JPS5949223A - エポキシ樹脂用強化剤及びその製造方法 - Google Patents
エポキシ樹脂用強化剤及びその製造方法Info
- Publication number
- JPS5949223A JPS5949223A JP58147934A JP14793483A JPS5949223A JP S5949223 A JPS5949223 A JP S5949223A JP 58147934 A JP58147934 A JP 58147934A JP 14793483 A JP14793483 A JP 14793483A JP S5949223 A JPS5949223 A JP S5949223A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- agent
- reinforcing agent
- resin composition
- toughening
- 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
Links
- 229920000647 polyepoxide Polymers 0.000 title claims description 50
- 239000003822 epoxy resin Substances 0.000 title claims description 35
- 239000003795 chemical substances by application Substances 0.000 title claims description 32
- 239000000203 mixture Substances 0.000 title claims description 27
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 230000002708 enhancing effect Effects 0.000 title 1
- 239000012745 toughening agent Substances 0.000 claims description 40
- 239000012744 reinforcing agent Substances 0.000 claims description 20
- 150000001412 amines Chemical class 0.000 claims description 19
- 229920005989 resin Polymers 0.000 claims description 19
- 239000011347 resin Substances 0.000 claims description 19
- 150000008430 aromatic amides Chemical class 0.000 claims description 11
- 239000000376 reactant Substances 0.000 claims description 11
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical group C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 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 description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000002825 nitriles Chemical class 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 claims description 6
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical group C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 150000001408 amides Chemical group 0.000 claims description 4
- RIAHASMJDOMQER-UHFFFAOYSA-N 5-ethyl-2-methyl-1h-imidazole Chemical compound CCC1=CN=C(C)N1 RIAHASMJDOMQER-UHFFFAOYSA-N 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims description 2
- 150000008378 aryl ethers Chemical group 0.000 claims description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 2
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 claims description 2
- 229920006391 phthalonitrile polymer Polymers 0.000 claims description 2
- 150000002924 oxiranes Chemical class 0.000 claims 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- JXPDNDHCMMOJPC-UHFFFAOYSA-N 2-hydroxybutanedinitrile Chemical compound N#CC(O)CC#N JXPDNDHCMMOJPC-UHFFFAOYSA-N 0.000 claims 1
- 150000001345 alkine derivatives Chemical class 0.000 claims 1
- 238000010276 construction Methods 0.000 claims 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 claims 1
- 230000001747 exhibiting effect Effects 0.000 claims 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 claims 1
- 238000001723 curing Methods 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 16
- 230000002787 reinforcement Effects 0.000 description 9
- 241000238557 Decapoda Species 0.000 description 8
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- -1 cycloaliphatic Chemical group 0.000 description 7
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 6
- 150000002118 epoxides Chemical class 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000004848 polyfunctional curative Substances 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 150000003931 anilides Chemical class 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 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 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 150000003944 halohydrins Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 238000005728 strengthening Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- ADVGKWPZRIDURE-UHFFFAOYSA-N 2'-Hydroxyacetanilide Chemical compound CC(=O)NC1=CC=CC=C1O ADVGKWPZRIDURE-UHFFFAOYSA-N 0.000 description 2
- GGMPTLAAIUQMIE-UHFFFAOYSA-N 2,3,4,5,6-pentachlorobiphenyl Chemical group ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=CC=CC=C1 GGMPTLAAIUQMIE-UHFFFAOYSA-N 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical group NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 235000010356 sorbitol Nutrition 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- IYNGLSRZLOHZJA-UHFFFAOYSA-N 1,4,7-triazabicyclo[5.2.2]undecane Chemical compound C1CN2CCN1CCNCC2 IYNGLSRZLOHZJA-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- RXQVGXQHXIUBPX-UHFFFAOYSA-N 2,6-dimethyl-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound CC1=CC=CC(C)=C1N(CC1OC1)CC1OC1 RXQVGXQHXIUBPX-UHFFFAOYSA-N 0.000 description 1
- FUIQBJHUESBZNU-UHFFFAOYSA-N 2-[(dimethylazaniumyl)methyl]phenolate Chemical compound CN(C)CC1=CC=CC=C1O FUIQBJHUESBZNU-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
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- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
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- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
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- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- NIGRIMOLDFBQPY-UHFFFAOYSA-N n-[4-[(4-formamidophenyl)methyl]phenyl]formamide Chemical compound C1=CC(NC=O)=CC=C1CC1=CC=C(NC=O)C=C1 NIGRIMOLDFBQPY-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C08G59/182—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 using pre-adducts of epoxy compounds with curing agents
-
- 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
-
- 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
- C08G59/44—Amides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000409315A CA1243040A (en) | 1982-08-12 | 1982-08-12 | Epoxy resin fortifiers based on aromatic amides |
| CA409315 | 1982-08-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5949223A true JPS5949223A (ja) | 1984-03-21 |
| JPS6244769B2 JPS6244769B2 (enExample) | 1987-09-22 |
Family
ID=4123392
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58147934A Granted JPS5949223A (ja) | 1982-08-12 | 1983-08-12 | エポキシ樹脂用強化剤及びその製造方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4480082A (enExample) |
| EP (1) | EP0103968B1 (enExample) |
| JP (1) | JPS5949223A (enExample) |
| KR (1) | KR900008530B1 (enExample) |
| BR (1) | BR8304359A (enExample) |
| CA (1) | CA1243040A (enExample) |
| DE (1) | DE3372624D1 (enExample) |
| IL (1) | IL69366A (enExample) |
Families Citing this family (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5599629A (en) * | 1984-03-01 | 1997-02-04 | Amoco Corporation | High modulus prepregable epoxy resin systems |
| USRE33965E (en) * | 1984-08-07 | 1992-06-16 | Mitsubishi Rayon Co., Ltd. | Intermediate for composite materials |
| KR930003019B1 (ko) * | 1984-08-07 | 1993-04-16 | 미쯔비시 레이욘 가부시끼가이샤 | 복합재료용 중간체 |
| JPS6375044A (ja) * | 1986-09-17 | 1988-04-05 | Toto Ltd | 連続気孔多孔体の製造方法 |
| US4956411A (en) * | 1988-02-05 | 1990-09-11 | Mitsubishi Rayon Company, Ltd. | Epoxy resin composition for composite material from m- or o-substituted triglycidylaminophenols, diaminodiphenylsulfone and latent curing agents |
| US5003039A (en) * | 1988-11-18 | 1991-03-26 | The United States Of America As Represented By The Secretary Of The Navy | Amino phenyl containing curing agent for high performance phthalonitrile resin |
| JP2736443B2 (ja) * | 1989-06-22 | 1998-04-02 | 三菱レイヨン株式会社 | 複合材料用エポキシ樹脂組成物 |
| CA2024189A1 (en) * | 1989-10-23 | 1991-04-24 | Kam W. Ho | Bismaleimide resin compositions |
| JPH066621B2 (ja) * | 1990-04-16 | 1994-01-26 | 富士化成工業株式会社 | 一成分系加熱硬化性エポキシド組成物 |
| US5043411A (en) * | 1990-05-14 | 1991-08-27 | Nova Petrochemicals Inc. | Cyanate ester resin composition containing an epoxy/aromatic adduct |
| JPH0480226A (ja) * | 1990-07-23 | 1992-03-13 | Mitsubishi Rayon Co Ltd | 複合材料用エポキシ樹脂組成物 |
| DE4024466C2 (de) * | 1990-07-30 | 1995-04-20 | Dainippon Ink & Chemicals | Thermisch härtbare Mischungen aus polyfunktionellen Formamiden und aromatischen Mono-, Di- oder Polyglycidylethern und deren Verwendung |
| US5360884A (en) * | 1990-08-03 | 1994-11-01 | The Dow Chemical Company | Mesogenic glycidyl amine blends |
| US5362822A (en) * | 1990-08-03 | 1994-11-08 | The Dow Chemical Company | Mesogenic adducts |
| US5262509A (en) * | 1990-08-03 | 1993-11-16 | The Dow Chemical Company | Mesogenic glycidyl amines |
| GB2259916A (en) * | 1991-09-27 | 1993-03-31 | Coates Brothers Plc | Solder-resist, heat-curable compositions |
| US5357008A (en) * | 1992-01-22 | 1994-10-18 | W. R. Grace & Co.-Conn. | Latent curing agent for epoxy resin and its preparation |
| US5298575A (en) * | 1992-11-30 | 1994-03-29 | The Dow Chemical Company | Nitro group terminated mesogenic epoxy resin adducts |
| US6011111A (en) * | 1993-10-18 | 2000-01-04 | The Dow Chemical Company | Hydroxy-phenoxyether polymer thermoplastic composites |
| US5503936A (en) * | 1994-02-28 | 1996-04-02 | Ciba-Geigy Corporation | N-alkyl-N'-aryl-P-phenylenediamines as modifiers for epoxy resins |
| TWI250934B (en) | 1997-10-17 | 2006-03-11 | Advancsd Plastics Technologies | Barrier-coated polyester articles and the fabrication method thereof |
| US6352426B1 (en) | 1998-03-19 | 2002-03-05 | Advanced Plastics Technologies, Ltd. | Mold for injection molding multilayer preforms |
| US6312641B1 (en) | 1997-10-17 | 2001-11-06 | Plastic Fabrication Technologies Llc | Method of making containers and preforms incorporating barrier materials |
| US5962621A (en) * | 1998-04-28 | 1999-10-05 | The Dow Chemical Company | Process for preparing hydroxy-functionalized polyesters |
| US6109006A (en) * | 1998-07-14 | 2000-08-29 | Advanced Plastics Technologies, Ltd. | Process for making extruded pet containers |
| BR0112294A (pt) | 2000-06-23 | 2003-06-24 | Dow Global Technologies Inc | Resinas epóxi e processo para fabricá-las |
| EP1315608A1 (en) | 2000-09-05 | 2003-06-04 | Advanced Plastics Technologies, Ltd | Multilayer containers and preforms having barrier properties utilizing recycled material |
| AU2002226010A1 (en) | 2000-12-14 | 2002-06-24 | Dow Global Technologies Inc. | Epoxy resins and process for making the same |
| AU2003285192A1 (en) | 2002-11-08 | 2004-06-03 | Advanced Plastics Technologies Ltd | Injection mold having a wear resistant portion and a high heat transfer portion and a method for forming a preform |
| WO2004054362A1 (en) * | 2002-12-13 | 2004-07-01 | Monsanto Technology Llc | Microcapsules with amine adjusted release rates |
| US7608672B2 (en) * | 2004-02-12 | 2009-10-27 | Illinois Tool Works Inc. | Infiltrant system for rapid prototyping process |
| MXPA06011806A (es) | 2004-04-16 | 2006-12-15 | Advanced Plastics Technologies | Articulos de mono y multiples capas y metodos de extrusion para producir los mismos. |
| CA2569639A1 (en) | 2004-06-10 | 2005-12-29 | Advanced Plastics Technologies Luxembourg S.A. | Methods and systems for cooling molds |
| BRPI0512102A (pt) * | 2004-06-14 | 2008-02-06 | Monsanto Technology Llc | microcápsulas tendo liberação ativada de material de núcleo dentro delas |
| MX2008002479A (es) | 2005-08-30 | 2008-04-07 | Advanced Plastics Technologies | Metodos y sistemas por controlar temperaturas de molde. |
| CN101595169B (zh) | 2006-11-30 | 2012-11-21 | 德克萨斯A&M大学系统 | 可用于制备纳米复合聚合物的不含插层剂的组合物 |
| CN105255312A (zh) * | 2008-01-23 | 2016-01-20 | 蓝立方知识产权公司 | 环氧树脂硬化剂组合物及含有这样的硬化剂组合物的环氧树脂组合物 |
| US7879925B2 (en) * | 2008-05-27 | 2011-02-01 | Zephyros, Inc. | Composite with natural fibers |
| US8349945B2 (en) * | 2008-06-03 | 2013-01-08 | Dow Global Technologies Llc | Composite dispersion, method of producing the same, and articles made therefrom |
| JP5883649B2 (ja) * | 2008-12-12 | 2016-03-15 | ダウ グローバル テクノロジーズ エルエルシー | コーティング組成物、コーティング組成物を製造する工程、コートされた物品、およびそのような物品を形成する方法 |
| US8829083B2 (en) | 2008-12-16 | 2014-09-09 | Dow Global Technologies Llc | Coating composition, a process of producing a coating composition, a coated article, and a method of making such articles |
| ES2645703T3 (es) * | 2009-02-13 | 2017-12-07 | Monsanto Technology Llc | Encapsulación de herbicidas para reducir daños en los cultivos |
| JP5689455B2 (ja) | 2009-03-16 | 2015-03-25 | ダウ グローバル テクノロジーズ エルエルシー | 分散体及び分散体を製造するための方法 |
| KR20120000571A (ko) | 2009-03-30 | 2012-01-02 | 다우 글로벌 테크놀로지스 엘엘씨 | 하이브리드 분산액 및 그의 제조 방법 |
| CN107413607B (zh) | 2009-07-24 | 2021-02-12 | 陶氏环球技术有限责任公司 | 制备涂布的容器装置或涂布的闭合装置的方法 |
| CN102686489B (zh) | 2009-07-24 | 2015-11-25 | 陶氏环球技术有限责任公司 | 涂布的容器装置、其制备方法 |
| EP2493955A1 (en) * | 2009-10-30 | 2012-09-05 | Dow Global Technologies LLC | Alkyd dispersion, and a process for producing the same |
| US9913469B2 (en) | 2010-08-18 | 2018-03-13 | Monsanto Technology Llc | Early applications of encapsulated acetamides for reduced injury in crops |
| WO2012138348A1 (en) | 2011-04-08 | 2012-10-11 | Dow Global Technologies Llc | A coating compositon, and a process for producing the same |
| TWI621639B (zh) | 2013-01-07 | 2018-04-21 | 東麗股份有限公司 | 環氧樹脂組成物及預浸漬物 |
| WO2015006391A1 (en) | 2013-07-11 | 2015-01-15 | Dow Global Technologies Llc | Process for making urethane-isocyanurates |
| US20150197682A1 (en) | 2014-01-16 | 2015-07-16 | Clearwater International, Llc | Anti-gel agent for polyhydroxyetheramines, gel stabilized polyhydroxyetheramine solutions, and methods for making and using same |
| AR099195A1 (es) | 2014-01-27 | 2016-07-06 | Monsanto Technology Llc | Concentrados herbicidas acuosos |
| WO2015199980A2 (en) | 2014-06-27 | 2015-12-30 | Dow Global Technologies Llc | A method for optimizing a hegman rating of a diluted emulsion, a diluted emulsion produced thereby, and a coating made therefrom |
| KR102071909B1 (ko) * | 2016-11-29 | 2020-01-31 | 주식회사 엘지화학 | 중합성 조성물 |
| CA3066746A1 (en) | 2017-06-13 | 2018-12-20 | Monsanto Technology Llc | Microencapsulated herbicides |
| JP7419357B2 (ja) | 2018-10-17 | 2024-01-22 | ダウ グローバル テクノロジーズ エルエルシー | コーティング組成物、コーティングされた布、コーティングされた布を作製する方法、およびコーティングされた布から作製された物品 |
| EP3917319A4 (en) | 2019-01-30 | 2022-11-23 | Monsanto Technology LLC | MICRO-ENCAPSULATED ACETAMIDE HERBICIDES |
| US12391792B2 (en) | 2020-08-05 | 2025-08-19 | Blue Cube Ip Llc | Hardener formulation for cold curing epoxy systems |
| CN117263624B (zh) * | 2023-11-22 | 2024-02-06 | 长沙中科盛联新材料有限公司 | 一种再生骨料混凝土及其制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2870170A (en) * | 1953-12-08 | 1959-01-20 | Shell Dev | Esters of epoxy-substituted polycarboxylic acids and epoxy-substituted alcohols |
| US3403199A (en) * | 1966-03-08 | 1968-09-24 | Ramos Thomas | Diglycidyl ether of polyhydric alcohols with diamines or hydroquinones and bis(2, 3-epoxycyclopentyl)ether |
| US3759914A (en) * | 1971-08-10 | 1973-09-18 | Du Pont | Improved curing compositions for epoxy resins comprising latent amine curing agent and accelerator |
| CH589116A5 (en) * | 1974-10-25 | 1977-06-30 | Asahi Chemical Ind | Non-toxic hardeners for epoxy resins - consisting of amide derivs. of aminomethyl-1,8-diamino-octane |
| US4182832A (en) * | 1976-12-10 | 1980-01-08 | Ciba-Geigy Corporation | Curable composition containing 1,4-diaminobutane derivatives |
| US4197389A (en) * | 1977-07-18 | 1980-04-08 | Hoechst Aktiengesellschaft | Hardening agent for aqueous epoxy resin compositions |
| US4195152A (en) * | 1977-08-01 | 1980-03-25 | Henkel Corporation | N-Alkyl polyamines and curing of epoxy resins therewith |
| US4182831A (en) * | 1977-12-07 | 1980-01-08 | Celanese Polymer Specialties Company | Cationic epoxide resinous composition |
-
1982
- 1982-08-12 CA CA000409315A patent/CA1243040A/en not_active Expired
-
1983
- 1983-07-25 US US06/516,575 patent/US4480082A/en not_active Expired - Fee Related
- 1983-07-28 IL IL69366A patent/IL69366A/xx unknown
- 1983-08-05 EP EP83304543A patent/EP0103968B1/en not_active Expired
- 1983-08-05 DE DE8383304543T patent/DE3372624D1/de not_active Expired
- 1983-08-12 KR KR1019830003789A patent/KR900008530B1/ko not_active Expired
- 1983-08-12 BR BR8304359A patent/BR8304359A/pt not_active IP Right Cessation
- 1983-08-12 JP JP58147934A patent/JPS5949223A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IL69366A0 (en) | 1983-11-30 |
| US4480082A (en) | 1984-10-30 |
| EP0103968A1 (en) | 1984-03-28 |
| KR840005828A (ko) | 1984-11-19 |
| JPS6244769B2 (enExample) | 1987-09-22 |
| EP0103968B1 (en) | 1987-07-22 |
| CA1243040A (en) | 1988-10-11 |
| BR8304359A (pt) | 1984-03-20 |
| IL69366A (en) | 1987-02-27 |
| KR900008530B1 (ko) | 1990-11-24 |
| DE3372624D1 (en) | 1987-08-27 |
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