JPS5899469A - 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 - Google Patents
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Info
- Publication number
- JPS5899469A JPS5899469A JP10069381A JP10069381A JPS5899469A JP S5899469 A JPS5899469 A JP S5899469A JP 10069381 A JP10069381 A JP 10069381A JP 10069381 A JP10069381 A JP 10069381A JP S5899469 A JPS5899469 A JP S5899469A
- Authority
- JP
- Japan
- Prior art keywords
- tetrazole
- derivative
- hydroxyphenyl
- mol
- tert
- 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 abstract description 17
- 229920000642 polymer Polymers 0.000 title claims abstract description 16
- 150000003536 tetrazoles Chemical class 0.000 title claims description 46
- 230000000087 stabilizing effect Effects 0.000 title claims description 3
- 238000000034 method Methods 0.000 abstract description 10
- 239000000243 solution Substances 0.000 abstract description 10
- 238000003756 stirring Methods 0.000 abstract description 10
- 239000012954 diazonium Substances 0.000 abstract description 9
- 150000001989 diazonium salts Chemical class 0.000 abstract description 9
- -1 methoxy, ethoxy Chemical group 0.000 abstract description 9
- 239000007864 aqueous solution Substances 0.000 abstract description 8
- 230000001476 alcoholic effect Effects 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 5
- 150000007857 hydrazones Chemical class 0.000 abstract description 4
- 238000002156 mixing Methods 0.000 abstract description 4
- 239000003960 organic solvent Substances 0.000 abstract description 4
- 150000007529 inorganic bases Chemical class 0.000 abstract description 3
- 150000007530 organic bases Chemical class 0.000 abstract description 3
- RGHHSNMVTDWUBI-UHFFFAOYSA-N para-hydroxybenzaldehyde Natural products OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000003712 anti-aging effect Effects 0.000 description 18
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 229920001971 elastomer Polymers 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 239000005060 rubber Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001448 anilines Chemical class 0.000 description 6
- 238000004898 kneading Methods 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Substances [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 5
- 229920000459 Nitrile rubber Polymers 0.000 description 4
- 239000005062 Polybutadiene Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- 239000002861 polymer material Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 244000043261 Hevea brasiliensis Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229920003052 natural elastomer Polymers 0.000 description 3
- 229920001194 natural rubber Polymers 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 229920003048 styrene butadiene rubber Polymers 0.000 description 3
- HRXZRAXKKNUKRF-UHFFFAOYSA-N 4-ethylaniline Chemical compound CCC1=CC=C(N)C=C1 HRXZRAXKKNUKRF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920000181 Ethylene propylene rubber Polymers 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- 239000013078 crystal Substances 0.000 description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 2
- 229920003049 isoprene rubber Polymers 0.000 description 2
- VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 2
- 150000007855 nitrilimines Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 239000005061 synthetic rubber Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000004073 vulcanization Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- OGIQUQKNJJTLSZ-UHFFFAOYSA-N 4-butylaniline Chemical compound CCCCC1=CC=C(N)C=C1 OGIQUQKNJJTLSZ-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- OAPDPORYXWQVJE-UHFFFAOYSA-N 4-propylaniline Chemical compound CCCC1=CC=C(N)C=C1 OAPDPORYXWQVJE-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- 101100027969 Caenorhabditis elegans old-1 gene Proteins 0.000 description 1
- 244000046038 Ehretia acuminata Species 0.000 description 1
- 235000009300 Ehretia acuminata Nutrition 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- 150000001412 amines Chemical class 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- 210000001520 comb Anatomy 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- 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
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 238000010094 polymer processing Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001226 reprecipitation Methods 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
- 239000013589 supplement 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10069381A JPS5899469A (ja) | 1981-06-30 | 1981-06-30 | 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 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10069381A JPS5899469A (ja) | 1981-06-30 | 1981-06-30 | 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5899469A true JPS5899469A (ja) | 1983-06-13 |
| JPS6353988B2 JPS6353988B2 (enrdf_load_stackoverflow) | 1988-10-26 |
Family
ID=14280801
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10069381A Granted JPS5899469A (ja) | 1981-06-30 | 1981-06-30 | 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 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5899469A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102013219785A1 (de) * | 2013-09-30 | 2015-04-02 | Evonik Industries Ag | Sonnenlicht-induzierte Vernetzung von ungesättigten Polyolefinen mit nicht aktivierten vinylischen Doppelbindungen |
-
1981
- 1981-06-30 JP JP10069381A patent/JPS5899469A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| CHEM. ABSTR. * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102013219785A1 (de) * | 2013-09-30 | 2015-04-02 | Evonik Industries Ag | Sonnenlicht-induzierte Vernetzung von ungesättigten Polyolefinen mit nicht aktivierten vinylischen Doppelbindungen |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6353988B2 (enrdf_load_stackoverflow) | 1988-10-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP3156394B1 (en) | Alkylidene aminoganidine and salt thereof, modifier composition, modified rubber for tire, rubber composition for tire, and tire | |
| JPH04275349A (ja) | ゴム加硫物 | |
| JP2001503792A (ja) | 可塑化されたポリマー組成物 | |
| JP5954504B1 (ja) | 変性ゴム及びその製造方法、ゴム組成物、並びにタイヤ | |
| 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 | |
| JP2005516095A (ja) | 改良されたニトリルポリマー加硫物およびその製造方法 | |
| CA2000934C (en) | Bis-benzotriazolyl compounds and polymeric materials stabilized therewith | |
| JPH0735500B2 (ja) | 接着剤組成物 | |
| JPS6225137A (ja) | ゴム組成物 | |
| JPH0468042A (ja) | ゴム組成物 | |
| CN115746288A (zh) | 一种端氨基低聚物亚胺的制备方法及其应用 | |
| JPH11310622A (ja) | 湿気硬化型ウレタン樹脂組成物及びコーティング材、シーリング材 | |
| JP4347437B2 (ja) | 瞬間接着剤組成物 | |
| 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 | |
| JPS59152951A (ja) | ポリエステル型ブロツク共重合体組成物 | |
| JPH0499762A (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 | |
| JPS61229884A (ja) | パラフエニレンジアミン誘導体及びその誘導体を含有してなるゴム状重合体組成物 | |
| US4847313A (en) | Gel prevention in polymers | |
| CA1121380A (en) | Hindered phenol hydrazones and compositions stabilized therewith | |
| JPH1180364A (ja) | ブテン−ジエンブロック共重合体及びそれを含むゴム組成物 | |
| JPS6147842B2 (enrdf_load_stackoverflow) | ||
| US1779375A (en) | Method of vulcanizing caoutchouc and the product derived therefrom | |
| JP2718065B2 (ja) | 新規なカップリング剤およびそれを用いる加硫ゴムの物性改良方法 | |
| JPH11293036A (ja) | ゴム用加硫剤およびそのゴム組成物 | |
| RU2114132C1 (ru) | Способ стабилизации термоэластопластов |