CA1269481A - Thermosetting resin and a method for producing it - Google Patents
Thermosetting resin and a method for producing itInfo
- Publication number
- CA1269481A CA1269481A CA000505286A CA505286A CA1269481A CA 1269481 A CA1269481 A CA 1269481A CA 000505286 A CA000505286 A CA 000505286A CA 505286 A CA505286 A CA 505286A CA 1269481 A CA1269481 A CA 1269481A
- Authority
- CA
- Canada
- Prior art keywords
- thermosetting resin
- accelerating
- isocyanate
- organic
- diisocyanate
- 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 - Lifetime
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 106
- 239000011347 resin Substances 0.000 title claims abstract description 106
- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 67
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 76
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 38
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 38
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 38
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 22
- 238000005829 trimerization reaction Methods 0.000 claims abstract description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
- 150000001718 carbodiimides Chemical class 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims description 69
- 239000000203 mixture Substances 0.000 claims description 54
- 239000012948 isocyanate Substances 0.000 claims description 44
- 239000003054 catalyst Substances 0.000 claims description 43
- 150000002513 isocyanates Chemical class 0.000 claims description 39
- 238000010438 heat treatment Methods 0.000 claims description 24
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical group C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 21
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 21
- 239000004593 Epoxy Substances 0.000 claims description 20
- 238000000465 moulding Methods 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- -1 inorganic acid salts Chemical class 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 13
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical group N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 claims description 13
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical group O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 12
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 12
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 claims description 9
- 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 8
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical group C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 claims description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 7
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 claims description 7
- 239000012973 diazabicyclooctane Substances 0.000 claims description 7
- 229920003986 novolac Polymers 0.000 claims description 7
- 229930185605 Bisphenol Natural products 0.000 claims description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 6
- AUABZJZJXPSZCN-UHFFFAOYSA-N 2-(dimethylamino)phenol Chemical compound CN(C)C1=CC=CC=C1O AUABZJZJXPSZCN-UHFFFAOYSA-N 0.000 claims description 5
- BZUILZIKDIMXBK-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxycarbonyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OCC1OC1 BZUILZIKDIMXBK-UHFFFAOYSA-N 0.000 claims description 5
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 claims description 5
- 239000003365 glass fiber Substances 0.000 claims description 5
- 229920001568 phenolic resin Polymers 0.000 claims description 5
- 239000008096 xylene Substances 0.000 claims description 5
- JVVRCYWZTJLJSG-UHFFFAOYSA-N 4-dimethylaminophenol Chemical compound CN(C)C1=CC=C(O)C=C1 JVVRCYWZTJLJSG-UHFFFAOYSA-N 0.000 claims description 4
- 239000007983 Tris buffer Substances 0.000 claims description 4
- 238000004132 cross linking Methods 0.000 claims description 4
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 230000002787 reinforcement Effects 0.000 claims description 4
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 claims description 3
- JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical class O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-UHFFFAOYSA-N 0.000 claims description 3
- RQBUVIFBALZGPC-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanatophenyl)benzene Chemical compound C1=CC(N=C=O)=CC=C1C1=CC=C(N=C=O)C=C1 RQBUVIFBALZGPC-UHFFFAOYSA-N 0.000 claims description 3
- DTZHXCBUWSTOPO-UHFFFAOYSA-N 1-isocyanato-4-[(4-isocyanato-3-methylphenyl)methyl]-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(CC=2C=C(C)C(N=C=O)=CC=2)=C1 DTZHXCBUWSTOPO-UHFFFAOYSA-N 0.000 claims description 3
- KNHJIEOCVVIBIV-UHFFFAOYSA-N 2,3-dimethylphenyl isocyanate Chemical compound CC1=CC=CC(N=C=O)=C1C KNHJIEOCVVIBIV-UHFFFAOYSA-N 0.000 claims description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 3
- IXQBIOPGDNZYNA-UHFFFAOYSA-N N=C=O.N=C=O.CC1=CC=CC=C1C1=CC=CC=C1C Chemical compound N=C=O.N=C=O.CC1=CC=CC=C1C1=CC=CC=C1C IXQBIOPGDNZYNA-UHFFFAOYSA-N 0.000 claims description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 239000001569 carbon dioxide Substances 0.000 claims description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 3
- 235000011056 potassium acetate Nutrition 0.000 claims description 3
- 239000001632 sodium acetate Substances 0.000 claims description 3
- 235000017281 sodium acetate Nutrition 0.000 claims description 3
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 claims description 3
- 239000004299 sodium benzoate Substances 0.000 claims description 3
- 235000010234 sodium benzoate Nutrition 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- LKLLNYWECKEQIB-UHFFFAOYSA-N 1,3,5-triazinane Chemical compound C1NCNCN1 LKLLNYWECKEQIB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- 125000005442 diisocyanate group Chemical group 0.000 claims 24
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims 6
- 230000001276 controlling effect Effects 0.000 claims 5
- 229910000071 diazene Inorganic materials 0.000 claims 5
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical group C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims 2
- SPTUBPSDCZNVSI-UHFFFAOYSA-N N=C=O.N=C=O.COC1=CC=CC=C1C1=CC=CC=C1OC Chemical compound N=C=O.N=C=O.COC1=CC=CC=C1C1=CC=CC=C1OC SPTUBPSDCZNVSI-UHFFFAOYSA-N 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 239000005011 phenolic resin Substances 0.000 claims 2
- 229960003885 sodium benzoate Drugs 0.000 claims 2
- OQMSRJDECXBSRF-UHFFFAOYSA-N 1,5-bis(oxiran-2-ylmethyl)cyclohexa-2,4-dien-1-amine Chemical compound C(C1CO1)C1(N)CC(=CC=C1)CC1CO1 OQMSRJDECXBSRF-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims 1
- 238000006358 imidation reaction Methods 0.000 claims 1
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 46
- 239000006260 foam Substances 0.000 description 32
- 230000000704 physical effect Effects 0.000 description 29
- 239000000843 powder Substances 0.000 description 23
- 239000000126 substance Substances 0.000 description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 15
- 239000001301 oxygen Substances 0.000 description 15
- 229910052760 oxygen Inorganic materials 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- 239000011521 glass Substances 0.000 description 8
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 8
- 238000002411 thermogravimetry Methods 0.000 description 7
- 238000013019 agitation Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- YMKWWHFRGALXLE-UHFFFAOYSA-N 4-methyl-1-phenyl-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound C1CC(C)=CP1(=O)C1=CC=CC=C1 YMKWWHFRGALXLE-UHFFFAOYSA-N 0.000 description 5
- 239000012261 resinous substance Substances 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- WCTWAAFIWRIEKH-UHFFFAOYSA-N 1-ethyl-4-methyl-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound CCP1(=O)CCC(C)=C1 WCTWAAFIWRIEKH-UHFFFAOYSA-N 0.000 description 3
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 239000004570 mortar (masonry) Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012778 molding material Substances 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- LUYHWJKHJNFYGV-UHFFFAOYSA-N 1,2-diisocyanato-3-phenylbenzene Chemical compound O=C=NC1=CC=CC(C=2C=CC=CC=2)=C1N=C=O LUYHWJKHJNFYGV-UHFFFAOYSA-N 0.000 description 1
- KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical compound NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NOHQUGRVHSJYMR-UHFFFAOYSA-N 1-chloro-2-isocyanatobenzene Chemical compound ClC1=CC=CC=C1N=C=O NOHQUGRVHSJYMR-UHFFFAOYSA-N 0.000 description 1
- IOSIDVPNBKUUFA-UHFFFAOYSA-N 1-ethyl-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound CCP1(=O)CCC=C1 IOSIDVPNBKUUFA-UHFFFAOYSA-N 0.000 description 1
- QZTWVDCKDWZCLV-UHFFFAOYSA-N 1-isocyanato-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(N=C=O)C=C1 QZTWVDCKDWZCLV-UHFFFAOYSA-N 0.000 description 1
- BDQNKCYCTYYMAA-UHFFFAOYSA-N 1-isocyanatonaphthalene Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1 BDQNKCYCTYYMAA-UHFFFAOYSA-N 0.000 description 1
- JQSYESKKWJGZQV-UHFFFAOYSA-N 1-phenyl-1-sulfanylidene-2,3-dihydro-1$l^{5}-phosphole Chemical compound C=1C=CC=CC=1P1(=S)CCC=C1 JQSYESKKWJGZQV-UHFFFAOYSA-N 0.000 description 1
- YUQUHJGNZFFDAA-UHFFFAOYSA-N 1-phenyl-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound C=1C=CC=CC=1P1(=O)CCC=C1 YUQUHJGNZFFDAA-UHFFFAOYSA-N 0.000 description 1
- NBNGHXWJFSMASY-UHFFFAOYSA-N 2,3,4-tris(dimethylamino)phenol Chemical compound CN(C)C1=CC=C(O)C(N(C)C)=C1N(C)C NBNGHXWJFSMASY-UHFFFAOYSA-N 0.000 description 1
- JXGNHEUFHNJWDY-UHFFFAOYSA-N 2,5-dihydro-1h-phosphole Chemical class C1PCC=C1 JXGNHEUFHNJWDY-UHFFFAOYSA-N 0.000 description 1
- LXCZZZLQISLGGM-UHFFFAOYSA-N 2-methyl-1h-triazine-4,6-diamine Chemical compound CN1NC(N)=CC(N)=N1 LXCZZZLQISLGGM-UHFFFAOYSA-N 0.000 description 1
- CKYZEOPDJVLBTQ-UHFFFAOYSA-N 3,4-dihydro-4-methyl-2h-phosphole 1-oxide Chemical compound CC1CCP(=O)=C1 CKYZEOPDJVLBTQ-UHFFFAOYSA-N 0.000 description 1
- DBZGWWBWDYGSRA-UHFFFAOYSA-N 3-methyl-1-phenyl-2,5-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound C1C(C)=CCP1(=O)C1=CC=CC=C1 DBZGWWBWDYGSRA-UHFFFAOYSA-N 0.000 description 1
- OJZDWCDQNYUXQP-UHFFFAOYSA-N 4-methyl-1-phenyl-2,3-dihydrophosphole Chemical compound C1CC(C)=CP1C1=CC=CC=C1 OJZDWCDQNYUXQP-UHFFFAOYSA-N 0.000 description 1
- MGYGFNQQGAQEON-UHFFFAOYSA-N 4-tolyl isocyanate Chemical compound CC1=CC=C(N=C=O)C=C1 MGYGFNQQGAQEON-UHFFFAOYSA-N 0.000 description 1
- ZBYGQPNRQOEQHF-UHFFFAOYSA-N 5-methyl-1-phenyl-2,3-dihydrophosphole Chemical compound CC1=CCCP1C1=CC=CC=C1 ZBYGQPNRQOEQHF-UHFFFAOYSA-N 0.000 description 1
- DUZLHGMYNVZMCO-UHFFFAOYSA-N 6-[2-[3-[2-(4,6-diamino-1,3,5-triazin-2-yl)ethyl]-2,4,8,10-tetraoxaspiro[5.5]undecan-9-yl]ethyl]-1,3,5-triazine-2,4-diamine Chemical group NC1=NC(N)=NC(CCC2OCC3(CO2)COC(CCC=2N=C(N)N=C(N)N=2)OC3)=N1 DUZLHGMYNVZMCO-UHFFFAOYSA-N 0.000 description 1
- STUPVELWKGXMQS-UHFFFAOYSA-N CC1=CP(=O)CC1 Chemical compound CC1=CP(=O)CC1 STUPVELWKGXMQS-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical class N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- NJLLQSBAHIKGKF-UHFFFAOYSA-N dipotassium dioxido(oxo)titanium Chemical compound [K+].[K+].[O-][Ti]([O-])=O NJLLQSBAHIKGKF-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000007731 hot pressing Methods 0.000 description 1
- 150000002483 hydrogen compounds Chemical class 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- MLRDQVPGKNANCJ-UHFFFAOYSA-N oxolane;1,1,2-trichloroethene Chemical group C1CCOC1.ClC=C(Cl)Cl MLRDQVPGKNANCJ-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UGQZLDXDWSPAOM-UHFFFAOYSA-N pyrrolo[3,4-f]isoindole-1,3,5,7-tetrone Chemical compound C1=C2C(=O)NC(=O)C2=CC2=C1C(=O)NC2=O UGQZLDXDWSPAOM-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 238000004260 weight control Methods 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
-
- 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
- C08G18/09—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture
- C08G18/095—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture oligomerisation to carbodiimide or uretone-imine 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
- C08G18/003—Polymeric products of isocyanates or isothiocyanates with epoxy compounds having no active hydrogen
-
- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/58—Epoxy resins
-
- 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
-
- 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
- C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine 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
- 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
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)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000505286A CA1269481A (en) | 1985-03-29 | 1986-03-27 | Thermosetting resin and a method for producing it |
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60/66295 | 1985-03-29 | ||
| JP60066195A JPS61235414A (ja) | 1985-03-29 | 1985-03-29 | 熱硬化性樹脂の製造方法 |
| JP60076656A JPS61235415A (ja) | 1985-04-12 | 1985-04-12 | 熱硬化性樹脂の製造方法 |
| JP60/76656 | 1985-04-12 | ||
| JP60087460A JPS61246245A (ja) | 1985-04-25 | 1985-04-25 | 熱硬化性樹脂の製造方法 |
| JP60/87460 | 1985-04-25 | ||
| JP60/108359 | 1985-05-22 | ||
| JP60108359A JPS61268714A (ja) | 1985-05-22 | 1985-05-22 | 耐熱性の高い熱硬化性樹脂の製造方法 |
| JP60140491A JPS621714A (ja) | 1985-06-28 | 1985-06-28 | 熱硬化性樹脂の製造方法 |
| JP60/140491 | 1985-06-28 | ||
| CA000505286A CA1269481A (en) | 1985-03-29 | 1986-03-27 | Thermosetting resin and a method for producing it |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA1269481C CA1269481C (en) | 1990-05-22 |
| CA1269481A true CA1269481A (en) | 1990-05-22 |
Family
ID=27523966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000505286A Expired - Lifetime CA1269481A (en) | 1985-03-29 | 1986-03-27 | Thermosetting resin and a method for producing it |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US5079326A (en, 2012) |
| KR (1) | KR900008986B1 (en, 2012) |
| CA (1) | CA1269481A (en, 2012) |
| DE (4) | DE3643239C2 (en, 2012) |
| FR (1) | FR2579600B1 (en, 2012) |
| GB (3) | GB2177710B (en, 2012) |
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|---|---|---|---|---|
| NL8821115A (nl) * | 1988-12-26 | 1990-12-03 | V Elektrotekhnicheskogo I Im V | Samenstelling voor elektrisch isolatiemateriaal. |
| GB8902228D0 (en) * | 1989-02-01 | 1989-03-22 | Ici Plc | Carbodiimide-isocyanurate rigid foams |
| DE3932168A1 (de) * | 1989-09-27 | 1991-04-04 | Bayer Ag | Lackpolyisocyanate, ein verfahren zu ihrer herstellung und ihre verwendung |
| US6333101B1 (en) * | 1992-02-28 | 2001-12-25 | Nisshinbo Industries, Inc. | Method of adhering adherends |
| EP0585636B1 (en) * | 1992-08-06 | 1997-05-28 | Nisshinbo Industries, Inc. | Method for producing modified polyisocyanurate foams |
| US5321050A (en) * | 1992-08-06 | 1994-06-14 | Nisshinbo Industries, Inc. | Method for producing modified polyisocyanurate foams |
| JP3188959B2 (ja) * | 1992-08-10 | 2001-07-16 | 日清紡績株式会社 | ポリカルボジイミド樹脂の製造方法 |
| JP2604953B2 (ja) * | 1992-10-23 | 1997-04-30 | 日清紡績株式会社 | 変性ポリイソシアヌレート発泡体の製造法 |
| ATE170540T1 (de) * | 1992-11-20 | 1998-09-15 | Dow Chemical Co | Verbesserte hochtemperaturstabilitätaufweisende polyharnstoffpolymere sowie verfahren zu deren herstellung |
| JP3422857B2 (ja) * | 1994-04-04 | 2003-06-30 | 保土谷化学工業株式会社 | 広いゴム領域を有する熱可塑性ポリウレタン樹脂及びその製造法 |
| JPH0827092A (ja) * | 1994-07-15 | 1996-01-30 | Nisshinbo Ind Inc | ウレア変性カルボジイミド及びその製造方法 |
| JP3708567B2 (ja) * | 1994-07-20 | 2005-10-19 | 日清紡績株式会社 | 生物学的に活性な物質を固定するための方法 |
| US5576398A (en) * | 1995-07-07 | 1996-11-19 | Japan Synthetic Rubber Co., Ltd. | Thermosetting resin composition |
| DE69611718T2 (de) * | 1995-12-05 | 2001-06-07 | Shin-Etsu Chemical Co., Ltd. | Verfahren zur Herstellung von vernetzten Polycarbodiimiden |
| US5821325A (en) * | 1995-12-12 | 1998-10-13 | Shin-Estu Chemical Co., Ltd. | Polycarbodiimide derivatives and method for preparing the same |
| US5612791A (en) | 1995-12-12 | 1997-03-18 | Xerox Corporation | Bound document imager with air jet page turning system |
| US5640252A (en) | 1995-12-12 | 1997-06-17 | Xerox Corporation | Bound document imager with page turner |
| US5770661A (en) * | 1996-01-16 | 1998-06-23 | Shin-Etsu Chemical Co., Ltd. | Polycarbodiimide derivative and process for producing the same |
| DE19728411C2 (de) * | 1997-07-03 | 2001-09-27 | Basf Coatings Ag | Polyurethanharz, Verfahren zu seiner Herstellung und seine Verwendung in wäßrigen Zweikomponenten-Klarlacken |
| JP4037958B2 (ja) | 1998-05-11 | 2008-01-23 | 日清紡績株式会社 | 熱硬化性樹脂組成物 |
| JP3472156B2 (ja) * | 1998-09-30 | 2003-12-02 | 日清紡績株式会社 | 電子部品用フィルム状封止剤 |
| JP2003259491A (ja) * | 2002-03-04 | 2003-09-12 | Nisshinbo Ind Inc | 音響整合層用組成物、音響整合層成形品の製造方法及びそれらを用いる超音波センサー |
| JP3868341B2 (ja) * | 2002-04-22 | 2007-01-17 | 日清紡績株式会社 | 耐熱性に優れたプラズマエッチング電極及びそれを装着したドライエッチング装置 |
| JP2004238441A (ja) * | 2003-02-04 | 2004-08-26 | Nitto Denko Corp | 光半導体素子封止用樹脂 |
| JP4249996B2 (ja) * | 2003-02-10 | 2009-04-08 | 日東電工株式会社 | ポリカルボジイミド共重合体からなるレンズ材料 |
| EP1649322A4 (en) * | 2003-07-17 | 2007-09-19 | Honeywell Int Inc | PLANARIZATION FILMS FOR ADVANCED MICRO-ELECTRONIC APPLICATIONS AND EQUIPMENT AND METHOD FOR THE PRODUCTION THEREOF |
| CN1638585A (zh) * | 2003-12-26 | 2005-07-13 | 日东电工株式会社 | 电致发光装置，平面光源和使用该平面光源的显示器 |
| NL1031053C2 (nl) * | 2006-02-02 | 2007-08-03 | Stahl Int Bv | Werkwijze voor de bereiding van dispersies van vernettingsmiddelen in water. |
| EP2418247A1 (de) * | 2010-08-11 | 2012-02-15 | Rhein Chemie Rheinau GmbH | Langlebige biobasierte Kunststoffe, ein Verfahren zu deren Herstellung und deren Verwendung |
| TWI500701B (zh) * | 2012-10-08 | 2015-09-21 | Rohm & Haas | 芳香族碳二醯亞胺之固化 |
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| CN106715578B (zh) | 2014-09-11 | 2019-05-10 | 帝人株式会社 | 热固化性树脂组合物 |
| US10058502B2 (en) | 2015-12-31 | 2018-08-28 | L'oreal | Nail polish compositions |
| CN107778774B (zh) * | 2016-08-31 | 2021-04-06 | 洛阳尖端技术研究院 | 一种环氧树脂胶膜及其制备方法 |
| KR20210135584A (ko) | 2019-03-07 | 2021-11-15 | 바스프 에스이 | 카르보디아미드 화학 기반의 접착제 |
| WO2025067942A1 (en) | 2023-09-25 | 2025-04-03 | Basf Se | Thermally conductive two component resin based on carbodiimide chemistry |
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| US4542165A (en) * | 1983-09-08 | 1985-09-17 | Sanyo Chemical Industries, Ltd. | Polyurethane based on epoxy-containing polymer polyol and process for making the same |
| DE3347659A1 (de) * | 1983-12-31 | 1985-07-11 | Bayer Ag, 5090 Leverkusen | Neue lackloesungen auf der basis von hydantoingruppen enthaltenden polymeren |
| NZ230314A (en) * | 1988-09-09 | 1991-02-26 | Ici Plc | Polyisocyanate composition obtained from the reaction product of uretonimine and/or carbodiimide-modified polyisocyanate with a carboxylic acid |
| US4966948A (en) * | 1988-10-14 | 1990-10-30 | Akzo Coatings, Inc. | Carbodiimide and metal containing emulsion or dispersion coating composition |
| JPH0362814A (ja) * | 1989-07-29 | 1991-03-18 | Nisshinbo Ind Inc | 親水性ポリカルボジイミドポリマー、該親水性ポリカルボジイミドポリマーによるパルプ状物及びそれらの製造方法 |
| US5115072A (en) * | 1990-09-05 | 1992-05-19 | Reichhold Chemicals, Inc. | Reactive resins with terminal and/or pendant vinyl groups |
| JPH059252A (ja) * | 1991-07-03 | 1993-01-19 | Nisshinbo Ind Inc | ポリカルボジイミドパルプ及びその製造方法 |
-
1986
- 1986-03-21 DE DE19863643239 patent/DE3643239C2/de not_active Expired - Lifetime
- 1986-03-21 DE DE3643238A patent/DE3643238C2/de not_active Expired
- 1986-03-21 DE DE19863609687 patent/DE3609687A1/de active Granted
- 1986-03-21 DE DE3643241A patent/DE3643241C2/de not_active Expired - Lifetime
- 1986-03-25 KR KR1019860002223A patent/KR900008986B1/ko not_active Expired
- 1986-03-26 FR FR868604382A patent/FR2579600B1/fr not_active Expired - Fee Related
- 1986-03-27 GB GB8607840A patent/GB2177710B/en not_active Expired
- 1986-03-27 CA CA000505286A patent/CA1269481A/en not_active Expired - Lifetime
-
1988
- 1988-03-30 GB GB8807544A patent/GB2201422B/en not_active Expired
- 1988-03-30 GB GB8807543A patent/GB2201421B/en not_active Expired
- 1988-07-26 US US07/225,598 patent/US5079326A/en not_active Expired - Fee Related
-
1991
- 1991-08-30 US US07/753,393 patent/US5321101A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2579600A1 (fr) | 1986-10-03 |
| US5079326A (en) | 1992-01-07 |
| GB2177710A (en) | 1987-01-28 |
| GB2177710B (en) | 1989-04-26 |
| DE3643239A1 (en, 2012) | 1986-10-02 |
| FR2579600B1 (fr) | 1993-01-22 |
| DE3643239C2 (en, 2012) | 1990-12-20 |
| DE3643241C2 (en, 2012) | 1990-07-26 |
| GB2201421B (en) | 1989-06-28 |
| GB2201422B (en) | 1989-06-28 |
| GB8607840D0 (en) | 1986-04-30 |
| US5321101A (en) | 1994-06-14 |
| GB8807543D0 (en) | 1988-05-05 |
| DE3609687A1 (de) | 1986-10-02 |
| KR860007303A (ko) | 1986-10-10 |
| CA1269481C (en) | 1990-05-22 |
| GB2201421A (en) | 1988-09-01 |
| GB8807544D0 (en) | 1988-05-05 |
| DE3643238C2 (en, 2012) | 1989-08-03 |
| KR900008986B1 (ko) | 1990-12-17 |
| GB2201422A (en) | 1988-09-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |