JP4616473B2 - 架橋結合可能なポリ尿素ポリマー類 - Google Patents
架橋結合可能なポリ尿素ポリマー類 Download PDFInfo
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- JP4616473B2 JP4616473B2 JP2000511800A JP2000511800A JP4616473B2 JP 4616473 B2 JP4616473 B2 JP 4616473B2 JP 2000511800 A JP2000511800 A JP 2000511800A JP 2000511800 A JP2000511800 A JP 2000511800A JP 4616473 B2 JP4616473 B2 JP 4616473B2
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- 229920000642 polymer Polymers 0.000 title claims description 21
- 229920002396 Polyurea Polymers 0.000 title description 7
- 239000001257 hydrogen Substances 0.000 claims description 69
- 229910052739 hydrogen Inorganic materials 0.000 claims description 69
- 125000002947 alkylene group Chemical group 0.000 claims description 64
- 150000001875 compounds Chemical class 0.000 claims description 63
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 45
- 239000013256 coordination polymer Substances 0.000 claims description 38
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 36
- 229920002554 vinyl polymer Polymers 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 229920001577 copolymer Polymers 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 239000012634 fragment Substances 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 238000004132 cross linking Methods 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 12
- 238000000108 ultra-filtration Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 10
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 9
- 125000005442 diisocyanate group Chemical group 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical group CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 claims description 7
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- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- WJIOHMVWGVGWJW-UHFFFAOYSA-N 3-methyl-n-[4-[(3-methylpyrazole-1-carbonyl)amino]butyl]pyrazole-1-carboxamide Chemical compound N1=C(C)C=CN1C(=O)NCCCCNC(=O)N1N=C(C)C=C1 WJIOHMVWGVGWJW-UHFFFAOYSA-N 0.000 claims description 5
- 150000002430 hydrocarbons Chemical group 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 3
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 3
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- PSABUFWDVWCFDP-UHFFFAOYSA-N 2,2-dimethylheptane Chemical compound CCCCCC(C)(C)C PSABUFWDVWCFDP-UHFFFAOYSA-N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- -1 1,3-propylene Chemical group 0.000 description 47
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- 238000006243 chemical reaction Methods 0.000 description 15
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 230000002209 hydrophobic effect Effects 0.000 description 10
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 125000000732 arylene group Chemical group 0.000 description 8
- 238000000605 extraction Methods 0.000 description 8
- 238000000465 moulding Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
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- 238000000746 purification Methods 0.000 description 8
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- 239000000178 monomer Substances 0.000 description 7
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000002993 cycloalkylene group Chemical group 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- 239000012266 salt solution Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 230000036571 hydration Effects 0.000 description 5
- 238000006703 hydration reaction Methods 0.000 description 5
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000003827 glycol group Chemical group 0.000 description 4
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000005250 alkyl acrylate group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
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- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
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- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
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- 125000003282 alkyl amino group Chemical group 0.000 description 2
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- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 2
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- 239000012442 inert solvent Substances 0.000 description 2
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
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- 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 1
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- 125000005838 1,3-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:2])C([H])([H])C1([H])[*:1] 0.000 description 1
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
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- UDJZTGMLYITLIQ-UHFFFAOYSA-N 1-ethenylpyrrolidine Chemical compound C=CN1CCCC1 UDJZTGMLYITLIQ-UHFFFAOYSA-N 0.000 description 1
- VOCDJQSAMZARGX-UHFFFAOYSA-N 1-ethenylpyrrolidine-2,5-dione Chemical compound C=CN1C(=O)CCC1=O VOCDJQSAMZARGX-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- QTKPMCIBUROOGY-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(F)(F)F QTKPMCIBUROOGY-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- MFGALGYVFGDXIX-UHFFFAOYSA-N 2,3-Dimethylmaleic anhydride Chemical compound CC1=C(C)C(=O)OC1=O MFGALGYVFGDXIX-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
- C08G18/6685—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3225 or polyamines of C08G18/38
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
- C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/81—Unsaturated isocyanates or isothiocyanates
- C08G18/8141—Unsaturated isocyanates or isothiocyanates masked
- C08G18/815—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/903—Interpenetrating network
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Eyeglasses (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polyamides (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97810666.4 | 1997-09-16 | ||
| EP97810666 | 1997-09-16 | ||
| PCT/EP1998/005826 WO1999014253A1 (en) | 1997-09-16 | 1998-09-14 | Crosslinkable polyurea polymers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001516778A JP2001516778A (ja) | 2001-10-02 |
| JP2001516778A5 JP2001516778A5 (https=) | 2006-01-05 |
| JP4616473B2 true JP4616473B2 (ja) | 2011-01-19 |
Family
ID=8230382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000511800A Expired - Fee Related JP4616473B2 (ja) | 1997-09-16 | 1998-09-14 | 架橋結合可能なポリ尿素ポリマー類 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6479587B1 (https=) |
| EP (1) | EP1017734B1 (https=) |
| JP (1) | JP4616473B2 (https=) |
| AR (1) | AR017108A1 (https=) |
| AU (1) | AU9743298A (https=) |
| DE (1) | DE69807509T2 (https=) |
| WO (1) | WO1999014253A1 (https=) |
| ZA (1) | ZA988420B (https=) |
Families Citing this family (83)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0971004A1 (en) * | 1998-07-06 | 2000-01-12 | Dsm N.V. | Powder paint binder composition |
| US7998412B2 (en) * | 2000-01-07 | 2011-08-16 | Smart Holograms Limited | Ophthalmic device comprising a holographic sensor |
| US7429465B2 (en) | 2002-09-13 | 2008-09-30 | Novartis Ag | Process for analyzing tear fluid |
| US7244394B2 (en) | 2002-10-03 | 2007-07-17 | Novartis Ag | Methods and kits for assays of analytes of interest in tears |
| US20050085585A1 (en) | 2002-10-23 | 2005-04-21 | Quinn Michael H. | Polymerizable materials |
| WO2005000109A2 (en) * | 2003-06-27 | 2005-01-06 | University Of Maryland Biotechnology Institute | Quaternary nitrogen heterocyclic compounds for detecting aqueous monosaccharides in physiological fluids |
| EP1651946A1 (en) * | 2003-07-30 | 2006-05-03 | Novartis AG | Reflection hologram sensor in contact lens |
| DE602004028020D1 (de) * | 2003-08-07 | 2010-08-19 | Eyesense Ag | Ophthalmischer sensor |
| US20050056954A1 (en) * | 2003-09-12 | 2005-03-17 | Devlin Brian Gerrard | Method for making contact lenses |
| US7151148B2 (en) * | 2003-09-16 | 2006-12-19 | Acushnet Company | Castable golf ball components using acrylate functional resins |
| US7977430B2 (en) | 2003-11-25 | 2011-07-12 | Novartis Ag | Crosslinkable polyurea prepolymers |
| US20060065138A1 (en) * | 2004-09-30 | 2006-03-30 | Tucker Robert C | Pad printing method for making colored contact lenses |
| WO2006053777A1 (en) * | 2004-11-22 | 2006-05-26 | Novartis Ag | Crosslinkable poly(oxyalkylene)-containing polyamide prepolymers |
| US7795359B2 (en) | 2005-03-04 | 2010-09-14 | Novartis Ag | Continuous process for production of polymeric materials |
| US9804295B2 (en) | 2005-05-05 | 2017-10-31 | Novartis Ag | Ophthalmic devices for sustained delivery of active compounds |
| US7905868B2 (en) | 2006-08-23 | 2011-03-15 | Medtronic Minimed, Inc. | Infusion medium delivery device and method with drive device for driving plunger in reservoir |
| US20070037897A1 (en) * | 2005-08-12 | 2007-02-15 | Guigui Wang | Method for making contact lenses |
| US7858000B2 (en) | 2006-06-08 | 2010-12-28 | Novartis Ag | Method of making silicone hydrogel contact lenses |
| PT2038310E (pt) | 2006-07-12 | 2010-08-25 | Novartis Ag | Copolímeros reticuláveis por via actínica para o fabrico de lentes de contacto |
| AR063561A1 (es) * | 2006-11-06 | 2009-02-04 | Novartis Ag | Dispositivos oculares y metodos para fabricar y utilizar los mismos |
| AR064286A1 (es) | 2006-12-13 | 2009-03-25 | Quiceno Gomez Alexandra Lorena | Produccion de dispositivos oftalmicos basados en la polimerizacion por crecimiento escalonado fotoinducida |
| KR101482808B1 (ko) | 2007-03-22 | 2015-01-14 | 노파르티스 아게 | 현수 폴리실록산-함유 중합체 사슬이 있는 예비중합체 |
| EP2146760B1 (en) | 2007-04-30 | 2018-10-10 | Medtronic MiniMed, Inc. | Reservoir filling, bubble management, and infusion medium delivery systems and methods with same |
| US7963954B2 (en) | 2007-04-30 | 2011-06-21 | Medtronic Minimed, Inc. | Automated filling systems and methods |
| TWI551305B (zh) | 2007-08-31 | 2016-10-01 | 諾華公司 | 相對黏稠封裝溶液之用途 |
| US7780879B2 (en) | 2007-12-20 | 2010-08-24 | Novartis Ag | Method for making contact lenses |
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| CA2760747C (en) | 2009-05-22 | 2016-12-13 | Novartis Ag | Actinically-crosslinkable siloxane-containing copolymers |
| MY158359A (en) | 2009-09-15 | 2016-09-30 | Novartis Ag | Prepolymers suitable for making ultra-violet absorbing contact lenses |
| JP6338856B2 (ja) | 2010-07-29 | 2018-06-06 | ノバルティス アーゲー | 着色コンタクトレンズ及びそれを製造する方法 |
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| CA2813469C (en) | 2010-10-06 | 2016-01-12 | Novartis Ag | Polymerizable chain-extended polysiloxanes with pendant hydrophilic groups |
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| US10160141B2 (en) | 2014-11-25 | 2018-12-25 | Novartis Ag | Molds for making contact lenses |
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| CN108367517A (zh) | 2015-12-15 | 2018-08-03 | 诺华股份有限公司 | 用于生产具有润滑表面的接触镜片的方法 |
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| CA3055265C (en) | 2017-04-13 | 2023-12-19 | Novartis Ag | Colored contact lenses and method of making the same |
| US10156736B2 (en) | 2017-04-13 | 2018-12-18 | Novartis Ag | Colored contact lenses and method of making the same |
| US10809181B2 (en) | 2017-08-24 | 2020-10-20 | Alcon Inc. | Method and apparatus for determining a coefficient of friction at a test site on a surface of a contact lens |
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| CA3083649A1 (en) | 2017-12-11 | 2019-06-20 | Innovative Surface Technologies, Inc. | Polyurea copolymer coating compositions and methods |
| 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 |
| HUE059157T2 (hu) | 2018-01-22 | 2022-10-28 | Alcon Inc | Formaöntéses eljárás UV-t elnyelõ kontaktlencse elõállítására |
| WO2020100090A1 (en) | 2018-11-15 | 2020-05-22 | Alcon Inc. | Contact lens with phosphorylcholine-modified polyvinylalcohols therein |
| WO2020208576A1 (en) | 2019-04-10 | 2020-10-15 | Alcon Inc. | Method for producing coated contact lenses |
| MY206069A (en) | 2019-05-28 | 2024-11-27 | Alcon Inc | Pad transfer printing method for making colored contact lenses |
| US20210271109A1 (en) | 2019-12-19 | 2021-09-02 | Alcon Inc. | Cosmetic contact lens for color blindness |
| US20240216823A1 (en) | 2020-04-28 | 2024-07-04 | Diamant Toys Ltd | Gaming kits and methods of playing with housings reconfigurable by retrievable unlocking elements |
| EP4240578B1 (en) | 2020-11-04 | 2024-12-18 | Alcon Inc. | Method for making photochromic contact lenses |
| HUE069913T2 (hu) | 2020-11-04 | 2025-04-28 | Alcon Inc | Eljárás fotokróm kontaktlencsék elõállítására |
| EP4304842B1 (en) | 2021-03-08 | 2026-05-06 | Alcon Inc. | Method for making photofunctional contact lenses |
| HUE071263T2 (hu) | 2021-03-24 | 2025-08-28 | Alcon Inc | Eljárás beágyazott hidrogél kontaktlencse elõállítására |
| US12194699B2 (en) | 2021-04-01 | 2025-01-14 | Alcon Inc. | Embedded hydrogel contact lenses |
| US12360289B2 (en) | 2021-04-01 | 2025-07-15 | Alcon Inc. | Method for making embedded hydrogel contact lenses |
| WO2023209569A1 (en) | 2022-04-26 | 2023-11-02 | Alcon Inc. | Method for making embedded hydrogel contact lenses |
| EP4514595A1 (en) | 2022-04-26 | 2025-03-05 | Alcon Inc. | Method for making embedded hydrogel contact lenses |
| WO2023218324A1 (en) | 2022-05-09 | 2023-11-16 | Alcon Inc. | Method for making embedded hydrogel contact lenses |
| EP4529621A1 (en) | 2022-05-23 | 2025-04-02 | Alcon Inc. | Uv/hevl-filtering contact lenses |
| EP4532187A1 (en) | 2022-05-25 | 2025-04-09 | Alcon Inc. | Method for making embedded hydrogel contact lenses |
| WO2024194826A1 (en) | 2023-03-22 | 2024-09-26 | Alcon Inc. | Method for making embedded hydrogel contact lenses |
| US20240399686A1 (en) | 2023-06-01 | 2024-12-05 | Alcon Inc. | Method for making embedded hydrogel contact lenses |
| US20260104598A1 (en) | 2024-10-15 | 2026-04-16 | Alcon Inc. | Composite contact lenses with ultrathin objects |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3503942A (en) * | 1965-10-23 | 1970-03-31 | Maurice Seiderman | Hydrophilic plastic contact lens |
| US4254065A (en) * | 1979-04-04 | 1981-03-03 | Ratkowski Donald J | Injection molding of contact lenses |
| US4408023A (en) * | 1980-11-12 | 1983-10-04 | Tyndale Plains-Hunter, Ltd. | Polyurethane diacrylate compositions useful for contact lenses and the like |
| US4359558A (en) * | 1980-11-12 | 1982-11-16 | Tyndale Plains-Hunter, Ltd. | Polyurethane diacrylate compositions |
| US4454309A (en) * | 1980-11-12 | 1984-06-12 | Tyndale Plains-Hunter, Ltd. | Polyurethane polyene compositions |
| US4430458A (en) * | 1981-10-08 | 1984-02-07 | Kelvin Lenses Limited | Hydrogel-forming polymeric materials |
| FR2539135B1 (fr) * | 1983-01-11 | 1986-02-28 | Essilor Int | Hydrogels de polyurethane et procede de fabrication |
| US4536554A (en) * | 1984-02-22 | 1985-08-20 | Barnes-Hind, Inc. | Hydrophilic polymers and contact lenses made therefrom |
| CA1279741C (en) * | 1984-09-28 | 1991-01-29 | Alton J. Gasper | Grouting composition |
| US4780488A (en) * | 1986-08-29 | 1988-10-25 | Ciba-Geigy Corporation | Wettable, flexible, oxygen permeable, substantially non-swellable contact lens containing polyoxyalkylene backbone units, and use thereof |
| DE3784152T3 (de) * | 1986-12-26 | 1997-03-20 | Nippon Catalytic Chem Ind | Harz mit hohem Brechungsindex, Verfahren zu seiner Herstellung und optische Materialien aus diesem Harz. |
| JPH0788025B2 (ja) * | 1987-04-28 | 1995-09-27 | 三菱瓦斯化学株式会社 | 偏肉補強部構造を有する合成樹脂成形品の製造法 |
| US4857606A (en) * | 1987-06-05 | 1989-08-15 | Ciga-Geigy Corporation | Wettable, flexible, oxygen permeable, substantially non-swellable contact lens containing polyoxyalkylene backbone units, and use thereof |
| US4786657A (en) * | 1987-07-02 | 1988-11-22 | Minnesota Mining And Manufacturing Company | Polyurethanes and polyurethane/polyureas crosslinked using 2-glyceryl acrylate or 2-glyceryl methacrylate |
| US4859780A (en) * | 1988-02-26 | 1989-08-22 | Ciba-Geigy Corporation | Hydrophilic modifier monomers |
| US5087392A (en) * | 1988-05-31 | 1992-02-11 | Sola Usa, Inc. | Method of mold contact lenses |
| CN1039599A (zh) * | 1988-07-15 | 1990-02-14 | 上海科学技术大学 | 空气中辐射固化聚氨酯的合成方法 |
| US4983702A (en) * | 1988-09-28 | 1991-01-08 | Ciba-Geigy Corporation | Crosslinked siloxane-urethane polymer contact lens |
| US5115056A (en) | 1989-06-20 | 1992-05-19 | Ciba-Geigy Corporation | Fluorine and/or silicone containing poly(alkylene-oxide)-block copolymers and contact lenses thereof |
| US5039769A (en) * | 1989-10-11 | 1991-08-13 | Ciba-Geigy Coproation | Wettable, flexible, oxygen permeable, substantially non-swellable contact lens containing polyoxyalkylene backbone units, and use thereof |
| DE4025776A1 (de) * | 1990-08-14 | 1992-02-20 | Thera Ges Fuer Patente | Praepolymer, daraus hergestellte haertbare masse und deren verwendung |
| US5170192A (en) * | 1990-11-29 | 1992-12-08 | Pilkington Visioncare, Inc. | Oxygen permeable bifocal contact lenses and their manufacture |
| TW328535B (en) * | 1993-07-02 | 1998-03-21 | Novartis Ag | Functional photoinitiators and their manufacture |
| US5760100B1 (en) * | 1994-09-06 | 2000-11-14 | Ciba Vision Corp | Extended wear ophthalmic lens |
| US5674942A (en) * | 1995-03-31 | 1997-10-07 | Johnson & Johnson Vision Products, Inc. | Interpenetrating polymer networks for contact lens production |
| US5656210A (en) * | 1995-03-31 | 1997-08-12 | Johnson & Johnson Vision Products, Inc. | Reaction injection molding as a process to prepare contact lenses |
| TW393498B (en) * | 1995-04-04 | 2000-06-11 | Novartis Ag | The preparation and use of Polysiloxane-comprising perfluoroalkyl ethers |
-
1998
- 1998-09-14 EP EP98951391A patent/EP1017734B1/en not_active Expired - Lifetime
- 1998-09-14 AU AU97432/98A patent/AU9743298A/en not_active Abandoned
- 1998-09-14 AR ARP980104570A patent/AR017108A1/es unknown
- 1998-09-14 JP JP2000511800A patent/JP4616473B2/ja not_active Expired - Fee Related
- 1998-09-14 WO PCT/EP1998/005826 patent/WO1999014253A1/en not_active Ceased
- 1998-09-14 US US09/508,785 patent/US6479587B1/en not_active Expired - Lifetime
- 1998-09-14 DE DE69807509T patent/DE69807509T2/de not_active Expired - Lifetime
- 1998-09-15 ZA ZA988420A patent/ZA988420B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE69807509D1 (de) | 2002-10-02 |
| JP2001516778A (ja) | 2001-10-02 |
| US6479587B1 (en) | 2002-11-12 |
| EP1017734B1 (en) | 2002-08-28 |
| WO1999014253A1 (en) | 1999-03-25 |
| DE69807509T2 (de) | 2003-04-24 |
| EP1017734A1 (en) | 2000-07-12 |
| AU9743298A (en) | 1999-04-05 |
| ZA988420B (en) | 1999-03-16 |
| AR017108A1 (es) | 2001-08-22 |
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