CA1243040A - Epoxy resin fortifiers based on aromatic amides - Google Patents
Epoxy resin fortifiers based on aromatic amidesInfo
- Publication number
- CA1243040A CA1243040A CA000409315A CA409315A CA1243040A CA 1243040 A CA1243040 A CA 1243040A CA 000409315 A CA000409315 A CA 000409315A CA 409315 A CA409315 A CA 409315A CA 1243040 A CA1243040 A CA 1243040A
- Authority
- CA
- Canada
- Prior art keywords
- fortifier
- resin
- epoxide
- curing agent
- epoxy resin
- 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.)
- Expired
Links
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 45
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 27
- 150000008430 aromatic amides Chemical class 0.000 title claims abstract description 14
- 238000001723 curing Methods 0.000 claims abstract description 41
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 35
- 239000000203 mixture Substances 0.000 claims abstract description 24
- 150000001412 amines Chemical class 0.000 claims abstract description 18
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 11
- 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 9
- 150000001408 amides Chemical class 0.000 claims abstract description 5
- 238000013007 heat curing Methods 0.000 claims abstract description 3
- 238000013329 compounding Methods 0.000 claims abstract 2
- 229920005989 resin Polymers 0.000 claims description 22
- 239000011347 resin Substances 0.000 claims description 22
- 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 11
- 125000000217 alkyl group Chemical group 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 9
- 239000003054 catalyst Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 150000002825 nitriles Chemical class 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 230000008569 process Effects 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- IYNGLSRZLOHZJA-UHFFFAOYSA-N 1,4,7-triazabicyclo[5.2.2]undecane Chemical compound C1CN2CCN1CCNCC2 IYNGLSRZLOHZJA-UHFFFAOYSA-N 0.000 claims description 2
- YBAZINRZQSAIAY-UHFFFAOYSA-N 4-aminobenzonitrile Chemical compound NC1=CC=C(C#N)C=C1 YBAZINRZQSAIAY-UHFFFAOYSA-N 0.000 claims description 2
- RIAHASMJDOMQER-UHFFFAOYSA-N 5-ethyl-2-methyl-1h-imidazole Chemical compound CCC1=CN=C(C)N1 RIAHASMJDOMQER-UHFFFAOYSA-N 0.000 claims description 2
- 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
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 claims description 2
- 150000008378 aryl ethers Chemical group 0.000 claims description 2
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000002924 oxiranes Chemical class 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 3
- FUIQBJHUESBZNU-UHFFFAOYSA-N 2-[(dimethylazaniumyl)methyl]phenolate Chemical compound CN(C)CC1=CC=CC=C1O FUIQBJHUESBZNU-UHFFFAOYSA-N 0.000 claims 1
- BVURNMLGDQYNAF-UHFFFAOYSA-N dimethyl(1-phenylethyl)amine Chemical compound CN(C)C(C)C1=CC=CC=C1 BVURNMLGDQYNAF-UHFFFAOYSA-N 0.000 claims 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 claims 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 claims 1
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract description 6
- 125000003277 amino group Chemical group 0.000 abstract description 4
- -1 aliphatic primary amine Chemical class 0.000 description 13
- 239000004593 Epoxy Substances 0.000 description 8
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 7
- 150000002118 epoxides Chemical class 0.000 description 7
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 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 5
- 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 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 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
- 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
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 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
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 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
- 239000004848 polyfunctional curative Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 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
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- PLFFHJWXOGYWPR-HEDMGYOXSA-N (4r)-4-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-3-yl]pentan-1-ol Chemical compound C([C@]1(C)[C@H]2CC[C@H]34)CCC(C)(C)[C@@H]1CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@@H]1[C@@H](CCCO)C PLFFHJWXOGYWPR-HEDMGYOXSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-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
- BPIWYCGXATZHQC-UHFFFAOYSA-N 1-[4-(oxiran-2-ylmethoxy)phenyl]-6-oxabicyclo[3.1.0]hexane Chemical compound C=1C=C(C23C(CCC2)O3)C=CC=1OCC1CO1 BPIWYCGXATZHQC-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
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-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
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- XRCRJFOGPCJKPF-UHFFFAOYSA-N 2-butylbenzene-1,4-diol Chemical compound CCCCC1=CC(O)=CC=C1O XRCRJFOGPCJKPF-UHFFFAOYSA-N 0.000 description 1
- CKZJQEQANLYJAG-UHFFFAOYSA-N 2-phenyl-2-[(2-phenyloxiran-2-yl)methoxymethyl]oxirane Chemical compound C1OC1(C=1C=CC=CC=1)COCC1(C=2C=CC=CC=2)CO1 CKZJQEQANLYJAG-UHFFFAOYSA-N 0.000 description 1
- AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 description 1
- HDGMAACKJSBLMW-UHFFFAOYSA-N 4-amino-2-methylphenol Chemical compound CC1=CC(N)=CC=C1O HDGMAACKJSBLMW-UHFFFAOYSA-N 0.000 description 1
- GGUOCFNAWIODMF-UHFFFAOYSA-N 4-chloroacetanilide Chemical compound CC(=O)NC1=CC=C(Cl)C=C1 GGUOCFNAWIODMF-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
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- ADAHGVUHKDNLEB-UHFFFAOYSA-N Bis(2,3-epoxycyclopentyl)ether Chemical compound C1CC2OC2C1OC1CCC2OC21 ADAHGVUHKDNLEB-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 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
- 229930195725 Mannitol Natural products 0.000 description 1
- 241001274660 Modulus Species 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- OORDEDRRTSWSRC-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] acetate Chemical compound CC(=O)OCC(CO)(CO)CO OORDEDRRTSWSRC-UHFFFAOYSA-N 0.000 description 1
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical class OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229960002380 dibutyl phthalate Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- HLMZZYYGOKOOTA-UHFFFAOYSA-N n-(2,5-dichlorophenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC(Cl)=CC=C1Cl HLMZZYYGOKOOTA-UHFFFAOYSA-N 0.000 description 1
- CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 1
- MSLICLMCQYQNPK-UHFFFAOYSA-N n-(4-bromophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(Br)C=C1 MSLICLMCQYQNPK-UHFFFAOYSA-N 0.000 description 1
- 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
- 229920003986 novolac Polymers 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical class CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920002647 polyamide 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
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical class NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent 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)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000409315A CA1243040A (en) | 1982-08-12 | 1982-08-12 | Epoxy resin fortifiers based on aromatic amides |
| US06/516,575 US4480082A (en) | 1982-08-12 | 1983-07-25 | Epoxy resin fortifiers based on aromatic amides |
| IL69366A IL69366A (en) | 1982-08-12 | 1983-07-28 | Epoxy resin fortifiers based on the reaction product of aromatic amides with mono-or diepoxides and their preparation |
| EP83304543A EP0103968B1 (en) | 1982-08-12 | 1983-08-05 | Fortifier for epoxy resins, method for the preparation thereof and fortified epoxy resin compositions containing same |
| DE8383304543T DE3372624D1 (en) | 1982-08-12 | 1983-08-05 | Fortifier for epoxy resins, method for the preparation thereof and fortified epoxy resin compositions containing same |
| JP58147934A 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 |
| KR1019830003789A KR900008530B1 (ko) | 1982-08-12 | 1983-08-12 | 방향족 아미드기재로된, 에폭시 수지에 대한 강화제와 이의 제조방법 |
| BR8304359A BR8304359A (pt) | 1982-08-12 | 1983-08-12 | Fortificadores de resina de epoxi com base em amidas aromaticas |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000409315A CA1243040A (en) | 1982-08-12 | 1982-08-12 | Epoxy resin fortifiers based on aromatic amides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1243040A true CA1243040A (en) | 1988-10-11 |
Family
ID=4123392
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000409315A Expired CA1243040A (en) | 1982-08-12 | 1982-08-12 | Epoxy resin fortifiers based on aromatic amides |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4480082A (Direct) |
| EP (1) | EP0103968B1 (Direct) |
| JP (1) | JPS5949223A (Direct) |
| KR (1) | KR900008530B1 (Direct) |
| BR (1) | BR8304359A (Direct) |
| CA (1) | CA1243040A (Direct) |
| DE (1) | DE3372624D1 (Direct) |
| IL (1) | IL69366A (Direct) |
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 |
| DE3587776T2 (de) * | 1984-08-07 | 1994-07-21 | Mitsubishi Rayon Co | Zwischenprodukt für Verbundstoffe. |
| 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 |
| 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 |
| TWI250934B (en) | 1997-10-17 | 2006-03-11 | Advancsd Plastics Technologies | Barrier-coated polyester articles and the fabrication method thereof |
| 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 |
| US6808820B2 (en) | 2000-09-05 | 2004-10-26 | Advanced Plastics Technology Ltd. | Multilayer containers and preforms having barrier properties utilizing recycled material |
| AU2001275473A1 (en) | 2000-06-23 | 2002-01-08 | The Dow Global Technologies Inc. | Epoxy resing and process for making the same |
| WO2002048234A2 (en) | 2000-12-14 | 2002-06-20 | Dow Global Technologies Inc. | Epoxy resins and process for making the same |
| BR0316103A (pt) | 2002-11-08 | 2005-09-27 | Advanced Plastics Technologies | Molde de injeção tendo uma porção resistente a desgaste e uma porção de alto coeficiente de transferência térmica, e um processo para formação de pré-forma |
| MXPA05006365A (es) * | 2002-12-13 | 2005-08-29 | Monsanto Technology Llc | Microcapsulas con velocidad de liberacion ajustada con aminas. |
| US7608672B2 (en) * | 2004-02-12 | 2009-10-27 | Illinois Tool Works Inc. | Infiltrant system for rapid prototyping process |
| CA2562074C (en) | 2004-04-16 | 2014-12-16 | Advanced Plastics Technologies Luxembourg S.A. | A bottle, a method of forming the bottle, a liquid dispensing system and an extruded profile |
| US7303387B2 (en) | 2004-06-10 | 2007-12-04 | Advanced Plastics Technologies Luxembourg S.A. | System for controlling mold temperatures |
| US20050277549A1 (en) * | 2004-06-14 | 2005-12-15 | Monsanto Technology Llc | Microcapsules having activated release of core material therein |
| WO2007027606A1 (en) | 2005-08-30 | 2007-03-08 | Advanced Plastics Technologies Luxembourg S.A. | Methods and systems for controlling mold temperatures |
| SG175605A1 (en) | 2006-11-30 | 2011-11-28 | Texas A & M Univ Sys | Intercalation agent free compositions useful to make nanocomposite polymers |
| EP2235087B1 (en) | 2008-01-23 | 2014-10-01 | Dow Global Technologies LLC | Epoxy resin hardener compositions and epoxy resin compositions containing such hardener compositions |
| 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 |
| EP2356158B1 (en) * | 2008-12-12 | 2018-12-26 | Dow Global Technologies LLC | Coating composition, a process of producing a coating composition, a coated article, and a method of forming such articles |
| KR101710216B1 (ko) | 2008-12-16 | 2017-02-24 | 다우 글로벌 테크놀로지스 엘엘씨 | 안료를 불투명화시키는 중합체 캡슐화된 금속 산화물을 포함하는 코팅 조성물 및 그의 제조 방법 |
| AU2010213530B2 (en) * | 2009-02-13 | 2015-09-03 | Monsanto Technology Llc | Encapsulation of herbicides to reduce crop injury |
| BRPI1006198B1 (pt) | 2009-03-16 | 2020-02-18 | Dow Global Technologies Llc | Processo para produzir uma dispersão e dispersão |
| EP2473541A1 (en) | 2009-03-30 | 2012-07-11 | Dow Global Technologies LLC | Hybrid dispersions and methods for producing the same |
| KR101716916B1 (ko) | 2009-07-24 | 2017-03-15 | 다우 글로벌 테크놀로지스 엘엘씨 | 코팅된 용기 장치, 그의 제조 방법 |
| WO2011011707A2 (en) | 2009-07-24 | 2011-01-27 | Dow Global Technologies Inc. | Coated container device, method of making the same |
| WO2011053904A1 (en) * | 2009-10-30 | 2011-05-05 | Dow Global Technologies Inc. | Alkyd dispersion, and a process for producing the same |
| AU2011291580B2 (en) | 2010-08-18 | 2015-08-20 | 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 |
| MX2016000046A (es) | 2013-07-11 | 2016-03-09 | Dow Global Technologies Llc | Proceso para producir uretano-isocianuratos. |
| 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 |
| WO2015113015A1 (en) | 2014-01-27 | 2015-07-30 | Monsanto Technology Llc | Aqueous herbicidal concentrates |
| US10851213B2 (en) | 2014-06-27 | 2020-12-01 | Dow Global Technologies Llc | Method for optimizing a hegman rating of a diluted emulsion, a diluted emulsion produced thereby, and a coating made |
| KR102071909B1 (ko) * | 2016-11-29 | 2020-01-31 | 주식회사 엘지화학 | 중합성 조성물 |
| BR112019025526B1 (pt) | 2017-06-13 | 2023-10-03 | Monsanto Technology Llc | Microcápsula herbicida, seu processo de preparação, composição herbicida aquosa, e métodos para controlar ervas daninhas |
| 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 |
| US11419331B2 (en) | 2019-01-30 | 2022-08-23 | Monsanto Technology Llc | Microencapsulated acetamide herbicides |
| EP4192898A4 (en) | 2020-08-05 | 2024-02-21 | Blue Cube IP LLC | NEW 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 JP JP58147934A patent/JPS5949223A/ja active Granted
- 1983-08-12 BR BR8304359A patent/BR8304359A/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR840005828A (ko) | 1984-11-19 |
| US4480082A (en) | 1984-10-30 |
| IL69366A0 (en) | 1983-11-30 |
| EP0103968B1 (en) | 1987-07-22 |
| BR8304359A (pt) | 1984-03-20 |
| KR900008530B1 (ko) | 1990-11-24 |
| IL69366A (en) | 1987-02-27 |
| JPS6244769B2 (Direct) | 1987-09-22 |
| EP0103968A1 (en) | 1984-03-28 |
| JPS5949223A (ja) | 1984-03-21 |
| DE3372624D1 (en) | 1987-08-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |