KR20150100765A - 경화성 실세스퀴옥산 중합체, 조성물, 물품, 및 방법 - Google Patents
경화성 실세스퀴옥산 중합체, 조성물, 물품, 및 방법 Download PDFInfo
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- KR20150100765A KR20150100765A KR1020157019391A KR20157019391A KR20150100765A KR 20150100765 A KR20150100765 A KR 20150100765A KR 1020157019391 A KR1020157019391 A KR 1020157019391A KR 20157019391 A KR20157019391 A KR 20157019391A KR 20150100765 A KR20150100765 A KR 20150100765A
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- South Korea
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- curable
- formula
- polymer
- ethylenically unsaturated
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- 229920000642 polymer Polymers 0.000 title claims abstract description 133
- 239000000203 mixture Substances 0.000 title claims abstract description 67
- 238000000034 method Methods 0.000 title claims abstract description 21
- 238000000576 coating method Methods 0.000 claims abstract description 24
- 239000011248 coating agent Substances 0.000 claims abstract description 18
- 125000000962 organic group Chemical group 0.000 claims abstract description 16
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 13
- 125000004429 atom Chemical group 0.000 claims abstract description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 9
- -1 acryloyloxy group Chemical group 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 125000000732 arylene group Chemical group 0.000 claims description 30
- 125000002947 alkylene group Chemical group 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 239000002105 nanoparticle Substances 0.000 claims description 26
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 25
- 239000000758 substrate Substances 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 22
- 239000003960 organic solvent Substances 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 239000011521 glass Substances 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 239000010410 layer Substances 0.000 claims description 10
- 238000006482 condensation reaction Methods 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000003848 UV Light-Curing Methods 0.000 claims description 6
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- 229910052760 oxygen Inorganic materials 0.000 claims description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
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- 125000003545 alkoxy group Chemical group 0.000 description 7
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 6
- 238000009833 condensation Methods 0.000 description 5
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- 125000004122 cyclic group Chemical group 0.000 description 5
- 125000003709 fluoroalkyl group Chemical group 0.000 description 5
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- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 4
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 4
- 125000005248 alkyl aryloxy group Chemical group 0.000 description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 125000002837 carbocyclic group Chemical group 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 239000012949 free radical photoinitiator Substances 0.000 description 4
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- 239000002184 metal Substances 0.000 description 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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- 238000003756 stirring Methods 0.000 description 4
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- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 3
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229910052755 nonmetal Inorganic materials 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
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- 239000010703 silicon Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 description 2
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- LUZRKMGMNFOSFZ-UHFFFAOYSA-N but-3-enyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCC=C LUZRKMGMNFOSFZ-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- HOWGUJZVBDQJKV-UHFFFAOYSA-N docosane Chemical compound CCCCCCCCCCCCCCCCCCCCCC HOWGUJZVBDQJKV-UHFFFAOYSA-N 0.000 description 2
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
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- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- DVFZJTWMDGYBCD-UHFFFAOYSA-N triethoxy(hex-1-enyl)silane Chemical compound CCCCC=C[Si](OCC)(OCC)OCC DVFZJTWMDGYBCD-UHFFFAOYSA-N 0.000 description 2
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 2
- 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
- WXNCJVBZNJOFEG-UHFFFAOYSA-N CC(C(=O)C1=CC=CC=C1)C.COC1=C(C(=O)P(CC(CC(C)(C)C)C)C(C2=C(C=CC=C2OC)OC)=O)C(=CC=C1)OC Chemical compound CC(C(=O)C1=CC=CC=C1)C.COC1=C(C(=O)P(CC(CC(C)(C)C)C)C(C2=C(C=CC=C2OC)OC)=O)C(=CC=C1)OC WXNCJVBZNJOFEG-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
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- LFOXEOLGJPJZAA-UHFFFAOYSA-N [(2,6-dimethoxybenzoyl)-(2,4,4-trimethylpentyl)phosphoryl]-(2,6-dimethoxyphenyl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)P(=O)(CC(C)CC(C)(C)C)C(=O)C1=C(OC)C=CC=C1OC LFOXEOLGJPJZAA-UHFFFAOYSA-N 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- ZNAAXKXXDQLJIX-UHFFFAOYSA-N bis(2-cyclohexyl-3-hydroxyphenyl)methanone Chemical compound C1CCCCC1C=1C(O)=CC=CC=1C(=O)C1=CC=CC(O)=C1C1CCCCC1 ZNAAXKXXDQLJIX-UHFFFAOYSA-N 0.000 description 1
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- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- NYIKUOULKCEZDO-UHFFFAOYSA-N triethoxy(3,3,4,4,5,5,6,6,6-nonafluorohexyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)F NYIKUOULKCEZDO-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
- B05D3/061—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation using U.V.
- B05D3/065—After-treatment
- B05D3/067—Curing or cross-linking the coating
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Plasma & Fusion (AREA)
- Physics & Mathematics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Paints Or Removers (AREA)
- Silicon Polymers (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
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| US201261740590P | 2012-12-21 | 2012-12-21 | |
| US61/740,590 | 2012-12-21 | ||
| US201361829357P | 2013-05-31 | 2013-05-31 | |
| US61/829,357 | 2013-05-31 | ||
| PCT/US2013/075237 WO2014099699A1 (en) | 2012-12-21 | 2013-12-16 | Curable silsesquioxane polymers, compositions, articles, and methods |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20150100765A true KR20150100765A (ko) | 2015-09-02 |
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Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9453109B2 (enExample) |
| EP (1) | EP2935493B1 (enExample) |
| JP (1) | JP2016507613A (enExample) |
| KR (1) | KR20150100765A (enExample) |
| CN (1) | CN104870584B (enExample) |
| WO (1) | WO2014099699A1 (enExample) |
Families Citing this family (19)
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| US10066123B2 (en) | 2013-12-09 | 2018-09-04 | 3M Innovative Properties Company | Curable silsesquioxane polymers, compositions, articles, and methods |
| US10392538B2 (en) | 2014-06-20 | 2019-08-27 | 3M Innovative Properties Company | Adhesive compositions comprising a silsesquioxane polymer crosslinker, articles and methods |
| US10370564B2 (en) | 2014-06-20 | 2019-08-06 | 3M Innovative Properties Company | Adhesive compositions comprising a silsesquioxane polymer crosslinker, articles and methods |
| EP3157986A1 (en) | 2014-06-20 | 2017-04-26 | 3M Innovative Properties Company | Curable polymers comprising silsesquioxane polymer core and silsesquioxane polymer outer layer and methods |
| WO2015200421A1 (en) * | 2014-06-27 | 2015-12-30 | Corning Incorporated | Uv-curable coating compositions for glass based on epoxy/oxetane compounds, epoxy functionalized silsesquioxane and epoxy functionalized nanoparticles. |
| US9957416B2 (en) | 2014-09-22 | 2018-05-01 | 3M Innovative Properties Company | Curable end-capped silsesquioxane polymer comprising reactive groups |
| EP3197966A1 (en) | 2014-09-22 | 2017-08-02 | 3M Innovative Properties Company | Curable polymers comprising silsesquioxane polymer core silsesquioxane polymer outer layer, and reactive groups |
| CN105086449B (zh) * | 2015-09-11 | 2017-05-24 | 西北工业大学 | 一种含磷poss阻燃型双马来酰亚胺树脂及其制备方法 |
| WO2017116656A1 (en) | 2015-12-29 | 2017-07-06 | 3M Innovative Properties Company | Composites for high frequency electromagnetic interference (emi) applications |
| KR102412888B1 (ko) * | 2017-05-12 | 2022-06-28 | 삼성디스플레이 주식회사 | 하드코팅용 조성물, 및 하드코팅층을 포함하는 윈도우 부재 |
| WO2019058232A1 (en) | 2017-09-22 | 2019-03-28 | 3M Innovative Properties Company | POLYMERS, COMPOSITIONS AND ARTICLES OF SILSESQUIOXANE |
| CN111094478B (zh) | 2017-09-22 | 2021-04-13 | 3M创新有限公司 | 包含倍半硅氧烷聚合物和游离硅氧烷的组合物，以及制品 |
| WO2019058228A1 (en) | 2017-09-22 | 2019-03-28 | 3M Innovative Properties Company | SILSESQUIOXANE POLYMERS, COMPOSITIONS, METHODS, AND ARTICLES |
| US12043638B2 (en) | 2017-09-22 | 2024-07-23 | 3M Innovative Properties Company | Cyclic siloxanes, compositions, methods, and articles |
| CN111148795B (zh) * | 2017-09-28 | 2023-06-23 | 3M创新有限公司 | 有机硅的光自由基固化 |
| CN111108154B (zh) * | 2017-09-28 | 2022-01-28 | 3M创新有限公司 | 有机硅类压敏粘合剂 |
| EP3724283A1 (en) * | 2017-12-13 | 2020-10-21 | 3M Innovative Properties Company | Curable fluorinated silsesquioxane compositions |
| CN110330653B (zh) * | 2019-07-05 | 2020-10-23 | 北京化工大学 | 一种耐高温高折射率的主链含亚苯基的钛杂化硅树脂、其制备方法及应用 |
| WO2024062392A1 (en) | 2022-09-20 | 2024-03-28 | 3M Innovative Properties Company | Composition and article including a thermoplastic and a branched silsesquioxane polymer and related process |
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| US4761393A (en) | 1987-07-27 | 1988-08-02 | Amoco Corporation | Method for placing a catalytically active alkali metal on a catalyst support |
| US4822828A (en) * | 1987-11-23 | 1989-04-18 | Hoechst Celanese Corporation | Radiation curable coating composition based on a silica/vinyl-functional silanol dispersion |
| DE3837397A1 (de) | 1988-11-03 | 1990-05-10 | Wacker Chemie Gmbh | Neue organooligosilsesquioxane |
| DE4042141A1 (de) * | 1990-12-28 | 1992-07-02 | Wacker Chemie Gmbh | Verfahren zur herstellung von organopolysiloxanhydrosolen |
| US5484867A (en) | 1993-08-12 | 1996-01-16 | The University Of Dayton | Process for preparation of polyhedral oligomeric silsesquioxanes and systhesis of polymers containing polyhedral oligomeric silsesqioxane group segments |
| US6770726B1 (en) | 1995-09-12 | 2004-08-03 | Gelest, Inc. | β-substituted organosilsesquioxane polymers |
| US5609925A (en) | 1995-12-04 | 1997-03-11 | Dow Corning Corporation | Curing hydrogen silsesquioxane resin with an electron beam |
| JP3930591B2 (ja) * | 1995-12-22 | 2007-06-13 | 東陶機器株式会社 | 光触媒性親水性コーティング組成物、親水性被膜の形成方法および被覆物品 |
| JP3635180B2 (ja) * | 1997-02-24 | 2005-04-06 | ダウ コーニング アジア株式会社 | シリル化ポリメチルシルセスキオキサン、その製造方法、それを用いた組成物 |
| JP2000017230A (ja) * | 1998-07-02 | 2000-01-18 | Showa Denko Kk | 光触媒を含有するコーティング組成物及び塗膜形成方法 |
| US6927270B2 (en) | 2001-06-27 | 2005-08-09 | Hybrid Plastics Llp | Process for the functionalization of polyhedral oligomeric silsesquioxanes |
| US20040047988A1 (en) * | 2000-11-17 | 2004-03-11 | Jin-Kyu Lee | Poly(methylsilsesquioxane) copolymers and preparation method thereof |
| JP4742212B2 (ja) | 2002-08-06 | 2011-08-10 | Ｊｎｃ株式会社 | シルセスキオキサン誘導体の製造方法およびシルセスキオキサン誘導体 |
| US7241437B2 (en) | 2004-12-30 | 2007-07-10 | 3M Innovative Properties Company | Zirconia particles |
| US7867689B2 (en) | 2007-05-18 | 2011-01-11 | International Business Machines Corporation | Method of use for photopatternable dielectric materials for BEOL applications |
| US8470516B2 (en) | 2007-05-18 | 2013-06-25 | International Business Machines Corporation | Method of forming a relief pattern by e-beam lithography using chemical amplification, and derived articles |
| DK2170994T3 (en) * | 2007-06-29 | 2016-03-14 | Saint Gobain Performance Plast | Silicon compositions, articles thereof, and processes for preparing such compositions silicon |
| EP2620413B1 (en) | 2007-12-28 | 2020-07-01 | 3M Innovative Properties Company | Continuous hydrothermal reactor system comprising a fluorinated polymer tubular reactor |
| JP2011510133A (ja) * | 2008-01-15 | 2011-03-31 | ダウ・コーニング・コーポレイション | シルセスキオキサン樹脂 |
| CN102131819B (zh) * | 2008-08-26 | 2014-04-16 | 关西涂料株式会社 | 具有可聚合官能团的倍半硅氧烷化合物 |
| JP2012510554A (ja) * | 2008-12-03 | 2012-05-10 | ソレク ヌークリア リサーチ センター | Ｕｖ硬化性無機−有機ハイブリッド樹脂及びその調製方法 |
| US8431670B2 (en) * | 2009-08-31 | 2013-04-30 | International Business Machines Corporation | Photo-patternable dielectric materials and formulations and methods of use |
| US8389663B2 (en) | 2009-10-08 | 2013-03-05 | International Business Machines Corporation | Photo-patternable dielectric materials curable to porous dielectric materials, formulations, precursors and methods of use thereof |
| DE112011101961T5 (de) * | 2010-06-08 | 2013-03-21 | Dic Corporation | Dichtungsmaterial, Solarzellenmodul und Leuchtdiode |
| JP2012014021A (ja) * | 2010-07-01 | 2012-01-19 | Fujifilm Corp | 感光性組成物、パターン形成材料、並びに、これを用いた感光性膜、パターン形成方法、パターン膜、反射防止膜、絶縁膜、光学デバイス及び電子デバイス |
| US9711744B2 (en) | 2012-12-21 | 2017-07-18 | 3M Innovative Properties Company | Patterned structured transfer tape |
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2013
- 2013-12-16 CN CN201380067074.0A patent/CN104870584B/zh active Active
- 2013-12-16 KR KR1020157019391A patent/KR20150100765A/ko not_active Withdrawn
- 2013-12-16 US US14/441,522 patent/US9453109B2/en active Active
- 2013-12-16 WO PCT/US2013/075237 patent/WO2014099699A1/en not_active Ceased
- 2013-12-16 JP JP2015549518A patent/JP2016507613A/ja active Pending
- 2013-12-16 EP EP13815642.7A patent/EP2935493B1/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20150299399A1 (en) | 2015-10-22 |
| EP2935493A1 (en) | 2015-10-28 |
| EP2935493B1 (en) | 2016-09-21 |
| CN104870584A (zh) | 2015-08-26 |
| CN104870584B (zh) | 2017-07-07 |
| JP2016507613A (ja) | 2016-03-10 |
| US9453109B2 (en) | 2016-09-27 |
| WO2014099699A1 (en) | 2014-06-26 |
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