CN113956441A - 一种模压自由基改性环氧树脂组成物 - Google Patents
一种模压自由基改性环氧树脂组成物 Download PDFInfo
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- CN113956441A CN113956441A CN202111271281.0A CN202111271281A CN113956441A CN 113956441 A CN113956441 A CN 113956441A CN 202111271281 A CN202111271281 A CN 202111271281A CN 113956441 A CN113956441 A CN 113956441A
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- Prior art keywords
- epoxy resin
- bisphenol
- peroxide
- molding
- resin composition
- 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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- 239000003822 epoxy resin Substances 0.000 title claims abstract description 46
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 46
- 239000000203 mixture Substances 0.000 title claims abstract description 29
- 150000003254 radicals Chemical class 0.000 title claims abstract description 11
- 238000007723 die pressing method Methods 0.000 title description 2
- 229920005989 resin Polymers 0.000 claims abstract description 35
- 239000011347 resin Substances 0.000 claims abstract description 35
- 238000000465 moulding Methods 0.000 claims abstract description 31
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 12
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 10
- 239000004848 polyfunctional curative Substances 0.000 claims abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 2
- -1 dimethylpentanedione dioxide Chemical compound 0.000 claims description 16
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 12
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 8
- 150000002978 peroxides Chemical class 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
- 239000011342 resin composition Substances 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 4
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 claims description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 3
- 230000009257 reactivity Effects 0.000 claims description 3
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical group CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 claims description 3
- WELSDMYWYMPCMH-UHFFFAOYSA-N (4-methyl-7-oxabicyclo[4.1.0]heptan-3-yl)methyl 7-oxabicyclo[4.1.0]heptane-3-carboxylate Chemical compound O1C2CC(C(CC21)C)COC(=O)C2CC1C(CC2)O1 WELSDMYWYMPCMH-UHFFFAOYSA-N 0.000 claims description 2
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 claims description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 2
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 claims description 2
- OWEYKIWAZBBXJK-UHFFFAOYSA-N 1,1-Dichloro-2,2-bis(4-hydroxyphenyl)ethylene Chemical compound C1=CC(O)=CC=C1C(=C(Cl)Cl)C1=CC=C(O)C=C1 OWEYKIWAZBBXJK-UHFFFAOYSA-N 0.000 claims description 2
- YDIZFUMZDHUHSH-UHFFFAOYSA-N 1,7-bis(ethenyl)-3,8-dioxatricyclo[5.1.0.02,4]oct-5-ene Chemical compound C12OC2C=CC2(C=C)C1(C=C)O2 YDIZFUMZDHUHSH-UHFFFAOYSA-N 0.000 claims description 2
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 claims description 2
- ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 claims description 2
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 claims description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 2
- CISIJYCKDJSTMX-UHFFFAOYSA-N 2,2-dichloroethenylbenzene Chemical compound ClC(Cl)=CC1=CC=CC=C1 CISIJYCKDJSTMX-UHFFFAOYSA-N 0.000 claims description 2
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 claims description 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 claims description 2
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 claims description 2
- FLMRHAZRTLGUHB-UHFFFAOYSA-N 2-[(3-pentadecylphenoxy)methyl]oxirane Chemical compound CCCCCCCCCCCCCCCC1=CC=CC(OCC2OC2)=C1 FLMRHAZRTLGUHB-UHFFFAOYSA-N 0.000 claims description 2
- DXEHULHXWHEJJD-UHFFFAOYSA-N 2-[(4-butylphenoxy)methyl]oxirane Chemical compound C1=CC(CCCC)=CC=C1OCC1OC1 DXEHULHXWHEJJD-UHFFFAOYSA-N 0.000 claims description 2
- HPILSDOMLLYBQF-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COC(CCC)OCC1CO1 HPILSDOMLLYBQF-UHFFFAOYSA-N 0.000 claims description 2
- SEFYJVFBMNOLBK-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane Chemical compound C1OC1COCCOCCOCC1CO1 SEFYJVFBMNOLBK-UHFFFAOYSA-N 0.000 claims description 2
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 claims description 2
- POLZHVHESHDZRD-UHFFFAOYSA-N 2-hydroxyethyl 2-methylprop-2-enoate;phosphoric acid Chemical compound OP(O)(O)=O.CC(=C)C(=O)OCCO POLZHVHESHDZRD-UHFFFAOYSA-N 0.000 claims description 2
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 claims description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 claims description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 2
- KOGSPLLRMRSADR-UHFFFAOYSA-N 4-(2-aminopropan-2-yl)-1-methylcyclohexan-1-amine Chemical compound CC(C)(N)C1CCC(C)(N)CC1 KOGSPLLRMRSADR-UHFFFAOYSA-N 0.000 claims description 2
- DLYLVPHSKJVGLG-UHFFFAOYSA-N 4-(cyclohexylmethyl)cyclohexane-1,1-diamine Chemical compound C1CC(N)(N)CCC1CC1CCCCC1 DLYLVPHSKJVGLG-UHFFFAOYSA-N 0.000 claims description 2
- BATCUENAARTUKW-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)-diphenylmethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BATCUENAARTUKW-UHFFFAOYSA-N 0.000 claims description 2
- UMPGNGRIGSEMTC-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 UMPGNGRIGSEMTC-UHFFFAOYSA-N 0.000 claims description 2
- IJWIRZQYWANBMP-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-propan-2-ylphenyl)propan-2-yl]-2-propan-2-ylphenol Chemical compound C1=C(O)C(C(C)C)=CC(C(C)(C)C=2C=C(C(O)=CC=2)C(C)C)=C1 IJWIRZQYWANBMP-UHFFFAOYSA-N 0.000 claims description 2
- PVFQHGDIOXNKIC-UHFFFAOYSA-N 4-[2-[3-[2-(4-hydroxyphenyl)propan-2-yl]phenyl]propan-2-yl]phenol Chemical compound C=1C=CC(C(C)(C)C=2C=CC(O)=CC=2)=CC=1C(C)(C)C1=CC=C(O)C=C1 PVFQHGDIOXNKIC-UHFFFAOYSA-N 0.000 claims description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
- ADAHGVUHKDNLEB-UHFFFAOYSA-N Bis(2,3-epoxycyclopentyl)ether Chemical compound C1CC2OC2C1OC1CCC2OC21 ADAHGVUHKDNLEB-UHFFFAOYSA-N 0.000 claims description 2
- 229930185605 Bisphenol Natural products 0.000 claims description 2
- VOWWYDCFAISREI-UHFFFAOYSA-N Bisphenol AP Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=CC=C1 VOWWYDCFAISREI-UHFFFAOYSA-N 0.000 claims description 2
- HTVITOHKHWFJKO-UHFFFAOYSA-N Bisphenol B Chemical compound C=1C=C(O)C=CC=1C(C)(CC)C1=CC=C(O)C=C1 HTVITOHKHWFJKO-UHFFFAOYSA-N 0.000 claims description 2
- GIXXQTYGFOHYPT-UHFFFAOYSA-N Bisphenol P Chemical compound C=1C=C(C(C)(C)C=2C=CC(O)=CC=2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 GIXXQTYGFOHYPT-UHFFFAOYSA-N 0.000 claims description 2
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004641 Diallyl-phthalate Substances 0.000 claims description 2
- ZFIVKAOQEXOYFY-UHFFFAOYSA-N Diepoxybutane Chemical compound C1OC1C1OC1 ZFIVKAOQEXOYFY-UHFFFAOYSA-N 0.000 claims description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 2
- 239000004593 Epoxy Substances 0.000 claims description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 2
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 claims description 2
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 claims description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Natural products CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 2
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- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 claims description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004841 bisphenol A epoxy resin Substances 0.000 claims description 2
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000004842 bisphenol F epoxy resin Substances 0.000 claims description 2
- UPIWXMRIPODGLE-UHFFFAOYSA-N butyl benzenecarboperoxoate Chemical group CCCCOOC(=O)C1=CC=CC=C1 UPIWXMRIPODGLE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 claims description 2
- VSRLTVWPYDTRQR-UHFFFAOYSA-N cyclohexane;oxirane Chemical compound C1CO1.C1CCCCC1 VSRLTVWPYDTRQR-UHFFFAOYSA-N 0.000 claims description 2
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 claims description 2
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- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 2
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- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 claims 1
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- RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 claims 1
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- 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
- C08G59/5026—Amines cycloaliphatic
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L63/10—Epoxy resins modified by unsaturated compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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- Macromonomer-Based Addition Polymer (AREA)
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Abstract
本发明公开了一种模压自由基改性环氧树脂组成物，其包括树脂、硬化剂及聚合反应起始剂；所述树脂的结构式为：
式Ⅰ中，Q、L各自独立地为
或
A为
或
M为H、
或
上述R1、R2、R3、R4各自独立地为H或C1‑C4的烷基。本发明提供的模压自由基改性环氧树脂组成物，树脂本体黏度低利于树脂含浸；可透过固化剂使树脂增稠成模压半成品，同时具热可塑性，因此纤维复合材料在模具内可透过加热塑形；本发明可在室温下进行增稠，不需提供额外热源和增稠剂。
Description
技术领域
本发明涉及一种模压自由基改性环氧树脂组成物，属于纤维模压制品及构件技术领域。
背景技术
模压不饱和聚酯树脂已广泛应用在制造模压制品及构件。但受限于材料特性，如力学性能较差、耐温性低、半成品黏度不易控制、与纤维结合性差等缺点，难以符合特殊应用领域需求；环氧树脂拥有体积收缩率低、黏着性佳、机械性质佳以及绝缘特性佳等优点，但现有环氧树脂系统模压加工特性差，至今也难以在市场上全面性使用。
模压成型工艺是一种十分成熟复合材料成型工艺，其中包含片状模塑料SMC及团状模塑料BMC。SMC是由浸润树脂糊的纤维组成，上下两面聚乙烯薄膜覆盖；配方组成由不饱和聚酯树脂、低收缩剂、固化剂、增稠剂、脱模剂、填料组成，经半自动化设备制成片材及收卷。BMC其主要原材料由短切玻璃纤维、不饱和聚酯树脂、填料，以及各种添加剂经充分混合而成的团状预浸料，属于热固性模塑料成型材料中的一种，适合模压成型、注射成型等成型方法。模压成型工艺具有机械化程度高、生产效率高、产品质量稳定、生产成本低等优点，为复合材料最为广泛应用工艺之一。
模压成型最主流材料为不饱和聚酯树脂，受限于既有材料特性，如力学性能较差、耐温性低、半成品黏度不易控制、纤维结合性差等缺点，难以符合特殊应用领域需求。环氧树脂拥有体积收缩率低、黏着性佳、机械性质佳以及绝缘特性佳等优点，但现有环氧树脂系统模压加工特性差，至今也难以在市场上全面性使用。
发明内容
本发明所要解决的技术问题是：现有模压成型主流材料——不饱和聚酯树脂，力学性能较差、耐温性低、半成品黏度不易控制、纤维结合性差等问题。
为了解决上述技术问题，本发明提供了一种模压自由基改性环氧树脂组成物，其包括树脂、硬化剂及聚合反应起始剂；所述树脂的结构式为：
式Ⅰ中，n为0至300的整数，优先为0至20的整数；Q、L各自独立地为
A为
M为H、
上述R1、R2、R3、R4各自独立地为H或C1-C4的烷基，优先为H或甲基。
优选地，所述树脂的结构式中，A为双酚A、双酚AP、双酚AF、双酚B、双酚BP、双酚C、双酚E、双酚F、双酚G、双酚M、双酚S、双酚P、双酚PH、双酚TMC、双酚Z，或者直接来源于选用的树脂为双酚A环氧树脂、双酚F环氧树脂、多官能环氧基环氧树脂、酚醛型环氧树脂、溴化型环氧树脂、邻-甲酚醛型环氧树脂、二酸改性型环氧树脂和橡胶增韧型环氧树脂中的至少一种，优先为双酚A结构。
优选地，所述的树脂由环氧树脂与不饱和羧酸进行开环反应，再以稀释剂稀释而成一种具有部分不饱和双键反应性的环氧树脂。
更优选地，所述环氧树脂的环氧官能基与不饱和羧酸的羧基的当量比值为30：1～1：5，优先为2：1～1：1.5。
更优选地，所述的不饱和羧酸为丙烯酸、甲基丙烯酸、卤化丙烯酸或其它含有双键的不饱和酸，优先为丙烯酸或甲基丙烯酸；不饱和羧酸在树脂中的质量百分比为30-100％，优先为60-90％。
更优选地，所述稀释剂为环氧辛烷、丁基缩水甘油醚、单氧双戊烯、苯基缩水甘油醚、对-丁基苯基缩水甘油醚、甲苯基缩水甘油醚、3-十五烷基苯基缩水甘油醚、二氧化丁二烯、二甲基戊烷二氧化物、二缩水甘油醚、丁二醇二缩水甘油醚、二乙二醇二缩水甘油醚、二氧化环己烯乙烯、二氧化萜二烯、双(2,3-环氧环戊基)醚、3,4-环氧基-6-甲基环己基甲基3,4-环氧基环己甲酸甲酯、甲基丙烯酸羟乙酯、甲基丙烯酸-2-羟丙酯、二乙烯苯二氧化物、二甲基丙烯酸乙二醇酯、2-环氧丙基苯基缩水甘油醚、2,6-二环氧丙烯苯基缩水甘油醚、苯乙烯、乙烯基甲苯、α-甲基苯乙烯、二氯苯乙烯、2-甲基-2-丙烯酸-2-烃乙基酯磷酸酯、丙烯酸酯、甲基丙烯酸酯、邻苯二甲酸二烯丙酯、己二醇二丙烯酸酯、三丙二醇二丙烯酸酯、三聚氰酸三烯丙酯、三烃甲基丙烷三甲基丙烯酸酯、三烃甲基丙烷三丙烯酸酯、甲基丙烯酸缩水甘油酯、烯丙基缩水甘油醚和环己烷乙烯单氧化物中的至少一种，优选为苯乙烯；稀释剂在树脂中的质量百分比为0-70％，优先为10-40％。
优选地，所述的硬化剂为直链脂肪族胺、环脂族胺和脂肪芳香族胺中的至少一种；硬化剂在树脂组成物中的质量百分比为1-50％，优选为3-20％。
更优选地，所述的直链脂肪族胺为乙二胺、双氰胺、4,4'-二氨基二苯基甲烷、4,4'-二氨基二环己基甲烷、1,2-二氨基环己烷、1,3-环己二甲胺、二乙烯三胺、三乙烯四胺、六亚甲基四胺和聚丙烯醚二胺中的至少一种；所述的环脂族胺为N-胺乙基哌嗪、薄荷烷二胺和异佛尔酮二胺中的至少一种；所述的脂肪芳香族胺为间苯二甲胺和聚酰胺中的至少一种。
优选地，所述的聚合反应起始剂为直链过氧化物、环脂族过氧化物和脂肪芳香族过氧化物中的至少一种，优选为氧化二苯甲酰或过氧苯甲酸三级丁脂；聚合反应起始剂在树脂组成物中的质量百分比为0.1-5％，优选为1-3％。
更优选地，所述的直链过氧化物为过氧化甲乙酮、过氧化二乙酰、二叔丁基过氧化物、过氧化乙酰丙酮和过氧化二叔丁烷中的至少一种；所述的环脂族过氧化物为过氧化环己酮和双(4-叔丁基环己基)过氧化二碳酸酯中的至少一种；所述的脂肪芳香族过氧化物为异丙苯过氧化氢、过氧化二苯甲酰、过氧化苯甲酸三级丁脂和过苯甲酸叔丁酯中的至少一种。
本发明提供了一种模压自由基改性环氧树脂组成物，其是一种兼具低黏度、模压工艺性佳及与碳纤维结合性佳，增稠工艺不须添加额外增稠剂，如氧化镁、氢氧化镁、氧化钙(石灰)、氢氧化钙及水。其适合用来制造纤维模压制品及构件的树脂组成物。
本发明提供的模压自由基改性环氧树脂组成物，树脂本体黏度低利于树脂含浸；可透过固化剂使树脂增稠成模压半成品，同时具热可塑性，因此纤维复合材料在模具内可透过加热塑形；有别于传统模压不饱和聚酯树脂必须搭配增稠剂使用，且熟化温度多在40～50℃，本发明的一种模压自由基改性环氧树脂组成物可以在室温下进行增稠，不需提供额外热源，其增稠工艺不需要额外添加增稠剂如氧化镁。因此本发明适合用来制造纤维模压制品及构件。
具体实施方式
为使本发明更明显易懂，兹以优选实施例，作详细说明如下。
实施例
本发明提供了一种用于碳纤维模压的树脂组成物，其包括树脂、硬化剂及聚合反应起始剂。按表1、表2的配方制备树脂组成物(如无特别说明，本发明中的各百分比指质量百分比，份数指质量分数)。实施例1-5中树脂的制备方法如下：
制程设备带有温控系统、加热系统、机械搅拌器及回流冷凝器，将选用的环氧树脂入反应釜，在搅拌状态下温度由室温升温至80℃，投入不饱和羧酸后持续搅拌至均匀，投入2,000ppm苯基膦作为反应触媒，加热至110℃，使反应进行至酸值低于10mg KOH/g；降温至110℃以下加入50ppm 4-叔丁基-1,2-苯二酚，搅拌均匀后加入稀释剂进行稀释，冷却过滤即得树脂。
表1
表2
将实施例1-5及对比例1、对比例2依据国际标准制备对应规格纯树脂试片，秤取配方量之树脂及硬化剂，投入桶里后，搅拌浆置于液面中央，转速220-270rpm，搅拌15mins。以树脂里看不到纹路为宜；关其搅拌设备后秤取配方量之增稠剂及聚合反应起始剂，投入桶里后，搅拌浆置于液面中央，转速220-270rpm，搅拌15mins，行浇注体制板，放置烘箱80℃一个小时，后100℃一个小时，后120℃一个小时，后140℃一个小时，完成机械性能测定，所得数据如表3所示。
表3
将实施例1-5及对比例1、对比例2进行半成品增稠测试，其测试方法为将各组份混合均匀后放置25℃环境，每8小时测试其黏度，完成半成品黏度测定，所得数据如表4所示。
表4
结合实施例1、2并结合表3可以看出，不饱和羧酸选用丙烯酸取代甲基丙烯酸提高其反应性有助于物性提升主要在于耐热性及模量。
结合实施例1、3并结合表3可以看出，提高不饱和羧酸比例，有助于物性提升主要在于耐热性。
结合实施例1、4并结合表3可以看出，提高硬化剂用量有助于物性提升主要在于提升产品韧性(体现在延伸率)。
结合实施例1、5并结合表3可以看出，提高环氧树脂EEW值，虽然会牺牲其耐热性，但有助于提升产品韧性(体现在延伸率)。
结合实施例1-5与对比例1并结合表3可以看出，本发明的一种模压自由基改性环氧树脂组成物在纯树脂机械性能表现上都能优于现有模压不饱和聚酯树脂。
结合实施例1-5与对比例1并结合表4可以看出，本发明的一种模压自由基改性环氧树脂组成物树脂初始黏度较现有模压不饱和聚酯树脂低，同时在半成品增稠性能上，能明显优于现有模压不饱和聚酯树脂。
结合实施例1-5与对比例2并结合表3-4可以看出，纵使环氧树脂拥有优异机械性能，但无法有效符合模压树脂半成品制成工艺需求。
综合以上测试结果，本发明的一种模压自由基改性环氧树脂组成物，树脂本体黏度低利于树脂含浸；可透过固化剂使树脂增稠成模压半成品，同时具热可塑性，因此纤维复合材料在模具内可透过加热塑形；有别于传统模压不饱和聚酯树脂必须搭配增稠剂使用，且熟化温度多在40～50℃，本发明的一种模压自由基改性环氧树脂组成物可以在室温下进行增稠，不需提供额外热源，其增稠工艺不需要额外添加增稠剂如氧化镁。因此本发明适合用来制造纤维模压制品及构件。
Claims (10)
1.一种模压自由基改性环氧树脂组成物，其特征在于，包括树脂、硬化剂及聚合反应起始剂；所述树脂的结构式为：
式Ⅰ中，n为0至300的整数；Q、L各自独立地为
A为
M为H、
上述R1、R2、R3、R4各自独立地为H或C1-C4的烷基。
2.如权利要求1所述的模压自由基改性环氧树脂组成物，其特征在于，所述树脂的结构式中，A为双酚A、双酚AP、双酚AF、双酚B、双酚BP、双酚C、双酚E、双酚F、双酚G、双酚M、双酚S、双酚P、双酚PH、双酚TMC、双酚Z，或者直接来源于选用的树脂为双酚A环氧树脂、双酚F环氧树脂、多官能环氧基环氧树脂、酚醛型环氧树脂、溴化型环氧树脂、邻-甲酚醛型环氧树脂、二酸改性型环氧树脂和橡胶增韧型环氧树脂中的至少一种。
3.如权利要求1所述的模压自由基改性环氧树脂组成物，其特征在于，所述的树脂由环氧树脂与不饱和羧酸进行开环反应，再以稀释剂稀释而成一种具有部分不饱和双键反应性的环氧树脂。
4.如权利要求3所述的模压自由基改性环氧树脂组成物，其特征在于，所述环氧树脂的环氧官能基与不饱和羧酸的羧基的当量比值为30：1～1：5。
5.如权利要求3所述的模压自由基改性环氧树脂组成物，其特征在于，所述的不饱和羧酸为丙烯酸、甲基丙烯酸、卤化丙烯酸或其它含有双键的不饱和酸；不饱和羧酸在树脂中的质量百分比为30-100％。
6.如权利要求3所述的模压自由基改性环氧树脂组成物，其特征在于，所述稀释剂为环氧辛烷、丁基缩水甘油醚、单氧双戊烯、苯基缩水甘油醚、对-丁基苯基缩水甘油醚、甲苯基缩水甘油醚、3-十五烷基苯基缩水甘油醚、二氧化丁二烯、二甲基戊烷二氧化物、二缩水甘油醚、丁二醇二缩水甘油醚、二乙二醇二缩水甘油醚、二氧化环己烯乙烯、二氧化萜二烯、双(2,3-环氧环戊基)醚、3,4-环氧基-6-甲基环己基甲基3,4-环氧基环己甲酸甲酯、甲基丙烯酸羟乙酯、甲基丙烯酸-2-羟丙酯、二乙烯苯二氧化物、二甲基丙烯酸乙二醇酯、2-环氧丙基苯基缩水甘油醚、2,6-二环氧丙烯苯基缩水甘油醚、苯乙烯、乙烯基甲苯、α-甲基苯乙烯、二氯苯乙烯、2-甲基-2-丙烯酸-2-烃乙基酯磷酸酯、丙烯酸酯、甲基丙烯酸酯、邻苯二甲酸二烯丙酯、己二醇二丙烯酸酯、三丙二醇二丙烯酸酯、三聚氰酸三烯丙酯、三烃甲基丙烷三甲基丙烯酸酯、三烃甲基丙烷三丙烯酸酯、甲基丙烯酸缩水甘油酯、烯丙基缩水甘油醚和环己烷乙烯单氧化物中的至少一种；稀释剂在树脂中的质量百分比为0-70％。
7.如权利要求1所述的模压自由基改性环氧树脂组成物，其特征在于，所述的硬化剂为直链脂肪族胺、环脂族胺和脂肪芳香族胺中的至少一种；硬化剂在树脂组成物中的质量百分比为1-50％。
8.如权利要求7所述的模压自由基改性环氧树脂组成物，其特征在于，所述的直链脂肪族胺为乙二胺、双氰胺、4,4'-二氨基二苯基甲烷、4,4'-二氨基二环己基甲烷、1,2-二氨基环己烷、1,3-环己二甲胺、二乙烯三胺、三乙烯四胺、六亚甲基四胺和聚丙烯醚二胺中的至少一种；所述的环脂族胺为N-胺乙基哌嗪、薄荷烷二胺和异佛尔酮二胺中的至少一种；所述的脂肪芳香族胺为间苯二甲胺和聚酰胺中的至少一种。
9.如权利要求1所述的模压自由基改性环氧树脂组成物，其特征在于，所述的聚合反应起始剂为直链过氧化物、环脂族过氧化物和脂肪芳香族过氧化物中的至少一种；聚合反应起始剂在树脂组成物中的质量百分比为0.1-5％。
10.如权利要求9所述的模压自由基改性环氧树脂组成物，其特征在于，所述的直链过氧化物为过氧化甲乙酮、过氧化二乙酰、二叔丁基过氧化物、过氧化乙酰丙酮和过氧化二叔丁烷中的至少一种；所述的环脂族过氧化物为过氧化环己酮和双(4-叔丁基环己基)过氧化二碳酸酯中的至少一种；所述的脂肪芳香族过氧化物为异丙苯过氧化氢、过氧化二苯甲酰、过氧化苯甲酸三级丁脂和过苯甲酸叔丁酯中的至少一种。
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| CN103013041A (zh) * | 2010-02-09 | 2013-04-03 | 上纬企业股份有限公司 | 一种环氧树脂组成物 |
| EP3255079A1 (de) * | 2016-06-10 | 2017-12-13 | Evonik Degussa GmbH | Epoxidharz-zusammensetzung enthaltend 2-(3,3,5-trimethylcyclohexyl)propan-1,3-diamin als härter |
| CN111793326A (zh) * | 2020-06-29 | 2020-10-20 | 河南东海复合材料有限公司 | 一种环氧玻纤基esmc片材的生产工艺 |
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| CN101186744A (zh) * | 2007-08-29 | 2008-05-28 | 上纬企业股份有限公司 | 一种环氧树脂及其用途 |
| CN103013041A (zh) * | 2010-02-09 | 2013-04-03 | 上纬企业股份有限公司 | 一种环氧树脂组成物 |
| EP3255079A1 (de) * | 2016-06-10 | 2017-12-13 | Evonik Degussa GmbH | Epoxidharz-zusammensetzung enthaltend 2-(3,3,5-trimethylcyclohexyl)propan-1,3-diamin als härter |
| CN111793326A (zh) * | 2020-06-29 | 2020-10-20 | 河南东海复合材料有限公司 | 一种环氧玻纤基esmc片材的生产工艺 |
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