JPS61500024A - 枝分かれノボラックのポリグリシジルエ−テル - Google Patents
枝分かれノボラックのポリグリシジルエ−テルInfo
- Publication number
- JPS61500024A JPS61500024A JP59503647A JP50364784A JPS61500024A JP S61500024 A JPS61500024 A JP S61500024A JP 59503647 A JP59503647 A JP 59503647A JP 50364784 A JP50364784 A JP 50364784A JP S61500024 A JPS61500024 A JP S61500024A
- Authority
- JP
- Japan
- Prior art keywords
- phenol
- methylol
- group
- epoxy
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920003986 novolac Polymers 0.000 title claims description 80
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims description 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 78
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 72
- 238000006243 chemical reaction Methods 0.000 claims description 45
- -1 alknyl Chemical group 0.000 claims description 33
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 26
- 239000004593 Epoxy Substances 0.000 claims description 24
- 150000002989 phenols Chemical class 0.000 claims description 21
- 235000013824 polyphenols Nutrition 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims description 3
- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 3
- 125000005024 alkenyl aryl group Chemical group 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 230000001588 bifunctional effect Effects 0.000 claims description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 38
- 238000000034 method Methods 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- 229930185605 Bisphenol Natural products 0.000 description 18
- 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 18
- 150000002118 epoxides Chemical class 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 241000238557 Decapoda Species 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 229960004279 formaldehyde Drugs 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 11
- 235000019256 formaldehyde Nutrition 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 230000009257 reactivity Effects 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 229930003836 cresol Natural products 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000006735 epoxidation reaction Methods 0.000 description 5
- 239000003822 epoxy resin Substances 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000007033 dehydrochlorination reaction Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- KDFWZNJXMYHVMF-UHFFFAOYSA-N 2,3,5,6-tetrakis(hydroxymethyl)benzene-1,4-diol Chemical compound OCC1=C(O)C(CO)=C(CO)C(O)=C1CO KDFWZNJXMYHVMF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-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
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-UHFFFAOYSA-N 0.000 description 2
- 229920013683 Celanese Polymers 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 150000001896 cresols Chemical class 0.000 description 2
- NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 150000003944 halohydrins Chemical class 0.000 description 2
- 230000020169 heat generation Effects 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 230000002452 interceptive effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 1
- LSYXXLMBRSSBGS-UHFFFAOYSA-N 2,4,6-tris(hydroxymethyl)phenol Chemical compound OCC1=CC(CO)=C(O)C(CO)=C1 LSYXXLMBRSSBGS-UHFFFAOYSA-N 0.000 description 1
- HRWYHCYGVIJOEC-UHFFFAOYSA-N 2-(octoxymethyl)oxirane Chemical compound CCCCCCCCOCC1CO1 HRWYHCYGVIJOEC-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- HJSPWKGEPDZNLK-UHFFFAOYSA-N 4-benzylphenol Chemical class C1=CC(O)=CC=C1CC1=CC=CC=C1 HJSPWKGEPDZNLK-UHFFFAOYSA-N 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- 241000473391 Archosargus rhomboidalis Species 0.000 description 1
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical class [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 244000089486 Phragmites australis subsp australis Species 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 241000384512 Trachichthyidae Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000006664 bond formation reaction Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- QKTIZUURRAGCHU-UHFFFAOYSA-N chloromethylbenzene;n,n-dimethylmethanamine Chemical compound CN(C)C.ClCC1=CC=CC=C1 QKTIZUURRAGCHU-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 206010016531 fetishism Diseases 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 150000003739 xylenols Chemical class 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
-
- 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
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
- C08G59/08—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols from phenol-aldehyde condensates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3218—Carbocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US538033 | 1983-09-30 | ||
| US06/538,033 US4474929A (en) | 1983-09-30 | 1983-09-30 | Polyglycidyl ethers of branched novolacs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61500024A true JPS61500024A (ja) | 1986-01-09 |
| JPS6244007B2 JPS6244007B2 (OSRAM) | 1987-09-17 |
Family
ID=24145151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59503647A Granted JPS61500024A (ja) | 1983-09-30 | 1984-09-20 | 枝分かれノボラックのポリグリシジルエ−テル |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4474929A (OSRAM) |
| EP (1) | EP0157854B1 (OSRAM) |
| JP (1) | JPS61500024A (OSRAM) |
| AU (1) | AU578632B2 (OSRAM) |
| CA (1) | CA1218496A (OSRAM) |
| DE (1) | DE3479666D1 (OSRAM) |
| WO (1) | WO1985001505A1 (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2023521068A (ja) * | 2020-04-24 | 2023-05-23 | エルジー・ケム・リミテッド | 硬化剤、これを含む半導体接着用組成物、半導体接着用フィルムおよびこれを用いた半導体パッケージ |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59184250A (ja) * | 1983-04-04 | 1984-10-19 | Sumitomo Chem Co Ltd | 電子部品封止または積層用樹脂組成物 |
| US4599268A (en) * | 1984-04-16 | 1986-07-08 | International Business Machines Corporation | Product containing an epoxy composition |
| US4550128A (en) * | 1984-04-16 | 1985-10-29 | International Business Machines Corporation | Epoxy composition |
| US4597996A (en) * | 1984-04-16 | 1986-07-01 | International Business Machines Corporation | Process of laminating with an epoxy composition |
| US4939229A (en) * | 1989-05-12 | 1990-07-03 | Rohm And Haas Company | Method for preparing lithographically sensitive branched novolaks using a mannich base intermediate |
| US5264500A (en) * | 1991-07-30 | 1993-11-23 | Allied-Signal Inc. | APT resins |
| US5349111A (en) * | 1993-04-23 | 1994-09-20 | The Dow Chemical Company | Benzocyclobutene novolac resin compositions |
| US5427857A (en) * | 1994-06-28 | 1995-06-27 | E. I. Du Pont De Nemours And Company | Cathodic electrocoating compositions containing branched epoxy amine resins |
| US5472998A (en) * | 1994-09-16 | 1995-12-05 | E. I. Du Pont De Nemours And Company | Polymeric additive for cathodic electrocoating compositions for improved throw power |
| US5942563A (en) * | 1997-07-18 | 1999-08-24 | The Glidden Company | Aqueous dispersed acrylic-epoxy, branched epoxy protective coatings |
| US6716568B1 (en) * | 2000-09-15 | 2004-04-06 | Microchem Corp. | Epoxy photoresist composition with improved cracking resistance |
| US7273638B2 (en) * | 2003-01-07 | 2007-09-25 | International Business Machines Corp. | High density plasma oxidation |
| US9469777B2 (en) * | 2012-08-21 | 2016-10-18 | Nissan Chemical Industries, Ltd. | Resist underlayer film forming composition that contains novolac resin having polynuclear phenol |
| JP6537061B2 (ja) * | 2014-10-28 | 2019-07-03 | 日東電工株式会社 | 光導波路用感光性樹脂組成物および光導波路コア層形成用光硬化性フィルム、ならびにそれを用いた光導波路、光・電気伝送用混載フレキシブルプリント配線板 |
| US20250109241A1 (en) * | 2023-10-03 | 2025-04-03 | Westlake Epoxy Inc. | Epoxy resin compositions and methods of producing thereof |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL196344A (OSRAM) * | 1954-04-09 | |||
| FR1307292A (fr) * | 1960-04-29 | 1962-10-26 | Union Carbide Corp | Procédé de préparation de résines à base notamment de formaldéhyde |
| US3212958A (en) * | 1961-09-01 | 1965-10-19 | Union Carbide Corp | Polyglycidyl ethers of hydroxybenzylated 4, 4'-dihydroxydiphenyl sulfones and laminates containing same |
| US3285938A (en) * | 1961-10-10 | 1966-11-15 | Union Carbide Corp | Tetraglycidyl ethers of tris (hydroxy-benzyl) phenol |
| NL6413222A (OSRAM) * | 1963-11-12 | 1965-05-13 | ||
| US4394496A (en) * | 1971-08-19 | 1983-07-19 | The Dow Chemical Company | Epoxidation products of 1,1,1-tri-(hydroxyphenyl) alkanes |
| JPS5828372B2 (ja) * | 1975-10-21 | 1983-06-15 | 群栄化学工業株式会社 | フエノ−ルケイジユシセンイ モシクハ フイルムノセイゾウホウ |
| IT1051397B (it) * | 1975-12-19 | 1981-04-21 | S I R S P A | Procedimento per la preparazione di resine novolacche epossidate |
| US4102866A (en) * | 1976-10-29 | 1978-07-25 | Texaco Development Corporation | Method of making glycidyl ethers of novolak resins |
| US4256844A (en) * | 1976-12-23 | 1981-03-17 | The Dow Chemical Company | Fire retardant, thermosetting, resinous reaction products of phosphoric acid and methyol- or alkoxymethyl-substituted epoxides |
| DE3069534D1 (en) * | 1979-12-27 | 1984-11-29 | Mitsui Petrochemical Ind | Novolak resin composition and products formed therefrom |
| JPS56116717A (en) * | 1980-02-20 | 1981-09-12 | Yuka Shell Epoxy Kk | Preparation of novolak-type epoxy resin |
| JPS57141419A (en) * | 1981-02-27 | 1982-09-01 | Mitsubishi Petrochem Co Ltd | Production of polyepoxide |
| US4440914A (en) * | 1981-10-19 | 1984-04-03 | Ciba-Geigy Corporation | Solid epoxy resin systems |
| JPS5936123A (ja) * | 1982-08-20 | 1984-02-28 | Sumitomo Chem Co Ltd | 新規なノボラツク型置換フエノ−ル樹脂のグリシジルエ−テル、その製造法およびこれを主成分とする封止剤 |
| US4468507A (en) * | 1983-11-21 | 1984-08-28 | The Dow Chemical Company | Method of limiting rate of heat evolution during acid-catalyzed phenol/polymethylolphenol condensations |
-
1983
- 1983-09-30 US US06/538,033 patent/US4474929A/en not_active Expired - Lifetime
-
1984
- 1984-09-20 EP EP84903689A patent/EP0157854B1/en not_active Expired
- 1984-09-20 JP JP59503647A patent/JPS61500024A/ja active Granted
- 1984-09-20 DE DE8484903689T patent/DE3479666D1/de not_active Expired
- 1984-09-20 AU AU35020/84A patent/AU578632B2/en not_active Ceased
- 1984-09-20 WO PCT/US1984/001495 patent/WO1985001505A1/en not_active Ceased
- 1984-09-25 CA CA000463954A patent/CA1218496A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2023521068A (ja) * | 2020-04-24 | 2023-05-23 | エルジー・ケム・リミテッド | 硬化剤、これを含む半導体接着用組成物、半導体接着用フィルムおよびこれを用いた半導体パッケージ |
Also Published As
| Publication number | Publication date |
|---|---|
| AU3502084A (en) | 1985-04-23 |
| US4474929A (en) | 1984-10-02 |
| EP0157854A4 (en) | 1986-03-04 |
| EP0157854A1 (en) | 1985-10-16 |
| AU578632B2 (en) | 1988-11-03 |
| CA1218496A (en) | 1987-02-24 |
| DE3479666D1 (en) | 1989-10-12 |
| EP0157854B1 (en) | 1989-09-06 |
| JPS6244007B2 (OSRAM) | 1987-09-17 |
| WO1985001505A1 (en) | 1985-04-11 |
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