DE1694210C3 - - Google Patents
Info
- Publication number
- DE1694210C3 DE1694210C3 DE1694210A DE1694210A DE1694210C3 DE 1694210 C3 DE1694210 C3 DE 1694210C3 DE 1694210 A DE1694210 A DE 1694210A DE 1694210 A DE1694210 A DE 1694210A DE 1694210 C3 DE1694210 C3 DE 1694210C3
- Authority
- DE
- Germany
- Prior art keywords
- stabilizers
- phenol derivatives
- aging
- mixture
- polyolefins
- 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
- -1 hydrocarbon radical Chemical class 0.000 claims description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
- 150000002989 phenols Chemical class 0.000 claims description 9
- 239000003381 stabilizer Substances 0.000 claims description 8
- 230000003712 anti-aging effect Effects 0.000 claims description 7
- 239000003963 antioxidant agent Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 229920000098 polyolefin Polymers 0.000 claims description 5
- 229920006295 polythiol Polymers 0.000 claims description 5
- 230000000087 stabilizing effect Effects 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 3
- 239000004743 Polypropylene Substances 0.000 claims description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 229920001155 polypropylene Polymers 0.000 claims description 3
- 230000002195 synergetic effect Effects 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 230000015556 catabolic process Effects 0.000 claims 2
- MDLWEBWGXACWGE-UHFFFAOYSA-N octadecane Chemical group [CH2]CCCCCCCCCCCCCCCCC MDLWEBWGXACWGE-UHFFFAOYSA-N 0.000 claims 2
- 150000002898 organic sulfur compounds Chemical class 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 238000006731 degradation reaction Methods 0.000 claims 1
- MAHNFPMIPQKPPI-UHFFFAOYSA-N disulfur Chemical compound S=S MAHNFPMIPQKPPI-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 230000000704 physical effect Effects 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000007859 condensation product Chemical class 0.000 description 5
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
- 150000003464 sulfur compounds Chemical class 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
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- OILMLWAZYNVPMG-UHFFFAOYSA-N 4-methyl-2-nonylphenol Chemical compound CCCCCCCCCC1=CC(C)=CC=C1O OILMLWAZYNVPMG-UHFFFAOYSA-N 0.000 description 1
- CXNLJFNJBDGMEJ-UHFFFAOYSA-N C(C)(C)(C)C=1C(=CC(=C(C1)C(C)C(C)C1=C(C=C(C(=C1)C(C)(C)C)O)C)C)O Chemical compound C(C)(C)(C)C=1C(=CC(=C(C1)C(C)C(C)C1=C(C=C(C(=C1)C(C)(C)C)O)C)C)O CXNLJFNJBDGMEJ-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011116 polymethylpentene Substances 0.000 description 1
- 230000003244 pro-oxidative effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/372—Sulfides, e.g. R-(S)x-R'
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF28654A DE1265409B (de) | 1959-06-10 | 1959-06-10 | Verfahren zum Stabilisieren von Polyolefinen |
| DEF29113A DE1161688B (de) | 1959-06-10 | 1959-08-06 | Gegen Alterung stabilisierte Formmassen aus Polyolefinen |
| DEF0053846 | 1969-06-10 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1694210A1 DE1694210A1 (de) | 1971-04-22 |
| DE1694210B2 DE1694210B2 (de) | 1973-04-26 |
| DE1694210C3 true DE1694210C3 (enExample) | 1974-01-03 |
Family
ID=33101674
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF28654A Pending DE1265409B (de) | 1959-06-10 | 1959-06-10 | Verfahren zum Stabilisieren von Polyolefinen |
| DE19691694210 Granted DE1694210B2 (de) | 1959-06-10 | 1969-06-10 | Stabilisierung von polyolefinen |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF28654A Pending DE1265409B (de) | 1959-06-10 | 1959-06-10 | Verfahren zum Stabilisieren von Polyolefinen |
Country Status (1)
| Country | Link |
|---|---|
| DE (2) | DE1265409B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1272827A (en) * | 1984-10-10 | 1990-08-14 | James Leo Reilly | Compositions and methods using organosulfides for stabilization of polyolefins against photodegradation |
| US5340862A (en) * | 1988-10-07 | 1994-08-23 | Elf Atochem North America, Inc. | Stabilizers for halogen containing polymers |
| 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 |
| US5284886A (en) * | 1989-10-31 | 1994-02-08 | Elf Atochem North America, Inc. | Non-toxic polymeric compositions stabilized with organosulfide antioxidants |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA608334A (en) * | 1956-11-29 | 1960-11-08 | Western Electric Company, Incorporated | Stabilized straight chain hydrocarbons |
| AT203209B (de) * | 1956-11-29 | 1959-05-11 | Western Electric Co | Stabilisierte Mischung |
| AT203211B (de) * | 1956-11-29 | 1959-05-11 | Western Electric Co | Stabilisierte Mischung |
-
1959
- 1959-06-10 DE DEF28654A patent/DE1265409B/de active Pending
-
1969
- 1969-06-10 DE DE19691694210 patent/DE1694210B2/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE1694210B2 (de) | 1973-04-26 |
| DE1694210A1 (de) | 1971-04-22 |
| DE1265409B (de) | 1968-04-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |