IL91711A - Molded polymers with hydrophilic surfaces and process for making them - Google Patents

Molded polymers with hydrophilic surfaces and process for making them

Info

Publication number: IL91711A
Authority: IL; Israel
Prior art keywords: polymer; vinyl; methacrylate; product according; poly
Prior art date: 1988-09-28

Application number

IL9171189A

Other languages

English (en)

Other versions

IL91711A0 (en

Original Assignee

Ciba Geigy Ag

Priority date (The priority date 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 date listed.)

1988-09-28

Filing date

1989-09-21

Publication date

1994-06-24

1989-09-21 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1990-06-10 Publication of IL91711A0 publication Critical patent/IL91711A0/xx

1994-06-24 Publication of IL91711A publication Critical patent/IL91711A/en

Links

229920000642 polymer Polymers 0.000 title claims abstract description 206
238000000034 method Methods 0.000 title claims abstract description 60
230000008569 process Effects 0.000 title claims abstract description 32
230000005660 hydrophilic surface Effects 0.000 title abstract description 6
239000000178 monomer Substances 0.000 claims abstract description 59
229920001477 hydrophilic polymer Polymers 0.000 claims abstract description 25
230000000379 polymerizing effect Effects 0.000 claims abstract description 12
-1 poly(vinyl alcohol) Polymers 0.000 claims description 76
229920002554 vinyl polymer Polymers 0.000 claims description 66
229920002451 polyvinyl alcohol Polymers 0.000 claims description 53
239000004814 polyurethane Substances 0.000 claims description 48
238000000576 coating method Methods 0.000 claims description 47
239000000203 mixture Substances 0.000 claims description 46
229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 43
239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 43
235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 43
229920002635 polyurethane Polymers 0.000 claims description 43
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 43
239000004372 Polyvinyl alcohol Substances 0.000 claims description 42
229920001600 hydrophobic polymer Polymers 0.000 claims description 38
229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 37
238000006243 chemical reaction Methods 0.000 claims description 33
CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 33
239000011248 coating agent Substances 0.000 claims description 32
229920001577 copolymer Polymers 0.000 claims description 32
RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 claims description 32
238000006116 polymerization reaction Methods 0.000 claims description 28
150000002009 diols Chemical group 0.000 claims description 23
229920002379 silicone rubber Polymers 0.000 claims description 20
239000012948 isocyanate Substances 0.000 claims description 19
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 18
150000002513 isocyanates Chemical class 0.000 claims description 17
239000004945 silicone rubber Substances 0.000 claims description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
229920002396 Polyurea Polymers 0.000 claims description 15
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 14
239000004205 dimethyl polysiloxane Substances 0.000 claims description 13
229920000728 polyester Polymers 0.000 claims description 13
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 12
229920000307 polymer substrate Polymers 0.000 claims description 12
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 11
229910052731 fluorine Inorganic materials 0.000 claims description 11
239000011737 fluorine Substances 0.000 claims description 11
125000000524 functional group Chemical group 0.000 claims description 11
125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 11
229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 11
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 10
229920000570 polyether Polymers 0.000 claims description 10
229920002678 cellulose Polymers 0.000 claims description 9
239000001913 cellulose Substances 0.000 claims description 9
235000013870 dimethyl polysiloxane Nutrition 0.000 claims description 9
229920013821 hydroxy alkyl cellulose Polymers 0.000 claims description 9
229920000647 polyepoxide Polymers 0.000 claims description 9
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
150000001252 acrylic acid derivatives Chemical class 0.000 claims description 8
238000007334 copolymerization reaction Methods 0.000 claims description 8
239000003822 epoxy resin Substances 0.000 claims description 8
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 7
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 7
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 7
239000004721 Polyphenylene oxide Substances 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 7
VSSGDAWBDKMCMI-UHFFFAOYSA-N 2-methyl-2-(2-methylprop-2-enoylamino)propane-1-sulfonic acid Chemical compound CC(=C)C(=O)NC(C)(C)CS(O)(=O)=O VSSGDAWBDKMCMI-UHFFFAOYSA-N 0.000 claims description 6
239000004952 Polyamide Substances 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 6
229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 claims description 6
229920002647 polyamide Polymers 0.000 claims description 6
239000004642 Polyimide Substances 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
229920001721 polyimide Polymers 0.000 claims description 5
230000005855 radiation Effects 0.000 claims description 5
150000003254 radicals Chemical class 0.000 claims description 5
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 4
150000003926 acrylamides Chemical class 0.000 claims description 4
150000001408 amides Chemical class 0.000 claims description 4
GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
150000002148 esters Chemical group 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical group C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 claims description 4
229920003226 polyurethane urea Polymers 0.000 claims description 4
MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 3
229920001519 homopolymer Polymers 0.000 claims description 3
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 3
229920006295 polythiol Polymers 0.000 claims description 3
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 2
ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical group OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 claims description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 claims description 2
150000003951 lactams Chemical group 0.000 claims description 2
150000002688 maleic acid derivatives Chemical class 0.000 claims description 2
229920001567 vinyl ester resin Polymers 0.000 claims description 2
229920003169 water-soluble polymer Polymers 0.000 claims description 2
229940095095 2-hydroxyethyl acrylate Drugs 0.000 claims 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 claims 1
229910052708 sodium Inorganic materials 0.000 claims 1
239000011734 sodium Substances 0.000 claims 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
230000002209 hydrophobic effect Effects 0.000 abstract description 24
230000000903 blocking effect Effects 0.000 abstract description 14
239000000758 substrate Substances 0.000 abstract description 13
239000002131 composite material Substances 0.000 abstract description 8
239000002904 solvent Substances 0.000 abstract description 8
229920001971 elastomer Polymers 0.000 abstract description 6
239000012528 membrane Substances 0.000 abstract description 4
239000002689 soil Substances 0.000 abstract description 2
239000000560 biocompatible material Substances 0.000 abstract 1
239000000806 elastomer Substances 0.000 abstract 1
229910001868 water Inorganic materials 0.000 description 49
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
239000000243 solution Substances 0.000 description 38
235000019422 polyvinyl alcohol Nutrition 0.000 description 37
230000015572 biosynthetic process Effects 0.000 description 35
229940071826 hydroxyethyl cellulose Drugs 0.000 description 32
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
229940063557 methacrylate Drugs 0.000 description 29
239000000047 product Substances 0.000 description 29
229920002799 BoPET Polymers 0.000 description 28
239000005041 Mylar™ Substances 0.000 description 28
238000003786 synthesis reaction Methods 0.000 description 25
229920001296 polysiloxane Polymers 0.000 description 24
239000010408 film Substances 0.000 description 23
WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 description 19
229910052757 nitrogen Inorganic materials 0.000 description 18
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
229940088644 n,n-dimethylacrylamide Drugs 0.000 description 15
YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 14
229940044192 2-hydroxyethyl methacrylate Drugs 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 12
238000005266 casting Methods 0.000 description 12
239000012975 dibutyltin dilaurate Substances 0.000 description 12
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 11
229940063559 methacrylic acid Drugs 0.000 description 11
238000005299 abrasion Methods 0.000 description 10
239000003054 catalyst Substances 0.000 description 10
238000001723 curing Methods 0.000 description 10
BEWCNXNIQCLWHP-UHFFFAOYSA-N 2-(tert-butylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(C)(C)C BEWCNXNIQCLWHP-UHFFFAOYSA-N 0.000 description 9
239000000463 material Substances 0.000 description 9
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 8
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 8
GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 8
238000010521 absorption reaction Methods 0.000 description 8
235000010980 cellulose Nutrition 0.000 description 8
229920000058 polyacrylate Polymers 0.000 description 8
239000007787 solid Substances 0.000 description 8
SLBOQBILGNEPEB-UHFFFAOYSA-N 1-chloroprop-2-enylbenzene Chemical compound C=CC(Cl)C1=CC=CC=C1 SLBOQBILGNEPEB-UHFFFAOYSA-N 0.000 description 7
BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 7
DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 7
238000004566 IR spectroscopy Methods 0.000 description 7
239000005058 Isophorone diisocyanate Substances 0.000 description 7
STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 7
239000011521 glass Substances 0.000 description 7
239000003999 initiator Substances 0.000 description 7
NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 7
238000003756 stirring Methods 0.000 description 7
238000012360 testing method Methods 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
239000004743 Polypropylene Substances 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
229920003023 plastic Polymers 0.000 description 6
239000004033 plastic Substances 0.000 description 6
229920001282 polysaccharide Polymers 0.000 description 6
238000012546 transfer Methods 0.000 description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
238000001035 drying Methods 0.000 description 5
229920000578 graft copolymer Polymers 0.000 description 5
229940044600 maleic anhydride Drugs 0.000 description 5
229940032007 methylethyl ketone Drugs 0.000 description 5
PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 5
239000001301 oxygen Substances 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
229920001223 polyethylene glycol Polymers 0.000 description 5
229920001155 polypropylene Polymers 0.000 description 5
229920013730 reactive polymer Polymers 0.000 description 5
239000005060 rubber Substances 0.000 description 5
239000002002 slurry Substances 0.000 description 5
239000004094 surface-active agent Substances 0.000 description 5
229940035024 thioglycerol Drugs 0.000 description 5
FMQPBWHSNCRVQJ-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C(F)(F)F)C(F)(F)F FMQPBWHSNCRVQJ-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000000835 fiber Substances 0.000 description 4
150000004676 glycans Chemical class 0.000 description 4
239000001814 pectin Substances 0.000 description 4
235000010987 pectin Nutrition 0.000 description 4
229920001277 pectin Polymers 0.000 description 4
229920001451 polypropylene glycol Polymers 0.000 description 4
239000005017 polysaccharide Substances 0.000 description 4
238000005956 quaternization reaction Methods 0.000 description 4
239000002344 surface layer Substances 0.000 description 4
238000006276 transfer reaction Methods 0.000 description 4
229940086542 triethylamine Drugs 0.000 description 4
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
239000000080 wetting agent Substances 0.000 description 4
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
229920002307 Dextran Polymers 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 3
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000007975 buffered saline Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
238000000151 deposition Methods 0.000 description 3
125000005442 diisocyanate group Chemical group 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000007789 gas Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000001863 hydroxypropyl cellulose Substances 0.000 description 3
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 3
238000007654 immersion Methods 0.000 description 3
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
238000005259 measurement Methods 0.000 description 3
238000012986 modification Methods 0.000 description 3
238000004987 plasma desorption mass spectroscopy Methods 0.000 description 3
238000006068 polycondensation reaction Methods 0.000 description 3
229920006254 polymer film Polymers 0.000 description 3
229920000193 polymethacrylate Polymers 0.000 description 3
150000003077 polyols Chemical class 0.000 description 3
239000000376 reactant Substances 0.000 description 3
238000010345 tape casting Methods 0.000 description 3
APAUNQLFVGBQQW-UHFFFAOYSA-N (1,2,2-trimethylcyclohexyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1(C)CCCCC1(C)C APAUNQLFVGBQQW-UHFFFAOYSA-N 0.000 description 2
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 2
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-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
HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical group COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 description 2
KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
BESKSSIEODQWBP-UHFFFAOYSA-N 3-tris(trimethylsilyloxy)silylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C BESKSSIEODQWBP-UHFFFAOYSA-N 0.000 description 2
WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
229920000974 Poly(dimethylsiloxane-ethylene oxide) Polymers 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
229920006311 Urethane elastomer Polymers 0.000 description 2
WDRCWISGZGOZPY-UHFFFAOYSA-N [dihydroxy(methyl)silyl]oxy-[dimethyl(trimethylsilyloxy)silyl]oxy-dimethylsilane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(O)O WDRCWISGZGOZPY-UHFFFAOYSA-N 0.000 description 2
238000007792 addition Methods 0.000 description 2
230000032683 aging Effects 0.000 description 2
238000007605 air drying Methods 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
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Classifications

- 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
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- 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
- B29C41/003—Shaping by coating a mould, core or other substrate, i.e. by depositing material and stripping-off the shaped article; Apparatus therefor characterised by the choice of material
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/05—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur
- C08B15/06—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur containing nitrogen, e.g. carbamates
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/10—Polymers provided for in subclass C08B
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- 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

Landscapes

Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Physics & Mathematics (AREA)
Materials Engineering (AREA)
General Physics & Mathematics (AREA)
Optics & Photonics (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Mechanical Engineering (AREA)
Manufacturing & Machinery (AREA)
Graft Or Block Polymers (AREA)
Macromonomer-Based Addition Polymer (AREA)
Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
Eyeglasses (AREA)
Treatments Of Macromolecular Shaped Articles (AREA)
Laminated Bodies (AREA)
Casting Or Compression Moulding Of Plastics Or The Like (AREA)
Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)

IL9171189A 1988-09-28 1989-09-21 Molded polymers with hydrophilic surfaces and process for making them IL91711A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US25019988A	1988-09-28	1988-09-28

Publications (2)

Publication Number	Publication Date
IL91711A0 IL91711A0 (en)	1990-06-10
IL91711A true IL91711A (en)	1994-06-24

Family

ID=22946710

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9171189A IL91711A (en)	1988-09-28	1989-09-21	Molded polymers with hydrophilic surfaces and process for making them

Country Status (11)

Country	Link
EP (1)	EP0362137A3 (fr)
JP (1)	JPH02124523A (fr)
AR (1)	AR245465A1 (fr)
AU (1)	AU624178B2 (fr)
BR (1)	BR8904890A (fr)
CA (1)	CA1323739C (fr)
DK (1)	DK475789A (fr)
IL (1)	IL91711A (fr)
MX (1)	MX174098B (fr)
PT (1)	PT91801B (fr)
ZA (1)	ZA897344B (fr)

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US6310116B1 (en) *	1997-10-09	2001-10-30	Kuraray Co., Ltd.	Molded polymer article having a hydrophilic surface and process for producing the same
US6500481B1 (en)	1998-06-11	2002-12-31	Johnson & Johnson Vision Care, Inc.	Biomedical devices with amid-containing coatings
US6893595B1 (en) *	1998-07-17	2005-05-17	Biocompatibles Uk Limited	Method for providing coated moulded polymeric articles
CA2374241A1 (fr)	1999-06-11	2000-12-21	Bausch & Lomb Incorporated	Moules pour lentilles a revetements protecteurs destines a la production de lentilles de contact et d'autre articles ophtalmologiques
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US6478423B1 (en)	1999-10-12	2002-11-12	Johnson & Johnson Vison Care, Inc.	Contact lens coating selection and manufacturing process
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JP2002182166A (ja) *	2000-12-11	2002-06-26	Toray Ind Inc	プラスチック成形品およびそれからなるコンタクトレンズ
JP4854130B2 (ja) *	2001-05-01	2012-01-18	クーパーヴィジョンインターナショナルホウルディングカンパニーリミテッドパートナーシップ	親水性ポリシロキサンモノマーおよびその共重合体からなるコンタクトレンズ材料、およびコンタクトレンズ
JP4909469B2 (ja)	2001-06-25	2012-04-04	株式会社メニコン	眼用レンズおよびその製造方法
US7879267B2 (en)	2001-08-02	2011-02-01	J&J Vision Care, Inc.	Method for coating articles by mold transfer
US7485672B2 (en)	2001-08-02	2009-02-03	Johnson & Johnson Vision Care, Inc.	Process for the synthesis of soluble, high molecular weight polymers
US7816446B2 (en)	2004-10-01	2010-10-19	Illinois Institute Of Technology	Interpenetrated rubber particles and compositions including the same
JP4614271B2 (ja) *	2004-12-27	2011-01-19	Ｈｏｙａ株式会社	複合コンタクトレンズ及びレンズ素材の製造方法
MX2008011877A (es)	2006-03-20	2008-11-28	Coopervision Int Holding Co Lp	Auxiliares para desprendimiento de moldes de hidrogeles de silicona y metodos relacionados.
US7858000B2 (en) *	2006-06-08	2010-12-28	Novartis Ag	Method of making silicone hydrogel contact lenses
US8262952B2 (en)	2007-10-31	2012-09-11	Bausch & Lomb Incorporated	Molds for production of ophthalmic devices
US8480227B2 (en)	2010-07-30	2013-07-09	Novartis Ag	Silicone hydrogel lenses with water-rich surfaces
HUE029018T2 (en)	2011-10-12	2017-02-28	Novartis Ag	A method for producing UV absorbing contact lenses by coating
WO2013074535A1 (fr) *	2011-11-15	2013-05-23	Novartis Ag	Lentille en silicone hydrogel recouverte d'un revêtement hydrophile réticulé
HUE031702T2 (en)	2012-12-17	2017-07-28	Novartis Ag	A method for producing improved UV absorbing ophthalmic lenses
HUE038809T2 (hu)	2013-12-17	2018-11-28	Novartis Ag	Térhálósított hidrofíl bevonattal ellátott szilikon hidrogél lencse
MY183678A (en)	2014-08-26	2021-03-08	Alcon Inc	Method for applying stable coating on silicone hydrogel contact lenses
KR102604468B1 (ko)	2015-12-15	2023-11-22	알콘 인코포레이티드	실리콘 하이드로겔 콘택트 렌즈 상에 안정한 코팅을 적용하기 위한 방법
US10139521B2 (en) *	2016-04-20	2018-11-27	Coopervision International Holding Company, Lp	Silicone elastomer-hydrogel hybrid contact lenses
AU2017252594B2 (en) *	2016-04-20	2019-01-24	Coopervision International Limited	Silicone elastomer-silicone hydrogel hybrid contact lenses
TWI640557B (zh)	2017-07-05	2018-11-11	晶碩光學股份有限公司	具表面修飾的隱形眼鏡及其製備方法
CN117492228A (zh)	2017-12-13	2024-02-02	爱尔康公司	周抛和月抛水梯度接触镜片
JP6842435B2 (ja) *	2018-02-19	2021-03-17	信越化学工業株式会社	ラジカル硬化性オルガノシロキサングラフトポリビニルアルコール系重合体及びその製造方法
JP7226492B2 (ja) *	2020-09-03	2023-02-21	荒川化学工業株式会社	化合物、活性エネルギー線硬化型コーティング剤組成物、離型コーティング剤組成物、積層体、及び積層体の製造方法
CN112321732B (zh) *	2020-10-26	2023-03-10	衢州学院	一种疏水改性纤维素及其制备方法
JP7468699B2 (ja) *	2021-11-09	2024-04-16	東レ株式会社	ポリジメチルアクリルアミド粉体、ポリジメチルアクリルアミド溶液およびポリジメチルアクリルアミド粉体の製造方法

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US4099859A (en) *	1974-12-02	1978-07-11	High Voltage Engineering Corporation	Contact lens having a smooth surface layer of a hydrophilic polymer
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1989
- 1989-09-20 EP EP19890810712 patent/EP0362137A3/fr not_active Withdrawn
- 1989-09-21 AU AU41725/89A patent/AU624178B2/en not_active Ceased
- 1989-09-21 IL IL9171189A patent/IL91711A/en not_active IP Right Cessation
- 1989-09-25 CA CA000612794A patent/CA1323739C/fr not_active Expired - Fee Related
- 1989-09-26 PT PT91801A patent/PT91801B/pt not_active IP Right Cessation
- 1989-09-26 MX MX017691A patent/MX174098B/es unknown
- 1989-09-26 AR AR89315009A patent/AR245465A1/es active
- 1989-09-27 ZA ZA897344A patent/ZA897344B/xx unknown
- 1989-09-27 BR BR898904890A patent/BR8904890A/pt not_active Application Discontinuation
- 1989-09-27 DK DK475789A patent/DK475789A/da not_active Application Discontinuation
- 1989-09-28 JP JP1250808A patent/JPH02124523A/ja active Pending

Also Published As

Publication number	Publication date
AU624178B2 (en)	1992-06-04
CA1323739C (fr)	1993-11-02
PT91801A (pt)	1990-03-30
MX17691A (es)	1993-10-01
JPH02124523A (ja)	1990-05-11
AU4172589A (en)	1990-04-05
DK475789A (da)	1990-03-29
EP0362137A2 (fr)	1990-04-04
DK475789D0 (da)	1989-09-27
PT91801B (pt)	1995-05-31
MX174098B (es)	1994-04-21
EP0362137A3 (fr)	1991-09-04
BR8904890A (pt)	1990-05-08
IL91711A0 (en)	1990-06-10
ZA897344B (en)	1990-06-27
AR245465A1 (es)	1994-01-31

Legal Events

Date	Code	Title	Description
1996-07-23	RH	Patent void

Publication	Publication Date	Title
AU624178B2 (en)	1992-06-04	Molded polymers with hydrophilic surfaces, and process for making them
US5807944A (en)	1998-09-15	Amphiphilic, segmented copolymer of controlled morphology and ophthalmic devices including contact lenses made therefrom
KR100191144B1 (ko)	1999-06-15	표면-활성 매크로단량체
JP3172179B2 (ja)	2001-06-04	ポリマー物質の表面被覆
EP1266246B1 (fr)	2004-06-02	Prepolymeres reticulables ou polymerisables
US8703875B2 (en)	2014-04-22	Polymers
DK169764B1 (da)	1995-02-20	Umættede polysiloxaner samt deres anvendelse, især til fremstilling af kontaktlinser
US4983702A (en)	1991-01-08	Crosslinked siloxane-urethane polymer contact lens
EP0675910B1 (fr)	1997-09-17	Nouveaux macromonomeres
CA2630854C (fr)	2016-01-26	Methode de preparation d'hydrogels de silicone
US5177165A (en)	1993-01-05	Surface-active macromonomers
US5210111A (en)	1993-05-11	Crosslinked hydrogels derived from hydrophilic polymer backbones
EP0493320B1 (fr)	1996-07-31	Copolymères bloc poly(alkylène-oxyde) contenant du fluor et/ou du silicone et lentilles de contact
WO1997049740A9 (fr)	1998-04-30	Copolymere amphiphile segmente a morphologie controlee et dispositifs ophtalmiques tels que lentilles de contact fabriques a partir de ce dernier
JP2003512513A (ja)	2003-04-02	コーティング方法
JPH06503373A (ja)	1994-04-14	ポリマー物質の表面改変
JP2002284828A (ja)	2002-10-03	酸素透過性を改良した硬質コンタクトレンズ
CA2560228C (fr)	2013-05-21	Hydrogels de silicone pouvant etre tailles a temperature ambiante
JPS63297411A (ja)	1988-12-05	ポリビニル末端官能性マクロマー、そのポリマー及びそれから製造されるコンタクトレンズ
HK1001590B (en)	1998-06-26	Novel macromonomers