JPS6239159B2 - - Google Patents
Info
- Publication number
- JPS6239159B2 JPS6239159B2 JP55017759A JP1775980A JPS6239159B2 JP S6239159 B2 JPS6239159 B2 JP S6239159B2 JP 55017759 A JP55017759 A JP 55017759A JP 1775980 A JP1775980 A JP 1775980A JP S6239159 B2 JPS6239159 B2 JP S6239159B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- grams
- group
- antioxidant
- compound represented
- 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
- 229910052698 phosphorus Inorganic materials 0.000 claims description 12
- 239000011574 phosphorus Substances 0.000 claims description 12
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 11
- 150000002989 phenols Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000006482 condensation reaction Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 150000002903 organophosphorus compounds Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000003963 antioxidant agent Substances 0.000 description 15
- 230000003078 antioxidant effect Effects 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229920000620 organic polymer Polymers 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000002530 phenolic antioxidant Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- -1 phosphorus compound Chemical class 0.000 description 2
- 150000003018 phosphorus compounds Chemical class 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 239000012209 synthetic fiber Substances 0.000 description 2
- 239000005061 synthetic rubber Substances 0.000 description 2
- OSOLHARQJQEMBZ-UHFFFAOYSA-N 1-chloropentylbenzene Chemical compound CCCCC(Cl)C1=CC=CC=C1 OSOLHARQJQEMBZ-UHFFFAOYSA-N 0.000 description 1
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical class OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 1
- WODZSHMAILHEGD-UHFFFAOYSA-N 6-tert-butyl-3-(chloromethyl)-2,4-dimethylphenol Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CCl WODZSHMAILHEGD-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000002656 Distearyl thiodipropionate Substances 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
- 235000019305 distearyl thiodipropionate Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229940087646 methanolamine Drugs 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1775980A JPS56115383A (en) | 1980-02-18 | 1980-02-18 | Antioxidant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1775980A JPS56115383A (en) | 1980-02-18 | 1980-02-18 | Antioxidant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56115383A JPS56115383A (en) | 1981-09-10 |
| JPS6239159B2 true JPS6239159B2 (de) | 1987-08-21 |
Family
ID=11952642
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1775980A Granted JPS56115383A (en) | 1980-02-18 | 1980-02-18 | Antioxidant |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56115383A (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19847137A1 (de) * | 1998-10-13 | 2000-04-20 | Schill & Seilacher | Verwendung von DOP als Antioxidations-, Alterungsschutz- und Arzneimittel |
| JP5342217B2 (ja) * | 2008-11-26 | 2013-11-13 | 日華化学株式会社 | 有機リン化合物の製造方法 |
| JP2020121961A (ja) * | 2019-01-31 | 2020-08-13 | Ｊｘｔｇエネルギー株式会社 | リン化合物の製造方法 |
-
1980
- 1980-02-18 JP JP1775980A patent/JPS56115383A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56115383A (en) | 1981-09-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IE45226B1 (en) | New tetracarboxylic acid tetrachlorides | |
| JPH01104027A (ja) | エーテル含有またはチオエーテル含有１，３−ジケトン、及び該化合物を含有する塩素含有ポリマー組成物 | |
| SU514569A3 (ru) | Способ получени производных пиридазина | |
| US4276232A (en) | Phosphorus stabilizers | |
| US3860598A (en) | Process for the production of benzylidene compounds | |
| JPH04507247A (ja) | ビス環状ホスファイト化合物並びにそれらで安定化されたポリマー材料 | |
| JPH0288655A (ja) | 塩素含有ポリマー用安定剤としてのチオウラシル | |
| JPS61165397A (ja) | ペンタエリスリトールジホスフイツト類、その製造方法及びその安定化剤としての使用 | |
| JP2924357B2 (ja) | 亜リン酸エステル化合物、その製法および用途 | |
| US3778446A (en) | 2-substituted-4,5-dicyanoimidazoles and their preparation from diaminomaleonitrile | |
| US3268582A (en) | Phenylalkyl-carboxylic acid amides | |
| ATE54153T1 (de) | Androstan-17beta-carbonsaeureester, ein prozess und zwischenprodukte fuer ihre herstellung, kompositionen und methode zur behandlung inflammatorischer zustaende. | |
| JPS6239159B2 (de) | ||
| US2702825A (en) | Alkyl polychlorobenzyl ethers | |
| US4038327A (en) | 3,5-disubstituted-4-hydroxybenzyl derivative | |
| US2611787A (en) | Fluorocarbon ortho esters | |
| JPS6245894B2 (de) | ||
| EP0335262B1 (de) | Phosphit-Verbindungen | |
| JPH07103113B2 (ja) | 新規トリアゾール誘導体及び該化合物からなる有機ポリマー用安定剤 | |
| US4055599A (en) | N-(Alkylhydrobenzyl)-alkylthio- and mercapto-acetamides | |
| US3317573A (en) | Heterocyclic organotin compounds | |
| DE69216611T2 (de) | Organische borreagenzien für die herstellung von propargylalkohole | |
| US3122548A (en) | S-phenethyloxy carbonyl thiamine o-monophophosphate and the hydrochloride thereof | |
| JPS62108867A (ja) | イミダゾリル−メタン誘導体の製造方法 | |
| JPS59172462A (ja) | 硫黄含有アルキリデン―ビスクエノールの製造方法 |