JPS6241964B2 - - Google Patents
Info
- Publication number
- JPS6241964B2 JPS6241964B2 JP59503499A JP50349984A JPS6241964B2 JP S6241964 B2 JPS6241964 B2 JP S6241964B2 JP 59503499 A JP59503499 A JP 59503499A JP 50349984 A JP50349984 A JP 50349984A JP S6241964 B2 JPS6241964 B2 JP S6241964B2
- Authority
- JP
- Japan
- Prior art keywords
- methylol
- phenol
- reaction
- mixture
- phenols
- 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
- 229920003986 novolac Polymers 0.000 description 78
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 64
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- 238000000034 method Methods 0.000 description 54
- 238000006243 chemical reaction Methods 0.000 description 52
- 239000000203 mixture Substances 0.000 description 37
- 150000002989 phenols Chemical class 0.000 description 34
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 238000004519 manufacturing process Methods 0.000 description 24
- 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 21
- 239000003054 catalyst Substances 0.000 description 20
- 239000004593 Epoxy Substances 0.000 description 19
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 229930185605 Bisphenol Natural products 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 230000008569 process Effects 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 239000000376 reactant Substances 0.000 description 12
- 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 11
- 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 11
- -1 aralkenyl Chemical group 0.000 description 11
- 238000009833 condensation Methods 0.000 description 11
- 235000013824 polyphenols Nutrition 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 230000005494 condensation Effects 0.000 description 10
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 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 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 229930003836 cresol Natural products 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 229920000647 polyepoxide Polymers 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 238000006384 oligomerization reaction Methods 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- 239000003377 acid catalyst Substances 0.000 description 4
- 125000003302 alkenyloxy group Chemical group 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 238000007033 dehydrochlorination reaction Methods 0.000 description 4
- 238000006735 epoxidation reaction Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 230000020169 heat generation Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 238000001256 steam distillation Methods 0.000 description 4
- 238000010792 warming 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
- 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
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 125000005024 alkenyl aryl group Chemical group 0.000 description 3
- 125000004450 alkenylene group Chemical group 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- CQRYARSYNCAZFO-UHFFFAOYSA-N salicyl alcohol Chemical compound OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 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
- 239000010410 layer Substances 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
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 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
- DECTVMOFPJKFOZ-UHFFFAOYSA-N 2,6-bis(hydroxymethyl)phenol Chemical compound OCC1=CC=CC(CO)=C1O DECTVMOFPJKFOZ-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
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 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
- 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
- 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
- 230000001588 bifunctional effect Effects 0.000 description 1
- 238000009739 binding Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000005843 halogen 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
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000005342 ion exchange Methods 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
- 230000000670 limiting effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 238000005191 phase separation Methods 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
- KZHAHJANVBGCOC-UHFFFAOYSA-N phenyl hypochlorite Chemical class ClOC1=CC=CC=C1 KZHAHJANVBGCOC-UHFFFAOYSA-N 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 150000008442 polyphenolic compounds Chemical group 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002510 pyrogen Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000010512 small scale reaction 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
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 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
- 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 JPS60501663A (ja) | 1985-10-03 |
| JPS6241964B2 true 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 |
| JPS60501663A (ja) | 1985-10-03 |
| AU3434984A (en) | 1985-06-03 |
| WO1985002193A1 (en) | 1985-05-23 |
| EP0147538B1 (en) | 1987-09-16 |
| US4468507A (en) | 1984-08-28 |
| AU560884B2 (en) | 1987-04-16 |
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