Synergistic mixture

Patent metadata

Field	Value
Publication number	US-9670430-B2
Application number	US-201514962220-A
Country	US
Kind code	B2
Filing date	Dec 8, 2015
Priority date	Jul 16, 2007
Publication date	Jun 6, 2017
Grant date	Jun 6, 2017

Abstract

A synergistic mixture comprising from 1 to 99.9% by weight of compounds having structural elements (I)

in which the free valencies on the oxygen atom and on the nitrogen atom may be combined to form a five-, six- or seven-membered ring and the benzene ring may also bear substituents at one or more of the free positions, and from 0.1 to 99% by weight of sulfur-containing organic compounds with antioxidant action. This synergistic mixture is suitable as a stabilizer for stabilizing inanimate organic material, especially mineral oil products and fuels, against the action of light, oxygen and heat.

First claim

The invention claimed is:

1. A synergistic mixture, comprising:
(A) from 50 to 95% by weight of a compound having a structural element which is
(A2) a polycyclic phenolic compound comprising up to 20 benzene rings per molecule, obtained by reacting
(a2-i) a tetrahydrobenzoxazine of formula (XXVI)

wherein
substituent R 19 is a hydrocarbyl radical comprising from 1 to 3000 carbon atoms and may be interrupted by one or more heteroatoms from the group of O and S and/or by one or more NR 24 moieties,
R 24 is a hydrogen atom or a C 1 - to C 4 -alkyl radical, and
R 20 , R 21 , R 22 , and R 23 are each independently hydrogen atoms, hydroxyl groups, or hydrocarbyl radicals comprising in each case from 1 to 3000 carbon atoms and may be interrupted by one or more heteroatoms from the group of O and S and/or by one or more NR 24 moieties,
with at least one of
(a2-ii) one or more of the same or different phenols of formula (XXVII)

wherein
R 25 , R 26 , R 27 , and R 28 are each independently hydrogen atoms, hydroxyl groups, or hydrocarbyl radicals comprising in each case from 1 to 3000 carbon atoms and may be interrupted by one or more heteroatoms from the group of O and S and/or by one or more NR 24 moieties,
and
(a2-iii) one or more of the same or different tetrahydrobenzoxazines of formula (XXVI) wherein R 22 may also be a radical of the formula (Z″) and R 27 may also be a radical of the formula (Z′″)

wherein
R 25 may also be a radical derived from a tetrahydrobenzoxazine of formula (XXVI),
R 33 is hydrogen or a radical derived from a tetrahydrobenzoxazine of formula (XXVI), and
R 29 and R 30 may be the same or different and are each hydrogen or a C 1 - to C 10 -alkyl radical, and
R 20 and R 21 or R 21 and R 22 or R 22 and R 23 may also form a second tetrahydrooxazine ring with the —O—CH 2 —NR 31 —CH 2 — substructure attatched to the benzene ring, or
R 20 and R 21 and R 22 and R 23 may also form a second and third tetrahydrooxazine ring with the —O—CH 2 —NR 31 —CH 2 — and —O—CH 2 —NR 32 —CH 2 — substructures attetched to the benzene ring, where R 31 and R 32 are each independently hydrocarbyl radicals comprising in each case from 1 to 3000 carbon atoms and may be interrupted by one or more heteroatoms from the group of O and S and/or by one or more NR 24 moieties,
with the proviso that at least one of R 19 , R 20 , R 21 , R 22 , R 23 , R 25 , R 26 , R 27 , R 28 , R 31 , and R 32 comprises from 13 to 3000 carbon atoms and the remaining substituents from the group of R 19 , R 20 , R 21 , R 22 , R 23 , R 25 , R 26 , R 27 , R 28 , R 31 , and R 32 , when they are hydrocarbyl radicals, comprise in each case from 1 to 20 carbon atoms;
(B) from 5 to 50% by weight of at least one sulfur containing organic compound with antioxidant activity selected from the group consisting of 2-mercaptobenzthiazole, 2-mercaptobenzimidazole, mercaptotriazine, C4- to C30-alkanethiol, thio glycol, di-C4- to C30-alkyl sulfide, bis(aralkyl) sulfide, bis(aralkyl) disulfide, di-C4- to C30-alkyl disulfide, di(C4- to C30-alkyl) 3,3′-thiopropionate, tetrakis[methylene-2-(C4- to C30-alkylthio) propionate]methane, C4- to C30-alkylthiopropylamide, thiodiethylene bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate], 2,4-bis(C4- to C30-alkylthiomethyl)-6-methylphenol, hydroxyl-containing diaryl sulfide, zinc salt of dialkyldithiocarbamic acid, zinc dialkyldithiophosphate, and a reaction product of terpene, resin oil or low molecular weight polybutenes with sulfur or thiophenol,
(C) from 0.1 to 5% by weight of at least one sulfur free antioxidant that is a substituted phenol derivative, an arylamine, or a p-phenylenediamine,
where a sum of the concentrations of the three components (A), (B), and (C) adds up to 100% by weight.

2. The synergistic mixture according to claim 1 , wherein the at least one sulfur-free antioxidant is selected from the group consisting of 2,6-di-tert-butylphenol, 2,6-di-tert-butyl-3-methylphenol, 2,6-di-tert-butyl-4-methylphenol, methylene-4,4′-bis(2,6-di-tert-butylphenol), diphenylamine, phenyl-α-naphthylamine, 4,4′-tetramethyldiaminodiphenylmethane, and N,N′-di-sec-butyl-p-phenylenediamine.

3. The synergistic mixture according to claim 1 , wherein component (B) is selected from the group consisting of tetrakis[methylene-2-(C4- to C30-alkylthio)propionate]methane, C4- to C30-alkylthiopropylamide, hydroxyl-containing diaryl sulfide, and a reaction product of terpene, resin oil or low molecular weight polybutene with sulfur or thiophenol.

4. A method for stabilizing an inanimate organic material against the action at least one of light, oxygen, and heat, the method comprising:
combining the inanimate organic material with the synergistic mixture of claim 1 .

5. A mineral oil product or fuel, comprising the synergistic mixture of claim 1 .

6. A turbine or jet fuel, comprising the synergistic mixture of claim 1 .

7. A method of improving thermal stability of a turbine fuel, the method comprising combining the fuel with a stabilizer comprising the synergistic mixture of claim 1 .

8. A method of reducing deposits in a fuel system or combustion system of a turbine, the method comprising combusting a fuel comprising the synergistic mixture of claim 1 .

9. An inanimate organic material, comprising the synergistic mixture of claim 1 .

10. A fuel composition, comprising:
a fuel; and
the mixture of claim 1 .

11. An additive concentrate, comprising the synergistic mixture of claim 1 and at least one of a further diluent and a further additive.

12. A method for improving at least one of oxidation, aging, and shear stability of a lubricant composition, the method comprising:
combining the lubricant composition with the synergistic mixture of claim 1 .

13. A lubricant composition, comprising the synergistic mixture of claim 1 .

Assignees

• Basf Se

Inventors

• Lange Arno
• Posselt Dietmar

Classifications

• C10M2219/06

  Thio-acids; Thiocyanates; Derivatives thereof · CPC title

• C10L1/2475

  obtained otherwise than by reactions only involving unsaturated carbon to carbon bonds · CPC title

• C10M2219/083

  Dibenzyl sulfide · CPC title

• C10L2200/0263

  Sulphur containing compounds · CPC title

• C10M2219/09

  Heterocyclic compounds containing no sulfur, selenium or tellurium compounds in the ring · CPC title