CA2074292A1 - Non-toxic polymeric compositions stabilized with organosulfide antioxidants - Google Patents
Non-toxic polymeric compositions stabilized with organosulfide antioxidantsInfo
- Publication number
- CA2074292A1 CA2074292A1 CA002074292A CA2074292A CA2074292A1 CA 2074292 A1 CA2074292 A1 CA 2074292A1 CA 002074292 A CA002074292 A CA 002074292A CA 2074292 A CA2074292 A CA 2074292A CA 2074292 A1 CA2074292 A1 CA 2074292A1
- Authority
- CA
- Canada
- Prior art keywords
- carbons
- group
- alkyl group
- organosulfide
- composition according
- 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
- 239000003963 antioxidant agent Substances 0.000 title claims abstract description 62
- 239000000203 mixture Substances 0.000 title claims abstract description 56
- 231100000252 nontoxic Toxicity 0.000 title claims abstract description 34
- 230000003000 nontoxic effect Effects 0.000 title claims abstract description 34
- 235000013305 food Nutrition 0.000 claims abstract description 43
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 40
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims abstract description 23
- 235000013361 beverage Nutrition 0.000 claims abstract description 11
- 238000004806 packaging method and process Methods 0.000 claims abstract description 9
- 239000003814 drug Substances 0.000 claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 61
- -1 polypropylene, ethylene-propylene copolymers Polymers 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
- 229920001155 polypropylene Polymers 0.000 claims description 19
- 239000004743 Polypropylene Substances 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 235000006486 human diet Nutrition 0.000 claims description 15
- 239000002952 polymeric resin Substances 0.000 claims description 11
- 229920003002 synthetic resin Polymers 0.000 claims description 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229920005989 resin Polymers 0.000 claims description 10
- 239000011347 resin Substances 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000002723 alicyclic group Chemical group 0.000 claims description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 229920001684 low density polyethylene Polymers 0.000 claims description 8
- 239000004702 low-density polyethylene Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229920000573 polyethylene Polymers 0.000 claims description 8
- 239000004698 Polyethylene Substances 0.000 claims description 7
- 230000001590 oxidative effect Effects 0.000 claims description 7
- 229920005672 polyolefin resin Polymers 0.000 claims description 7
- 150000001721 carbon Chemical group 0.000 claims description 6
- 229920001903 high density polyethylene Polymers 0.000 claims description 6
- 239000004700 high-density polyethylene Substances 0.000 claims description 6
- 229920001187 thermosetting polymer Polymers 0.000 claims description 6
- 241000700159 Rattus Species 0.000 claims description 5
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 229920000098 polyolefin Polymers 0.000 claims description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- 239000004793 Polystyrene Substances 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 229920000092 linear low density polyethylene Polymers 0.000 claims description 4
- 239000004707 linear low-density polyethylene Substances 0.000 claims description 4
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- 239000004417 polycarbonate Substances 0.000 claims description 4
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- 239000007864 aqueous solution Substances 0.000 claims description 2
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- 238000003860 storage Methods 0.000 claims description 2
- 239000004611 light stabiliser Substances 0.000 claims 6
- 239000003017 thermal stabilizer Substances 0.000 claims 6
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 claims 3
- 150000002989 phenols Chemical class 0.000 claims 3
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims 3
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- 230000015556 catabolic process Effects 0.000 claims 1
- 238000006731 degradation reaction Methods 0.000 claims 1
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- 238000010525 oxidative degradation reaction Methods 0.000 abstract description 4
- 239000000047 product Substances 0.000 description 42
- 229920000642 polymer Polymers 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 238000000605 extraction Methods 0.000 description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
- 150000002500 ions Chemical class 0.000 description 15
- WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 231100000419 toxicity Toxicity 0.000 description 11
- 230000001988 toxicity Effects 0.000 description 11
- 238000007792 addition Methods 0.000 description 10
- 235000019645 odor Nutrition 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- 150000002978 peroxides Chemical class 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000013508 migration Methods 0.000 description 7
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- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 125000000962 organic group Chemical group 0.000 description 6
- 230000001476 alcoholic effect Effects 0.000 description 5
- 239000008188 pellet Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 4
- 230000001154 acute effect Effects 0.000 description 4
- 230000007059 acute toxicity Effects 0.000 description 4
- 231100000403 acute toxicity Toxicity 0.000 description 4
- 229920001400 block copolymer Polymers 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
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- 239000002184 metal Substances 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- QXAITBQSYVNQDR-UHFFFAOYSA-N amitraz Chemical compound C=1C=C(C)C=C(C)C=1N=CN(C)C=NC1=CC=C(C)C=C1C QXAITBQSYVNQDR-UHFFFAOYSA-N 0.000 description 3
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- QKWLEZCBHBKUDK-UHFFFAOYSA-N methaneselone Chemical compound [Se]=C QKWLEZCBHBKUDK-UHFFFAOYSA-N 0.000 description 1
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- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 1
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- 229920000090 poly(aryl ether) Polymers 0.000 description 1
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- 231100000161 signs of toxicity Toxicity 0.000 description 1
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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
- C08K5/04—Oxygen-containing compounds
- C08K5/14—Peroxides
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/372—Sulfides, e.g. R-(S)x-R'
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/735,140 US5284886A (en) | 1989-10-31 | 1991-07-24 | Non-toxic polymeric compositions stabilized with organosulfide antioxidants |
| US735,140 | 1991-07-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2074292A1 true CA2074292A1 (en) | 1993-01-25 |
Family
ID=24954540
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002074292A Abandoned CA2074292A1 (en) | 1991-07-24 | 1992-07-21 | Non-toxic polymeric compositions stabilized with organosulfide antioxidants |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5284886A (OSRAM) |
| EP (1) | EP0525664A1 (OSRAM) |
| JP (1) | JPH05194785A (OSRAM) |
| BR (1) | BR9202838A (OSRAM) |
| CA (1) | CA2074292A1 (OSRAM) |
| TW (1) | TW221451B (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5284886A (en) * | 1989-10-31 | 1994-02-08 | Elf Atochem North America, Inc. | Non-toxic polymeric compositions stabilized with organosulfide antioxidants |
| US6812314B2 (en) * | 2001-10-17 | 2004-11-02 | University Of Florida | Thermally responsive polymer materials and uses thereof |
| US8147769B1 (en) | 2007-05-16 | 2012-04-03 | Abbott Cardiovascular Systems Inc. | Stent and delivery system with reduced chemical degradation |
| FR2917381B1 (fr) * | 2007-06-15 | 2009-10-16 | Ceva Sante Animale Sa | Conditionnement plastique multicouche pour la conservation d'une composition pharmaceutique |
| US20090319031A1 (en) * | 2008-06-19 | 2009-12-24 | Yunbing Wang | Bioabsorbable Polymeric Stent With Improved Structural And Molecular Weight Integrity |
| US9539587B1 (en) * | 2016-04-05 | 2017-01-10 | Chevron Phillips Chemical Company Lp | Mercaptanized dicyclopentadiene compositions and use thereof as a mining chemical collector |
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| US4330462A (en) * | 1980-05-12 | 1982-05-18 | The Goodyear Tire & Rubber Company | Stabilized polyester composition |
| US4374205A (en) * | 1980-06-16 | 1983-02-15 | The B. F. Goodrich Company | Stabilization of post-chlorinated vinyl chloride polymers by phosphate salts |
| US4345040A (en) * | 1980-06-16 | 1982-08-17 | The B. F. Goodrich Company | Stabilization of post-chlorinated vinyl chloride polymers by phosphate salts |
| US4303759A (en) * | 1980-09-12 | 1981-12-01 | Air Products And Chemicals, Inc. | Polyalkylenecarbonate compositions with improved thermal stability and method for making same |
| US4360619A (en) * | 1981-02-26 | 1982-11-23 | Carstab Corporation | Stabilizer compositions and polymers containing same |
| US4314934A (en) * | 1981-02-26 | 1982-02-09 | Carstab Corporation | Organohalide polymers stabilized with an organotin compound and an ortho mercapto phenol compound |
| US4576984A (en) * | 1982-02-04 | 1986-03-18 | Morton Thiokol, Inc. | Stabilizer compositions for PVC resins |
| CA1190692A (en) * | 1982-02-09 | 1985-07-16 | Du Pont Canada Inc. | Polyethylene compositions for rotational moulding processes |
| US4515916A (en) * | 1982-05-18 | 1985-05-07 | Morton Thiokol Inc. | Stabilizers for halogen containing polymers comprising zinc mercaptoesters, basic inorganic alkali or alkaline earth metal compounds and, substituted dihydropyridines |
| US4711921A (en) * | 1982-11-12 | 1987-12-08 | The B. F. Goodrich Company | Stabilization of vinyl chloride polymers |
| US4514539A (en) * | 1983-05-05 | 1985-04-30 | Reichhold Chemicals, Inc. | Stain resistant polymeric insulating compositions |
| US4611023A (en) * | 1984-02-03 | 1986-09-09 | Ciba-Geigy Corporation | Di-(substituted hydroxyphenylthio) alkane and cycloalkane stabilizers and stabilized compositions |
| US4880856A (en) * | 1987-12-22 | 1989-11-14 | General Electric Company | Enhancing color stability of sterilizing radiation of polymer compositions |
| CA1272827A (en) * | 1984-10-10 | 1990-08-14 | James Leo Reilly | Compositions and methods using organosulfides for stabilization of polyolefins against photodegradation |
| US4774293A (en) * | 1985-06-26 | 1988-09-27 | Akzo N.V. | Process for cross-linking or degrading polymers and shaped articles obtained by this process |
| US5904717A (en) * | 1986-01-28 | 1999-05-18 | Thm Biomedical, Inc. | Method and device for reconstruction of articular cartilage |
| US4659762A (en) * | 1986-07-25 | 1987-04-21 | Ciba-Geigy Corporation | Tris (substituted hydroxyphenylthio) trithioorthoester stabilizers for polymers |
| US5013782A (en) * | 1988-04-22 | 1991-05-07 | Nippon Carbide Kogyo Kabushiki Kaisha | Flame retardant rigid or flexible chlorine-containing resin composition |
| US5081169A (en) * | 1989-10-31 | 1992-01-14 | Atochem North America, Inc. | Organic sulfide stabilized polymeric engineering resins |
| US5096947A (en) * | 1989-10-31 | 1992-03-17 | Atochem North America, Inc. | Organic peroxide and organic sulfide antioxidant composition |
| US5070124A (en) * | 1989-10-31 | 1991-12-03 | Atochem North America, Inc. | Sulfide antioxidants for stabilizing crosslinked polyolefins |
| CA2026183A1 (en) * | 1989-10-31 | 1991-05-01 | Joseph M. Bohen | Organic peroxides and organic sulfide antioxidant compositions |
| US5284886A (en) * | 1989-10-31 | 1994-02-08 | Elf Atochem North America, Inc. | Non-toxic polymeric compositions stabilized with organosulfide antioxidants |
| US5030679A (en) * | 1989-10-31 | 1991-07-09 | Atochem North America, Inc. | Organic sulfide antioxidants and polymers stabilized therewith |
-
1991
- 1991-07-24 US US07/735,140 patent/US5284886A/en not_active Expired - Lifetime
-
1992
- 1992-07-03 TW TW081105282A patent/TW221451B/zh active
- 1992-07-21 CA CA002074292A patent/CA2074292A1/en not_active Abandoned
- 1992-07-21 JP JP4214804A patent/JPH05194785A/ja not_active Withdrawn
- 1992-07-23 BR BR929202838A patent/BR9202838A/pt not_active Application Discontinuation
- 1992-07-24 EP EP92112679A patent/EP0525664A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| TW221451B (OSRAM) | 1994-03-01 |
| BR9202838A (pt) | 1993-03-23 |
| JPH05194785A (ja) | 1993-08-03 |
| US5284886A (en) | 1994-02-08 |
| EP0525664A1 (en) | 1993-02-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |