CA1276358C - Epoxy resin for preparing electric laminates - Google Patents
Epoxy resin for preparing electric laminatesInfo
- Publication number
- CA1276358C CA1276358C CA000473035A CA473035A CA1276358C CA 1276358 C CA1276358 C CA 1276358C CA 000473035 A CA000473035 A CA 000473035A CA 473035 A CA473035 A CA 473035A CA 1276358 C CA1276358 C CA 1276358C
- Authority
- CA
- Canada
- Prior art keywords
- epoxy resin
- curing agent
- resin composition
- phenol
- composition according
- 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 - Fee Related
Links
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 124
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 124
- 239000000203 mixture Substances 0.000 claims abstract description 102
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 64
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 52
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 29
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- -1 phenol compound Chemical class 0.000 claims abstract description 14
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 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 claims description 28
- 239000002966 varnish Substances 0.000 claims description 27
- 229920005989 resin Polymers 0.000 claims description 20
- 239000011347 resin Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 16
- 239000004593 Epoxy Substances 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 13
- 239000004215 Carbon black (E152) Substances 0.000 claims description 12
- 229930195733 hydrocarbon Natural products 0.000 claims description 12
- YGCOKJWKWLYHTG-UHFFFAOYSA-N [[4,6-bis[bis(hydroxymethyl)amino]-1,3,5-triazin-2-yl]-(hydroxymethyl)amino]methanol Chemical compound OCN(CO)C1=NC(N(CO)CO)=NC(N(CO)CO)=N1 YGCOKJWKWLYHTG-UHFFFAOYSA-N 0.000 claims description 10
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 claims description 9
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 230000003014 reinforcing effect Effects 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 8
- 150000002576 ketones Chemical class 0.000 claims description 7
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical group CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 claims description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 125000003700 epoxy group Chemical group 0.000 claims description 5
- 150000002148 esters Chemical group 0.000 claims description 5
- 150000002460 imidazoles Chemical class 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical group COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000010030 laminating Methods 0.000 claims description 4
- 229920000877 Melamine resin Polymers 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 239000004020 conductor Substances 0.000 claims description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 150000002430 hydrocarbons Chemical group 0.000 claims description 3
- 229920003986 novolac Polymers 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 239000001294 propane Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims 1
- 239000007983 Tris buffer Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical compound NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 239000007787 solid Substances 0.000 description 15
- 239000003085 diluting agent Substances 0.000 description 12
- 239000011521 glass Substances 0.000 description 12
- 239000000306 component Substances 0.000 description 11
- 230000009477 glass transition Effects 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 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 description 9
- 238000002156 mixing Methods 0.000 description 9
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 8
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- 210000001217 buttock Anatomy 0.000 description 8
- 150000002989 phenols Chemical class 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 239000004744 fabric Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 238000005553 drilling Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011342 resin composition Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 5
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 239000011889 copper foil Substances 0.000 description 4
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 2
- 241000518994 Conta Species 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000001145 hydrido group Chemical group *[H] 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 230000036647 reaction Effects 0.000 description 2
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 2
- 229910000679 solder Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- CSXHKOSAWQTJBT-YDYKLMMDSA-N (2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoic acid;hydrate Chemical compound O.O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C(O)=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C.O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C(O)=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C CSXHKOSAWQTJBT-YDYKLMMDSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- LYWVNPSVLAFTFX-UHFFFAOYSA-N 4-methylbenzenesulfonate;morpholin-4-ium Chemical compound C1COCCN1.CC1=CC=C(S(O)(=O)=O)C=C1 LYWVNPSVLAFTFX-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- 241000531908 Aramides Species 0.000 description 1
- 229930182670 Astin Natural products 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 244000187656 Eucalyptus cornuta Species 0.000 description 1
- 241000820057 Ithone Species 0.000 description 1
- 241001325354 Lamiinae Species 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- 241000252794 Sphinx Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 108010057108 condensin complexes Proteins 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- VEVRNHHLCPGNDU-MUGJNUQGSA-O desmosine Chemical compound OC(=O)[C@@H](N)CCCC[N+]1=CC(CC[C@H](N)C(O)=O)=C(CCC[C@H](N)C(O)=O)C(CC[C@H](N)C(O)=O)=C1 VEVRNHHLCPGNDU-MUGJNUQGSA-O 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000002305 electric material Substances 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229960004279 formaldehyde Drugs 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 125000005474 octanoate group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
- C08G14/06—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols and monomers containing hydrogen attached to nitrogen
- C08G14/10—Melamines
-
- 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
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
- C08G59/623—Aminophenols
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/40—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes epoxy resins
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/032—Organic insulating material consisting of one material
- H05K1/0326—Organic insulating material consisting of one material containing O
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
- H05K1/0366—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement reinforced, e.g. by fibres, fabrics
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K2201/00—Indexing scheme relating to printed circuits covered by H05K1/00
- H05K2201/03—Conductive materials
- H05K2201/0332—Structure of the conductor
- H05K2201/0335—Layered conductors or foils
- H05K2201/0355—Metal foils
Landscapes
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Epoxy Resins (AREA)
- Laminated Bodies (AREA)
- Reinforced Plastic Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
- Manufacturing Of Electric Cables (AREA)
- Processing Of Terminals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3403172 | 1984-01-31 | ||
| DE3403172.3 | 1984-01-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1276358C true CA1276358C (en) | 1990-11-13 |
Family
ID=6226300
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000473035A Expired - Fee Related CA1276358C (en) | 1984-01-31 | 1985-01-29 | Epoxy resin for preparing electric laminates |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4661568A (https=) |
| EP (2) | EP0169865A1 (https=) |
| JP (1) | JPS61501154A (https=) |
| KR (2) | KR920002615B1 (https=) |
| AT (1) | ATE35817T1 (https=) |
| AU (1) | AU557131B2 (https=) |
| BR (1) | BR8505172A (https=) |
| CA (1) | CA1276358C (https=) |
| DE (1) | DE3563852D1 (https=) |
| DK (1) | DK440085D0 (https=) |
| ES (1) | ES8608020A1 (https=) |
| FI (1) | FI853743A0 (https=) |
| IE (1) | IE57890B1 (https=) |
| IL (1) | IL74199A (https=) |
| IN (1) | IN164123B (https=) |
| NO (1) | NO161266C (https=) |
| SG (1) | SG87488G (https=) |
| WO (1) | WO1985003515A1 (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8519290D0 (en) * | 1985-07-31 | 1985-09-04 | Dow Chemical Rheinwerk Gmbh | Resin composition |
| IL80277A0 (en) * | 1985-10-15 | 1987-01-30 | President Eng Corp | Process for the production of prepregs and metal-laminated base material for circuit boards,and apparatus for carrying out this process |
| US4808652A (en) * | 1988-06-08 | 1989-02-28 | Monsanto Company | Crosslinker compositions comprising amino resins, epoxies and styrene allyl alcohol copolymers |
| US5210157A (en) * | 1989-08-15 | 1993-05-11 | Akzo N.V. | Interpenetrating network of ring-containing allyl polymers and epoxy resin, and a laminate prepared therefrom |
| EP0507271A3 (en) * | 1991-04-03 | 1993-04-21 | The Dow Chemical Company | Epoxy resin compositions for use in electrical laminates |
| US5364925A (en) * | 1992-01-27 | 1994-11-15 | The Dow Chemical Company | Epoxy resin advanced with a dihydric phenol and further chain extended with an additional dihydric phenol for use in electrical laminates |
| CA2199390A1 (en) * | 1994-09-08 | 1996-03-14 | Jan Andre Jozef Schutyser | Allyl-containing epoxy resin composition comprising a copolymer of an ethylenically unsaturated anhydride and a vinyl compound |
| WO1996028490A1 (en) * | 1995-03-14 | 1996-09-19 | Nissan Chemical Industries, Ltd. | Heat-resistant epoxy resin composition |
| EP0935628B1 (en) | 1996-10-29 | 2001-12-05 | Isola Laminate Systems Corporation | Copolymer of styrene and maleic anhydride comprising an epoxy resin composition and a co-cross-linking agent |
| JPH11279376A (ja) * | 1998-03-27 | 1999-10-12 | Hitachi Chem Co Ltd | 印刷配線板用エポキシ樹脂組成物およびこれを用いた印刷配線板 |
| US6855738B2 (en) | 2003-06-06 | 2005-02-15 | Dow Global Technologies Inc. | Nanoporous laminates |
| WO2012043245A1 (ja) * | 2010-09-29 | 2012-04-05 | 日本カーバイド工業株式会社 | メラミンエポキシ樹脂モノマーおよび樹脂組成物 |
| JP2016502470A (ja) | 2012-10-12 | 2016-01-28 | ハイ ボルテイジ グラフィックス インコーポレイテッドＨｉｇｈ Ｖｏｌｔａｇｅ Ｇｒａｐｈｉｃｓ，Ｉｎｃ． | 熱融着可能な可撓性の装飾品およびそれを製造する方法 |
| US8911858B2 (en) | 2012-10-31 | 2014-12-16 | Empire Technology Development Llc | Multifunctional melamine epoxy resins, methylols and amines |
| US9890130B2 (en) | 2013-02-15 | 2018-02-13 | Empire Technology Development Llc | Phenolic epoxy compounds |
| US9868683B2 (en) | 2013-06-13 | 2018-01-16 | Empire Technology Development Llc | Multi-functional phenolic resins |
| EP3077364A4 (en) | 2013-12-02 | 2017-11-08 | Empire Technology Development LLC | Novel gemini surfactants and their use |
| US9526185B2 (en) * | 2014-04-08 | 2016-12-20 | Finisar Corporation | Hybrid PCB with multi-unreinforced laminate |
| AU2016223748B2 (en) | 2015-02-27 | 2020-07-09 | Huntsman Advanced Materials Licensing (Switzerland) Gmbh | A process for manufacturing a fiber reinforced composite article, the composite article obtained and the use thereof |
| US12304161B2 (en) * | 2021-02-16 | 2025-05-20 | Vestas Wind Systems A/S | Manufacture of a wind turbine component |
| US20230374337A1 (en) * | 2022-05-20 | 2023-11-23 | Epoxy Technology, Inc. | High performance conformal coatings |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB622675A (en) * | 1946-10-02 | 1949-05-05 | Donald Atherton | Manufacture of new synthetic resinous condensation products |
| US3502557A (en) * | 1965-04-01 | 1970-03-24 | Ppg Industries Inc | Electrodeposition of amine-aldehyde condensate and hydroxy-containing carboxylic acid coreaction products |
| US4499268A (en) * | 1982-02-23 | 1985-02-12 | Ciba Geigy Corporation | Process for the preparation of isomelamines |
| US4467070A (en) * | 1982-09-30 | 1984-08-21 | Ford Motor Company | Thermosetting coating composition comprising polymeric catalyst - III |
| US4393181A (en) * | 1982-06-30 | 1983-07-12 | Shell Oil Company | Polyfunctional phenolic-melamine epoxy resin curing agents |
-
1985
- 1985-01-29 CA CA000473035A patent/CA1276358C/en not_active Expired - Fee Related
- 1985-01-30 IE IE224/85A patent/IE57890B1/en not_active IP Right Cessation
- 1985-01-30 DE DE8585100914T patent/DE3563852D1/de not_active Expired
- 1985-01-30 JP JP60500642A patent/JPS61501154A/ja active Granted
- 1985-01-30 AU AU39342/85A patent/AU557131B2/en not_active Ceased
- 1985-01-30 KR KR1019850700238A patent/KR920002615B1/ko not_active Expired
- 1985-01-30 US US06/776,558 patent/US4661568A/en not_active Expired - Fee Related
- 1985-01-30 EP EP85900668A patent/EP0169865A1/en active Pending
- 1985-01-30 IL IL74199A patent/IL74199A/xx unknown
- 1985-01-30 WO PCT/EP1985/000026 patent/WO1985003515A1/en not_active Ceased
- 1985-01-30 ES ES539962A patent/ES8608020A1/es not_active Expired
- 1985-01-30 FI FI853743A patent/FI853743A0/fi not_active Application Discontinuation
- 1985-01-30 EP EP85100914A patent/EP0155469B1/en not_active Expired
- 1985-01-30 BR BR8505172A patent/BR8505172A/pt not_active IP Right Cessation
- 1985-01-30 AT AT85100914T patent/ATE35817T1/de not_active IP Right Cessation
- 1985-01-31 IN IN87/MAS/85A patent/IN164123B/en unknown
- 1985-09-27 NO NO85853822A patent/NO161266C/no unknown
- 1985-09-27 DK DK440085A patent/DK440085D0/da not_active Application Discontinuation
- 1985-09-28 KR KR1019850700238A patent/KR850700252A/ko active Granted
-
1988
- 1988-12-14 SG SG874/88A patent/SG87488G/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR8505172A (pt) | 1986-01-21 |
| KR920002615B1 (ko) | 1992-03-30 |
| KR850700252A (ko) | 1985-12-26 |
| IN164123B (https=) | 1989-01-14 |
| ATE35817T1 (de) | 1988-08-15 |
| ES539962A0 (es) | 1986-04-16 |
| IE850224L (en) | 1985-07-31 |
| DE3563852D1 (en) | 1988-08-25 |
| IL74199A0 (en) | 1985-04-30 |
| FI853743L (fi) | 1985-09-27 |
| NO161266B (no) | 1989-04-17 |
| EP0155469A1 (en) | 1985-09-25 |
| EP0169865A1 (en) | 1986-02-05 |
| US4661568A (en) | 1987-04-28 |
| SG87488G (en) | 1989-06-16 |
| DK440085A (da) | 1985-09-27 |
| FI853743A7 (fi) | 1985-09-27 |
| IE57890B1 (en) | 1993-05-05 |
| AU557131B2 (en) | 1986-12-04 |
| DK440085D0 (da) | 1985-09-27 |
| FI853743A0 (fi) | 1985-09-27 |
| AU3934285A (en) | 1985-08-27 |
| EP0155469B1 (en) | 1988-07-20 |
| WO1985003515A1 (en) | 1985-08-15 |
| ES8608020A1 (es) | 1986-04-16 |
| JPS61501154A (ja) | 1986-06-12 |
| JPH0369364B2 (https=) | 1991-10-31 |
| IL74199A (en) | 1988-07-31 |
| NO853822L (no) | 1985-09-27 |
| NO161266C (no) | 1989-07-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |