CN103113716B - Preparation method of dimer acid modified epoxy resin toughened carbon fiber prepreg - Google Patents
Preparation method of dimer acid modified epoxy resin toughened carbon fiber prepreg Download PDFInfo
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- CN103113716B CN103113716B CN201310032354.XA CN201310032354A CN103113716B CN 103113716 B CN103113716 B CN 103113716B CN 201310032354 A CN201310032354 A CN 201310032354A CN 103113716 B CN103113716 B CN 103113716B
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- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 63
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 59
- 239000002253 acid Substances 0.000 title claims abstract description 25
- 239000000539 dimer Substances 0.000 title claims abstract description 25
- 229920000049 Carbon (fiber) Polymers 0.000 title claims abstract description 24
- 239000004917 carbon fiber Substances 0.000 title claims abstract description 24
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 229920005989 resin Polymers 0.000 claims abstract description 24
- 239000011347 resin Substances 0.000 claims abstract description 24
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 15
- 238000002156 mixing Methods 0.000 claims abstract description 9
- 238000013329 compounding Methods 0.000 claims abstract description 7
- 239000004744 fabric Substances 0.000 claims abstract description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 16
- 239000004593 Epoxy Substances 0.000 claims description 13
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 10
- 229940106691 bisphenol a Drugs 0.000 claims description 8
- 238000007711 solidification Methods 0.000 claims description 7
- 230000008023 solidification Effects 0.000 claims description 7
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 7
- DGUJJOYLOCXENZ-UHFFFAOYSA-N 4-[2-[4-(oxiran-2-ylmethoxy)phenyl]propan-2-yl]phenol Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 DGUJJOYLOCXENZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002313 adhesive film Substances 0.000 claims description 6
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 6
- 238000007788 roughening Methods 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000003700 epoxy group Chemical group 0.000 claims description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 4
- 150000003672 ureas Chemical class 0.000 claims description 4
- SMOYQFCXYFMLQL-UHFFFAOYSA-M [P].[Br-].C(C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [P].[Br-].C(C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 SMOYQFCXYFMLQL-UHFFFAOYSA-M 0.000 claims description 3
- 229920003986 novolac Polymers 0.000 claims description 3
- AAJXNVMHMMPJOV-UHFFFAOYSA-N tetrabutyl(chloro)-$l^{5}-phosphane Chemical compound CCCCP(Cl)(CCCC)(CCCC)CCCC AAJXNVMHMMPJOV-UHFFFAOYSA-N 0.000 claims description 3
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 claims description 2
- RIWQWHDNZIGXOI-UHFFFAOYSA-M [P].[Br-].C1(=CC=CC=C1)[P+](CC)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [P].[Br-].C1(=CC=CC=C1)[P+](CC)(C1=CC=CC=C1)C1=CC=CC=C1 RIWQWHDNZIGXOI-UHFFFAOYSA-M 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 claims description 2
- 239000002131 composite material Substances 0.000 abstract description 6
- 229920001971 elastomer Polymers 0.000 abstract description 4
- 230000035699 permeability Effects 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000000034 method Methods 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 239000007888 film coating Substances 0.000 abstract 1
- 238000009501 film coating Methods 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 238000004513 sizing Methods 0.000 abstract 1
- 239000012745 toughening agent Substances 0.000 abstract 1
- 238000004804 winding Methods 0.000 abstract 1
- 239000000835 fiber Substances 0.000 description 13
- 239000007788 liquid Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 238000005520 cutting process Methods 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000003825 pressing Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000009736 wetting Methods 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 2
- -1 carbon fiber compound Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 230000008595 infiltration Effects 0.000 description 2
- 238000001764 infiltration Methods 0.000 description 2
- 230000003014 reinforcing effect Effects 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
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- Reinforced Plastic Materials (AREA)
Abstract
The invention provides a preparation method of a dimer acid modified epoxy resin toughened carbon fiber prepreg, which comprises the following steps: by taking a component of which the molecular structure is similar to that of a carbon fiber sizing agent as toughener, preparing a dimer acid modified epoxy resin through a pre-reaction method; adding reactants into the mixed epoxy resin, adding a latent curing agent, and evenly mixing to obtain a resin system for the prepreg; and coating the resin system through a film coating machine, and then compounding with carbon fibers or a fabric made therefrom to prepare the moderate-temperature curing prepreg having fine operability and adhesivity. Compared with the traditional rubber toughened prepreg, the invention can enhance the wettability of the resin system on carbon fibers, reduce the moisture permeability of the prepreg and simultaneously improve the toughness and impact resistance of the composite material, thus being suitable for manufacturing of a prepreg for winding formation.
Description
Technical field
The invention belongs to field of compound material, relate in particular to a kind of preparation method of dimer acid modified epoxy resin roughening carbon fiber prepreg.
Background technology
Most of carbon fiber is with the application of prepreg form in the world at present, and along with the expansion energetically of domestic carbon fibre, the downstream application market of exploitation prepreg is also imperative.The mechanical property of domestic carbon fibre monofilament meets or exceeds same kind of products at abroad, but due to domestic carbon fibre on the surface jelly and same kind of products at abroad difference larger, cause the surface wettability of domestic carbon fibre poor, therefore the wetting property of resin in process for manufacturing prepregs is had higher requirement.
Commercialization carbon fiber prepreg is main flow mainly with the epoxy-resin systems of intermediate temperature setting, for improving the shock resistance of matrix material prepared by it, the liquid nbr carboxyl terminal of many employings (CTBN) is toughness reinforcing, also has the resin flow adopting solid-state CTBN to reduce prepreg further.But rubber adds rear resin system viscosity to be increased, cause being deteriorated to the wetting property of carbon fiber, therefore the novel toughening mode of seeking epoxy resin for prepreg system is needed, to realize the abundant infiltration to carbon mono-filaments, especially for the infiltration of domestic carbon fibre, improve the interface cohesion of fiber and resin simultaneously.
Summary of the invention
For the toughness reinforcing epoxy resin for prepreg system of current techique to the poor deficiency of carbon fiber wetting property, the object of the invention is to, adopt the modified epoxy similar to carbon fiber cementing agent molecular structure as toughening element, a kind of intermediate temperature setting prepreg of dimer acid modified epoxy resin roughening is provided, obtain resin system to the good effect of impregnation of fiber, and improve resin to the sticking power of fiber and stripping strength.
For realizing object of the present invention, the preparation method of a kind of dimer acid modified epoxy resin roughening carbon fiber prepreg of the present invention, it is characterized in that: the dimeracid with active end carboxyl is reacted 2 ~ 6h by (1) under catalyst action with at epoxy resin 120 ~ 160 DEG C, obtain dimer acid modified epoxy resin, wherein the ratio of quality and the number of copies of dimeracid and epoxy resin is 40 ~ 60:60 ~ 40, relative to the quality sum 100 parts of the two, the mass fraction of catalyzer is 0.1 ~ 0.5 part; (2) above-mentioned dimer acid modified epoxy resin is added in blending epoxy, add latent curing agent again to mix, obtain prepreg resin system, wherein relative to 100 parts of blending epoxies, the mass fraction of dimer acid modified epoxy resin is 5 ~ 15 parts, and the mass fraction of latent curing agent is 5 ~ 10 parts; (3) prepreg resin system adopts adhesive film machine film, then via compounding machine and carbon fiber or its fabric compound, and the intermediate temperature setting prepreg of acquisition superior operational and stickiness.
The described viscosity with the dimeracid of active end carboxyl is 5000 ~ 8000cps.
The described epoxy resin reacted with dimeracid is one or more in bis-phenol A glycidyl ether, Bisphenol F glycidyl ether, dihydroxyphenyl propane D type epoxy resin, cycloaliphatic epoxy resin.
Described catalyzer is one or more of the quaternary alkylphosphonium salts such as triphenylphosphine, benzyltriphenylphosphonium bromide phosphorus, triphenyl ethyl phosphonium bromide phosphorus, tetrabutyl phosphorus chloride.
Described blending epoxy is two or more the combination in bis-phenol A glycidyl ether, Bisphenol F glycidyl ether, novolac epoxy, o-cresol epoxy resin, bisphenol-A phenolic epoxy resin.
Described latent curing agent is one or more in Dyhard RU 100, modified dicyandiamine, carbamide derivative, imdazole derivatives.
Described dimer acid modified epoxy resin, relative to 100 parts of blending epoxies, its preferred mass number is 5 ~ 10 parts.
The solidification value of the intermediate temperature setting prepreg of described superior operational and stickiness is 100 ~ 140 DEG C.
The present invention has advantage and the positively effect of following several respects:
(1) resin system is to the good wetting property of carbon fiber.Carbon fiber cementing agent is generally the emulsion of modified epoxy, and be typically employed in the epoxy resin end of the chain and introduce carboxyl to improve its hydrophilicity, therefore dimer acid modified epoxy resin has the molecular structure similar to carbon fiber cementing agent.Both excellent compatibility improve dimer acid modified epoxy resin roughening prepreg resin system to the effect of impregnation of carbon fiber, to improve in prepreg resin system to the sticking power of fiber and stripping strength simultaneously.
(2) moisture permeability of prepreg reduces.There is longer hydrophobicity alkane chain in dimeracid molecule segment, dimer acid modified epoxy resin is added in prepreg resin system, effectively can reduce the moisture permeability of prepreg, the use properties after prepreg storage can be ensured.
(3) good toughening effect.Containing longer flexibility fat segment in dimeracid molecular structure, in the cross-linked network after the solidification of prepreg resin system, the viscous deformation of resin matrix can be brought out, improve the toughness of resin matrix, and then improve the shock-resistance of matrix material.
Accompanying drawing explanation
Fig. 1 is the mechanical property of pour mass.
Fig. 2 is the interlaminar shear strength of matrix material.
Embodiment
Below in conjunction with specific embodiment, the present invention is further described.
Embodiment 1:
Take dimeracid 400g (viscosity is 5000cps) respectively, liquid bisphenol A glycidyl ether 600g and catalyzer triphenylphosphine 1g is placed in reactor, in 120 DEG C of reaction 6h under nitrogen protection, product is cooled, obtained dimer acid modified epoxy resin.Get 130g (massfraction is 5%) above-mentioned dimer acid modified epoxy resin, add liquid bisphenol A type epoxy resin 1560g, solid-state bisphenol A type epoxy resin 1040g, solidifying agent carbamide derivative 208g, strong stirring final vacuum extracts bubble, obtained epoxy resin for prepreg system.Poured into by this epoxy-resin systems in batten mould, 100 DEG C solidify 2 hours, prepare pour mass batten.Adopt adhesive film machine to prepare glued membrane above-mentioned resin system, then via compounding machine and carbon fibre fabric compound, prepare carbon fiber prepreg.By prepreg cutting laying, 100 DEG C of solidifications, 2 hours prepared layer pressing plates on vulcanizing press, interlaminar shear strength batten is prepared in cutting.Survey pour mass and composite material laminated board performance see Fig. 1 and Fig. 2 respectively.
Embodiment 2:
Take dimeracid 500g (viscosity is 6500cps), liquid bisphenol AD glycidyl ether 500g and catalyzer tetrabutyl phosphorus chloride 3g respectively and be placed in reactor; in 140 DEG C of reaction 4h under nitrogen protection; product is cooled, obtained dimer acid modified epoxy resin.Get 260g (massfraction is 10%) above-mentioned dimer acid modified epoxy resin, add liquid bisphenol f type epoxy resin 1380g, solid-state bisphenol A type epoxy resin 1220g, curing agent modified Dyhard RU 100 130g, strong stirring final vacuum extracts bubble, obtained epoxy resin for prepreg system.Poured into by this epoxy-resin systems in batten mould, 120 DEG C solidify 2 hours, prepare pour mass batten.Adopt adhesive film machine to prepare glued membrane above-mentioned resin system, then via compounding machine and carbon fiber compound, prepare Unidirectional fiber prepreg.By prepreg cutting laying, 120 DEG C of solidifications, 2 hours prepared layer pressing plates on vulcanizing press, interlaminar shear strength batten is prepared in cutting.Survey pour mass and composite material laminated board performance see Fig. 1 and Fig. 2 respectively.
Embodiment 3:
Take dimeracid 600g (viscosity is 8000cps), liquid bisphenol F glycidyl ether 400g and catalyzer benzyltriphenylphosphonium bromide phosphorus 5g respectively and be placed in reactor; in 160 DEG C of reaction 2h under nitrogen protection; product is cooled, obtained dimer acid modified epoxy resin.Get 390g (massfraction is 15%) above-mentioned dimer acid modified epoxy resin, add liquid novolac epoxy 1760g, solid-state bisphenol A type epoxy resin 840g, curing agent dicyandiamide 247g and imdazole derivatives 13g, strong stirring final vacuum extracts bubble, obtained epoxy resin for prepreg system.Poured into by this epoxy-resin systems in batten mould, 140 DEG C solidify 2 hours, prepare pour mass batten.Adopt adhesive film machine to prepare glued membrane above-mentioned resin system, then via compounding machine and carbon fiber compound, prepare Unidirectional fiber prepreg.By prepreg cutting laying, 140 DEG C of solidifications, 2 hours prepared layer pressing plates on vulcanizing press, interlaminar shear strength batten is prepared in cutting.Survey pour mass and composite material laminated board performance see Fig. 1 and Fig. 2 respectively.
Comparative example 1:
Take liquid nbr carboxyl terminal (CTBN) 400g (acrylonitrile content 26%), liquid bisphenol A glycidyl ether 600g and catalyzer triphenyl phosphorus 1g respectively and be placed in reactor; in 120 DEG C of reaction 6h under nitrogen protection; product is cooled, obtained rubber modified epoxy resin.Get 130g (massfraction is 5%) above-mentioned rubber modified epoxy resin, add liquid bisphenol A type epoxy resin 1560g, solid-state bisphenol A type epoxy resin 1040g, solidifying agent carbamide derivative 208g, strong stirring final vacuum extracts bubble, obtained epoxy resin for prepreg system.Poured into by this epoxy-resin systems in batten mould, 100 DEG C solidify 2 hours, prepare pour mass batten.Adopt adhesive film machine to prepare glued membrane above-mentioned resin system, then via compounding machine and carbon fibre fabric compound, prepare carbon fiber prepreg.By prepreg cutting laying, 100 DEG C of solidifications, 2 hours prepared layer pressing plates on vulcanizing press, interlaminar shear strength batten is prepared in cutting.Survey pour mass and composite material laminated board performance see Fig. 1 and Fig. 2 respectively.
The pour mass mechanical property of above-mentioned comparative example and each embodiment is shown in Fig. 1, and the interlaminar shear strength of composite material laminated board is shown in Fig. 2.
Claims (3)
1. the preparation method of a dimer acid modified epoxy resin roughening carbon fiber prepreg, it is characterized in that: the dimeracid with end pendant carboxylic group is reacted 2 ~ 6h with epoxy resin by (1) under catalyst action at 120 ~ 160 DEG C, obtain dimer acid modified epoxy resin, wherein the ratio of quality and the number of copies of dimeracid and epoxy resin is 40 ~ 60:60 ~ 40, relative to the quality sum 100 parts of the two, the mass fraction of catalyzer is 0.1 ~ 0.5 part; (2) above-mentioned dimer acid modified epoxy resin is added in blending epoxy, add latent curing agent again to mix, obtain prepreg resin system, wherein relative to 100 parts of blending epoxies, the mass fraction of dimer acid modified epoxy resin is 5 ~ 15 parts, and the mass fraction of latent curing agent is 5 ~ 10 parts; (3) prepreg resin system is adopted adhesive film machine film, then via compounding machine and carbon fiber or its fabric compound, the intermediate temperature setting prepreg of acquisition superior operational and stickiness;
The described viscosity with the dimeracid of end pendant carboxylic group is 5000 ~ 8000cps;
The described epoxy resin reacted with dimeracid is the combination of one or more in bis-phenol A glycidyl ether, Bisphenol F glycidyl ether, dihydroxyphenyl propane D type epoxy resin, cycloaliphatic epoxy resin;
Described catalyzer is the combination of one or more of triphenylphosphine, benzyltriphenylphosphonium bromide phosphorus, triphenyl ethyl phosphonium bromide phosphorus, tetrabutyl phosphorus chloride;
Described blending epoxy is two or more combination of bis-phenol A glycidyl ether, Bisphenol F glycidyl ether, novolac epoxy, o-cresol epoxy resin, bisphenol-A phenolic epoxy resin;
Described latent curing agent is the combination of one or more in Dyhard RU 100, modified dicyandiamine, carbamide derivative, imdazole derivatives.
2. preparation method according to claim 1, is characterized in that: described dimer acid modified epoxy resin, and relative to 100 parts of blending epoxies, its preferred mass number is 5 ~ 10 parts.
3. preparation method according to claim 1, is characterized in that: the solidification value of the intermediate temperature setting prepreg of described superior operational and stickiness is 100 ~ 140 DEG C.
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| CN103571157B (en) * | 2013-10-31 | 2016-04-06 | 广东生益科技股份有限公司 | Half flexibility coat copper plate of a kind of resin combination and making thereof |
| CN104693150A (en) * | 2015-02-17 | 2015-06-10 | 南通职业大学 | Flexible epoxy resin and preparation method thereof |
| CN104693148A (en) * | 2015-02-17 | 2015-06-10 | 南通职业大学 | Compound diacid-modified bisphenol-A epoxy resin and preparation method thereof |
| CN104987673A (en) * | 2015-08-05 | 2015-10-21 | 张家港康得新光电材料有限公司 | Epoxy resin composition for prepreg, carbon fiber prepreg and carbon fiber compound material |
| CN106893078A (en) * | 2015-12-18 | 2017-06-27 | 络合化学（上海）有限公司 | A kind of dimer acid modified epoxy resin and preparation method thereof |
| CN106433030B (en) * | 2016-09-05 | 2018-08-10 | 广东工业大学 | Epoxy resin is for wood and preparation method thereof |
| CN109504031A (en) * | 2018-10-31 | 2019-03-22 | 安徽绿之态新材料有限公司 | A kind of cellulose/melamino-formaldehyde compound resin and preparation method thereof |
| CN113214455B (en) * | 2021-06-25 | 2022-04-22 | 万华化学集团股份有限公司 | Toughening type water-based epoxy curing agent and preparation method and application thereof |
| CN114106519A (en) * | 2021-12-09 | 2022-03-01 | 中威北化科技有限公司 | Modified epoxy resin matrix material for wide temperature range and preparation method and application thereof |
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| JPH01185351A (en) * | 1988-01-18 | 1989-07-24 | Nissan Motor Co Ltd | Epoxy resin composition for carbon fiber reinforced material |
| JPH03203934A (en) * | 1989-12-28 | 1991-09-05 | Nippon Steel Chem Co Ltd | Epoxy resin prepreg |
| CN102746622A (en) * | 2012-07-26 | 2012-10-24 | 哈尔滨玻璃钢研究院 | Prepreg with moderate-temperature cured epoxy resin as substrate material and preparation method thereof |
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Denomination of invention: A preparation method of dimeric acid modified epoxy resin toughened carbon fiber prepreg Effective date of registration: 20220418 Granted publication date: 20150624 Pledgee: Weihai City Commercial Bank Limited by Share Ltd. high tech branch Pledgor: SINO-CF COMPOSITE SCI. & TECH. (WEIHAI) CO.,LTD. Registration number: Y2022980004141 |