SE412396C - Fotopolymeriserbar komposition - Google Patents
Fotopolymeriserbar kompositionInfo
- Publication number
- SE412396C SE412396C SE7213392A SE1339272A SE412396C SE 412396 C SE412396 C SE 412396C SE 7213392 A SE7213392 A SE 7213392A SE 1339272 A SE1339272 A SE 1339272A SE 412396 C SE412396 C SE 412396C
- Authority
- SE
- Sweden
- Prior art keywords
- photosensitizer
- parts
- reducing agent
- groups
- composition
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 88
- 239000003638 chemical reducing agent Substances 0.000 claims description 53
- 239000003504 photosensitizing agent Substances 0.000 claims description 48
- 239000000463 material Substances 0.000 claims description 35
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
- -1 aromatic vinyl compound Chemical class 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 239000003973 paint Substances 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 6
- 239000000049 pigment Substances 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims description 4
- 230000005281 excited state Effects 0.000 claims description 4
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 claims description 3
- 229930006711 bornane-2,3-dione Natural products 0.000 claims description 3
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 3
- HNPDNOZNULJJDL-UHFFFAOYSA-N ethyl n-ethenylcarbamate Chemical compound CCOC(=O)NC=C HNPDNOZNULJJDL-UHFFFAOYSA-N 0.000 claims description 3
- DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 claims description 3
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 3
- SXPUVBFQXJHYNS-UHFFFAOYSA-N α-furil Chemical compound C=1C=COC=1C(=O)C(=O)C1=CC=CO1 SXPUVBFQXJHYNS-UHFFFAOYSA-N 0.000 claims description 3
- FXJVNINSOKCNJP-UHFFFAOYSA-M 4-methylbenzenesulfinate Chemical compound CC1=CC=C(S([O-])=O)C=C1 FXJVNINSOKCNJP-UHFFFAOYSA-M 0.000 claims description 2
- AFPRJLBZLPBTPZ-UHFFFAOYSA-N acenaphthoquinone Chemical compound C1=CC(C(C2=O)=O)=C3C2=CC=CC3=C1 AFPRJLBZLPBTPZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- ACLZYRNSDLQOIA-UHFFFAOYSA-N o-tolylthiourea Chemical compound CC1=CC=CC=C1NC(N)=S ACLZYRNSDLQOIA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 45
- 238000000034 method Methods 0.000 description 26
- 229920006305 unsaturated polyester Polymers 0.000 description 20
- 238000002474 experimental method Methods 0.000 description 19
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 16
- 238000006116 polymerization reaction Methods 0.000 description 16
- 239000010408 film Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 239000000178 monomer Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 8
- 230000005855 radiation Effects 0.000 description 8
- 239000011521 glass Substances 0.000 description 7
- 230000009467 reduction Effects 0.000 description 7
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 239000005297 pyrex Substances 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 5
- 238000001879 gelation Methods 0.000 description 5
- 229920001567 vinyl ester resin Polymers 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical group C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 3
- IICCLYANAQEHCI-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 IICCLYANAQEHCI-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 229960002887 deanol Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000012188 paraffin wax 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
- 229930187593 rose bengal Natural products 0.000 description 3
- 229940081623 rose bengal Drugs 0.000 description 3
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- LRRQSCPPOIUNGX-UHFFFAOYSA-N 2-hydroxy-1,2-bis(4-methoxyphenyl)ethanone Chemical compound C1=CC(OC)=CC=C1C(O)C(=O)C1=CC=C(OC)C=C1 LRRQSCPPOIUNGX-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical group C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000011243 crosslinked material Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- MIJRFWVFNKQQDK-UHFFFAOYSA-N furoin Chemical compound C=1C=COC=1C(O)C(=O)C1=CC=CO1 MIJRFWVFNKQQDK-UHFFFAOYSA-N 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 230000002165 photosensitisation Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- YNANGXWUZWWFKX-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)ethane-1,2-dione Chemical compound C1=CC(OC)=CC=C1C(=O)C(=O)C1=CC=C(OC)C=C1 YNANGXWUZWWFKX-UHFFFAOYSA-N 0.000 description 1
- BCWCEHMHCDCJAD-UHFFFAOYSA-N 1,2-bis(4-methylphenyl)ethane-1,2-dione Chemical compound C1=CC(C)=CC=C1C(=O)C(=O)C1=CC=C(C)C=C1 BCWCEHMHCDCJAD-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- LHYQAEFVHIZFLR-UHFFFAOYSA-L 4-(4-diazonio-3-methoxyphenyl)-2-methoxybenzenediazonium;dichloride Chemical compound [Cl-].[Cl-].C1=C([N+]#N)C(OC)=CC(C=2C=C(OC)C([N+]#N)=CC=2)=C1 LHYQAEFVHIZFLR-UHFFFAOYSA-L 0.000 description 1
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 244000181025 Rosa gallica Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- HTKFORQRBXIQHD-UHFFFAOYSA-N allylthiourea Chemical compound NC(=S)NCC=C HTKFORQRBXIQHD-UHFFFAOYSA-N 0.000 description 1
- 229960001748 allylthiourea Drugs 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- 239000001055 blue pigment Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000000280 densification Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000001663 electronic absorption spectrum Methods 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
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- JGEMYUOFGVHXKV-UPHRSURJSA-N malealdehyde Chemical compound O=C\C=C/C=O JGEMYUOFGVHXKV-UPHRSURJSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- GUAWMXYQZKVRCW-UHFFFAOYSA-N n,2-dimethylaniline Chemical compound CNC1=CC=CC=C1C GUAWMXYQZKVRCW-UHFFFAOYSA-N 0.000 description 1
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical class CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- ZKDDJTYSFCWVGS-UHFFFAOYSA-M sodium;diethoxy-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Na+].CCOP([S-])(=S)OCC ZKDDJTYSFCWVGS-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical class CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
-
- 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
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/01—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to unsaturated polyesters
-
- 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
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/124—Carbonyl compound containing
-
- 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
- Y10S522/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S522/908—Dental utility
-
- 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
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/92—Polyurethane having terminal ethylenic unsaturation
-
- 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
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/921—Polyester having terminal ethylenic unsaturation other than polyesterurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Polymerisation Methods In General (AREA)
- Paints Or Removers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4836571 | 1971-10-18 | ||
| GB980772*[A GB1408265A (en) | 1971-10-18 | 1972-03-02 | Photopolymerisable composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE412396B SE412396B (sv) | 1980-03-03 |
| SE412396C true SE412396C (sv) | 1984-03-19 |
Family
ID=26243188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7213392A SE412396C (sv) | 1971-10-18 | 1972-10-17 | Fotopolymeriserbar komposition |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4071424B1 (ja) |
| JP (1) | JPS5410986B2 (ja) |
| AT (1) | AT331507B (ja) |
| BE (1) | BE789950A (ja) |
| CA (1) | CA984210A (ja) |
| CH (1) | CH593305A5 (ja) |
| DE (2) | DE2266023C2 (ja) |
| DK (1) | DK147708C (ja) |
| ES (1) | ES407740A1 (ja) |
| FR (1) | FR2156760B1 (ja) |
| GB (1) | GB1408265A (ja) |
| HK (1) | HK57478A (ja) |
| IT (1) | IT969627B (ja) |
| NL (1) | NL165570C (ja) |
| NO (1) | NO142915C (ja) |
| SE (1) | SE412396C (ja) |
Families Citing this family (199)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1412754A (en) * | 1971-12-29 | 1975-11-05 | Ici Ltd | Photopolymerisable composition |
| US4110184A (en) | 1973-04-24 | 1978-08-29 | Imperial Chemical Industries Limited | Photocurable dental filling compositions |
| US4089763A (en) | 1973-04-24 | 1978-05-16 | Imperial Chemical Industries Limited | Method of repairing teeth using a composition which is curable by irradiation with visible light |
| GB1469643A (en) * | 1973-11-19 | 1977-04-06 | Ici Ltd | Photopolymerisable composition |
| GB1485776A (en) * | 1974-01-10 | 1977-09-14 | Ici Ltd | Method of making a foamed article |
| US4069054A (en) * | 1975-09-02 | 1978-01-17 | Minnesota Mining And Manufacturing Company | Photopolymerizable composition containing a sensitized aromatic sulfonium compound and a cationacally polymerizable monomer |
| GB1553580A (en) * | 1975-11-21 | 1979-09-26 | Espe Pharm Praep | Photopolymerisable acrylic or methacrylic acid ester-containing compositions |
| DE2625538C2 (de) * | 1976-06-05 | 1984-03-22 | Basf Ag, 6700 Ludwigshafen | Photopolymerisierbare Überzugsmassen |
| DE2730462A1 (de) * | 1976-07-15 | 1978-01-19 | Ciba Geigy Ag | Photoinitiatoren fuer uv-haertbare massen |
| CA1117685A (en) * | 1976-11-15 | 1982-02-02 | Narayanan Madhavan | One paste polymeric dental restorative composition |
| JPS6026122B2 (ja) * | 1977-01-20 | 1985-06-21 | 富士写真フイルム株式会社 | 光重合性組成物 |
| DE2722264C2 (de) * | 1977-05-17 | 1984-06-28 | Merck Patent Gmbh, 6100 Darmstadt | Verwendung von substituierten Oxyalkylphenonen als Photosensibilisatoren |
| EP0003002B1 (de) * | 1977-12-22 | 1984-06-13 | Ciba-Geigy Ag | Verwendung von aromatisch-aliphatischen Ketonen als Photoinitiatoren, photopolymerisierbare Systeme enthaltend solche Ketone und neue aromatisch-aliphatische Ketone |
| JPS54130633A (en) * | 1978-04-01 | 1979-10-11 | Nippon Synthetic Chem Ind Co Ltd:The | Ultraviolet-curing coating composition |
| US4222835A (en) * | 1978-05-25 | 1980-09-16 | Westinghouse Electric Corp. | In depth curing of resins induced by UV radiation |
| US4234399A (en) * | 1978-10-13 | 1980-11-18 | Lord Corporation | Radiation curable compositions containing acyloin urethane compounds |
| JPS5565264A (en) * | 1978-11-08 | 1980-05-16 | Sumitomo Chem Co Ltd | Photo-setting composition and its photo-setting method |
| EP0012535B1 (en) * | 1978-12-18 | 1983-01-19 | Imperial Chemical Industries Plc | Dental compositions comprising a selected vinyl urethane prepolymer and processes for their manufacture |
| NO150963C (no) | 1979-01-11 | 1985-01-16 | Scott Bader Co | Polyesterharpiksmateriale som er herdbart ved hjelp av synlig lys, og fremgangsmaate til herding av dette |
| NO801021L (no) * | 1979-04-10 | 1980-10-13 | Akzo Nv | Ultrafiolett herdbart belegg. |
| DE3069349D1 (en) * | 1979-06-18 | 1984-11-08 | Eastman Kodak Co | Co-initiator compositions for photopolymerization containing 3-acyl-substituted coumarins, photopolymerizable composition and photographic element |
| DE3001616A1 (de) * | 1980-01-17 | 1981-07-23 | ESPE Fabrik pharmazeutischer Präparate GmbH, 8031 Seefeld | Verfahren zur herstellung von zahnersatzteilen durch photopolymerisieren einer verformbaren masse |
| DE3029276A1 (de) * | 1980-08-01 | 1982-02-18 | Etablissement Dentaire Ivoclar, Schaan | Photopolymerisierbare masse, insbesondere fuer dentalzwecke |
| US4553940A (en) * | 1980-08-29 | 1985-11-19 | Dentsply Research & Development Corp. | Visible light curable dental compositions |
| US4411625A (en) * | 1980-08-29 | 1983-10-25 | Dentsply Research & Development Corp. | Broad spectrum light curable dental compositions |
| US4491453A (en) * | 1980-08-29 | 1985-01-01 | Dentsply Research & Development Corp. | Process for restoring teeth with visible light curable compositions |
| ATE10502T1 (de) * | 1980-11-05 | 1984-12-15 | Akzo N.V. | Photopolymerisierbare zusammensetzung, mischung von photoinitiatoren und haertungsverfahren. |
| DE3172366D1 (en) | 1980-12-03 | 1985-10-24 | Ici Plc | Dental compositions |
| IL65159A0 (en) * | 1981-03-04 | 1982-05-31 | Ici Plc | Polymerisable dental compositions |
| USRE35264E (en) * | 1981-05-04 | 1996-06-04 | Dentsply Research & Development Corp. | Dental adhesive system |
| US4801528A (en) * | 1981-05-04 | 1989-01-31 | Dentsply Research & Development Corporation | Dental adhesive system |
| DE3136484A1 (de) * | 1981-09-15 | 1983-03-31 | Kulzer & Co Gmbh, 6380 Bad Homburg | "verfahren zur photopolymerisation von vinylverbindu ngen und photopolymerisierbares material" |
| DE3203096A1 (de) * | 1982-01-30 | 1983-08-04 | Merck Patent Gmbh, 6100 Darmstadt | Verwendung von hydroxyalkylphenonen als initiatoren fuer die strahlungshaertung waessriger prepolymerdispersionen |
| IE54502B1 (en) * | 1982-03-04 | 1989-10-25 | Ici Plc | Photopolymerisable compositions |
| DE3212379A1 (de) * | 1982-04-02 | 1983-10-20 | ESPE Fabrik pharmazeutischer Präparate GmbH, 8031 Seefeld | Geraet zum behandeln von dentalen werkstoffen |
| US4500657A (en) * | 1982-08-02 | 1985-02-19 | Johnson & Johnson Dental Products Company | Dental restorative compositions having improved mechanical properties and hydrolytic stability |
| DE3332179A1 (de) * | 1982-12-07 | 1984-06-07 | Kulzer & Co GmbH, 6393 Wehrheim | Grundiermasse |
| DE3301011A1 (de) * | 1983-01-14 | 1984-07-19 | Kulzer & Co GmbH, 6393 Wehrheim | Verfahren zur photopolymerisation von vinylverbindungen und photopolymerisierbares material (ii) |
| DE3301012A1 (de) * | 1983-01-14 | 1984-07-19 | Kulzer & Co GmbH, 6393 Wehrheim | Verfahren zur photopolymerisation von vinylverbindungen und photopolymerisierbares material |
| DE3301010A1 (de) * | 1983-01-14 | 1984-07-19 | Kulzer & Co GmbH, 6393 Wehrheim | Verfahren zur photopolymerisation von vinylverbindungen und photopolymerisierbares material |
| US4512340A (en) * | 1983-02-22 | 1985-04-23 | Johnson & Johnson Products, Inc. | Visible light cured orthopedic polymer casts |
| US4615665A (en) * | 1983-05-06 | 1986-10-07 | Dentsply International Inc. | Method for making dental prosthetic device with oxygen barrier layer and visible light irradiation to cure polymer |
| US4563438A (en) * | 1983-05-06 | 1986-01-07 | Ciba Geigy Corporation | Liquid mixture of photoinitiators |
| US4544467A (en) * | 1983-06-28 | 1985-10-01 | Minnesota Mining And Manufacturing Company | Light-curable dentin and enamel adhesive |
| US4525256A (en) * | 1983-07-01 | 1985-06-25 | Johnson & Johnson Dental Products Company | Photopolymerizable composition including catalyst comprising diketone plus 4-(N,N-dimethylamino)benzoic acid or ester thereof |
| DE3331157A1 (de) * | 1983-08-30 | 1985-03-14 | Basf Ag, 6700 Ludwigshafen | Photopolymerisierbare mischungen, enthaltend tertiaere amine als photoaktivatoren |
| US4863977A (en) * | 1983-11-16 | 1989-09-05 | Dentsply Research & Development Corp. | Process for preparing interpenetrating polymer network objects employing rubber-modified polymers |
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| US5210109A (en) * | 1983-11-16 | 1993-05-11 | Dentsply Research & Development Corp. | Interpenetrating polymer network compositions employing rubber-modified polymers |
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| US4604295A (en) * | 1983-12-22 | 1986-08-05 | Loctite Corporation | Visible light absorbing peroxy-esters |
| JPS60149603A (ja) * | 1984-01-17 | 1985-08-07 | Kuraray Co Ltd | 光重合性の組成物 |
| DE3414165A1 (de) * | 1984-04-14 | 1985-10-17 | Kulzer & Co GmbH, 6393 Wehrheim | Photopolymerisierbares dentales haftmittel |
| DE3414164A1 (de) * | 1984-04-14 | 1985-10-17 | Kulzer & Co GmbH, 6393 Wehrheim | Photopolymerisierbarer dentaler haftvermittler-lack |
| DE3414163A1 (de) * | 1984-04-14 | 1985-10-17 | Kulzer & Co GmbH, 6393 Wehrheim | Photopolymerisierbarer phosphathaltiger dentaler haftvermittler-lack |
| FI851910L (fi) * | 1984-05-14 | 1985-11-15 | Ici Plc | Aromatiska oligomerer. |
| US4657941A (en) * | 1984-11-29 | 1987-04-14 | Dentsply Research & Development Corp. | Biologically compatible adhesive containing a phosphorus adhesion promoter and a sulfinic accelerator |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA828150A (en) * | 1969-11-25 | B. Rust John | Photopolymers and the process of making same | |
| BE465271A (ja) * | 1941-12-31 | 1900-01-01 | ||
| US2548685A (en) * | 1946-12-21 | 1951-04-10 | Alexander H Kerr & Co Inc | Photopolymerization process and compositions |
| NL108006C (ja) * | 1957-05-17 | |||
| GB1090142A (en) * | 1965-02-26 | 1967-11-08 | Agfa Gevaert Nv | Photochemical insolubilisation of polymers |
| US3418118A (en) * | 1965-06-03 | 1968-12-24 | Du Pont | Photographic processes and products |
| US3495987A (en) * | 1965-09-03 | 1970-02-17 | Du Pont | Photopolymerizable products |
| US3558387A (en) * | 1966-06-10 | 1971-01-26 | Sun Chemical Corp | Radiation-curable compositions |
| DE1694930A1 (de) * | 1966-06-10 | 1971-10-21 | Sun Chemical Corp | Photopolymerisierbare Massen |
| US3551246A (en) * | 1967-07-10 | 1970-12-29 | Sun Chemical Corp | Radiation curable compositions |
| US3839171A (en) * | 1968-02-15 | 1974-10-01 | Asahi Chemical Ind | Unsaturated polyesters and laminates thereof |
| DE1769854C3 (de) * | 1968-07-26 | 1982-08-19 | Bayer Ag, 5090 Leverkusen | Photoinitiatoren und Verfahren zur Photopolymerisation |
| US3759807A (en) * | 1969-01-28 | 1973-09-18 | Union Carbide Corp | Photopolymerization process using combination of organic carbonyls and amines |
| CA935398A (en) * | 1969-01-28 | 1973-10-16 | L. Osborn Claiborn | Crosslinking process |
| JPS4818563B1 (ja) * | 1969-03-07 | 1973-06-07 | ||
| BE759041A (fr) * | 1969-11-18 | 1971-05-17 | Du Pont | Compositions photopolymerisables contenant des aminophenylcetones et des adjuvants |
| US3699022A (en) * | 1970-02-05 | 1972-10-17 | Reichhold Albert Chemie Ag | Photopolymerizable unsaturated polyesters containing benzoin-ether,organic acid ester,organic phosphine initiators |
| US3864133A (en) * | 1970-08-11 | 1975-02-04 | Dainippon Ink & Chemicals | Photo-polymerizable compositions |
| CA1013743A (en) * | 1972-01-05 | 1977-07-12 | George W. Borden | Acrylated epoxidized soybean oil compositions |
| US3729404A (en) * | 1971-09-10 | 1973-04-24 | Grace W R & Co | Photocurable polyene-polythiol polymers using a phosphine plus an additional sensitizer |
| JPS5034445B2 (ja) * | 1972-02-29 | 1975-11-08 | ||
| JPS5021933B2 (ja) * | 1972-04-19 | 1975-07-26 |
-
1972
- 1972-03-02 GB GB980772*[A patent/GB1408265A/en not_active Expired
- 1972-10-06 DK DK495272A patent/DK147708C/da not_active IP Right Cessation
- 1972-10-11 BE BE789950D patent/BE789950A/xx not_active IP Right Cessation
- 1972-10-12 NO NO3665/72A patent/NO142915C/no unknown
- 1972-10-13 CA CA153,924A patent/CA984210A/en not_active Expired
- 1972-10-17 IT IT30574/72A patent/IT969627B/it active
- 1972-10-17 FR FR7236748A patent/FR2156760B1/fr not_active Expired
- 1972-10-17 CH CH1515372A patent/CH593305A5/xx not_active IP Right Cessation
- 1972-10-17 SE SE7213392A patent/SE412396C/sv unknown
- 1972-10-18 DE DE2266023A patent/DE2266023C2/de not_active Expired
- 1972-10-18 JP JP10368972A patent/JPS5410986B2/ja not_active Expired
- 1972-10-18 ES ES407740A patent/ES407740A1/es not_active Expired
- 1972-10-18 NL NLAANVRAGE7214074,A patent/NL165570C/xx not_active IP Right Cessation
- 1972-10-18 AT AT891072A patent/AT331507B/de not_active IP Right Cessation
- 1972-10-18 DE DE2251048A patent/DE2251048C2/de not_active Expired - Lifetime
-
1975
- 1975-02-11 US US05549052 patent/US4071424B1/en not_active Expired - Lifetime
-
1978
- 1978-09-28 HK HK574/78A patent/HK57478A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL165570B (nl) | 1980-11-17 |
| DK147708C (da) | 1990-04-09 |
| GB1408265A (en) | 1975-10-01 |
| CH593305A5 (ja) | 1977-11-30 |
| ES407740A1 (es) | 1976-02-01 |
| AT331507B (de) | 1976-08-25 |
| NL165570C (nl) | 1983-02-16 |
| NO142915C (no) | 1980-11-12 |
| US4071424B1 (en) | 1995-07-18 |
| NO142915B (no) | 1980-08-04 |
| DK147708B (da) | 1984-11-19 |
| DE2266023C2 (ja) | 1989-07-20 |
| DE2251048C2 (de) | 1993-01-28 |
| DE2251048A1 (de) | 1973-05-10 |
| BE789950A (fr) | 1973-04-11 |
| CA984210A (en) | 1976-02-24 |
| FR2156760B1 (ja) | 1979-01-26 |
| US4071424A (en) | 1978-01-31 |
| HK57478A (en) | 1978-10-06 |
| JPS5410986B2 (ja) | 1979-05-11 |
| SE412396B (sv) | 1980-03-03 |
| JPS4849875A (ja) | 1973-07-13 |
| FR2156760A1 (ja) | 1973-06-01 |
| IT969627B (it) | 1974-04-10 |
| NL7214074A (ja) | 1973-04-24 |
| ATA891072A (de) | 1975-11-15 |
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