JP2002161061A - 新規なビス（１−ヒドロキシ−２−エチルフェニル）類 - Google Patents
新規なビス（１−ヒドロキシ−２−エチルフェニル）類Info
- Publication number
- JP2002161061A JP2002161061A JP2000361694A JP2000361694A JP2002161061A JP 2002161061 A JP2002161061 A JP 2002161061A JP 2000361694 A JP2000361694 A JP 2000361694A JP 2000361694 A JP2000361694 A JP 2000361694A JP 2002161061 A JP2002161061 A JP 2002161061A
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- ethylphenyl
- bis
- reaction
- group
- 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.)
- Pending
Links
- -1 1-hydroxy-2-ethylphenyl Chemical group 0.000 title claims abstract description 39
- 150000001875 compounds Chemical class 0.000 title abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 5
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims abstract description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 claims 1
- 101150035983 str1 gene Proteins 0.000 claims 1
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 abstract description 36
- 239000002994 raw material Substances 0.000 abstract description 10
- 229920005989 resin Polymers 0.000 abstract description 4
- 239000011347 resin Substances 0.000 abstract description 4
- 239000003963 antioxidant agent Substances 0.000 abstract description 3
- 239000003822 epoxy resin Substances 0.000 abstract description 3
- 239000004431 polycarbonate resin Substances 0.000 abstract description 3
- 229920005668 polycarbonate resin Polymers 0.000 abstract description 3
- 229920000647 polyepoxide Polymers 0.000 abstract description 3
- 229920003002 synthetic resin Polymers 0.000 abstract description 3
- 239000000057 synthetic resin Substances 0.000 abstract description 3
- 229920001169 thermoplastic Polymers 0.000 abstract description 3
- 229920001187 thermosetting polymer Polymers 0.000 abstract description 3
- 239000004416 thermosoftening plastic Substances 0.000 abstract description 3
- 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 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 27
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 229930185605 Bisphenol Natural products 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 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 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000003377 acid catalyst Substances 0.000 description 7
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 239000007789 gas Substances 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- SLJYPZJZQIHNGU-UHFFFAOYSA-N 4-(4-hydroxyphenyl)cyclohexan-1-one Chemical compound C1=CC(O)=CC=C1C1CCC(=O)CC1 SLJYPZJZQIHNGU-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-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
- 230000005540 biological transmission Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- UJBOOUHRTQVGRU-UHFFFAOYSA-N 3-methylcyclohexan-1-one Chemical compound CC1CCCC(=O)C1 UJBOOUHRTQVGRU-UHFFFAOYSA-N 0.000 description 2
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- VIONQPIBQGSEBW-UHFFFAOYSA-N OC1(C(C=CC=C1)CC)C1(C2=CC=CC=C2C=2C=CC=CC12)C1(C(C=CC=C1)CC)O Chemical compound OC1(C(C=CC=C1)CC)C1(C2=CC=CC=C2C=2C=CC=CC12)C1(C(C=CC=C1)CC)O VIONQPIBQGSEBW-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- NWPWGNPPZVZAKO-UHFFFAOYSA-N fluoren-1-one Chemical compound C1=CC=C2C3=CC=CC(=O)C3=CC2=C1 NWPWGNPPZVZAKO-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000013076 target 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
- XQOAPEATHLRJMI-UHFFFAOYSA-N 2-ethyl-4-[2-(3-ethyl-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C1=C(O)C(CC)=CC(C(C)(C)C=2C=C(CC)C(O)=CC=2)=C1 XQOAPEATHLRJMI-UHFFFAOYSA-N 0.000 description 1
- AIFNFRLJNHOYJH-UHFFFAOYSA-N 3-(3-hydroxyphenyl)cyclohexan-1-one Chemical compound Oc1cccc(c1)C1CCCC(=O)C1 AIFNFRLJNHOYJH-UHFFFAOYSA-N 0.000 description 1
- XAORBISQKNRUML-UHFFFAOYSA-N 3-(4-hydroxyphenyl)cyclohexan-1-one Chemical compound C1=CC(O)=CC=C1C1CC(=O)CCC1 XAORBISQKNRUML-UHFFFAOYSA-N 0.000 description 1
- IEVRHAUJJJBXFH-UHFFFAOYSA-N 3-ethylcyclohexan-1-one Chemical compound CCC1CCCC(=O)C1 IEVRHAUJJJBXFH-UHFFFAOYSA-N 0.000 description 1
- CJAUDSQXFVZPTO-UHFFFAOYSA-N 3-phenylcyclohexan-1-one Chemical compound C1C(=O)CCCC1C1=CC=CC=C1 CJAUDSQXFVZPTO-UHFFFAOYSA-N 0.000 description 1
- AFFBXUKVORMWSC-UHFFFAOYSA-N 3-propan-2-ylcyclohexan-1-one Chemical compound CC(C)C1CCCC(=O)C1 AFFBXUKVORMWSC-UHFFFAOYSA-N 0.000 description 1
- QVXPIKXXHLNRJE-UHFFFAOYSA-N 4-(2-hydroxyphenyl)cyclohexan-1-one Chemical compound OC1=CC=CC=C1C1CCC(=O)CC1 QVXPIKXXHLNRJE-UHFFFAOYSA-N 0.000 description 1
- ISAZLUPWYLEGQX-UHFFFAOYSA-N 4-(3-hydroxyphenyl)cyclohexan-1-one Chemical compound OC=1C=C(C=CC=1)C1CCC(CC1)=O ISAZLUPWYLEGQX-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- OKSDJGWHKXFVME-UHFFFAOYSA-N 4-ethylcyclohexan-1-one Chemical compound CCC1CCC(=O)CC1 OKSDJGWHKXFVME-UHFFFAOYSA-N 0.000 description 1
- YKAYMASDSHFOGI-UHFFFAOYSA-N 4-phenylcyclohexan-1-one Chemical compound C1CC(=O)CCC1C1=CC=CC=C1 YKAYMASDSHFOGI-UHFFFAOYSA-N 0.000 description 1
- FPKISACHVIIMRA-UHFFFAOYSA-N 4-propan-2-ylcyclohexan-1-one Chemical compound CC(C)C1CCC(=O)CC1 FPKISACHVIIMRA-UHFFFAOYSA-N 0.000 description 1
- NQEDLIZOPMNZMC-UHFFFAOYSA-N 4-propylcyclohexan-1-one Chemical compound CCCC1CCC(=O)CC1 NQEDLIZOPMNZMC-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- LPVRQAZMSWGYKD-UHFFFAOYSA-N C(C)C=1C=C(C=CC1O)C(CC(C)C1=CC(=C(C=C1)O)CC)C1=CC(=C(C=C1)O)CC Chemical compound C(C)C=1C=C(C=CC1O)C(CC(C)C1=CC(=C(C=C1)O)CC)C1=CC(=C(C=C1)O)CC LPVRQAZMSWGYKD-UHFFFAOYSA-N 0.000 description 1
- MWDYNAQOVGOPAO-UHFFFAOYSA-N CCC1C=CC=CC1(C2(CCC(CC2)C(C)C)C3(C=CC=CC3CC)O)O Chemical compound CCC1C=CC=CC1(C2(CCC(CC2)C(C)C)C3(C=CC=CC3CC)O)O MWDYNAQOVGOPAO-UHFFFAOYSA-N 0.000 description 1
- HECIZKYWCONYCH-UHFFFAOYSA-N CCC1C=CC=CC1(C2(CCC(CC2)C)C3(C=CC=CC3CC)O)O Chemical compound CCC1C=CC=CC1(C2(CCC(CC2)C)C3(C=CC=CC3CC)O)O HECIZKYWCONYCH-UHFFFAOYSA-N 0.000 description 1
- KJBLJEFOAPQFPF-UHFFFAOYSA-N CCC1C=CC=CC1(C2(CCC(CC2)C3=CC=C(C=C3)O)C4(C=CC=CC4CC)O)O Chemical compound CCC1C=CC=CC1(C2(CCC(CC2)C3=CC=C(C=C3)O)C4(C=CC=CC4CC)O)O KJBLJEFOAPQFPF-UHFFFAOYSA-N 0.000 description 1
- YJIIQAFUWKDXNP-UHFFFAOYSA-N CCC1C=CC=CC1(C2(CCCC(C2)C(C)C)C3(C=CC=CC3CC)O)O Chemical compound CCC1C=CC=CC1(C2(CCCC(C2)C(C)C)C3(C=CC=CC3CC)O)O YJIIQAFUWKDXNP-UHFFFAOYSA-N 0.000 description 1
- YMAZHNMCIWTNHF-UHFFFAOYSA-N CCC1C=CC=CC1(C2(CCCC(C2)C)C3(C=CC=CC3CC)O)O Chemical compound CCC1C=CC=CC1(C2(CCCC(C2)C)C3(C=CC=CC3CC)O)O YMAZHNMCIWTNHF-UHFFFAOYSA-N 0.000 description 1
- ZHYFLSDOEHTIAM-UHFFFAOYSA-N CCC1CCC(CC1)(C2(C=CC=CC2CC)O)C3(C=CC=CC3CC)O Chemical compound CCC1CCC(CC1)(C2(C=CC=CC2CC)O)C3(C=CC=CC3CC)O ZHYFLSDOEHTIAM-UHFFFAOYSA-N 0.000 description 1
- OSEAQJIIYLJNFD-UHFFFAOYSA-N CCC1CCCC(C1)(C2(C=CC=CC2CC)O)C3(C=CC=CC3CC)O Chemical compound CCC1CCCC(C1)(C2(C=CC=CC2CC)O)C3(C=CC=CC3CC)O OSEAQJIIYLJNFD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 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
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N methyl cyclohexan-4-ol Natural products CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
- HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
- Epoxy Resins (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000361694A JP2002161061A (ja) | 2000-11-28 | 2000-11-28 | 新規なビス（１−ヒドロキシ−２−エチルフェニル）類 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000361694A JP2002161061A (ja) | 2000-11-28 | 2000-11-28 | 新規なビス（１−ヒドロキシ−２−エチルフェニル）類 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002161061A true JP2002161061A (ja) | 2002-06-04 |
| JP2002161061A5 JP2002161061A5 (cg-RX-API-DMAC7.html) | 2004-12-24 |
Family
ID=18833091
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000361694A Pending JP2002161061A (ja) | 2000-11-28 | 2000-11-28 | 新規なビス（１−ヒドロキシ−２−エチルフェニル）類 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2002161061A (cg-RX-API-DMAC7.html) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007254579A (ja) * | 2006-03-23 | 2007-10-04 | Nippon Kayaku Co Ltd | エポキシ樹脂、エポキシ樹脂組成物及びその硬化物 |
| JP2013227280A (ja) * | 2012-03-30 | 2013-11-07 | Honshu Chem Ind Co Ltd | 新規なトリスフェノール化合物 |
| JP5559036B2 (ja) * | 2008-04-04 | 2014-07-23 | 株式会社ダイセル | フォトレジスト用ポリオール化合物 |
| JP2014208635A (ja) * | 2013-03-28 | 2014-11-06 | 本州化学工業株式会社 | トリスフェノール化合物 |
-
2000
- 2000-11-28 JP JP2000361694A patent/JP2002161061A/ja active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007254579A (ja) * | 2006-03-23 | 2007-10-04 | Nippon Kayaku Co Ltd | エポキシ樹脂、エポキシ樹脂組成物及びその硬化物 |
| JP5559036B2 (ja) * | 2008-04-04 | 2014-07-23 | 株式会社ダイセル | フォトレジスト用ポリオール化合物 |
| JP2013227280A (ja) * | 2012-03-30 | 2013-11-07 | Honshu Chem Ind Co Ltd | 新規なトリスフェノール化合物 |
| JP2014208635A (ja) * | 2013-03-28 | 2014-11-06 | 本州化学工業株式会社 | トリスフェノール化合物 |
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