BE1014218A5 - Monoacylalkylphosphines organometalliques, leur preparation et leur utilisation comme produits de depart dans la preparation de phosphines, leurs oxydes ou leurs sulfures. - Google Patents
Monoacylalkylphosphines organometalliques, leur preparation et leur utilisation comme produits de depart dans la preparation de phosphines, leurs oxydes ou leurs sulfures. Download PDFInfo
- Publication number
- BE1014218A5 BE1014218A5 BE2001/0389A BE200100389A BE1014218A5 BE 1014218 A5 BE1014218 A5 BE 1014218A5 BE 2001/0389 A BE2001/0389 A BE 2001/0389A BE 200100389 A BE200100389 A BE 200100389A BE 1014218 A5 BE1014218 A5 BE 1014218A5
- Authority
- BE
- Belgium
- Prior art keywords
- group
- oxide
- alkyl
- substituted
- phosphine
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 65
- 150000003568 thioethers Chemical class 0.000 title claims description 15
- 150000003003 phosphines Chemical class 0.000 title claims description 12
- 125000002524 organometallic group Chemical group 0.000 title description 3
- -1 OR11 Chemical group 0.000 claims abstract description 790
- 150000001875 compounds Chemical class 0.000 claims abstract description 189
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 120
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 58
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 44
- 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 44
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract description 41
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 32
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 23
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract description 22
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 21
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 21
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 20
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 14
- 150000002367 halogens Chemical class 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 10
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 10
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 claims abstract description 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 3
- 239000004305 biphenyl Substances 0.000 claims abstract description 3
- 125000006755 (C2-C20) alkyl group Chemical group 0.000 claims abstract 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 786
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 404
- 239000000203 mixture Substances 0.000 claims description 93
- 125000005843 halogen group Chemical group 0.000 claims description 88
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 79
- 238000006243 chemical reaction Methods 0.000 claims description 65
- 238000000576 coating method Methods 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 44
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 41
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 40
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 37
- 239000000463 material Substances 0.000 claims description 37
- 230000008569 process Effects 0.000 claims description 34
- 125000006539 C12 alkyl 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])C([H])([H])C([H])([H])* 0.000 claims description 32
- 150000001266 acyl halides Chemical class 0.000 claims description 32
- 239000003999 initiator Substances 0.000 claims description 30
- 125000004429 atom Chemical group 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 238000004519 manufacturing process Methods 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 229910052801 chlorine Inorganic materials 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 23
- 238000007639 printing Methods 0.000 claims description 22
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 21
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 239000000976 ink Substances 0.000 claims description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
- 229910052794 bromium Inorganic materials 0.000 claims description 19
- 239000001301 oxygen Substances 0.000 claims description 19
- 238000007254 oxidation reaction Methods 0.000 claims description 18
- 229920000642 polymer Polymers 0.000 claims description 18
- 239000000843 powder Substances 0.000 claims description 18
- 230000003647 oxidation Effects 0.000 claims description 17
- 239000000758 substrate Substances 0.000 claims description 17
- 239000000654 additive Substances 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 239000007858 starting material Substances 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 15
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 claims description 13
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 claims description 13
- 230000003287 optical effect Effects 0.000 claims description 13
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 12
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims description 10
- REJGOFYVRVIODZ-UHFFFAOYSA-N phosphanium;chloride Chemical compound P.Cl REJGOFYVRVIODZ-UHFFFAOYSA-N 0.000 claims description 10
- 238000007650 screen-printing Methods 0.000 claims description 10
- 238000005987 sulfurization reaction Methods 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 9
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 238000007645 offset printing Methods 0.000 claims description 9
- 125000004350 aryl cycloalkyl group Chemical group 0.000 claims description 8
- 239000002131 composite material Substances 0.000 claims description 8
- 125000005724 cycloalkenylene group Chemical group 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 239000003365 glass fiber Substances 0.000 claims description 7
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 238000002845 discoloration Methods 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000006267 biphenyl group Chemical group 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
- 239000000853 adhesive Substances 0.000 claims description 4
- 230000001070 adhesive effect Effects 0.000 claims description 4
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 4
- 238000005538 encapsulation Methods 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 239000003094 microcapsule Substances 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 229940037201 oris Drugs 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 4
- 230000033458 reproduction Effects 0.000 claims description 4
- 125000005504 styryl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 238000012360 testing method Methods 0.000 claims description 4
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 230000001678 irradiating effect Effects 0.000 claims description 3
- 150000002900 organolithium compounds Chemical class 0.000 claims description 3
- BNJMRELGMDUDDB-UHFFFAOYSA-N $l^{1}-sulfanylbenzene Chemical compound [S]C1=CC=CC=C1 BNJMRELGMDUDDB-UHFFFAOYSA-N 0.000 claims description 2
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 2
- 125000006538 C11 alkyl 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])C([H])([H])* 0.000 claims description 2
- 240000007594 Oryza sativa Species 0.000 claims description 2
- 235000007164 Oryza sativa Nutrition 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Chemical group C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 2
- 235000009566 rice Nutrition 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000005548 dental material Substances 0.000 claims 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims 1
- AWGSLTUSOFTBSM-UHFFFAOYSA-N COC1=C(C(=O)P(CCCC)C(C2=C(C=C(C=C2C)C)C)=O)C(=CC=C1)OC Chemical compound COC1=C(C(=O)P(CCCC)C(C2=C(C=C(C=C2C)C)C)=O)C(=CC=C1)OC AWGSLTUSOFTBSM-UHFFFAOYSA-N 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims 1
- 239000000796 flavoring agent Substances 0.000 claims 1
- 235000019634 flavors Nutrition 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- BZQFBWGGLXLEPQ-REOHCLBHSA-N phosphoserine Chemical compound OC(=O)[C@@H](N)COP(O)(O)=O BZQFBWGGLXLEPQ-REOHCLBHSA-N 0.000 description 741
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 226
- 239000002253 acid Substances 0.000 description 121
- ZVGDDAJTNHDDNN-UHFFFAOYSA-N (2,6-dimethoxybenzoyl) 2,6-dimethoxybenzoate Chemical compound COC1=CC=CC(OC)=C1C(=O)OC(=O)C1=C(OC)C=CC=C1OC ZVGDDAJTNHDDNN-UHFFFAOYSA-N 0.000 description 72
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 65
- 150000002148 esters Chemical class 0.000 description 59
- XVZXOLOFWKSDSR-UHFFFAOYSA-N Cc1cc(C)c([C]=O)c(C)c1 Chemical group Cc1cc(C)c([C]=O)c(C)c1 XVZXOLOFWKSDSR-UHFFFAOYSA-N 0.000 description 51
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 48
- 150000003254 radicals Chemical class 0.000 description 46
- QFFZKDVGFYREPN-UHFFFAOYSA-N (2,4,6-trimethylbenzoyl) 2,4,6-trimethylbenzoate Chemical compound CC1=CC(C)=CC(C)=C1C(=O)OC(=O)C1=C(C)C=C(C)C=C1C QFFZKDVGFYREPN-UHFFFAOYSA-N 0.000 description 41
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 27
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 26
- 239000011248 coating agent Substances 0.000 description 25
- XJIUVODGEPHQNI-UHFFFAOYSA-N CC1=CC(=C(C(=C1)C)C(=O)C2(CCCCC2)OC3(CCCCC3)C(=O)C4=C(C=C(C=C4C)C)C)C Chemical compound CC1=CC(=C(C(=C1)C)C(=O)C2(CCCCC2)OC3(CCCCC3)C(=O)C4=C(C=C(C=C4C)C)C)C XJIUVODGEPHQNI-UHFFFAOYSA-N 0.000 description 22
- 239000000460 chlorine Substances 0.000 description 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 22
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 21
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 20
- FGKJLKRYENPLQH-UHFFFAOYSA-N isocaproic acid Chemical compound CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 0.000 description 19
- NPSJHQMIVNJLNN-UHFFFAOYSA-N 2-ethylhexyl 4-nitrobenzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=C([N+]([O-])=O)C=C1 NPSJHQMIVNJLNN-UHFFFAOYSA-N 0.000 description 17
- 239000004808 2-ethylhexylester Substances 0.000 description 17
- 229920001577 copolymer Polymers 0.000 description 17
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- XFMPEIBTNAPWGX-UHFFFAOYSA-N (2,6-dimethylbenzoyl) 2,6-dimethylbenzoate Chemical compound CC1=CC=CC(C)=C1C(=O)OC(=O)C1=C(C)C=CC=C1C XFMPEIBTNAPWGX-UHFFFAOYSA-N 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- 239000000049 pigment Substances 0.000 description 13
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 13
- CRVFKSHHTIWWDT-UHFFFAOYSA-N CC1=CC(=C(C(=C1)C)C(=O)C2(CCCC2)OC3(CCCC3)C(=O)C4=C(C=C(C=C4C)C)C)C Chemical compound CC1=CC(=C(C(=C1)C)C(=O)C2(CCCC2)OC3(CCCC3)C(=O)C4=C(C=C(C=C4C)C)C)C CRVFKSHHTIWWDT-UHFFFAOYSA-N 0.000 description 12
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- 125000004494 ethyl ester group Chemical group 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- BCOFXCDKRLOQHP-UHFFFAOYSA-N (2,4,6-trimethoxybenzoyl) 2,4,6-trimethoxybenzoate Chemical compound COC1=CC(OC)=CC(OC)=C1C(=O)OC(=O)C1=C(OC)C=C(OC)C=C1OC BCOFXCDKRLOQHP-UHFFFAOYSA-N 0.000 description 11
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 11
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 239000000178 monomer Substances 0.000 description 11
- 229920005862 polyol Polymers 0.000 description 11
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 11
- 239000000975 dye Substances 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 150000001335 aliphatic alkanes Chemical class 0.000 description 9
- 125000004414 alkyl thio group Chemical group 0.000 description 9
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 9
- 238000001723 curing Methods 0.000 description 9
- 229920000728 polyester Polymers 0.000 description 9
- 150000003077 polyols Chemical class 0.000 description 9
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- MWNJKOJSSJECBU-UHFFFAOYSA-N CC(C)(C)C1=CC(C)=C(C(OC(C2=C(C)C=C(C(C)(C)C)C=C2C)=O)=O)C(C)=C1 Chemical compound CC(C)(C)C1=CC(C)=C(C(OC(C2=C(C)C=C(C(C)(C)C)C=C2C)=O)=O)C(C)=C1 MWNJKOJSSJECBU-UHFFFAOYSA-N 0.000 description 8
- JWZYTSWEYGKGPD-UHFFFAOYSA-N CC1=CC(=C(C(=C1)C)C(=O)C(C(C)C)OC(C(C)C)C(=O)C2=C(C=C(C=C2C)C)C)C Chemical compound CC1=CC(=C(C(=C1)C)C(=O)C(C(C)C)OC(C(C)C)C(=O)C2=C(C=C(C=C2C)C)C)C JWZYTSWEYGKGPD-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 8
- 238000000465 moulding Methods 0.000 description 8
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 8
- 229920002120 photoresistant polymer Polymers 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
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Classifications
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- G—PHYSICS
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- 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
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- C—CHEMISTRY; METALLURGY
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
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- G—PHYSICS
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- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
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- 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
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- 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
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- Y10T428/00—Stock material or miscellaneous articles
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- Materials For Photolithography (AREA)
- Paints Or Removers (AREA)
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- Macromonomer-Based Addition Polymer (AREA)
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| AU2002366198A1 (en) * | 2001-11-20 | 2003-06-10 | Ciba Specialty Chemicals Holding Inc. | Multimer forms of acylphosphines and their derivatives |
| ATE535009T1 (de) | 2002-05-08 | 2011-12-15 | Phoseon Technology Inc | Hocheffiziente halbleiter-lichtquelle sowie verfahren zu deren verwendung und herstellung |
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| DK1106627T3 (da) | 1999-12-08 | 2004-02-23 | Ciba Sc Holding Ag | Hidtil ukendte fotoinitiatorsystem af phosphinoxider og hærdbare sammensætninger med lav farve |
| JP2001200007A (ja) * | 2000-01-19 | 2001-07-24 | Shin Etsu Chem Co Ltd | 光硬化性樹脂組成物及び光ファイバー用被覆材 |
| GB2360283B (en) * | 2000-02-08 | 2002-08-21 | Ciba Sc Holding Ag | Monoacylarylphosphines and acylphosphine oxides and sulphides |
| GB2365430B (en) * | 2000-06-08 | 2002-08-28 | Ciba Sc Holding Ag | Acylphosphine photoinitiators and intermediates |
-
2001
- 2001-05-24 GB GB0112580A patent/GB2365430B/en not_active Expired - Fee Related
- 2001-05-31 US US09/871,373 patent/US6737549B2/en not_active Expired - Fee Related
- 2001-06-05 DE DE10127171A patent/DE10127171A1/de not_active Withdrawn
- 2001-06-06 TW TW090113664A patent/TWI268932B/zh not_active IP Right Cessation
- 2001-06-06 CA CA002349829A patent/CA2349829A1/en not_active Abandoned
- 2001-06-07 KR KR1020010031746A patent/KR100829076B1/ko not_active Expired - Fee Related
- 2001-06-07 ES ES200101326A patent/ES2194584B1/es not_active Expired - Fee Related
- 2001-06-07 CN CNB011208988A patent/CN1198831C/zh not_active Expired - Fee Related
- 2001-06-07 IT IT2001MI001201A patent/ITMI20011201A1/it unknown
- 2001-06-07 FR FR0107438A patent/FR2810041B1/fr not_active Expired - Fee Related
- 2001-06-07 BE BE2001/0389A patent/BE1014218A5/fr not_active IP Right Cessation
- 2001-06-08 NL NL1018251A patent/NL1018251C2/nl not_active IP Right Cessation
- 2001-06-08 BR BRPI0102319-5A patent/BR0102319B1/pt not_active IP Right Cessation
- 2001-06-08 JP JP2001174045A patent/JP4850353B2/ja not_active Expired - Fee Related
- 2001-06-08 MX MXPA01005780A patent/MXPA01005780A/es active IP Right Grant
-
2002
- 2002-10-25 US US10/280,820 patent/US6969733B2/en not_active Expired - Fee Related
- 2002-10-25 US US10/280,819 patent/US7026017B2/en not_active Expired - Fee Related
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2011
- 2011-06-15 JP JP2011133344A patent/JP2011251965A/ja active Pending
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| EP0184095A2 (de) * | 1984-11-27 | 1986-06-11 | ESPE Stiftung & Co Produktions- und Vertriebs KG | Bisacylphosphinoxide, ihre Herstellung und Verwendung |
| EP0615980A2 (de) * | 1993-03-18 | 1994-09-21 | Ciba-Geigy Ag | Härtung von Bisacylphosphinoxid-Photoinitiatoren enthaltenden Zusammensetzungen |
| GB2292740A (en) * | 1994-09-02 | 1996-03-06 | Ciba Geigy Ag | Alkoxyphenyl-substituted bisacylphosphine oxides |
| GB2310855A (en) * | 1996-03-04 | 1997-09-10 | Ciba Geigy Ag | Alkylphenylbisacylphosphine oxides and photoinitiator mixtures |
| WO2000032612A1 (en) * | 1998-11-30 | 2000-06-08 | Ciba Specialty Chemicals Holding Inc. | Process for preparing acylphosphines and derivatives |
Non-Patent Citations (2)
| Title |
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| ISSLEIB K ET AL: "SEKUNDAERE CARBONSAEUREPHOSPHIDE R-CO-PH-R", ZEITSCHRIFT FUR NATURFORSCHUNG, TEIL B: ANORGANISCHE CHEMIE, ORGANISCHE CHEMIE, VERLAG DER ZEITSCHRIFT FUR NATURFORSCHUNG. TUBINGEN, DE, vol. 22, no. 7, 1967, pages 784 - 785, XP001053016, ISSN: 0932-0776 * |
| LIOTTA C L ET AL: "The synthesis and reactions of potassium benzoylphosphide, benzoylphosphine and benzoylmethyl- phosphine", TETRAHEDRON LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 25, no. 12, 1984, pages 1249 - 1252, XP002191367, ISSN: 0040-4039 * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE10127171A1 (de) | 2001-12-13 |
| ES2194584A1 (es) | 2003-11-16 |
| NL1018251C2 (nl) | 2002-02-18 |
| CN1329005A (zh) | 2002-01-02 |
| KR20010111021A (ko) | 2001-12-15 |
| JP4850353B2 (ja) | 2012-01-11 |
| TWI268932B (en) | 2006-12-21 |
| JP2011251965A (ja) | 2011-12-15 |
| CN1198831C (zh) | 2005-04-27 |
| NL1018251A1 (nl) | 2001-12-14 |
| GB0112580D0 (en) | 2001-07-18 |
| JP2002069085A (ja) | 2002-03-08 |
| KR100829076B1 (ko) | 2008-05-14 |
| BR0102319B1 (pt) | 2012-05-29 |
| GB2365430B (en) | 2002-08-28 |
| FR2810041B1 (fr) | 2009-04-17 |
| US20030139485A1 (en) | 2003-07-24 |
| US20030130370A1 (en) | 2003-07-10 |
| ITMI20011201A1 (it) | 2002-12-07 |
| MXPA01005780A (es) | 2008-02-26 |
| CA2349829A1 (en) | 2001-12-08 |
| US20020026049A1 (en) | 2002-02-28 |
| ES2194584B1 (es) | 2005-03-16 |
| US6969733B2 (en) | 2005-11-29 |
| BR0102319A (pt) | 2002-05-28 |
| US7026017B2 (en) | 2006-04-11 |
| US6737549B2 (en) | 2004-05-18 |
| FR2810041A1 (fr) | 2001-12-14 |
| GB2365430A (en) | 2002-02-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RE | Patent lapsed |
Effective date: 20130630 |