CN116410443A - 共聚物、树脂、与复合材料 - Google Patents
共聚物、树脂、与复合材料 Download PDFInfo
- Publication number
- CN116410443A CN116410443A CN202210146890.1A CN202210146890A CN116410443A CN 116410443 A CN116410443 A CN 116410443A CN 202210146890 A CN202210146890 A CN 202210146890A CN 116410443 A CN116410443 A CN 116410443A
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- Prior art keywords
- copolymer
- epoxy compound
- resin
- composition
- hardener
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 82
- 239000011347 resin Substances 0.000 title claims abstract description 38
- 229920005989 resin Polymers 0.000 title claims abstract description 38
- 239000002131 composite material Substances 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 88
- 239000004593 Epoxy Substances 0.000 claims abstract description 77
- 239000004848 polyfunctional curative Substances 0.000 claims abstract description 36
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 239000000843 powder Substances 0.000 claims abstract description 17
- 239000000178 monomer Substances 0.000 claims description 21
- 229920000642 polymer Polymers 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 claims description 4
- RCJMVGJKROQDCB-UHFFFAOYSA-N 2-methylpenta-1,3-diene Chemical compound CC=CC(C)=C RCJMVGJKROQDCB-UHFFFAOYSA-N 0.000 claims description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000006681 (C2-C10) alkylene group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- PCCCQOGUVCNYOI-FNORWQNLSA-N (3e)-2,3-dimethylpenta-1,3-diene Chemical compound C\C=C(/C)C(C)=C PCCCQOGUVCNYOI-FNORWQNLSA-N 0.000 claims description 2
- 125000006557 (C2-C5) alkylene group Chemical group 0.000 claims description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 2
- OCTVDLUSQOJZEK-UHFFFAOYSA-N 4,5-diethylocta-1,3-diene Chemical compound CCCC(CC)C(CC)=CC=C OCTVDLUSQOJZEK-UHFFFAOYSA-N 0.000 claims description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 150000002927 oxygen compounds Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 36
- 238000003786 synthesis reaction Methods 0.000 description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 239000003999 initiator Substances 0.000 description 16
- 238000010992 reflux Methods 0.000 description 16
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- 230000009477 glass transition Effects 0.000 description 13
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000011247 coating layer Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 6
- 241000790917 Dioxys <bee> Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012779 reinforcing material Substances 0.000 description 3
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- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- LLPKQRMDOFYSGZ-UHFFFAOYSA-N 2-methyl-4-methylimidazole Natural products CC1=CN=C(C)N1 LLPKQRMDOFYSGZ-UHFFFAOYSA-N 0.000 description 2
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 2
- 229910052582 BN Inorganic materials 0.000 description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 2
- 238000004891 communication Methods 0.000 description 2
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 2
- -1 cycloalkylene radicals Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
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- 230000002787 reinforcement Effects 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 1
- FUSNOPLQVRUIIM-UHFFFAOYSA-N 4-amino-2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-n-[3-(trifluoromethyl)phenyl]pyrimidine-5-carboxamide Chemical compound O=C1NC(C)(C)CN1C(N=C1N)=NC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FUSNOPLQVRUIIM-UHFFFAOYSA-N 0.000 description 1
- 229940073735 4-hydroxy acetophenone Drugs 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000012668 chain scission Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012493 hydrazine sulfate Substances 0.000 description 1
- 229910000377 hydrazine sulfate Inorganic materials 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000006467 substitution reaction 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
Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/28—Di-epoxy compounds containing acyclic nitrogen atoms
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
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- C08G59/26—Di-epoxy compounds heterocyclic
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G59/226—Mixtures of di-epoxy compounds
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- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
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- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/38—Epoxy compounds containing three or more epoxy groups together with di-epoxy compounds
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- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
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- C08G59/4014—Nitrogen containing compounds
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- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4207—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof aliphatic
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
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- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5046—Amines heterocyclic
- C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
- C08G59/508—Amines heterocyclic containing only nitrogen as a heteroatom having three nitrogen atoms in the ring
- C08G59/5086—Triazines; Melamines; Guanamines
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
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- C08G59/686—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing nitrogen
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- 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
- C09D1/00—Coating compositions, e.g. paints, varnishes or lacquers, based on inorganic substances
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- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
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- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
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- C09D7/61—Additives non-macromolecular inorganic
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- 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
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Abstract
Description
技术领域
本揭露关于共聚物与包含共聚物的树脂,更特别关于共聚物的单体种类。
背景技术
5G移动通信网络已在2020年开始启用,带动蓝牙无线通信、服务器、和云端物联网的兴起。由于电磁波段频率越来越高,高频用低介电损耗材料的规格要求也越严苛。通信产品用电路板和IC载板趋向高速化与高密度整合化,因此PCB基板需求除了低介电常数与低介电损耗外,也必须兼具高导热性功能。
综上所述,目前亟需新的聚合物,以同时兼具高热传、低热膨胀系数、低介电常数、与低介电损耗等特性。
发明内容
本揭露一实施例提供的树脂,是由组成物O反应而成。组成物O包括第一共聚物与第二共聚物,其中第一共聚物是由组成物I反应而成,其中组成物I包括:(a)第一环氧化合物,其结构为其中R1是单键、-O-、(b)第二环氧化合物,其不同于(a)第一环氧化合物;以及(c)硬化剂,其中第二共聚物是由组成物II反应而成,其中组成物II包括:(d)芳香性单体、其寡聚物、或其聚合物;以及(e)脂肪族单体、其寡聚物、或其聚合物,其中芳香性单体的化学结构为/>其中R4为CH3,且n=0-4;R5是单键、-O-、/> R7是C2-10的烷撑基;每一R8各自为单键、-O-、 且o是1-70;每一R6各自为/>其中R9是H或CH3,且R10是C1-10的烷撑基。
具体实施方式
在一些实施例中,(a)第一环氧化合物与(b)第二环氧化合物的当量比为100:1至100:120、100:2至100:120、100:2至100:100或100:50至100:120。在适当的比例之下,整体树脂倾向达成较低的热膨胀系数,且保有良好的树脂导热特性。
在一些实施例中,(a)第一环氧化合物加上(b)第二环氧化合物的当量总和与(c)硬化剂的当量比为100:70至100:120或100:90至100:100。在适当的比例之下,树脂硬化较完全,且可减少因加热断链而造成过多极性基团导致的产物电性劣化。
本揭露一实施例提供的复合材料,包括:上述的共聚物;以及无机粉体,其中共聚物与无机粉体的重量比例为100:30至100:300。无机粉体可为氮化铝、氮化硼、氧化铝、氢氧化镁、二氧化硅,或上述的组合。无机粉体可进一步降低共聚物的介电常数、介电损耗、与热膨胀系数。在适当的比例之下,则粉体较容易均匀分散在共聚物中。
本揭露一实施例提供的树脂,是由组成物O反应而成。组成物O包括第一共聚物与第二共聚物。第一共聚物为上述的共聚物,其可由组成物I共聚而成,在此不重述。第二共聚物是由组成物II共聚而成,其中组成物II包括:(d)芳香性单体、其寡聚物、或其聚合物;以及(e)脂肪族单体、其寡聚物、或其聚合物,其中芳香性单体的化学结构为其中R4为CH3,且n=0-4;R5是单键、-O-、 R7是C2-10的烷撑基;每一R8各自为单键、-O-、/> 且o是1-70;每一R6各自为/>其中R9是H或CH3,且R10是C1-10的烷撑基。
在一些实施例中,脂肪族单体是1,3-丁二烯、异戊二烯、1,3-戊二烯、2,3-二甲基-1,3-丁二烯、2-甲基-1,3-戊二烯、2,3-二甲基-1,3-戊二烯、4,5-二乙基-1,3-辛二烯、 其中R11是C1-12的烷撑基或环烷撑基;R12是/>每一R13各自是H或CH3;R14是C2-5的烷撑基;每一R15各自是H或CH3;以及q=1-70。
在一些实施例中,(d)芳香性单体、其寡聚物、或其聚合物与(e)脂肪族单体、其寡聚物、或其聚合物的摩尔比例(d/e)为1:2至99:1。若(d)芳香性单体、其寡聚物、或其聚合物的比例过低,则第二共聚物的传热性不足,连带使树脂的传热性不足。
此外,关于第二共聚物的实施方式与具体细节,可参考申请人稍早申请的中国专利申请202110695971.2。
在一些实施例中,第一共聚物与该第二共聚物的重量比为100:5至100:120。若第二共聚物的比例过高,则树脂的热膨胀系数过大。
本揭露一实施例提供的复合材料,包括:上述的树脂;以及无机粉体,其中树脂与无机粉体的重量比例为100:30至100:300。无机粉体可为氮化铝、氮化硼、氧化铝、氢氧化镁、二氧化硅,或上述的组合。无机粉体可进一步降低树脂的介电常数、介电损耗、与热膨胀系数。若无机粉体的用量过高,则粉体不易均匀分散在树脂中。
在一实施例中,上述共聚物或树脂或复合材料可用于接着剂或封装材料。在一实施例中,可将含共聚物或树脂或复合材料的涂料(含有机溶剂)涂布至载体上,接着烘干涂料以形成涂层。在一些实施例中,载体可为铜箔、聚合物膜(如聚酰亚胺膜、聚对苯二甲酸乙二酯膜、或其他聚合物膜)、或类似物。上述涂层具有热传导性高(传热系数≥0.28W/mK,甚至传热系数≥0.4W/mK)、热膨胀系数低(CTE≤60ppm/℃,甚至CTE≤50ppm/℃)、高频介电常数低(Dk@10GHz≤3.2,甚至Dk@10GHz≤2.8)、以及高频介电损失低(Df@10GHz≤0.007甚至Df@10GHz≤0.005)等特性。
在一实施例中,可将含有涂层于其上的载体对向压合,且涂层彼此接触。当载体为铜箔时,压合后的结构即所谓的铜箔基板。在一实施例中,上述压合制程的压力介于5Kg至50Kg之间,温度介于150℃至250℃之间,且历时1小时至10小时之间。
在一实施例中,可将补强材含浸于涂料中(A-stage),接着将含浸后的补强材置入50.0℃至500.0℃的烘箱,烘干涂料以形成胶片(B-stage)。在一实施例中,补强材包括玻璃、陶瓷、碳材、树脂、或上述的组合,且补强材的形状为纤维、粉体、片状物、编织物、或上述的组合。举例来说,补强材可为玻纤布。上述胶片具有热传导性高、热膨胀系数低、高频介电常数低、以及高频介电损失低等特性。在一实施例中,可将一或多个胶片夹设于铜箔之间,再压合成铜箔基板,在一实施例中,压合制程的压力介于5Kg至50Kg之间,温度介于150℃至250℃之间,且历时1小时至10小时之间。
为让本揭露的上述内容和其他目的、特征、和优点能更明显易懂,下文特举出较佳实施例,作详细说明如下:
[实施例]
在下述实施例中,涂层的传热系数的量测标准为ASTM-D5470,热膨胀系数的量测标准为ASTM-2113-04,且介电常数与介电损耗的量测标准为JIS-C2565。
合成例1
取4,4’-二羟基联苯(186g,1mol)、环氧氯丙烷(370g,2.4mol)、与四正丁基溴化铵(17g,0.2mol)于氮气下加热至90℃并反应2小时。接着加入40%氢氧化钠水溶液1公升,持续反应1.5小时。将反应结果倒入2公升甲醇使产物析出,搅拌后过滤收集固体,水洗固体后烘干,得产物283克,上述产物的结构如下:
合成例2
取4,4’-二羟基苯乙酮(214g,1mol)、环氧氯丙烷(370g,2.4mol)、与四正丁基溴化铵(17g,0.2mol)于氮气下加热至90℃并反应2小时。接着加入40%氢氧化钠水溶液1公升,持续反应1.5小时。将反应结果倒入2公升甲醇溶剂使产物析出,搅拌后过滤收集固体,水洗固体后烘干。得产物312克,上述产物的结构如下:
合成例3
取4-羟基苯乙酮(136g,1mol)、环氧氯丙烷(370g,2.4mol)、与四正丁基溴化铵(8.4g,0.1mol),于氮气下加热至90℃反应2小时。接着加入2M氢氧化钠水溶液700毫升,搅拌隔夜后过滤收集固体,水洗固体后烘干。得中间产物198克(收率95%)。将中间产物加入硫酸肼(64g,0.49mol)、三乙胺(49g,0.49mol)、与乙醇(200g)后,回流反应5小时。反应结束后降至室温,待产物析出后过滤收集固体,以乙醇与去离子水清洗固体,并烘干得产物(120克),上述产物的结构如下:
实施例1
取373g的合成例1的产物、6.8g的蒽型双环氧基化合物(购自DIC的4032D)、227g的8000-65T硬化剂(购自DIC)、与3g的起始剂DMAP(4-(Dimethylamino)pyridine,购自Aldrich)溶于1000mL的THF溶剂中,回流反应2小时以得共聚物。合成例1的产物与4032D的摩尔比为98:2。(a)第一环氧化合物与(b)第二环氧化合物的当量比为100:2.04。(a)第一环氧化合物加上(b)第二环氧化合物的当量总和与(c)硬化剂的当量比约100:90。将上述共聚物涂布成膜后,烘干形成厚约100μm的涂层的传热系数为0.428W/mK,热膨胀系数为43.9ppm/℃,且玻璃转化温度Tg为179℃。4032D的结构如下:8000-65T的结构如下:其中R3为苯基或萘基,k=0-1,且l=0-2。
实施例2
取326g的合成例2的产物、27.2g的蒽型双环氧基化合物4032D、196g的8000-65T硬化剂、与3g的起始剂DMAP溶于1000mL的THF溶剂中,回流反应2小时以得共聚物。合成例2的产物与4032D的摩尔比为90:10。(a)第一环氧化合物与(b)第二环氧化合物的当量比为100:11.11。(a)第一环氧化合物加上(b)第二环氧化合物的当量总和与(c)硬化剂的当量比约为100:90。将上述共聚物涂布成膜后,烘干形成厚约100μm的涂层的传热系数为0.385W/mK,热膨胀系数为38.1ppm/℃,且玻璃转化温度Tg为186℃。
实施例3
取380g的合成例3的产物、272g的蒽型双环氧基化合物4032D、356g的8000-65T硬化剂、与3g的起始剂DMAP溶于1000mL的THF溶剂中,回流反应2小时以得共聚物。合成例3的产物与4032D的摩尔比为50:50。(a)第一环氧化合物与(b)第二环氧化合物的当量比为100:100。(a)第一环氧化合物加上(b)第二环氧化合物的当量总和与(c)硬化剂的当量比约为100:90。将上述共聚物涂布成膜后,烘干形成厚约100μm的涂层的传热系数为0.315W/mK,热膨胀系数为36.4ppm/℃,且玻璃转化温度Tg为190℃。
实施例4
取187g的合成例1的产物、204g的合成例2的产物、6.8g的蒽型双环氧基化合物4032D、227g的8000-65T硬化剂、与3g的起始剂DMAP溶于1000mL的THF溶剂中,回流反应2小时以得共聚物。合成例1的产物、合成例2的产物、与4032D的摩尔比为49:49:2。(a)第一环氧化合物与(b)第二环氧化合物的当量比为100:2.04。(a)第一环氧化合物加上(b)第二环氧化合物的当量总和与(c)硬化剂的当量比约为100:90。将上述共聚物涂布成膜后,烘干形成厚约100μm的涂层的传热系数为0.403W/mK,热膨胀系数为44.7ppm/℃,且玻璃转化温度Tg为176℃。
实施例5
取163g的合成例2的产物、190g的合成例3的产物、27.2g的蒽型双环氧基化合物4032D、196g的8000-65T硬化剂、与3g的起始剂DMAP溶于1000mL的THF溶剂中,回流反应2小时以得共聚物。合成例2的产物、合成例3的产物、与4032D的摩尔比为45:45:10。(a)第一环氧化合物与(b)第二环氧化合物的当量比为100:11.11。(a)第一环氧化合物加上(b)第二环氧化合物的当量总和与(c)硬化剂的当量比约为100:90。将上述共聚物涂布成膜后,烘干形成厚约100μm的涂层的传热系数为0.355W/mK,热膨胀系数为40.1ppm/℃,玻璃转化温度Tg为183℃。
实施例6
取149g的合成例1的产物、190g的合成例3的产物、272g的蒽型双环氧基化合物4032D、356g的8000-65T硬化剂、与3g的起始剂DMAP溶于1000mL的THF溶剂中,回流反应2小时以得共聚物。合成例1的产物、合成例3的产物、与4032D的摩尔比为25:25:50。(a)第一环氧化合物与(b)第二环氧化合物的当量比为100:100。(a)第一环氧化合物加上(b)第二环氧化合物的当量总和与(c)硬化剂的当量比约为100:90。将上述共聚物涂布成膜后,烘干形成厚约100μm的涂层的传热系数为0.301W/mK,热膨胀系数为38.2ppm/℃,玻璃转化温度Tg为187℃。
合成例4
取4,4’-二羟基联苯(186g,1mol)、甲基丙烯酸酐(370g,2.4mol)、碳酸氢钠(17g,0.2mol)于氮气下加热至80℃并反应2小时。反应完成后加入2M氢氧化钠水溶液1公升,搅拌隔夜后过滤产物,水洗后烘干得产物306克。上述产物的结构如下:
比较例1
取402g的合成例4的产物、8g的双马来酰亚胺(购自大和化成工业株式会社的BMI-TMH)、与4g的自由基起始剂101(2,5-Bis(tert-butylperoxy)-2,5-dimethylhexane,购自Aldrich)溶于1000mL的环己酮中,回流反应2小时以得共聚物。合成例4的产物与BMI-TMH的摩尔比为98:2。将上述共聚物涂布成膜后,烘干形成厚约100μm的涂层的传热系数为0.416W/mK,热膨胀系数为78.4ppm/℃,玻璃转化温度Tg为171℃。BMI-TMH的结构如下:
实施例7
取303g的实施例1的共聚物、30g的比较例1的共聚物、与7g的起始剂2E4MZ(2-Ethyl-4-Methyl Imidazole,购自Aldrich)溶于1000mL的THF溶剂中,回流反应2小时以形成树脂。实施例1的共聚物与比较例1的共聚物的重量比为91:9。将上述树脂涂布成膜后,烘干形成厚约100μm的涂层的传热系数为0.41W/mK,热膨胀系数为47.6ppm/℃,高频介电常数(Dk@10GHz)为2.86,且高频介电损耗(Df@10GHz)为0.0067。
实施例8
取240g的实施例1的共聚物、60g的比较例1的共聚物、与6g的起始剂2E4MZ溶于1000mL的THF溶剂中,回流反应2小时以形成树脂。实施例1的共聚物与比较例1的共聚物的重量比为80:20。将上述树脂涂布成膜后,烘干形成厚约100μm的涂层的传热系数为0.385W/mK,热膨胀系数为51.3ppm/℃,高频介电常数(Dk@10GHz)为2.8,且高频介电损耗(Df@10GHz)为0.0059。
实施例9
取204g的实施例1的共聚物、204g的比较例1的共聚物、与8g的起始剂2E4MZ溶于1000mL的THF溶剂中,回流反应2小时以形成树脂。实施例1的共聚物与比较例1的共聚物的重量比为50:50。将上述树脂涂布成膜后,烘干形成厚约100μm的涂层的传热系数为0.388W/mK,热膨胀系数为55.6ppm/℃,高频介电常数(Dk@10GHz)为2.72,且高频介电损耗(Df@10GHz)为0.0052。
实施例10
与实施例9类似,差别在于进一步将175g的氧化硅添加至树脂中,以形成复合材料。氧化硅与树脂的重量比例为约30:70。将复合材料涂布成膜后,烘干形成厚约100μm的涂层的传热系数为0.398W/mK,热膨胀系数为43.2ppm/℃,高频介电常数(Dk@10GHz)为2.74,且高频介电损耗(Df@10GHz)为0.0049。
实施例11
与实施例9类似,差别在于进一步将408g的氧化硅添加至树脂中,以形成复合材料。氧化硅与树脂的重量比例为约50:50。将复合材料涂布成膜后,烘干形成厚约100μm的涂层的传热系数为0.425W/mK,热膨胀系数为28.2ppm/℃,高频介电常数(Dk@10GHz)为2.71,且高频介电损耗(Df@10GHz)为0.0046。
实施例12
与实施例9类似,差别在于进一步将952g的氧化硅添加至树脂中,以形成复合材料。氧化硅与树脂的重量比例为约70:30。将复合材料涂布成膜后,烘干形成厚约100μm的涂层的传热系数为0.447W/mK,热膨胀系数为18.8ppm/℃,高频介电常数(Dk@10GHz)为2.58,且高频介电损耗(Df@10GHz)为0.004。
实施例13
取326g的合成例2的产物、170g的蒽型四环氧基化合物4710(购自DIC)、94g的三嗪硬化剂(购自Acros)、与3g的起始剂2E4MZ溶于1000mL的THF溶剂中,回流反应2小时以得共聚物。合成例2的产物与4710的摩尔比为50:50。(a)第一环氧化合物与(b)第二环氧化合物的当量比为100:50。(a)第一环氧化合物加上(b)第二环氧化合物的当量总和与(c)硬化剂的当量比约为100:100。将上述共聚物涂布成膜后,烘干形成厚约100μm的涂层的传热系数为0.284W/mK,热膨胀系数为42.6ppm/℃,玻璃转化温度Tg为164℃。4710的结构如下:三嗪硬化剂的结构如下:/>
实施例14
取489g的合成例2的产物、85g的蒽型四环氧基化合物4710、94g的三嗪硬化剂、与3.5g的起始剂2E4MZ溶于1000mL的THF溶剂中,回流反应2小时以得共聚物。合成例2的产物与4710的摩尔比为75:25。(a)第一环氧化合物与(b)第二环氧化合物的当量比为100:16.67。(a)第一环氧化合物加上(b)第二环氧化合物的当量总和与(c)硬化剂的当量比约为100:100。将上述共聚物涂布成膜后,烘干形成厚约100μm的涂层的传热系数为0.302W/mK,热膨胀系数为55.7ppm/℃,玻璃转化温度Tg为157℃。
实施例15
取326g的合成例2的产物、272g的蒽型多环氧基化合物9900(购自DIC)、94g的三嗪硬化剂、与3.5g的起始剂2E4MZ溶于1000mL的THF溶剂中,回流反应2小时以得共聚物。合成例2的产物与9900的摩尔比为50:50。(a)第一环氧化合物与(b)第二环氧化合物的当量比为100:100。(a)第一环氧化合物加上(b)第二环氧化合物的当量总和与(c)硬化剂的当量比约为100:100。将上述共聚物涂布成膜后,烘干形成厚约100μm的涂层的传热系数为0.298W/mK,热膨胀系数为51.4ppm/℃,玻璃转化温度Tg为159℃。蒽型多环氧基化合物9900的结构如下:其中R2是CnH2n+1,n=1-5,x=1-3。
实施例16
取326g的合成例2的产物、190g的二环氧基化合物YX4000(购自三菱化学)、94g的三嗪硬化剂、与3g的起始剂2E4MZ溶于1000mL的THF溶剂中,回流反应2小时以得共聚物。合成例2的产物与YX4000的摩尔比为50:50。(a)第一环氧化合物与(b)第二环氧化合物的当量比为100:100。(a)第一环氧化合物加上(b)第二环氧化合物的当量总和与(c)硬化剂的当量比约为100:90。将上述共聚物涂布成膜后,烘干形成厚约100μm的涂层的传热系数为0.275W/mK,热膨胀系数为62.8ppm/℃,玻璃转化温度Tg为153℃。YX4000的结构如下:
实施例17
取373g的合成例2的产物、188g的二环氧基化合物1010A(购自真时科技材料)、266g的酸酐硬化剂(购自Acros)、与3g的起始剂2EZ(2-Ethyl-Imidazole,购自Aldrich)溶于1000mL的THF溶剂中,回流反应2小时以得共聚物。合成例2的产物与1010A的摩尔比为50:50。(a)第一环氧化合物与(b)第二环氧化合物的当量比为100:100。(a)第一环氧化合物加上(b)第二环氧化合物的当量总和与(c)硬化剂的当量比约为100:90。将上述共聚物涂布成膜后,烘干形成厚约100μm的涂层的传热系数为0.268W/mK,热膨胀系数为82.5ppm/℃,玻璃转化温度Tg为147℃。1010A的结构如下:其中y=0-2。酸酐硬化剂的结构如下:/>
实施例18
取373g的合成例2的产物、188g的二环氧基化合物1010A(购自真时科技材料)、83g的二酸硬化剂、与3g的起始剂2MZ(2-Methyl-Imidazole,购自Aldrich)溶于1000mL的THF溶剂中,回流反应2小时以得共聚物。合成例2的产物与1010A的摩尔比为50:50。(a)第一环氧化合物与(b)第二环氧化合物的当量比为100:100。(a)第一环氧化合物加上(b)第二环氧化合物的当量总和与(c)硬化剂的当量比约为100:90。将上述共聚物涂布成膜后,烘干形成厚约100μm的涂层的传热系数为0.263W/mK,热膨胀系数为78.4ppm/℃,玻璃转化温度Tg为145℃。二酸硬化剂的结构如下:
虽然本揭露已以数个较佳实施例揭露如上,然其并非用以限定本揭露,任何所属技术领域中具有通常知识者,在不脱离本揭露的精神和范围内,当可作任意的更动与润饰,因此本揭露的保护范围当视后附的申请专利范围所界定者为准。
Claims (14)
4.如权利要求1所述的共聚物,其中所述第一环氧化合物与所述第二环氧化合物的当量比为100:1至100:120。
6.如权利要求1所述的共聚物,其中所述第一环氧化合物加上所述第二环氧化合物的当量总和与所述硬化剂的当量比为100:70至100:120。
7.一种复合材料,包括:
权利要求1所述的共聚物;以及
无机粉体;
其中所述共聚物与所述无机粉体的重量比例为100:30至100:300。
8.一种树脂,是由组成物O反应而成,
其中该组成物O包括第一共聚物与第二共聚物;
其中该第一共聚物是由组成物I反应而成,且该组成物I包括:
(b)第二环氧化合物,其不同于所述第一环氧化合物;以及
(c)硬化剂,
其中该第二共聚物是由组成物II共聚而成,其中该组成物II包括:
(d)芳香性单体、其寡聚物、或其聚合物;以及
(e)脂肪族单体、其寡聚物、或其聚合物,
其中R4为CH3,且n=0-4;
R7是C2-10的烷撑基;
12.如权利要求8所述的树脂,其中所述芳香性单体、其寡聚物、或其聚合物与所述脂肪族单体、其寡聚物、或其聚合物的摩尔比例(d/e)为1:2至99:1。
13.如权利要求8所述的树脂,其中该第一共聚物与该第二共聚物的重量比为100:5至100:120。
14.一种复合材料,包括:
权利要求8所述的树脂;以及
无机粉体;
其中所述树脂与所述无机粉体的重量比例为100:30至100:300。
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