JPS645027B2 - - Google Patents
Info
- Publication number
- JPS645027B2 JPS645027B2 JP52110013A JP11001377A JPS645027B2 JP S645027 B2 JPS645027 B2 JP S645027B2 JP 52110013 A JP52110013 A JP 52110013A JP 11001377 A JP11001377 A JP 11001377A JP S645027 B2 JPS645027 B2 JP S645027B2
- Authority
- JP
- Japan
- Prior art keywords
- weight
- diisocyanate
- isocyanurate
- distillation
- 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.)
- Expired
Links
- 239000005056 polyisocyanate Substances 0.000 claims description 45
- 229920001228 polyisocyanate Polymers 0.000 claims description 45
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 44
- 125000005442 diisocyanate group Chemical group 0.000 claims description 42
- 238000004821 distillation Methods 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 32
- 238000005829 trimerization reaction Methods 0.000 claims description 27
- 230000001070 adhesive effect Effects 0.000 claims description 24
- 239000000853 adhesive Substances 0.000 claims description 21
- 239000004814 polyurethane Substances 0.000 claims description 19
- 229920002635 polyurethane Polymers 0.000 claims description 19
- 239000011541 reaction mixture Substances 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 18
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 claims description 11
- 229920003052 natural elastomer Polymers 0.000 claims description 10
- 229920001194 natural rubber Polymers 0.000 claims description 10
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 229920003051 synthetic elastomer Polymers 0.000 claims description 9
- 239000005061 synthetic rubber Substances 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 7
- 239000000025 natural resin Substances 0.000 claims description 6
- MGYGFNQQGAQEON-UHFFFAOYSA-N 4-tolyl isocyanate Chemical compound CC1=CC=C(N=C=O)C=C1 MGYGFNQQGAQEON-UHFFFAOYSA-N 0.000 claims description 5
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 claims description 5
- 239000000057 synthetic resin Substances 0.000 claims description 5
- 229920003002 synthetic resin Polymers 0.000 claims description 5
- 239000012467 final product Substances 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 235000014593 oils and fats Nutrition 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 35
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000012948 isocyanate Substances 0.000 description 18
- 238000012360 testing method Methods 0.000 description 17
- 150000002513 isocyanates Chemical class 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- -1 hydroxyl compound Chemical class 0.000 description 10
- 229910052740 iodine Inorganic materials 0.000 description 10
- 239000011630 iodine Substances 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 239000010409 thin film Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 150000007973 cyanuric acids Chemical class 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- 239000004922 lacquer Substances 0.000 description 5
- 239000002574 poison Substances 0.000 description 5
- 231100000614 poison Toxicity 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920001084 poly(chloroprene) Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920000582 polyisocyanurate Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 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 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- 241001441571 Hiodontidae Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 229920005830 Polyurethane Foam Polymers 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 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
- 239000011495 polyisocyanurate Substances 0.000 description 2
- 239000011496 polyurethane foam Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- NTKBNCABAMQDIG-UHFFFAOYSA-N trimethylene glycol-monobutyl ether Natural products CCCCOCCCO NTKBNCABAMQDIG-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-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
- LTIKIBFTASQKMM-UHFFFAOYSA-N 1-[bis(4-isocyanatophenyl)methyl]-4-isocyanatobenzene Chemical compound C1=CC(N=C=O)=CC=C1C(C=1C=CC(=CC=1)N=C=O)C1=CC=C(N=C=O)C=C1 LTIKIBFTASQKMM-UHFFFAOYSA-N 0.000 description 1
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
- JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical compound O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- IXEHTHNYIWZCSI-UHFFFAOYSA-N 2,2,3-trichlorocyclopropan-1-one Chemical class ClC1C(=O)C1(Cl)Cl IXEHTHNYIWZCSI-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- QXGBIHFUXMYJEF-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.N=C=O.C(C1=CC=CC=C1)C1=CC=CC=C1 Chemical class N=C=O.N=C=O.N=C=O.N=C=O.C(C1=CC=CC=C1)C1=CC=CC=C1 QXGBIHFUXMYJEF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- YYQRGCZGSFRBAM-UHFFFAOYSA-N Triclofos Chemical compound OP(O)(=O)OCC(Cl)(Cl)Cl YYQRGCZGSFRBAM-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- FZWBABZIGXEXES-UHFFFAOYSA-N ethane-1,2-diol;hexanedioic acid Chemical compound OCCO.OC(=O)CCCCC(O)=O FZWBABZIGXEXES-UHFFFAOYSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 150000004676 glycans Chemical class 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
- 238000010438 heat treatment Methods 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- DUDXQIXWPJMPRQ-UHFFFAOYSA-N isocyanatomethylcyclohexane Chemical compound O=C=NCC1CCCCC1 DUDXQIXWPJMPRQ-UHFFFAOYSA-N 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 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
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- XLKZJJVNBQCVIX-UHFFFAOYSA-N tetradecane-1,14-diol Chemical compound OCCCCCCCCCCCCCCO XLKZJJVNBQCVIX-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000003579 thiophosphoric acid derivatives Chemical class 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
- OACSUWPJZKGHHK-UHFFFAOYSA-N tribenzyl phosphate Chemical compound C=1C=CC=CC=1COP(OCC=1C=CC=CC=1)(=O)OCC1=CC=CC=C1 OACSUWPJZKGHHK-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 229960001147 triclofos Drugs 0.000 description 1
- SFENPMLASUEABX-UHFFFAOYSA-N trihexyl phosphate Chemical compound CCCCCCOP(=O)(OCCCCCC)OCCCCCC SFENPMLASUEABX-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J121/00—Adhesives based on unspecified rubbers
-
- 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
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2641380A DE2641380C2 (de) | 1976-09-15 | 1976-09-15 | Verfahren zur Herstellung von Polyisocyanaten mit Isocyanuratstruktur |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5335799A JPS5335799A (en) | 1978-04-03 |
| JPS645027B2 true JPS645027B2 (en:Method) | 1989-01-27 |
Family
ID=5987894
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11001377A Granted JPS5335799A (en) | 1976-09-15 | 1977-09-14 | Process for producing polyisocyanate with isocyanurate structure and use thereof |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4255569A (en:Method) |
| JP (1) | JPS5335799A (en:Method) |
| BE (1) | BE858675A (en:Method) |
| BR (1) | BR7706125A (en:Method) |
| CA (1) | CA1080224A (en:Method) |
| DE (1) | DE2641380C2 (en:Method) |
| ES (1) | ES462357A1 (en:Method) |
| FR (1) | FR2364908A1 (en:Method) |
| GB (1) | GB1551890A (en:Method) |
| IT (1) | IT1091137B (en:Method) |
| MX (1) | MX146303A (en:Method) |
Families Citing this family (134)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1112243A (en) * | 1978-09-08 | 1981-11-10 | Manfred Bock | Process for the preparation of polyisocyanates containing isocyanurate groups and the use thereof |
| DE3033860A1 (de) * | 1980-09-09 | 1982-04-15 | Bayer Ag, 5090 Leverkusen | Neue isocyanato-isocyanurate, ein verfahren zu ihrer herstellung, sowie ihre verwendung als isocyanatkomponente in polyurethanlacken |
| DE3100263A1 (de) * | 1981-01-08 | 1982-08-12 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung bei der herstellung von polyurethanen |
| DE3100262A1 (de) * | 1981-01-08 | 1982-08-05 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten, als katalysator-komponente fuer dieses verfahren geeignete loesungen, sowie die verwendung der verfahrensprodukte als isocyanat-komponente bei der herstellung von polyurethanen |
| US4359541A (en) * | 1981-01-19 | 1982-11-16 | Basf Wyandotte Corporation | Process for the preparation of polyisocyanurate dispersions and compositions prepared therefrom |
| US4359550A (en) * | 1981-01-19 | 1982-11-16 | Basf Wyandotte Corporation | Polyisocyanurate polymers, dispersions, and cellular and non-cellular polyurethane products prepared therefrom |
| US4326043A (en) * | 1981-01-19 | 1982-04-20 | Basf Wyandotte Corporation | Process for the preparation of polyisocyanurate dispersions modified with halogenated alcohols and compositions prepared therefrom |
| DE3144672A1 (de) * | 1981-11-10 | 1983-05-26 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von mischtrimerisaten organischer isocyanate, die nach dem verfahren erhaltenen mischtrimerisate, sowie ihre verwendung zur herstellung von polyurethanen |
| DE3227489A1 (de) * | 1982-07-23 | 1984-01-26 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung als isocyanatkomponente zur herstellung von polyurethanen |
| DE3303221A1 (de) * | 1983-02-01 | 1984-08-02 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten, die nach diesem verfahren erhaeltlichen verbindungen und ihre verwendung zur herstellung von polyurethanen |
| DE3339579A1 (de) * | 1983-11-02 | 1985-05-09 | Bayer Ag, 5090 Leverkusen | Neue isocyanato-isocyanurate, ein verfahren zu ihrer herstellung sowie ihre verwendung als isocyanat-komponente in polyurethanlacken |
| JPS61151179A (ja) * | 1984-12-25 | 1986-07-09 | Mitsui Toatsu Chem Inc | ヘキサメチレンイソシアヌラ−ト化合物の製造方法 |
| US4607103A (en) * | 1985-08-13 | 1986-08-19 | General Electric Company, Silicone Products Division | Methods for making blocked isocyanurates |
| DE3543925A1 (de) * | 1985-12-12 | 1987-06-19 | Bayer Ag | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung als isocyanatkomponente zur herstellung von polyurethanen |
| DE3910100C1 (en:Method) * | 1989-03-29 | 1990-01-04 | Bayer Ag, 5090 Leverkusen, De | |
| DE4104436A1 (de) * | 1991-02-14 | 1992-08-20 | Bayer Ag | Vernetzer fuer polymere klebstoffe |
| DE4428107A1 (de) * | 1994-08-09 | 1996-02-15 | Bayer Ag | Lackpolyisocyanate mit aliphatisch und aromatisch gebundenen Isocyanatgruppen |
| JP4636422B2 (ja) * | 2000-02-14 | 2011-02-23 | 日本ポリウレタン工業株式会社 | ポリイソシアネート硬化剤、その製造方法および該硬化剤を用いたラミネート用形成性接着剤組成物 |
| DE10025304A1 (de) * | 2000-05-22 | 2001-11-29 | Bayer Ag | Mischungen wässriger Bindemittel |
| DE10100220A1 (de) * | 2001-01-04 | 2002-07-11 | Basf Ag | Holzwerkstoffe aus mit Polyisocyanaten verleimten Holzteilen |
| DE10103027A1 (de) | 2001-01-24 | 2002-07-25 | Bayer Ag | Zweikomponenten-Polyurethan-Bindemittel als Haftvermittler |
| US6515125B1 (en) | 2001-03-09 | 2003-02-04 | Bayer Corporation | Liquid partially trimerized polyisocyanates based on toluene diisocyanate and diphenylmethane diisocyanate |
| DE10328663A1 (de) * | 2003-06-26 | 2005-01-13 | Bayer Materialscience Ag | Polyisocyanat-modifizierte Polycarbonsäuren |
| US20050101754A1 (en) * | 2003-11-12 | 2005-05-12 | Slack William E. | Stable liquid, allophanate-modified diphenylmethane diisocyanate trimers, prepolymers thereof, and processes for their preparation |
| DE102006053740A1 (de) | 2006-11-15 | 2008-05-21 | Bayer Materialscience Ag | Beschichtungsmittel |
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| CN115466201B (zh) | 2021-06-11 | 2024-05-03 | 万华化学集团股份有限公司 | 一种磺酸改性多异氰酸酯及其制备方法 |
| EP4105251A1 (de) | 2021-06-18 | 2022-12-21 | Covestro Deutschland AG | Vernetzbare zusammensetzungen, enthaltend imin- und/oder aminal-bildende komponenten |
| WO2022263306A1 (de) | 2021-06-18 | 2022-12-22 | Covestro Deutschland Ag | Organische polyisocyanate mit aldehydblockierung |
| EP4108695A1 (de) | 2021-06-21 | 2022-12-28 | Covestro Deutschland AG | Beschichtungsmittel und daraus erhältliche beschichtungen mit verbesserten anschmutzungsresistenzen und (selbst-)reinigungseigenschaften |
| EP4108694A1 (de) | 2021-06-21 | 2022-12-28 | Covestro Deutschland AG | Beschichtungsmittel und daraus erhältliche beschichtungen mit verbesserten anschmutzungsresistenzen und (selbst-)reinigungseigenschaften |
| EP4373871A1 (en) | 2021-07-23 | 2024-05-29 | Sika Technology AG | Polyisocyanurate plastics with high transparency |
| EP4169962A1 (en) | 2021-10-21 | 2023-04-26 | Covestro Deutschland AG | Encapsulated polyurethane polymerization catalyst and latent reactive polyurethane composition |
| EP4198094A1 (de) | 2021-12-20 | 2023-06-21 | Covestro Deutschland AG | Mehrschichtaufbau auf metallischen untergründen basierend auf polyaspartatbeschichtungen |
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| EP4282894A1 (de) | 2022-05-25 | 2023-11-29 | Covestro Deutschland AG | Einkomponenten- einbrennsystem |
| WO2024000342A1 (zh) | 2022-06-30 | 2024-01-04 | 万华化学集团股份有限公司 | 一种亲水改性聚异氰酸酯及其制备方法和应用 |
| EP4602090A1 (en) | 2022-10-13 | 2025-08-20 | Covestro Deutschland AG | Solid surface materials based on reaction mixtures with two kind of blowing agents |
| EP4375307A1 (en) | 2022-11-23 | 2024-05-29 | Covestro Deutschland AG | Solid surface materials based on reaction mixtures with two kind of blowing agents |
| EP4406987A1 (en) | 2023-01-27 | 2024-07-31 | Sika Technology AG | Curable potting material for automotive battery packs |
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| EP4480979A1 (en) | 2023-06-20 | 2024-12-25 | Covestro Deutschland AG | Polyisocyanate composition |
| WO2024260926A1 (en) | 2023-06-22 | 2024-12-26 | Covestro Deutschland Ag | Method for the production of a hydroxyl-group terminated oxazolidinone composition |
| EP4506166A1 (de) | 2023-08-10 | 2025-02-12 | Covestro Deutschland AG | Verfahren zur herstellung eines recyclefähigen monomaterial-mehrschichtsystems |
| EP4512839A1 (de) | 2023-08-25 | 2025-02-26 | Covestro Deutschland AG | Wasserbasierte strahlenhärtbare polyurethandispersionen mit hervorragenden anwendungstechnischen eigenschaften |
| WO2025108924A1 (en) | 2023-11-21 | 2025-05-30 | Covestro Deutschland Ag | Water-dispersible blocked isocyanate prepolymer system, method for preparing the same, and application thereof |
| EP4559946A1 (de) | 2023-11-21 | 2025-05-28 | Covestro Deutschland AG | Blockierte polyisocyanate |
| WO2025108919A1 (en) | 2023-11-21 | 2025-05-30 | Covestro Deutschland Ag | Blocked isocyanate prepolymer system, method for preparing the same, and application thereof |
| EP4574860A1 (en) | 2023-12-19 | 2025-06-25 | Covestro Deutschland AG | Use of a solvent-free composition comprising epoxy-functional oxazolidinones for producing adhesives, sealing compounds, potting compounds, composites, such as fiber composite materials, or moldings, or for producing coatings on mineral, metallic or plastic substrates, and the products thus obtained |
| EP4574864A1 (de) | 2023-12-19 | 2025-06-25 | Covestro Deutschland AG | Polyisocyanatgemisch |
| EP4574870A1 (de) | 2023-12-19 | 2025-06-25 | Covestro Deutschland AG | Blockiertes polyisocyanat |
| EP4574863A1 (de) | 2023-12-19 | 2025-06-25 | Covestro Deutschland AG | Polyisocyanatgemisch |
| EP4640732A1 (de) | 2024-04-25 | 2025-10-29 | Covestro Deutschland AG | Ein-komponenten-system für beschichtungen |
| EP4640731A1 (de) | 2024-04-25 | 2025-10-29 | Covestro Deutschland AG | Ein-komponenten-beschichtungsmittel für nahrungsmittelbehälter |
| WO2025233647A1 (en) | 2024-05-08 | 2025-11-13 | Sika Technology Ag | Battery box comprising a foamed polisocyanurate material |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2952665A (en) * | 1955-12-08 | 1960-09-13 | Mobay Chemical Corp | High molecular weight cyclic trimers containing blocked isocyanate groups |
| DE1125652B (de) * | 1956-11-16 | 1962-03-15 | Ici Ltd | Verfahren zur Herstellung von haertbaren polymeren organischen Isocyanaten |
| GB952931A (en) * | 1961-05-25 | 1964-03-18 | Ici Ltd | Improved polyisocyanate compositions |
| FR1337621A (fr) * | 1961-10-17 | 1963-09-13 | Ici Ltd | Nouveaux polymères à structure isocyanurate |
| BE623676A (en:Method) * | 1961-10-17 | |||
| DE1203792B (de) * | 1963-05-17 | 1965-10-28 | Bayer Ag | Verfahren zur Herstellung von Isocyanursaeure-derivaten durch katalytische Polymerisation von organischen Isocyanaten |
| US3526624A (en) * | 1966-03-04 | 1970-09-01 | Marathon Oil Co | Production of urethane-containing compositions |
| US3517002A (en) * | 1966-11-17 | 1970-06-23 | Mobay Chemical Corp | Polyisocyanates containing isocyanurate groups |
| US3619338A (en) * | 1968-05-14 | 1971-11-09 | Monsanto Res Corp | Glass fabric sheets bonded together with polyisocyanurates prepared from an organic diisocyanate and a monoisocyanate using ionic polymerization catalysts |
| US3641024A (en) * | 1968-11-01 | 1972-02-08 | Marathon Oil Co | Low molecular weight polyisocyanates |
| US3631000A (en) * | 1969-06-04 | 1971-12-28 | Marathon Oil Co | Isocyanurate-containing polyisocyanates and method of preparation |
| US3773695A (en) * | 1969-06-04 | 1973-11-20 | Marathon Oil Co | Isocyanurate and halogen-containing polyisocyanates |
| DE2325826C3 (de) * | 1973-05-22 | 1981-01-29 | Chemische Werke Huels Ag, 4370 Marl | Isocyanato-isocyanurate und Herstellung lagerstabiler Lösungen hiervon |
| US3860673A (en) * | 1973-07-31 | 1975-01-14 | Du Pont | Elastomeric compositions |
| DE2452532C3 (de) * | 1974-11-06 | 1978-08-24 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Polyisocyanaten mit Isocyanurat-Struktur |
-
1976
- 1976-09-15 DE DE2641380A patent/DE2641380C2/de not_active Expired
-
1977
- 1977-09-09 GB GB37711/77A patent/GB1551890A/en not_active Expired
- 1977-09-13 MX MX170550A patent/MX146303A/es unknown
- 1977-09-13 IT IT50994/77A patent/IT1091137B/it active
- 1977-09-14 BE BE180886A patent/BE858675A/xx not_active IP Right Cessation
- 1977-09-14 CA CA286,761A patent/CA1080224A/en not_active Expired
- 1977-09-14 JP JP11001377A patent/JPS5335799A/ja active Granted
- 1977-09-14 ES ES462357A patent/ES462357A1/es not_active Expired
- 1977-09-14 BR BR7706125A patent/BR7706125A/pt unknown
- 1977-09-15 FR FR7727917A patent/FR2364908A1/fr active Granted
-
1979
- 1979-05-04 US US06/036,128 patent/US4255569A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE2641380C2 (de) | 1989-11-23 |
| US4255569A (en) | 1981-03-10 |
| DE2641380A1 (de) | 1978-03-16 |
| ES462357A1 (es) | 1978-06-16 |
| BE858675A (fr) | 1978-03-14 |
| GB1551890A (en) | 1979-09-05 |
| BR7706125A (pt) | 1978-07-04 |
| FR2364908A1 (fr) | 1978-04-14 |
| CA1080224A (en) | 1980-06-24 |
| JPS5335799A (en) | 1978-04-03 |
| MX146303A (es) | 1982-06-03 |
| FR2364908B1 (en:Method) | 1983-01-07 |
| IT1091137B (it) | 1985-06-26 |
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