Synergistic mixture

Patent metadata

Field	Value
Publication number	US-9315759-B2
Application number	US-66957608-A
Country	US
Kind code	B2
Filing date	Jul 10, 2008
Priority date	Jul 16, 2007
Publication date	Apr 19, 2016
Grant date	Apr 19, 2016

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 at least one of
(A1) a tetrahydrobenzoxazine of formula (IV)

wherein
R 9 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 14 moieties,
R 14 is a hydrogen atom or a C 1 - to C 4 -alkyl radical, and
R 10 , R 11 , R 12 , and R 13 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 14 moieties,
R 12 may also be a radical of formula (Y)

wherein
X is a hydrocarbon bridging member which comprises one or more isobutene units, or
R 12 may also be a radical of the formula (Z) or (Z′)

wherein R 17 and R 18 may be the same or different and are each hydrogen or a C 1 - to C 10 -alkyl radical,
and R 10 and R 11 or R 11 and R 12 or R 12 and R 13 may also form a second tetrahydrooxazine ring with the —O—CH 2 —NR 15 —CH 2 — substructure attached to the benzene ring, or R 10 and R 11 and R 12 and R 13 may also form a second and a third tetrahydrooxazine ring with the —O—CH 2 —NR 15 —CH 2 — and —O—CH 2 —NR 16 —CH 2 — substructures attached to the benzene ring,
R 15 and R 16 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 14 moieties,
with the proviso that at least one of R 9 , R 10 , R 11 , R 12 , R 13 , R 15 , and R 16 comprises from 4 to 3000 carbon atoms and the remaining substituents from the group of R 9 , R 10 , R 11 , R 12 , R 13 , R 15 and R 16 , when they are hydrocarbyl radicals, each comprise from 1 to 20 carbon atoms;
and
(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 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 attached to the benzene ring, or
R 20 and R 21 and R 22 and R 23 may also form a second and a third tetrahydrooxazine ring with the —O—CH 2 —NR 31 —CH 2 — and —O—CH 2 —NR 32 —CH 2 — substructures attached 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; and
(B) from 5 to 50 % by weight of at least one of tetrakis[methylene-2 -(C 4 - to C 30 -alkylthio)propionate]methane, and
a C 4 - to C 30 -alkylthiopropylamide,
where a sum of the two components (A) and (B) adds up to 100% by weight.

2. The mixture of claim 1 , comprising (A1).

3. The mixture of claim 1 , comprising (A2).

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 mixture of claim 1 .

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

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

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

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

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

11. The composition of claim 10 , wherein the fuel is a turbine or jet fuel.

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

13. 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 mixture of claim 1 .

14. A lubricant composition, comprising the mixture of claim 1 .

15. The mixture of claim 1 , wherein R 12 is a radical of formula (Y), and X is a hydrocarbon bridging member which consists of one or more isobutene units.

16. The composition of claim 10 , wherein a concentration of the mixture in the composition, relative to a total weight of organic components, is 0.0001 to 5 wt. %.

17. The mixture of claim 1 , wherein (A) is present in an amount of 65 to 95% by weight, and (B) is present in an amount of 10 to 35% by weight.

Assignees

• Lange Arno
• Posselt Dietmar
• Basf Se

Inventors

• Lange Arno
• Posselt Dietmar

Classifications

• C10M2219/082

  containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms · CPC title

• C10M2219/022

  of hydrocarbons, e.g. olefines · CPC title

• C10L1/1824

  mono-hydroxy · CPC title

• C10L1/143

  mixtures of organic macromolecular compounds with organic non-macromolecular compounds · CPC title

• C10M2219/086

  containing sulfur atoms bound to carbon atoms of six-membered aromatic rings · CPC title