JP2020527180A - 樹脂硬化剤系の改善 - Google Patents
樹脂硬化剤系の改善 Download PDFInfo
- Publication number
- JP2020527180A JP2020527180A JP2020500869A JP2020500869A JP2020527180A JP 2020527180 A JP2020527180 A JP 2020527180A JP 2020500869 A JP2020500869 A JP 2020500869A JP 2020500869 A JP2020500869 A JP 2020500869A JP 2020527180 A JP2020527180 A JP 2020527180A
- Authority
- JP
- Japan
- Prior art keywords
- curing agent
- agent system
- epoxy resin
- fiber
- alkylbenzene
- 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.)
- Granted
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- 229920005989 resin Polymers 0.000 title claims abstract description 42
- 239000011347 resin Substances 0.000 title claims abstract description 41
- 230000006872 improvement Effects 0.000 title description 3
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 83
- 239000003822 epoxy resin Substances 0.000 claims abstract description 82
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 74
- 239000000203 mixture Substances 0.000 claims abstract description 70
- 150000004982 aromatic amines Chemical class 0.000 claims abstract description 47
- 239000000463 material Substances 0.000 claims abstract description 43
- -1 alkylbenzene diamine Chemical class 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 30
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims abstract description 29
- 230000008569 process Effects 0.000 claims abstract description 28
- 239000003733 fiber-reinforced composite Substances 0.000 claims abstract description 24
- 238000002347 injection Methods 0.000 claims abstract description 21
- 239000007924 injection Substances 0.000 claims abstract description 21
- 239000000835 fiber Substances 0.000 claims abstract description 19
- 238000004519 manufacturing process Methods 0.000 claims abstract description 17
- 239000004848 polyfunctional curative Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- OHQOKJPHNPUMLN-UHFFFAOYSA-N n,n'-diphenylmethanediamine Chemical group C=1C=CC=CC=1NCNC1=CC=CC=C1 OHQOKJPHNPUMLN-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000003700 epoxy group Chemical group 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 239000000919 ceramic Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 229910002804 graphite Inorganic materials 0.000 claims description 3
- 239000010439 graphite Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- OLOYYTRIQLNXIG-UHFFFAOYSA-N ClC1=C(N(CC)CC)C=CC=C1.C=C(C)N(C1=CC=CC=C1)C Chemical compound ClC1=C(N(CC)CC)C=CC=C1.C=C(C)N(C1=CC=CC=C1)C OLOYYTRIQLNXIG-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- MFFOPVVOGPQPMG-UHFFFAOYSA-N N,N'-bis(3-chloro-2-ethylphenyl)-N,N'-diethylmethanediamine Chemical compound C(N(C1=C(C(=CC=C1)Cl)CC)CC)N(C1=C(C(=CC=C1)Cl)CC)CC MFFOPVVOGPQPMG-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 239000004760 aramid Substances 0.000 claims description 2
- 229920006231 aramid fiber Polymers 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- VOLFIDSFKZJSNJ-UHFFFAOYSA-N n,n'-diethyl-n,n'-bis(2-ethylphenyl)methanediamine Chemical compound C=1C=CC=C(CC)C=1N(CC)CN(CC)C1=CC=CC=C1CC VOLFIDSFKZJSNJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000002131 composite material Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 10
- 239000012779 reinforcing material Substances 0.000 description 9
- 229920003319 Araldite® Polymers 0.000 description 8
- 239000011342 resin composition Substances 0.000 description 8
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- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 6
- 239000002657 fibrous material Substances 0.000 description 6
- 239000011148 porous material Substances 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
- AOFIWCXMXPVSAZ-UHFFFAOYSA-N 4-methyl-2,6-bis(methylsulfanyl)benzene-1,3-diamine Chemical compound CSC1=CC(C)=C(N)C(SC)=C1N AOFIWCXMXPVSAZ-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 238000012669 compression test Methods 0.000 description 3
- 239000011258 core-shell material Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000001721 transfer moulding Methods 0.000 description 3
- PVXVWWANJIWJOO-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-N-ethylpropan-2-amine Chemical compound CCNC(C)CC1=CC=C2OCOC2=C1 PVXVWWANJIWJOO-UHFFFAOYSA-N 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- OEVGZRDJQXPUOU-UHFFFAOYSA-N 2-(oxiran-2-ylmethyl)-1h-imidazole Chemical compound N=1C=CNC=1CC1CO1 OEVGZRDJQXPUOU-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 2
- QMMZSJPSPRTHGB-UHFFFAOYSA-N MDEA Natural products CC(C)CCCCC=CCC=CC(O)=O QMMZSJPSPRTHGB-UHFFFAOYSA-N 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 239000004917 carbon fiber Substances 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000011151 fibre-reinforced plastic Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- FJWZMLSQLCKKGV-UHFFFAOYSA-N 1-(2-ethylphenyl)propane-1,1-diamine Chemical class CCC1=CC=CC=C1C(N)(N)CC FJWZMLSQLCKKGV-UHFFFAOYSA-N 0.000 description 1
- HGXVKAPCSIXGAK-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine;4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N.CCC1=CC(C)=C(N)C(CC)=C1N HGXVKAPCSIXGAK-UHFFFAOYSA-N 0.000 description 1
- SEFYJVFBMNOLBK-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane Chemical compound C1OC1COCCOCCOCC1CO1 SEFYJVFBMNOLBK-UHFFFAOYSA-N 0.000 description 1
- OQRCDIPTOADXMP-UHFFFAOYSA-N 2-chloro-n,n-diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1Cl OQRCDIPTOADXMP-UHFFFAOYSA-N 0.000 description 1
- NBMQGZICMNFIGL-UHFFFAOYSA-N 3,4-bis(oxiran-2-ylmethyl)naphthalene-1,2-diol Chemical compound C1OC1CC=1C(O)=C(O)C2=CC=CC=C2C=1CC1CO1 NBMQGZICMNFIGL-UHFFFAOYSA-N 0.000 description 1
- UUMVFGKPRBQAJM-UHFFFAOYSA-N 4-[(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1.C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 UUMVFGKPRBQAJM-UHFFFAOYSA-N 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920003226 polyurethane urea Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G59/5033—Amines aromatic
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C70/00—Shaping composites, i.e. plastics material comprising reinforcements, fillers or preformed parts, e.g. inserts
- B29C70/003—Shaping composites, i.e. plastics material comprising reinforcements, fillers or preformed parts, e.g. inserts characterised by the matrix material, e.g. material composition or physical properties
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C70/00—Shaping composites, i.e. plastics material comprising reinforcements, fillers or preformed parts, e.g. inserts
- B29C70/04—Shaping composites, i.e. plastics material comprising reinforcements, fillers or preformed parts, e.g. inserts comprising reinforcements only, e.g. self-reinforcing plastics
- B29C70/28—Shaping operations therefor
- B29C70/30—Shaping by lay-up, i.e. applying fibres, tape or broadsheet on a mould, former or core; Shaping by spray-up, i.e. spraying of fibres on a mould, former or core
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/38—Layered products comprising a layer of synthetic resin comprising epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G59/20—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
- C08G59/3227—Compounds containing acyclic nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G59/504—Amines containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G59/56—Amines together with other curing agents
-
- 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
- C08J3/00—Processes of treating or compounding macromolecular substances
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- C08J3/203—Solid polymers with solid and/or liquid additives
-
- 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
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/0405—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres
- C08J5/042—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres with carbon fibres
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- 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
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
- C08J5/243—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using carbon fibres
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- 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
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
-
- 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
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
-
- 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
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
- C08J2363/02—Polyglycidyl ethers of bis-phenols
Abstract
Description
式中、Yは1〜4個の炭素原子を含むアルキル基であり、Xは水素、ハロゲンまたは1〜4個の炭素原子を含むアルキル基であり、ならびに、RおよびR’は、アルキル基またはアルキルチオ基、好ましくは1〜4個の炭素原子を含むアルキル基またはアルキルチオ基である。特に好ましい実施形態において、Xは水素であり、Yはアルキル基、最も好ましくはメチル基であり、RおよびR’は両方ともアルキルチオ基、最も好ましくはメチルチオ基またはアルキル基、最も好ましくはエチル基である。
式中、R1、R2、R3、R4、R1 ’、R2 ’、R3 ’およびR4 ’は、以下から独立に選択される:水素;C1〜C6アルコキシ、好ましくはC1〜C4アルコキシ(ここで、アルコキシ基は直鎖もしくは分枝であってよく、例えばメトキシ、エトキシおよびイソプロポキシであってよい);C1〜C6アルキル、好ましくはC1〜C4アルキル(ここで、アルキル基は直鎖もしくは分枝であってよく、任意選択で置換されていてもよく、例えばメチル、エチル、イソプロピルおよびトリフルオロメチルであってよい);または、ハロゲン、たとえば塩素;
ここで、R1、R2、R3、R4、R1 ’、R2 ’、R3 ’およびR4 ’の少なくとも1つは、C1〜C6アルキル基である。
樹脂トランスファー成形法によって成形品群を製造し、ここで、24層の乾燥した一方向炭素繊維布(UD194 IMA/V800E/ZD0/500MM、Hexcel Corporationから入手可能)を準等方性レイアップ[+45/0/−45/90]3sにより金型の中にレイアップし、様々な樹脂組成物を注入した。これらの樹脂組成物は、Araldite MY721(N,N,N’,N’テトラグリシジル−4,4’−メチレンビスベンズアミン)として市販されている官能性エポキシ樹脂と、Araldite MY721のエポキシ含量に化学量論量の硬化性アミン基を提供する様々な量の硬化剤とを含んでいた。樹脂組成物を110℃で金型に注入し、毎分2℃ずつ温度を上げて金型を180℃に加熱し、次いで金型を180℃で2時間保持することにより硬化させた。
例1の手順を繰り返したが、MDEAとMCDEAの混合物を、4,4’メチレン(メチルエチルアニリン)−(クロロジエチルアニリン)(M−MEACDEA)に置き換えて、表3に示す割合で使用した。
39.19重量%のHuntsman Advanced Materials Limited(UK)からAraldite MY9655として市販されている多官能エポキシ樹脂N,N,N’,N’テトラグリシジル−4,4’メチレンビスベンズアミン、21.09重量%のHuntsman Advanced Materials Limited(UK)からAraldite MY722として市販されている多機能エポキシ樹脂N,N,N’,N’−テトラグリシジル−3,3’−ジエチル−4,4’−メチレンビスベンズアミン、36.72重量%の硬化剤系、および3重量%のArkemaからXT100として市販されているアクリルコアシェル強化粒子の混合物を含む樹脂組成物を調製した。硬化剤系は、7.35重量%(組成物全体の重量に対して)のAlbermarleからEthacure 300として入手可能なジメチルチオトルエンジアミン異性体混合物の形態のアルキルベンゼンジアミン、および、29.37重量%%(組成物全体の重量に対して)の4,4’メチレン(メチルエチルアニリン)−(クロロジエチルアニリン)(M−MEACDEA)の形態の追加の芳香族アミンを含んでいた。アルキルベンジルジアミンは硬化剤系の20重量%を構成し、追加の芳香族アミンは硬化剤系の80重量%を構成した。
38重量%のHuntsman Advanced Materials Limited(UK)からAraldite MY721として市販されている官能性エポキシ樹脂Ν,Ν,Ν’,Ν’テトラグリシジル−4,4’メチレンビスベンズアミン、21重量%のHuntsman Advanced Materials Limited(UK)からAraldite MY722として市販されている多機能エポキシ樹脂Ν,Ν,Ν’,Ν’−テトラグリシジル−3,3’−ジエチル−4,4’−メチレンビスベンズアミン、38重量%の硬化剤系、および3重量%のArkemaからXT100として市販されているアクリルコアシェル強化粒子の混合物を含む樹脂組成物を調製した。硬化剤系は、4重量%(組成物全体の重量に対して)のAlbermarleからEthacure 100として入手可能なジエチルトルエンジアミン異性体混合物の形態のアルキルベンゼンジアミン、および、24重量%(組成物全体の重量に対して)の4,4’メチレン(メチルエチルアニリン)−(クロロジエチルアニリン)(M−MEACDEA)の形態の追加の芳香族アミンを含んでいた。アルキルベンジルジアミンは硬化剤系の10.5重量%を構成し、追加の芳香族アミンは硬化剤系の89.5重量%を構成した。
Claims (25)
- アルキルベンゼンジアミンおよび追加の芳香族アミンを含むエポキシ樹脂の硬化剤系。
- アルキルベンゼンジアミンが、1種以上の追加のアルキル基および/またはチオアルキル基を有するトルエンジアミンである、請求項1に記載の硬化剤系。
- アルキルベンゼンジアミンが以下の式で示されるものである、請求項2に記載の硬化剤系:
式中、Yは1〜4個の炭素原子を含むアルキル基であり、Xは水素または1〜4個の炭素原子を含むアルキル基であり、ならびに、RおよびR’は、アルキル基またはアルキルチオ基、好ましくは1〜4個の炭素原子を含むアルキル基またはアルキルチオ基である。 - 式Iの化合物が以下の構造を有する、請求項3に記載の硬化剤系。
- 式IIの化合物が以下の構造を有する、請求項3または請求項4に記載の硬化剤系。
- アルキルベンゼンジアミンが、式Iおよび式IIの化合物の混合物を含み、好ましくは式Iの化合物と式IIの化合物との比が90:10から70:30であり、より好ましくは80:20である、請求項3〜5のいずれか1項に記載の硬化剤系。
- アルキルベンゼンジアミンが、好ましくは90%:10%〜70%:30%の比で、より好ましくは80%:20%の比で、以下の化合物の混合物を含む、請求項6に記載の硬化剤系。
- 追加の芳香族アミンがアルキレン架橋芳香族アミンである、請求項1〜7のいずれか1項に記載の硬化剤系。
- 追加の芳香族アミンがメチレンビスアニリン、好ましくは4,4’メチレンビスアニリンである、請求項8に記載の硬化剤系。
- メチレンビスアニリンが以下の式を有する、請求項9に記載の硬化剤系:
式中、R1、R2、R3、R4、R1 ’、R2 ’、R3 ’およびR4 ’は、以下から独立に選択される:水素;C1〜C6アルコキシ、好ましくはC1〜C4アルコキシ(ここで、アルコキシ基は直鎖もしくは分枝であり、例えばメトキシ、エトキシおよびイソプロポキシであってよい);C1〜C6アルキル、好ましくはC1〜C4アルキル(ここで、アルキル基は直鎖もしくは分枝であってよく、任意選択で置換されていてもよく、例えばメチル、エチル、イソプロピルおよびトリフルオロメチルであってよい);または、ハロゲン、たとえば塩素;
ここで、R1、R2、R3、R4、R1 ’、R2 ’、R3 ’およびR4 ’の少なくとも1つは、C1〜C6アルキル基である。 - 追加の芳香族アミンが2種以上のメチレンビスアニリンの混合物を含む、請求項9または請求項10に記載の硬化剤系。
- 追加の芳香族アミンが、メチレンビス(ジエチルアニリン)(M−DEA)、メチレンビス(クロロジエチルアニリン)(M−CDEA)、メチレン(メチルエチルアニリン)−(クロロジエチルアニリン)(M−MEACDEA)またはそれらの混合物を含む、請求項9〜11のいずれか1項に記載の硬化剤系。
- 硬化剤系の5〜50重量%、好ましくは10〜50重量%、より好ましくは20〜40重量%のアルキルベンジルジアミンを含む、請求項1〜12のいずれか1項に記載の硬化剤系。
- アルキルベンゼンジアミンと追加の芳香族アミンとの混合物が22℃で液体である、請求項1〜13のいずれか1項に記載の硬化剤系。
- 繊維強化複合体を製造するための注入プロセスにおける、エポキシ樹脂の硬化剤として芳香族アミンの性能を向上させるためのアルキルベンゼンジアミンの使用。
- アルキルベンゼンジアミンが請求項2〜7のいずれか1項で規定されるアルキルベンゼンジアミンであり、および/または芳香族アミンが請求項8〜12のいずれか1項で規定される追加の芳香族アミンである、請求項15に記載の使用。
- エポキシ樹脂と請求項1〜14のいずれか1項に記載の硬化剤系との混合物を含む硬化性エポキシ樹脂組成物。
- エポキシ樹脂が少なくとも2の官能性を有する、請求項17に記載の硬化性エポキシ樹脂組成物。
- 硬化剤系によって提供されるアミン基とエポキシ樹脂によって提供されるエポキシ基との相対量が、0.7:1.3以上であり、好ましくは0.8:1.2以上である、請求項17または請求項18に記載の硬化性エポキシ樹脂組成物。
- 120℃で10〜100cP、および60℃で100〜1000cPの粘度を有する、請求項17〜19のいずれか1項に記載の硬化性エポキシ樹脂組成物。
- 繊維強化複合体の製造における硬化性樹脂としての請求項17から20のいずれか1項に記載の組成物の使用。
- 注入プロセスによる繊維強化複合体の製造における請求項17から20のいずれか1項に記載の組成物の使用。
- 繊維強化材料と、請求項17から20のいずれか1項に記載の硬化性エポキシ樹脂組成物を硬化させることにより得られる硬化エポキシ樹脂とを含む繊維強化複合体。
- 繊維強化複合体の製造プロセスであって、繊維強化材料がレイアップされ、請求項17から20のいずれか1項に記載の硬化性エポキシ樹脂組成物が、80〜130℃の温度で繊維強化材料の全体に注入され、そして、組成物が繊維強化材料に注入される際その温度が150〜190℃に上げられる、上記プロセス。
- 繊維強化材料が、ガラス、炭素、グラファイト、ホウ素、セラミックまたはアラミド繊維から選択される、請求項24に記載のプロセス。
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