CA2081793A1 - Cellulose ester resin stabilizer and cellulose ester resin compositions stabilized therewith - Google Patents
Cellulose ester resin stabilizer and cellulose ester resin compositions stabilized therewithInfo
- Publication number
- CA2081793A1 CA2081793A1 CA002081793A CA2081793A CA2081793A1 CA 2081793 A1 CA2081793 A1 CA 2081793A1 CA 002081793 A CA002081793 A CA 002081793A CA 2081793 A CA2081793 A CA 2081793A CA 2081793 A1 CA2081793 A1 CA 2081793A1
- Authority
- CA
- Canada
- Prior art keywords
- parts
- cellulose
- resin
- dioxaphosphorinane
- phosphite
- 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.)
- Abandoned
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 64
- 239000011347 resin Substances 0.000 title claims abstract description 64
- 229920002678 cellulose Polymers 0.000 title claims abstract description 47
- 239000003381 stabilizer Substances 0.000 title claims abstract description 40
- 239000011342 resin composition Substances 0.000 title abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 91
- 239000000944 linseed oil Substances 0.000 claims abstract description 22
- 235000021388 linseed oil Nutrition 0.000 claims abstract description 22
- 230000000087 stabilizing effect Effects 0.000 claims abstract description 18
- PMQZJSNVZKBZON-UHFFFAOYSA-N 2-(3,3-dimethyl-6-nonylcyclohexa-1,5-dien-1-yl)oxy-1,3,2-dioxaphosphinane Chemical compound CCCCCCCCCC1=CCC(C)(C)C=C1OP1OCCCO1 PMQZJSNVZKBZON-UHFFFAOYSA-N 0.000 claims abstract description 15
- -1 fatty acid ester compound Chemical class 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 23
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 19
- 239000004593 Epoxy Substances 0.000 claims description 16
- 239000001913 cellulose Substances 0.000 claims description 16
- HWSUUGHIDOOOOJ-UHFFFAOYSA-N dioxaphosphinane Chemical compound C1COOPC1 HWSUUGHIDOOOOJ-UHFFFAOYSA-N 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 9
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 9
- 229930195729 fatty acid Natural products 0.000 claims description 9
- 239000000194 fatty acid Substances 0.000 claims description 9
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 7
- 230000015556 catabolic process Effects 0.000 claims description 7
- 229920002301 cellulose acetate Polymers 0.000 claims description 7
- 238000006731 degradation reaction Methods 0.000 claims description 7
- 229920008347 Cellulose acetate propionate Polymers 0.000 claims description 6
- 229920006217 cellulose acetate butyrate Polymers 0.000 claims description 6
- 239000004033 plastic Substances 0.000 claims description 6
- 229920003023 plastic Polymers 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 2
- HKQOBOMRSSHSTC-UHFFFAOYSA-N cellulose acetate Chemical compound OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O.CC(=O)OCC1OC(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(COC(C)=O)O1.CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 HKQOBOMRSSHSTC-UHFFFAOYSA-N 0.000 claims 1
- 239000012461 cellulose resin Substances 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 10
- 239000000155 melt Substances 0.000 abstract description 7
- CRCNBDVZXAOTDF-UHFFFAOYSA-N 5,5-dimethyl-2-(2-nonylphenoxy)-1,3,2-dioxaphosphinane Chemical compound CCCCCCCCCC1=CC=CC=C1OP1OCC(C)(C)CO1 CRCNBDVZXAOTDF-UHFFFAOYSA-N 0.000 abstract description 6
- 238000002845 discoloration Methods 0.000 abstract description 4
- 230000009897 systematic effect Effects 0.000 abstract description 3
- 230000003413 degradative effect Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 22
- 238000009472 formulation Methods 0.000 description 20
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 19
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 8
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 7
- FOTZPUNKEDWGDE-UHFFFAOYSA-N 2,2-dimethyl-1-phenylpropane-1,3-diol;phosphorous acid Chemical compound OP(O)O.OCC(C)(C)C(O)C1=CC=CC=C1 FOTZPUNKEDWGDE-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- LABRPRANVKSMGP-UHFFFAOYSA-N 1,3,2-dioxaphosphinane Chemical compound C1COPOC1 LABRPRANVKSMGP-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 5
- 239000004014 plasticizer Substances 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- 238000001030 gas--liquid chromatography Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000008301 phosphite esters Chemical class 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 150000003738 xylenes Chemical class 0.000 description 3
- MVXMECFCDQGZQL-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) dihydrogen phosphite;phenol Chemical compound OC1=CC=CC=C1.OCC(C)(C)COP(O)O MVXMECFCDQGZQL-UHFFFAOYSA-N 0.000 description 2
- RAIVCXDKWVDITL-UHFFFAOYSA-N 2,2-dimethylpropyl dihydrogen phosphite Chemical class CC(C)(C)COP(O)O RAIVCXDKWVDITL-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000012760 heat stabilizer Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000010525 oxidative degradation reaction Methods 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- 238000004679 31P NMR spectroscopy Methods 0.000 description 1
- DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- FEXXLIKDYGCVGJ-UHFFFAOYSA-N butyl 8-(3-octyloxiran-2-yl)octanoate Chemical compound CCCCCCCCC1OC1CCCCCCCC(=O)OCCCC FEXXLIKDYGCVGJ-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229920001727 cellulose butyrate Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 229920006218 cellulose propionate Polymers 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000012667 polymer degradation Methods 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003365 short chain fatty acid esters Chemical class 0.000 description 1
- BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 description 1
- 229910001488 sodium perchlorate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010408 sweeping Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000003017 thermal stabilizer Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/527—Cyclic esters
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US786,381 | 1991-11-01 | ||
| US07/786,381 US5225467A (en) | 1991-11-01 | 1991-11-01 | Cellulose ester resin stabilizer and cellulose ester resin compositions stabilized therewith |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2081793A1 true CA2081793A1 (en) | 1993-05-02 |
Family
ID=25138415
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002081793A Abandoned CA2081793A1 (en) | 1991-11-01 | 1992-10-30 | Cellulose ester resin stabilizer and cellulose ester resin compositions stabilized therewith |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5225467A (OSRAM) |
| EP (1) | EP0540270A1 (OSRAM) |
| JP (1) | JPH05239264A (OSRAM) |
| CA (1) | CA2081793A1 (OSRAM) |
| MX (1) | MX9206288A (OSRAM) |
| TW (1) | TW224112B (OSRAM) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040184972A1 (en) * | 2001-10-02 | 2004-09-23 | Kelly Daniel W | Rapid sterilization of an air filter medium |
| JP2006243688A (ja) * | 2005-02-01 | 2006-09-14 | Fuji Photo Film Co Ltd | セルロースアシレート光学フィルムおよびその製造方法 |
| WO2011040287A1 (ja) | 2009-10-01 | 2011-04-07 | 大八化学工業株式会社 | 環状アルキレンホスホロハリダイトおよび環状リン酸エステルの製造方法 |
| US20140150691A1 (en) * | 2010-02-12 | 2014-06-05 | Eastman Chemical Company | Sulfite softwood based cellulose triacetate for lcd films |
| JP7162366B1 (ja) * | 2021-07-26 | 2022-10-28 | 株式会社 ネクアス | 酢酸セルロース組成物、及びその製造方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2065125A (en) * | 1931-11-30 | 1936-12-22 | Dreyfus Henry | Manufacture or treatment of products or articles made of or containing cellulose derivatives or other lacquer bases |
| BE530324A (OSRAM) * | 1953-07-15 | |||
| US2826592A (en) * | 1954-01-27 | 1958-03-11 | Shell Dev | Epoxy esters of phosphorus-containing acids and their use in treating textiles |
| US2834798A (en) * | 1957-12-20 | 1958-05-13 | Shea Chemical Corp | Heterocyclic phosphorus compounds |
| US3047415A (en) * | 1959-02-26 | 1962-07-31 | Swift & Co | Vinyl resin-epoxy fatty acid coating composition, method and article |
| US3047608A (en) * | 1960-09-15 | 1962-07-31 | Weston Chemical Corp | Phosphites |
| US3305378A (en) * | 1963-02-25 | 1967-02-21 | Eastman Kodak Co | Color stabilized cellulose esters and compositions containing neopentyl phosphite |
| DE2402367A1 (de) * | 1973-01-23 | 1974-07-25 | Gen Electric | Hitzestabilisiertes polycarbonatharz |
| CH581163A5 (OSRAM) * | 1974-07-30 | 1976-10-29 | Sandoz Ag | |
| US4357168A (en) * | 1979-04-10 | 1982-11-02 | The Dow Chemical Co. | Cellulosic compositions useful in preparing hot melts |
| US4361664A (en) * | 1981-07-02 | 1982-11-30 | Borg-Warner Chemicals, Inc. | Flame-retardant polymer compositions |
| US4427813A (en) * | 1981-12-14 | 1984-01-24 | The Dow Chemical Co. | Polycarbonate containing a bis(cyclic phosphate) as a thermal stabilizer |
| US4882374A (en) * | 1989-02-06 | 1989-11-21 | Eastman Kodak Company | Dioxaphosphorinane compounds and polyolefin compositions sabilized therewith |
-
1991
- 1991-11-01 US US07/786,381 patent/US5225467A/en not_active Expired - Fee Related
-
1992
- 1992-10-26 EP EP92309774A patent/EP0540270A1/en not_active Withdrawn
- 1992-10-30 CA CA002081793A patent/CA2081793A1/en not_active Abandoned
- 1992-10-30 MX MX9206288A patent/MX9206288A/es not_active IP Right Cessation
- 1992-10-30 JP JP4292993A patent/JPH05239264A/ja active Pending
-
1993
- 1993-01-15 TW TW082100220A patent/TW224112B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| US5225467A (en) | 1993-07-06 |
| MX9206288A (es) | 1993-07-01 |
| EP0540270A1 (en) | 1993-05-05 |
| TW224112B (OSRAM) | 1994-05-21 |
| JPH05239264A (ja) | 1993-09-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 19981030 |