JPH0138133B2 - - Google Patents
Info
- Publication number
- JPH0138133B2 JPH0138133B2 JP56067087A JP6708781A JPH0138133B2 JP H0138133 B2 JPH0138133 B2 JP H0138133B2 JP 56067087 A JP56067087 A JP 56067087A JP 6708781 A JP6708781 A JP 6708781A JP H0138133 B2 JPH0138133 B2 JP H0138133B2
- Authority
- JP
- Japan
- Prior art keywords
- phase
- polyester
- carbon atoms
- acid chloride
- chloride
- 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
- 229920000728 polyester Polymers 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000008346 aqueous phase Substances 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 12
- 239000007791 liquid phase Substances 0.000 claims abstract description 11
- 239000006185 dispersion Substances 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 9
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 8
- 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 abstract description 7
- 239000012071 phase Substances 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims abstract description 5
- 239000012074 organic phase Substances 0.000 claims abstract description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 3
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 claims abstract 2
- 230000003381 solubilizing effect Effects 0.000 claims description 8
- 238000012696 Interfacial polycondensation Methods 0.000 claims description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 230000007928 solubilization Effects 0.000 claims description 4
- 238000005063 solubilization Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 9
- -1 aromatic dicarboxylic acid halides Chemical class 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 abstract description 2
- 150000003983 crown ethers Chemical class 0.000 abstract description 2
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000012733 comparative method Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
- YWFPGFJLYRKYJZ-UHFFFAOYSA-N 9,9-bis(4-hydroxyphenyl)fluorene Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 YWFPGFJLYRKYJZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- VOWWYDCFAISREI-UHFFFAOYSA-N Bisphenol AP Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=CC=C1 VOWWYDCFAISREI-UHFFFAOYSA-N 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005406 washing Methods 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/19—Hydroxy compounds containing aromatic rings
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/79—Interfacial processes, i.e. processes involving a reaction at the interface of two non-miscible liquids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0242580A AT374812B (de) | 1980-05-07 | 1980-05-07 | Verfahren zur herstellung aromatischer polyester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS572332A JPS572332A (en) | 1982-01-07 |
| JPH0138133B2 true JPH0138133B2 (en, 2012) | 1989-08-11 |
Family
ID=3534115
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6708781A Granted JPS572332A (en) | 1980-05-07 | 1981-05-06 | Manufacture of aromatic polyester |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4430493A (en, 2012) |
| EP (1) | EP0041496B1 (en, 2012) |
| JP (1) | JPS572332A (en, 2012) |
| AT (3) | AT374812B (en, 2012) |
| DE (1) | DE3176689D1 (en, 2012) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT374812B (de) * | 1980-05-07 | 1984-06-12 | Isovolta | Verfahren zur herstellung aromatischer polyester |
| ATE33027T1 (de) * | 1981-05-07 | 1988-04-15 | Isovolta | Hochmolekularer aromatischer polyester, verfahren zur herstellung von folien aus diesen polyestern und folie aus diesen polyestern, ein elektrischer leiter mit einer isolierung aus diesen polyestern und verfahren zur herstellung solcher isolierungen. |
| AT387394B (de) * | 1983-06-03 | 1989-01-10 | Isovolta | Verfahren zur polykondensation von diphenolen und dicarbonsaeurehalogeniden |
| US4612350A (en) * | 1984-12-28 | 1986-09-16 | Chevron Research Company | Bis(hydroxyphenyl)fluorene polyarylate polymers and alloys |
| AT386217B (de) * | 1986-10-21 | 1988-07-25 | Isovolta | Verfahren zur herstellung aromatischer polyester |
| US4737569A (en) * | 1986-12-30 | 1988-04-12 | General Electric Company | Process for the production of substantially monoester-free diaryl esters of aromatic dicarboxylic acids |
| US5073595A (en) * | 1987-12-23 | 1991-12-17 | Minnesota Mining And Manufacturing Company | Epoxide resin compositions and method |
| US4983672A (en) * | 1987-12-23 | 1991-01-08 | Minnesota Mining And Manufacturing Company | Epoxide resin compositions and method |
| US5045363A (en) * | 1987-12-23 | 1991-09-03 | Minnesota Mining And Manufacturing Company | Epoxide resin compositions and method |
| US4980234A (en) * | 1987-12-23 | 1990-12-25 | Minnesota Mining And Manufacturing Co. | Epoxide resin compositions and method |
| AT392475B (de) * | 1988-12-09 | 1991-04-10 | Isovolta | Verfahren zur polykondensation von diphenolen mit halogeniden von dicarbonsaeuren |
| US5318938A (en) * | 1989-05-05 | 1994-06-07 | Minnesota Mining And Manufacturing Company | Thermographic elements |
| US4967306A (en) * | 1989-05-05 | 1990-10-30 | Minnesota Mining And Manufacturing Company | High purity aromatic polyesters |
| US5295040A (en) * | 1989-05-05 | 1994-03-15 | Minnesota Mining And Manufacturing Company | High purity aromatic polyesters |
| IT1243990B (it) * | 1990-10-30 | 1994-06-28 | Minnesota Mining & Mfg | Procedimento per preparare prodotti del bisfenolo fluorene |
| US5266677A (en) * | 1992-05-27 | 1993-11-30 | University Of North Carolina At Chapel Hill | Thiophene-based polymers |
| US5670603A (en) * | 1993-03-08 | 1997-09-23 | Alliedsignal Inc. | Polymers exhibiting nonlinear optical properties |
| ITSV20010013A1 (it) | 2001-04-24 | 2002-10-24 | Ferrania Spa | 9,9-bis-(4-idrossifenil)-fluorene ad alta purezza e metodo perla sua preparazione e purificazione |
| JP4231440B2 (ja) * | 2004-03-24 | 2009-02-25 | 富士フイルム株式会社 | 樹脂組成物および該樹脂組成物を用いたフィルム、光学部品、画像表示素子 |
| JP4425167B2 (ja) * | 2005-03-22 | 2010-03-03 | 富士フイルム株式会社 | ガスバリア性フィルム、基材フィルムおよび有機エレクトロルミネッセンス素子 |
| JP4663381B2 (ja) * | 2005-04-12 | 2011-04-06 | 富士フイルム株式会社 | ガスバリア性フィルム、基材フィルムおよび有機エレクトロルミネッセンス素子 |
| JP4698310B2 (ja) * | 2005-07-11 | 2011-06-08 | 富士フイルム株式会社 | ガスバリア性フィルム、基材フィルムおよび有機エレクトロルミネッセンス素子 |
| JP4717674B2 (ja) * | 2006-03-27 | 2011-07-06 | 富士フイルム株式会社 | ガスバリア性フィルム、基材フィルムおよび有機エレクトロルミネッセンス素子 |
| JP5480774B2 (ja) | 2009-10-22 | 2014-04-23 | 日東電工株式会社 | 透明基板 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3216970A (en) * | 1956-12-14 | 1965-11-09 | Gevaert Photo Prod Nv | Production of linear aromatic polyesters containing isophthalic acid |
| US3234167A (en) | 1962-01-09 | 1966-02-08 | Du Pont | Light-stable aromatic polyesters |
| GB1122201A (en) * | 1966-01-04 | 1968-07-31 | Inst Elementoorganicheskikh So | Method of producing polyarylates |
| DE1595822B1 (de) * | 1966-01-28 | 1969-12-11 | Inst Elementoorganicheskhikh S | Verfahren zur Herstellung von Polyestern durch Polykondensation aromatischer Dicarbonsaeurechloride mit zweiwertigen Phenolen |
| US3546165A (en) * | 1966-02-01 | 1970-12-08 | Du Pont | Soluble high-melting,thermally stable linear polyesters |
| DE2442541A1 (de) * | 1974-09-05 | 1976-03-18 | Vnii Sintetischeskich Smol | Verfahren zur herstellung von aromatischen polyestern |
| US4066623A (en) | 1976-10-26 | 1978-01-03 | Celanese Corporation | Inverse interfacial polymerization for preparing certain halogenated aromatic polyesters |
| US4201855A (en) | 1977-06-17 | 1980-05-06 | Allied Chemical Corporation | Novel polyesters and preparation thereof by interfacial condensation of bifunctional acid halides or anhydrides with bisphenols |
| AT374812B (de) * | 1980-05-07 | 1984-06-12 | Isovolta | Verfahren zur herstellung aromatischer polyester |
-
1980
- 1980-05-07 AT AT0242580A patent/AT374812B/de not_active IP Right Cessation
-
1981
- 1981-05-06 JP JP6708781A patent/JPS572332A/ja active Granted
- 1981-05-07 DE DE8181890076T patent/DE3176689D1/de not_active Expired
- 1981-05-07 AT AT81890076T patent/ATE33140T1/de not_active IP Right Cessation
- 1981-05-07 EP EP81890076A patent/EP0041496B1/de not_active Expired
- 1981-12-09 AT AT0527881A patent/AT385042B/de not_active IP Right Cessation
-
1983
- 1983-02-03 US US06/463,590 patent/US4430493A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US4430493A (en) | 1984-02-07 |
| JPS572332A (en) | 1982-01-07 |
| EP0041496B1 (de) | 1988-03-23 |
| DE3176689D1 (en) | 1988-04-28 |
| EP0041496A1 (de) | 1981-12-09 |
| ATE33140T1 (de) | 1988-04-15 |
| ATA242580A (de) | 1983-10-15 |
| ATA527881A (de) | 1987-07-15 |
| AT385042B (de) | 1988-02-10 |
| AT374812B (de) | 1984-06-12 |
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