TWI564342B - Crosslinking auxiliaries and their applications - Google Patents
Crosslinking auxiliaries and their applications Download PDFInfo
- Publication number
- TWI564342B TWI564342B TW103105845A TW103105845A TWI564342B TW I564342 B TWI564342 B TW I564342B TW 103105845 A TW103105845 A TW 103105845A TW 103105845 A TW103105845 A TW 103105845A TW I564342 B TWI564342 B TW I564342B
- Authority
- TW
- Taiwan
- Prior art keywords
- crosslinking
- acrylate
- meth
- sealing material
- resin composition
- Prior art date
Links
- 238000004132 cross linking Methods 0.000 title claims description 57
- 229920001038 ethylene copolymer Polymers 0.000 claims description 19
- 239000011342 resin composition Substances 0.000 claims description 17
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 15
- 229920000193 polymethacrylate Polymers 0.000 claims description 15
- 239000003566 sealing material Substances 0.000 claims description 14
- 230000005855 radiation Effects 0.000 claims description 11
- 239000012948 isocyanate Substances 0.000 claims description 10
- 150000002513 isocyanates Chemical class 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 8
- 239000003431 cross linking reagent Substances 0.000 claims description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 6
- 239000012776 electronic material Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000007334 copolymerization reaction Methods 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 28
- 239000005038 ethylene vinyl acetate Substances 0.000 description 9
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 9
- -1 among them Polymers 0.000 description 8
- 150000001451 organic peroxides Chemical class 0.000 description 8
- 239000012752 auxiliary agent Substances 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000000178 monomer Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000007789 sealing Methods 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 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000004840 adhesive resin Substances 0.000 description 2
- 229920006223 adhesive resin Polymers 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 2
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- KCZQSKKNAGZQSZ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)-1,3,5-triazin-2,4,6-trione Chemical compound O=C=NCCCCCCN1C(=O)N(CCCCCCN=C=O)C(=O)N(CCCCCCN=C=O)C1=O KCZQSKKNAGZQSZ-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- SMLNDVNTPWRZJH-UHFFFAOYSA-N 1-chloro-4-(trimethoxymethyl)dodecane Chemical compound ClCCCC(C(OC)(OC)OC)CCCCCCCC SMLNDVNTPWRZJH-UHFFFAOYSA-N 0.000 description 1
- QWQNFXDYOCUEER-UHFFFAOYSA-N 2,3-ditert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1C(C)(C)C QWQNFXDYOCUEER-UHFFFAOYSA-N 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- MFAWEYJGIGIYFH-UHFFFAOYSA-N 2-[4-(trimethoxymethyl)dodecoxymethyl]oxirane Chemical compound C(C1CO1)OCCCC(C(OC)(OC)OC)CCCCCCCC MFAWEYJGIGIYFH-UHFFFAOYSA-N 0.000 description 1
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 1
- LBIHNTAFJVHBLJ-UHFFFAOYSA-N 3-(triethoxymethyl)undec-1-ene Chemical compound C(=C)C(C(OCC)(OCC)OCC)CCCCCCCC LBIHNTAFJVHBLJ-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- FMKFGJVTEQCSLH-UHFFFAOYSA-N N1C=CC2=CC=CC=C12.OCC(CO)(CO)CO Chemical compound N1C=CC2=CC=CC=C12.OCC(CO)(CO)CO FMKFGJVTEQCSLH-UHFFFAOYSA-N 0.000 description 1
- XJDCHDFUMGSEHD-UHFFFAOYSA-N NCCCC(C(OC)(OC)OC)CCCCCCCC Chemical compound NCCCC(C(OC)(OC)OC)CCCCCCCC XJDCHDFUMGSEHD-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- GMJZOMKCRBNEED-UHFFFAOYSA-N [(5-benzhydrylperoxy-2,5-dimethylhexan-2-yl)peroxy-phenylmethyl]benzene Chemical compound CC(C)(CCC(C)(OOC(C1=CC=CC=C1)C1=CC=CC=C1)C)OOC(C1=CC=CC=C1)C1=CC=CC=C1 GMJZOMKCRBNEED-UHFFFAOYSA-N 0.000 description 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 description 1
- YPCHGLDQZXOZFW-UHFFFAOYSA-N [2-[[4-methyl-3-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]carbonylamino]phenyl]carbamoyloxymethyl]-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound CC1=CC=C(NC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C)C=C1NC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C YPCHGLDQZXOZFW-UHFFFAOYSA-N 0.000 description 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000002313 adhesive film Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000012773 agricultural material Substances 0.000 description 1
- MOVRNJGDXREIBM-UHFFFAOYSA-N aid-1 Chemical compound O=C1NC(=O)C(C)=CN1C1OC(COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)COP(O)(=O)OC2C(OC(C2)N2C3=C(C(NC(N)=N3)=O)N=C2)CO)C(O)C1 MOVRNJGDXREIBM-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 238000003339 best practice Methods 0.000 description 1
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000001447 compensatory effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000013013 elastic material Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 230000005251 gamma ray Effects 0.000 description 1
- 238000001631 haemodialysis Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000322 hemodialysis Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229920000831 ionic polymer Polymers 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Chemical class 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000012460 protein solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PNWOTXLVRDKNJA-UHFFFAOYSA-N tert-butylperoxybenzene Chemical compound CC(C)(C)OOC1=CC=CC=C1 PNWOTXLVRDKNJA-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
- C09J123/26—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers modified by chemical after-treatment
- C09J123/36—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers modified by chemical after-treatment by reaction with compounds containing nitrogen, e.g. by nitration
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/20—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
- C08K5/34924—Triazines containing cyanurate groups; Tautomers thereof
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/04—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof adapted as photovoltaic [PV] conversion devices
- H01L31/042—PV modules or arrays of single PV cells
- H01L31/048—Encapsulation of modules
- H01L31/0481—Encapsulation of modules characterised by the composition of the encapsulation material
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2331/00—Characterised by the use of copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, or carbonic acid, or of a haloformic acid
- C08J2331/02—Characterised by the use of omopolymers or copolymers of esters of monocarboxylic acids
- C08J2331/04—Homopolymers or copolymers of vinyl acetate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
- C09J123/02—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
- C09J123/04—Homopolymers or copolymers of ethene
- C09J123/08—Copolymers of ethene
- C09J123/0846—Copolymers of ethene with unsaturated hydrocarbons containing other atoms than carbon or hydrogen atoms
- C09J123/0853—Vinylacetate
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Power Engineering (AREA)
- Engineering & Computer Science (AREA)
- General Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Physics & Mathematics (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Computer Hardware Design (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Photovoltaic Devices (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Sealing Material Composition (AREA)
Description
本發明為關於交聯助劑及其應用,詳細係關於包含被廣泛使用之三烯丙基異氰酸酯(TAIC)之交聯助劑及其應用(例如:太陽電池用密封材料等)。
以往以來,作為被使用於各種的電子材料模組之組裝之密封材料,提案著將乙烯系共聚物作為基底材料,並於此中調配作為交聯劑之有機過氧化物之樹脂組成物(專利文獻1)。
又,提案著一種太陽電池用黏著薄片,其係由乙烯系共聚物100重量份及有機過氧化物0.05~0.5重量份所構成之太陽電池用黏著薄片,且含有具有丙烯醯基或甲基丙烯醯基之任一者或二者合計為4個以上之多官能單體(專利文獻2)。
更,提案著一種太陽電池用密封膜,其係包含乙烯不飽和酯共聚物、交聯劑、及交聯助劑之太陽電池用密封膜,且作為前述交聯助劑,包含多元醇之多官能(甲基)丙烯酸酯與TAIC(專利文獻3)。
然而,TAIC係已知作為使交聯性高分子硬化以得到成形體時為有效的交聯助劑。特別是,將乙烯乙酸乙烯酯共聚物以有機過氧化物做交聯時,作為交聯助劑TAIC為必須,且可提供具有高度透明性、黏著性、耐熱性、柔軟性之太陽電池用密封材料。然而,具有乙烯乙酸乙烯酯共聚物等之極性基之高分子,即使是使用TAIC做交聯之情形,其絕緣性(體積固有電阻值)亦無法稱為充分。依據上述提案,即使是與多元醇之多官能(甲基)丙烯酸酯併用之情形,依然有改善的空間。
專利文獻1:日本國特開昭60-226589號公報
專利文獻2:日本國特開2007-123488號公報
專利文獻3:日本國特開2009-135200號公報
本發明有鑑於上述情形,目的為提供一種交聯助劑,其係含有TAIC之交聯助劑,且一邊維持以往的交聯乙烯乙酸乙烯酯共聚物所具有的透明性、黏著性、耐熱性、柔軟性,同時可得到對絕緣性為優越的黏著性樹脂組成物。
本發明為達成上述目的而進行深入之檢討結果,得到藉由併用特定的化合物與TAIC則能夠達成上述目的之見解。
本發明係依據上述見解所完成者,且由關於交聯助劑與其應用之一連串相關發明所構成,如下述般。
(1)一種交聯助劑,其特徵係由胺基甲酸酯聚(甲基)丙烯酸酯與三烯丙基異氰酸酯之組合所構成。
(2)如上述(1)所記載之交聯助劑,其係使用於乙烯共聚物用。
(3)一種熱交聯用樹脂組成物,其特徵係將交聯劑與如上述(1)所記載之交聯助劑調配於乙烯共聚物中所構成。
(4)一種放射線交聯用樹脂組成物,其特徵係將如上述(1)所記載之交聯助劑調配於乙烯共聚物用中所構成。
(5)一種密封材料,其特徵係由如上述(3)所記載之熱交聯用樹脂組成物所構成。
(6)一種密封材料,其特徵係由如上述(4)所記載之放射交聯用樹脂組成物所構成。
(7)如上述(5)或(6)所記載之密封材料,其係用於太陽電池。
依據本發明之交聯助劑,可一邊維持以往的交聯乙烯乙酸乙烯酯共聚物所具有的透明性、黏著性、耐熱性、柔軟性,同時可得到對絕緣性為優越的黏著性樹脂組成物。
本發明之交聯助劑係由胺基甲酸酯聚(甲基)丙烯酸酯與TAIC之組合所構成。
胺基甲酸酯聚(甲基)丙烯酸酯係可例如由有機異氰酸酯與含有羥基之(甲基)丙烯酸酯來合成。在胺基甲酸酯聚(甲基)丙烯酸酯之中,較佳為分子量高者。作為數平均分子量係以1000以上,較佳為1200以上。其上限通常為10,000。
作為有機異氰酸酯,係在一分子內具有2個以上異氰酸酯基之化合物,且作為有機基可舉例:直鏈、分支、環狀之脂肪族烴基、芳香族烴基、異氰脲酸酯等之雜環基。作為有機異氰酸酯之具體例,可舉例:1,6-六亞甲基二異氰酸酯、異佛酮二異氰酸酯、甲苯胺二異氰酸酯、MDI(二苯基甲烷二異氰酸酯)、氫化MDI、伸苯二
甲基二異氰酸酯、1,6-六亞甲基二異氰酸酯三聚體、異佛酮二異氰酸酯三聚體等。
含有羥基之(甲基)丙烯酸酯,係在一分子中具有1個以上羥基之(甲基)丙烯酸酯。例如:多元醇之(甲基)丙烯酸酯,作為其具體例,可舉例:三羥甲丙烷二(甲基)丙烯酸酯、新戊四醇三(甲基)丙烯酸酯、二新戊四醇四(甲基)丙烯酸酯、三新戊四醇(甲基)丙烯酸酯、聚烷基二醇(甲基)丙烯酸酯、聚乙二醇(甲基)丙烯酸酯、聚伸烷基二醇(甲基)丙烯酸酯、甘油二(甲基)丙烯酸酯、聚醇(甲基)丙烯酸酯等之含有羥基之(甲基)丙烯酸酯。含有羥基之(甲基)丙烯酸酯係可為單一的丙烯酸酯,或為混合此等者亦可。
作為胺基甲酸酯聚(甲基)丙烯酸酯市售品之例,可舉例:共榮社化學公司製的「UA-306H」、「UA-306T」、「UA-306I」、「UA-510H」、DAICEL-CYTEC公司製的「KRM7864」、「KRM8452」、「EB1290」、「EB1290K」、「EB5129」、新中村化學公司製的「U-6HA」、「U-6LPA」、「U-15HA」、「UA-33H」、「UA-122P」、日本合成公司製的「UV7600B」、「UV7605B」、「UV7610B」、「UV7620EA」等。
胺基甲酸酯聚(甲基)丙烯酸酯與TAIC之使用比率(重量比)係通常為1:9~9:1,較佳為1:1~1:4。
本發明之交聯助劑只要無損及本發明之效果,亦可包含多官能(甲基)丙烯酸酯。多官能(甲基)丙烯酸酯係在一分子中具有2個以上(甲基)丙烯醯基,較佳為具有3個以上者。具體而言,可舉例:三羥甲丙烷三(甲基)丙烯酸酯、二羥甲丙烷四(甲基)丙烯酸酯、新戊四醇三(甲基)丙烯酸酯、新戊四醇四(甲基)丙烯酸酯、二新戊四醇五(甲基)丙烯酸酯、二新戊四醇六(甲基)丙烯酸酯等。
本發明之交聯助劑,即使在放射線交聯或熱交聯之任何的態樣中都能夠使用。即,調配於交聯性聚合體中所得之樹脂組成物係可作為放射線交聯用樹脂組成物,或作為熱交聯用樹脂組成物來使用。
作為交聯性聚合體,特別以乙烯共聚物為較佳。乙烯共聚物係將乙烯作為主成分,且為與此者能共聚合的單體之共聚物,作為單體,可示例有:乙烯酯、不飽和羧酸酯、不飽和羧酸及其金屬鹽、不飽和矽化合物、α-烯烴等。作為可共聚合的單體,較佳為極性單體。作為乙烯共聚物之具體例,可示例有:如乙烯乙酸乙烯酯共聚物之乙烯‧乙烯酯共聚物、如乙烯‧丙烯酸甲酯共聚物‧乙烯‧丙烯酸異丁酯‧甲基丙烯酸共聚物之乙烯‧不飽和
羧酸酯共聚物及其多離子聚合物,於此等之中,特佳為乙烯乙酸乙烯酯共聚物。
在放射線交聯用樹脂組成物或熱交聯用樹脂組成物中,本發明之交聯助劑的調配量(胺基甲酸酯聚(甲基)丙烯酸酯與TAIC的總量),相對於乙烯共聚物100重量份,通常為0.1~3.0重量份,較佳為0.5~2.0重量份。又,若作為其他的交聯助劑而併用多官能(甲基)丙烯酸酯時,其調配量,相對於乙烯共聚物100重量份,通常為0.1~3.0重量份,較佳為0.5~2.0重量份。
在熱交聯中,交聯劑係與交聯助劑一起使用。作為該交聯劑,一般可使用有機過氧化物。作為有機過氧化物,只要是在加硫條件下會產生過氧自由基之周知有機過氧化物即可,並無特別限定。可舉例如:二-t-丁基過氧化物、二異丙苯基過氧化物、2,5-二甲基-2,5-二(苯甲醯基過氧基)己烷、2,5-二甲基-2,5-二(t-丁基過氧基)己烷、t-丁基過氧基-2-乙基己基-單碳酸酯、1,1-雙(t-丁基過氧基)-3,5,5-三甲基環己烷、2,5-二甲基己烷-2,5-二羥基過氧化物、t-丁基異丙苯基過氧化物、α,α'-雙(t-丁基過氧基)-p-二異丙苯、2,5-二甲基-2,5-二(t-丁基過氧基)己烷-3、過氧化苯甲醯、t-丁基過氧化苯等。
交聯劑的調配量係依乙烯共聚物之種類而不同,相對於乙烯共聚物100重量份,通常為0.6~5重量
份,較佳為1~2重量份。尚,當照射放射線並使做交聯時,並未必需要有機過氧化物。
在放射線交聯用樹脂組成物或熱交聯用樹脂組成物中,可使用例如:補強制、填充劑、可塑劑、加工助劑、潤滑劑、顏料、老化防止劑、偶合劑、紫外線吸收劑、酸受劑等之任意的添加劑。
作為老化防止劑之具體例,可舉例:二-t-丁基-P-甲酚、季戊四醇-肆[3-(3,5-二-t-丁基-4-羥苯基)丙酸酯]、2,2'亞甲基雙(2-甲基-6-t-丁基苯基)、雙(2,2,6,6-四甲基-4-六氫吡基)癸二酸酯、N,N'-己烷-1,6-二基雙[3-(3,5-二-tert-丁基-4-羥苯基)丙醯胺基]、雙(2,2,6,6-四甲基-4-六氫吡基)癸二酸酯、氫醌單甲基醚、甲基氫醌等。
作為偶合劑之具體例,可舉例:γ-氯丙基三甲氧基矽烷、乙烯基三乙氧基矽烷、乙烯基-參-(β-甲氧基乙氧基)矽烷、γ-甲基丙烯醯氧基丙基三甲氧基矽烷、β-(3,4-乙氧基環己基)乙基三甲氧基矽烷、γ-縮水甘油氧基丙基三甲氧基矽烷、γ-巰基丙基三甲氧基矽烷、γ-胺基丙基三甲氧基矽烷、N-β-(胺基乙基)-γ-胺基丙基三甲氧基矽烷等。
作為紫外線吸收劑之具體例,可舉例:2-羥基-4-n-辛氧基二苯甲酮、2,2-羥基6-4,4-二甲氧基二苯甲酮、2-(2’-羥基-5-甲基苯基)苯并三唑、p-t-丁基苯基水楊酸酯等。
作為酸受劑之具體例,可舉例:氫氧化鎂、氫氧化鈣、氧化鎂、氧化鋅等。
上述添加劑之比例量,相對於乙烯共聚物100重量份,通常為10重量份以下,較佳為5重量份以下。
作為被使用於放射線交聯之放射線,可利用加速電子線、X線、α線、β線、γ線等。照射線量係依所使用之交聯性彈性物等而不同,但通常為0.1~500kGy。熱交聯係使用例如射出成型機或加壓成型機等,藉由以150℃~200℃、加熱約2~30分鐘而可得到成形體。因應所需,之後以150℃~200℃下加熱1~10小時來進行二次交聯亦可。前述乙烯共聚物組成物之交聯,特別以藉由有機過氧化物來做交聯為較佳。
上述乙烯共聚物組成物,除了食品、醫藥品、工業藥品、農業等各種的包裝材料、各種的黏著膜、太陽電池、液晶、發光二極體、有機EL等之各種電氣材料之密封膜以外,於血液透析、血漿成分分離、蛋白溶液之脫鹽、分餾、濃縮、果汁之濃縮、廢水處理等之領域中亦為有用。特別以作為被使用於各種的電子材料模組之組裝之密封材料為有用。另外,若在如太陽電池之密封材料般具有相當的厚度之樣態下來使用之密封劑之情形時,因為無法經由紫外線、電子線之硬化,故可使用熱交聯用樹脂組成物。
接著,舉實施例更詳細說明本發明,但本發明並無任何限制於此等中。
藉由開放滾筒(open roll),將以下表1所表示之各成分進行混練。作為EVA(乙烯乙酸乙烯酯共聚物)係使用乙酸乙烯基含有量為32重量%者。作為交聯助劑1,使用日本化成(股)製的TAIC,作為交聯助劑2,將表2所表示之化合物隨每個各別例變更使用。將所得到的組成物,以150℃進行熱壓製交聯(一次交聯)後可得到厚度1mm的薄片。將薄片之體積固有電阻值,以表3所表示之方法進行測定。將結果表示於表4。
作為有機異氰酸酯使用異佛酮二異氰酸酯、作為含有羥基之(甲基)丙烯酸酯使用季戊四醇三丙烯酸酯來合成胺基甲酸酯聚(甲基)丙烯酸酯。將所得到的胺基甲酸酯聚(甲基)丙烯酸酯之數平均分子量以GPC進行測定。測定條件係如下般。
機器名:TOSOH公司製HLC-8020GPC
管柱:TSKgel Super HM-N 2根+HZ1000 1根
載體:THF
流量:0.6ml/min
濃度:約0.4%
檢測器:RI
管柱溫度:40℃
檢量線:標準聚苯乙烯
將上述胺基甲酸酯聚(甲基)丙烯酸酯作為交聯助劑2來使用,與實施例1~3及比較例1~4以相同之方式來製作成EVA薄片並測定體積電阻率。將結果表示於表5。
Claims (11)
- 一種使用於乙烯共聚物用之交聯助劑,其特徵係由胺基甲酸酯聚(甲基)丙烯酸酯與三烯丙基異氰酸酯之組合所構成。
- 一種熱交聯用樹脂組成物,其特徵係將交聯劑、與由胺基甲酸酯聚(甲基)丙烯酸酯與三烯丙基異氰酸酯之組合所構成之交聯助劑調配於乙烯共聚物中所構成。
- 一種放射線交聯用樹脂組成物,其特徵係將由胺基甲酸酯聚(甲基)丙烯酸酯與三烯丙基異氰酸酯之組合所構成之交聯助劑調配於乙烯共聚物中所構成。
- 一種密封材料,其特徵係由如請求項2所記載之熱交聯用樹脂組成物所構成。
- 一種密封材料,其特徵係由如請求項3所記載之放射線交聯用樹脂組成物所構成。
- 如請求項4或5所記載之密封材料,其係用於太陽電池用。
- 一種電子材料模組,其係使用如請求項4或5所記載之密封材料經組裝而成。
- 一種電子材料模組之製造方法,其特徵係使用如請求項4或5所記載之密封材料來進行組裝。
- 一種太陽電池,其係使用如請求項4或5所記載之密封材料經組裝而成。
- 一種太陽電池之製造方法,其特徵係使用如請求項4或5所記載之密封材料來進行組裝。
- 一種乙烯共聚物組成物,其特徵係將胺基甲酸酯聚(甲基)丙烯酸酯與三烯丙基異氰酸酯調配於乙烯共聚物中所構成。
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- 2014-02-21 CN CN201480009093.2A patent/CN105164198B/zh active Active
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JPH0931220A (ja) * | 1995-07-24 | 1997-02-04 | Matsushita Electric Works Ltd | プリプレグの製造方法 |
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CN105164198B (zh) | 2017-05-31 |
JPWO2014129573A1 (ja) | 2017-02-02 |
EP2960291A1 (en) | 2015-12-30 |
JP5888466B2 (ja) | 2016-03-22 |
US20150353784A1 (en) | 2015-12-10 |
WO2014129573A1 (ja) | 2014-08-28 |
CN105164198A (zh) | 2015-12-16 |
TW201446877A (zh) | 2014-12-16 |
KR102092570B1 (ko) | 2020-03-24 |
KR20150119845A (ko) | 2015-10-26 |
EP2960291B1 (en) | 2018-12-26 |
EP2960291A4 (en) | 2016-09-28 |
US9428672B2 (en) | 2016-08-30 |
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