JPH05239264A - セルロースエステル樹脂の安定剤とそれを用いて安定化されたセルロースエステル樹脂組成物 - Google Patents
セルロースエステル樹脂の安定剤とそれを用いて安定化されたセルロースエステル樹脂組成物Info
- Publication number
- JPH05239264A JPH05239264A JP4292993A JP29299392A JPH05239264A JP H05239264 A JPH05239264 A JP H05239264A JP 4292993 A JP4292993 A JP 4292993A JP 29299392 A JP29299392 A JP 29299392A JP H05239264 A JPH05239264 A JP H05239264A
- Authority
- JP
- Japan
- Prior art keywords
- cellulose
- parts
- composition
- acid ester
- dioxaphosphorinane
- 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
- 229920002678 cellulose Polymers 0.000 title claims abstract description 43
- 239000003381 stabilizer Substances 0.000 title claims abstract description 35
- 239000011347 resin Substances 0.000 title claims abstract description 26
- 229920005989 resin Polymers 0.000 title claims abstract description 26
- 239000011342 resin composition Substances 0.000 title description 5
- 239000000203 mixture Substances 0.000 claims abstract description 78
- -1 organic acid esters Chemical class 0.000 claims abstract description 27
- 239000001913 cellulose Substances 0.000 claims abstract description 17
- 230000000087 stabilizing effect Effects 0.000 claims abstract description 11
- 238000012545 processing Methods 0.000 claims abstract description 10
- 150000001733 carboxylic acid esters Chemical class 0.000 claims abstract description 7
- 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 5
- 230000006866 deterioration Effects 0.000 claims abstract description 3
- 239000000088 plastic resin Substances 0.000 claims abstract 6
- 238000000034 method Methods 0.000 claims description 24
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 18
- 239000004593 Epoxy Substances 0.000 claims description 16
- HWSUUGHIDOOOOJ-UHFFFAOYSA-N dioxaphosphinane Chemical compound C1COOPC1 HWSUUGHIDOOOOJ-UHFFFAOYSA-N 0.000 claims description 14
- 235000021388 linseed oil Nutrition 0.000 claims description 11
- 239000000944 linseed oil Substances 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
- 229920002301 cellulose acetate Polymers 0.000 claims description 7
- 229920008347 Cellulose acetate propionate Polymers 0.000 claims description 6
- 230000015556 catabolic process Effects 0.000 claims description 6
- 229920006217 cellulose acetate butyrate Polymers 0.000 claims description 6
- 238000006731 degradation reaction Methods 0.000 claims description 6
- 230000006641 stabilisation Effects 0.000 claims description 2
- 238000011105 stabilization Methods 0.000 claims description 2
- 239000012461 cellulose resin Substances 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 10
- 230000000704 physical effect Effects 0.000 abstract description 2
- 238000006116 polymerization reaction Methods 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000009472 formulation Methods 0.000 description 20
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 18
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 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
- YTWYMHQAVLOJKT-UHFFFAOYSA-N 5,5-dimethyl-1,3,2-dioxaphosphinan-2-ium 2-oxide Chemical compound CC1(C)CO[P+](=O)OC1 YTWYMHQAVLOJKT-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 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 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 239000004014 plasticizer Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 238000002845 discoloration Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000001030 gas--liquid chromatography Methods 0.000 description 4
- 150000008301 phosphite esters Chemical class 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 238000012937 correction Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000012760 heat stabilizer Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 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
- 238000010992 reflux Methods 0.000 description 3
- 150000003839 salts 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
- 241001149724 Cololabis adocetus Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 230000003413 degradative effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000010525 oxidative degradation reaction Methods 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XZSDBHWBXCFBCO-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol;phenol Chemical compound OCC(C)(C)CO.OC1=CC=CC=C1 XZSDBHWBXCFBCO-UHFFFAOYSA-N 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
- HHSDVKMNVQCQFW-UHFFFAOYSA-N N(=O)O.P(O)(O)O Chemical compound N(=O)O.P(O)(O)O HHSDVKMNVQCQFW-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000012552 review 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
- 238000003860 storage Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000003017 thermal stabilizer Substances 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000004711 α-olefin Substances 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 |
|---|---|---|---|
| US786381 | 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 |
|---|---|
| JPH05239264A true JPH05239264A (ja) | 1993-09-17 |
Family
ID=25138415
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4292993A Pending JPH05239264A (ja) | 1991-11-01 | 1992-10-30 | セルロースエステル樹脂の安定剤とそれを用いて安定化されたセルロースエステル樹脂組成物 |
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) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP2023017249A (ja) * | 2021-07-26 | 2023-02-07 | 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 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1450944A4 (en) * | 2001-10-02 | 2005-07-06 | Atmospheric Glow Technologies | FAST-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 |
| US20140150691A1 (en) * | 2010-02-12 | 2014-06-05 | Eastman Chemical Company | Sulfite softwood based cellulose triacetate for lcd films |
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
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US8674130B2 (en) | 2009-10-01 | 2014-03-18 | Daihachi Chemical Industry Co., Ltd. | Processes for production of cyclic alkylene phosphorohalidite and cyclic phosphoric acid ester |
| JP2023017249A (ja) * | 2021-07-26 | 2023-02-07 | 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2081793A1 (en) | 1993-05-02 |
| US5225467A (en) | 1993-07-06 |
| MX9206288A (es) | 1993-07-01 |
| EP0540270A1 (en) | 1993-05-05 |
| TW224112B (OSRAM) | 1994-05-21 |
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