JPS60501663A - 枝分れノボラツク樹脂の製造方法 - Google Patents
枝分れノボラツク樹脂の製造方法Info
- Publication number
- JPS60501663A JPS60501663A JP59503499A JP50349984A JPS60501663A JP S60501663 A JPS60501663 A JP S60501663A JP 59503499 A JP59503499 A JP 59503499A JP 50349984 A JP50349984 A JP 50349984A JP S60501663 A JPS60501663 A JP S60501663A
- Authority
- JP
- Japan
- Prior art keywords
- phenol
- mixture
- reaction
- temperature
- methylol
- 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 58
- 238000004519 manufacturing process Methods 0.000 title claims description 24
- 229920005989 resin Polymers 0.000 title description 9
- 239000011347 resin Substances 0.000 title description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 81
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 53
- 238000006243 chemical reaction Methods 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 38
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 19
- 238000009833 condensation Methods 0.000 claims description 18
- 150000002989 phenols Chemical class 0.000 claims description 18
- 230000005494 condensation Effects 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 14
- -1 aralkenyl Chemical group 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 230000009257 reactivity Effects 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 238000012546 transfer Methods 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 2
- 230000001588 bifunctional effect Effects 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000012258 stirred mixture Substances 0.000 claims description 2
- 125000005024 alkenyl aryl group Chemical group 0.000 claims 1
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 claims 1
- 239000003426 co-catalyst Substances 0.000 claims 1
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 claims 1
- 230000014759 maintenance of location Effects 0.000 claims 1
- 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 19
- 239000004593 Epoxy Substances 0.000 description 17
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 14
- 229930185605 Bisphenol Natural products 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 235000013824 polyphenols Nutrition 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000006872 improvement Effects 0.000 description 6
- 238000006384 oligomerization reaction Methods 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
- 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 5
- 241000238557 Decapoda Species 0.000 description 5
- 229930003836 cresol Natural products 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 3
- 238000007033 dehydrochlorination reaction Methods 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000006735 epoxidation reaction Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 230000002452 interceptive effect Effects 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 1
- ZBSGNEYIENETRW-UHFFFAOYSA-N 2,3-bis(hydroxymethyl)phenol Chemical compound OCC1=CC=CC(O)=C1CO ZBSGNEYIENETRW-UHFFFAOYSA-N 0.000 description 1
- JBCUKQQIWSWEOK-UHFFFAOYSA-N 2-(benzenesulfonyl)aniline Chemical compound NC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1 JBCUKQQIWSWEOK-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- HJSPWKGEPDZNLK-UHFFFAOYSA-N 4-benzylphenol Chemical compound C1=CC(O)=CC=C1CC1=CC=CC=C1 HJSPWKGEPDZNLK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical group OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 235000004035 Cryptotaenia japonica Nutrition 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 101150025669 HDT2 gene Proteins 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
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 102000007641 Trefoil Factors Human genes 0.000 description 1
- 235000015724 Trifolium pratense Nutrition 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 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
- 238000009739 binding Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 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 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- XGZRAKBCYZIBKP-UHFFFAOYSA-L disodium;dihydroxide Chemical compound [OH-].[OH-].[Na+].[Na+] XGZRAKBCYZIBKP-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- GUOWRAWNQQJSEU-UHFFFAOYSA-M gold(1+);hydroxide Chemical compound [OH-].[Au+] GUOWRAWNQQJSEU-UHFFFAOYSA-M 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 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 1
- 230000020169 heat generation Effects 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 230000003993 interaction Effects 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
- 238000009533 lab test Methods 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 238000010667 large scale reaction Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- KZHAHJANVBGCOC-UHFFFAOYSA-N phenyl hypochlorite Chemical class ClOC1=CC=CC=C1 KZHAHJANVBGCOC-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000007781 pre-processing Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002510 pyrogen Substances 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000010512 small scale reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 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
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/553,718 US4468507A (en) | 1983-11-21 | 1983-11-21 | Method of limiting rate of heat evolution during acid-catalyzed phenol/polymethylolphenol condensations |
| US553718 | 1983-11-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60501663A true JPS60501663A (ja) | 1985-10-03 |
| JPS6241964B2 JPS6241964B2 (OSRAM) | 1987-09-05 |
Family
ID=24210459
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59503499A Granted JPS60501663A (ja) | 1983-11-21 | 1984-09-20 | 枝分れノボラツク樹脂の製造方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4468507A (OSRAM) |
| EP (1) | EP0147538B1 (OSRAM) |
| JP (1) | JPS60501663A (OSRAM) |
| AU (1) | AU560884B2 (OSRAM) |
| CA (1) | CA1218495A (OSRAM) |
| DE (1) | DE3466228D1 (OSRAM) |
| WO (1) | WO1985002193A1 (OSRAM) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4474929A (en) * | 1983-09-30 | 1984-10-02 | The Dow Chemical Company | Polyglycidyl ethers of branched novolacs |
| US5079314A (en) * | 1985-01-11 | 1992-01-07 | The Dow Chemical Company | Curable compositions containing epoxidized phenolformaldehyde resins containing reduced quantities of 2-functional components |
| US4939229A (en) * | 1989-05-12 | 1990-07-03 | Rohm And Haas Company | Method for preparing lithographically sensitive branched novolaks using a mannich base intermediate |
| DE4031575A1 (de) * | 1990-06-13 | 1991-12-19 | Hoechst Ag | Phenolharz, verfahren zu seiner herstellung und verwendung |
| US5349111A (en) * | 1993-04-23 | 1994-09-20 | The Dow Chemical Company | Benzocyclobutene novolac resin compositions |
| US6001950A (en) * | 1998-09-22 | 1999-12-14 | Borden Chemical, Inc. | Phenol-novolacs with improved optical properties |
| US9844528B2 (en) | 2006-08-24 | 2017-12-19 | University Of Tennessee Research Foundation | SARMs and method of use thereof |
| US20230374213A1 (en) * | 2020-10-05 | 2023-11-23 | Advanced Polymer Coatings, Inc. | Process for preparing branched phenolic novolak |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2385373A (en) * | 1942-08-12 | 1945-09-25 | Pennsylvania Coal Products Com | Method of producing a resin and product derived therefrom |
| US2609352A (en) * | 1951-05-22 | 1952-09-02 | Du Pont | Process for preparing monomeric stable methylolphenol compositions |
| US2859204A (en) * | 1955-03-01 | 1958-11-04 | Gen Electric | Methylolated compositions and products derived therefrom |
| US3062783A (en) * | 1957-10-02 | 1962-11-06 | Rayonier Inc | Reaction products of polymethylol phenol and sulfited tannins |
| GB973712A (en) * | 1959-12-21 | 1964-10-28 | Philips Electronic Associated | Improvements in or relating to resins of the novolak-type |
| AT259868B (de) * | 1965-04-29 | 1968-02-12 | Albert Ag Chem Werke | Verfahren zur Herstellung von Novolaken aus p,p'-Diphenylolpropan und Formaldehyd |
| BE792532A (fr) * | 1971-12-09 | 1973-06-08 | Texaco Ag | Procede de production continue de resines de |
| US4112160A (en) * | 1972-01-11 | 1978-09-05 | Sumitomo Durez Company, Ltd. | Solid adherend substrates bonded with rubber cement compositions |
| 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 |
| DE2650025A1 (de) * | 1976-10-30 | 1978-05-11 | Zimmer Ag | Verfahren zur herstellung von linearen phenol-formaldehyd-kondensaten |
| 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 |
| JPS57177011A (en) * | 1981-04-23 | 1982-10-30 | Kanebo Ltd | Granular or powdery phenol formaldehyde type resin and its preparation |
| US4461859A (en) * | 1981-11-16 | 1984-07-24 | Ppg Industries, Inc. | Method of preparing a phenolic aldehyde resin and resin composition for an adhesive system to be applied to glass fibers |
| US4433129A (en) * | 1982-01-19 | 1984-02-21 | Union Carbide Corporation | Hemi-formals of methylolated phenols |
| 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 |
-
1983
- 1983-11-21 US US06/553,718 patent/US4468507A/en not_active Expired - Fee Related
-
1984
- 1984-09-20 JP JP59503499A patent/JPS60501663A/ja active Granted
- 1984-09-20 AU AU34349/84A patent/AU560884B2/en not_active Ceased
- 1984-09-20 WO PCT/US1984/001496 patent/WO1985002193A1/en not_active Ceased
- 1984-09-25 CA CA000463953A patent/CA1218495A/en not_active Expired
- 1984-09-26 EP EP84111449A patent/EP0147538B1/en not_active Expired
- 1984-09-26 DE DE8484111449T patent/DE3466228D1/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0147538A1 (en) | 1985-07-10 |
| DE3466228D1 (en) | 1987-10-22 |
| CA1218495A (en) | 1987-02-24 |
| AU3434984A (en) | 1985-06-03 |
| JPS6241964B2 (OSRAM) | 1987-09-05 |
| WO1985002193A1 (en) | 1985-05-23 |
| EP0147538B1 (en) | 1987-09-16 |
| US4468507A (en) | 1984-08-28 |
| AU560884B2 (en) | 1987-04-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2521912A (en) | Phenol aldehyde polyepoxide compositions and reaction products | |
| TWI614275B (zh) | 用於製備聚合物的液體環氧樹脂組合物 | |
| JPS6244007B2 (OSRAM) | ||
| US2806016A (en) | Polyglycidyl ethers of tetraphenols | |
| US2841595A (en) | Process for manufacture of glycidyl ethers of polyhydric phenols | |
| US2928803A (en) | Curing of polyepoxides | |
| TW200948864A (en) | Aromatic polycyanate compounds and process for the production thereof | |
| JPS60501663A (ja) | 枝分れノボラツク樹脂の製造方法 | |
| NL8301697A (nl) | Diglycidylether van dimethanolcyclohexaan en reactieprodukten ervan. | |
| US5360886A (en) | Precatalyzed catalyst compositions, process for preparing epoxy resins, curable compositions, articles resulting from curing the resultant compositions | |
| DE1060138B (de) | Verfahren zur Herstellung von modifizierten gehaerteten Epoxyharzen | |
| US2965611A (en) | Polyphenol glycidyl ethers | |
| JPH0155655B2 (OSRAM) | ||
| JP2017141256A (ja) | シクロドデカトリエントリアルデヒド及び関連化合物の調製及び使用 | |
| US3979462A (en) | Condensation resins of phenols and α,α'-dihydroxy-diisopropyl benzenes | |
| JP5902625B2 (ja) | ヒドロキシル官能性ポリエステル樹脂 | |
| TWI570099B (zh) | 聚環戊二烯化合物 | |
| US3401147A (en) | Epoxy resins from bisphenols of 3, 9-divinyl spirobi | |
| US3351674A (en) | Mixed glycidyl derivatives of cyanuric acid and phenols | |
| US3062840A (en) | Epoxy-substituted polyhydric phenols | |
| US3147278A (en) | Epoxy compounds obtained by reacting a phenol and a 1, 1-(2'-olefinic-cyclic acetal)-cyclohexene-3 | |
| US10000433B1 (en) | Bisphenols and high-performance resins from terpenes | |
| US3071563A (en) | Aluminum-containing phenolic resins | |
| JPS609034B2 (ja) | 改良された性質を有する１価又は多価フエノ−ルのグリシジルエ−テルの製造法 | |
| JPH03237121A (ja) | エポキシ樹脂組成物 |