CN1919904A - 丁二烯类聚合物的抗氧剂的制备方法与用途 - Google Patents
丁二烯类聚合物的抗氧剂的制备方法与用途 Download PDFInfo
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- CN1919904A CN1919904A CN 200610086145 CN200610086145A CN1919904A CN 1919904 A CN1919904 A CN 1919904A CN 200610086145 CN200610086145 CN 200610086145 CN 200610086145 A CN200610086145 A CN 200610086145A CN 1919904 A CN1919904 A CN 1919904A
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 18
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- 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 claims description 12
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 12
- BGRKGHSKCFAPCL-UHFFFAOYSA-N 2-(2-methylbutan-2-yl)phenol Chemical class CCC(C)(C)C1=CC=CC=C1O BGRKGHSKCFAPCL-UHFFFAOYSA-N 0.000 claims description 11
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 11
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 9
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 9
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 claims description 8
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 6
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- 229920000181 Ethylene propylene rubber Polymers 0.000 claims description 4
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- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 claims description 4
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- GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 claims description 2
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 claims description 2
- YFHKLSPMRRWLKI-UHFFFAOYSA-N 2-tert-butyl-4-(3-tert-butyl-4-hydroxy-5-methylphenyl)sulfanyl-6-methylphenol Chemical compound CC(C)(C)C1=C(O)C(C)=CC(SC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 YFHKLSPMRRWLKI-UHFFFAOYSA-N 0.000 claims description 2
- MQWCQFCZUNBTCM-UHFFFAOYSA-N 2-tert-butyl-6-(3-tert-butyl-2-hydroxy-5-methylphenyl)sulfanyl-4-methylphenol Chemical compound CC(C)(C)C1=CC(C)=CC(SC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O MQWCQFCZUNBTCM-UHFFFAOYSA-N 0.000 claims description 2
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- MGMXGCZJYUCMGY-UHFFFAOYSA-N tris(4-nonylphenyl) phosphite Chemical compound C1=CC(CCCCCCCCC)=CC=C1OP(OC=1C=CC(CCCCCCCCC)=CC=1)OC1=CC=C(CCCCCCCCC)C=C1 MGMXGCZJYUCMGY-UHFFFAOYSA-N 0.000 description 10
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- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 2
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- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- 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
- WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
实施例 | 比较例 | ||
1#/min2#/min3#/min4#/min | 127.9125.6124.3126.5 | 比较1#/min比较2#/min比较3#/min比较4#/min | 25.646.955.095.7 |
5#/min6#/min7#/min8#/min9#/min10#/min11#/min12#/min13#/min14#/min15#/min16#/min | 113.6116.8119.0105.2128.6126.3116.3110.5102.1100.6109.7117.0 |
实施例 | 比较例 | ||
1#/hr2#/hr3#/hr4#/hr5#/hr6#/hr7#/hr8#/hr9#/hr10#/hr11#/hr12#/hr13#/hr14#/hr15#/hr16#/hr | 48464648414242415249404239394043 | 比较1#/hr比较2#/hr比较3#/hr比较4#/hr | 13222733 |
试样编号 | 24hr | 72hr | 120hr | 168hr | 240hr | 360hr | 500hr |
实施例1#/ΔE实施例3#/ΔE实施例5#/ΔE实施例7#/ΔE实施例9#/ΔE实施例10#/ΔE比较例1#/ΔE | 1.050.980.951.170.930.991.10 | 2.042.101.832.111.902.132.86 | 2.162.212.032.572.012.183.57 | 2.592.662.382.632.442.664.00 | 3.214.023.053.713.103.516.05 | 4.316.514.165.094.074.608.76 | 7.299.237.138.566.897.1618.4 |
实施例 | 初始门尼黏度 | 老化后门尼黏度 | 比较例 | 初始门尼黏度 | 老化后门尼黏度 |
1#2#3#4#5#6#7#8#9#10#11#12#13#14#15#16# | 43.043.544.043.544.042.842.543.242.643.143.042.643.542.143.539.8 | 45.847.046.649.346.545.346.849.944.945.649.348.749.549.848.445.7 | 比较1#比较2#比较3#比较4# | 43.343.544.043.9 | 65.560.138.668.3 |
实施例 | 初始凝胶% | 老化后凝胶% | 比较例 | 初始凝胶% | 老化后凝胶% |
1#3#5#7#11#12# | 0.030.030.050.040.050.04 | 35.3416.7417.7639.5738.1635.81 | 比较1# | 0.04 | 60.67 |
试样编号 | 外观颜色变化情况 | 热氧老化160小时拉伸强度变化情况 | 变化率 | |
实施例1#实施例3#实施例9#实施例10#实施例11#实施例12#比较例1#比较例2#比较例3# | 165小时变黄160小时变黄170小时变黄165小时变黄155小时变黄155小时变黄120小时变黄130小时变黄145小时变黄 | 初始值/Mpa 27.6初始值/Mpa 26.3初始值/Mpa 27.0初始值/Mpa 28.5初始值/Mpa 26.9初始值/Mpa 27.4初始值/Mpa 18.5初始值/Mpa 27.5初始值/Mpa 26.9 | 老化后//Mpa 12.6老化后//Mpa 11.6老化后//Mpa 12.5老化后//Mpa 13.1老化后//Mpa 11.7老化后//Mpa 12.3老化后//Mpa 2.1老化后//Mpa 9.51老化后//Mpa 10.8 | -54.3%-56.0%-53.8%-54.0%-56.5%-55.1%-88.6%-65.4%-59.9% |
试样编号 | 24hr | 48hr | 72hr | 96hr | 120hr |
实施例1#/ΔE实施例3#/ΔE实施例9#/ΔE实施例10#/ΔE比较例1#/ΔE | 4.263.924.114.155.03 | 5.564.154.965.077.35 | 7.207.017.137.149.68 | 8.408.258.057.9310.52 | 9.149.069.339.0111.08 |
试样编号 | 老化时间0小时 | 老化时间200小时 | 冲击平均强度的变化率% |
实施例1#/kJ/m2实施例3#/kJ/m2实施例9#/kJ/m2;实施例10#/kJ/m2实施例11#/kJ/m2实施例12#/kJ/m2比较例1#/kJ/m2 | 13.9110.9313.5012.6711.0311.2512.13 | 12.709.7512.3911.719.9510.910.53 | -8.6-10.8-8.2-7.6-9.8-10.3-13.1 |
试样编号 | 氧化诱导期(分钟) |
实施例1#实施例2#实施例3#实施例4#实施例5#实施例6#实施例7#实施例8#实施例9#实施例10#实施例11#实施例12#实施例13#实施例14#实施例15#实施例16#比较例1# | 66.363.267.260.563.163.861.666.463.565.057.653.455.950.751.064.421.5 |
Claims (10)
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Cited By (6)
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CN101798405A (zh) * | 2010-03-12 | 2010-08-11 | 江苏工业学院 | 具有抗黄变效能的镍系聚丁二烯橡胶复合防老剂 |
CN102516618A (zh) * | 2011-11-24 | 2012-06-27 | 山西合成橡胶集团有限责任公司 | 硫磺调节型氯丁橡胶中的复配乳液稳定剂 |
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CN114058077A (zh) * | 2020-08-03 | 2022-02-18 | 中国石油化工股份有限公司 | Sbs热塑性弹性体及其制备方法和防老剂及其应用 |
CN114437406A (zh) * | 2020-11-06 | 2022-05-06 | 中国石油化工股份有限公司 | 复配型抗氧剂和丁二烯橡胶组合物及其应用 |
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ES2076501T3 (es) * | 1990-01-24 | 1995-11-01 | Ciba Geigy Ag | Emulsiones acuosas que contienen antioxidantes. |
US5164434A (en) * | 1990-11-30 | 1992-11-17 | Rohm And Haas Company | Thermal stabilizers |
KR20060128832A (ko) * | 2003-09-10 | 2006-12-14 | 시바 스폐셜티 케미칼스 홀딩 인코포레이티드 | 열적 산화에 대한 메틸메타크릴레이트-부타디엔-스티렌그라프트 공중합체의 안정화 |
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Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101798405A (zh) * | 2010-03-12 | 2010-08-11 | 江苏工业学院 | 具有抗黄变效能的镍系聚丁二烯橡胶复合防老剂 |
CN101798405B (zh) * | 2010-03-12 | 2012-07-04 | 江苏工业学院 | 具有抗黄变效能的镍系聚丁二烯橡胶复合防老剂 |
CN102516618A (zh) * | 2011-11-24 | 2012-06-27 | 山西合成橡胶集团有限责任公司 | 硫磺调节型氯丁橡胶中的复配乳液稳定剂 |
CN102516618B (zh) * | 2011-11-24 | 2014-06-11 | 山西合成橡胶集团有限责任公司 | 硫磺调节型氯丁橡胶中的复配乳液稳定剂 |
CN107793763A (zh) * | 2017-10-20 | 2018-03-13 | 佛山市三水铠潮材料科技有限公司 | 一种耐高温导热硅脂及其制备方法 |
CN107793763B (zh) * | 2017-10-20 | 2020-08-11 | 佛山市三水铠潮材料科技有限公司 | 一种耐高温导热硅脂及其制备方法 |
CN110041561A (zh) * | 2018-01-17 | 2019-07-23 | 中国石油化工股份有限公司 | 低顺式聚丁二烯橡胶及其制备方法和防老剂及其应用 |
CN114058077A (zh) * | 2020-08-03 | 2022-02-18 | 中国石油化工股份有限公司 | Sbs热塑性弹性体及其制备方法和防老剂及其应用 |
CN114058077B (zh) * | 2020-08-03 | 2023-10-13 | 中国石油化工股份有限公司 | Sbs热塑性弹性体及其制备方法和防老剂及其应用 |
CN114437406A (zh) * | 2020-11-06 | 2022-05-06 | 中国石油化工股份有限公司 | 复配型抗氧剂和丁二烯橡胶组合物及其应用 |
CN114437406B (zh) * | 2020-11-06 | 2024-06-04 | 中国石油化工股份有限公司 | 复配型抗氧剂和丁二烯橡胶组合物及其应用 |
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