JPS62119220A - ポリヒドロキシ化合物の製造法 - Google Patents
ポリヒドロキシ化合物の製造法Info
- Publication number
- JPS62119220A JPS62119220A JP25919885A JP25919885A JPS62119220A JP S62119220 A JPS62119220 A JP S62119220A JP 25919885 A JP25919885 A JP 25919885A JP 25919885 A JP25919885 A JP 25919885A JP S62119220 A JPS62119220 A JP S62119220A
- Authority
- JP
- Japan
- Prior art keywords
- phenol
- dihydroxymethyl
- component
- acid
- compound
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 61
- 150000002989 phenols Chemical class 0.000 claims abstract description 23
- 239000003377 acid catalyst Substances 0.000 claims abstract description 7
- 230000018044 dehydration Effects 0.000 claims abstract description 4
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 11
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract description 12
- 238000009826 distribution Methods 0.000 abstract description 10
- 239000003822 epoxy resin Substances 0.000 abstract description 7
- 229920000647 polyepoxide Polymers 0.000 abstract description 7
- -1 p-substituted phenol Chemical class 0.000 abstract description 6
- 235000006408 oxalic acid Nutrition 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 3
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 239000004848 polyfunctional curative Substances 0.000 abstract 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 14
- 229920003986 novolac Polymers 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 5
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 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 4
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 229920001568 phenolic resin Polymers 0.000 description 3
- 239000005011 phenolic resin Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000001256 steam distillation Methods 0.000 description 3
- 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 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLXNBJHLHFGROB-UHFFFAOYSA-N 2,6-bis(hydroxymethyl)-4-pentylphenol Chemical compound CCCCCC1=CC(CO)=C(O)C(CO)=C1 XLXNBJHLHFGROB-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- PCNDYBPBDAQKME-UHFFFAOYSA-N 4-butyl-2,6-bis(hydroxymethyl)phenol Chemical compound CCCCC1=CC(CO)=C(O)C(CO)=C1 PCNDYBPBDAQKME-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical class OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols 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
- 238000000746 purification Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25919885A JPS62119220A (ja) | 1985-11-18 | 1985-11-18 | ポリヒドロキシ化合物の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25919885A JPS62119220A (ja) | 1985-11-18 | 1985-11-18 | ポリヒドロキシ化合物の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62119220A true JPS62119220A (ja) | 1987-05-30 |
| JPH0569127B2 JPH0569127B2 (enExample) | 1993-09-30 |
Family
ID=17330741
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25919885A Granted JPS62119220A (ja) | 1985-11-18 | 1985-11-18 | ポリヒドロキシ化合物の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62119220A (enExample) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62212410A (ja) * | 1986-03-14 | 1987-09-18 | Asahi Chiba Kk | ノボラック樹脂の製造法 |
| US5395915A (en) * | 1992-02-27 | 1995-03-07 | Mitsui Toatsu Chemicals, Inc. | Method for simultaneous preparation of bisphenol F and novolak phenol resins |
| WO2003042267A1 (fr) * | 2001-11-16 | 2003-05-22 | Asahi Organic Chemicals Industry Co., Ltd. | Novolaques phenoliques et leur procede de production |
| WO2013125620A1 (ja) * | 2012-02-23 | 2013-08-29 | 新日鉄住金化学株式会社 | 多価ヒドロキシ樹脂、エポキシ樹脂、それらの製造方法、エポキシ樹脂組成物及びその硬化物 |
| WO2015175551A1 (en) * | 2014-05-12 | 2015-11-19 | Si Group, Inc. | Modified phenolic resins and methods of making and using the same as reinforcing resins |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5257153A (en) * | 1975-10-30 | 1977-05-11 | Sir Soc Italiana Resine Spa | Polyhydroxyphenol and process for preparing same |
-
1985
- 1985-11-18 JP JP25919885A patent/JPS62119220A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5257153A (en) * | 1975-10-30 | 1977-05-11 | Sir Soc Italiana Resine Spa | Polyhydroxyphenol and process for preparing same |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62212410A (ja) * | 1986-03-14 | 1987-09-18 | Asahi Chiba Kk | ノボラック樹脂の製造法 |
| US5395915A (en) * | 1992-02-27 | 1995-03-07 | Mitsui Toatsu Chemicals, Inc. | Method for simultaneous preparation of bisphenol F and novolak phenol resins |
| WO2003042267A1 (fr) * | 2001-11-16 | 2003-05-22 | Asahi Organic Chemicals Industry Co., Ltd. | Novolaques phenoliques et leur procede de production |
| US7241833B2 (en) | 2001-11-16 | 2007-07-10 | Asahi Organic Chemicals Industry Co.., Ltp | Phenolic novolaks and process for production thereof |
| WO2013125620A1 (ja) * | 2012-02-23 | 2013-08-29 | 新日鉄住金化学株式会社 | 多価ヒドロキシ樹脂、エポキシ樹脂、それらの製造方法、エポキシ樹脂組成物及びその硬化物 |
| JPWO2013125620A1 (ja) * | 2012-02-23 | 2015-07-30 | 新日鉄住金化学株式会社 | 多価ヒドロキシ樹脂、エポキシ樹脂、それらの製造方法、エポキシ樹脂組成物及びその硬化物 |
| WO2015175551A1 (en) * | 2014-05-12 | 2015-11-19 | Si Group, Inc. | Modified phenolic resins and methods of making and using the same as reinforcing resins |
| US9765174B2 (en) | 2014-05-12 | 2017-09-19 | Si Group, Inc. | Modified phenolic resins and methods of making and using the same as reinforcing resins |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0569127B2 (enExample) | 1993-09-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP7513428B2 (ja) | 樹脂組成物および硬化物 | |
| KR940010010B1 (ko) | 페놀류 노볼락형 수지, 그 경화물 및 그 제조방법 | |
| JP2001055425A (ja) | レゾルシンノボラック樹脂、エポキシ樹脂組成物及びその硬化物 | |
| JPS62119220A (ja) | ポリヒドロキシ化合物の製造法 | |
| US4102866A (en) | Method of making glycidyl ethers of novolak resins | |
| JP5012003B2 (ja) | 低溶融粘度フェノールノボラック樹脂、その製造方法ならびにその用途 | |
| WO2000061650A1 (en) | Development of low viscosity benzoxazine resins | |
| US4297473A (en) | Quick-curing phenolic resin and process for preparing same | |
| JP2010229304A (ja) | フェノール樹脂、該樹脂の製造方法及び該樹脂を含むエポキシ樹脂組成物、ならびにその硬化物 | |
| JPH0681775B2 (ja) | ポリヒドロキシ化合物の製造法 | |
| JP3236382B2 (ja) | フェノール系樹脂の製造法 | |
| JP3473928B2 (ja) | フェノール樹脂組成物 | |
| JPH03229717A (ja) | プロペニル基含有フェノール樹脂 | |
| JP5433294B2 (ja) | ジヒドロキシナフタレン系重合体、その製造方法およびその用途 | |
| JPH09302058A (ja) | 硬化性に優れたフェノール系耐熱樹脂とその製造方法 | |
| JP2579405B2 (ja) | エポキシ樹脂硬化剤 | |
| JPH05320290A (ja) | ポリヒドロキシ化合物の製造法 | |
| JPS6377915A (ja) | フェノール類ノボラック組成物の製造法 | |
| JP3422808B2 (ja) | エポキシ樹脂硬化剤及びその製造方法 | |
| JPS6148528B2 (enExample) | ||
| JPH04225012A (ja) | ４核体フェノール類ノボラック及びその製造法 | |
| JPH07252339A (ja) | 高反応性変性フェノール樹脂の製造方法、該樹脂を含有する成形粉、電気・電子部品用材料及び半導体封止材 | |
| JPH09124759A (ja) | フェノールノボラック樹脂組成物 | |
| JPS61266432A (ja) | ポリヒドロキシ化合物の製造法 | |
| US20230374213A1 (en) | Process for preparing branched phenolic novolak |