JP5580892B2 - 硬化性有機フッ素変性ポリシラザンを調製するための組成物及び方法、並びにそれによって調製されるポリシラザン - Google Patents
硬化性有機フッ素変性ポリシラザンを調製するための組成物及び方法、並びにそれによって調製されるポリシラザン Download PDFInfo
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- JP5580892B2 JP5580892B2 JP2012517754A JP2012517754A JP5580892B2 JP 5580892 B2 JP5580892 B2 JP 5580892B2 JP 2012517754 A JP2012517754 A JP 2012517754A JP 2012517754 A JP2012517754 A JP 2012517754A JP 5580892 B2 JP5580892 B2 JP 5580892B2
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- polysilazane
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- curable
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- 238000000034 method Methods 0.000 title claims description 20
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 229920000642 polymer Polymers 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 31
- 239000010702 perfluoropolyether Substances 0.000 claims description 29
- -1 isocyanato, isothiocyanato Chemical group 0.000 claims description 28
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 239000011737 fluorine Substances 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000002723 alicyclic group Chemical group 0.000 claims description 9
- 125000000524 functional group Chemical group 0.000 claims description 9
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
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- 229920001774 Perfluoroether Polymers 0.000 claims description 5
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- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 5
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- 125000003545 alkoxy group Chemical group 0.000 description 4
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- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
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- 229910052751 metal Inorganic materials 0.000 description 4
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- 150000003839 salts Chemical class 0.000 description 4
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- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- GUXJXWKCUUWCLX-UHFFFAOYSA-N CC1=NCCO1 Chemical compound CC1=NCCO1 GUXJXWKCUUWCLX-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- 229920003354 Modic® Polymers 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
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- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000005104 aryl silyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- HGKYTXHYFGGJIC-UHFFFAOYSA-N benzyl ethaneperoxoate Chemical compound CC(=O)OOCC1=CC=CC=C1 HGKYTXHYFGGJIC-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000005524 ceramic coating Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 229940005991 chloric acid Drugs 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000005701 difluoromethyleneoxy group Chemical group FC(F)([*:1])O[*:2] 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000011363 dried mixture Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 125000004474 heteroalkylene group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
- VLAGSAGYAIGJSU-UHFFFAOYSA-N hexanoyl hexaneperoxoate Chemical compound CCCCCC(=O)OOC(=O)CCCCC VLAGSAGYAIGJSU-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- AITGNBIDZSPQEO-UHFFFAOYSA-N n-(2-aminoethyl)-1,1,2,2,3,3,4,4,4-nonafluoro-n-methylbutane-1-sulfonamide Chemical compound NCCN(C)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F AITGNBIDZSPQEO-UHFFFAOYSA-N 0.000 description 1
- BKCRWQGYLZYQMJ-UHFFFAOYSA-N n-[2-[methyl(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonyl)amino]ethyl]propanamide Chemical compound CCC(=O)NCCN(C)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F BKCRWQGYLZYQMJ-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of 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; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- 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
- C08G77/60—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 in which all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/62—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of 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; Compositions of derivatives of such polymers
- C08L83/16—Compositions of 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; Compositions of derivatives of such polymers in which all the silicon atoms are connected by linkages other than oxygen atoms
-
- 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
- B05D2202/00—Metallic substrate
- B05D2202/20—Metallic substrate based on light metals
- B05D2202/25—Metallic substrate based on light metals based on Al
-
- 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
- B05D3/02—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 baking
- B05D3/0254—After-treatment
-
- 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
- B05D5/00—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
- B05D5/08—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures to obtain an anti-friction or anti-adhesive surface
- B05D5/083—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures to obtain an anti-friction or anti-adhesive surface involving the use of fluoropolymers
-
- 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
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22157409P | 2009-06-30 | 2009-06-30 | |
| US22157509P | 2009-06-30 | 2009-06-30 | |
| US61/221,574 | 2009-06-30 | ||
| US61/221,575 | 2009-06-30 | ||
| US12/792,153 US8329830B2 (en) | 2009-06-30 | 2010-06-02 | Surface treatment process and treated article |
| US12/792,065 US8324324B2 (en) | 2009-06-30 | 2010-06-02 | Composition and process for preparing curable organofluorine-modified polysilazanes, and polysilazanes prepared thereby |
| US12/792,153 | 2010-06-02 | ||
| US12/792,065 | 2010-06-02 | ||
| PCT/US2010/039894 WO2011002666A1 (en) | 2009-06-30 | 2010-06-25 | Composition and process for preparing curable organofluorine-modified polysilazanes, and polysilazanes prepared thereby |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012532207A JP2012532207A (ja) | 2012-12-13 |
| JP2012532207A5 JP2012532207A5 (enExample) | 2013-08-08 |
| JP5580892B2 true JP5580892B2 (ja) | 2014-08-27 |
Family
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| JP2012517754A Expired - Fee Related JP5580892B2 (ja) | 2009-06-30 | 2010-06-25 | 硬化性有機フッ素変性ポリシラザンを調製するための組成物及び方法、並びにそれによって調製されるポリシラザン |
| JP2012517755A Expired - Fee Related JP5616964B2 (ja) | 2009-06-30 | 2010-06-25 | 表面処理方法及び処理された物品 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2012517755A Expired - Fee Related JP5616964B2 (ja) | 2009-06-30 | 2010-06-25 | 表面処理方法及び処理された物品 |
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|---|---|
| US (2) | US8324324B2 (enExample) |
| EP (2) | EP2449000A4 (enExample) |
| JP (2) | JP5580892B2 (enExample) |
| CN (2) | CN102471493B (enExample) |
| WO (2) | WO2011002666A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2010071227A1 (en) * | 2008-12-17 | 2010-06-24 | Takasago International Corporation | Aluminium complexes and use thereof as a catalyst in intramolecular ring closure reactions |
| US8324324B2 (en) * | 2009-06-30 | 2012-12-04 | 3M Innovative Properties Company | Composition and process for preparing curable organofluorine-modified polysilazanes, and polysilazanes prepared thereby |
| CN102666666A (zh) * | 2009-12-22 | 2012-09-12 | 3M创新有限公司 | 制备架藏稳定的可固化聚硅氮烷的方法及由此制得的聚硅氮烷 |
| US9533918B2 (en) * | 2011-09-30 | 2017-01-03 | United Technologies Corporation | Method for fabricating ceramic material |
| US8809445B2 (en) * | 2012-06-22 | 2014-08-19 | Texas Research International, Inc. | Room temperature cured vinyl silazane compositions |
| EP2921510B1 (en) * | 2012-11-13 | 2019-10-02 | Daikin Industries, Ltd. | Surface treatment composition |
| JP5768805B2 (ja) * | 2012-11-26 | 2015-08-26 | 信越化学工業株式会社 | パーフルオロポリエーテル変性ポリシラザン及びその製造方法、表面処理剤並びに該表面処理剤で処理された物品 |
| EP3013876B1 (en) | 2013-06-25 | 2019-08-28 | 3M Innovative Properties Company | Moisture-curable composition, method of using, and composite article |
| CN105392825A (zh) * | 2013-07-19 | 2016-03-09 | Az电子材料卢森堡有限公司 | 用于发光二极管的封装材料 |
| CN103589339A (zh) * | 2013-11-13 | 2014-02-19 | 中国科学院化学研究所 | 聚硅氮烷涂覆溶液及制备含金属氧化物-SiO2复合涂层的方法 |
| US9994676B2 (en) | 2014-06-23 | 2018-06-12 | 3M Innovative Properties Company | Silicon-containing polymer and method of making a silicon-containing polymer |
| US9994732B1 (en) * | 2014-09-12 | 2018-06-12 | Steven Martin Johnson | Polysilazane and fluoroacrylate coating composition |
| CN105045451B (zh) * | 2015-08-14 | 2019-03-26 | 昆山国显光电有限公司 | 触控显示面板及其制造方法 |
| US10562065B1 (en) | 2015-11-03 | 2020-02-18 | Newtech Llc | Systems and methods for application of polysilazane and fluoroacrylate coating compositions |
| US10584264B1 (en) | 2016-02-25 | 2020-03-10 | Newtech Llc | Hydrophobic and oleophobic coating compositions |
| KR102489200B1 (ko) * | 2016-10-06 | 2023-01-16 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 표면 처리제 |
| CN106432738B (zh) * | 2016-10-12 | 2019-09-24 | 中国科学院化学研究所 | 一种含氟聚硅氮烷及其制备方法 |
| KR102015404B1 (ko) | 2016-12-08 | 2019-08-28 | 삼성에스디아이 주식회사 | 실리카 막 형성용 조성물, 실리카 막의 제조방법 및 실리카 막을 포함하는 전자소자 |
| CN111148804B (zh) * | 2017-09-27 | 2022-05-17 | 信越化学工业株式会社 | 含氟涂布剂组合物、表面处理剂和物品 |
| CN108329480B (zh) * | 2018-02-27 | 2020-12-25 | 广州弘海化工科技有限公司 | 改性聚硅氮烷预聚物、改性聚硅氮烷涂料及其使用方法 |
| KR102688455B1 (ko) * | 2018-03-14 | 2024-07-26 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 함불소 코팅제 조성물, 표면처리제 및 물품 |
| CN108795290B (zh) * | 2018-06-26 | 2021-03-02 | 广东美的厨房电器制造有限公司 | 涂料组合物和涂料以及涂层和氧化硅涂层以及具有涂层的制品和在基底表面形成涂层的方法 |
| KR20210102355A (ko) * | 2018-12-14 | 2021-08-19 | 메르크 파텐트 게엠베하 | 표면 코팅 조성물 |
| JP7103245B2 (ja) * | 2019-01-29 | 2022-07-20 | 信越化学工業株式会社 | ポリシロキサザン化合物およびその製造方法並びにこれを含む組成物および硬化物 |
| CN110128664A (zh) * | 2019-04-04 | 2019-08-16 | 华南理工大学 | 基于含氟化合物修饰的改性有机聚硅氮烷及其制备方法和应用 |
| US11724963B2 (en) | 2019-05-01 | 2023-08-15 | Corning Incorporated | Pharmaceutical packages with coatings comprising polysilazane |
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| JP2012532208A (ja) | 2012-12-13 |
| WO2011002668A1 (en) | 2011-01-06 |
| CN102471639A (zh) | 2012-05-23 |
| JP2012532207A (ja) | 2012-12-13 |
| US20100331487A1 (en) | 2010-12-30 |
| US8329830B2 (en) | 2012-12-11 |
| CN102471493B (zh) | 2013-10-30 |
| EP2449046A4 (en) | 2014-03-05 |
| EP2449000A4 (en) | 2014-03-26 |
| CN102471639B (zh) | 2014-07-23 |
| WO2011002666A1 (en) | 2011-01-06 |
| CN102471493A (zh) | 2012-05-23 |
| US20100331498A1 (en) | 2010-12-30 |
| EP2449000A1 (en) | 2012-05-09 |
| JP5616964B2 (ja) | 2014-10-29 |
| US8324324B2 (en) | 2012-12-04 |
| EP2449046A1 (en) | 2012-05-09 |
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