JP2003522227A - シリコン含有化合物 - Google Patents
シリコン含有化合物Info
- Publication number
- JP2003522227A JP2003522227A JP2001557879A JP2001557879A JP2003522227A JP 2003522227 A JP2003522227 A JP 2003522227A JP 2001557879 A JP2001557879 A JP 2001557879A JP 2001557879 A JP2001557879 A JP 2001557879A JP 2003522227 A JP2003522227 A JP 2003522227A
- Authority
- JP
- Japan
- Prior art keywords
- group
- groups
- alkyl
- aryl
- alkenyl
- 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.)
- Pending
Links
- 239000002210 silicon-based material Substances 0.000 title 1
- -1 cycloalkynyl Chemical group 0.000 claims abstract description 126
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 93
- 125000003118 aryl group Chemical group 0.000 claims abstract description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 61
- 239000001257 hydrogen Substances 0.000 claims abstract description 61
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 57
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 47
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 45
- 125000005375 organosiloxane group Chemical group 0.000 claims abstract description 43
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 39
- 239000000203 mixture Substances 0.000 claims abstract description 39
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 36
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 29
- 229920000642 polymer Polymers 0.000 claims abstract description 27
- 150000001282 organosilanes Chemical class 0.000 claims abstract description 26
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 25
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 25
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 25
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims abstract description 23
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 23
- 125000004171 alkoxy aryl group Chemical group 0.000 claims abstract description 22
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract description 22
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims abstract description 18
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 17
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 17
- 239000010703 silicon Substances 0.000 claims abstract description 17
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 16
- 125000003106 haloaryl group Chemical group 0.000 claims abstract description 16
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 15
- 125000005128 aryl amino alkyl group Chemical group 0.000 claims abstract description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 11
- 238000000576 coating method Methods 0.000 claims abstract description 11
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims abstract description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 10
- 230000008569 process Effects 0.000 claims abstract description 9
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract description 8
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 7
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims abstract description 7
- 125000006575 electron-withdrawing group Chemical group 0.000 claims abstract description 7
- 125000005020 hydroxyalkenyl group Chemical group 0.000 claims abstract description 7
- 150000004714 phosphonium salts Chemical class 0.000 claims abstract description 7
- 125000001174 sulfone group Chemical group 0.000 claims abstract description 7
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims abstract description 7
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 5
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims abstract description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 5
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims abstract description 5
- 125000005016 hydroxyalkynyl group Chemical group 0.000 claims abstract description 5
- 125000005027 hydroxyaryl group Chemical group 0.000 claims abstract description 5
- 125000002560 nitrile group Chemical group 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 60
- 238000006243 chemical reaction Methods 0.000 claims description 53
- 239000000126 substance Substances 0.000 claims description 40
- 239000012948 isocyanate Substances 0.000 claims description 39
- 150000002513 isocyanates Chemical class 0.000 claims description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 239000003153 chemical reaction reagent Substances 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 20
- 125000003277 amino group Chemical group 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 17
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 16
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 150000003254 radicals Chemical class 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- 125000000524 functional group Chemical group 0.000 claims description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 7
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000011248 coating agent Substances 0.000 claims description 7
- 125000005442 diisocyanate group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 238000007334 copolymerization reaction Methods 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 5
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 claims description 5
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 125000000962 organic group Chemical group 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical group ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000005429 oxyalkyl group Chemical group 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- BMJZXPSSNRVNBU-UHFFFAOYSA-N oxiran-2-ylmethyl 2-methylprop-2-eneperoxoate Chemical group CC(=C)C(=O)OOCC1CO1 BMJZXPSSNRVNBU-UHFFFAOYSA-N 0.000 claims description 3
- 238000010526 radical polymerization reaction Methods 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 150000003512 tertiary amines Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000005452 alkenyloxyalkyl group Chemical group 0.000 claims description 2
- 150000001345 alkine derivatives Chemical class 0.000 claims description 2
- 125000005256 alkoxyacyl group Chemical group 0.000 claims description 2
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 2
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 claims 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N Butanol Natural products CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- 125000002431 aminoalkoxy group Chemical group 0.000 claims 1
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N tert-butyl alcohol Substances CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 abstract description 4
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 abstract description 4
- 229910000077 silane Inorganic materials 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 25
- 239000000178 monomer Substances 0.000 description 22
- 150000001412 amines Chemical class 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000007792 addition Methods 0.000 description 14
- 150000003335 secondary amines Chemical class 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 150000003141 primary amines Chemical class 0.000 description 12
- 230000035699 permeability Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 9
- 238000006845 Michael addition reaction Methods 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 230000002209 hydrophobic effect Effects 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000004205 dimethyl polysiloxane Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 7
- 229920001296 polysiloxane Polymers 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910018540 Si C Inorganic materials 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229910010271 silicon carbide Inorganic materials 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 5
- BEWCNXNIQCLWHP-UHFFFAOYSA-N 2-(tert-butylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(C)(C)C BEWCNXNIQCLWHP-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 239000000017 hydrogel Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000004971 Cross linker Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000004386 diacrylate group Chemical group 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 150000003904 phospholipids Chemical class 0.000 description 4
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003158 alcohol group Chemical group 0.000 description 3
- 239000003125 aqueous solvent Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 230000008034 disappearance Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000007306 functionalization reaction Methods 0.000 description 3
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- 238000007039 two-step reaction Methods 0.000 description 3
- PSBDWGZCVUAZQS-UHFFFAOYSA-N (dimethylsulfonio)acetate Chemical compound C[S+](C)CC([O-])=O PSBDWGZCVUAZQS-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- 102100033007 Carbonic anhydrase 14 Human genes 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- 101000867862 Homo sapiens Carbonic anhydrase 14 Proteins 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical group C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 125000005024 alkenyl aryl group Chemical group 0.000 description 2
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 125000005001 aminoaryl group Chemical group 0.000 description 2
- 229960003237 betaine Drugs 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 2
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- OSDBJMYIUDLIRI-UHFFFAOYSA-N oxo-[[1-[[4-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methoxy]cyclohexyl]oxymethyl]pyridin-4-ylidene]methyl]azanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1COC1CCC(OCN2C=CC(=C[NH+]=O)C=C2)CC1 OSDBJMYIUDLIRI-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 2
- 125000005353 silylalkyl group Chemical group 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 125000005389 trialkylsiloxy group Chemical group 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- MGFZNUUZUVWOTG-UHFFFAOYSA-N (3-amino-3-oxoprop-1-en-2-yl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(=C)C(N)=O MGFZNUUZUVWOTG-UHFFFAOYSA-N 0.000 description 1
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 1
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- CUJPFPXNDSIBPG-UHFFFAOYSA-N 1,3-propanediyl Chemical group [CH2]C[CH2] CUJPFPXNDSIBPG-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/392—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/395—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing phosphorus
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/14—Layer or component removable to expose adhesive
- Y10T428/1452—Polymer derived only from ethylenically unsaturated monomer
- Y10T428/1457—Silicon
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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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/249921—Web or sheet containing structurally defined element or component
- Y10T428/249953—Composite having voids in a component [e.g., porous, cellular, etc.]
- Y10T428/249967—Inorganic matrix in void-containing component
- Y10T428/249969—Of silicon-containing material [e.g., glass, etc.]
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Silicon Polymers (AREA)
- Polyurethanes Or Polyureas (AREA)
- Eyeglasses (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00300942 | 2000-02-07 | ||
| EP00300942.0 | 2000-02-07 | ||
| PCT/GB2001/000519 WO2001057048A1 (en) | 2000-02-07 | 2001-02-07 | Silicon containing compounds from michael - type addition reactions useful as monomers and macromers |
Publications (2)
| Publication Number | Publication Date |
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| JP2003522227A true JP2003522227A (ja) | 2003-07-22 |
| JP2003522227A5 JP2003522227A5 (enExample) | 2012-06-28 |
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|---|---|---|---|
| JP2001557879A Pending JP2003522227A (ja) | 2000-02-07 | 2001-02-07 | シリコン含有化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7064174B2 (enExample) |
| EP (1) | EP1255761B1 (enExample) |
| JP (1) | JP2003522227A (enExample) |
| AT (1) | ATE303391T1 (enExample) |
| AU (1) | AU3383901A (enExample) |
| DE (1) | DE60113066T2 (enExample) |
| WO (1) | WO2001057048A1 (enExample) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004500458A (ja) * | 2000-02-07 | 2004-01-08 | バイオコンパティブルズ ユーケー リミテッド | モノマー及びマクロマーとして有用なマイケル型反応からの化合物を含む両性イオン基 |
| JP2014533314A (ja) * | 2011-11-10 | 2014-12-11 | ヴァーテラス・スペシャリティーズ・インコーポレーテッドＲｅｉｌｌｙ Ｉｎｄｕｓｔｒｉｅｓ，Ｉｎｃ． | 重合可能な材料 |
| WO2019107322A1 (ja) * | 2017-11-28 | 2019-06-06 | 三井化学株式会社 | （メタ）アクリレート、モノマー組成物、該組成物から得られた歯科材料およびその製造方法 |
| WO2023033012A1 (ja) * | 2021-08-31 | 2023-03-09 | 日油株式会社 | ホスホリルコリン基と水酸基を有するポリジメチルシロキサン含有モノマー |
| WO2023033013A1 (ja) * | 2021-08-31 | 2023-03-09 | 日油株式会社 | ホスホリルコリン基と水酸基を有するポリジメチルシロキサン含有モノマー |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4245336B2 (ja) * | 2002-11-25 | 2009-03-25 | 株式会社資生堂 | ホスホリルコリン基を有するポリシロキサン及びその製造方法 |
| CN100549018C (zh) * | 2003-12-02 | 2009-10-14 | 株式会社资生堂 | 含有磷酸胆碱基的化合物及包含该化合物的表面改性剂 |
| US7572841B2 (en) | 2006-06-15 | 2009-08-11 | Coopervision International Holding Company, Lp | Wettable silicone hydrogel contact lenses and related compositions and methods |
| US7540609B2 (en) | 2006-06-15 | 2009-06-02 | Coopervision International Holding Company, Lp | Wettable silicone hydrogel contact lenses and related compositions and methods |
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- 2001-02-07 EP EP01905867A patent/EP1255761B1/en not_active Expired - Lifetime
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004500458A (ja) * | 2000-02-07 | 2004-01-08 | バイオコンパティブルズ ユーケー リミテッド | モノマー及びマクロマーとして有用なマイケル型反応からの化合物を含む両性イオン基 |
| JP2014533314A (ja) * | 2011-11-10 | 2014-12-11 | ヴァーテラス・スペシャリティーズ・インコーポレーテッドＲｅｉｌｌｙ Ｉｎｄｕｓｔｒｉｅｓ，Ｉｎｃ． | 重合可能な材料 |
| WO2019107322A1 (ja) * | 2017-11-28 | 2019-06-06 | 三井化学株式会社 | （メタ）アクリレート、モノマー組成物、該組成物から得られた歯科材料およびその製造方法 |
| US11407846B2 (en) | 2017-11-28 | 2022-08-09 | Mitsui Chemicals, Inc. | (Meth)acrylate, monomer composition, dental material obtained from composition, and production method thereof |
| WO2023033012A1 (ja) * | 2021-08-31 | 2023-03-09 | 日油株式会社 | ホスホリルコリン基と水酸基を有するポリジメチルシロキサン含有モノマー |
| WO2023033013A1 (ja) * | 2021-08-31 | 2023-03-09 | 日油株式会社 | ホスホリルコリン基と水酸基を有するポリジメチルシロキサン含有モノマー |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1255761A1 (en) | 2002-11-13 |
| WO2001057048A8 (en) | 2001-11-15 |
| AU3383901A (en) | 2001-08-14 |
| WO2001057048A1 (en) | 2001-08-09 |
| DE60113066T2 (de) | 2006-06-14 |
| US7064174B2 (en) | 2006-06-20 |
| DE60113066D1 (de) | 2005-10-06 |
| ATE303391T1 (de) | 2005-09-15 |
| EP1255761B1 (en) | 2005-08-31 |
| US20030152786A1 (en) | 2003-08-14 |
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