Triazinanes possessing thiosulfonate end-groups and methods of making them
The present invention is directed to compounds represented by the formula (I): wherein R 1 comprises a hydrogen atom or an alkyl group having 1 to 2 carbon atoms, wherein R 2 comprises an alkylene group, an arylene group, or a heterocyclic group. The three R 2 groups may be the same or different, wherein A comprises an alkyl, an aryl, or an alkylaryl group. The three A groups may be the same or different.
1 . A compound represented by formula I:
wherein R 1 is a hydrogen atom or an alkyl group having 1 to 2 carbon atoms;
wherein R 2 is an alkylene group, an arylene group, or a heterocyclic group, wherein the three R 2 groups may be the same or different; and
wherein A is an alkyl, an aryl, or an alkylaryl group, wherein the three A groups may be the same or different.
2 . The compound of claim 1 , wherein R 1 is a hydrogen atom; wherein R 2 is an alkylene group having from 1 to 5 carbon atoms; and wherein A is an alkyl, aryl or alkylaryl group having from 1 to 12 carbon atoms.
3 . The compound of claim 1 , wherein R 1 is a hydrogen atom; wherein R 2 is an alkylene group having from 2 to 4 carbon atoms; and wherein A is an alkyl, aryl or alkylaryl group having from 1 to 8 carbon atoms.
4 . S,S′,S″-((1,3,5-triazinane-1,3,5-triyl)tris(propane-3,1-diyl)) tris(4-methylbenzenesulfonothioate).
5 . S,S′,S″-((1,3,5-triazinane-1,3,5-triyl)tris(propane-3,1-diyl)) tribenzenesulfonothioate.
6 . S,S′,S″-((1,3,5-triazinane-1,3,5-triyl)tris(propane-3,1-diyl)) trimethanesulfonothioate.
7 . A method of making the compound of claim 1 , comprising:
reacting a sulfide salt having formula II:
SM 2 ,
wherein each M is independently an alkali metal cation, a proton cation, an ammonium cation, or an alkyl ammonium cation,
with an alkylarenesulfonyl halide having formula III:
wherein A is an alkylarene group and X is a halogen atom,
to form an alkylarenethiosulfonate salt having formula IV:
reacting the alkylarenethiosulfonate salt having formula IV with a haloalkylamine hydrohalide having formula V:
wherein R 2 is an alkylene group, an arylene group, or a heterocyclic group; and X is a halogen atom,
to obtain an S-(aminoalkyl) alkylarenethiosulfonate hydrohalide having formula VI:
deprotonating the S-(aminoalkyl) alkylarenethiosulfonate hydrohalide to obtain an S-(aminoalkyl) alkylarenethiosulfonate having formula VII:
reacting the S-(aminoalkyl) alkylarenethiosulfonate having formula VII with an aldehyde having formula VIII:
wherein R 1 is a hydrogen atom or an alkyl group having 1 to 2 carbon atoms,
to obtain the compound of claim 1 .
8 . The method of claim 7 , wherein the sulfide salt is sodium sulfide, the alkylarenesulfonyl halide is para-toluenesulfonyl chloride, the haloalkylamine hydrohalide is 3-chloropropylamine hydrochloride, and the aldehyde is formaldehyde.
9 . A stabilizer composition comprising the compound of claim 1 and optionally a carrier for said compound.
10 . A vulcanizable elastomeric formulation comprising an elastomer and the compound of claim 1 .
11 . The formulation of claim 10 wherein said the compound is present in an amount of from 0.01 to 30 parts per 100 parts of elastomer.
12 . The formulation of claim 11 wherein said the compound is present in an amount of from 0.1 to 5.0 parts per 100 parts of elastomer.
13 . A vulcanized elastomeric article formed from the vulcanizable elastomeric formulation of claim 10 .
14 . The vulcanized elastomeric article of claim 13 wherein said vulcanized elastomeric article is a component of a vehicle tire.
15 . The vulcanized elastomeric article of claim 14 wherein said component is a sidewall.
16 . A combustible fuel composition comprising a combustible fuel and the compound of claim 1 .
17 . A fuel additive composition comprising a fuel additive and the compound of claim 1 .