JPH0529234B2 - - Google Patents
Info
- Publication number
- JPH0529234B2 JPH0529234B2 JP60265962A JP26596285A JPH0529234B2 JP H0529234 B2 JPH0529234 B2 JP H0529234B2 JP 60265962 A JP60265962 A JP 60265962A JP 26596285 A JP26596285 A JP 26596285A JP H0529234 B2 JPH0529234 B2 JP H0529234B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- naphthyl
- phenyl
- biphenylyl
- cyclopentyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 28
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 27
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 19
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 15
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 13
- 239000003999 initiator Substances 0.000 claims abstract description 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 12
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 11
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 9
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 6
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims abstract description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract description 4
- -1 biphenylyl group Chemical group 0.000 claims description 44
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000002704 decyl group Chemical group [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])* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 2
- DNRISHWSPBDRTH-UHFFFAOYSA-N [(2,6-dichlorobenzoyl)-phenylphosphoryl]-(2,6-dichlorophenyl)methanone Chemical compound ClC1=CC=CC(Cl)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(Cl)C=CC=C1Cl DNRISHWSPBDRTH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- GEHDMHDFJOLWCL-UHFFFAOYSA-N CCCP(=O)C1=CC=CC=C1 Chemical compound CCCP(=O)C1=CC=CC=C1 GEHDMHDFJOLWCL-UHFFFAOYSA-N 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract description 3
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- PRRGXULZOZTZDK-UHFFFAOYSA-N [(2,6-dichlorobenzoyl)-(2,5-dimethylphenyl)phosphoryl]-(2,6-dichlorophenyl)methanone Chemical compound CC1=CC=C(C)C(P(=O)(C(=O)C=2C(=CC=CC=2Cl)Cl)C(=O)C=2C(=CC=CC=2Cl)Cl)=C1 PRRGXULZOZTZDK-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 241000183024 Populus tremula Species 0.000 description 2
- VLMHTHBOGIBJTA-UHFFFAOYSA-N [(2,6-dichlorobenzoyl)-(2,5-dimethylphenyl)phosphanyl]-(2,6-dichlorophenyl)methanone Chemical compound CC1=CC=C(C)C(P(C(=O)C=2C(=CC=CC=2Cl)Cl)C(=O)C=2C(=CC=CC=2Cl)Cl)=C1 VLMHTHBOGIBJTA-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000005548 dental material Substances 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 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 2
- 239000007800 oxidant agent Substances 0.000 description 2
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- IPOXZBCXKICZEH-UHFFFAOYSA-N (2,5-dimethylphenyl)phosphane Chemical compound CC1=CC=C(C)C(P)=C1 IPOXZBCXKICZEH-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- JBLIDPPHFGWTKU-UHFFFAOYSA-N 2,6-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=C(Cl)C=CC=C1Cl JBLIDPPHFGWTKU-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical group 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
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 1
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical compound OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 1
- 238000004679 31P NMR spectroscopy Methods 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- GVOUFPWUYJWQSK-UHFFFAOYSA-N Cyclofenil Chemical class C1=CC(OC(=O)C)=CC=C1C(C=1C=CC(OC(C)=O)=CC=1)=C1CCCCC1 GVOUFPWUYJWQSK-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- NKJRPAWZCFIXFA-UHFFFAOYSA-N [(2,5-dimethylphenyl)-(2-methylnaphthalene-1-carbonyl)phosphoryl]-(2-methylnaphthalen-1-yl)methanone Chemical compound CC1=CC=C(C)C(P(=O)(C(=O)C=2C3=CC=CC=C3C=CC=2C)C(=O)C=2C3=CC=CC=C3C=CC=2C)=C1 NKJRPAWZCFIXFA-UHFFFAOYSA-N 0.000 description 1
- GITYWRPNRUSIOF-UHFFFAOYSA-N [(2,6-dichloro-3,4,5-trimethoxybenzoyl)-(2,5-dimethylphenyl)phosphoryl]-(2,6-dichloro-3,4,5-trimethoxyphenyl)methanone Chemical compound COC1=C(OC)C(OC)=C(Cl)C(C(=O)P(=O)(C(=O)C=2C(=C(OC)C(OC)=C(OC)C=2Cl)Cl)C=2C(=CC=C(C)C=2)C)=C1Cl GITYWRPNRUSIOF-UHFFFAOYSA-N 0.000 description 1
- UFROOKCLMGWXKA-UHFFFAOYSA-N [(2,6-dichloro-3,4,5-trimethoxybenzoyl)-(4-ethoxyphenyl)phosphoryl]-(2,6-dichloro-3,4,5-trimethoxyphenyl)methanone Chemical compound C1=CC(OCC)=CC=C1P(=O)(C(=O)C=1C(=C(OC)C(OC)=C(OC)C=1Cl)Cl)C(=O)C1=C(Cl)C(OC)=C(OC)C(OC)=C1Cl UFROOKCLMGWXKA-UHFFFAOYSA-N 0.000 description 1
- QPZWOFKFESGNEY-UHFFFAOYSA-N [(2,6-dichlorobenzoyl)-(2,4-dimethoxyphenyl)phosphoryl]-(2,6-dichlorophenyl)methanone Chemical compound COC1=CC(OC)=CC=C1P(=O)(C(=O)C=1C(=CC=CC=1Cl)Cl)C(=O)C1=C(Cl)C=CC=C1Cl QPZWOFKFESGNEY-UHFFFAOYSA-N 0.000 description 1
- UICKNOJKFHBQOK-UHFFFAOYSA-N [(2,6-dichlorobenzoyl)-(4-octylphenyl)phosphoryl]-(2,6-dichlorophenyl)methanone Chemical compound C1=CC(CCCCCCCC)=CC=C1P(=O)(C(=O)C=1C(=CC=CC=1Cl)Cl)C(=O)C1=C(Cl)C=CC=C1Cl UICKNOJKFHBQOK-UHFFFAOYSA-N 0.000 description 1
- ZEDSKTISNTXEQI-UHFFFAOYSA-N [(2,6-dichlorobenzoyl)-(4-propylphenyl)phosphoryl]-(2,6-dichlorophenyl)methanone Chemical compound C1=CC(CCC)=CC=C1P(=O)(C(=O)C=1C(=CC=CC=1Cl)Cl)C(=O)C1=C(Cl)C=CC=C1Cl ZEDSKTISNTXEQI-UHFFFAOYSA-N 0.000 description 1
- YNJCLWHSZGZEAS-UHFFFAOYSA-N [(2,6-dichlorobenzoyl)-naphthalen-1-ylphosphoryl]-(2,6-dichlorophenyl)methanone Chemical compound ClC1=CC=CC(Cl)=C1C(=O)P(=O)(C=1C2=CC=CC=C2C=CC=1)C(=O)C1=C(Cl)C=CC=C1Cl YNJCLWHSZGZEAS-UHFFFAOYSA-N 0.000 description 1
- NXUGFMLCLHCQHS-UHFFFAOYSA-N [(2,6-dichlorobenzoyl)-naphthalen-2-ylphosphoryl]-(2,6-dichlorophenyl)methanone Chemical compound ClC1=CC=CC(Cl)=C1C(=O)P(=O)(C=1C=C2C=CC=CC2=CC=1)C(=O)C1=C(Cl)C=CC=C1Cl NXUGFMLCLHCQHS-UHFFFAOYSA-N 0.000 description 1
- ZTCAGYRXUCWHPV-UHFFFAOYSA-N [(2,6-dimethoxybenzoyl)-(2,5-dimethylphenyl)phosphoryl]-(2,6-dimethoxyphenyl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)P(=O)(C=1C(=CC=C(C)C=1)C)C(=O)C1=C(OC)C=CC=C1OC ZTCAGYRXUCWHPV-UHFFFAOYSA-N 0.000 description 1
- QISAYNXDUCNISJ-UHFFFAOYSA-N [(2,6-dimethoxybenzoyl)-phenylphosphoryl]-(2,6-dimethoxyphenyl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(OC)C=CC=C1OC QISAYNXDUCNISJ-UHFFFAOYSA-N 0.000 description 1
- GXJKNAVNRPLLPC-UHFFFAOYSA-N [(2-methylnaphthalene-1-carbonyl)-(4-phenylphenyl)phosphoryl]-(2-methylnaphthalen-1-yl)methanone Chemical compound CC1=CC=C2C=CC=CC2=C1C(=O)P(=O)(C(=O)C=1C2=CC=CC=C2C=CC=1C)C(C=C1)=CC=C1C1=CC=CC=C1 GXJKNAVNRPLLPC-UHFFFAOYSA-N 0.000 description 1
- DAYIUENWMHVSAH-UHFFFAOYSA-N [(2-methylnaphthalene-1-carbonyl)-(4-propylphenyl)phosphoryl]-(2-methylnaphthalen-1-yl)methanone Chemical compound C1=CC(CCC)=CC=C1P(=O)(C(=O)C=1C2=CC=CC=C2C=CC=1C)C(=O)C1=C(C)C=CC2=CC=CC=C12 DAYIUENWMHVSAH-UHFFFAOYSA-N 0.000 description 1
- NAZRXCOYVXLVLT-UHFFFAOYSA-N [(2-methylnaphthalene-1-carbonyl)-naphthalen-2-ylphosphoryl]-(2-methylnaphthalen-1-yl)methanone Chemical compound C1=CC=CC2=CC(P(=O)(C(=O)C=3C4=CC=CC=C4C=CC=3C)C(=O)C3=C4C=CC=CC4=CC=C3C)=CC=C21 NAZRXCOYVXLVLT-UHFFFAOYSA-N 0.000 description 1
- VWGHOMFQYUCRSK-UHFFFAOYSA-N [(2-methylnaphthalene-1-carbonyl)-phenylphosphoryl]-(2-methylnaphthalen-1-yl)methanone Chemical compound CC1=CC=C2C=CC=CC2=C1C(=O)P(=O)(C(=O)C=1C2=CC=CC=C2C=CC=1C)C1=CC=CC=C1 VWGHOMFQYUCRSK-UHFFFAOYSA-N 0.000 description 1
- VSCYSXBQCDNELJ-UHFFFAOYSA-N [(4-chlorophenyl)-(2,6-dichlorobenzoyl)phosphoryl]-(2,6-dichlorophenyl)methanone Chemical compound C1=CC(Cl)=CC=C1P(=O)(C(=O)C=1C(=CC=CC=1Cl)Cl)C(=O)C1=C(Cl)C=CC=C1Cl VSCYSXBQCDNELJ-UHFFFAOYSA-N 0.000 description 1
- PDDQIFJFEBLVOX-UHFFFAOYSA-N [(4-ethoxyphenyl)-(2-methoxynaphthalene-1-carbonyl)phosphoryl]-(2-methoxynaphthalen-1-yl)methanone Chemical compound C1=CC(OCC)=CC=C1P(=O)(C(=O)C=1C2=CC=CC=C2C=CC=1OC)C(=O)C1=C(OC)C=CC2=CC=CC=C12 PDDQIFJFEBLVOX-UHFFFAOYSA-N 0.000 description 1
- LADQLHXGCZOGFM-UHFFFAOYSA-N [(4-ethoxyphenyl)-(2-methylnaphthalene-1-carbonyl)phosphoryl]-(2-methylnaphthalen-1-yl)methanone Chemical compound C1=CC(OCC)=CC=C1P(=O)(C(=O)C=1C2=CC=CC=C2C=CC=1C)C(=O)C1=C(C)C=CC2=CC=CC=C12 LADQLHXGCZOGFM-UHFFFAOYSA-N 0.000 description 1
- ZZAGLMPBQOKGGT-UHFFFAOYSA-N [4-[4-(4-prop-2-enoyloxybutoxy)benzoyl]oxyphenyl] 4-(4-prop-2-enoyloxybutoxy)benzoate Chemical compound C1=CC(OCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1)=CC=C1OC(=O)C1=CC=C(OCCCCOC(=O)C=C)C=C1 ZZAGLMPBQOKGGT-UHFFFAOYSA-N 0.000 description 1
- OIQNLDFONGLCHE-UHFFFAOYSA-N [decyl-(2,6-dichlorobenzoyl)phosphoryl]-(2,6-dichlorophenyl)methanone Chemical compound ClC=1C=CC=C(Cl)C=1C(=O)P(=O)(CCCCCCCCCC)C(=O)C1=C(Cl)C=CC=C1Cl OIQNLDFONGLCHE-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000007656 barbituric acids Chemical class 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000006267 biphenyl group Chemical class 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis 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
- 239000000945 filler Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000013047 polymeric layer Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003452 sulfinic acid derivatives Chemical class 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5397—Phosphine oxides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
- A61K6/62—Photochemical radical initiators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5337—Phosphine oxides or thioxides containing the structure -C(=X)-P(=X) or NC-P(=X) (X = O, S, Se)
-
- 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
- Y10S430/106—Binder containing
- Y10S430/111—Polymer of unsaturated acid or ester
-
- 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
- Y10S430/122—Sulfur compound containing
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Polymers & Plastics (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Biophysics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Polymerisation Methods In General (AREA)
- Dental Preparations (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843443221 DE3443221A1 (de) | 1984-11-27 | 1984-11-27 | Bisacylphosphinoxide, ihre herstellung und verwendung |
| DE3443221.3 | 1984-11-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61130296A JPS61130296A (ja) | 1986-06-18 |
| JPH0529234B2 true JPH0529234B2 (https=) | 1993-04-28 |
Family
ID=6251283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60265962A Granted JPS61130296A (ja) | 1984-11-27 | 1985-11-25 | ビスアシルホスフインオキサイドおよびその製造法並びに使用法 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US4737593A (https=) |
| EP (1) | EP0184095B1 (https=) |
| JP (1) | JPS61130296A (https=) |
| AT (1) | ATE44383T1 (https=) |
| DE (2) | DE3443221A1 (https=) |
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| EP2042568A1 (en) | 2007-09-26 | 2009-04-01 | FUJIFILM Corporation | Ink composition, inkjet recording method, and printed material |
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| EP2042573A1 (en) | 2007-09-28 | 2009-04-01 | FUJIFILM Corporation | Ink composition |
| EP2042563A1 (en) | 2007-09-25 | 2009-04-01 | FUJIFILM Corporation | Photocurable coating composition, and overprint and process for producing same |
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|---|---|---|---|---|
| DE3443221A1 (de) * | 1984-11-27 | 1986-06-05 | ESPE Fabrik pharmazeutischer Präparate GmbH, 8031 Seefeld | Bisacylphosphinoxide, ihre herstellung und verwendung |
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| DE3837569A1 (de) * | 1988-11-04 | 1990-05-10 | Espe Stiftung | Mit sichtbarem licht aushaertbare dentalmassen |
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| DE2012221A1 (de) * | 1970-03-14 | 1971-09-23 | Basf Ag | Oxyphosphorane enthaltende photopolymerisierbare Massen |
| US3668093A (en) * | 1971-05-06 | 1972-06-06 | Du Pont | Photoinitiation of vinyl polymerization by triaroylphosphines |
| DE2909993A1 (de) * | 1979-03-14 | 1980-10-02 | Basf Ag | Lichthaertbare form-, traenk- und ueberzugsmassen |
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| DE3023486A1 (de) * | 1980-06-24 | 1982-01-07 | Bayer Ag, 5090 Leverkusen | Photopolymerisierbare mischungen mit aroylphosphonsaeureestern als photoinitiatoren |
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| DE3114341A1 (de) * | 1981-04-09 | 1982-11-11 | Basf Ag, 6700 Ludwigshafen | Acylphosphinverbindungen, ihre herstellung und verwendung |
| DE3133419A1 (de) * | 1981-08-24 | 1983-03-10 | Basf Ag, 6700 Ludwigshafen | Acylphosphinoxidverbindungen und ihre verwendung |
| DE3236026A1 (de) * | 1982-09-29 | 1984-03-29 | Basf Ag, 6700 Ludwigshafen | Photopolymerisierbare massen und ihre verwendung |
| DE3443221A1 (de) * | 1984-11-27 | 1986-06-05 | ESPE Fabrik pharmazeutischer Präparate GmbH, 8031 Seefeld | Bisacylphosphinoxide, ihre herstellung und verwendung |
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- 1985-11-25 EP EP85114908A patent/EP0184095B1/de not_active Expired
- 1985-11-25 AT AT85114908T patent/ATE44383T1/de not_active IP Right Cessation
- 1985-11-25 JP JP60265962A patent/JPS61130296A/ja active Granted
- 1985-11-25 DE DE8585114908T patent/DE3571322D1/de not_active Expired
- 1985-11-25 US US06/801,339 patent/US4737593A/en not_active Expired - Lifetime
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Also Published As
| Publication number | Publication date |
|---|---|
| JPS61130296A (ja) | 1986-06-18 |
| US4737593A (en) | 1988-04-12 |
| EP0184095B1 (de) | 1989-07-05 |
| ATE44383T1 (de) | 1989-07-15 |
| DE3443221A1 (de) | 1986-06-05 |
| US4792632A (en) | 1988-12-20 |
| EP0184095A2 (de) | 1986-06-11 |
| DE3571322D1 (en) | 1989-08-10 |
| EP0184095A3 (en) | 1987-04-22 |
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