JP5784131B2 - ペンダント親水性基を持つ重合しうる鎖延長ポリシロキサン - Google Patents
ペンダント親水性基を持つ重合しうる鎖延長ポリシロキサン Download PDFInfo
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- JP5784131B2 JP5784131B2 JP2013532900A JP2013532900A JP5784131B2 JP 5784131 B2 JP5784131 B2 JP 5784131B2 JP 2013532900 A JP2013532900 A JP 2013532900A JP 2013532900 A JP2013532900 A JP 2013532900A JP 5784131 B2 JP5784131 B2 JP 5784131B2
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- Prior art keywords
- acid
- meth
- bis
- group
- terminated polydimethylsiloxane
- Prior art date
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- -1 polysiloxane Polymers 0.000 title claims description 304
- 229920001296 polysiloxane Polymers 0.000 title claims description 180
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 86
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 85
- 229920002554 vinyl polymer Polymers 0.000 claims description 84
- 235000013870 dimethyl polysiloxane Nutrition 0.000 claims description 83
- 239000000178 monomer Substances 0.000 claims description 78
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 75
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 67
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 54
- 239000004971 Cross linker Substances 0.000 claims description 53
- 239000000463 material Substances 0.000 claims description 52
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 40
- 239000003431 cross linking reagent Substances 0.000 claims description 38
- 125000000524 functional group Chemical group 0.000 claims description 38
- 239000000017 hydrogel Substances 0.000 claims description 30
- 239000004593 Epoxy Substances 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 26
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 24
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 20
- 125000002947 alkylene group Chemical group 0.000 claims description 17
- 125000003277 amino group Chemical group 0.000 claims description 17
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 238000005859 coupling reaction Methods 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 10
- 238000006596 Alder-ene reaction Methods 0.000 claims description 10
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 10
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 238000006845 Michael addition reaction Methods 0.000 claims description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 9
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 claims description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 8
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 6
- MVBJSQCJPSRKSW-UHFFFAOYSA-N n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]prop-2-enamide Chemical compound OCC(CO)(CO)NC(=O)C=C MVBJSQCJPSRKSW-UHFFFAOYSA-N 0.000 claims description 6
- XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 claims description 5
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 claims description 5
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 5
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 5
- ONPJWQSDZCGSQM-UHFFFAOYSA-N 2-phenylprop-2-enoic acid Chemical compound OC(=O)C(=C)C1=CC=CC=C1 ONPJWQSDZCGSQM-UHFFFAOYSA-N 0.000 claims description 5
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 claims description 5
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229940091181 aconitic acid Drugs 0.000 claims description 5
- 229930016911 cinnamic acid Natural products 0.000 claims description 5
- 235000013985 cinnamic acid Nutrition 0.000 claims description 5
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 claims description 5
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 claims description 5
- 229940018557 citraconic acid Drugs 0.000 claims description 5
- 150000002009 diols Chemical class 0.000 claims description 5
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 claims description 5
- 238000007306 functionalization reaction Methods 0.000 claims description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 5
- 239000011976 maleic acid Substances 0.000 claims description 5
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 claims description 5
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 5
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 5
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 claims description 5
- 239000004334 sorbic acid Substances 0.000 claims description 5
- 235000010199 sorbic acid Nutrition 0.000 claims description 5
- 229940075582 sorbic acid Drugs 0.000 claims description 5
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 claims description 5
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 4
- UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- UIERETOOQGIECD-ARJAWSKDSA-N angelic acid Chemical compound C\C=C(\C)C(O)=O UIERETOOQGIECD-ARJAWSKDSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 239000001530 fumaric acid Substances 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
- IZFHEQBZOYJLPK-SSDOTTSWSA-N (R)-dihydrolipoic acid Chemical compound OC(=O)CCCC[C@@H](S)CCS IZFHEQBZOYJLPK-SSDOTTSWSA-N 0.000 claims description 3
- SCBKKGZZWVHHOC-UHFFFAOYSA-N 2,2-bis(sulfanyl)propanoic acid Chemical compound CC(S)(S)C(O)=O SCBKKGZZWVHHOC-UHFFFAOYSA-N 0.000 claims description 3
- WQABCVAJNWAXTE-UHFFFAOYSA-N dimercaprol Chemical compound OCC(S)CS WQABCVAJNWAXTE-UHFFFAOYSA-N 0.000 claims description 3
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- ACTRVOBWPAIOHC-UHFFFAOYSA-N succimer Chemical compound OC(=O)C(S)C(S)C(O)=O ACTRVOBWPAIOHC-UHFFFAOYSA-N 0.000 claims description 3
- RJVNRQLOTPARGS-UHFFFAOYSA-N 1,1-bis(sulfanyl)butan-1-ol Chemical compound CCCC(O)(S)S RJVNRQLOTPARGS-UHFFFAOYSA-N 0.000 claims description 2
- HZHABJYSBNZYFM-UHFFFAOYSA-N 1,1-bis(sulfanyl)pentan-1-ol Chemical compound CCCCC(O)(S)S HZHABJYSBNZYFM-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 229960001051 dimercaprol Drugs 0.000 claims description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical class F* 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims 2
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims 2
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 claims 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-M crotonate Chemical compound C\C=C\C([O-])=O LDHQCZJRKDOVOX-NSCUHMNNSA-M 0.000 claims 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 52
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 47
- 239000001301 oxygen Substances 0.000 description 47
- 229910052760 oxygen Inorganic materials 0.000 description 47
- 239000000243 solution Substances 0.000 description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
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- 238000000034 method Methods 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 12
- 239000006096 absorbing agent Substances 0.000 description 12
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- IEJPPSMHUUQABK-UHFFFAOYSA-N 2,4-diphenyl-4h-1,3-oxazol-5-one Chemical group O=C1OC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1 IEJPPSMHUUQABK-UHFFFAOYSA-N 0.000 description 11
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 8
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- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical group C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 8
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- PCGDBWLKAYKBTN-UHFFFAOYSA-N 1,2-dithiole Chemical compound C1SSC=C1 PCGDBWLKAYKBTN-UHFFFAOYSA-N 0.000 description 3
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- 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
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Description
近年、ソフトシリコーンヒドロゲルコンタクトレンズは、その高い酸素透過度及び快適さのために、ますます人気が高まっている。「ソフト」コンタクトレンズは、眼の形状にぴったり合わせることができるため、酸素は容易にレンズを迂回できない。角膜は他の組織のように血液から酸素を供給されないため、ソフトコンタクトレンズは、周りの空気(即ち、酸素)から酸素を角膜に到達させなければならない。充分な酸素が角膜に到達しなければ、角膜腫脹が起こる。長期間の酸素欠乏は、角膜における血管の不適切な増殖を招く。高い酸素透過度を持つことにより、シリコーンヒドロゲルコンタクトレンズは、充分な酸素をレンズ経由で角膜に透過させるため、角膜の健康に及ぼす有害な作用は最小限に抑えられる。
本発明は、1つの態様において、線形の化学線で重合しうる鎖延長ポリシロキサン架橋剤を提供する。本発明の鎖延長ポリシロキサン架橋剤は、(1)少なくとも2個のポリシロキサンセグメント;(2)各対のポリシロキサンセグメントの間の1個の二価有機基(ここで、各二価有機基は、少なくとも2個のペンダント親水性基及び/又は鎖を包含する);及び(3)2個の化学線で重合しうる末端基を含む。
特に断りない限り、本明細書に使用される全ての技術及び科学用語は、本発明が属する分野における当業者が共通に理解する意味と同じ意味を有する。一般に、本明細書に使用される命名法及び実験手順は、当該分野において周知であり共通に利用される。当該分野及び種々の一般文献に提供される方法のような、従来法がこれらの手順のために使用される。ある用語が単数形で提供される場合、本発明者らは、その用語の複数形も考えに入れる。本明細書に使用される命名法及び後述の実験手順は、当該分野において周知であり共通に利用される。
[式中、R1、R2、R3、R4、R5、R6、R7、及びR8は、相互に独立に、C1−C10アルキル、ジ−C1−C3アルキルアミノアルキル、C1−C10ヒドロキシアルキル、C1−C10エーテル、C1−C4アルキル−又はC1−C4アルコキシ−置換フェニル、C1−C10フルオロアルキル、C1−C10フルオロエーテル、C6−C18アリール基、シアノ(C1−C12アルキル)、−alk−(OCH2CH2)n−OR9(ここで、alkは、C1−C6−アルキレン二価基であり、R9は、水素又はC1−C5アルキルであり、そしてnは、1〜20の整数である)であり、m及びpは、相互に独立に、0〜150の整数であり、かつ(m+p)は、1〜150である]で示される二価基のことをいう。
D = −n’/(A × dc/dx)
[式中、n’=イオン輸送の速度[mol/分];A=曝露されたレンズの面積[mm2];dc=濃度差[mol/L];dx=レンズの厚さ[mm]]のとおり、フィックの法則を適用することにより求める。
(式中、A1及びA2は、相互に独立に、直接結合、直鎖若しくは分岐のC1−C10アルキレン二価基、−(CH(R”)CH2O)r3−CH(R”)CH2−(ここで、R”は、H又はメチルであり、そしてr3は、1〜20の整数である)又はC1−C7アルキレンオキシC1−C7アルキレン二価基であり、そしてR1、R2、R3、R4、R5、R6、R7、及びR8は、相互に独立に、C1−C8−アルキル、C1−C4−アルキル−若しくはC1−C4−アルコキシ−置換フェニル、フルオロ(C1−C18−アルキル)、−alk−(OCH2CH2)n−OR9(ここで、alkは、C1−C6−アルキレン二価基であり、R9は、C1−C6−アルキルであり、そしてnは、1〜20の整数である)であり、m及びpは、相互に独立に、0〜150の整数であり、かつ(m+p)は、1〜150である)で示される二価基であり;
G1、G2、G3、G4、G5、及びG6は、相互に独立に、直接結合又は式(III):
で示される二価基であり;
X1、X2、及びX3は、相互に独立に、直接結合、−O−、−NR’−、−S−、−C(O)−NR’−、−NR”−C(O)−、−O−C(O)−NH−、−C(O)−O−、−O−C(O)−、−NH−C(O)−O−、−NR’−C(O)−NH−、及び−NH−C(O)−NR’−(ここで、R’は、H又はC1−C8アルキルである)よりなる群から選択される結合であり;
r1、r2、q1、q2、q3、及びq4は、相互に独立に、0又は1の整数であり;
Y1及びY2は、相互に独立に、直接結合、−O−又は−NR’−(ここで、R’は、上記と同義である)であり;
Z1、Z2、Z3、Z4、Z5、Z6、及びBGは、相互に独立に、直接結合、直鎖若しくは分岐のC1−C12アルキレン二価基、少なくとも1個のヒドロキシル若しくはカルボキシル基若しくは−OC(O)(CH2)t1COOH(ここで、t1は、2〜4の整数である)を有する直鎖若しくは分岐のC3−C7アルキレン二価基、C1−C7アルキレンオキシC1−C7アルキレン二価基、−[CH2CH(T)CH2O]r4−[CH(R”)CH2O]r3−[CH2CH(T)CH2]r5−の二価基(ここで、R”及びr3は、上記と同義であり、Tは、ヒドロキシル又はカルボキシル基又は−OC(O)(CH2)tCOOH(ここで、tは、上記と同義である)であり、そしてr4及びr5は、相互に独立に、0又は1である)、非置換フェニレン二価基、C1−C4アルキル若しくはC1−C4アルコキシ置換フェニレン二価基若しくはC7−C12アラルキレン二価基、C5−C45脂環式若しくは脂肪族−脂環式二価基、C6−C24芳香族若しくは芳香脂肪族(araliphatic)二価基、又はこれらの組合せであり;
R10、R11、R12、R13、R14、R15、R16、R17、R18、及びR19は、相互に独立に、水素又はC1−C4アルキルであるが;ただし
BG及び/又はG2、G3、G4、及びG5の少なくとも1個のいずれかは、少なくとも1個のヒドロキシル若しくはカルボキシル基又は少なくとも1個の−OC(O)(CH2)t1COOH(ここで、t1は、上記と同義である)の基を含む]により定義される。
[式中、R20及びR21は、相互に独立に、水素又はメチルであり;A1及びA2は、相互に独立に、直接結合、直鎖若しくは分岐のC1−C10アルキレン二価基、−(CH(R”)CH2O)r3−CH(R”)CH2−(ここで、R”は、H又はメチルであり、そしてr3は、1〜20の整数である)、又はC1−C7アルキレンオキシC1−C7アルキレン二価基であり;mは、1〜150の整数であり;X4、X4’、X5、X5’、X6、及びX6’は、相互に独立に、直接結合、−O−、−NR’−、−S−、−C(O)−NR’−、−NR”−C(O)−、−O−C(O)−NH−、−NH−C(O)−O−、−NR’−C(O)−NH−、−NH−C(O)−NR’−、−C(O)−O−、及び−O−C(O)−(ここで、R’は、H又はC1−C8アルキルである)よりなる群から選択される結合であり;Z7、Z7’、Z8、Z8’、Z9、及びZ9’は、相互に独立に、直接結合、直鎖若しくは分岐のC1−C12アルキレン二価基、少なくとも1個のヒドロキシル若しくは−OC(O)(CH2)t1COOH(ここで、t1は、2〜4の整数である)を有する直鎖若しくは分岐のC3−C7アルキレン二価基、C1−C7アルキレンオキシC1−C7アルキレン二価基、−[CH2CH(T)CH2O]r4−[CH(R”)CH2O]r3−[CH2CH(T)CH2]r5−の二価基(ここで、R”及びr3は、上記と同義であり、Tは、ヒドロキシル又は−OC(O)(CH2)tCOOH(ここで、tは、上記と同義である)であり、そしてr4及びr5は、相互に独立に、0又は1である)、非置換フェニレン二価基、C1−C4アルキル若しくはC1−C4アルコキシ置換フェニレン二価基若しくはC7−C12アラルキレン二価基、C5−C45脂環式若しくは脂肪族−脂環式二価基、C6−C24芳香族若しくは芳香脂肪族二価基、又はこれらの組合せである]により定義される。
酸素透過度測定
レンズの見かけの酸素透過度及びレンズ材料の酸素伝達率は、米国特許第5,760,100号及びWintertonら(The Cornea: Transactions of the World Congress on the Cornea 111 , H. D. Cavanagh Ed., Raven Press: New York 1988, pp273-280)の論文に記載されるもの(これらは両方ともその全体が引用例として本明細書に取り込まれる)と同様の手法により測定する。酸素フラックス(J)は、Dk1000装置(Applied Design and Development Co., Norcross, GAから入手できる)、又は同様の分析装置を用いて、ウェットセル(即ち、ガス流が約100%相対湿度に維持される)中で34℃で測定する。既知の百分率の酸素(例えば、21%)を有する空気流は、約10〜20cm3/分の速度でレンズの片側を通過させ、一方、窒素流は、約10〜20cm3/分の速度でレンズの反対側に通す。試料は、試験媒体(即ち、生理食塩水又は蒸留水)中で所定の試験温度で測定前に少なくとも30分間(しかし45分間を超えない)平衡化させる。被覆層として使用される任意の試験媒体は、所定の試験温度で測定前に少なくとも30分間(しかし45分間を超えない)平衡化させる。撹拌モーターの速度は、ステッピングモーター制御器での400±15の表示設定に対応する、1200±50rpmにセットする。系を囲む気圧、P測定値を測定する。試験用に曝露される領域におけるレンズの厚さ(t)は、MitotoyaマイクロメーターVL-50、又は同様の装置で約10箇所を測定し、そして測定値を平均することにより求める。窒素流中の酸素濃度(即ち、レンズを通じて拡散する酸素)は、DK1000装置を用いて測定する。レンズ材料の見かけの酸素透過度、Dkappは、下記式から求める:
Dkapp=Jt/(P酸素)
(式中、
J=酸素フラックス[マイクロリットルO2/cm2−分]
P酸素=(P測定値−P水蒸気)=(空気流中O2%)[mmHg]=空気流中の酸素の分圧
P測定値=気圧(mmHg)
P水蒸気=34℃で0mmHg(ドライセル中)(mmHg)
P水蒸気=34℃で40mmHg(ウェットセル中)(mmHg)
t=曝露される試験領域におけるレンズの平均厚さ(mm)
Dkappは、barrerの単位で表される)。
式中、tは測定下の対照レンズの厚さであり、そしてnは測定した対照レンズの数である。残存酸素抵抗値Rrをtデータに対してプロットして、式:Y=a+bX(ここで、j番目のレンズでは、Yj=(ΔP/J)jであり、そしてX=tjである)の曲線に当てはめる。残存酸素抵抗、Rrは、aに等しい。
Dkc = t/[(t/Dka)−Rr] (2)
Dka_std = tstd/[(tstd/Dkc)+Rr_std] (3)
OH基を持つCE−PDMS(CE−PDMS−(OH)x)の合成
ペンダントヒドロキシル基を持つ鎖延長ポリジメチルシロキサン架橋剤は、以下の反応スキームにより調製する。
COOH基を持つCEPDMS(CE−PDMS−(COOH)y)の合成
ペンダントカルボキシル基を持つ鎖延長ポリジメチルシロキサン架橋剤は、以下の反応スキームにより調製する。
ペンダントジェファーミン(Jeffamine)鎖を持つ親水性PDMS
ペンダントポリエチレングリコール−ポリプロピレングリコールブロックコポリマー鎖を持つ鎖延長ポリジメチルシロキサン架橋剤は、以下の反応スキームにより調製する。
ペンダントジェファーミン及びアルキル鎖を持つ親水性PDMS(実施例D)
250ml丸底フラスコに、実施例3で調製したPDMS−(COOH)y 5.9g((≒)4.52meqのCOOH)、NHS 0.88gを加え、続いてジクロロメタン50g及びTHF 5mLの混合物を加える。この溶液を充分に撹拌する。氷浴を用いて溶液を冷却後、ジクロロメタン5mL中のDCC 1.58g(7.66meq)を加える。反応は0℃で約5分間実施して、氷浴なしで約2時間続ける。1μm孔径の濾紙により溶液を氷浴中の250mL丸底フラスコに濾過した後、ジクロロメタン10g中のモノ−アミン、モノ−メチル末端ポリエチレングリコール−ポリプロピレングリコールブロックコポリマー、ジェファーミン2070(5.1g、2.55meq)及び1−ドデシルアミン(0.95g、5.11meq)の溶液を添加ロートを介して1時間以内に滴下により加える。反応は室温で約20時間続ける。溶媒の大部分を除去後、溶液を希釈するためにメタノール80mLを加える。この希釈溶液を次に透析管(MWCO、3,500ダルトン)に移して、溶媒を3回交換しながらメタノール2L中で2日間透析に付す。透析管中の溶液を250ml丸底フラスコに移して、ロータリーエバポレーター(rota-vap)を介して35℃で溶媒を除去し、そして高真空(25℃で5mbar)により残留溶媒の更なる除去を達成する。48%の収率で最終生成物5.7gを得る。
ペンダントジェファーミン及びフッ素化アルキル鎖を持つ親水性PDMS
250ml丸底フラスコに、実施例3で調製したPDMS−(COOH)y 10g((≒)7.66meqのCOOH)、NHS 0.88gを加え、続いてジクロロメタン50g及びTHF 5mLの混合物を加える。この溶液を充分に撹拌する。氷浴を用いて溶液を冷却後、ジクロロメタン5mL中のDCC 1.58g(7.66meq)を加える。反応は0℃で約5分間実施して、氷浴なしで2時間続ける。1μm孔径の濾紙により溶液を氷浴中の250mL丸底フラスコに濾過した後、ジクロロメタン10g中のジェファーミン2070(5.1g、2.55meq)及び2,2,2−トリフルオロエチルアミン(0.46g、5.11meq)の溶液を添加ロートを介して1時間以内に滴下により加える。反応は室温で約20時間続ける。溶媒の大部分を除去後、溶液を希釈するためにメタノール80mLを加える。この希釈溶液を次に透析管(MWCO、3,500ダルトン)に移して、溶媒を3回交換しながらメタノール2L中で2日間透析に付す。透析管中の溶液を250ml丸底フラスコに移して、ロータリーエバポレーター(rota-vap)を介して35℃で溶媒を除去し、そして高真空(25℃で5mbar)により残留溶媒の更なる除去を達成する。81%の収率で最終生成物12.6gを得る。最終ポリマー中の二重結合含量は0.1233meq/gである。
レンズ配合物及びレンズ注型
以下の表に示す組成を持つ種々のレンズ配合物を調製する。混合物の均質化は、一晩のローラーでの回転により達成する。レンズ配合物は、UV光(5.8mW/cm2)下でポリプロピレンプラスチック成形用型に5分間入れる。成形用型からレンズを取り出した後、コンタクトレンズをメチルエチルケトンで約5分間抽出し、続いてDI水で約5分間抽出する。レンズをガラスバイアル中のPBSに保存して、120℃で30分間オートクレーブにかける。
注記:DMA:N,N−ジメチルアクリルアミド;MBA:メチレンビスアクリルアミド;BA:アクリル酸ブチル;Tris:トリス(トリメチルシロキシ)プロピルアクリルアミド;DC-1173:Darocur 1173;WBUT:レンズをPBS生理食塩水から取り出してから水膜が壊れるまでの間の水ブレイクアップ時間;WBUT=0++:レンズ周辺部にドライスポットがありレンズ中央部は湿潤なままである;WBUT=0+:レンズ周辺部にドライスポットがあり、レンズ表面上にドライスポットが散在し、そして表面の大部分は湿潤なままである;レンズの混濁の採点:0−透明、目に見える混濁なし、1−辛うじて目に見える、見るには本当に目を凝らす必要がある、2−わずかに目に見える、簡単には見えない、3−目に見える、簡単に見える、4−わずかに不透明、ほぼ白色(混濁)、及び5−不透明、まさに白色、透明でない。
Claims (10)
- 式(I):
[式中、
ν及びωは、相互に独立に、0〜20の整数であり(ただし、(ν+ω)は、1〜20の整数である)、
D1、D2及びD3は、相互に独立に、式(II):
(式中、A1及びA2は、相互に独立に、直接結合、直鎖若しくは分岐のC1−C10アルキレン二価基、−(CH(R”)CH2O)r3−CH(R”)CH2−(ここで、R”は、H又はメチルであり、そしてr3は、1〜20の整数である)又はC1−C7アルキレンオキシC1−C7アルキレン二価基であり、そしてR1、R2、R3、R4、R5、R6、R7、及びR8は、相互に独立に、C1−C8−アルキル、C1−C4−アルキル−若しくはC1−C4−アルコキシ−置換フェニル、フルオロ(C1−C18−アルキル)、−alk−(OCH2CH2)n−OR9(ここで、alkは、C1−C6−アルキレン二価基であり、R9は、C1−C6−アルキルであり、そしてnは、1〜20の整数である)であり、m及びpは、相互に独立に、0〜150の整数であり、かつ(m+p)は、1〜150である)で示される二価基であり;
G1、G2、G3、G4、G5、及びG6は、相互に独立に、直接結合又は式(III):
で示される二価基であり;
L1及びL2は、相互に独立に、式(IV):
で示される二価基であり;
X1、X2、及びX3は、相互に独立に、直接結合、−O−、−NR’−、−S−、−C(O)−NR’−、−NR”−C(O)−、−O−C(O)−NH−、−C(O)−O−、−O−C(O)−、−NH−C(O)−O−、−NR’−C(O)−NH−、及び−NH−C(O)−NR’−(ここで、R’は、H又はC1−C8アルキルである)よりなる群から選択される結合であり;
r1、r2、q1、q2、q3、及びq4は、相互に独立に、0又は1の整数であり;
Y1及びY2は、相互に独立に、直接結合、−O−又は−NR’−(ここで、R’は、上記と同義である)であり;
Z1、Z2、Z3、Z4、Z5及びZ6は、相互に独立に、直接結合、直鎖若しくは分岐のC1−C12アルキレン二価基、少なくとも1個のヒドロキシル若しくはカルボキシル基若しくは−OC(O)(CH2)t1COOH(ここで、t1は、2〜4の整数である)を有する直鎖若しくは分岐のC3−C7アルキレン二価基、C1−C7アルキレンオキシC1−C7アルキレン二価基、−[CH2CH(T)CH2O]r4−[CH(R”)CH2O]r3−[CH2CH(T)CH2]r5−の二価基(ここで、R”及びr3は、上記と同義であり、Tは、ヒドロキシル又はカルボキシル基であり、そしてr4及びr5は、相互に独立に、0又は1である)、非置換フェニレン二価基、C1−C4アルキル若しくはC1−C4アルコキシ置換フェニレン二価基若しくはC7−C12アラルキレン二価基、C5−C45脂環式若しくは脂肪族−脂環式二価基、C6−C24芳香族若しくは芳香脂肪族二価基、又はこれらの組合せであり;
R10、R11、R12、R13、R14、R15、R16、R17、R18、及びR19は、相互に独立に、水素又はC1−C4アルキルであり;
BGは、少なくとも1個のヒドロキシル若しくはカルボキシル基若しくは−OC(O)(CH2)t1COOH(ここで、t1は、2〜4の整数である)を有する直鎖若しくは分岐のC3−C7アルキレン二価基である]により表わされる鎖延長ポリシロキサン架橋剤。 - 鎖延長ポリシロキサン架橋剤が、少なくとも1種の式(2):
[式中、R20及びR21は、相互に独立に、水素又はメチルであり;A1及びA2は、相互に独立に、直接結合、直鎖若しくは分岐のC1−C10アルキレン二価基、−(CH(R”)CH2O)r3−CH(R”)CH2−(ここで、R”は、H又はメチルであり、そしてr3は、1〜20の整数である)、又はC1−C7アルキレンオキシC1−C7アルキレン二価基であり;mは、1〜350の整数であり;X4、X4’、X5、X5’、X6、及びX6’は、相互に独立に、直接結合、−O−、−NR’−、−S−、−C(O)−NR’−、−NR”−C(O)−、−O−C(O)−NH−、−NH−C(O)−O−、−NR’−C(O)−NH−、−NH−C(O)−NR’−、−C(O)−O−、及び−O−C(O)−(ここで、R’は、H又はC1−C8アルキルである)よりなる群から選択される結合であり、Z7、Z7’、Z8、Z8’、Z9、及びZ9’は、相互に独立に、直接結合、直鎖若しくは分岐のC1−C12アルキレン二価基、少なくとも1個のヒドロキシル若しくは−OC(O)(CH2)t1COOH(ここで、t1は、2〜4の整数である)を有する直鎖若しくは分岐のC3−C7アルキレン二価基、C1−C7アルキレンオキシC1−C7アルキレン二価基、−[CH2CH(T)CH2O]r4−[CH(R”)CH2O]r3−[CH2CH(T)CH2]r5−の二価基(ここで、R”及びr3は、上記と同義であり、Tは、ヒドロキシル又は−OC(O)(CH2)tCOOH(ここで、tは、上記と同義である)であり、そしてr4及びr5は、相互に独立に、0又は1である)、非置換フェニレン二価基、C1−C4アルキル若しくはC1−C4アルコキシ置換フェニレン二価基若しくはC7−C12アラルキレン二価基、C5−C45脂環式若しくは脂肪族−脂環式二価基、C6−C24芳香族若しくは芳香脂肪族二価基、又はこれらの組合せである]で示されるポリシロキサン架橋剤を少なくとも1種のジメルカプタンと、マイケル付加又はチオール−エン反応条件下で反応させることにより得られる、請求項1に記載の鎖延長ポリシロキサン架橋剤。 - 少なくとも1種のポリシロキサン架橋剤が、少なくとも1個のヒドロキシル基を含み、そして(1)ジ−エポキシ末端ポリシロキサン[(メタ)アクリル酸C2からC6のヒドロキシルアルキル、C2からC6のヒドロキシアルキル(メタ)アクリルアミド、アリルアルコール、アリルアミン、(メタ)アクリル酸アミノ−C2−C6アルキル、(メタ)アクリル酸C1−C6アルキルアミノ−C2−C6アルキル、ビニルアミン、アミノ−C2−C6アルキル(メタ)アクリルアミド、C1−C6アルキルアミノ−C2−C6アルキル(メタ)アクリルアミド、アクリル酸、C1−C4アルキルアクリル酸、N−[トリス(ヒドロキシメチル)メチル]アクリルアミド、N,N−2−アクリルアミドグリコール酸、β−メチル−アクリル酸(クロトン酸)、α−フェニルアクリル酸、β−アクリルオキシプロピオン酸、ソルビン酸、アンゲリカ酸、ケイ皮酸、1−カルボキシ−4−フェニル ブタジエン−1,3、イタコン酸、シトラコン酸、メサコン酸、グルタコン酸、アコニット酸、マレイン酸、フマル酸、及びこれらの組合せよりなる群から選択されるエチレン型官能基化ビニルモノマーの使用による];(2)ヒドロキシル基、アミノ基、カルボキシル基、及びこれらの組合せよりなる群から選択される2個の末端官能基を有するポリシロキサン[エポキシ含有ビニルモノマーの使用による];(3)ヒドロキシル基、アミノ基、カルボキシル基、及びこれらの組合せよりなる群から選択される2個の末端官能基を有するポリシロキサン[ジ−エポキシ化合物の存在下での、(メタ)アクリル酸C2からC6のヒドロキシルアルキル、C2からC6のヒドロキシアルキル(メタ)アクリルアミド、アリルアルコール、アリルアミン、(メタ)アクリル酸アミノ−C2−C6アルキル、(メタ)アクリル酸C1−C6アルキルアミノ−C2−C6アルキル、ビニルアミン、アミノ−C2−C6アルキル(メタ)アクリルアミド、C1−C6アルキルアミノ−C2−C6アルキル(メタ)アクリルアミド、アクリル酸、C1−C4アルキルアクリル酸、N−[トリス(ヒドロキシメチル)メチル]アクリルアミド、N,N−2−アクリルアミドグリコール酸、β−メチル−アクリル酸(クロトン酸)、α−フェニルアクリル酸、β−アクリルオキシプロピオン酸、ソルビン酸、アンゲリカ酸、ケイ皮酸、1−カルボキシ−4−フェニル ブタジエン−1,3、イタコン酸、シトラコン酸、メサコン酸、グルタコン酸、アコニット酸、マレイン酸、フマル酸、及びこれらの組合せよりなる群から選択されるエチレン型官能基化ビニルモノマーの使用による];(4)ジ−エポキシ末端ポリシロキサン[ジオール、ジ−アミン化合物、ジカルボン酸化合物、又はこれらの組合せの存在下での、(メタ)アクリル酸グリシジルの使用による];あるいは(5)これらの組合せ;のエチレン型官能基化により得られる、請求項2に記載の鎖延長ポリシロキサン架橋剤。
- 少なくとも1種のポリシロキサン架橋剤が、α,ω−ビス[3−(メタ)アクリルオキシ−2−ヒドロキシプロピルオキシプロピル]末端ポリジメチルシロキサン、α,ω−ビス[3−(メタ)アクリルオキシエトキシ−2−ヒドロキシプロピルオキシプロピル]末端ポリジメチルシロキサン、α,ω−ビス[3−(メタ)アクリルオキシエチルアミノ−2−ヒドロキシプロピルオキシプロピル]末端ポリジメチルシロキサン、α,ω−ビス[3−(メタ)アクリルアミドエトキシ−2−ヒドロキシプロピルオキシプロピル]末端ポリジメチルシロキサン、α,ω−ビス[(メタ)アクリルアミドエチルアミノ−2−ヒドロキシプロピルオキシプロピル]末端ポリジメチルシロキサン、α,ω−ビス[3−(メタ)アクリルオキシプロポキシ−2−ヒドロキシプロピルオキシプロピル]末端ポリジメチルシロキサン、α,ω−ビス[3−(メタ)アクリルオキシプロピルアミノ−2−ヒドロキシプロピルオキシプロピル]末端ポリジメチルシロキサン、α,ω−ビス[3−(メタ)アクリルアミドプロポキシ−2−ヒドロキシプロピルオキシプロピル]末端ポリジメチルシロキサン、α,ω−ビス[3−(メタ)アクリルアミドプロピルアミノ−2−ヒドロキシプロピルオキシプロピル]末端ポリジメチルシロキサン、α,ω−ビス[3−(メタ)アクリルアミドイソプロポキシ−2−ヒドロキシプロピルオキシプロピル]末端ポリジメチルシロキサン、α,ω−ビス(アリルオキシ−2−ヒドロキシプロピルオキシエトキシプロピル)末端ポリジメチルシロキサン、α,ω−ビス(アリルアミノ−2−ヒドロキシプロピルオキシプロピル)末端ポリジメチルシロキサン、α,ω−ビス(ビニルアミノ−2−ヒドロキシプロピルオキシプロピル)末端ポリジメチルシロキサン、α,ω−ビス(アリルオキシ−2−ヒドロキシプロピルオキシプロピル)末端ポリジメチルシロキサン、α,ω−ビス(ビニルオキシ−2−ヒドロキシプロピルオキシエトキシプロピル)末端ポリジメチルシロキサン、α,ω−ビス[(メタ)アクリルオキシ−2−ヒドロキシプロピルオキシエトキシプロピル]末端ポリジメチルシロキサン、α,ω−ビス[(メタ)アクリルオキシ−2−ヒドロキシプロピル−N−エチルアミノプロピル]末端ポリジメチルシロキサン、α,ω−ビス[(メタ)アクリルオキシ−2−ヒドロキシプロピルアミノプロピル]末端ポリジメチルシロキサン、α,ω−ビス[アリルオキシ−2−ヒドロキシプロピル−N−エチルアミノプロピル]末端ポリジメチルシロキサン、α,ω−ビス[ビニルオキシ−2−ヒドロキシプロピル−N−エチルアミノプロピル]末端ポリジメチルシロキサン、α,ω−ビス[(メタ)アクリルオキシ−2−ヒドロキシプロピルオキシカルボニルプロピル]末端ポリジメチルシロキサン、α,ω−ビス[アリルオキシ−2−ヒドロキシプロピルオキシカルボニルプロピル]末端ポリジメチルシロキサン、α,ω−ビス[ビニルオキシ−2−ヒドロキシプロピルオキシカルボニルプロピル]末端ポリジメチルシロキサン、α,ω−ビス[(メタ)アクリルオキシ−2−ヒドロキシプロピルオキシペンチルカルボニルオキシアルキル]末端ポリジメチルシロキサン、α,ω−ビス[アリルオキシ−2−ヒドロキシプロピルオキシペンチルカルボニルオキシアルキル]末端ポリジメチルシロキサン、α,ω−ビス[ビニルオキシ−2−ヒドロキシプロピルオキシペンチルカルボニルオキシアルキル]末端ポリジメチルシロキサン、α,ω−ビス(アリルオキシ−2−ヒドロキシプロピルオキシ(ポリエチレンオキシ)プロピル)末端ポリジメチルシロキサン、α,ω−ビス(ビニルオキシ−2−ヒドロキシプロピルオキシ(ポリエチレンオキシ)プロピル)末端ポリジメチルシロキサン、α,ω−ビス[(メタ)アクリルオキシ−2−ヒドロキシプロピルオキシ(ポリエチレンオキシ)プロピル]末端ポリジメチルシロキサン、カップリング生成物[(メタ)アクリル酸C2−C4ヒドロキシアルキル又はC2−C4ヒドロキシアルキル(メタ)アクリルアミド又は(メタ)アクリル酸と、α,ω−ビス(ヒドロキシエトキシプロピル)−ポリジメチルシロキサンとの、ジ−エポキシ化合物を介する]、又はこれらの組合せである、請求項2又は3に記載の鎖延長ポリシロキサン架橋剤。
- 少なくとも1種のジメルカプタンが、少なくとも1個のヒドロキシ及び/又はカルボキシル基を含む、請求項2、3又は4に記載の鎖延長ポリシロキサン架橋剤。
- 少なくとも1種のポリシロキサン架橋剤が、ヒドロキシ又はカルボキシル基を含まず、そして少なくとも1種のジメルカプタンが、少なくとも1個のヒドロキシ及び/又はカルボキシル基を含む、請求項2に記載の鎖延長ポリシロキサン架橋剤。
- 少なくとも1種のジメルカプタンが、ジメルカプロール、ジメルカプトブタノール、ジメルカプトペンタノール、ジチオスレイトール、ジメルカプトプロピオン酸、ジヒドロリポ酸、ジメルカプトコハク酸、又はこれらの組合せである、請求項6に記載の鎖延長ポリシロキサン架橋剤。
- 少なくとも1種のジメルカプタンが、少なくとも1個のカルボキシル基を含む、請求項6又は7に記載の鎖延長ポリシロキサン架橋剤。
- 少なくとも1種のジメルカプタンが、ジメルカプトプロピオン酸、ジヒドロリポ酸、ジメルカプトコハク酸、又はこれらの組合せである、請求項8に記載の鎖延長ポリシロキサン架橋剤。
- (a)請求項1〜9のいずれか1項に記載の鎖延長ポリシロキサン架橋剤を包含する、レンズ形成材料を、成形用型内で硬化することにより得られるシリコーンヒドロゲル材料を含む、眼用レンズ。
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