JPS5859962A - ３，５−ジ−アルキル−４−ヒドロキシベンズアルデヒドのアリルスルホニルヒドラゾン誘導体及びその誘導体を添加して成る高分子安定化組成物 - Google Patents
３，５−ジ−アルキル−４−ヒドロキシベンズアルデヒドのアリルスルホニルヒドラゾン誘導体及びその誘導体を添加して成る高分子安定化組成物Info
- Publication number
- JPS5859962A JPS5859962A JP10069281A JP10069281A JPS5859962A JP S5859962 A JPS5859962 A JP S5859962A JP 10069281 A JP10069281 A JP 10069281A JP 10069281 A JP10069281 A JP 10069281A JP S5859962 A JPS5859962 A JP S5859962A
- Authority
- JP
- Japan
- Prior art keywords
- hydroxybenzaldehyde
- hydrazone derivative
- dialkyl
- derivative
- rubber
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims description 14
- -1 Arylsulfonyl hydrazone derivative Chemical class 0.000 title description 6
- 229920000642 polymer Polymers 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract description 7
- 239000003960 organic solvent Substances 0.000 abstract description 6
- 230000002378 acidificating effect Effects 0.000 abstract description 5
- 239000003054 catalyst Substances 0.000 abstract description 5
- 150000001875 compounds Chemical class 0.000 abstract description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 239000003963 antioxidant agent Substances 0.000 abstract description 2
- 238000000605 extraction Methods 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- UYGBSRJODQHNLQ-UHFFFAOYSA-N 4-hydroxy-3,5-dimethylbenzaldehyde Chemical compound CC1=CC(C=O)=CC(C)=C1O UYGBSRJODQHNLQ-UHFFFAOYSA-N 0.000 abstract 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000003064 anti-oxidating effect Effects 0.000 abstract 1
- 230000003078 antioxidant effect Effects 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000007857 hydrazones Chemical class 0.000 description 27
- 230000003712 anti-aging effect Effects 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229920001971 elastomer Polymers 0.000 description 12
- 239000005060 rubber Substances 0.000 description 12
- 239000007788 liquid Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000005062 Polybutadiene Substances 0.000 description 5
- 238000004898 kneading Methods 0.000 description 5
- 229920002857 polybutadiene Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 244000043261 Hevea brasiliensis Species 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- 229920003052 natural elastomer Polymers 0.000 description 4
- 229920001194 natural rubber Polymers 0.000 description 4
- ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 238000001226 reprecipitation Methods 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 229920003051 synthetic elastomer Polymers 0.000 description 3
- 239000005061 synthetic rubber Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- 229920000459 Nitrile rubber Polymers 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000000944 Soxhlet extraction Methods 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- VJRITMATACIYAF-UHFFFAOYSA-N benzenesulfonohydrazide Chemical compound NNS(=O)(=O)C1=CC=CC=C1 VJRITMATACIYAF-UHFFFAOYSA-N 0.000 description 2
- 229960004217 benzyl alcohol Drugs 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical class [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 2
- 229920001084 poly(chloroprene) Polymers 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 1
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 1
- RLGAUDBLDWUXQH-UHFFFAOYSA-N C(C)(C)(C)C=1CC(C=O)(C=C(C=1)C(C)(C)C)O Chemical compound C(C)(C)(C)C=1CC(C=O)(C=C(C=1)C(C)(C)C)O RLGAUDBLDWUXQH-UHFFFAOYSA-N 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920000181 Ethylene propylene rubber Polymers 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 241000243251 Hydra Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 238000010094 polymer processing Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10069281A JPS5859962A (ja) | 1981-06-30 | 1981-06-30 | ３，５−ジ−アルキル−４−ヒドロキシベンズアルデヒドのアリルスルホニルヒドラゾン誘導体及びその誘導体を添加して成る高分子安定化組成物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10069281A JPS5859962A (ja) | 1981-06-30 | 1981-06-30 | ３，５−ジ−アルキル−４−ヒドロキシベンズアルデヒドのアリルスルホニルヒドラゾン誘導体及びその誘導体を添加して成る高分子安定化組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5859962A true JPS5859962A (ja) | 1983-04-09 |
| JPS6247179B2 JPS6247179B2 (enrdf_load_stackoverflow) | 1987-10-06 |
Family
ID=14280774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10069281A Granted JPS5859962A (ja) | 1981-06-30 | 1981-06-30 | ３，５−ジ−アルキル−４−ヒドロキシベンズアルデヒドのアリルスルホニルヒドラゾン誘導体及びその誘導体を添加して成る高分子安定化組成物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5859962A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0267186U (enrdf_load_stackoverflow) * | 1988-11-09 | 1990-05-21 |
-
1981
- 1981-06-30 JP JP10069281A patent/JPS5859962A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6247179B2 (enrdf_load_stackoverflow) | 1987-10-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US9493599B2 (en) | Modified polymer | |
| JP2009513806A5 (enrdf_load_stackoverflow) | ||
| EP3060552A1 (fr) | Compose 1,3-dipolaire portant une fonction imidazole | |
| WO1998044040A1 (en) | Rubber composition and pneumatic tires | |
| EP3713924B1 (fr) | Composé 1,3-dipolaire comportant un groupe époxyde | |
| FR3067029A1 (fr) | Benzoxazine boree utilisable pour la synthese de polybenzoxazine | |
| JPS63284239A (ja) | ヒドロキシ−ベンズイミダゾールオキシドにより変性したゴム組成物 | |
| EP0855998B1 (en) | Antioxidants containing phenol groups and aromatic amine groups | |
| JP2002293783A (ja) | 環状ポリスルフィド化合物の製造方法及びそれを含むゴム組成物 | |
| WO2019174360A1 (zh) | 抗氧化剂1076合成工艺 | |
| EP0480466B1 (en) | Siliconic U.V. stabilizers containing reactive groups | |
| JPH04218546A (ja) | エチレン系ポリマーの架橋可能な組成物及び架橋方法 | |
| EP2486022B1 (fr) | 1, 2, 4 - triazine utilisable comme accélérateur de vulcanisation et son procédé d'obtention | |
| JPS5859962A (ja) | ３，５−ジ−アルキル−４−ヒドロキシベンズアルデヒドのアリルスルホニルヒドラゾン誘導体及びその誘導体を添加して成る高分子安定化組成物 | |
| WO2018109396A1 (fr) | Compose 1,3-dipolaire portant une double liaison carbone-carbone conjuguée | |
| CN112041293B (zh) | 含不饱和双键化合物、使用了该化合物的氧吸收剂、以及树脂组合物 | |
| KR100618030B1 (ko) | 신발 겉창 표면개질용 고무 용액과 이를 이용한 신발 겉창제조방법 | |
| JP2854144B2 (ja) | 芳香族ジチオカルボン酸のスルフアイド誘導体、その製法及びこれより成る天然−及び合成ゴム用の架橋剤 | |
| US20210171669A1 (en) | Diene polymer modified by an epoxide group | |
| US11987671B2 (en) | Elastomer mix comprising PLLA and PDLA | |
| EP3898601B1 (fr) | Composé polysulfuré comme agent de reticulation | |
| US4006140A (en) | Morpholinothio oxamides | |
| US4420613A (en) | Dihydrobenzothiazine compounds and the preparation thereof | |
| US3940364A (en) | Naphthofuranylnaphthol stabilizers | |
| JPS5899469A (ja) | ２―置換フェニル―５―（３′，５′―ジ―アルキル―４′―ヒドロキシフェニル）テトラゾール誘導体及びその誘導体からなる高分子の老化防止剤 |