SU1348339A1 - 3,3ъ-bis-(4-nitroso-6-phenyl-1,2,4-triazinon-5)disulfide as structuring agent for rubber stocks - Google Patents
3,3ъ-bis-(4-nitroso-6-phenyl-1,2,4-triazinon-5)disulfide as structuring agent for rubber stocks Download PDFInfo
- Publication number
- SU1348339A1 SU1348339A1 SU864043108A SU4043108A SU1348339A1 SU 1348339 A1 SU1348339 A1 SU 1348339A1 SU 864043108 A SU864043108 A SU 864043108A SU 4043108 A SU4043108 A SU 4043108A SU 1348339 A1 SU1348339 A1 SU 1348339A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- phenyl
- disulfide
- bis
- nitroso
- triazinon
- Prior art date
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- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 229920001971 elastomer Polymers 0.000 title claims abstract description 8
- 239000005060 rubber Substances 0.000 title claims abstract description 8
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 230000032683 aging Effects 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 239000011593 sulfur Substances 0.000 claims abstract description 3
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 claims description 7
- 150000004000 hexols Chemical class 0.000 claims description 7
- 239000011435 rock Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003920 1,2,4-triazines Chemical class 0.000 description 1
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940055764 triaz Drugs 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
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- Compositions Of Macromolecular Compounds (AREA)
Abstract
Изобретение относитс к гетероциклическим соединени м, в частности к 3,3 -бис-(4-нитроэо-6-фенил-1,2,4- -триазинон-5)дисульфиду (ДС), который вл етс структурирующим агентом дл резиновых смесей и позвол ет получить вулканизаты с высоким сопротивлением к тепловому старению.Цель изобретени - получение нового соединени с полезными свойствами. Получение ДС ведут из З-тио-4-нитрозо- -6-фенил-1,2,4-триазинона-5 в и раствора 1 KI. Смесь нагревают 2-3 ч при 60-70 С. Продукт выдел ют известными приемами. Вулканизаты, содержащие ДС, обладают преимуществом по сравнению с вулканизатами, содержащими серу. 2 табл. § сл СА: 4: 00 со со соThe invention relates to heterocyclic compounds, in particular to 3,3-bis- (4-nitroeo-6-phenyl-1,2,4-triazinone-5) disulfide (DS), which is a structuring agent for rubber compounds and allows to obtain vulcanizates with high resistance to heat aging. The purpose of the invention is to obtain a new compound with useful properties. Obtaining DS are from Z-thio-4-nitroso-6-phenyl-1,2,4-triazinone-5 and solution 1 KI. The mixture is heated for 2-3 hours at 60-70 ° C. The product is isolated by known methods. Vulcanizates containing DS have an advantage over vulcanizates containing sulfur. 2 tab. § SL CA: 4:00 am co stock
Description
Изобретение относитс к новым производным 1,2,4-триазинов, а имен но к 3,3 -бис-(4-нитрозо-6-фенил- -1,2,4-триазинон-5) дисульфиду формулыThe invention relates to novel derivatives of 1,2,4-triazines, and in particular to 3,3-bis- (4-nitroso-6-phenyl--1,2,4-triazinon-5) disulfide of the formula
н.с, /-s-зЛ ns, / -s-zl
вл ющемус структурирующим агентом дл резиновых смесей и позвол - юшему получать вулканиз ты с высоки сопротивлением к тепловому старениюas a structuring agent for rubber compounds and allowing to obtain vulcanized compounds with high resistance to heat aging
Цель изобретени - новое соединение , производное 1,2,А-триазина, обладающее иным спектром действи по срав)1ению со структурными aнaлoгa шThe purpose of the invention is a new compound, a derivative of 1,2, A-triazine, which has a different spectrum of action compared with the structural analogue of
Пример 1. 3 ,3 -бис-С -нит- роз о-6-фенил-1,2,4-триазинон-5)дисульфид .Example 1. 3, 3 -bis-C-nitrosis o-6-phenyl-1,2,4-triazinon-5) disulfide.
0,05 моль (11,7 г) 3-тио-А-нитро 3о-6-фенил-1,2,А-триазинона-5 раствор ют при перемешивании в 200 мл 2%-ного раствора ,затем при комнатной температуре и непрерывном перемешивании приливают 500 мл 0,1 к раствора I,, KI. Смесь нагревают в течение 2-3 ч при 60-70°С и непрерывном .черемеигпвании. Оставл ют на ьочь. Осадок отфильтровывают, промывают 100 мл 2%-ного раствора 100 мл воды. Суша т на воздухе. Очиску производ т переосаждением из ацетона водой, соотношение апетон : вода 1:3.0.05 mol (11.7 g) of 3-thio-A-nitro 3o-6-phenyl-1,2, A-triazinone-5 is dissolved with stirring in 200 ml of a 2% solution, then at room temperature and With continuous stirring, 500 ml of 0.1 ml are added to a solution of I ,, KI. The mixture is heated for 2–3 hours at 60–70 ° C and continuous. Leave for the night. The precipitate is filtered off, washed with 100 ml of 2% aqueous solution of 100 ml of water. Drying t in the air. The cleaning is performed by reprecipitation from acetone with water, the apeton: water ratio is 1: 3.
Физико-химические характеристики соедине1 и Physico-chemical characteristics of the compound1 and
9 N0 от о9 N0 from about
HsCey N- ,Н,HsCey N-, H,
-/-s-з-Л - / - ss-l
Мол. вес. 466,42, т.пл. 222-226°С (разл.) . ИК-спектр, см : 1410 (-N 0); 1680 (с О ); 1120, 1040,Mol weight. 466.42, mp. 222-226 ° C (decomp.). IR spectrum, cm: 1410 (-N 0); 1680 (with O); 1120, 1040,
1348339213483392
1000 - кол. триаз, кольца. ПМР 5 м.д. (DMCO-DJ; 7,27-7,78 (М, Аг) .1000 - count triaz, rings. PMR 5 ppm (DMCO-DJ; 7.27-7.78 (M, Ar).
Найдено,%: С 46,3; Н 2,13; N 24,1.Found,%: With 46.3; H 2.13; N 24.1.
igHioNgO S,. igHioNgO S ,.
Вычислено,%: С 46,36; Н 2,16; N 24,02.Calculated,%: With 46.36; H 2.16; N 24.02.
Испытани соединени I проводились по общеприн той методике в резиновой смеси следующего состава, мае.ч. на 100 мае.ч. каучука: каучук СКИ-3 100,Oj стеарин 2,0; оксид динка 5,0; техуглерод П-234 50,0.The tests of compound I were carried out according to the generally accepted method in a rubber mixture of the following composition, wt. on 100 ma.ch. rubber: rubber SKI-3 100, Oj stearin 2.0; dinka oxide 5.0; carbon black P-234 50.0.
Состав вулканизующей системы и результаты испытаний приведены в табл. 1 .The composition of the vulcanizing system and the test results are given in table. one .
Установлено, что предлагаемое соединение вл етс вулканизующим агентом в присутствии соединений, обладающих свойствами окислител , в качестве которых были использованы дибензтиазолилдисульфид (альтакс) и гексахлор-пара-ксилоЛ (гексол). Вулканизацию образцов проводили при 1431,5°С в течение ,5 мин.It is established that the proposed compound is a vulcanizing agent in the presence of compounds with oxidizing properties, in which dibenzthiazolyl disulfide (altax) and hexachloro-para-xyloL (hexol) were used. Vulcanization of the samples was carried out at 1431.5 ° C for 5 minutes.
Вулканизаты, содержащие 3,3 -бис- -(4-нитрозо-6-фенил-1,2,4-трназинон- -5)дисульфид, обладают существенным преимуществом по сравнению с вулка- низатами, содержащими серу (широко примен емы структурирующий агент) по сопротивлению тепловому старению: сохран ют в процессе старени высокие значени условной прочности при раст жении и относительного удлинени (см. табл . 2).Vulcanizates containing 3,3-bis- - (4-nitroso-6-phenyl-1,2,4-trnazinon-5) disulfide have a significant advantage over volcanic acid containing sulfur (widely used structuring agent). ) for heat aging resistance: during the aging process, high values of conditional tensile strength and relative elongation are maintained (see Table 2).
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU864043108A SU1348339A1 (en) | 1986-02-21 | 1986-02-21 | 3,3ъ-bis-(4-nitroso-6-phenyl-1,2,4-triazinon-5)disulfide as structuring agent for rubber stocks |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU864043108A SU1348339A1 (en) | 1986-02-21 | 1986-02-21 | 3,3ъ-bis-(4-nitroso-6-phenyl-1,2,4-triazinon-5)disulfide as structuring agent for rubber stocks |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1348339A1 true SU1348339A1 (en) | 1987-10-30 |
Family
ID=21228662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU864043108A SU1348339A1 (en) | 1986-02-21 | 1986-02-21 | 3,3ъ-bis-(4-nitroso-6-phenyl-1,2,4-triazinon-5)disulfide as structuring agent for rubber stocks |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU1348339A1 (en) |
-
1986
- 1986-02-21 SU SU864043108A patent/SU1348339A1/en active
Non-Patent Citations (1)
| Title |
|---|
| Справочник резинщика. М.: Хи- ми , 1971. Патент US № 4252944, кл. С 07 D 253/06, 1981. * |
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