Triazinanes and methods of making them
The present invention is directed to compounds represented by the formula: 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; and wherein M comprises a monovalent metallic cation such as sodium, lithium, or potassium; or a multivalent metallic cation such as zinc, nickel, iron, titanium, or cobalt; or an ammonium or alkyl ammonium cation derived by addition of proton (s) to a nitrogenous base.
1. A compound represented by formula I:
wherein R 1 is a hydrogen atom or an alkyl group having from 1 to 2 carbon atoms;
wherein R 2 is an alkylene group having from 1 to 12 carbon atoms, an arylene group having from 5 to 18 carbon atoms, or a heterocyclic group having from 5 to 12 carbon atoms; and
wherein M is a monovalent metallic cation; a multivalent metallic cation; or an ammonium or alkyl ammonium cation derived by addition of one or more protons to a nitrogenous base.
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 M is a monovalent metallic cation.
3. The compound of claim 1 , wherein R 1 is hydrogen;
wherein R 2 is an alkylene group having from 1 to 3 carbon atoms; and
wherein M is a monovalent metallic cation or an ammonium or alkyl ammonium cation derived by addition of one or more protons to a nitrogenous base.
4. Sodium S,S′,S″- ((1,3,5-triazinane-1,3,5-triyl)tris(ethane-2,1-diyl)) tris(sulfurothioate).
5. Sodium S,S′,S″- ((1,3,5-triazinane-1,3,5-triyl)tris(propane-3,1-diyl)) tris(sulfurothioate).
6. Sodium S,S′,S″- ((1,3,5-triazinane-1,3,5-triyl)tris(butane-4,1-diyl)) tris(sulfurothioate).
7. Sodium S,S′,S″- ((1,3,5-triazinane-1,3,5-triyl)tris(pentane-5,1-diyl)) tris(sulfurothioate).
8. A method of making the compound of claim 1 , comprising:
reacting a haloalkylamine hydrohalide with a metal thiosulfate to obtain an alkylammonium halide thiosulfate metal salt;
deprotonating the alkylammonium halide thiosulfate metal salt to obtain an alkylammonium thiosulfate metal salt; and
reacting the alkylammonium thiosulfate metal salt with an aldehyde to obtain the compound of claim 1 .
9. The method of claim 8 , wherein the haloalkylamine hydrohalide comprises 3-chloropropyl amine hydrochloride, the metal thiosulfate comprises sodium thiosulfate, and the aldehyde comprises formaldehyde.
10. An adhesion-promoting composition comprising the compound of claim 1 and optionally a carrier for said compound.
11. A stabilizer composition comprising the compound of claim 1 and optionally a carrier for said compound.
12. A vulcanizable elastomeric formulation comprising an elastomer and the compound of claim 1 .
13. The formulation of claim 12 wherein the compound is present in an amount of from 0.01 to 30 parts per 100 parts of elastomer by weight.
14. The formulation of claim 12 wherein the compound is present in an amount of from 0.1 to 5.0 parts per 100 parts of elastomer by weight.
15. A vulcanized elastomeric article formed from the vulcanizable elastomeric formulation of claim 12 .
16. The vulcanized elastomeric article of claim 15 wherein said vulcanized elastomeric article is a vehicle tire.
17. The vulcanized elastomeric article of claim 15 , wherein said vulcanized elastomeric article is a sidewall.
18. A combustible fuel composition comprising a combustible fuel and the compound of claim 1 .
19. A fuel additive composition comprising a fuel additive and the compound of claim 1 .
20. A wire-reinforced rubber component formed from the vulcanizable elastomeric formulation of claim 12 .