RU2009141367A - Ароматические уретанакрилаты, имеющие высокий показатель преломления - Google Patents
Ароматические уретанакрилаты, имеющие высокий показатель преломления Download PDFInfo
- Publication number
- RU2009141367A RU2009141367A RU2009141367/04A RU2009141367A RU2009141367A RU 2009141367 A RU2009141367 A RU 2009141367A RU 2009141367/04 A RU2009141367/04 A RU 2009141367/04A RU 2009141367 A RU2009141367 A RU 2009141367A RU 2009141367 A RU2009141367 A RU 2009141367A
- Authority
- RU
- Russia
- Prior art keywords
- olefinically unsaturated
- compounds
- urethane
- isocyanates
- optionally
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract 13
- -1 unsaturated aromatic urethanes Chemical class 0.000 claims abstract 11
- 239000012948 isocyanate Substances 0.000 claims abstract 10
- 150000002513 isocyanates Chemical class 0.000 claims abstract 9
- 238000000034 method Methods 0.000 claims abstract 8
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract 6
- KGLSETWPYVUTQX-UHFFFAOYSA-N tris(4-isocyanatophenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound C1=CC(N=C=O)=CC=C1OP(=S)(OC=1C=CC(=CC=1)N=C=O)OC1=CC=C(N=C=O)C=C1 KGLSETWPYVUTQX-UHFFFAOYSA-N 0.000 claims abstract 3
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 claims abstract 2
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 claims abstract 2
- 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 claims abstract 2
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical group N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000007945 N-acyl ureas Chemical class 0.000 claims abstract 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000003118 aryl group Chemical group 0.000 claims abstract 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000004202 carbamide Substances 0.000 claims abstract 2
- 150000001718 carbodiimides Chemical class 0.000 claims abstract 2
- MHCLJIVVJQQNKQ-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical class CCOC(N)=O.CC(=C)C(O)=O MHCLJIVVJQQNKQ-UHFFFAOYSA-N 0.000 claims abstract 2
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000000945 filler Substances 0.000 claims abstract 2
- 230000003993 interaction Effects 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims abstract 2
- 239000002105 nanoparticle Substances 0.000 claims abstract 2
- 229920001228 polyisocyanate Polymers 0.000 claims abstract 2
- 239000005056 polyisocyanate Substances 0.000 claims abstract 2
- 230000005855 radiation Effects 0.000 claims abstract 2
- 239000003381 stabilizer Substances 0.000 claims abstract 2
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 claims 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 2
- PBLNHHSDYFYZNC-UHFFFAOYSA-N (1-naphthyl)methanol Chemical compound C1=CC=C2C(CO)=CC=CC2=C1 PBLNHHSDYFYZNC-UHFFFAOYSA-N 0.000 claims 1
- MVOSNPUNXINWAD-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanol Chemical compound CC(O)C1=CC=C(Cl)C=C1 MVOSNPUNXINWAD-UHFFFAOYSA-N 0.000 claims 1
- GPOFSFLJOIAMSA-UHFFFAOYSA-N 1-chloro-4-ethylbenzene Chemical compound CCC1=CC=C(Cl)C=C1 GPOFSFLJOIAMSA-UHFFFAOYSA-N 0.000 claims 1
- ZKJNETINGMOHJG-UHFFFAOYSA-N 1-prop-1-enoxyprop-1-ene Chemical class CC=COC=CC ZKJNETINGMOHJG-UHFFFAOYSA-N 0.000 claims 1
- 150000003923 2,5-pyrrolediones Chemical class 0.000 claims 1
- MWFLUYFYHANMCM-UHFFFAOYSA-N 2-(2-hydroxyethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCO)C(=O)C2=C1 MWFLUYFYHANMCM-UHFFFAOYSA-N 0.000 claims 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- HZFRKZWBVUJYDA-UHFFFAOYSA-N 2-(4-chlorophenyl)ethanol Chemical compound OCCC1=CC=C(Cl)C=C1 HZFRKZWBVUJYDA-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- IIKVAWLYHHZRGV-UHFFFAOYSA-N 2-carbazol-9-ylethanol Chemical compound C1=CC=C2N(CCO)C3=CC=CC=C3C2=C1 IIKVAWLYHHZRGV-UHFFFAOYSA-N 0.000 claims 1
- JZDSOQSUCWVBMV-UHFFFAOYSA-N 2-ethylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CC)C(=O)C2=C1 JZDSOQSUCWVBMV-UHFFFAOYSA-N 0.000 claims 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 claims 1
- IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 claims 1
- PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims 1
- 150000003926 acrylamides Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 claims 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims 1
- 150000002688 maleic acid derivatives Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims 1
- 229920001610 polycaprolactone Polymers 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 claims 1
- LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 claims 1
- 150000003673 urethanes Chemical class 0.000 claims 1
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 abstract 1
- HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical compound O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 abstract 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 abstract 1
Classifications
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- G—PHYSICS
- G11—INFORMATION STORAGE
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- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/245—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing a polymeric component
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- 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
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/06—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyurethanes
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08F290/06—Polymers provided for in subclass C08G
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F290/06—Polymers provided for in subclass C08G
- C08F290/061—Polyesters; Polycarbonates
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- 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
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- C08F290/02—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 end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/067—Polyurethanes; Polyureas
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- 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
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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
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
- C08G18/2825—Alkanols, cycloalkanols or arylalkanols including terpenealcohols having at least 6 carbon atoms
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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
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/285—Nitrogen containing compounds
-
- 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
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- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
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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
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- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
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- 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
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- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/776—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur phosphorus
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/8141—Unsaturated isocyanates or isothiocyanates masked
- C08G18/815—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen
- C08G18/8158—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen
- C08G18/8175—Polyisocyanates or polyisothiocyanates masked with unsaturated compounds having active hydrogen with unsaturated compounds having only one group containing active hydrogen with esters of acrylic or alkylacrylic acid having only one group containing active hydrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
- C08L75/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C08L75/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
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- G—PHYSICS
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/001—Phase modulating patterns, e.g. refractive index patterns
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
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- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
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- G11B7/0065—Recording, reproducing or erasing by using optical interference patterns, e.g. holograms
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- G—PHYSICS
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- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/2403—Layers; Shape, structure or physical properties thereof
- G11B7/24035—Recording layers
- G11B7/24044—Recording layers for storing optical interference patterns, e.g. holograms; for storing data in three dimensions, e.g. volume storage
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Abstract
1. Голографическая среда, полученная из олефиноненасыщенных ароматических уретанов, имеющая показатель преломления при λ=532 нм≥1,5. ! 2. Голографическая среда по п.1, отличающаяся тем, что олефиноненасыщенные ароматические уретаны представляют собой уретанакрилаты и/или уретанметакрилаты. ! 3. Способ получения олефиноненасыщенных ароматических уретанов, причем этот способ содержит стадии ! A) взаимодействия одного или нескольких ароматических полиизоцианатов с ! Б) одним или несколькими соединениями, реакционноспособными по отношению к изоцианатам, имеющими, по меньшей мере, одну сшиваемую излучением олефиноненасыщенную двойную связь, ! B) необязательно, одним или несколькими соединениями, реакционноспособными по отношению к изоцианатам, которые не содержат сшиваемых облучением олефиноненасыщенных двойных связей, ! Г) необязательно, одним или несколькими наполнителями из наночастиц и ! Д) необязательно, одним или несколькими стабилизаторами, где олефиноненасыщенные ароматические уретаны имеют показатель преломления при λ=532 нм≥1,5. ! 4. Способ по п.3, где одно или несколько соединений, выбранных из группы, состоящей из 1,4-фенилендиизоцианата, 2,4- и/или 2,6-толуилендиизоцианата, 1,5-нафтилендиизоцианата, 2,4'- или 4,4'-дифенилметандиизоцианата, трифенилметан-4,4',4''-триизоцианата и трис(п-изоцианатофенил)тиофосфата, одного или нескольких вторичных продуктов указанных выше мономерных изоцианатов, имеющих уретановые, мочевинные, карбодиимидные, ацилмочевинные, изоциануратные, аллофанатные, биуретные, оксадиазинтрионные, уретдионные или иминооксадиазиндионные структуры, и смесей указанных выше соединений, использ�
Claims (12)
1. Голографическая среда, полученная из олефиноненасыщенных ароматических уретанов, имеющая показатель преломления при λ=532 нм≥1,5.
2. Голографическая среда по п.1, отличающаяся тем, что олефиноненасыщенные ароматические уретаны представляют собой уретанакрилаты и/или уретанметакрилаты.
3. Способ получения олефиноненасыщенных ароматических уретанов, причем этот способ содержит стадии
A) взаимодействия одного или нескольких ароматических полиизоцианатов с
Б) одним или несколькими соединениями, реакционноспособными по отношению к изоцианатам, имеющими, по меньшей мере, одну сшиваемую излучением олефиноненасыщенную двойную связь,
B) необязательно, одним или несколькими соединениями, реакционноспособными по отношению к изоцианатам, которые не содержат сшиваемых облучением олефиноненасыщенных двойных связей,
Г) необязательно, одним или несколькими наполнителями из наночастиц и
Д) необязательно, одним или несколькими стабилизаторами, где олефиноненасыщенные ароматические уретаны имеют показатель преломления при λ=532 нм≥1,5.
4. Способ по п.3, где одно или несколько соединений, выбранных из группы, состоящей из 1,4-фенилендиизоцианата, 2,4- и/или 2,6-толуилендиизоцианата, 1,5-нафтилендиизоцианата, 2,4'- или 4,4'-дифенилметандиизоцианата, трифенилметан-4,4',4''-триизоцианата и трис(п-изоцианатофенил)тиофосфата, одного или нескольких вторичных продуктов указанных выше мономерных изоцианатов, имеющих уретановые, мочевинные, карбодиимидные, ацилмочевинные, изоциануратные, аллофанатные, биуретные, оксадиазинтрионные, уретдионные или иминооксадиазиндионные структуры, и смесей указанных выше соединений, используют в A).
5. Способ по п.3, где одно или несколько соединений из группы, состоящей из акрилатов, метакрилатов, малеинатов, фумаратов, малеимидов, акриламидов, виниловых простых эфиров, пропениловых простых эфиров, аллиловых простых эфиров и соединений, содержащих дициклопентадиенильные звенья, которые имеют, по меньшей мере, одну группу, реакционноспособную по отношению к изоцианатам на молекулу, используют в Б).
6. Способ по п.3, где одно или несколько соединений из группы, состоящей из 2-гидроксиэтилакрилата, гидроксипропилакрилата, 4-гидроксибутилакрилата, поли(ε-капролактон)моно(мет)акрилата, пентаэритритилтриакрилата и продукта реакции акриловой кислоты с глицидилметакрилатом, используют в Б).
7. Способ по п.3, где одно или несколько соединений, выбранных из 9-(2-гидроксиэтил)-9Н-карбазола, гидроксиметилнафталина, N-(2-гидроксиэтил)фталимида, 2-фенилэтанола, (п-хлор)фенилэтанола, 2-(п-хлорфенил)этанола, трифенилметанола и/или нафталинтиометанола, используют в В).
8. Олефиноненасыщенные ароматические уретаны, получаемые по любому из пп.3-7.
9. Уретан(мет)акрилаты, содержащие, по меньшей мере, одно структурное звено формул
и
в которых Х представляет собой кислород, аминогруппу или серу, а R содержит, по меньшей мере, 30 мол.% олефиноненасыщенных углеводородных радикалов, необязательно, содержащих гетероатомы, и не более 70 мол.% углеводородных радикалов, необязательно, содержащих гетероатомы, которые не содержат олефиноненасыщенных групп.
10. Уретан(мет)акрилаты по п.9, где олефиноненасыщенные углеводородные радикалы, необязательно, содержащие гетероатомы, представляют собой радикалы этилакрилата, пропилакрилата и/или бутилакрилата, и углеводородные радикалы, необязательно, содержащие гетероатомы, которые не содержат олефиноненасыщенных групп, представляют собой радикалы 9Н-карбазола, 9-этил-9Н-карбазола, нафталина, метилнафталина, N-этилфталимида, бензола, этилбензола, (п-хлор)этилбензола и/или трифенилметана.
11. Уретан(мет)акрилаты по п.9, полученные взаимодействием трис(п-изоцианатофенил)тиофосфата и/или трифенилметан-4,4',4''-триизоцианата с реакционноспособными по отношению к изоцианатам соединениями, имеющими, по меньшей мере, одну сшиваемую излучением олефиноненасыщенную двойную связь.
12. Голографическая среда, полученная из а) олефиноненасыщенных уретанов по п.8 или уретан(мет)акрилатов по п.9, б) изоцианатного компонента, в) реакционноспособного по отношению к изоцианатам компонента, и г) фотоинициатора.
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| CN113621121B (zh) * | 2021-07-15 | 2022-08-23 | 中联重科股份有限公司 | 聚氨酯组合物和聚氨酯材料的制备方法及应用 |
| CN114213626B (zh) * | 2021-12-09 | 2023-04-28 | 江苏三木化工股份有限公司 | 一种植物油基光固化聚氨酯丙烯酸酯的制备方法 |
| CN114231163A (zh) * | 2021-12-22 | 2022-03-25 | 武汉工程大学 | 一种聚氨酯类有机无机复合材料及其制备方法和应用 |
| CN115785756B (zh) * | 2022-12-12 | 2023-07-28 | 江苏视科新材料股份有限公司 | 一种折光指数可调节的防蓝光涂层材料的制备方法 |
| CN115785811B (zh) * | 2022-12-12 | 2023-07-28 | 江苏视科新材料股份有限公司 | 一种高折射率防蓝光材料和防蓝光滤光片 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5916987A (en) | 1996-05-29 | 1999-06-29 | Mitsui Chemicals, Inc. | Thiol and Sulfur-containing O-(meth) acrylate compounds and use thereof |
| US6232038B1 (en) * | 1998-10-07 | 2001-05-15 | Mitsubishi Chemical Corporation | Photosensitive composition, image-forming material and image-forming method employing it |
| DE69916750T2 (de) * | 1998-11-17 | 2005-01-05 | Showa Denko K.K. | Photohärtbare Zusammensetzung |
| EP1014113A3 (en) * | 1998-12-21 | 2001-05-09 | Dsm N.V. | Photo curable resin composition and optical parts |
| HUP0203434A3 (en) * | 1999-11-18 | 2010-01-28 | Ppg Ind Ohio | Optical resin composition |
| KR100453344B1 (ko) | 2000-09-22 | 2004-10-20 | 미쯔이카가쿠 가부시기가이샤 | 아크릴산 에스테르화합물 및 그 용도 |
| US6780546B2 (en) | 2001-08-30 | 2004-08-24 | Inphase Technologies, Inc. | Blue-sensitized holographic media |
| EP1548039B1 (en) * | 2002-07-29 | 2008-08-13 | Mitsui Chemicals, Inc. | Photopolymerizable composition and use thereof |
| JP3852613B2 (ja) * | 2003-02-12 | 2006-12-06 | 三菱化学株式会社 | 感光性組成物、並びにそれを用いた画像形成材料、画像形成材、及び画像形成方法 |
| JP2004295058A (ja) * | 2003-02-14 | 2004-10-21 | Mitsubishi Chemicals Corp | 感光性組成物 |
| JP3896098B2 (ja) * | 2003-06-27 | 2007-03-22 | 株式会社東芝 | ホログラム記録媒体およびその作製方法 |
| JP2006307159A (ja) * | 2005-03-28 | 2006-11-09 | Toyo Ink Mfg Co Ltd | 硬化性高屈折率材料及び該硬化性高屈折率材料を用いてなる積層体 |
| JP4675197B2 (ja) * | 2005-09-20 | 2011-04-20 | 富士フイルム株式会社 | 溶媒非含有の光記録用組成物及びその製造方法、並びに光記録媒体 |
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2008
- 2008-03-28 BR BRPI0810831-5A2A patent/BRPI0810831A2/pt not_active Application Discontinuation
- 2008-03-28 EP EP08734839.7A patent/EP2137220B1/en active Active
- 2008-03-28 RU RU2009141367/04A patent/RU2009141367A/ru not_active Application Discontinuation
- 2008-03-28 KR KR1020097021126A patent/KR20100015471A/ko not_active Withdrawn
- 2008-03-28 CN CN200880011274A patent/CN101668782A/zh active Pending
- 2008-03-28 IN IN5755DEN2009 patent/IN2009DN05755A/en unknown
- 2008-03-28 JP JP2010502436A patent/JP2010524036A/ja not_active Withdrawn
- 2008-03-28 CA CA002683882A patent/CA2683882A1/en not_active Abandoned
- 2008-03-28 WO PCT/EP2008/002464 patent/WO2008125199A1/en not_active Ceased
- 2008-04-10 TW TW097112920A patent/TW200909451A/zh unknown
- 2008-04-10 US US12/100,828 patent/US7981987B2/en active Active
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| IN2009DN05755A (ru) | 2015-07-24 |
| WO2008125199A1 (en) | 2008-10-23 |
| TW200909451A (en) | 2009-03-01 |
| BRPI0810831A2 (pt) | 2014-10-29 |
| CN101668782A (zh) | 2010-03-10 |
| IL200719A0 (en) | 2010-05-17 |
| US7981987B2 (en) | 2011-07-19 |
| JP2010524036A (ja) | 2010-07-15 |
| CA2683882A1 (en) | 2008-10-23 |
| KR20100015471A (ko) | 2010-02-12 |
| EP2137220A1 (en) | 2009-12-30 |
| US20080312403A1 (en) | 2008-12-18 |
| EP2137220B1 (en) | 2017-10-18 |
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