CA2280516A1 - Molecular weight controlled polymers by photopolymerization - Google Patents
Molecular weight controlled polymers by photopolymerization Download PDFInfo
- Publication number
- CA2280516A1 CA2280516A1 CA002280516A CA2280516A CA2280516A1 CA 2280516 A1 CA2280516 A1 CA 2280516A1 CA 002280516 A CA002280516 A CA 002280516A CA 2280516 A CA2280516 A CA 2280516A CA 2280516 A1 CA2280516 A1 CA 2280516A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- alkyl
- chain transfer
- transfer agent
- methyl
- 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.)
- Abandoned
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 38
- 239000000178 monomer Substances 0.000 claims abstract description 54
- 229910052799 carbon Inorganic materials 0.000 claims description 75
- 125000000217 alkyl group Chemical group 0.000 claims description 67
- 238000000034 method Methods 0.000 claims description 49
- 239000012986 chain transfer agent Substances 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 238000006062 fragmentation reaction Methods 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Chemical group 0.000 claims description 8
- 238000013467 fragmentation Methods 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000003999 initiator Substances 0.000 claims description 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 230000005855 radiation Effects 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 238000007342 radical addition reaction Methods 0.000 claims description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 2
- 229920001400 block copolymer Polymers 0.000 claims description 2
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 2
- 239000012634 fragment Substances 0.000 claims description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 230000006872 improvement Effects 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 238000010557 suspension polymerization reaction Methods 0.000 claims description 2
- 125000000520 N-substituted aminocarbonyl group Chemical group [*]NC(=O)* 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 abstract description 14
- 239000003795 chemical substances by application Substances 0.000 abstract description 13
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract description 10
- 238000010526 radical polymerization reaction Methods 0.000 abstract description 9
- 230000015572 biosynthetic process Effects 0.000 abstract description 6
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 229920006243 acrylic copolymer Polymers 0.000 abstract description 2
- 239000008199 coating composition Substances 0.000 abstract description 2
- 239000000976 ink Substances 0.000 abstract description 2
- 229920000058 polyacrylate Polymers 0.000 abstract description 2
- 238000007639 printing Methods 0.000 abstract description 2
- -1 SR' Inorganic materials 0.000 description 104
- 239000000203 mixture Substances 0.000 description 44
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 42
- 230000008569 process Effects 0.000 description 33
- 238000006116 polymerization reaction Methods 0.000 description 29
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 22
- 229940043232 butyl acetate Drugs 0.000 description 21
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 21
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 20
- 125000003545 alkoxy group Chemical group 0.000 description 19
- 235000019439 ethyl acetate Nutrition 0.000 description 19
- 230000004927 fusion Effects 0.000 description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
- 150000003254 radicals Chemical class 0.000 description 16
- 238000004458 analytical method Methods 0.000 description 13
- 239000011261 inert gas Substances 0.000 description 13
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 12
- 125000002947 alkylene group Chemical group 0.000 description 11
- 238000004817 gas chromatography Methods 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 10
- 239000012957 2-hydroxy-2-methyl-1-phenylpropanone Substances 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- PUZSUVGRVHEUQO-UHFFFAOYSA-N gentisyl alcohol Chemical compound OCC1=CC(O)=CC=C1O PUZSUVGRVHEUQO-UHFFFAOYSA-N 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 9
- 239000012948 isocyanate Substances 0.000 description 9
- 150000002513 isocyanates Chemical class 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 229910052727 yttrium Inorganic materials 0.000 description 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 5
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- RMMIEQKTIFFHRR-UHFFFAOYSA-N bis(1-hydroxy-2-phenylcyclohexyl)methanone Chemical compound C1CCCC(C=2C=CC=CC=2)C1(O)C(=O)C1(O)CCCCC1C1=CC=CC=C1 RMMIEQKTIFFHRR-UHFFFAOYSA-N 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 5
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000004437 phosphorous atom Chemical group 0.000 description 5
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 5
- 229940080818 propionamide Drugs 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- LFOXEOLGJPJZAA-UHFFFAOYSA-N [(2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl)phosphoryl]-(2,6-dimethoxyphenyl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)P(=O)(CC(C)CC(C)(C)C)C(=O)C1=C(OC)C=CC=C1OC LFOXEOLGJPJZAA-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 229940093499 ethyl acetate Drugs 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 230000001276 controlling effect Effects 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 239000012966 redox initiator Substances 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- JHYHYSDFWREWFU-UHFFFAOYSA-N 2,4-dihydroxy-1,5-bis[4-(2-hydroxyethyl)phenyl]-2,4-dimethylpentan-3-one Chemical compound C=1C=C(CCO)C=CC=1CC(C)(O)C(=O)C(O)(C)CC1=CC=C(CCO)C=C1 JHYHYSDFWREWFU-UHFFFAOYSA-N 0.000 description 2
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- QHVBLSNVXDSMEB-UHFFFAOYSA-N 2-(diethylamino)ethyl prop-2-enoate Chemical compound CCN(CC)CCOC(=O)C=C QHVBLSNVXDSMEB-UHFFFAOYSA-N 0.000 description 2
- MZGMQAMKOBOIDR-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCO MZGMQAMKOBOIDR-UHFFFAOYSA-N 0.000 description 2
- VETIYACESIPJSO-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound OCCOCCOCCOC(=O)C=C VETIYACESIPJSO-UHFFFAOYSA-N 0.000 description 2
- XUDBVJCTLZTSDC-UHFFFAOYSA-N 2-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=C XUDBVJCTLZTSDC-UHFFFAOYSA-N 0.000 description 2
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 2
- IEVADDDOVGMCSI-UHFFFAOYSA-N 2-hydroxybutyl 2-methylprop-2-enoate Chemical compound CCC(O)COC(=O)C(C)=C IEVADDDOVGMCSI-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- BQQGVSONEPNPAB-UHFFFAOYSA-N 3-(diethoxymethylsilyl)propyl 2-methylprop-2-enoate Chemical compound CCOC(OCC)[SiH2]CCCOC(=O)C(C)=C BQQGVSONEPNPAB-UHFFFAOYSA-N 0.000 description 2
- VLZDYNDUVLBNLD-UHFFFAOYSA-N 3-(dimethoxymethylsilyl)propyl 2-methylprop-2-enoate Chemical compound COC(OC)[SiH2]CCCOC(=O)C(C)=C VLZDYNDUVLBNLD-UHFFFAOYSA-N 0.000 description 2
- WHLXWNNASHWYEM-UHFFFAOYSA-N 3-[di(propan-2-yloxy)methylsilyl]propyl 2-methylprop-2-enoate Chemical compound CC(C)OC(OC(C)C)[SiH2]CCCOC(=O)C(C)=C WHLXWNNASHWYEM-UHFFFAOYSA-N 0.000 description 2
- RSSKWJGDNCKSCC-UHFFFAOYSA-N 3-di(propan-2-yloxy)silylpropyl 2-methylprop-2-enoate Chemical compound CC(C)O[SiH](OC(C)C)CCCOC(=O)C(C)=C RSSKWJGDNCKSCC-UHFFFAOYSA-N 0.000 description 2
- KIUQKRVLTQTVDR-UHFFFAOYSA-N 3-di(propan-2-yloxy)silylpropyl prop-2-enoate Chemical compound CC(C)O[SiH](OC(C)C)CCCOC(=O)C=C KIUQKRVLTQTVDR-UHFFFAOYSA-N 0.000 description 2
- SLDXSSRFNABVCN-UHFFFAOYSA-N 3-diethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[SiH](OCC)CCCOC(=O)C(C)=C SLDXSSRFNABVCN-UHFFFAOYSA-N 0.000 description 2
- HNVMCAHOYIOFAQ-UHFFFAOYSA-N 3-dimethoxysilylpropyl prop-2-enoate Chemical compound CO[SiH](OC)CCCOC(=O)C=C HNVMCAHOYIOFAQ-UHFFFAOYSA-N 0.000 description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 2
- YFISHOAHNLGUEL-UHFFFAOYSA-N 3-tributoxysilylpropyl prop-2-enoate Chemical compound CCCCO[Si](OCCCC)(OCCCC)CCCOC(=O)C=C YFISHOAHNLGUEL-UHFFFAOYSA-N 0.000 description 2
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 description 2
- XDQWJFXZTAWJST-UHFFFAOYSA-N 3-triethoxysilylpropyl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C=C XDQWJFXZTAWJST-UHFFFAOYSA-N 0.000 description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-N 4-ethenylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-N 0.000 description 2
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 2
- FKAJZOZTZXQGTJ-UHFFFAOYSA-N 5,5-dimethyl-1,3-diazabicyclo[2.2.0]hex-3-ene Chemical compound C1N2C(C1(C)C)=NC2 FKAJZOZTZXQGTJ-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Chemical group 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 2
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- 239000000539 dimer Substances 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- WCMINAGIRMRVHT-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate;methyl 2-methylprop-2-enoate Chemical compound COC(=O)C(C)=C.CCOC(=O)C(C)=C WCMINAGIRMRVHT-UHFFFAOYSA-N 0.000 description 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 125000002960 margaryl 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])[H] 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920006030 multiblock copolymer Polymers 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- WTNTZFRNCHEDOS-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-methylpropanamide Chemical compound CC(C)C(=O)NCCO WTNTZFRNCHEDOS-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- BUGISVZCMXHOHO-UHFFFAOYSA-N n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-2-[[1-[[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCC(CO)(CO)NC(=O)C(C)(C)N=NC(C)(C)C(=O)NC(CO)(CO)CO BUGISVZCMXHOHO-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- QQZXAODFGRZKJT-UHFFFAOYSA-N n-tert-butyl-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NC(C)(C)C QQZXAODFGRZKJT-UHFFFAOYSA-N 0.000 description 1
- XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 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
- 239000000123 paper Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- GWLJTAJEHRYMCA-UHFFFAOYSA-N phospholane Chemical group C1CCPC1 GWLJTAJEHRYMCA-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- NJSJBTVAKUBCKG-UHFFFAOYSA-N propylazanide Chemical compound CCC[NH-] NJSJBTVAKUBCKG-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 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
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920006250 telechelic polymer Polymers 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000004383 yellowing Methods 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
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
- Paints Or Removers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3822597P | 1997-02-19 | 1997-02-19 | |
| US60/038,225 | 1997-02-19 | ||
| PCT/US1998/003133 WO1998037104A1 (en) | 1997-02-19 | 1998-02-18 | Molecular weight controlled polymers by photopolymerization |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2280516A1 true CA2280516A1 (en) | 1998-08-27 |
Family
ID=21898732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002280516A Abandoned CA2280516A1 (en) | 1997-02-19 | 1998-02-18 | Molecular weight controlled polymers by photopolymerization |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6316519B1 (enExample) |
| EP (1) | EP0961786B1 (enExample) |
| JP (1) | JP2001512519A (enExample) |
| KR (1) | KR100487041B1 (enExample) |
| CN (1) | CN1121420C (enExample) |
| BR (1) | BR9807683A (enExample) |
| CA (1) | CA2280516A1 (enExample) |
| DE (1) | DE69806229T2 (enExample) |
| WO (1) | WO1998037104A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6716905B1 (en) | 1998-12-23 | 2004-04-06 | Coatings Ag | Coating agent |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4632332B2 (ja) | 1998-12-18 | 2011-02-16 | ビーエーエスエフ コーティングス ゲゼルシャフト ミット ベシュレンクテル ハフツング | 高分子量反応生成物の製造方法 |
| DE19930066A1 (de) | 1999-06-30 | 2001-01-11 | Basf Coatings Ag | Farb- und/oder effektgebende Mehrschichtlackierung, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19930665A1 (de) | 1999-07-02 | 2001-01-11 | Basf Coatings Ag | Basislack und seine Verwendung zur Herstellung von farb- und/oder effektgebenden Basislackierungen und Mehrschichtlackierung |
| DE19930664A1 (de) | 1999-07-02 | 2001-01-11 | Basf Coatings Ag | Klarlack und seine Verwendung zur Herstellung von Klarlackierungen und farb- und/oder effektgebenden Mehrschichtlackierungen |
| DE19959923A1 (de) | 1999-12-11 | 2001-06-28 | Basf Coatings Ag | Wäßrige Primärdispersionen und Beschichtungsstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19961063A1 (de) | 1999-12-17 | 2001-07-12 | Basf Ag | Verfahren zur Herstellung eines polymeren Umsetzungsprodukts |
| DE10005819A1 (de) | 2000-02-10 | 2001-08-23 | Basf Coatings Ag | Wäßrige Primärdispersionen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10018078A1 (de) | 2000-04-12 | 2001-11-08 | Basf Coatings Ag | Formmassen und Verfahren zur Herstellung von Formkörpern |
| DE10018601A1 (de) | 2000-04-14 | 2001-10-25 | Basf Coatings Ag | Wäßrige Primärdispersionen und Beschichtungsstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10029802A1 (de) | 2000-06-16 | 2002-01-03 | Basf Coatings Ag | Farb- und/oder effektgebende wäßrige Beschichtungsstoffe und ihre Verwendung zur Herstellung farb- und/oder effektgebender, verformbarer Laminate |
| DE10029695A1 (de) * | 2000-06-16 | 2001-12-20 | Basf Ag | Verfahren zur Herstellung eines polymeren Umsetzungsprodukts |
| DE10106567A1 (de) | 2001-02-13 | 2002-08-22 | Basf Coatings Ag | Von flüchtigen organischen Stoffen im wesentlichen oder völlig freie wäßrige Primärdispersion, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE10106566A1 (de) | 2001-02-13 | 2002-08-22 | Basf Coatings Ag | Von flüchtigen organischen Stoffen im wesentlichen oder völlig freier wäßriger Beschichtungsstoff, Verfahren zu seiner Herstellung und seine Verwendung |
| EP1390664A4 (en) | 2001-03-30 | 2008-01-02 | Univ Arizona | MATERIALS, METHODS AND USES FOR PHOTOCHEMICAL GENERATION OF ACIDS AND / OR RADICAL SPECIES |
| US7541392B2 (en) * | 2004-09-14 | 2009-06-02 | E.I. Du Pont De Nemours And Company | Materials leading to improved dental composites and dental composites made therefrom |
| US20060058418A1 (en) * | 2004-09-14 | 2006-03-16 | Brandenburg Charles J | Materials leading to improved dental composites and dental composites made therefrom |
| US20060058416A1 (en) * | 2004-09-14 | 2006-03-16 | Brandenburg Charles J | Materials leading to improved dental composites and dental composites made therefrom |
| TW200628495A (en) * | 2004-10-19 | 2006-08-16 | Johnson & Johnson Vision Care | Process for the synthesis of soluble, high molecular weight polymers |
| US7402624B2 (en) * | 2004-11-08 | 2008-07-22 | E.I. Du Pont De Nemours & Company | Graft copolymers with segmented arms and their preparation and use |
| AT502110B1 (de) * | 2005-06-30 | 2008-09-15 | Univ Wien Tech | Mit strahlung härtbare, in organischen lösungsmitteln lösliche zusammensetzung und deren verwendung für rapid prototyping verfahren |
| ES2288386B2 (es) * | 2005-12-19 | 2008-09-16 | Universidad De Alicante | Material de registro holografico medioambientalmente compatible basado en acrilatos metalicos. |
| CN103370041B (zh) * | 2011-02-15 | 2016-06-15 | 3M创新有限公司 | 包含烯键式不饱和加成-断裂剂的牙科用组合物 |
| US20120208965A1 (en) | 2011-02-15 | 2012-08-16 | 3M Innovative Properties Company | Addition-fragmentation agents |
| US10370322B2 (en) * | 2011-02-15 | 2019-08-06 | 3M Innovative Properties Company | Addition-fragmentation agents |
| WO2013003396A2 (en) * | 2011-06-29 | 2013-01-03 | 3M Innovative Properties Company | Dental compositions comprising a fatty mono(meth)acrylate |
| WO2013028397A2 (en) * | 2011-08-23 | 2013-02-28 | 3M Innovative Properties Company | Dental compositions comprising addition-fragmentation agents |
| JP6351608B2 (ja) | 2012-11-12 | 2018-07-04 | スリーエム イノベイティブ プロパティズ カンパニー | 付加開裂剤を含む歯科用組成物 |
| JP6360708B2 (ja) * | 2014-04-22 | 2018-07-18 | ニッタ株式会社 | 感温性粘着剤 |
| JP6376824B2 (ja) * | 2014-04-24 | 2018-08-22 | ニッタ株式会社 | 感温性粘着剤の製造方法 |
| EP2965741A1 (de) | 2014-07-11 | 2016-01-13 | Ivoclar Vivadent AG | Komposite mit gesteuerter Netzwerkstruktur |
| JP7587212B2 (ja) | 2020-04-17 | 2024-11-20 | Ｋｊケミカルズ株式会社 | スルフィド基を有するアリル位置換メタクリル酸エステルの製造方法 |
| EP3932383B1 (de) | 2020-07-03 | 2022-08-24 | Ivoclar Vivadent AG | Komposite mit verringerter polymerisationsschrumpfungsspannung |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB861438A (en) * | 1956-11-24 | 1961-02-22 | Dunlop Rubber Co | Polymerisation of organic compounds |
| AU4691679A (en) * | 1973-12-13 | 1979-10-11 | Unisearch Limited | Preparation and use of prepolymers in radiation curable compositions |
| JPS60258275A (ja) * | 1984-06-04 | 1985-12-20 | Hitachi Chem Co Ltd | 放射線硬化型感圧性接着剤組成物 |
| US5385996A (en) * | 1986-12-05 | 1995-01-31 | Commonwealth Scientific And Industrial Research Organisation | Control of molecular weight and end-group functionality of polymers |
| JPH01167305A (ja) * | 1987-12-23 | 1989-07-03 | Kao Corp | 低分子量水溶性重合体の製造方法 |
| US5932675A (en) * | 1989-06-05 | 1999-08-03 | Commonwealth Scientific And Industrial Research Organisation | Free-radical chain transfer polymerization process |
| JPH06102689B2 (ja) * | 1989-08-29 | 1994-12-14 | 積水化学工業株式会社 | 光重合性組成物および粘着剤の製造法 |
| IL111484A (en) * | 1993-11-03 | 2001-06-14 | Commw Scient Ind Res Org | Polymerization process using pendant chain transfer means to regulate the molecular weight, the polymers thus obtained and a number of new pesticide compounds |
| US5391406A (en) * | 1994-03-25 | 1995-02-21 | National Starch And Chemical Investment Holding Corporation | Process of preparing hot melt pressure sensitive adhesives on a substrate |
| JP3651905B2 (ja) * | 1996-02-23 | 2005-05-25 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 分枝ポリマー合成 |
-
1998
- 1998-01-20 US US09/367,906 patent/US6316519B1/en not_active Expired - Fee Related
- 1998-02-18 DE DE69806229T patent/DE69806229T2/de not_active Expired - Fee Related
- 1998-02-18 WO PCT/US1998/003133 patent/WO1998037104A1/en not_active Ceased
- 1998-02-18 CN CN98802672A patent/CN1121420C/zh not_active Expired - Fee Related
- 1998-02-18 CA CA002280516A patent/CA2280516A1/en not_active Abandoned
- 1998-02-18 JP JP53683498A patent/JP2001512519A/ja not_active Ceased
- 1998-02-18 BR BR9807683A patent/BR9807683A/pt not_active Application Discontinuation
- 1998-02-18 EP EP98906540A patent/EP0961786B1/en not_active Expired - Lifetime
- 1998-02-18 KR KR10-1999-7007464A patent/KR100487041B1/ko not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6716905B1 (en) | 1998-12-23 | 2004-04-06 | Coatings Ag | Coating agent |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1998037104A1 (en) | 1998-08-27 |
| DE69806229D1 (de) | 2002-08-01 |
| EP0961786A1 (en) | 1999-12-08 |
| KR100487041B1 (ko) | 2005-05-03 |
| US6316519B1 (en) | 2001-11-13 |
| JP2001512519A (ja) | 2001-08-21 |
| KR20000071174A (ko) | 2000-11-25 |
| CN1248266A (zh) | 2000-03-22 |
| DE69806229T2 (de) | 2003-02-20 |
| BR9807683A (pt) | 2000-03-21 |
| CN1121420C (zh) | 2003-09-17 |
| EP0961786B1 (en) | 2002-06-26 |
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