JPH03240021A - Contact lens material - Google Patents
Contact lens materialInfo
- Publication number
- JPH03240021A JPH03240021A JP3608890A JP3608890A JPH03240021A JP H03240021 A JPH03240021 A JP H03240021A JP 3608890 A JP3608890 A JP 3608890A JP 3608890 A JP3608890 A JP 3608890A JP H03240021 A JPH03240021 A JP H03240021A
- Authority
- JP
- Japan
- Prior art keywords
- monomer
- contact lens
- oxygen permeability
- bifunctional
- obtd
- 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
- 239000000463 material Substances 0.000 title claims abstract description 22
- 239000000178 monomer Substances 0.000 claims abstract description 45
- 229920001577 copolymer Polymers 0.000 claims abstract description 17
- 230000001588 bifunctional effect Effects 0.000 claims abstract description 9
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 4
- 125000005375 organosiloxane group Chemical group 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims 1
- -1 fluoroalkyl ester Chemical class 0.000 abstract description 23
- 230000035699 permeability Effects 0.000 abstract description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 18
- 239000001301 oxygen Substances 0.000 abstract description 18
- 229910052760 oxygen Inorganic materials 0.000 abstract description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 9
- 238000011109 contamination Methods 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 5
- 230000003287 optical effect Effects 0.000 abstract description 5
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract description 4
- 229920001971 elastomer Polymers 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract description 2
- 230000001846 repelling effect Effects 0.000 abstract 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 11
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 11
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 11
- 230000000704 physical effect Effects 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 238000005259 measurement Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 210000004087 cornea Anatomy 0.000 description 6
- 229920002379 silicone rubber Polymers 0.000 description 6
- 239000004945 silicone rubber Substances 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 5
- 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 4
- 239000012530 fluid Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- MNSWITGNWZSAMC-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl prop-2-enoate Chemical compound FC(F)(F)C(C(F)(F)F)OC(=O)C=C MNSWITGNWZSAMC-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- VBHXIMACZBQHPX-UHFFFAOYSA-N 2,2,2-trifluoroethyl prop-2-enoate Chemical compound FC(F)(F)COC(=O)C=C VBHXIMACZBQHPX-UHFFFAOYSA-N 0.000 description 2
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000005516 engineering process Methods 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
- 230000009477 glass transition Effects 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- LGYTZKPVOAIUKX-UHFFFAOYSA-N kebuzone Chemical compound O=C1C(CCC(=O)C)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 LGYTZKPVOAIUKX-UHFFFAOYSA-N 0.000 description 2
- 229960000194 kebuzone Drugs 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- DEQJNIVTRAWAMD-UHFFFAOYSA-N 1,1,2,4,4,4-hexafluorobutyl prop-2-enoate Chemical compound FC(F)(F)CC(F)C(F)(F)OC(=O)C=C DEQJNIVTRAWAMD-UHFFFAOYSA-N 0.000 description 1
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- JDVGNKIUXZQTFD-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropyl prop-2-enoate Chemical compound FC(F)(F)C(F)(F)COC(=O)C=C JDVGNKIUXZQTFD-UHFFFAOYSA-N 0.000 description 1
- PLXOUIVCSUBZIX-UHFFFAOYSA-N 2,2,3,3,4,4,4-heptafluorobutyl prop-2-enoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)COC(=O)C=C PLXOUIVCSUBZIX-UHFFFAOYSA-N 0.000 description 1
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-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
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical compound CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 108010000912 Egg Proteins Proteins 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-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
- 102000016943 Muramidase Human genes 0.000 description 1
- 108010014251 Muramidase Proteins 0.000 description 1
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 235000013345 egg yolk Nutrition 0.000 description 1
- 210000002969 egg yolk Anatomy 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- FFYWKOUKJFCBAM-UHFFFAOYSA-N ethenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC=C FFYWKOUKJFCBAM-UHFFFAOYSA-N 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
- 230000002349 favourable effect Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229960000274 lysozyme Drugs 0.000 description 1
- 235000010335 lysozyme Nutrition 0.000 description 1
- 239000004325 lysozyme Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- WFKDPJRCBCBQNT-UHFFFAOYSA-N n,2-dimethylprop-2-enamide Chemical compound CNC(=O)C(C)=C WFKDPJRCBCBQNT-UHFFFAOYSA-N 0.000 description 1
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 1
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Landscapes
- Eyeglasses (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、新規なコンタクトレンズ材料に関するもので
ある。更に詳しくいえば、本発明は酸素透過性及び光学
的、機械的特性に優れ、且つ良好な装用感を有し、角膜
への固着の恐れがない、実質的に非含水なソフトコンタ
クトレンズの材料に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a novel contact lens material. More specifically, the present invention provides a substantially water-free soft contact lens material that has excellent oxygen permeability, optical and mechanical properties, is comfortable to wear, and has no risk of sticking to the cornea. It is related to.
ソフトコンタクトレンズは含水性ソフトコンタクトレン
ズと非含水性ソフトコンタクトレンズに分けられる。Soft contact lenses are divided into hydrated soft contact lenses and non-hydrated soft contact lenses.
含水性ソフトコンタクトレンズは、柔らかく装用感が良
好で、高含水型になると酸素透過性が高くなる等の長所
を持っているが、破損しやすく、耐久性が劣ること、及
び涙液中の成分によって汚染されやすく細菌の繁殖の恐
れがある為、定期的に煮沸消毒をしなければならない等
、取扱い上、不便なことが多い。Water-containing soft contact lenses have the advantage of being soft and comfortable to wear, and higher water-containing types have higher oxygen permeability. It is often inconvenient to handle, such as having to periodically sterilize it by boiling, as it is easily contaminated by bacteria and there is a risk of bacterial growth.
非含水性コンタクトレンズとしては、例えば、分子鎖両
末端がビニルジメチルシリル基で封鎖されたポリジメチ
ルシロキサンとメチルハイドロジエンポリシロキサンと
の混合物に、白金系の触媒を加え、モールディング法で
加熱硬化させる方法で得られるシリコーンラバーレンズ
と両末端にメタクリロキシ基のような重合性基を付加し
たポリパーフルオロエーテルを主成分とした重合体から
なる、ソフトコンタクトレンズとハードコンタクトレン
ズとの中間の弾性率を有する可撓性レンズが知られてい
る。（特開昭５４−８１３６３号公報、特開昭５８−１
２７９１４号公報）
また（メタ）アクリル酸と（メタ）アクリル酸エステル
とを共重合させたハードな基体より、切削してレンズを
作成し、これをエステル化及び／又はエステル交換処理
を行い、装用感の良好な非含水性ソフトコンタクトレン
ズも製造されている。For non-hydroscopic contact lenses, for example, a platinum-based catalyst is added to a mixture of polydimethylsiloxane and methylhydrodiene polysiloxane in which both ends of the molecular chain are blocked with vinyldimethylsilyl groups, and the mixture is heated and cured by a molding method. A silicone rubber lens obtained by this method and a polymer mainly composed of polyperfluoroether with polymerizable groups such as methacryloxy groups added to both ends, which have an elastic modulus intermediate between soft and hard contact lenses. Flexible lenses are known. (Unexamined Japanese Patent Publication No. 54-81363, Unexamined Japanese Patent Publication No. 58-1
No. 27914) In addition, a hard substrate made by copolymerizing (meth)acrylic acid and (meth)acrylic acid ester is cut to create a lens, which is subjected to esterification and/or transesterification treatment, and then worn. Non-hydrous soft contact lenses with good feel are also manufactured.
（特開昭４８−７５０４７号公報）
これらの非含水性コンタクトレンズにも、それぞれ次の
ような問題点が見られる。(Japanese Unexamined Patent Publication No. 48-75047) These non-water-containing contact lenses also have the following problems.
まず、シリコーンラバーレンズについては、開発当初は
レンズ表面の疎水性を改善するために施した親水化処理
層が剥離したり、弾力性が大きすぎるために角膜への固
着が起こるなどの欠点があって、広く実用化されるまで
には到らなかったが、最近では表面親水化処理技術の進
歩、レンズデザインの変更、及び機械的性質の改良など
により、前記欠点はかなり改善されてはいるものの、ま
だ必ずしも十分に満足しうるものではなく、広（−般に
用いられるに到っていないのが実状である。First of all, when silicone rubber lenses were first developed, they had drawbacks such as the hydrophilic treatment layer applied to improve the hydrophobicity of the lens surface peeling off, and their excessive elasticity causing them to stick to the cornea. However, recent advances in surface hydrophilic treatment technology, changes in lens design, and improvements in mechanical properties have significantly improved the above drawbacks. However, the reality is that it is still not completely satisfactory and has not yet been widely used.
次に、ポリパーフルオロポリエーテルを主成分とした非
含水性レンズは、ソフトコンタクトレンズというよりも
セミハードタイプに近いため、とてもソフトコンタクト
レンズのような装用感が得られず、角膜上でのレンズの
動きも満足できるものでない。Next, non-hydrous lenses that are mainly composed of polyperfluoropolyether are more like semi-hard types than soft contact lenses, so they do not feel as comfortable when worn as soft contact lenses, and the lenses do not touch the cornea. The movement is also not satisfactory.
また（メタ）アクリル酸エステルを主体としたソフトコ
ンタクトレンズは、酸素透過性に劣る為、長時間の装用
には通していない。In addition, soft contact lenses made mainly of (meth)acrylic acid esters have poor oxygen permeability, so they cannot be worn for long periods of time.
多官能ポリシロキサンを主体とした酸素透過性の高いコ
ンタクトレンズ材料も特開昭５４−２４０４７号公報、
特開昭５６−５１７１５号公報に記載されているが、こ
れらの多官能ポリシロキサンを主体とする材料は、いず
れも涙液中の成分による汚染性を考慮しておらず、シリ
コーンラバーレンズに、より近い材料であるにもかかわ
らず、角膜との固着の問題にも触れていない。近年、酸
素透過性は高いにこしたことはないが、むしろ耐汚れ付
着性や装用性能のよいものが望まれている。Contact lens materials with high oxygen permeability based on polyfunctional polysiloxane are also disclosed in JP-A No. 54-24047,
Although described in Japanese Unexamined Patent Publication No. 56-51715, none of these polyfunctional polysiloxane-based materials take into account contamination by components in lachrymal fluid, and they are not suitable for silicone rubber lenses. Despite being a similar material, the problem of adhesion to the cornea is not addressed. In recent years, although oxygen permeability has never been higher, there has been a demand for products with better stain resistance and wearing performance.
〔発明が解決しようとする課題］
本発明はこのような実状のもとで、酸素透過性を表わす
酸素透過係数（ＤＫ値）が非常に高く、光学的、機械的
特性に優れ、且つ良好な装用感と耐汚れ付着性を有し、
角膜への固着の心配がない、実質的に非含水なソフトコ
ンタクトレンズ材料を提供することを目的としてなされ
たものである。[Problems to be Solved by the Invention] Under these circumstances, the present invention provides a material with a very high oxygen permeability coefficient (DK value) representing oxygen permeability, excellent optical and mechanical properties, and good properties. Comfortable to wear and stain resistant,
The purpose of this invention is to provide a substantially water-free soft contact lens material that does not have to worry about sticking to the cornea.
本発明者らは前記の好ましい性質を有する、非含水性ソ
フトコンタクトレンズ材料を開発すべく、鋭意研究を重
ねた結果、特定の構造と分子量を有する二官能性有機シ
ロキサン単量体と、アクリル酸フルオロアルキルエステ
ル単量体とを、特定の範囲で反応させて得られる共重合
体から成る材料により、その目的を達成しうろことを見
い出し、この知見に基づいて本発明を完成することがで
きた。The present inventors have conducted extensive research in order to develop a non-hydrous soft contact lens material having the above-mentioned favorable properties. It was discovered that the object could be achieved by a material consisting of a copolymer obtained by reacting a fluoroalkyl ester monomer within a specific range, and based on this knowledge, the present invention was completed. .
すなわち、本発明は一般式
（式中のＲ，Ｒ，Ｒ，及びＲ４はそれぞれ同−又は異な
るメチル基、又はトリメチルシロキシ基を表わし、２及
びｎはそれぞれ同一、又は異なる２〜５の整数であり、
ｍは１０〜１００の整数である）で表わされる二官能性
有機シロキサン単重体（＾）とアクリル酸フルオロアル
キルエステル単量体（Ｂ）とを、必須モノマー成分とし
、該２成分を重量比２０：８０ないし８５：１５の割合
で重合させて得られる共重合体からなる実質的に非含水
なソフトコンタクトレンズ材料を提供するものである。That is, the present invention is based on the general formula (R, R, R, and R4 each represent the same or different methyl group or trimethylsiloxy group, and 2 and n are each the same or different integers of 2 to 5). can be,
The bifunctional organosiloxane monomer (^) represented by m is an integer from 10 to 100) and the acrylic acid fluoroalkyl ester monomer (B) are essential monomer components, and the two components are mixed in a weight ratio of 20. The object of the present invention is to provide a substantially water-free soft contact lens material comprising a copolymer obtained by polymerizing at a ratio of: :80 to 85:15.
以下本発明の詳細な説明する。The present invention will be explained in detail below.
（１）
前記一般式（八）で表わされる二官能性有機シロキサン
単量体は、その分子量が増大する程、官能基開鎖が長く
なる為、酸素透過性が向上し、また凝集エネルギーを低
下させると共にガラス転移点も低くなる為、ソフトコン
タクトレンズとしたとき、柔らかさ、並びにゴム弾性で
示される形状保持性、及び戻り性等の物性に大きな効果
をもたらす。しかしながら、８亥単量体（八）のジメチ
ルシロキサニル単位の繰り返し数ｍが１００を越えると
単量体（Ｂ）との相溶性が悪化し、白濁したり相分離し
たりする。酸素透過性も繰り返し数ｍが増大すればする
程、顕著な差がなくなり、ｍを１００以上にしても大差
は見られないばかりか、シリコーンラバーレンズの性質
が強くなり、涙液中の成分による汚染性が増す原因とな
る。また操り返し＠ｍが１０以下になると酸素透過性が
かなり低下するばかりでなく、ソフトコンタクトレンズ
に必要な柔らかさや屈曲性が劣る原因となる。以上の理
由で分子量を決定する繰り返し数ｍの値は１０〜１００
好ましくは２０〜８０の範囲が最もバランスのとれた材
料を提供する。(1) As the molecular weight of the bifunctional organosiloxane monomer represented by the general formula (8) increases, the length of the functional group open chain becomes longer, which improves oxygen permeability and lowers the cohesive energy. At the same time, the glass transition point is also lowered, so when used as a soft contact lens, it has a great effect on physical properties such as softness, shape retention shown by rubber elasticity, and returnability. However, when the repeating number m of dimethylsiloxanyl units in the 8-monomer (8) exceeds 100, the compatibility with the monomer (B) deteriorates, resulting in cloudiness or phase separation. The oxygen permeability also becomes less noticeable as the repetition number m increases, and even when m is increased to 100 or more, not only is there no significant difference, but the properties of the silicone rubber lens become stronger, and the difference is due to the components in the tear fluid. This causes increased contamination. Furthermore, when the @m value is less than 10, not only the oxygen permeability is considerably reduced, but also the softness and flexibility necessary for soft contact lenses are deteriorated. For the above reasons, the value of the number of repetitions m that determines the molecular weight is 10 to 100.
Preferably a range of 20 to 80 provides the most balanced material.
前記一般式（Ａ）で表わされる二官能性有機シロキサン
単量体としては、例えば、ビス（３−メタクリロキシプ
ロピル）ポリジメチルシロキサン、ビス（３−メタクリ
ロキシプロピル）テトラキス（トリメチルシロキシ）ポ
リジメチルシロキサン、ビス（２−メタクリロキシエチ
ル）ポリジメチルシロキサンなどが挙げられる。Examples of the bifunctional organic siloxane monomer represented by the general formula (A) include bis(3-methacryloxypropyl)polydimethylsiloxane, bis(3-methacryloxypropyl)tetrakis(trimethylsiloxy)polydimethylsiloxane , bis(2-methacryoxyethyl)polydimethylsiloxane, and the like.
これらの単量体は１種だけ用いてもよいし、２種以上組
み合わせて用いてもよい。These monomers may be used alone or in combination of two or more.
次に前記単量体成分（Ｂ）として用いるアクリル酸フル
オロアルキルエステルは、フッ素原子に起因するしｎ界
表面張力の低下により、撥水、撥油性の性質を持ち、こ
れは、コンタクトレンズ表面が涙液中のタンパク質や脂
質などの成分によって汚染されることを抑える効果があ
る。また、この単量体成分は、物性的にガラス転移点が
室温以下であるものが多い為共重合した場合、ソフトコ
ンタクトレンズに必要な柔らかさや屈曲性を発現するこ
とができる。Next, the acrylic acid fluoroalkyl ester used as the monomer component (B) has water-repellent and oil-repellent properties due to the decrease in n-interface surface tension caused by fluorine atoms. It has the effect of suppressing contamination by components such as proteins and lipids in tear fluid. In addition, many of these monomer components have glass transition points below room temperature in terms of physical properties, so when copolymerized, they can exhibit the softness and flexibility necessary for soft contact lenses.
これらアクリル酸フルオロアルキルエステルの具体例と
しては、トリフルオロエチルアクリレート、テトラフル
オロエチルアクリレート、テトラフルオロプロピルアク
リレート、ペンタフルオロプロピルアクリレート、ヘキ
サフルオロブチルアクリレート、ヘキサフルオロイソプ
ロピルアクリレート、ヘプタフルオロブチルアクリレー
ト、オクタフルオロペンチルアクリレートなどが挙げら
れ、これらの単量体は１種用いてもよいし、２種以上組
み合わせて用いてもよい。Specific examples of these acrylic acid fluoroalkyl esters include trifluoroethyl acrylate, tetrafluoroethyl acrylate, tetrafluoropropyl acrylate, pentafluoropropyl acrylate, hexafluorobutyl acrylate, hexafluoroisopropyl acrylate, heptafluorobutyl acrylate, and octafluoropentyl acrylate. Examples include acrylate, and these monomers may be used alone or in combination of two or more.
本発明の非含水性ソフトコンタクトレンズ材料として用
いられる共重合体は前記（Ａ）成分の二官能性有機シロ
キサン単量体と（Ｂ）成分のアクリル酸フルオロアルキ
ルエステル単量体とを重量比２０：８０ないし８５：１
５好ましくは３０ニア０ないし７０：３０の割合で共重
合させることが必要である。二官能性有機シロキサン単
量体の使用量が前記範囲を越えると重合時に白濁が起こ
ったり、単量体の混合時に２相分離したりする。The copolymer used as the non-water-containing soft contact lens material of the present invention contains the difunctional organosiloxane monomer as the component (A) and the acrylic acid fluoroalkyl ester monomer as the component (B) in a weight ratio of 20. :80 to 85:1
It is necessary to copolymerize in a ratio of preferably 5:30 to 70:30. If the amount of the difunctional organosiloxane monomer used exceeds the above range, clouding may occur during polymerization or two phases may separate during mixing of the monomers.
また、アクリル酸フルオロアルキルエステルの耐汚れ付
着性の効果が減じられ、涙液中の成分による汚染が心配
される。二官能性有機シロキサン単量体の使用量が前記
範囲未満では酸素透過性がかなり低下し、物性的にも戻
り性等が悪化する。Furthermore, the stain-proofing effect of the acrylic acid fluoroalkyl ester is reduced, and there is concern about contamination by components in lachrymal fluid. If the amount of the difunctional organosiloxane monomer used is less than the above range, the oxygen permeability will be considerably lowered and the physical properties such as return properties will be deteriorated.
本発明の非含水性ソフトコンタクトレンズ材料として用
いられる共重合体においては、機械的性質、表面濡れ性
、レンズの寸法安定性などを向上させるために、所望に
応じ、全単量体の重量の５０重量％以下であれば、他の
単量体を共重合させることができる。In the copolymer used as the water-free soft contact lens material of the present invention, in order to improve mechanical properties, surface wettability, dimensional stability of the lens, etc., the total monomer weight may be reduced as desired. Other monomers can be copolymerized as long as the amount is 50% by weight or less.
機械的性質を向上させるための単量体としては、例えば
メチルメタクリレート、エチルメタクリレート、ｔ−ブ
チルメタクリレート、ｎ−ブチルメタクリレート、シク
ロへキシルメタクリレート、ベンジルメタクリレートな
どのメタクリレート類、及びこれらに対応するアクリレ
ート類、スチレン、ｔ−ブチルスチレン、α−メチルス
チレンなどの芳香族ビニル化合物などが挙げられる。Examples of monomers for improving mechanical properties include methacrylates such as methyl methacrylate, ethyl methacrylate, t-butyl methacrylate, n-butyl methacrylate, cyclohexyl methacrylate, and benzyl methacrylate, and acrylates corresponding to these. , styrene, t-butylstyrene, α-methylstyrene, and other aromatic vinyl compounds.
表面濡れ性を向上させるための単量体としては、例えば
メタクリル酸、アクリル酸、・イタコン酸、２−とドロ
キシエチルメタクリレート、２−ヒドロキシエチルアク
リレート、２−ヒドロキシプロピルメタクリレート、２
−ヒドロキシプロピルアクリレート、グリセロールメタ
クリレート、ポリエチレングリコールメククリレート、
Ｎ、Ｎ’ −ジメチルアクリルアミド、Ｎ−メチルアク
リルアミド、Ｎ−ビニルピロリドンなどが挙げられる。Examples of monomers for improving surface wettability include methacrylic acid, acrylic acid, itaconic acid, 2- and droxyethyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl methacrylate, and 2-hydroxypropyl methacrylate.
-Hydroxypropyl acrylate, glycerol methacrylate, polyethylene glycol meccrylate,
Examples include N,N'-dimethylacrylamide, N-methylacrylamide, and N-vinylpyrrolidone.
レンズの寸法安定性を向上させるための単量体としては
、例えばエチレングリコールジメタクリレート、ジエチ
レングリコールジメタクリレート、トリエチレングリコ
ールジメタクリレート、ポリエチレングリコールジメタ
クリレート、トリメチロールプロパントリメタクリレー
ト、ペンタエリスリトールテトラメタクリレート、ビス
フェノールＡジメタクリレート、ビニルメタクリレート
、アクリルメタクリレート及びこれらのメタクリレート
ＩＩに対応するアクリレート類、ジビニルベンゼン、ト
リアリルイソシアヌレートなどが挙げられる。Examples of monomers for improving the dimensional stability of lenses include ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, polyethylene glycol dimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol tetramethacrylate, and bisphenol A. Examples include dimethacrylate, vinyl methacrylate, acrylic methacrylate, acrylates corresponding to these methacrylates II, divinylbenzene, triallylisocyanurate, and the like.
これらの所望に応じて用いられる単量体は、１種用いて
もよいし、２種以上を組み合わせて用いてもよい。These monomers used as desired may be used alone or in combination of two or more.
本発明のコンタクトレンズ材料として用いられる共重合
体は、単量体混合物を鋳型に充填して公知のラジカル重
合によって得られる。共重合の方法は、ヘンジイン、ベ
ンゾフェノン、ベンジルジメチルケタノールなどの光重
合開始剤を単量体混合物中に存在させ、紫外線を照射し
て重合させる方法、又はアゾビスイソブチロニトリル、
ペンゾイルパーオキサド、ラウロイルパーオキサイドな
どのアゾ化合物、若しくは有機過酸化物を用いてて熱重
合させる方法がよい。The copolymer used as the contact lens material of the present invention is obtained by filling a mold with a monomer mixture and performing known radical polymerization. The copolymerization method includes a method in which a photopolymerization initiator such as hengeine, benzophenone, benzyldimethylketanol, etc. is present in the monomer mixture, and polymerization is carried out by irradiation with ultraviolet rays, or a method in which a photopolymerization initiator such as hengeine, benzophenone, benzyldimethylketanol, etc.
A method of thermal polymerization using an azo compound such as penzoyl peroxide or lauroyl peroxide, or an organic peroxide is preferable.
（八）成分の三官能性能有機シロキサン単量体と（Ｂ）
成分のアルキル酸フルオロアルキルエステル単量体とを
必須上ツマー成分とし、該２成分の使用割合が重量比２
０ ： ８０ないし８５ ： １５の範囲にある共重合
体は、その共重合比等を変えることにより、３０ＸｌＯ
−” 〜３００ＸＩＯ−” ｄ −ｃｍ／ｃｒＡｓｅｃ
ｔｕｍＨｇ程度の酸素透過係数を持ち、光学的、機械的
特性に優れ、且つ良好な装用感と市販品並の涙液による
汚染性を有する非常にバランスのとれた非含水ソフトコ
ンタクトレンズ材料を提供することができる。(8) component trifunctional performance organosiloxane monomer and (B)
The alkyl acid fluoroalkyl ester monomer of the component is an essential component, and the proportion of the two components used is 2 by weight.
A copolymer in the range of 0:80 to 85:15 can be made into 30XlO by changing the copolymerization ratio etc.
-” ~300XIO-” d -cm/crAsec
To provide a very well-balanced water-free soft contact lens material that has an oxygen permeability coefficient on the order of tumHg, excellent optical and mechanical properties, good wearing comfort, and tear stain resistance comparable to commercially available products. be able to.
コンタクトレンズの角膜固着については種々の議論がな
されており、例えば日本コンタクトレンズ学会誌、第２
８巻、第１９１〜１９７ページ（１９８６年）によれば
シリコーンラバーレンズの固着防止対策として、材質硬
度を高くし、ゴム硬度５ｈｏｒｅ Ａ ６０〜６５以上
にし、且つレンズデザインを考慮することにより、はぼ
固着の心配が無くなることが報告されている。本発明に
よる共重合体も共重合比等を考慮することにより、他の
物性を低下させずに、ゴム硬度５ｈｏｒｅ Ａを６０〜
６５以上に容易にすることができる。There have been various discussions regarding the corneal fixation of contact lenses, for example, in the Journal of the Japanese Contact Lens Society, Vol.
According to Vol. 8, pp. 191-197 (1986), as a measure to prevent silicone rubber lenses from sticking, by increasing the hardness of the material, making the rubber hardness 5hole A 60-65 or higher, and by considering the lens design. It has been reported that there is no need to worry about sticking. By considering the copolymerization ratio, etc., the copolymer according to the present invention has a rubber hardness of 5hole A of 60 to 60 without deteriorating other physical properties.
65 or more.
次に実施例により本発明を更に詳細に説明するが、本発
明はこれらの例によってなんら限定されるものではない
。EXAMPLES Next, the present invention will be explained in more detail with reference to examples, but the present invention is not limited to these examples in any way.
なお、各物性及び分子量は次のようにして求めた。In addition, each physical property and molecular weight were calculated|required as follows.
（１）酸素透過係数
理化精機工業株式会社製の気体透過率測定装置に−３１
５−Ｎを用いた。試料片は直径３０調、厚さ０．３胴の
円盤状のものを測定に供し、得られたチャート上の直線
の傾きから、酸素透過係数を計算によって求めた。測定
は２５°Ｃの恒温室内、試料片セット場所３５°Ｃで実
施した。(1) Oxygen permeability coefficient -31 to the gas permeability measuring device manufactured by Rika Seiki Kogyo Co., Ltd.
5-N was used. A disk-shaped sample piece with a diameter of 30 mm and a thickness of 0.3 mm was used for measurement, and the oxygen permeability coefficient was calculated from the slope of the straight line on the obtained chart. The measurements were carried out in a constant temperature room at 25°C, with the sample piece set at 35°C.
（２）接触角
協和界面科学株式会社製、Ｃｏｎｔａｃｔ Ａｎｇｌｅ
ＭｅｔｅｒＣＡ−Ａを用いた。試料片は測定の前に鏡
面研磨を施し、界面活性剤を使って表面の汚れを落とし
たのち、生理食塩水中に２４時間浸せきしてから測定に
供した。測定は試料片を純水中に静置し、シリンジによ
り直径１．５〜２．０ ｔｍｍの気泡を試料片下面に接
触させ、その気泡と試料片が形成する角度を読み取り、
計算によって接触角を求めた。(2) Contact Angle manufactured by Kyowa Interface Science Co., Ltd.
MeterCA-A was used. Before measurement, the sample pieces were mirror-polished, surface dirt was removed using a surfactant, and then immersed in physiological saline for 24 hours before being used for measurement. For measurement, the sample piece is placed in pure water, a bubble with a diameter of 1.5 to 2.0 tmm is brought into contact with the bottom surface of the sample piece using a syringe, and the angle formed between the bubble and the sample piece is read.
The contact angle was determined by calculation.
（３）引張り強度
株式会社今田製作所製の万能引張圧縮試験機５Ｖ−５０
を用いた。試料片は厚さ０．３ ａｍ、中５．０ｍ。(3) Tensile strength Universal tensile compression tester 5V-50 manufactured by Imada Seisakusho Co., Ltd.
was used. The sample piece has a thickness of 0.3 am and a medium diameter of 5.0 m.
長さ３０ｍｍのものを測定に供した。引張り速度は１０
ｍｍ／ｍｉｎであった。測定は同一試料片について３
回行い、得られた値からＪ Ｉｓ−に−６３０１記載の
計算方法に従って引張り強度を求めた。A piece with a length of 30 mm was used for measurement. The pulling speed is 10
mm/min. Measurements were made on the same sample piece 3
The tensile strength was determined from the obtained value according to the calculation method described in J Is-6301.
（４）汚れ付着性
日本コンタクトレンズ学会誌、第２４巻、第２７７〜２
８３ページ（１９８２年〕に記載の方法により、汚れ付
着試験を行った。試料片は厚さ２１１ＩＩ１１、巾５加
、長さ３０ＩＴＩＩＴｌのものを用いた。判定は対照と
してＰＭＭＡの試料片を同様に操作したときの汚れ付着
を基準として、肉眼観察でそれより汚れ付着の程度が少
ない場合を「少」、多い場合を「多」、同等の場合を［
同等Ｊとした。なお、汚れ物質のモデルとしてムチン（
生前粘膜）、リゾチーム（卯白）、レシチン（卵黄）の
３種類を使用した。(4) Dirt adhesion Journal of the Japanese Contact Lens Society, Vol. 24, No. 277-2
A stain adhesion test was conducted according to the method described on page 83 (1982).The sample piece had a thickness of 211II11, a width of 5+, and a length of 30ITIITl.The judgment was made using a PMMA sample piece as a control. Based on the dirt adhesion during operation, if the degree of dirt adhesion is less than that when observed with the naked eye, it is judged as "little", if it is more, it is "extreme", and if it is the same, it is [
Equivalent to J. In addition, mucin (
Three types were used: antemortem mucosa), lysozyme (Urushiro), and lecithin (egg yolk).
（５）硬度
ＪＩＳ−に−６３０１記載の方法に準じ、硬度（Ｓｈｏ
ｒｅ Ａ）測定した。(5) Hardness According to the method described in JIS-6301, hardness (Sho
re A) Measured.
（６）二官能性有機シロキサン単量体（八）の分子量Ｍ
ｎの測定
液体クロマトグラフ： ＬＣ−３Ａ型（島津製作所■製
）
カ ラ ム ： ５ｈｏｄｅｘ
８０２＋８０３ ＋８０５（昭和電工■製）
検出器 ： ＥＲＣ−７５１０Ｓ
（エルマ光学■製）
インチグレーター ニア０００Ａ （システムインス
ツルメンツ社製）
展 開 溶 媒 ： トルエン
温 度 ： ２５°Ｃ分子量検量線
用標準ポリマー
：単分散ポリスチレン各種
（東洋曹達■製）
（Ｍｗ／Ｍｎ＝１．２（ｏ＋ａｘ））
Ｍｎ及びｍは上記分析結果より計算で求める。(6) Molecular weight M of bifunctional organosiloxane monomer (8)
Measurement of n Liquid chromatograph: LC-3A type (manufactured by Shimadzu Corporation) Column: 5hodex
802+803 +805 (manufactured by Showa Denko ■) Detector: ERC-7510S (manufactured by Elma Optical ■) Inch Grater Near 000A (manufactured by System Instruments) Solvent: Toluene Temperature: 25°C Standard polymer for molecular weight calibration curve: Single Various types of dispersed polystyrene (manufactured by Toyo Soda ■) (Mw/Mn=1.2 (o+ax)) Mn and m are calculated from the above analysis results.
実施例１
ビス（３−メタクリロキシプロピル）ポリジメチルシロ
キサン（分子量Ｍｎ中２５００．ｍ＊３０） ５０重
量部、ＡＡ−ＦＩＰ５０重量部、ベンジルジメチルケタ
ノール０．５重部をマグネチックスクーラーにて１時間
かきまぜ混合して重合用単量体混合物を調整した。前記
共重合用単量体混合物を、シリコーンゴム製のガスケッ
トを間に入れた２枚のガラス板（厚さ１０胴、巾５０１
１Ｉ１１、長さ１１００ａ＋）で組んだセル中に注入し
、該セルを５０〜６０°Ｃの温度において、紫外線を２
時間照射して共重合体を得た。このようにして得られた
共重合体について、酸素透過係数、接触角、引張り強度
、汚れ付着性、硬度を測定した。その結果を表１に示す
。Example 1 50 parts by weight of bis(3-methacryloxypropyl)polydimethylsiloxane (molecular weight 2500.m*30 in Mn), 50 parts by weight of AA-FIP, and 0.5 parts by weight of benzyl dimethyl ketanol were added to 1 part by weight in a magnetic cooler. A monomer mixture for polymerization was prepared by stirring and mixing for a period of time. The copolymerization monomer mixture was placed between two glass plates (thickness 10 mm, width 50 mm) with a silicone rubber gasket inserted between them.
1I11, length 1100a+), and the cell was exposed to ultraviolet rays at a temperature of 50 to 60°C.
A copolymer was obtained by irradiation for a period of time. The thus obtained copolymer was measured for oxygen permeability coefficient, contact angle, tensile strength, stain adhesion, and hardness. The results are shown in Table 1.
実施例２
ビス（３−メタクリロキシプロピル）ポリジメチルシロ
キサン（以下ＰＤＭＳと略す） 分子量Ｍｎ中２５００
、ＩＩＩ中３０） ５０重量部、ヘキサフルオロイソプ
ロピルアクリレート（以下Ａ＾−ＰＩＰと略す）４０重
量部、ｎ−ブチルアクリレート（以下ｎ−ＨＡと略すＮ
０重量部、メタクリル酸（以下ＭＡＡと略す）５重量部
、ジエチレングリコールジメタクリレート（以下２ＥＩ
）と略す）５重量部、及びベンジルジメチルケタノール
（チバガイギー社ｌ−６５１） ０．５重量部を混合し
たものを実施例１と同様な操作を行い共重合体を得た。Example 2 Bis(3-methacryloxypropyl)polydimethylsiloxane (hereinafter abbreviated as PDMS) Molecular weight 2500 in Mn
, III (30) 50 parts by weight, 40 parts by weight of hexafluoroisopropyl acrylate (hereinafter abbreviated as A^-PIP), n-butyl acrylate (hereinafter abbreviated as n-HA)
0 parts by weight, 5 parts by weight of methacrylic acid (hereinafter abbreviated as MAA), diethylene glycol dimethacrylate (hereinafter 2EI)
)) and 0.5 parts by weight of benzyl dimethyl ketanol (Ciba Geigy L-651) were mixed and the same operation as in Example 1 was carried out to obtain a copolymer.
その物性を測定した結果を表１に示す。Table 1 shows the results of measuring its physical properties.
前記共重合用単量体混合物を、射出成形によって作成し
たポリプロピレン製の凹凸鋳型に充填し、紫外線を２時
間照射した。照射後、鋳型からとり出したレンズは、透
明で柔らかく、その強度、戻り性も良好であった。この
レンズを界面活性剤の入った水溶液で洗浄し、純水中で
保管すると水濡れ性の良いレンズが得られた。The monomer mixture for copolymerization was filled into a polypropylene uneven mold made by injection molding, and irradiated with ultraviolet rays for 2 hours. After irradiation, the lens taken out from the mold was transparent, soft, and had good strength and returnability. When this lens was washed with an aqueous solution containing a surfactant and stored in pure water, a lens with good water wettability was obtained.
実施例３及び４
実施例２において使用したビス（３−メタクリロキシプ
ロピル）ポリジメチルシロキサン（分子１Ｍｎ中２５０
０．ｓ＋中３０）の分子量を実施例３はＭｎ中３５００
、ｍ中４３とし、実施例４はＭｎ中４８００．−申６０
としたものを用いた以外は、実施例２と同様にして共重
合体を得、その物性を測定した。結果を表１に示す。Examples 3 and 4 Bis(3-methacryloxypropyl)polydimethylsiloxane used in Example 2 (250
0. Example 3 has a molecular weight of 3500 in Mn.
, 43 in Mn, and in Example 4, 4800. in Mn. - Monkey 60
A copolymer was obtained in the same manner as in Example 2, except that a copolymer was used, and its physical properties were measured. The results are shown in Table 1.
実施例５
実施例２において使用したＡＡ−ＦＩＰをトリフルオロ
エチルアクリレート（以下３ＦＡと略す）にした以外は
、実施例２と同様にして共重合体を得、その物性を測定
した。結果を表１に示す。Example 5 A copolymer was obtained in the same manner as in Example 2, except that AA-FIP used in Example 2 was replaced with trifluoroethyl acrylate (hereinafter abbreviated as 3FA), and its physical properties were measured. The results are shown in Table 1.
実施例６〜１１
ビス（３−メタクリロキシプロピル）ポリジメチルシロ
キサン（分子量Ｍｎ中２５００．ｍ中３０） 、ＡへＦ
ＩＰ 、 ３ＦＡ 、 ｎ−ＢＡ、 ＭＡＡ 、２ＥＤ
の単量体を表１に記載の割合でまぜ合わゼ混合物を作成
し、実施例１と同様にして共重合体を得、その物性を測
定した。結果を表１に示す。Examples 6-11 Bis(3-methacryloxypropyl)polydimethylsiloxane (molecular weight Mn 30 in 2500.m), A to F
IP, 3FA, n-BA, MAA, 2ED
A mixture was prepared by mixing the monomers in the proportions shown in Table 1, a copolymer was obtained in the same manner as in Example 1, and its physical properties were measured. The results are shown in Table 1.
比較例１
実施例１において使用したビス（３−メタクリロキシプ
ロピル）ポリジメチルシロキサン（分子量Ｍｎ中２５０
０．ｍ中３０）単量体１００重量部にベンジルジメチル
ケタノール０．５重量部を加えまぜ合わせ、実施例１と
同様にして重合体を得、その物性を測定した。その結果
を表１に示す。Comparative Example 1 Bis(3-methacryloxypropyl)polydimethylsiloxane used in Example 1 (molecular weight Mn: 250
0. 0.5 parts by weight of benzyldimethylketanol was added to 100 parts by weight of the monomer (30) in m and mixed together to obtain a polymer in the same manner as in Example 1, and its physical properties were measured. The results are shown in Table 1.
（以下余白）
〔発明の効果〕
本発明のコンタクトレンズ材料は特定の構造を有する二
官能性ポリジメチルシロキサン単量体と、アクリル酸フ
ルオロアルキルエステル単量体とを、特定の範囲内で必
須成分として含む単量体混合物を、重合して得られるも
のであって、酸素透過性が高く、親水性に優れ、機械的
性質が良好である上に、耐汚れ付着性がＰＭＭＡ系ハー
ドコンタクトレンズに匹敵するレンズを与えることがで
きる。また硬度の調整が容易で、角膜への固着のおそれ
がないレンズを提供することができる。(Left below) [Effects of the Invention] The contact lens material of the present invention contains a bifunctional polydimethylsiloxane monomer having a specific structure and an acrylic acid fluoroalkyl ester monomer as essential components within a specific range. It is obtained by polymerizing a monomer mixture containing as Comparable lenses can be provided. Further, it is possible to provide a lens whose hardness can be easily adjusted and which has no risk of sticking to the cornea.
Claims (1)
又は異なるメチル基又はトリメチルシロキシ基を表わし
、ｌ及びｎはそれぞれ同一、又は異なる２〜５の整数で
あり、ｍは１０〜１００の整数である）で表わされる二
官能性有機シロキサン単量体（Ａ）とアクリル酸フルオ
ロアルキルエステル単量体（Ｂ）とを、必須モノマー成
分とし、該２成分を重量比２０：８０ないし８５：１５
の割合で重合させて得られる共重合体から成るコンタク
トレンズ材料。[Claims] General formula ▲ Numerical formula, chemical formula, table, etc. ▼ 5 and m is an integer of 10 to 100) as essential monomer components, a bifunctional organosiloxane monomer (A) represented by The weight ratio of the two components is 20:80 to 85:15.
A contact lens material consisting of a copolymer obtained by polymerizing at a ratio of .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3608890A JPH03240021A (en) | 1990-02-19 | 1990-02-19 | Contact lens material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3608890A JPH03240021A (en) | 1990-02-19 | 1990-02-19 | Contact lens material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03240021A true JPH03240021A (en) | 1991-10-25 |
Family
ID=12460000
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3608890A Pending JPH03240021A (en) | 1990-02-19 | 1990-02-19 | Contact lens material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03240021A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05117349A (en) * | 1991-01-09 | 1993-05-14 | Ciba Geigy Ag | Hard contact lens of improved oxygen permeability |
| WO2013024856A1 (en) * | 2011-08-17 | 2013-02-21 | 東レ株式会社 | Medical device, and method for producing same |
| JP2014040598A (en) * | 2013-10-03 | 2014-03-06 | Menicon Co Ltd | Polymer material, ocular lens, and contact lens |
| JPWO2013024800A1 (en) * | 2011-08-17 | 2015-03-05 | 東レ株式会社 | Low hydrous soft device and manufacturing method thereof |
| JP2017132947A (en) * | 2016-01-29 | 2017-08-03 | 信越化学工業株式会社 | Water-absorbing resin having siloxane skeleton and cosmetics comprising the same |
-
1990
- 1990-02-19 JP JP3608890A patent/JPH03240021A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05117349A (en) * | 1991-01-09 | 1993-05-14 | Ciba Geigy Ag | Hard contact lens of improved oxygen permeability |
| WO2013024856A1 (en) * | 2011-08-17 | 2013-02-21 | 東レ株式会社 | Medical device, and method for producing same |
| JPWO2013024856A1 (en) * | 2011-08-17 | 2015-03-05 | 東レ株式会社 | Medical device and manufacturing method thereof |
| JPWO2013024800A1 (en) * | 2011-08-17 | 2015-03-05 | 東レ株式会社 | Low hydrous soft device and manufacturing method thereof |
| US9377562B2 (en) | 2011-08-17 | 2016-06-28 | Toray Industries, Inc. | Medical device, and method for producing same |
| JP2014040598A (en) * | 2013-10-03 | 2014-03-06 | Menicon Co Ltd | Polymer material, ocular lens, and contact lens |
| JP2017132947A (en) * | 2016-01-29 | 2017-08-03 | 信越化学工業株式会社 | Water-absorbing resin having siloxane skeleton and cosmetics comprising the same |
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