JPS6381118A - ４核体フェノール類ノボラック型エポキシ化合物の製造法 - Google Patents
４核体フェノール類ノボラック型エポキシ化合物の製造法Info
- Publication number
- JPS6381118A JPS6381118A JP22484186A JP22484186A JPS6381118A JP S6381118 A JPS6381118 A JP S6381118A JP 22484186 A JP22484186 A JP 22484186A JP 22484186 A JP22484186 A JP 22484186A JP S6381118 A JPS6381118 A JP S6381118A
- Authority
- JP
- Japan
- Prior art keywords
- type epoxy
- product
- epoxy resin
- tetranuclear
- epoxy 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
- 229920003986 novolac Polymers 0.000 title claims abstract description 54
- 239000003822 epoxy resin Substances 0.000 title claims description 25
- 229920000647 polyepoxide Polymers 0.000 title claims description 25
- 150000002989 phenols Chemical class 0.000 title abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 239000004593 Epoxy Substances 0.000 claims abstract description 33
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 49
- 239000000126 substance Substances 0.000 claims description 4
- 229940126062 Compound A Drugs 0.000 claims 1
- 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 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- 229920005989 resin Polymers 0.000 abstract description 3
- 239000011347 resin Substances 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 43
- 230000015572 biosynthetic process Effects 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- 238000009826 distribution Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 230000014759 maintenance of location Effects 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 210000003323 beak Anatomy 0.000 description 7
- 241000238557 Decapoda Species 0.000 description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 5
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 4
- 150000002366 halogen compounds Chemical class 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- -1 pentanuclear Chemical class 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000004843 novolac epoxy resin Substances 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- JEFSTMHERNSDBC-UHFFFAOYSA-N 1,2-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC=CCC1(C)O JEFSTMHERNSDBC-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- HZBYPGZQDSNMFN-UHFFFAOYSA-N 3,5-dimethoxy-2,6-dimethylheptan-4-one Chemical compound COC(C(C)C)C(=O)C(OC)C(C)C HZBYPGZQDSNMFN-UHFFFAOYSA-N 0.000 description 1
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 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 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000004035 construction material Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22484186A JPS6381118A (ja) | 1986-09-25 | 1986-09-25 | ４核体フェノール類ノボラック型エポキシ化合物の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22484186A JPS6381118A (ja) | 1986-09-25 | 1986-09-25 | ４核体フェノール類ノボラック型エポキシ化合物の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6381118A true JPS6381118A (ja) | 1988-04-12 |
| JPH0521925B2 JPH0521925B2 (enrdf_load_stackoverflow) | 1993-03-26 |
Family
ID=16820013
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22484186A Granted JPS6381118A (ja) | 1986-09-25 | 1986-09-25 | ４核体フェノール類ノボラック型エポキシ化合物の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6381118A (enrdf_load_stackoverflow) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63301218A (ja) * | 1987-06-02 | 1988-12-08 | Asahi Chiba Kk | エポキシ樹脂組成物 |
| JPH04181789A (ja) * | 1990-11-16 | 1992-06-29 | Toshiba Chem Corp | エポキシ樹脂組成物及び銅張積層板 |
| JPH04220422A (ja) * | 1990-12-20 | 1992-08-11 | Nippon Kayaku Co Ltd | エポキシ樹脂の製造方法 |
| WO1997029144A1 (en) * | 1996-02-09 | 1997-08-14 | Nippon Kayaku Kabushiki Kaisha | Epoxy resin, epoxy resin composition and products of curing thereof |
| JPH11209585A (ja) * | 1998-01-28 | 1999-08-03 | Asahi Denka Kogyo Kk | ポリオール樹脂組成物 |
| JP2000297199A (ja) * | 1999-04-14 | 2000-10-24 | Shin Etsu Chem Co Ltd | エポキシ樹脂組成物並びにこのエポキシ樹脂組成物を用いた積層フィルム及び半導体装置 |
| KR100563509B1 (ko) * | 1998-09-25 | 2006-03-23 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 에폭시 수지 조성물 및 이 에폭시 수지 조성물을 사용한 적층 필름 및 반도체 장치 |
| JP2016523313A (ja) * | 2013-06-28 | 2016-08-08 | スリーエム イノベイティブ プロパティズ カンパニー | シム処理用途のための高弾性率エポキシ接着剤 |
| JP2023074974A (ja) * | 2021-11-18 | 2023-05-30 | Dic株式会社 | エポキシ樹脂 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101446081B1 (ko) * | 2013-11-26 | 2014-10-01 | 주식회사 진영뉴웍스 | 은경막 코팅용 스프레이 노즐 구조 및 이를 포함하는 스프레이 장치 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5219755A (en) * | 1975-08-05 | 1977-02-15 | Dow Chemical Co | Epoxy novolak resin production method |
-
1986
- 1986-09-25 JP JP22484186A patent/JPS6381118A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5219755A (en) * | 1975-08-05 | 1977-02-15 | Dow Chemical Co | Epoxy novolak resin production method |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63301218A (ja) * | 1987-06-02 | 1988-12-08 | Asahi Chiba Kk | エポキシ樹脂組成物 |
| JPH04181789A (ja) * | 1990-11-16 | 1992-06-29 | Toshiba Chem Corp | エポキシ樹脂組成物及び銅張積層板 |
| JPH04220422A (ja) * | 1990-12-20 | 1992-08-11 | Nippon Kayaku Co Ltd | エポキシ樹脂の製造方法 |
| WO1997029144A1 (en) * | 1996-02-09 | 1997-08-14 | Nippon Kayaku Kabushiki Kaisha | Epoxy resin, epoxy resin composition and products of curing thereof |
| US6124420A (en) * | 1996-02-09 | 2000-09-26 | Nippon Kayaku Kabushiki Kaisha | Epoxy resin, epoxy resin composition and hardened product thereof |
| JPH11209585A (ja) * | 1998-01-28 | 1999-08-03 | Asahi Denka Kogyo Kk | ポリオール樹脂組成物 |
| KR100563509B1 (ko) * | 1998-09-25 | 2006-03-23 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 에폭시 수지 조성물 및 이 에폭시 수지 조성물을 사용한 적층 필름 및 반도체 장치 |
| JP2000297199A (ja) * | 1999-04-14 | 2000-10-24 | Shin Etsu Chem Co Ltd | エポキシ樹脂組成物並びにこのエポキシ樹脂組成物を用いた積層フィルム及び半導体装置 |
| JP2016523313A (ja) * | 2013-06-28 | 2016-08-08 | スリーエム イノベイティブ プロパティズ カンパニー | シム処理用途のための高弾性率エポキシ接着剤 |
| US10059862B2 (en) | 2013-06-28 | 2018-08-28 | 3M Innovative Properties Company | High modulus epoxy adhesives for shimming applications |
| JP2023074974A (ja) * | 2021-11-18 | 2023-05-30 | Dic株式会社 | エポキシ樹脂 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0521925B2 (enrdf_load_stackoverflow) | 1993-03-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |