CA1136349A - Process for the manufacture of flexible polyurethane foams with cyanic acid derivatives - Google Patents
Process for the manufacture of flexible polyurethane foams with cyanic acid derivativesInfo
- Publication number
- CA1136349A CA1136349A CA000325402A CA325402A CA1136349A CA 1136349 A CA1136349 A CA 1136349A CA 000325402 A CA000325402 A CA 000325402A CA 325402 A CA325402 A CA 325402A CA 1136349 A CA1136349 A CA 1136349A
- Authority
- CA
- Canada
- Prior art keywords
- mixture
- weight
- percent
- process according
- diphenylmethane
- 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
- 229920005830 Polyurethane Foam Polymers 0.000 title claims abstract description 25
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical class OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 25
- 239000011496 polyurethane foam Substances 0.000 title claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 16
- 239000000203 mixture Substances 0.000 claims abstract description 67
- 229920005862 polyol Polymers 0.000 claims abstract description 43
- 150000003077 polyols Chemical class 0.000 claims abstract description 42
- -1 polyphenylene Polymers 0.000 claims abstract description 34
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 33
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 30
- 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 claims abstract description 22
- 229920000877 Melamine resin Polymers 0.000 claims abstract description 14
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000004604 Blowing Agent Substances 0.000 claims abstract description 11
- 239000004970 Chain extender Substances 0.000 claims abstract description 11
- 239000003112 inhibitor Substances 0.000 claims abstract description 11
- 239000000654 additive Substances 0.000 claims abstract description 10
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229920000265 Polyparaphenylene Polymers 0.000 claims abstract description 8
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims abstract description 6
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims abstract description 5
- ZILVNHNSYBNLSZ-UHFFFAOYSA-N 2-(diaminomethylideneamino)guanidine Chemical compound NC(N)=NNC(N)=N ZILVNHNSYBNLSZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims abstract description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 6
- 150000008282 halocarbons Chemical class 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000004088 foaming agent Substances 0.000 claims description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 abstract description 10
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 239000012774 insulation material Substances 0.000 abstract description 3
- 238000010276 construction Methods 0.000 abstract description 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 abstract description 2
- 239000006260 foam Substances 0.000 description 21
- 239000004721 Polyphenylene oxide Substances 0.000 description 13
- 229920000570 polyether Polymers 0.000 description 13
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical class C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 11
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000013065 commercial product Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 229920005906 polyester polyol Polymers 0.000 description 6
- 239000004814 polyurethane Substances 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 5
- 229920002635 polyurethane Polymers 0.000 description 5
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 5
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical class O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000007906 compression Methods 0.000 description 3
- 230000006835 compression Effects 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920006389 polyphenyl polymer Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- FZQMJOOSLXFQSU-UHFFFAOYSA-N 3-[3,5-bis[3-(dimethylamino)propyl]-1,3,5-triazinan-1-yl]-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCN1CN(CCCN(C)C)CN(CCCN(C)C)C1 FZQMJOOSLXFQSU-UHFFFAOYSA-N 0.000 description 2
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-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
- 235000011037 adipic acid Nutrition 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000002184 metal Chemical class 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 125000005702 oxyalkylene group Chemical group 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 229940029284 trichlorofluoromethane Drugs 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- LWBHHRRTOZQPDM-UHFFFAOYSA-N undecanedioic acid Chemical compound OC(=O)CCCCCCCCCC(O)=O LWBHHRRTOZQPDM-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 1
- FCQPNTOQFPJCMF-UHFFFAOYSA-N 1,3-bis[3-(dimethylamino)propyl]urea Chemical compound CN(C)CCCNC(=O)NCCCN(C)C FCQPNTOQFPJCMF-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- OHKOAJUTRVTYSW-UHFFFAOYSA-N 2-[(2-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1N OHKOAJUTRVTYSW-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical group CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 150000001279 adipic acids Chemical class 0.000 description 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000001609 comparable effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000007973 cyanuric acids Chemical class 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 229940042935 dichlorodifluoromethane Drugs 0.000 description 1
- UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
- 229940099364 dichlorofluoromethane Drugs 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 239000012971 dimethylpiperazine Substances 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000009970 fire resistant effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- VSUFNZWEKZXHNA-UHFFFAOYSA-N hexane-1,6-diol;propane-1,2,3-triol Chemical compound OCC(O)CO.OCCCCCCO VSUFNZWEKZXHNA-UHFFFAOYSA-N 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- DSSXKBBEJCDMBT-UHFFFAOYSA-M lead(2+);octanoate Chemical compound [Pb+2].CCCCCCCC([O-])=O DSSXKBBEJCDMBT-UHFFFAOYSA-M 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003673 urethanes Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/0014—Use of organic additives
- C08J9/0028—Use of organic additives containing nitrogen
-
- 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
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3838—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing cyano 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
- C08G18/06—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
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3842—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
- C08G18/3851—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing three nitrogen atoms in the ring
-
- 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
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2815554.6 | 1978-04-11 | ||
| DE19782815554 DE2815554A1 (de) | 1978-04-11 | 1978-04-11 | Schwerentflammbare polyurethan-weichschaumstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1136349A true CA1136349A (en) | 1982-11-23 |
Family
ID=6036679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000325402A Expired CA1136349A (en) | 1978-04-11 | 1979-04-10 | Process for the manufacture of flexible polyurethane foams with cyanic acid derivatives |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4258141A (enExample) |
| EP (1) | EP0004618B1 (enExample) |
| JP (1) | JPS54134800A (enExample) |
| AT (1) | AT379604B (enExample) |
| CA (1) | CA1136349A (enExample) |
| DE (2) | DE2815554A1 (enExample) |
| MX (1) | MX149926A (enExample) |
Families Citing this family (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3025309A1 (de) * | 1980-07-04 | 1982-02-04 | Bayer Ag, 5090 Leverkusen | Gegebenenfalls geschaeumte intumeszenzmassen |
| DE3041731A1 (de) * | 1980-11-05 | 1982-06-09 | Bayer Ag, 5090 Leverkusen | Gegebenenfalls geschaeumte intumeszenzmassen und ihre verwendung |
| DE3109352A1 (de) * | 1981-03-12 | 1982-09-23 | Bayer Ag, 5090 Leverkusen | Gegebenenfalls geschaeumte intumeszenzmassen und ihre verwendung |
| DE3306698A1 (de) * | 1983-02-25 | 1984-08-30 | Bayer Ag, 5090 Leverkusen | Gegebenenfalls geschaeumte intumeszenzmassen und daraus hergestellte formteile |
| US4489178A (en) * | 1983-10-25 | 1984-12-18 | Texaco Inc. | Mannich condensates having fire retardancy properties and manufacture of rigid polyurethane foam therewith |
| DE3412086A1 (de) * | 1984-03-31 | 1985-10-10 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung lagerstabiler cyanamidloesungen in polyolen, einphasig homogene cyanamidloesungen und ihre verwendung |
| GB8421967D0 (en) * | 1984-08-30 | 1984-10-03 | Hickory Springs Mfg Co | Polyurethane foams |
| US4849459A (en) * | 1985-06-27 | 1989-07-18 | Basf Corporation | Flame retardant polyurethane foams |
| GB2177406B (en) * | 1985-06-27 | 1989-07-12 | Basf Corp | Flame retardant polyurethane foams |
| USRE36358E (en) * | 1985-06-28 | 1999-10-26 | Basf Corporation | Flame retardant polyurethane foams |
| GB2177405B (en) * | 1985-06-28 | 1989-08-23 | Basf Corp | Flame retardant polyurethane foams |
| JPS6215220A (ja) * | 1985-07-15 | 1987-01-23 | Takiron Co Ltd | 難燃性ポリウレタンフオ−ムの製造方法 |
| FI895527A0 (fi) * | 1987-05-21 | 1989-11-20 | Reeves Bros Inc | Flammretarderande inre haerdat polyuretanskum med foerbaettrade egenskaper. |
| US4757094A (en) * | 1987-05-21 | 1988-07-12 | Reeves Brothers, Inc. | Melamine cured polyurethane foam with improved properties |
| US4757093A (en) * | 1987-05-21 | 1988-07-12 | Reeves Brothers, Inc. | Flame retardant melamine containing polyurethane foam |
| US4826884A (en) * | 1987-07-20 | 1989-05-02 | Basf Corporation | Flame retardant polyurethane foams resistant to cigarette smoldering ignition |
| US4810729A (en) * | 1987-10-23 | 1989-03-07 | Basf Corporation | Flexible flame resistant polyurethane foams |
| AT389878B (de) * | 1988-02-01 | 1990-02-12 | Danutec Werkstoff | Hochtemperaturbestaendige polyurethanschaeume niedriger dichte, verfahren zu ihrer herstellung und deren verwendung |
| US4908161A (en) * | 1988-06-23 | 1990-03-13 | Harry Fischer | Fire retardant for isocyanate-based foams comprising ammonium sulfate and a cyanuric acid derivative |
| JPH0270719A (ja) * | 1988-06-24 | 1990-03-09 | Bridgestone Corp | 軟質ポリウレタンフォームの製造方法 |
| DE3825147A1 (de) * | 1988-07-23 | 1990-03-08 | Bayer Ag | Verfahren zur herstellung von polyurethanschaumstoffen |
| DE3829958A1 (de) * | 1988-09-03 | 1990-03-08 | Bayer Ag | Verfahren zur herstellung von polyurethanschaumstoffen |
| GB8826727D0 (en) * | 1988-11-15 | 1988-12-21 | Bp Chem Int Ltd | Melamine/urea containing polymer polyols |
| DE3842384A1 (de) * | 1988-12-16 | 1990-07-12 | Bayer Ag | Verfahren zur herstellung von polyurethanschaumstoffen |
| DE3842385A1 (de) * | 1988-12-16 | 1990-07-12 | Bayer Ag | Verfahren zur herstellung von polyurethanschaumstoffen |
| DE3844048A1 (de) * | 1988-12-28 | 1990-07-05 | Basf Ag | Verfahren zur herstellung von flammwidrigen, elastischen polyurethan-weichschaumstoffen unter mitverwendung mindestens eines polyoxyalkylenpolyamins und melamin |
| DE3844049A1 (de) * | 1988-12-28 | 1990-07-05 | Basf Ag | Verfahren zur herstellung von flammwidrigen, elastischen polyurethan-weichschaumstoffen und niedrigviskose melamin-polyether-polyoldispersionen hierfuer |
| US4892893A (en) * | 1989-02-17 | 1990-01-09 | Basf Corporation | Flame retardant polyurethane foams resistant to cigarette smoldering ignition |
| US5171758A (en) * | 1990-03-12 | 1992-12-15 | Olin Corporation | Flame retardant urethane foams made using propylene oxide-based polyols |
| US5124366A (en) * | 1990-11-05 | 1992-06-23 | The Celotex Corporation | Polyisocyanurate foams made with polyester polyols and chlorodifluoromethane as a blowing agent |
| US6883688B1 (en) | 1992-02-24 | 2005-04-26 | Homax Products, Inc. | Aerosol spray texturing systems and methods |
| US7278590B1 (en) | 1992-02-24 | 2007-10-09 | Homax Products, Inc. | Systems and methods for applying texture material to ceiling surfaces |
| US8028864B2 (en) | 1992-02-24 | 2011-10-04 | Homax Products, Inc. | Actuator systems and methods for aerosol wall texturing |
| US5229427A (en) * | 1992-06-02 | 1993-07-20 | Miles Inc. | Flexible, combustion-modified, polyurethane foams |
| JPH0649184U (ja) * | 1992-12-11 | 1994-07-05 | 市光工業株式会社 | 車両用灯具 |
| US6152335A (en) | 1993-03-12 | 2000-11-28 | Homax Products, Inc. | Aerosol spray texture apparatus for a particulate containing material |
| US5837760A (en) * | 1994-03-16 | 1998-11-17 | Elastogran Gmbh | Self-extinguishing thermoplastic polyurethanes and their preparation |
| EP0672696B1 (en) * | 1994-03-18 | 1999-05-19 | Air Products And Chemicals, Inc. | Low odor amine catalysts for polyurethane flexible slabstock foams based on polyester polyols |
| DE19540809A1 (de) * | 1995-09-02 | 1997-03-06 | Basf Ag | Verfahren zur Herstellung von flammwidrigen Polyurethan-Weichschaumstoffen |
| US5885479A (en) * | 1996-08-28 | 1999-03-23 | Basf Aktiengesellschaft | Production of flame-resistant flexible polyurethane foams |
| US5730909A (en) * | 1996-11-26 | 1998-03-24 | Basf Corporation | Flame retardant polyurethane foams |
| US5830926A (en) * | 1997-12-17 | 1998-11-03 | Basf Corporation | Flame retardant polyurethane foams |
| US7500621B2 (en) | 2003-04-10 | 2009-03-10 | Homax Products, Inc. | Systems and methods for securing aerosol systems |
| US20050161531A1 (en) | 2004-01-28 | 2005-07-28 | Greer Lester R.Jr. | Texture material for covering a repaired portion of a textured surface |
| US7677420B1 (en) | 2004-07-02 | 2010-03-16 | Homax Products, Inc. | Aerosol spray texture apparatus for a particulate containing material |
| US7487893B1 (en) * | 2004-10-08 | 2009-02-10 | Homax Products, Inc. | Aerosol systems and methods for dispensing texture material |
| US8344056B1 (en) | 2007-04-04 | 2013-01-01 | Homax Products, Inc. | Aerosol dispensing systems, methods, and compositions for repairing interior structure surfaces |
| US9382060B1 (en) | 2007-04-05 | 2016-07-05 | Homax Products, Inc. | Spray texture material compositions, systems, and methods with accelerated dry times |
| KR20080113741A (ko) * | 2007-06-25 | 2008-12-31 | 김도균 | 인과 질소함유 폴리올 |
| US8124665B2 (en) * | 2008-08-29 | 2012-02-28 | Bayer Materialscience Llc | Decorative molded foams with good impact resistance and fire retardant properties |
| EP2325259A1 (en) | 2009-11-16 | 2011-05-25 | H2V Bvba | Fire retardant for polyurethane foams |
| US8097658B2 (en) * | 2009-11-18 | 2012-01-17 | Bayer Materialscience Llc | Process for the production of medium density decorative molded foams having good fire retardant properties with reduced mold times, fire retardant compositions and foams produced by this process |
| WO2012006548A1 (en) | 2010-07-09 | 2012-01-12 | Air Products And Chemicals, Inc. | Additives for improving polyurethane foam performance |
| US9447223B2 (en) | 2011-07-07 | 2016-09-20 | Air Products And Chemicals, Inc. | Additives for improving natural oil based polyurethane foam performance |
| US9248457B2 (en) | 2011-07-29 | 2016-02-02 | Homax Products, Inc. | Systems and methods for dispensing texture material using dual flow adjustment |
| US9156042B2 (en) | 2011-07-29 | 2015-10-13 | Homax Products, Inc. | Systems and methods for dispensing texture material using dual flow adjustment |
| DE102011056368A1 (de) | 2011-12-13 | 2013-06-13 | Chemische Fabrik Budenheim Kg | Halogenfreies Flammschutzmittel für thermoplastisches Polyurethan (TPU) |
| US9156602B1 (en) | 2012-05-17 | 2015-10-13 | Homax Products, Inc. | Actuators for dispensers for texture material |
| US9435120B2 (en) | 2013-03-13 | 2016-09-06 | Homax Products, Inc. | Acoustic ceiling popcorn texture materials, systems, and methods |
| US9776785B2 (en) | 2013-08-19 | 2017-10-03 | Ppg Architectural Finishes, Inc. | Ceiling texture materials, systems, and methods |
| USD787326S1 (en) | 2014-12-09 | 2017-05-23 | Ppg Architectural Finishes, Inc. | Cap with actuator |
| WO2018037040A1 (de) | 2016-08-25 | 2018-03-01 | Covestro Deutschland Ag | Verfahren zur herstellung von polyurethanpolymeren mit verringertem brennwert |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE581667A (enExample) | 1958-08-15 | |||
| FR1541226A (fr) * | 1966-10-03 | 1968-10-04 | Upjohn Co | Nouvelles compositions de polyisocyanates relativement peu toxiques et leurs procédés de fabrication |
| FR2003124A1 (en) * | 1968-03-02 | 1969-11-07 | Gruenzweig & Hartmann | Fireproofing resin condensation prods. or (co)polymers - with combination of inorganic salt contg. water of crystallisation and organic cpd. releasing non-combustible gas when heated |
| AT306374B (de) * | 1970-09-02 | 1973-04-10 | Chemie Linz Ag | Flammfeste Formmasse auf Basis von Polyurethanen oder Epoxyharzen |
| US3833525A (en) * | 1971-04-23 | 1974-09-03 | Gen Electric | Phenolic blocked isocyanate compositions containing a heterocyclic nitrogen catalyst |
| US4075137A (en) * | 1973-04-19 | 1978-02-21 | Kohkoku Chemical Industry Co., Ltd. | Process for preparing flame retarding polyurethane foams |
| GB1417087A (en) | 1973-05-29 | 1975-12-10 | Ici Ltd | Polyisocyanates |
| DE2348838A1 (de) * | 1973-09-28 | 1975-04-10 | Elastogran Gmbh | Verfahren zur herstellung von flammfesten, isocyanuratgruppenhaltigen polyurethankunststoffen |
| JPS5432479B2 (enExample) * | 1973-11-28 | 1979-10-15 | ||
| NL7503702A (nl) * | 1974-04-01 | 1975-10-03 | Ici Ltd | Werkwijze voor de bereiding van een vuurbesten- dig polyurethaan en voorwerpen, die geheel of ten dele uit het aldus bereide polyurethaan bestaan. |
| CH585524A5 (enExample) * | 1974-04-09 | 1977-03-15 | Firmenich & Cie | |
| US3897372A (en) * | 1974-04-17 | 1975-07-29 | Grace W R & Co | Smoke-flame retardant hydrophilic urethane and method |
| JPS5232916B2 (enExample) * | 1974-12-25 | 1977-08-24 | ||
| GB1546705A (en) * | 1975-06-23 | 1979-05-31 | Tenneco Chem | Production of polyurethane foam |
| JPS53106799A (en) * | 1977-03-02 | 1978-09-18 | Bridgestone Corp | Synthetic resin form and its preparation |
-
1978
- 1978-04-11 DE DE19782815554 patent/DE2815554A1/de not_active Withdrawn
-
1979
- 1979-03-12 JP JP2776479A patent/JPS54134800A/ja active Granted
- 1979-03-24 DE DE7979100894T patent/DE2967296D1/de not_active Expired
- 1979-03-24 EP EP79100894A patent/EP0004618B1/de not_active Expired
- 1979-04-09 MX MX177244A patent/MX149926A/es unknown
- 1979-04-10 CA CA000325402A patent/CA1136349A/en not_active Expired
- 1979-04-10 US US06/028,663 patent/US4258141A/en not_active Expired - Lifetime
- 1979-04-10 AT AT0267779A patent/AT379604B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| MX149926A (es) | 1984-02-09 |
| JPS6241242B2 (enExample) | 1987-09-02 |
| DE2815554A1 (de) | 1979-10-25 |
| DE2967296D1 (en) | 1984-12-20 |
| ATA267779A (de) | 1985-06-15 |
| AT379604B (de) | 1986-02-10 |
| JPS54134800A (en) | 1979-10-19 |
| US4258141A (en) | 1981-03-24 |
| EP0004618A1 (de) | 1979-10-17 |
| EP0004618B1 (de) | 1984-11-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |