CN1164661A - 由潜在亲水性单体制得的具有可湿性表面的模塑聚合制品 - Google Patents
由潜在亲水性单体制得的具有可湿性表面的模塑聚合制品 Download PDFInfo
- Publication number
- CN1164661A CN1164661A CN97104532A CN97104532A CN1164661A CN 1164661 A CN1164661 A CN 1164661A CN 97104532 A CN97104532 A CN 97104532A CN 97104532 A CN97104532 A CN 97104532A CN 1164661 A CN1164661 A CN 1164661A
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- CN
- China
- Prior art keywords
- water wettability
- polymerizable material
- potential water
- moulding article
- mould
- 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.)
- Granted
Links
- 239000000178 monomer Substances 0.000 title claims abstract description 57
- 238000000034 method Methods 0.000 claims abstract description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 44
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 33
- 239000000463 material Substances 0.000 claims description 32
- 238000000576 coating method Methods 0.000 claims description 23
- 239000011248 coating agent Substances 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 239000001301 oxygen Substances 0.000 claims description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 19
- -1 polypropylene Polymers 0.000 claims description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 18
- 230000035699 permeability Effects 0.000 claims description 17
- 238000000465 moulding Methods 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 125000000524 functional group Chemical group 0.000 claims description 14
- 229920000642 polymer Polymers 0.000 claims description 13
- 230000002209 hydrophobic effect Effects 0.000 claims description 10
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 9
- 230000008859 change Effects 0.000 claims description 7
- 229920001451 polypropylene glycol Polymers 0.000 claims description 7
- 239000004743 Polypropylene Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229920001155 polypropylene Polymers 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 5
- 229920005573 silicon-containing polymer Polymers 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- 150000007942 carboxylates Chemical class 0.000 claims description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000002926 oxygen Chemical class 0.000 claims 2
- 150000005690 diesters Chemical class 0.000 claims 1
- 239000003999 initiator Substances 0.000 claims 1
- 229920001477 hydrophilic polymer Polymers 0.000 abstract description 6
- 230000008569 process Effects 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 21
- 229920001296 polysiloxane Polymers 0.000 description 19
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 15
- 239000012267 brine Substances 0.000 description 14
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
- 239000004793 Polystyrene Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 229920002223 polystyrene Polymers 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 9
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- 239000000017 hydrogel Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 210000004087 cornea Anatomy 0.000 description 5
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 4
- NIXVAPHNPNMUIX-UHFFFAOYSA-N 6-amino-2-methylhex-2-enamide Chemical compound NC(=O)C(C)=CCCCN NIXVAPHNPNMUIX-UHFFFAOYSA-N 0.000 description 4
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- GNWBLLYJQXKPIP-ZOGIJGBBSA-N (1s,3as,3bs,5ar,9ar,9bs,11as)-n,n-diethyl-6,9a,11a-trimethyl-7-oxo-2,3,3a,3b,4,5,5a,8,9,9b,10,11-dodecahydro-1h-indeno[5,4-f]quinoline-1-carboxamide Chemical compound CN([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)N(CC)CC)[C@@]2(C)CC1 GNWBLLYJQXKPIP-ZOGIJGBBSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229920001600 hydrophobic polymer Polymers 0.000 description 3
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 3
- GUAQVFRUPZBRJQ-UHFFFAOYSA-N n-(3-aminopropyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCCCN GUAQVFRUPZBRJQ-UHFFFAOYSA-N 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 102100026735 Coagulation factor VIII Human genes 0.000 description 2
- 206010011033 Corneal oedema Diseases 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 229920005601 base polymer Polymers 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 201000004778 corneal edema Diseases 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 210000003560 epithelium corneal Anatomy 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 230000004438 eyesight Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 125000005401 siloxanyl group Chemical group 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-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
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-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
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920000298 Cellophane Polymers 0.000 description 1
- 241001391944 Commicarpus scandens Species 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000010669 acid-base reaction Methods 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000007975 buffered saline Substances 0.000 description 1
- HGAZMNJKRQFZKS-UHFFFAOYSA-N chloroethene;ethenyl acetate Chemical compound ClC=C.CC(=O)OC=C HGAZMNJKRQFZKS-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 206010023332 keratitis Diseases 0.000 description 1
- 125000003473 lipid group Chemical group 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 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
- 230000003287 optical effect Effects 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Substances OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- JCWLEWKPXYZHGQ-UHFFFAOYSA-N propan-2-yl 2-bromoacetate Chemical compound CC(C)OC(=O)CBr JCWLEWKPXYZHGQ-UHFFFAOYSA-N 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/06—Coating with compositions not containing macromolecular substances
- C08J7/065—Low-molecular-weight organic substances, e.g. absorption of additives in the surface of the article
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C37/00—Component parts, details, accessories or auxiliary operations, not covered by group B29C33/00 or B29C35/00
- B29C37/0025—Applying surface layers, e.g. coatings, decorative layers, printed layers, to articles during shaping, e.g. in-mould printing
- B29C37/0028—In-mould coating, e.g. by introducing the coating material into the mould after forming the article
- B29C37/0032—In-mould coating, e.g. by introducing the coating material into the mould after forming the article the coating being applied upon the mould surface before introducing the moulding compound, e.g. applying a gelcoat
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C41/00—Shaping by coating a mould, core or other substrate, i.e. by depositing material and stripping-off the shaped article; Apparatus therefor
- B29C41/02—Shaping by coating a mould, core or other substrate, i.e. by depositing material and stripping-off the shaped article; Apparatus therefor for making articles of definite length, i.e. discrete articles
-
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Abstract
本发明提供一种模塑聚合制品,其部分或全部涂布亲水性聚合物,使得该模塑制品例如隐形眼镜具有可湿性的表面,同时也提供使用潜在亲水性单体制造具有可湿性表面的模塑制品的方法。
Description
隐形眼镜因为具有美观及光学性质,所以广泛地供视力矫正使用。数种健康及舒适的问题已经报导与用来制造这种隐形眼镜的材料的可湿性及透氧性相关。因为角膜没有血管,正常代谢所需的氧气直接得自与其接触的空气。很久以前就知道使用隐形眼镜会降低角膜可得到的氧气的量,且此点经常造成角膜水肿。研究显示兔子配戴隐形眼镜时,因为可得到的氧气减少而使上皮缺陷的治愈率降低。也曾经报导兔子戴隐形眼镜时,随著透氧性的降低而使铜绿假单胞菌增加在兔子角膜上的吸附。据信细菌例如铜绿假单胞菌在角膜上皮的吸附是造成细菌性角膜炎的第一步骤,此种感染可导致视力的永久损伤。
软性隐形眼镜通常是用水凝胶聚合物类制成,例如轻微交联的聚甲基丙烯酸羟乙酯(polyHEMA)。水凝胶类的透氧性通常为其含水量的函数。隐形眼镜的极限氧气可透性等于其透氧性除以其厚度。polyHEMA水凝胶类的水含量为约38%(水重量/水合聚合物重量),因为透氧性太低会造成角膜水肿而无法作为隐形眼镜使用,尤其是当镜片是在长时间配戴模式下使用,即连续配戴数天没有取下。
经由包括更高度亲水性单体类例如甲基丙烯酸或N-乙烯基吡咯烷酮,可能制造出有更高含水量的水凝胶类,因此有更大的透氧性;但是此种高含水量的水凝胶类通常有不良的机械强度,因此用其制造出来的非常薄的隐形眼镜很难处理或很容易破裂。同时也发现用高含水量水凝胶类制造出来的薄的隐形眼镜,会造成刺激角膜的外上皮表面。
为了克服水凝胶隐形眼镜的透氧性限制,曾经使用硅酮和其他疏水性聚合物类例如多氟化聚合物类及聚丙二醇作为隐形眼镜的材料。此类材料的透氧性可以非常高;但是此类材料的表面通常有非常差的可湿性。而且此类聚合物的表面通常对某些眼泪成分例如蛋白质类、类脂物及粘蛋白有亲和性。此种不能令人满意的表面特性,使得用这些材料制成的镜片,在配戴时快速受到不透光的沉积物污染。此种镜片也非常不舒服,而且也可能变成紧密吸附在角膜上,可能导致角膜上皮的严重伤害。
用上述高透氧性低水含量聚合物制造隐形眼镜的其中一种可能方式,是在用此高透氧性低水含量聚合物制成的镜片表面上形成亲水聚合物涂膜。颁给E.Merrill的美国专利3,916,033及4,099,859揭示在预先形成的硅酮隐形眼镜上涂上亲水性聚合物。Merrill也揭示在从用亲水性单体处理过的、然后放在模具表面上的玻璃纸膜上将亲水性单体转移的同时,形成硅酮镜片。其中叙述的步骤繁杂且很难控制,而且需要非常高的能量进行可能有害的离子化放射。
颁给Mueller的欧洲专利362,137及美国专利5,010,155揭示一种从具有亲水性聚合表面的疏水性聚合物形成隐形眼镜的方法,所叙述的方法很难进行,因为形成涂膜的聚合物可能既没有足够大的亲水性使镜片表面可非常湿化,或因为通常很难在方法所需的隐形眼镜模具内表面形成亲水性聚合物涂膜,尤其是当模具是用塑料例如聚丙烯或聚苯乙烯制成时。
曾经尝试多种方法将亲水性成分混入高透氧疏水性物质以增加其表面可湿性,但是源自本体聚合物改良的表面可湿性增加通常随著损失大量透氧性。例如颁给J.kunzler及R.Ozark的美国专利5,321,108揭示新颖的含氟硅氧烷单体供隐形眼镜使用。但是当加入亲水性单体例如二甲基丙烯酰胺(DMA)以便使聚合物更有亲水性时,透氧性(Dk)从530降低至52。颁给J.McGee及P.Valint的美国专利5,336,797揭示当亲水性单体例如DMA添加至硅氧烷单体掺合物时,Dk从238-353降低至62-187。另一种使疏水性硅氧烷聚合物具有所需的亲水性的方法揭示在颁给P.Koegh、J.Kunzler及G.Niu的美国专利4,259,467。合成含亲水性侧链的可聚合性聚硅氧烷类并用于制造隐形眼镜。或者是在颁给J.Robertson、K.Su、M.Goldenberg及K.Mueller的美国专利5,070,169揭示从含有羟水性单位例如聚乙二醇的聚硅氧烷类嵌段共聚物制造隐形眼镜。全部的这些方法都无法得到足够的可湿化表面、或所需的高Dk。
也曾经尝试经由在此类聚合物的表面进行化学反应,改良这些表面并使其可湿化,以解决疏水性隐形眼镜聚合物不良可湿性的问题,例如颁给Menicon Co.的欧洲专利379,146揭示从聚硅氧烷、(甲基)丙烯酸烷基酯及含氟单体的共聚物制造软性隐形眼镜。所提供的实例是在这些镜片上进行碱性处理,以便使表面具有亲水性的本质。此种处理很难控制,所以所需的效应施加至镜面后,表面不是仍然为疏水性,就是会降解隐形眼镜的本体。
本发明是关于一种制品,例如用具有透氧性并涂有潜在亲水性聚合物的本体聚合物的物体制造的隐形眼镜,以及制备该制品的方法,其步骤包括:
(a)施加一种正常疏水性/潜在亲水性的可聚合化物质至生产制品
的模具的内部表面;
(b)在涂布化的模具内填入单体物质,该物质可聚合成透氧性的
聚合物;
(c)将模具内的物质固化而产生涂布化的制品,例如隐形眼镜;
及
(d)在温和的反应条件下处理涂布化的模塑制品,使涂膜转化成
更亲水性的形式。
本发明提供一种模塑聚合物制品,其部分或全部涂布亲水性聚合物,使得该模塑制品具有可湿性的表面,同时也提供使用由通常生产疏水性聚合物的单体制造的潜在亲水性物质,以制造具有可湿性表面的模塑制品的方法。
在此方法中,使用一种潜在亲水性可聚合化的物质,即单体、单体的混合物、或涂有一或多种潜在亲水性可聚合化的物质的预聚物,涂在隐形眼镜模具的部分或全部的内表面。潜在亲水性物质是选自包括含有官能基的物质,该官能基可在温和条件下经化学转化成亲水性官能基,以离子性基团较佳。使用这些物质产生的涂膜,可在转化成其亲水性形式时降低水的接触角。此种单体的一个实例为称作F-85的(3-氨基丙基甲基丙烯酰胺-N,N-二乙酸二乙酯)。
因为氨基相邻基团的效应,此水解反应在缓冲化的中性水中可容易地经由加热而进行。
本发明相对于现有技术的优点是,将疏水性的潜在亲水性形式的单体施加在模具表面后,可轻易地在相当疏水性的模具表面上形成均匀的薄膜。因为用于制造隐形眼镜的模具通常是用相当疏水性的聚合物制成的,例如聚苯乙烯或聚丙烯,所以很难使亲水性单体例如HEMA在模具表面上形成光滑连续的薄膜,因为此种亲水性单体容易形成珠滴或从模具表面剥离。将疏水性单体施加在疏水性基质上,可形成光滑连续的薄单体膜。例如使用典型相当疏水性的单体例如甲基丙烯酸甲酯或甲基丙烯酸月桂酯,可在模具表面上形成薄膜,但将通常导致具有疏水性、非可湿性表面的隐形眼镜。使用疏水性的潜在亲水性单体可在模具表面形成光滑连续的薄单体膜,然后可在温和的条件下,将所得相当疏水性的镜片涂膜转化成相当亲水性的可湿化镜片涂膜。
可在本发明中使用的潜在亲水性单体的非限定实例包括含有可聚合化官能基例如甲基丙烯酸基、丙烯酸基、苯乙烯基或乙烯基的单体,以及含非离子性官能基其可经由温和的化学反应条件转化成离子性官能基的单体。这些温和的反应条件是相较于严苛或强烈的反应条件例如使用大于pH9或低于pH5的强酸或强碱条件。合适的官能基的实例为氨基,可经由浸在中性或温和的酸性水溶液将其转化成铵基;α-氨基酸酯类的酯类,可在温和的水解条件下将其转化成离子性羧酸盐基;以及酰基氯和酸酐官能基,其也可在温和的水解条件下将其转化成离子性羧酸盐基;及羧酸官能基,可经由浸在中性或温和的碱性水溶液将其转化成羧酸盐基。据此可在本发明中使用的单体的特定但非限定实例,单独或混合下包括但不限于F-85及3-氨基丙基甲基丙烯酰胺-N,N-二乙酸、甲基丙烯酸、丙烯酸、衣康酸、甲基丙烯酸酐、丙烯酸酐、马来酸酐、甲基丙烯酰氯、丙烯酰氯、氨基丙基甲基丙烯酰胺及2-二甲氨基乙基甲基丙烯酸酯的二甲基、二正丙基、二异丙基、二丁基、二苄基及二苯基酯类。
交联的单体也可单独或混合地包括在用于涂布模具表面的单体掺合物中,包括二甲基丙烯酸乙二醇酯(EGDMA)。
聚合反应催化剂可包含在单体混合物中。聚合反应催化剂可为例如过氧化月桂酰、过氧化苯甲酰、过碳酸异丙酯、偶氮双异丁腈等可在适度升温下产生自由基的化合物,或聚合反应催化剂可为光引发剂***例如芳族α-羟基酮或叔胺加上二酮。光引发剂***的实例为2-羟基-2-甲基-1-苯基-丙-1-酮及樟脑醌与4-(N,N-二甲氨基)苯甲酸乙酯的混合物。催化剂可在有效催化剂量下用于涂料混合物中,例如每100份涂料单体混合物中从约0.1至约2.0重量份。
涂料单体混合物也可包括习知的反应性单体例如HEMA、N,N-二甲基丙烯酰胺、甲基丙烯酸甲酯及N-乙烯基吡咯烷酮。
涂料单体混合物也可包括挥发性或非挥发性的非反应性载剂或表面活性剂以促进应用,例如通过降低混合物的粘性或通过进一步改进涂料单体混合物在模具表面的湿性。这些可包括但不限于乙醇、甲醇、异丙醇、聚丙二醇、聚丁二醇、及聚氧乙烯山梨糖醇酐单月桂酸酯。
也适宜在应用至模具表面前,将一部分的潜在亲水性单体部分聚合而生成预聚物,以便增加单体混合物的粘性,进而改进在模具表面形成的膜的稳定性。
在本发明中使用的隐形眼镜塑膜包括但不限于聚丙烯、聚乙烯、金属、陶瓷或聚苯乙烯。
潜在亲水性单体混合物可用本领域技术人员所习知的几种涂布方法中的任一种施加在模具的内部表面,所述涂布方法包括但不限于喷雾法、转印法、浸渍法、或刷拂法。当使用挥发性的非反应性载剂例如异丙醇时,可使非反应性载剂在将形成镜片的单体混合物填入模具前先蒸发。涂布的单体混合物可经由加热或用UV光照射而固化,或在没有将涂膜预先固化下使用模具,如此使涂膜及本体镜片聚合物同时固化。
固体表面可湿性的测试是经由将样品浸入测试液中。当样品浸入液体或从液体拿出时,可分别得到前进角及后退角。决定于镜片上潜在亲水性涂膜在涂膜已经转化成其亲水性形式后的化学结构,本发明中的这些角度将随著变化。从实例1-10可看出对于前进角的这些角度通常在68°-115°之间变化。用相同的测量方法将其与相同组成但没有潜在亲水性单体涂膜的镜片比较。对于前进角的这些测量角度通常在128°-130°之间变化。当然角度的测量值愈高,可湿性愈低。
隐形眼镜本体的聚合物可选自包括相当疏水性的聚合物,包括但不限于交联的聚二甲基硅氧烷类、多氟化烷基官能基聚合物、或聚丙二醇类。这些聚合物的形成可经由缩合聚合反应例如异氰酸酯-醇反应、硅烷醇偶合反应或经由聚乙烯聚合反应,决定于选用的固化催化剂,反应可经由热、可见光或UV光引发。在本发明应用中的一种较佳单体为α,ω-双甲基丙烯酰氧基丙基聚二甲基硅氧烷:
其中n等于20-500,以约300较佳。
也可使用其他反应性聚二甲基硅氧烷单体以及含氟硅氧烷的单体及含聚硅氧烷与聚烯化氧嵌段的嵌段共聚物,以形成本体镜片聚合物。
经由在模具中使本体单体混合物与潜在亲水性涂膜聚合而形成涂布化的镜片后,将镜片从模具取出并暴露在足以将镜片表面上的潜在亲水性官能基转化成其亲水性形式的温和反应条件。当使用的潜在亲水性官能基为简单的酸性或碱性基团例如羧酸或胺官能基时,通常将镜片浸在足以造成该基团酸碱反应的水溶液一段时间,而将其转化成亲水性离子形式。因为眼睛环境的pH值大约7.3,使用前较宜将镜片浸在pH中性盐水溶液例如磷酸盐或硼酸盐缓冲化的盐水,通常历时10至100分钟。如果潜在亲水性单体为酸酐官能基或酰基氯官能基单体,通常必须在室温或加热下将镜片浸在水中1至20小时,才能将涂膜转化成其离子亲水性形式。对于此步骤的优选单体α-氨基羧酸酯类例如F-85,在温度约80至130℃下,将镜片在中性缓冲盐水中加热约1至20小时,通常足以将涂膜转化成其离子亲水性形式。用氨基官能基单体制成的镜片涂膜也可经由与溴代醋酸乙酯或氯代醋酸乙酯反应,随后将所得的α-氨基酯基团水解而产生亲水性离子羧酸盐基团,转化成离子形式;或用氨基官能基单体制成的镜片涂膜,可与卤代醋酸例如α-溴代醋酸或α-氯代醋酸反应而直接形成亲水性离子羧酸盐基团。
实施例1-制备涂布poly(F85)的硅酮镜片
将2.01克(11.3毫摩尔)APMA.HCl、3.73毫升(5.62克,33.7毫摩尔)溴代醋酸乙酯及3.56克(33.6毫摩尔)Na2CO3在122克乙腈中混合并在室温下搅拌24小时,过滤反应混合物,在过滤液中加入小粒晶体的氢醌单甲醚(HQMME,抑制剂),在减压下将溶剂蒸发而得到橙色液体。加入4%HCl水溶液直到混合物为酸性。用CH2Cl2萃取此溶液一次,用饱和的Na2CO3调成碱性,并再度用新的CH2Cl2萃取。CH2Cl2层经由固体Na2SO4干燥,用小粒晶体的HQMME抑制,旋转蒸发而得到1.64克产物的F-85,其为油状并有下列分析结果:1H NMR(CDCl3)1.22ppm(t,6H)、1.61(m,2H)、1.92(s,3H)、2.71(t,2H)、3.41(t,2H)、3.44(s,4H)、4.12(q,4H)、5.25(m,1H)、5.71(m,1H)、7.39(br s,1H);IR(纯质)3354、2980、2938、2870、1737、1661、1619、1619、1531、1196、1029cm-1。产物的HPLC显示一个主要的单峰,没有检测到残留的APMA或溴代醋酸乙酯。
将2.0份的F-85溶解在8.0份的异丙醇及0.02份的α-羟基-α,α-二甲基乙酰苯中。用尖端为海棉的拖把将此混合物以薄膜形式施加在聚苯乙烯隐形眼镜模具的整个内部表面。异丙醇蒸发后,将99份下列化学式的硅酮单体及1份1-羟基环己基苯基酮的混合物放入这些涂布化的聚苯乙烯隐形眼镜模具内。将模具封闭并用UV光照射(Philips萤光灯泡,129毫焦耳/厘米2*分钟)历时0.5小时。将所得的隐形眼镜从模具中取出,浸泡在异丙醇中1小时,然后浸泡在醋酸乙酯中1小时,用硼酸盐缓冲化的盐水溶液清洗,然后在硼酸盐缓冲化的盐水溶液中及在压热器内于121℃下加热7小时,使乙酯官能基水解。硼酸盐缓冲化的盐水溶液在此镜片上的前进角为71°,用相同方法制造但没有涂膜的镜片为128°。实施例2-制备涂布聚(甲基丙烯酸)的隐形眼镜
将15.58克聚丙二醇(分子量4000)及4.60克甲基丙烯酸、0.06克α-羟基-α,α-二甲基乙酰酮及0.05克EGDMA混合后的掺合物,用尖端为海棉的拖把将其以薄膜形式施加在聚苯乙烯隐形眼镜模具的整个内部表面。将99份双甲基丙烯酰氧基丙基硅酮单体及1份1-羟基环己基苯基酮的掺合物放入这些涂布化的聚苯乙烯隐形眼镜模具内。将模具封闭并用UV光照射(Philips萤光灯泡,129毫焦耳/厘米2*分钟)历时0.5小时。将所得的隐形眼镜从模具中取出,浸泡在异丙醇中1小时,然后浸泡在醋酸乙酯中1小时,用硼酸盐缓冲化的盐水溶液清洗并浸泡在硼酸盐缓冲化pH7的生理食盐水中。所得镜片的表面比用硅酮单体制造但没有经表面处理的镜片更可湿化。实施例3-制备涂布3-氨基丙基甲基丙烯酰胺-N,N-二醋酸二正丙酯的硅酮镜片
根据实施例1的步骤,从3-氨基丙基甲基丙烯酰胺及溴代醋酸正丙酯制备3-氨基丙基甲基丙烯酰胺-N,N-二醋酸二正丙酯。将油状的产物分离并得到下列分析结果:1H NMR(CDCl3)0.94ppm(t,6H)、1.67(m,6H)、1.97(s,3H)、2.77(t,2H)、3.47(t,2H)、3.51(s,4H)、4.07(t,4H)、5.30(m,1H)、5.76(m,1H)、7.40(br s,1H)。
用0.113克上述的油、0.09克异丙醇及0.02克α-羟基-α,α-二甲基乙酰苯的溶液涂布聚苯乙烯隐形眼镜模具。然后用实施例1的步骤制造镜片。硼酸盐缓冲化的盐水溶液在此镜片上的前进角为95°。实施例4-制备涂布3-氨基丙基甲基丙烯酰胺-N,N-二醋酸二异丙酯的硅酮镜片
根据实施例1的步骤,从3-氨基丙基甲基丙烯酰胺及溴代醋酸异丙酯制备3-氨基丙基甲基丙烯酰胺-N,N-二醋酸二异丙酯。将油状的产物分离并得到下列分析结果:1H NMR(CDCl3)1.24ppm(d,12H)、1.65(m,2H)、1.97(s,3H)、2.76(t,2H)、3.46(s,4H)、3.49(t,2H)、5.04(sep,2H)、5.29(m,1H)、5.76(m,1H)、7.48(br s,1H)。
用0.36克上述的油、0.23克异丙醇及0.02克α-羟基-α,α-二甲基乙酰苯的溶液涂布聚苯乙烯隐形眼镜模具。然后用实施例1的步骤制造镜片。硼酸盐缓冲化的盐水溶液在此镜片上的前进角为99°。实施例5-制备涂布甲基丙烯酸酐的硅酮镜片
将0.01克α-羟基-α,α-二甲基乙酰苯及1.03克甲基丙烯酸酐的掺合物以薄膜形式施加在聚苯乙烯隐形眼镜模具的整个内部表面。如实施例1所述方法在模具中填入硅酮单体及光引发剂的掺合物,经由UV引发的聚合反应形成镜片。将这些镜片从模具中取出,用醋酸乙酯清洗并在硼酸盐缓冲化的盐水溶液中,于121℃下加热7小时。硼酸盐缓冲化的盐水溶液在此镜片上的前进角为106°。实施例6-使用聚丙烯模具制备涂布F-85的镜片
将4份F-85、6份异丙醇及0.03份α-羟基-α,α-二甲基乙酰苯的溶液涂布在聚丙烯隐形眼镜模具内。用实施例1的步骤制造镜片。硼酸盐缓冲化的盐水溶液在此镜片上的前进角为41°。实施例7-在涂膜中没有光引发剂下制备涂布F-85的硅酮镜片
将2.0份F-85及8.0份异丙醇的溶液涂布在聚苯乙烯隐形眼镜模具内。用实施例1的步骤制造镜片。硼酸盐缓冲化的盐水溶液在此镜片上的前进角为89°。实施例8-在涂膜中加入交联剂下制备涂布F-85的硅酮镜片
将0.2克F-85、0.0033克二甲基丙烯酸乙二醇酯及0.8克异丙醇的溶液涂布在聚苯乙烯隐形眼镜模具内。然后用实施例1的步骤制造镜片。硼酸盐缓冲化的盐水溶液在此镜片上的前进角为68°。实施例9-制备涂布部分预先聚合化F-85的硅酮镜片
将20%F-85及1%α-羟基-α,α-二甲基乙酰苯在异丙醇中的掺合物用UV光照射4小时。将此掺合物涂布在聚苯乙烯模具内并根据实施例1的步骤制造镜片。硼酸盐缓冲化的盐水溶液在此镜片上的前进角为115°。实施例10-制备涂布部分预先聚合化F-85的聚丙二醇镜片
重复实施例9的步骤,但使用聚丙二醇(分子量4000)在未端羟基与甲基丙烯酸异氰酸根合乙酯反应以取代硅酮。硼酸盐缓冲化的盐水溶液在此镜片上的前进角为89°,用相同的本体聚合物制备但没有涂布的镜片为130°。
Claims (28)
1.一种模塑制品,其中含涂布潜在亲水性可聚合化物质的本体聚合物的物体。
2.根据权利要求1的模塑制品,其中本体聚合物为聚二甲基硅氧烷。
3.根据权利要求1的模塑制品,其中该潜在亲水性可聚合化物质含一种官能基,其在温和的反应条件下可化学性转化成更亲水性的官能基。
4.根据权利要求3的模塑制品,其中该潜在亲水性可聚合化物质为α-氨基羧酸酯。
5.根据权利要求3的模塑制品,其中该潜在亲水性可聚合化物质为3-氨基丙基甲基丙烯酰胺-N,N-二醋酸的二酯。
6.根据权利要求3的模塑制品,其中该潜在亲水性可聚合化物质为3-氨基丙基甲基丙烯酰胺-N,N-二醋酸二乙酯。
7.根据权利要求3的模塑制品,其中该潜在亲水性可聚合化物质为甲基丙烯酸。
8.根据权利要求1的模塑制品,其为软性隐形眼镜。
9.一种制备根据权利要求1的模塑制品的方法,其步骤包括:
(a)将一种潜在亲水性且正常为疏水性的可聚合化物质涂布在模
具的内部表面;
(b)在步骤(a)的涂布化的模具内填入可聚合成透氧性聚合物的单
体物质;
(c)将步骤(b)的模具固化而产生涂布化的模塑制品;及
(d)在足以将涂膜转化成亲水性形式的温和反应条件下,处理步
骤(c)的该涂布化模塑制品。
10.根据权利要求9的方法,其中该潜在亲水性可聚合化物质为α-氨基酸的羧酸酯。
11.根据权利要求9的方法,其中步骤(d)的反应条件包括将该制品在缓冲化的中性水溶液中,在20至130℃下加热1-20小时。
12.根据权利要求9的方法,其中该潜在亲水性可聚合化物质为3-氨基丙基甲基丙烯酰胺-N,N-二醋酸二乙酯。
13.根据权利要求9的方法,其中该潜在亲水性可聚合化物质为α-氨基羧酸酯。
14.根据权利要求9的方法,其中该潜在亲水性可聚合化物质为甲基丙烯酸。
15.根据权利要求9的方法,其中步骤(a)包括将载剂添加至潜在亲水性可聚合化物质。
16.根据权利要求15的方法,其中该载剂为异丙醇。
17.根据权利要求15的方法,其中该载剂为二元醇。
18.根据权利要求9的方法,其中步骤(c)是在UV聚合反应引发剂存在下完成的。
19.根据权利要求9的方法,其中模具是用聚丙烯制成的。
20.根据权利要求9的方法,其中该透氧性聚合物质为α,ω-双甲基丙烯酰氧基烷基聚二甲基硅氧烷。
21.根据权利要求9的方法,其中该透氧性聚合物质为聚丙二醇。
22.根据权利要求9的方法,其中步骤(b)的单体物质为多氟化烷基官能基单体。
23.根据权利要求9的方法,其中步骤(a)的涂布是经由将该潜在亲水性可聚合化物质喷雾在模具上而完成的。
24.根据权利要求9的方法,其中步骤(a)的涂布是经由将模具浸在潜在亲水性可聚合化物质中而完成的。
25.根据权利要求9的方法,其中步骤(a)的涂布是经由将该潜在亲水性可聚合化物质刷拂在模具上而完成的。
26.根据权利要求9的方法,其中该潜在亲水性可聚合化物质为一种预聚物。
27.根据权利要求9的方法,其中该模塑制品为隐形眼镜。
28.一种模塑制品,其中含涂布衍生自潜在亲水性可聚合化物质的涂膜的本体聚合物的物体。
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-
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- 1997-03-05 IL IL12038197A patent/IL120381A0/xx unknown
- 1997-03-12 AU AU16267/97A patent/AU722036B2/en not_active Ceased
- 1997-03-14 SG SG9700777A patent/SG80569A1/en unknown
- 1997-03-17 KR KR1019970008900A patent/KR970065609A/ko not_active Application Discontinuation
- 1997-03-17 CA CA002200146A patent/CA2200146C/en not_active Expired - Fee Related
- 1997-03-18 EP EP97301826A patent/EP0797110B1/en not_active Expired - Lifetime
- 1997-03-18 BR BR9701331A patent/BR9701331A/pt not_active Application Discontinuation
- 1997-03-18 AT AT97301826T patent/ATE241150T1/de not_active IP Right Cessation
- 1997-03-18 JP JP08343897A patent/JP4267086B2/ja not_active Expired - Fee Related
- 1997-03-18 NO NO971237A patent/NO971237L/no unknown
- 1997-03-18 ZA ZA972346A patent/ZA972346B/xx unknown
- 1997-03-18 DE DE69722066T patent/DE69722066T2/de not_active Expired - Lifetime
- 1997-03-19 CN CNB971045321A patent/CN100403059C/zh not_active Expired - Fee Related
Cited By (3)
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CN1317570C (zh) * | 2000-02-16 | 2007-05-23 | Zms有限责任公司 | 精确复合体制品 |
CN104924508A (zh) * | 2015-05-21 | 2015-09-23 | 东南大学 | 用于接触透镜的模具、整理方法及接触透镜的制作方法 |
CN104924508B (zh) * | 2015-05-21 | 2017-04-05 | 东南大学 | 用于接触透镜的模具、整理方法及接触透镜的制作方法 |
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AU722036B2 (en) | 2000-07-20 |
CA2200146C (en) | 2006-09-26 |
EP0797110A3 (en) | 1998-02-11 |
IL120381A0 (en) | 1997-07-13 |
JPH09263730A (ja) | 1997-10-07 |
KR970065609A (ko) | 1997-10-13 |
NO971237D0 (no) | 1997-03-18 |
ZA972346B (en) | 1998-09-21 |
CA2200146A1 (en) | 1997-09-19 |
EP0797110A2 (en) | 1997-09-24 |
ATE241150T1 (de) | 2003-06-15 |
DE69722066D1 (de) | 2003-06-26 |
JP4267086B2 (ja) | 2009-05-27 |
BR9701331A (pt) | 1998-11-10 |
US5779943A (en) | 1998-07-14 |
SG80569A1 (en) | 2001-05-22 |
EP0797110B1 (en) | 2003-05-21 |
NO971237L (no) | 1997-09-22 |
AU1626797A (en) | 1997-09-25 |
DE69722066T2 (de) | 2004-03-18 |
MX9702057A (es) | 1998-03-31 |
CN100403059C (zh) | 2008-07-16 |
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