DE1720768A1 - Kunststoffe auf Isocyanatbasis und Verfahren zu ihrer Herstellung - Google Patents
Kunststoffe auf Isocyanatbasis und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1720768A1 DE1720768A1 DE19681720768 DE1720768A DE1720768A1 DE 1720768 A1 DE1720768 A1 DE 1720768A1 DE 19681720768 DE19681720768 DE 19681720768 DE 1720768 A DE1720768 A DE 1720768A DE 1720768 A1 DE1720768 A1 DE 1720768A1
- Authority
- DE
- Germany
- Prior art keywords
- τοη
- phenols
- group
- mannich bases
- compounds
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 239000012948 isocyanate Substances 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 12
- 150000002513 isocyanates Chemical class 0.000 title claims description 11
- 239000004033 plastic Substances 0.000 title claims description 10
- 229920003023 plastic Polymers 0.000 title claims description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 41
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 27
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 17
- 150000002989 phenols Chemical class 0.000 claims description 17
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- 239000006260 foam Substances 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 8
- 150000003335 secondary amines Chemical class 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 5
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 5
- 239000004604 Blowing Agent Substances 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- 230000006735 deficit Effects 0.000 claims 1
- 239000003054 catalyst Substances 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 16
- -1 aralkyl radicals Chemical class 0.000 description 15
- 239000005056 polyisocyanate Substances 0.000 description 13
- 229920001228 polyisocyanate Polymers 0.000 description 13
- 230000000694 effects Effects 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 5
- 235000013824 polyphenols Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000000123 paper Substances 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001414 amino alcohols Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000003380 propellant Substances 0.000 description 3
- 229960004889 salicylic acid Drugs 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- XWCDCDSDNJVCLO-UHFFFAOYSA-N Chlorofluoromethane Chemical class FCCl XWCDCDSDNJVCLO-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 238000004049 embossing Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003303 reheating Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical compound SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical class O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- FYPLRZZYDCBUAB-UHFFFAOYSA-N 1-isocyanato-2-(1-isocyanatoethyl)benzene Chemical compound O=C=NC(C)C1=CC=CC=C1N=C=O FYPLRZZYDCBUAB-UHFFFAOYSA-N 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- DMAXMXPDVWTIRV-UHFFFAOYSA-N 2-(2-phenylethyl)phenol Chemical class OC1=CC=CC=C1CCC1=CC=CC=C1 DMAXMXPDVWTIRV-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- MVRPPTGLVPEMPI-UHFFFAOYSA-N 2-cyclohexylphenol Chemical class OC1=CC=CC=C1C1CCCCC1 MVRPPTGLVPEMPI-UHFFFAOYSA-N 0.000 description 1
- JHYNEQNPKGIOQF-UHFFFAOYSA-N 3,4-dihydro-2h-phosphole Chemical class C1CC=PC1 JHYNEQNPKGIOQF-UHFFFAOYSA-N 0.000 description 1
- JSFITYFUKSFPBZ-UHFFFAOYSA-N 4-(7-methyloctyl)phenol Chemical compound CC(C)CCCCCCC1=CC=C(O)C=C1 JSFITYFUKSFPBZ-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical class N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 1
- 235000003407 Sigesbeckia orientalis Nutrition 0.000 description 1
- 240000003801 Sigesbeckia orientalis Species 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Chemical group 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 210000005056 cell body Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000004872 foam stabilizing agent Substances 0.000 description 1
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical group [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000003003 phosphines Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000582 polyisocyanurate Polymers 0.000 description 1
- 239000011495 polyisocyanurate Substances 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 229960000581 salicylamide Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- HSVFKFNNMLUVEY-UHFFFAOYSA-N sulfuryl diazide Chemical class [N-]=[N+]=NS(=O)(=O)N=[N+]=[N-] HSVFKFNNMLUVEY-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 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
- 239000002023 wood Substances 0.000 description 1
- 150000003739 xylenols Chemical class 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
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/1825—Catalysts containing secondary or tertiary amines or salts thereof having hydroxy or primary amino groups
-
- 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
- C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
-
- 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
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/1816—Catalysts containing secondary or tertiary amines or salts thereof having carbocyclic groups
-
- 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
- C08G2115/00—Oligomerisation
-
- 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
- C08G2115/00—Oligomerisation
- C08G2115/02—Oligomerisation to isocyanurate groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S521/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S521/901—Cellular polymer containing a carbodiimide structure
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S521/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S521/902—Cellular polymer containing an isocyanurate structure
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 (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681720768 DE1720768A1 (de) | 1968-01-02 | 1968-01-02 | Kunststoffe auf Isocyanatbasis und Verfahren zu ihrer Herstellung |
| DE19681720769 DE1720769C3 (de) | 1968-01-02 | 1968-01-02 | Verfahren zur Herstellung von gegebenenfalls zellförmigen Isocyanuratgruppen aufweisenden Formkörpern |
| CH1860168A CH501687A (de) | 1968-01-02 | 1968-12-12 | Verfahren zur Herstellung von Formkörpern oder Überzügen aus isocyanuratgruppenhaltigen Polymerisaten |
| CH1860268A CH501688A (de) | 1968-01-02 | 1968-12-12 | Verfahren zur Herstellung von Formkörpern aus isocyanuratgruppenhaltigen Polymerisaten |
| DK629568A DK130470B (da) | 1968-01-02 | 1968-12-20 | Fremgangsmåde til fremstilling af cellulære eller ikke-cellulære polyisocyanuratformstoffer. |
| US787559A US3580868A (en) | 1968-01-02 | 1968-12-27 | Polyisocyanurate resin and foam formation catalyzed by mannich bases |
| US787565A US3620986A (en) | 1968-01-02 | 1968-12-27 | Synthetic resins comprising reaction products of isocyanates and process for their production |
| NO521868A NO127620B (en, 2012) | 1968-01-02 | 1968-12-28 | |
| NL6818821A NL6818821A (en, 2012) | 1968-01-02 | 1968-12-30 | |
| SE18025/68A SE353340B (en, 2012) | 1968-01-02 | 1968-12-30 | |
| NL6818820A NL6818820A (en, 2012) | 1968-01-02 | 1968-12-30 | |
| BE726333D BE726333A (en, 2012) | 1968-01-02 | 1968-12-31 | |
| FR1600289D FR1600289A (en, 2012) | 1968-01-02 | 1968-12-31 | |
| GB285/69A GB1195821A (en) | 1968-01-02 | 1969-01-02 | Synthetic Resins comprising Reaction Products of Isocyanates and process for their production |
| GB287/69A GB1195822A (en) | 1968-01-02 | 1969-01-02 | Synthetic Resins obtained from Isocyanates and process for their production |
| AT1269A AT286633B (de) | 1968-01-02 | 1969-01-02 | Verfahren zur Herstellung von gegebenenfalls zellförmigen, Isocyanuratgruppen enthaltenden Kunststoffen |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0054461 | 1968-01-02 | ||
| DE19681720769 DE1720769C3 (de) | 1968-01-02 | 1968-01-02 | Verfahren zur Herstellung von gegebenenfalls zellförmigen Isocyanuratgruppen aufweisenden Formkörpern |
| DEF0054465 | 1968-01-02 | ||
| DE19681720768 DE1720768A1 (de) | 1968-01-02 | 1968-01-02 | Kunststoffe auf Isocyanatbasis und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1720768A1 true DE1720768A1 (de) | 1971-07-15 |
Family
ID=27430656
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681720768 Pending DE1720768A1 (de) | 1968-01-02 | 1968-01-02 | Kunststoffe auf Isocyanatbasis und Verfahren zu ihrer Herstellung |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US3620986A (en, 2012) |
| BE (1) | BE726333A (en, 2012) |
| CH (2) | CH501688A (en, 2012) |
| DE (1) | DE1720768A1 (en, 2012) |
| FR (1) | FR1600289A (en, 2012) |
| GB (2) | GB1195821A (en, 2012) |
| NL (2) | NL6818821A (en, 2012) |
| SE (1) | SE353340B (en, 2012) |
Cited By (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2534247A1 (de) * | 1975-07-31 | 1977-02-03 | Bayer Ag | Verfahren zur herstellung von formteilen |
| DE2631167A1 (de) * | 1976-07-10 | 1978-01-19 | Bayer Ag | Verfahren zur herstellung von massiven formteilen |
| EP0659814A1 (de) | 1993-12-23 | 1995-06-28 | Bayer Ag | Verwendung von Antikernverfärbungsmitteln bei der Herstellung von Schaumstoffen auf Isocyanatbasis |
| US6380273B1 (en) | 1999-06-16 | 2002-04-30 | Clariant Gmbh | Process for producing flame-retardant flexible polyurethane foams |
| EP1964880A1 (de) | 2007-03-02 | 2008-09-03 | Lanxess Deutschland GmbH | Halogenfreie, flammgeschützte Polyurethanschaumstoffe |
| EP2138520A2 (de) | 2008-06-28 | 2009-12-30 | Bayer MaterialScience AG | Verfahren zur Erniedrigung von Emissionen eines Polyurethanschaumstoffes |
| EP2154185A1 (de) | 2008-08-16 | 2010-02-17 | Lanxess Deutschland GmbH | Halogenfreie, flammgeschützte Polyurethanschaumstoffe mit geringem Scorch |
| EP2256141A2 (de) | 2009-05-27 | 2010-12-01 | Bayer MaterialScience AG | Verrfahren zur Herstellung von Polyurethan-Weichschaumstoffen mit niedriger Emission |
| WO2011003590A2 (de) | 2009-07-09 | 2011-01-13 | Bayer Materialscience Ag | Verfahren zur herstellung von flammgeschützten polyurethanschaumstoffen mit guten dauergebrauchseigenschaften |
| DE102009047846A1 (de) | 2009-09-30 | 2011-03-31 | Bayer Materialscience Ag | Verfahren zur Erniedrigung von Emissionen eines Polyurethanschaumstoffes |
| WO2013182527A1 (en) | 2012-06-06 | 2013-12-12 | Bayer Materialscience Ag | Process for the production of viscoelastic polyurethane foam |
| EP2687535A1 (de) | 2012-07-20 | 2014-01-22 | LANXESS Deutschland GmbH | Halogenfreie Poly(alkylenphosphate) |
| EP2848640A1 (de) | 2013-09-13 | 2015-03-18 | LANXESS Deutschland GmbH | Phosphorsäureester-Zubereitungen mit verringerter Hygroskopie |
| EP2985335A1 (de) | 2014-08-15 | 2016-02-17 | LANXESS Deutschland GmbH | Flammwidrige Polyurethanschaumstoffe mit geringer Kernverfärbung |
| EP3050890A1 (de) | 2015-01-27 | 2016-08-03 | LANXESS Deutschland GmbH | Hydroxylgruppen-haltige Poly(alkylenphosphate) |
| EP3293218A1 (de) | 2016-09-13 | 2018-03-14 | Covestro Deutschland AG | Verfahren zur erniedrigung der aldehydemissionen von polyurethanschaumstoffen |
| EP3330308A1 (de) | 2016-12-05 | 2018-06-06 | Covestro Deutschland AG | Verfahren zur herstellung von tdi-basierten polyurethanweichschaumstoffen enthaltend organische säureanhydride und/oder organische säurechloride |
| EP3330307A1 (de) | 2016-12-05 | 2018-06-06 | Covestro Deutschland AG | Verwendung von acrylsäureestern und amiden zur erniedrigung von emissionen eines polyurethanschaumstoffes |
| EP3336115A1 (de) | 2016-12-19 | 2018-06-20 | Covestro Deutschland AG | Verfahren zur erniedrigung von emissionen eines polyurethanschaumstoffes |
| EP3336130A1 (de) | 2016-12-19 | 2018-06-20 | Covestro Deutschland AG | Verfahren zur herstellung von polyetherthiocarbonatpolyolen |
| EP3388479A1 (de) | 2017-04-10 | 2018-10-17 | LANXESS Deutschland GmbH | Poly(alkylenphosphate) mit verringerter hygroskopie |
| EP3425187A1 (de) | 2017-07-07 | 2019-01-09 | Covestro Deutschland AG | Flammgeschütze isolierung für verbrennungsmotoren |
| EP3492503A1 (de) | 2017-11-29 | 2019-06-05 | Covestro Deutschland AG | Imidhaltige polyester |
| EP3660065A1 (de) | 2018-11-28 | 2020-06-03 | LANXESS Deutschland GmbH | Zubereitungen mit verbesserter wirksamkeit als flammschutzmittel |
| EP3760659A1 (de) | 2019-07-01 | 2021-01-06 | Covestro Deutschland AG | Amingestartete polyole als einbaubare katalysatoren im hr-schaum |
| WO2022238293A1 (en) | 2021-05-11 | 2022-11-17 | Clariant International Ltd | Flexible foams comprising flame-retardant polyurethane, a process for their production and use thereof |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3723366A (en) * | 1971-06-25 | 1973-03-27 | Basf Wyandotte Corp | Carbodiimide foams and improved process for preparing same |
| US4124545A (en) * | 1973-05-22 | 1978-11-07 | Bayer Aktiengesellschaft | Carbamic acid esters as catalysts for trimerization of isocyanates |
| US3887501A (en) * | 1973-12-21 | 1975-06-03 | Basf Wyandotte Corp | Process for the preparation of carbodiimide-isocyanurate foams |
| US3896052A (en) * | 1974-01-30 | 1975-07-22 | Upjohn Co | Cocatalyst system for trimerizing polyisocyanates |
| US3994837A (en) * | 1974-10-02 | 1976-11-30 | Basf Wyandotte Corporation | Urethane-modified carbodiimide-isocynurate foams prepared from TDI-rich isocyanates |
| US3994839A (en) * | 1974-10-29 | 1976-11-30 | Basf Wyandotte Corporation | Urethane modified carbodiimide foams derived from flame retardant polyols |
| US3998766A (en) * | 1974-12-26 | 1976-12-21 | Basf Wyandotte Corporation | Urethane modified carbodimide-isocyanurate foams from organic polyisocyanates and oxyalkylated mannich polyols |
| US3981829A (en) * | 1974-12-30 | 1976-09-21 | Basf Wyandotte Corporation | Process for the preparation of carbodiimide-isocyanurate foams |
| US3963680A (en) * | 1975-03-17 | 1976-06-15 | Minnesota Mining And Manufacturing Company | One-part, room-temperature latent, curable isocyanate compositions |
| DE2551634C3 (de) * | 1975-11-18 | 1980-07-17 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Isocyanuratgruppen aufweisenden Polyisocyanaten |
| US4039487A (en) * | 1976-01-19 | 1977-08-02 | The Upjohn Company | Cellular isocyanurate polymer |
| US4057535A (en) * | 1976-04-14 | 1977-11-08 | Tatyana Esperovna Lipatova | Adhesive for gluing together soft body tissues |
| US4184022A (en) * | 1978-09-15 | 1980-01-15 | Owens-Corning Fiberglas Corporation | Polyisocyanurate foam comprising reaction product of a polyisocyanate and a polyol mixture comprising a carboxylic ester polyol and a resole polyether polyol using a catalyst comprising dimethylethanolamine and an alkali metal salt of a carboxylic acid |
| US4286072A (en) * | 1979-10-15 | 1981-08-25 | Texaco Development Corp. | Novel polyisocyanurate catalysts |
| US4310634A (en) * | 1979-10-15 | 1982-01-12 | Texaco Development Corp. | Novel polyisocyanurate catalyst |
| US4388420A (en) * | 1980-05-05 | 1983-06-14 | Basf Wyandotte Corporation | Process for preparing a microcellular polyurethane foam with improved green strength |
| US4886626A (en) * | 1987-05-19 | 1989-12-12 | Crest-Foam Corporation | Conductive polyurethane foam compositions containing tetralyanoethylene and method |
| US5028355A (en) * | 1987-05-19 | 1991-07-02 | Crest-Foam Corporation | Conductive polyurethane foam containing picric acid and analog thereof |
| US5157057A (en) * | 1991-07-30 | 1992-10-20 | Arco Chemical Technology, L.P. | Rim compositions using amino acid salt catalysts |
| DE10247974A1 (de) * | 2002-10-15 | 2004-05-13 | Clariant Gmbh | Flammwidrige Polyurethanweichschäume mit hoher Alterungsbeständigkeit |
| DE10247973B4 (de) * | 2002-10-15 | 2005-05-04 | Clariant Gmbh | Halogenreduzierte Flammschutzmittelmischungen zur Herstellung von emissionsstabilen Polyurethanweichschäumen |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2033092A (en) * | 1933-12-23 | 1936-03-03 | Roehm & Haas Co | Soap Forming Compounds and Process of making same |
| US2220834A (en) * | 1939-03-14 | 1940-11-05 | Resinous Prod & Chemical Co | Phenolic triamines |
| US3248372A (en) * | 1960-11-08 | 1966-04-26 | Bayer Ag | Glycol modified isocyanurate containing polyisocyanates |
| GB967443A (en) * | 1961-09-11 | 1964-08-19 | Shell Int Research | Improvements in or relating to the production of urethanes |
| FR1511865A (fr) * | 1966-02-18 | 1968-02-02 | Nisshin Boseki Kabushiki Kaish | Procédé de préparation de mousses de matière plastique rigides et produits obtenus |
-
1968
- 1968-01-02 DE DE19681720768 patent/DE1720768A1/de active Pending
- 1968-12-12 CH CH1860268A patent/CH501688A/de not_active IP Right Cessation
- 1968-12-12 CH CH1860168A patent/CH501687A/de not_active IP Right Cessation
- 1968-12-27 US US787565A patent/US3620986A/en not_active Expired - Lifetime
- 1968-12-27 US US787559A patent/US3580868A/en not_active Expired - Lifetime
- 1968-12-30 NL NL6818821A patent/NL6818821A/xx unknown
- 1968-12-30 SE SE18025/68A patent/SE353340B/xx unknown
- 1968-12-30 NL NL6818820A patent/NL6818820A/xx unknown
- 1968-12-31 FR FR1600289D patent/FR1600289A/fr not_active Expired
- 1968-12-31 BE BE726333D patent/BE726333A/xx unknown
-
1969
- 1969-01-02 GB GB285/69A patent/GB1195821A/en not_active Expired
- 1969-01-02 GB GB287/69A patent/GB1195822A/en not_active Expired
Cited By (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2534247A1 (de) * | 1975-07-31 | 1977-02-03 | Bayer Ag | Verfahren zur herstellung von formteilen |
| DE2631167A1 (de) * | 1976-07-10 | 1978-01-19 | Bayer Ag | Verfahren zur herstellung von massiven formteilen |
| EP0659814A1 (de) | 1993-12-23 | 1995-06-28 | Bayer Ag | Verwendung von Antikernverfärbungsmitteln bei der Herstellung von Schaumstoffen auf Isocyanatbasis |
| US6380273B1 (en) | 1999-06-16 | 2002-04-30 | Clariant Gmbh | Process for producing flame-retardant flexible polyurethane foams |
| EP1964880A1 (de) | 2007-03-02 | 2008-09-03 | Lanxess Deutschland GmbH | Halogenfreie, flammgeschützte Polyurethanschaumstoffe |
| DE102007010160A1 (de) | 2007-03-02 | 2008-09-04 | Lanxess Deutschland Gmbh | Halogenfreie, flammgeschützte Polyurethanschaumstoffe |
| EP2138520A2 (de) | 2008-06-28 | 2009-12-30 | Bayer MaterialScience AG | Verfahren zur Erniedrigung von Emissionen eines Polyurethanschaumstoffes |
| DE102008030763A1 (de) | 2008-06-28 | 2009-12-31 | Bayer Materialscience Ag | Verfahren zur Erniedrigung von Emissionen eines Polyurethanschaumstoffes |
| EP2154185A1 (de) | 2008-08-16 | 2010-02-17 | Lanxess Deutschland GmbH | Halogenfreie, flammgeschützte Polyurethanschaumstoffe mit geringem Scorch |
| DE102008038054A1 (de) | 2008-08-16 | 2010-02-18 | Lanxess Deutschland Gmbh | Halogenfreie, flammgeschützte Polyurethanschaumstoffe mit geringem Scorch |
| EP2256141A2 (de) | 2009-05-27 | 2010-12-01 | Bayer MaterialScience AG | Verrfahren zur Herstellung von Polyurethan-Weichschaumstoffen mit niedriger Emission |
| WO2011003590A2 (de) | 2009-07-09 | 2011-01-13 | Bayer Materialscience Ag | Verfahren zur herstellung von flammgeschützten polyurethanschaumstoffen mit guten dauergebrauchseigenschaften |
| DE102009047846A1 (de) | 2009-09-30 | 2011-03-31 | Bayer Materialscience Ag | Verfahren zur Erniedrigung von Emissionen eines Polyurethanschaumstoffes |
| WO2011038846A1 (de) | 2009-09-30 | 2011-04-07 | Bayer Materialscience Ag | Verfahren zur erniedrigung von emissionen eines polyurethanschaumstoffes |
| WO2013182527A1 (en) | 2012-06-06 | 2013-12-12 | Bayer Materialscience Ag | Process for the production of viscoelastic polyurethane foam |
| US9512258B2 (en) | 2012-06-06 | 2016-12-06 | Covestro Deutschland Ag | Process for the production of viscoelastic polyurethane foam |
| EP2687535A1 (de) | 2012-07-20 | 2014-01-22 | LANXESS Deutschland GmbH | Halogenfreie Poly(alkylenphosphate) |
| EP2687534A1 (de) | 2012-07-20 | 2014-01-22 | LANXESS Deutschland GmbH | Halogenfreie Poly(alkylenphosphate) |
| EP2848640A1 (de) | 2013-09-13 | 2015-03-18 | LANXESS Deutschland GmbH | Phosphorsäureester-Zubereitungen mit verringerter Hygroskopie |
| EP2860211A1 (de) | 2013-09-13 | 2015-04-15 | LANXESS Deutschland GmbH | Phosphorsäureester-Zubereitungen mit verringerter Hygroskopie |
| EP2985335A1 (de) | 2014-08-15 | 2016-02-17 | LANXESS Deutschland GmbH | Flammwidrige Polyurethanschaumstoffe mit geringer Kernverfärbung |
| EP2985336A1 (de) | 2014-08-15 | 2016-02-17 | LANXESS Deutschland GmbH | Flammwidrige polyurethanschaumstoffe mit geringer kernverfärbung |
| EP3050891A1 (de) | 2015-01-27 | 2016-08-03 | LANXESS Deutschland GmbH | Hydroxylgruppen-haltige poly(alkylenphosphate) |
| EP3050890A1 (de) | 2015-01-27 | 2016-08-03 | LANXESS Deutschland GmbH | Hydroxylgruppen-haltige Poly(alkylenphosphate) |
| EP3293218A1 (de) | 2016-09-13 | 2018-03-14 | Covestro Deutschland AG | Verfahren zur erniedrigung der aldehydemissionen von polyurethanschaumstoffen |
| WO2018050628A1 (de) | 2016-09-13 | 2018-03-22 | Covestro Deutschland Ag | Verfahren zur erniedrigung der aldehydemissionen von polyurethanschaumstoffen |
| EP3330308A1 (de) | 2016-12-05 | 2018-06-06 | Covestro Deutschland AG | Verfahren zur herstellung von tdi-basierten polyurethanweichschaumstoffen enthaltend organische säureanhydride und/oder organische säurechloride |
| EP3330307A1 (de) | 2016-12-05 | 2018-06-06 | Covestro Deutschland AG | Verwendung von acrylsäureestern und amiden zur erniedrigung von emissionen eines polyurethanschaumstoffes |
| WO2018104222A1 (de) | 2016-12-05 | 2018-06-14 | Covestro Deutschland Ag | Verwendung von acrylsäureestern und –amiden zur erniedrigung von emissionen eines polyurethanschaumstoffes |
| WO2018104221A1 (de) | 2016-12-05 | 2018-06-14 | Covestro Deutschland Ag | Verfahren zur herstellung von tdi-basierten polyurethanweichschaumstoffen enthaltend organische säureanhydride und/oder organische säurechloride |
| EP3336115A1 (de) | 2016-12-19 | 2018-06-20 | Covestro Deutschland AG | Verfahren zur erniedrigung von emissionen eines polyurethanschaumstoffes |
| EP3336130A1 (de) | 2016-12-19 | 2018-06-20 | Covestro Deutschland AG | Verfahren zur herstellung von polyetherthiocarbonatpolyolen |
| WO2018114820A1 (de) | 2016-12-19 | 2018-06-28 | Covestro Deutschland Ag | Verfahren zur erniedrigung von emissionen eines polyurethanschaumstoffes |
| WO2018114837A1 (de) | 2016-12-19 | 2018-06-28 | Covestro Deutschland Ag | Verfahren zur herstellung von polyetherthiocarbonatpolyolen |
| EP3388479A1 (de) | 2017-04-10 | 2018-10-17 | LANXESS Deutschland GmbH | Poly(alkylenphosphate) mit verringerter hygroskopie |
| EP3388480A1 (de) | 2017-04-10 | 2018-10-17 | LANXESS Deutschland GmbH | Poly(alkylenphosphate) mit verringerter hygroskopie |
| EP3425187A1 (de) | 2017-07-07 | 2019-01-09 | Covestro Deutschland AG | Flammgeschütze isolierung für verbrennungsmotoren |
| EP3492503A1 (de) | 2017-11-29 | 2019-06-05 | Covestro Deutschland AG | Imidhaltige polyester |
| WO2019105935A1 (de) | 2017-11-29 | 2019-06-06 | Covestro Deutschland Ag | Imidhaltige polyester |
| EP3660065A1 (de) | 2018-11-28 | 2020-06-03 | LANXESS Deutschland GmbH | Zubereitungen mit verbesserter wirksamkeit als flammschutzmittel |
| EP3660064A1 (de) | 2018-11-28 | 2020-06-03 | LANXESS Deutschland GmbH | Zubereitungen mit verbesserter wirksamkeit als flammschutzmittel |
| EP3760659A1 (de) | 2019-07-01 | 2021-01-06 | Covestro Deutschland AG | Amingestartete polyole als einbaubare katalysatoren im hr-schaum |
| WO2021001229A1 (de) | 2019-07-01 | 2021-01-07 | Covestro Intellectual Property Gmbh & Co. Kg | Amingestartete polyole als einbaubare katalysatoren im hr-schaum |
| WO2022238293A1 (en) | 2021-05-11 | 2022-11-17 | Clariant International Ltd | Flexible foams comprising flame-retardant polyurethane, a process for their production and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6818821A (en, 2012) | 1969-07-04 |
| CH501687A (de) | 1971-01-15 |
| GB1195822A (en) | 1970-06-24 |
| GB1195821A (en) | 1970-06-24 |
| DE1720769A1 (de) | 1972-03-02 |
| US3580868A (en) | 1971-05-25 |
| DE1720769B2 (de) | 1973-06-20 |
| FR1600289A (en, 2012) | 1970-07-20 |
| CH501688A (de) | 1971-01-15 |
| US3620986A (en) | 1971-11-16 |
| SE353340B (en, 2012) | 1973-01-29 |
| BE726333A (en, 2012) | 1969-05-29 |
| NL6818820A (en, 2012) | 1969-07-04 |
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