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 |
| BR8304359A BR8304359A (pt) | 1982-08-12 | 1983-08-12 | Fortificadores de resina de epoxi com base em amidas aromaticas |
| KR1019830003789A KR900008530B1 (ko) | 1982-08-12 | 1983-08-12 | 방향족 아미드기재로된, 에폭시 수지에 대한 강화제와 이의 제조방법 |
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 (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 |
| DE3587776T2 (de) * | 1984-08-07 | 1994-07-21 | Mitsubishi Rayon Co | Zwischenprodukt für Verbundstoffe. |
| USRE33965E (en) * | 1984-08-07 | 1992-06-16 | Mitsubishi Rayon Co., Ltd. | Intermediate for composite materials |
| 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 |
| US5262509A (en) * | 1990-08-03 | 1993-11-16 | The Dow Chemical Company | Mesogenic glycidyl amines |
| 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 |
| 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 |
| TWI250934B (en) | 1997-10-17 | 2006-03-11 | Advancsd Plastics Technologies | Barrier-coated polyester articles and the fabrication method thereof |
| 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 |
| CA2412909A1 (en) | 2000-06-23 | 2002-01-03 | Stephen M. Hoyles | Epoxy resins and process for making the same |
| AU8891601A (en) | 2000-09-05 | 2002-03-22 | Advanced Plastics Technologies | Multilayer containers and preforms having barrier properties utilizing recycled material |
| WO2002048234A2 (en) | 2000-12-14 | 2002-06-20 | Dow Global Technologies Inc. | Epoxy resins and process for making the same |
| MXPA05004888A (es) | 2002-11-08 | 2005-08-18 | Advanced Plastics Technologies | Molde de inyeccion que tiene una porcion resistente al desgaste y una porcion de alta transferencia termica y un metodo para formar una preforma. |
| AU2003297683A1 (en) * | 2002-12-13 | 2004-07-09 | 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 |
| AU2005235596A1 (en) | 2004-04-16 | 2005-11-03 | Advanced Plastics Technologies Luxembourg S.A. | Preforms, bottles and methods of manufacturing the preforms and the bottles |
| BRPI0511664A (pt) | 2004-06-10 | 2008-01-02 | Advanced Plastics Technologies | métodos e sistemas para o controle de temperaturas de moldes |
| EP1755384A1 (en) * | 2004-06-14 | 2007-02-28 | Monsanto Technology, LLC | Microcapsules having activated release of core material therein |
| US7717697B2 (en) | 2005-08-30 | 2010-05-18 | Sharon Hutchinson | Methods and systems for controlling mold temperatures |
| JP2010511740A (ja) | 2006-11-30 | 2010-04-15 | ザ テキサス エー アンド エム ユニバーシティ システム | ナノコンポジットポリマーの製造に有用な挿入剤非含有組成物 |
| JP5603256B2 (ja) | 2008-01-23 | 2014-10-08 | ダウ グローバル テクノロジーズ エルエルシー | エポキシ樹脂硬化剤組成物及び前記硬化剤組成物を含むエポキシ樹脂組成物 |
| US7879925B2 (en) * | 2008-05-27 | 2011-02-01 | Zephyros, Inc. | Composite with natural fibers |
| EP2291435B1 (en) * | 2008-06-03 | 2016-08-17 | Dow Global Technologies LLC | A composite dispersion, method of producing the same, and articles made therefrom |
| US9221940B2 (en) * | 2008-12-12 | 2015-12-29 | Dow Global Technologies Llc | Coating composition, a process of producing a coating composition, a coated article, and a method of forming such articles |
| EP2358823B1 (en) | 2008-12-16 | 2018-09-19 | Dow Global Technologies LLC | A process of producing a coating composition comprising polymer encapsulated metal oxide opacifying pigments |
| WO2010093970A2 (en) | 2009-02-13 | 2010-08-19 | Monsanto Technology Llc | Encapsulation of herbicides to reduce crop injury |
| US20110319521A1 (en) | 2009-03-16 | 2011-12-29 | Lundgard Richard A | Dispersion, and a process for producing the same |
| CN102421815A (zh) | 2009-03-30 | 2012-04-18 | 陶氏环球技术有限责任公司 | 混合分散体及其生产方法 |
| KR101719843B1 (ko) * | 2009-07-24 | 2017-03-24 | 다우 글로벌 테크놀로지스 엘엘씨 | 코팅된 용기 장치, 그의 제조 방법 |
| BR112012000451B1 (pt) | 2009-07-24 | 2019-09-03 | Dow Global Technologies Llc | dispositivo recipiente revestido e método para fazer um dispositivo recipiente revestido |
| US9200177B2 (en) * | 2009-10-30 | 2015-12-01 | Dow Global Technologies Llc | Alkyd dispersion, and a process for producing the same |
| AR082855A1 (es) | 2010-08-18 | 2013-01-16 | Monsanto Technology Llc | Aplicacion temprana de acetamidas encapsuladas para reducir daños en los cultivos |
| 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 |
| EP3019544B1 (en) | 2013-07-11 | 2019-11-06 | 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 |
| WO2015113015A1 (en) | 2014-01-27 | 2015-07-30 | Monsanto Technology Llc | Aqueous herbicidal concentrates |
| CN106661349B (zh) | 2014-06-27 | 2019-05-28 | 陶氏环球技术有限责任公司 | 用于优化稀释乳液的Hegman等级的方法、通过该方法产生的稀释乳液以及由该稀释乳液制成的涂料 |
| KR102071909B1 (ko) * | 2016-11-29 | 2020-01-31 | 주식회사 엘지화학 | 중합성 조성물 |
| EP3638023A4 (en) | 2017-06-13 | 2021-04-14 | Monsanto Technology LLC | MICRO ENCAPSULATED HERBICIDES |
| CN112867640B (zh) | 2018-10-17 | 2024-03-29 | 陶氏环球技术有限责任公司 | 涂料组合物、经涂布织物、制造经涂布织物的方法以及由经涂布织物制成的制品 |
| US11419331B2 (en) | 2019-01-30 | 2022-08-23 | Monsanto Technology Llc | Microencapsulated acetamide herbicides |
| WO2022031517A1 (en) | 2020-08-05 | 2022-02-10 | Blue Cube Ip Llc | Novel 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 JP JP58147934A patent/JPS5949223A/ja active Granted
- 1983-08-12 BR BR8304359A patent/BR8304359A/pt not_active IP Right Cessation
- 1983-08-12 KR KR1019830003789A patent/KR900008530B1/ko not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6244769B2 (enExample) | 1987-09-22 |
| US4480082A (en) | 1984-10-30 |
| EP0103968A1 (en) | 1984-03-28 |
| BR8304359A (pt) | 1984-03-20 |
| IL69366A0 (en) | 1983-11-30 |
| EP0103968B1 (en) | 1987-07-22 |
| KR900008530B1 (ko) | 1990-11-24 |
| JPS5949223A (ja) | 1984-03-21 |
| IL69366A (en) | 1987-02-27 |
| DE3372624D1 (en) | 1987-08-27 |
| KR840005828A (ko) | 1984-11-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |