Chemical compound C1C=CC2OC12 ASZFCDOTGITCJI-UHFFFAOYSA-N 0.000 description 1
- HBOZYYOWOFRMEK-UHFFFAOYSA-N C(CC)N=C=O.C(CC)OCCC Chemical compound C(CC)N=C=O.C(CC)OCCC HBOZYYOWOFRMEK-UHFFFAOYSA-N 0.000 description 1
- ZFIVKAOQEXOYFY-UHFFFAOYSA-N Diepoxybutane Chemical compound C1OC1C1OC1 ZFIVKAOQEXOYFY-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- BQQUFAMSJAKLNB-UHFFFAOYSA-N dicyclopentadiene diepoxide Chemical compound C12C(C3OC33)CC3C2CC2C1O2 BQQUFAMSJAKLNB-UHFFFAOYSA-N 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- DUVOZUPPHBRJJO-UHFFFAOYSA-N ethyl 2-isocyanatoacetate Chemical compound CCOC(=O)CN=C=O DUVOZUPPHBRJJO-UHFFFAOYSA-N 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 230000006855 networking Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
- C07D251/34—Cyanuric or isocyanuric esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772726749 DE2726749A1 (de) | 1977-06-14 | 1977-06-14 | Verfahren zur herstellung von 2,4,6- triketohexahydrotriazinen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772726749 DE2726749A1 (de) | 1977-06-14 | 1977-06-14 | Verfahren zur herstellung von 2,4,6- triketohexahydrotriazinen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2726749A1 true DE2726749A1 (de) | 1979-01-04 |
| DE2726749C2 DE2726749C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-05-21 |
Family
ID=6011493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772726749 Granted DE2726749A1 (de) | 1977-06-14 | 1977-06-14 | Verfahren zur herstellung von 2,4,6- triketohexahydrotriazinen |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2726749A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0047452A1 (de) * | 1980-09-09 | 1982-03-17 | Bayer Ag | Verfahren zur Herstellung von Isocyanatgruppen aufweisenden Isocyanuraten die nach diesem Verfahren erhaltenen Verbindungen sowie ihre Verwendung als Isocyanatkomponente in Polyurethanlacken |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1106767B (de) * | 1957-03-26 | 1961-05-18 | Us Rubber Co | Verfahren zur Trimerisierung von Arylisocyanaten |
| DE2325826A1 (de) * | 1973-05-22 | 1974-12-19 | Veba Chemie Ag | Lagerstabile polyisocyanate und deren herstellung |
-
1977
- 1977-06-14 DE DE19772726749 patent/DE2726749A1/de active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1106767B (de) * | 1957-03-26 | 1961-05-18 | Us Rubber Co | Verfahren zur Trimerisierung von Arylisocyanaten |
| DE2325826A1 (de) * | 1973-05-22 | 1974-12-19 | Veba Chemie Ag | Lagerstabile polyisocyanate und deren herstellung |
Non-Patent Citations (1)
| Title |
|---|
| DE-PS 26 44 684 (gutachtlich) * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0047452A1 (de) * | 1980-09-09 | 1982-03-17 | Bayer Ag | Verfahren zur Herstellung von Isocyanatgruppen aufweisenden Isocyanuraten die nach diesem Verfahren erhaltenen Verbindungen sowie ihre Verwendung als Isocyanatkomponente in Polyurethanlacken |
| US4419513A (en) | 1980-09-09 | 1983-12-06 | Bayer Aktiengesellschaft | Isocyanato-isocyanurates, and process for the production thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2726749C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-05-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1229016B1 (de) | Katalysator und Verfahren zur Herstellung von niedrigviskosen und farbreduzierten isocyanatgruppenhaltigen Polyisocyanaten | |
| EP0317744B1 (de) | Verfahren zur Herstellung (cyclo)-aliphatischer Uretdione | |
| EP0017998B2 (de) | Verfahren zur kontinuierlichen Herstellung von Isocyanuratgruppen enhaltenden (cyclo)-aliphatischen Polyisocyanaten | |
| EP0668271B1 (de) | Verfahren zur Herstellung von Isocyanuratgruppen aufweisenden Polyisocyanaten | |
| EP0000348B1 (de) | Polyuret-Polyisocyanate, Verfahren zu deren Herstellung, sowie deren Verwendung bei der Herstellung von Polyurethankunststoffen. | |
| EP0478990B1 (de) | Polyisocyanatgemisch, ein Verfahren zu seiner Herstellung und seine Verwendung in Polyurethanlacken | |
| DE19944373A1 (de) | Katalysator und Verfahren zur Herstellung von farbreduzierten isocyanuratgruppenhaltigen Polyisocyananten | |
| EP0045995A1 (de) | Verfahren zur Herstellung eines isocyanuratfreien Uretdions aus Isophorondiisocyanat | |
| EP0003765A1 (de) | Verfahren zur Herstellung von Isocyanuratgruppen aufweisenden Polyisocyanaten auf Basis von 1-Isocyanato-3,3,5-trimethyl-5-isocyanatomethylcyclohexan und ihre Verwendung als Isocyanatkomponente in Polyurethanlacken | |
| EP0671426A1 (de) | Modifizierte (cyclo)aliphatische Polyisocyanatmischungen, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| EP1396485B1 (de) | Verfahren zur Herstellung von geruchsarmen und lagerstabilen monomerhaltigen Polyisocyanuraten aus Isophorondiisocyanat | |
| DE2644684C2 (de) | Verfahren zur Herstellung von 2,4,6-Triketohexahydrotriazinen | |
| DE2447348A1 (de) | Verfahren zur herstellung von diarylcarbonaten | |
| DE3235933A1 (de) | Verfahren zur herstellung bicyclischer orthoesteramide | |
| EP1318160B1 (de) | Katalysatoren und Verfahren zur Herstellung von Isocyanuratgruppen enthaltenden Polyisocyanaten und deren Verwendung | |
| EP0630928B1 (de) | Verfahren zur Herstellung von Isocyanurat- und/oder Uretdiongruppen enthaltenden Polyisocyanaten mit reduzierter Farbzahl und verbesserter Lagerstabilität sowie nach diesem Verfahren hergestellte Produkte | |
| DE10131525A1 (de) | Verfahren zur Herstellung von geruchsarmen und lagerstabilen monomerhaltigen Polyisocyanuraten aus Isophorondiisocyanat | |
| EP3569624A1 (de) | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung | |
| DE3001060C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE2726749A1 (de) | Verfahren zur herstellung von 2,4,6- triketohexahydrotriazinen | |
| DE2724914C2 (de) | Verfahren zur Herstellung von alipathisch- und cycloalipathisch substituierten 2,4,6-Triketohexahydrotriazinen | |
| DE3443342A1 (de) | Verfahren zur herstellung von modifizierten polyisocyanaten, die nach diesem verfahren erhaeltlichen verbindungen und ihre verwendung in polyurethanlacken | |
| DE2946085A1 (de) | Blockierte isocyanatgruppen und isocyanuratgruppen enthaltende gemische sowie deren herstellung | |
| EP1454933A1 (de) | Verfahren zur Herstellung von geruchsarmen und lagerstabilen monomerhaltigen Polyisocyanuraten auf Basis von Isophorondiisocyanat | |
| DE1203792B (de) | Verfahren zur Herstellung von Isocyanursaeure-derivaten durch katalytische Polymerisation von organischen Isocyanaten |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| 8110 | Request for examination paragraph 44 | ||
| 8127 | New person/name/address of the applicant |
Owner name: HUELS AG, 4370 MARL, DE |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |