CN1084754C - 制备氨基甲酸官能聚合物的方法 - Google Patents
制备氨基甲酸官能聚合物的方法 Download PDFInfo
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- CN1084754C CN1084754C CN95121720A CN95121720A CN1084754C CN 1084754 C CN1084754 C CN 1084754C CN 95121720 A CN95121720 A CN 95121720A CN 95121720 A CN95121720 A CN 95121720A CN 1084754 C CN1084754 C CN 1084754C
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- Prior art keywords
- acid
- carbamate
- alkyl
- ester
- carbon atom
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 35
- 229920001002 functional polymer Polymers 0.000 title description 10
- -1 carbamate compound Chemical class 0.000 claims abstract description 42
- 239000000178 monomer Substances 0.000 claims abstract description 30
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 13
- 239000003999 initiator Substances 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- 238000012644 addition polymerization Methods 0.000 claims description 5
- 230000008859 change Effects 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
- 125000002524 organometallic group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical group [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 claims 1
- 230000032050 esterification Effects 0.000 abstract description 2
- 238000005886 esterification reaction Methods 0.000 abstract description 2
- 150000003254 radicals Chemical class 0.000 abstract description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000002904 solvent Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000008199 coating composition Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 238000005809 transesterification reaction Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- 150000005676 cyclic carbonates Chemical class 0.000 description 5
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
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- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 229920003180 amino resin Polymers 0.000 description 4
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- 229920001807 Urea-formaldehyde Polymers 0.000 description 3
- 238000007171 acid catalysis Methods 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 3
- 239000003849 aromatic solvent Substances 0.000 description 3
- 229920005601 base polymer Polymers 0.000 description 3
- 235000013877 carbamide Nutrition 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 238000007711 solidification Methods 0.000 description 3
- 230000008023 solidification Effects 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical group SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- JRLPEMVDPFPYPJ-UHFFFAOYSA-N 1-ethyl-4-methylbenzene Chemical compound CCC1=CC=C(C)C=C1 JRLPEMVDPFPYPJ-UHFFFAOYSA-N 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
- JJRDRFZYKKFYMO-UHFFFAOYSA-N 2-methyl-2-(2-methylbutan-2-ylperoxy)butane Chemical compound CCC(C)(C)OOC(C)(C)CC JJRDRFZYKKFYMO-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N acrylaldehyde Natural products C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000008064 anhydrides Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 230000003750 conditioning effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
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- 238000009998 heat setting Methods 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- ZLCSFXXPPANWQY-UHFFFAOYSA-N meta-methylethylbenzene Natural products CCC1=CC=CC(C)=C1 ZLCSFXXPPANWQY-UHFFFAOYSA-N 0.000 description 2
- VLCAYQIMSMPEBW-UHFFFAOYSA-N methyl 3-hydroxy-2-methylidenebutanoate Chemical compound COC(=O)C(=C)C(C)O VLCAYQIMSMPEBW-UHFFFAOYSA-N 0.000 description 2
- HYFLWBNQFMXCPA-UHFFFAOYSA-N o-toluene acid methyl ester Natural products CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
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- 239000002987 primer (paints) Substances 0.000 description 2
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- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
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- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- ZCYXFITUYVYSJW-UHFFFAOYSA-N 1-ethenylisoquinoline Chemical compound C1=CC=C2C(C=C)=NC=CC2=C1 ZCYXFITUYVYSJW-UHFFFAOYSA-N 0.000 description 1
- ZMARGGQEAJXRFP-UHFFFAOYSA-N 1-hydroxypropan-2-yl 2-methylprop-2-enoate Chemical compound OCC(C)OC(=O)C(C)=C ZMARGGQEAJXRFP-UHFFFAOYSA-N 0.000 description 1
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- YZBOVSFWWNVKRJ-UHFFFAOYSA-M 2-butoxycarbonylbenzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1C([O-])=O YZBOVSFWWNVKRJ-UHFFFAOYSA-M 0.000 description 1
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- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- JAVOYFHBJFLMRQ-UHFFFAOYSA-N 3-methylbutyl but-2-enoate Chemical compound CC=CC(=O)OCCC(C)C JAVOYFHBJFLMRQ-UHFFFAOYSA-N 0.000 description 1
- COCLLEMEIJQBAG-UHFFFAOYSA-N 8-methylnonyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C(C)=C COCLLEMEIJQBAG-UHFFFAOYSA-N 0.000 description 1
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- 238000001321 HNCO Methods 0.000 description 1
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- 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
- 238000010521 absorption reaction Methods 0.000 description 1
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- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
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- 238000009835 boiling Methods 0.000 description 1
- PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
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- IALFAHZQTSACNB-UHFFFAOYSA-N carbamic acid 3-hydroxypropyl prop-2-enoate Chemical compound C(C=C)(=O)OCCCO.C(N)(O)=O IALFAHZQTSACNB-UHFFFAOYSA-N 0.000 description 1
- VSKFADHADUWCCL-UHFFFAOYSA-N carbamoperoxoic acid Chemical compound NC(=O)OO VSKFADHADUWCCL-UHFFFAOYSA-N 0.000 description 1
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- 238000007766 curtain coating Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical group CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- UHKJHMOIRYZSTH-UHFFFAOYSA-N ethyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OCC UHKJHMOIRYZSTH-UHFFFAOYSA-N 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 244000144992 flock Species 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229940119545 isobornyl methacrylate Drugs 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical compound C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical group CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- 229940065472 octyl acrylate Drugs 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- PWYYERNADDIMJR-UHFFFAOYSA-N pentyl but-2-enoate Chemical compound CCCCCOC(=O)C=CC PWYYERNADDIMJR-UHFFFAOYSA-N 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- MPNNOLHYOHFJKL-UHFFFAOYSA-N peroxyphosphoric acid Chemical compound OOP(O)(O)=O MPNNOLHYOHFJKL-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
- 230000036314 physical performance Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 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
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007634 remodeling Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Substances C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US365,648 | 1994-12-29 | ||
| US08/365,648 US5552497A (en) | 1994-12-29 | 1994-12-29 | Method of preparing carbamate-functional polymer |
| US365648 | 1994-12-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1132757A CN1132757A (zh) | 1996-10-09 |
| CN1084754C true CN1084754C (zh) | 2002-05-15 |
Family
ID=23439743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN95121720A Expired - Fee Related CN1084754C (zh) | 1994-12-29 | 1995-12-28 | 制备氨基甲酸官能聚合物的方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5552497A (enExample) |
| EP (1) | EP0719795B1 (enExample) |
| JP (1) | JP3919841B2 (enExample) |
| KR (1) | KR100348369B1 (enExample) |
| CN (1) | CN1084754C (enExample) |
| AT (1) | ATE169642T1 (enExample) |
| AU (1) | AU691373B2 (enExample) |
| BR (1) | BR9506118A (enExample) |
| CA (1) | CA2166241C (enExample) |
| DE (1) | DE69504025T2 (enExample) |
| DK (1) | DK0719795T3 (enExample) |
| ES (1) | ES2122428T3 (enExample) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2101353T3 (es) * | 1992-10-30 | 1997-07-01 | Ppg Industries Inc | Composiciones filmogenas endurecibles con aminoplastico que producen peliculas resistentes al ataque del acido. |
| US6165618A (en) * | 1994-11-03 | 2000-12-26 | Basf Corporation | Curable coating compositions containing carbamate resin and additives |
| US5852136A (en) * | 1996-07-01 | 1998-12-22 | Basf Corporation | Curable coating composition |
| US5777048A (en) * | 1996-06-20 | 1998-07-07 | Basf Corporation | Method for modified aminoplast compounds, aminoplasts obtained thereby and coatings containing the same |
| US5709950A (en) * | 1994-04-29 | 1998-01-20 | Ppg Industries, Inc. | Color-plus-clear composite coatings that contain polymers having carbamate functionality |
| US5976701A (en) * | 1994-04-29 | 1999-11-02 | Ppg Industries Ohio, Inc. | Flexible aminoplast-curable film-forming compositions and composite coating |
| MX191670B (es) * | 1994-04-29 | 1999-04-07 | Ppg Ind Ohio Inc | Composiciones de formacion de pelicula endurecible de aminoplasto flexible que proporcionan peliculas que tienen resistencia a ataque con acido. |
| US6117931A (en) * | 1996-07-01 | 2000-09-12 | Basf Corporation | Curable coating compositions having improved effect pigment orientation and a method of using the same |
| US5976615A (en) * | 1997-07-09 | 1999-11-02 | Basf Corporation | Carbamate curable coating composition and method for improved adhesion |
| US5907024A (en) * | 1997-11-12 | 1999-05-25 | Basf Corporation | High solids thermosetting compositions with dual cure mechanism |
| US5945499A (en) * | 1997-11-12 | 1999-08-31 | Basf Corporation | High solids thermosetting compositions with dual cure mechanism |
| US5985463A (en) * | 1998-06-24 | 1999-11-16 | E.I. Du Pont De Nemours And Company | Coating containing hydroxy containing acrylosilane polymer to improve mar and acid etch resistance |
| US6306965B1 (en) * | 1998-08-31 | 2001-10-23 | Ppg Industries Ohio, Inc. | Thermosetting compositions containing carbamate-functional polylmers prepared using atom transfer radical polymerization |
| US6187376B1 (en) * | 1998-10-01 | 2001-02-13 | Basf Corporation | Method for improving the adhesion of a repair coating to a previously coated substrate |
| US6075108A (en) * | 1998-10-06 | 2000-06-13 | Arco Chemical Technology, L.P. | Carbamate-functional allyl monomers and polymers therefrom |
| US6106951A (en) * | 1998-11-24 | 2000-08-22 | Basf Corporation | Curable coating compositions containing carmamate-functional compounds |
| US6048443A (en) * | 1998-12-21 | 2000-04-11 | Basf Corporation | Low bake cathodic electrocoat having dual cure mechanism |
| US6165338A (en) * | 1998-12-21 | 2000-12-26 | Basf Corporation | Cathodic electrocoat having a carbamate functional resin |
| US6214188B1 (en) | 1998-12-21 | 2001-04-10 | Basf Corporation | Anodic electrocoat having a carbamate functional resin |
| US6346591B1 (en) * | 1999-05-21 | 2002-02-12 | Basf Corporation | Monomer and polymerization process |
| US6331596B1 (en) * | 1999-06-28 | 2001-12-18 | Basf Corporation | Method of preparing carbamate-functional polymers |
| US6303690B1 (en) * | 1999-12-15 | 2001-10-16 | Basf Corporation | Cathodic electrocoat having a carbamate functional resin and a carbamate functional reactive additive |
| US6391968B1 (en) | 1999-12-15 | 2002-05-21 | Basf Corporation | Curable coating compositions containing carbamate functional polymers and carbamate functional reactive additives |
| US6380323B1 (en) | 1999-12-15 | 2002-04-30 | Basf Corporation | Electrocoat resin compositions containing carbamate functional resins having one or more quaternary ammonium groups and at least one carbamate functional reactive additive |
| US6362285B1 (en) | 1999-12-15 | 2002-03-26 | Basf Corporation | Curable coating compositions containing carbamate functional reactive additives |
| DE10004498A1 (de) * | 2000-02-02 | 2001-08-09 | Basf Coatings Ag | Diethyloctandioldicarbamate und Diethyloctandioldiallophanate, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US6881791B2 (en) * | 2000-06-16 | 2005-04-19 | Basf Corporation | Poly-electrolyte free block copolymers and their use in crosslinking coatings applications |
| US6699943B2 (en) | 2000-06-16 | 2004-03-02 | Basf Corporation | Water-based coating composition having carbamate-melamine cross-linking, method of preparing the same, and a cured film thereof |
| US6916877B2 (en) * | 2000-06-16 | 2005-07-12 | Basf Corporation | Coating composition including a water-based copolymer cross-linking with a water-dispersible cross-linking agent, method of preparing the same, and a cured film thereof |
| DE10041634C2 (de) * | 2000-08-24 | 2002-10-17 | Basf Coatings Ag | Wäßrige Dispersion und ihre Verwendung zur Herstellung von thermisch und mit aktinischer Strahlung härtbaren Beschichtungsstoffen, Klebstoffen und Dichtungsmassen |
| US6541577B2 (en) | 2000-12-06 | 2003-04-01 | Basf Corporation | Carbamate functional polymers and oligomers |
| US6858674B2 (en) | 2002-10-31 | 2005-02-22 | Basf Corporation | Carbamate functional materials, a method of making said materials, and curable coating compositions containing said materials |
| US20040030176A1 (en) * | 2001-09-05 | 2004-02-12 | Ohrbom Walter H. | Gamma hydroxy carbamate compounds and method of making and using the same |
| US6977309B2 (en) | 2002-10-31 | 2005-12-20 | Basf Corporation | Compounds having a secondary or tertiary hydroxy of halide group separated from a primary carbamate group by three or more carbon atoms and a method of making the same |
| US6900270B2 (en) | 2002-10-31 | 2005-05-31 | Basf Corporation | Curable coating compositions with carbamate compounds |
| US6890994B2 (en) * | 2002-10-31 | 2005-05-10 | Basf Corporation | Curable coating compositions with carbamate-containing acrylic polymers |
| US7867569B2 (en) | 2005-10-07 | 2011-01-11 | E. I. Du Pont De Nemours And Company | Method of forming multi-layer coating on automobile bodies without a primer bake |
| US7740912B2 (en) | 2005-10-07 | 2010-06-22 | E.I. Du Pont De Nemours And Company | Method of forming multi-layer coatings on automobile bodies without a primer bake |
| US7740911B2 (en) | 2005-10-07 | 2010-06-22 | E. I. Du Pont De Nemours And Company | Method of forming a multi-layer coating on automobile bodies without a primer bake |
| EP2089483B2 (en) | 2006-12-04 | 2015-11-25 | Coatings Foreign IP Co. LLC | Coating material containing a mixture of mineral silicates and diurea |
| US8668534B2 (en) | 2007-03-02 | 2014-03-11 | Liquid Robotics, Inc | Wave power |
| JP5933205B2 (ja) * | 2010-09-07 | 2016-06-08 | 関西ペイント株式会社 | 共重合体、該共重合体を含有する水性塗料組成物及び複層塗膜形成方法 |
| WO2012033079A1 (ja) * | 2010-09-07 | 2012-03-15 | 関西ペイント株式会社 | 共重合体、該共重合体を含有する水性塗料組成物及び複層塗膜形成方法 |
| AU2012228956B2 (en) * | 2011-03-17 | 2016-04-07 | Liquid Robotics Inc. | Autonomous wave-powered substance distribution vessels for fertilizing plankton, feeding fish, and sequestering carbon from the atmosphere |
| MY166904A (en) | 2011-03-17 | 2018-07-24 | Liquid Robotics Inc | Wave-powered devices configured for nesting |
| CA3077995C (en) | 2011-06-28 | 2022-07-19 | Liquid Robotics, Inc. | Watercraft that harvest both locomotive thrust and electrical power from wave motion |
| JP6584405B2 (ja) * | 2013-08-15 | 2019-10-02 | ダウ グローバル テクノロジーズ エルエルシー | ポリカルバメートを生成するためのプロセス、それによって生成されたポリカルバメート、及びポリカルバメートを含むコーティング組成物 |
| US20150210795A1 (en) * | 2014-01-30 | 2015-07-30 | Basf Coatings Gmbh | Amphiphilic carbamate-functional copolymers and coatings containing them |
| CN108473817B (zh) * | 2015-12-28 | 2020-10-20 | 株式会社Kcc | 耐刮擦性优异的单组分型涂料组合物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US430497A (en) * | 1890-06-17 | Vending apparatus | ||
| US4126747A (en) * | 1976-12-28 | 1978-11-21 | Union Carbide Corporation | Carbamoyloxy acrylate compounds |
| US4279833A (en) * | 1979-12-17 | 1981-07-21 | Ashland Chemical Company | Acrylic monomers containing carbamate functionality |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3479328A (en) * | 1966-11-18 | 1969-11-18 | Ashland Oil Inc | Novel monomers and polymers |
| US3674838A (en) * | 1969-06-05 | 1972-07-04 | Ashland Oil Inc | Vinyl carbamyloxy carboxylates |
| FR2459805A1 (fr) * | 1979-06-26 | 1981-01-16 | Rhone Poulenc Ind | Nouvelle composition polymerisable a base d'un monomere soluble dans l'eau renfermant au moins un ester ethylenique presentant une fonction alcool |
| US4340497A (en) * | 1980-03-21 | 1982-07-20 | Union Carbide Corporation | (N-Substituted carbamoyloxy) alkanoyloxyalkyl acrylate esters |
| CA1196009A (en) * | 1981-12-10 | 1985-10-29 | Albert C. Chen | Acryloyl and alkylacryloyl polyalkoxy carbamates, compositions thereof and their use in radiation curable coatings |
| US4520074A (en) * | 1984-07-20 | 1985-05-28 | General Electric Company | Polymerizable 3-aroyloxyphenyl carbamates and methods for their preparation and use |
| US4847329A (en) * | 1987-06-30 | 1989-07-11 | Union Carbide Corporation | (N-substituted carbamoyloxy)alkanoyloxyalkyl acrylate polymers and compositions made therefrom |
| DE3726956A1 (de) * | 1987-08-13 | 1989-02-23 | Alfred Krueger | Ueberzugsmittel |
| DE3811497C2 (de) * | 1987-08-13 | 1996-05-23 | Basf Lacke & Farben | Überzugsmittel |
| IT1223345B (it) * | 1987-11-04 | 1990-09-19 | Vedril Spa | Procedimento per la preparazione di polimeri acrilici immidizzati |
| DE3929697C2 (de) * | 1988-04-06 | 1997-10-16 | Basf Lacke & Farben | Lösungsmittelhaltiges bzw. wasserverdünnbares Überzugsmittel |
| EP0365098B1 (en) * | 1988-10-21 | 1993-12-08 | Akzo Nobel N.V. | Waterborne coatings and binder systems for use therein |
| DE3933890B4 (de) * | 1989-10-11 | 2006-05-11 | Basf Coatings Ag | Verfahren zur Herstellung von modifizierten Polyestern und deren Verwendung |
| ES2101353T3 (es) * | 1992-10-30 | 1997-07-01 | Ppg Industries Inc | Composiciones filmogenas endurecibles con aminoplastico que producen peliculas resistentes al ataque del acido. |
| TW242644B (enExample) * | 1992-10-30 | 1995-03-11 | Ppg Industries Inc | |
| US6103816A (en) * | 1992-10-30 | 2000-08-15 | Ppg Industries Ohio, Inc. | Aqueous aminoplast curable film-forming compositions providing films having resistance to acid etching |
-
1994
- 1994-12-29 US US08/365,648 patent/US5552497A/en not_active Expired - Lifetime
-
1995
- 1995-12-14 EP EP95119690A patent/EP0719795B1/en not_active Expired - Lifetime
- 1995-12-14 DK DK95119690T patent/DK0719795T3/da active
- 1995-12-14 DE DE69504025T patent/DE69504025T2/de not_active Expired - Lifetime
- 1995-12-14 AT AT95119690T patent/ATE169642T1/de not_active IP Right Cessation
- 1995-12-14 ES ES95119690T patent/ES2122428T3/es not_active Expired - Lifetime
- 1995-12-20 KR KR1019950053035A patent/KR100348369B1/ko not_active Expired - Lifetime
- 1995-12-28 BR BR9506118A patent/BR9506118A/pt not_active IP Right Cessation
- 1995-12-28 CA CA002166241A patent/CA2166241C/en not_active Expired - Lifetime
- 1995-12-28 JP JP34350295A patent/JP3919841B2/ja not_active Expired - Lifetime
- 1995-12-28 CN CN95121720A patent/CN1084754C/zh not_active Expired - Fee Related
- 1995-12-29 AU AU40757/95A patent/AU691373B2/en not_active Ceased
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US430497A (en) * | 1890-06-17 | Vending apparatus | ||
| US4126747A (en) * | 1976-12-28 | 1978-11-21 | Union Carbide Corporation | Carbamoyloxy acrylate compounds |
| US4279833A (en) * | 1979-12-17 | 1981-07-21 | Ashland Chemical Company | Acrylic monomers containing carbamate functionality |
Also Published As
| Publication number | Publication date |
|---|---|
| AU691373B2 (en) | 1998-05-14 |
| DE69504025T2 (de) | 1999-04-22 |
| CN1132757A (zh) | 1996-10-09 |
| US5552497A (en) | 1996-09-03 |
| JP3919841B2 (ja) | 2007-05-30 |
| BR9506118A (pt) | 1997-12-23 |
| EP0719795A2 (en) | 1996-07-03 |
| ATE169642T1 (de) | 1998-08-15 |
| DE69504025D1 (de) | 1998-09-17 |
| EP0719795A3 (enExample) | 1996-08-07 |
| KR100348369B1 (ko) | 2003-02-07 |
| CA2166241C (en) | 2005-06-07 |
| KR960022594A (ko) | 1996-07-18 |
| DK0719795T3 (da) | 1999-05-17 |
| CA2166241A1 (en) | 1996-06-30 |
| ES2122428T3 (es) | 1998-12-16 |
| AU4075795A (en) | 1996-07-04 |
| JPH08231642A (ja) | 1996-09-10 |
| EP0719795B1 (en) | 1998-08-12 |
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