Use of tetrahydrobenzoxazines as stabilizers

Patent metadata

Field	Value
Publication number	US-9951204-B2
Application number	US-201514924255-A
Country	US
Kind code	B2
Filing date	Oct 27, 2015
Priority date	Jul 26, 2005
Publication date	Apr 24, 2018
Grant date	Apr 24, 2018

Abstract

The use of tetrahydrobenzoxazines I

where R 1 is a hydrocarbyl radical and R 2 , R 3 , R 4 and R 5 are each independently hydrogen atoms, hydroxyl groups or hydrocarbyl radicals, and where R 2 to R 5 may also form a second and a third tetrahydrooxazine ring, with the proviso that at least one of the substituents has from 4 to 3000 carbon atoms and the remaining substituents, when they are hydrocarbyl radicals, each have from 1 to 20 carbon atoms, as stabilizers for stabilizing inanimate organic material, especially turbine fuels, against the action of light, oxygen and heat.

First claim

What is claimed is:

1. An antioxidant for stabilizing mineral oil products and fuels against the action of light, oxygen and heat, comprising: a tetrahydrobenzoxazine of formula I:

wherein R 1 is a 2-aminoethyl-, a N-(2′-aminoethyl-)-2-aminoethyl-, a N′-(2″-aminoethyl-)-N-(2′-aminoethyl-)-2-aminoethyl-, a N″-(2′″-aminoethyl-)-N′-(2″-aminoethyl-)-N-(2′-aminoethyl-)-2-aminoethyl-, or a 3-dimethylaminopropyl-radical,
and
R 2 , R 3 , R 4 and R 5 are each independently a hydrogen atom, a hydroxyl group or a hydrocarbyl radical having from 1 to 3000 carbon atoms which may optionally be interrupted by one or more selected from the group consisting of O, S and NR 6 moieties,
wherein R 4 may optionally be a radical of formula Y

wherein R 1 , R 2 , R 3 and R 5 are each as defined above and X is a hydrocarbon bridging element which consists of one or more isobutene units or comprises one or more isobutene units, or wherein R 4 may optionally be a radical of the formula Z or Z′

wherein R 1 , R 2 , R 3 and R 5 are each as defined above and R 10 and R 11 are each independently hydrogen or a C 1 - to C 10 -alkyl radical,
and wherein R 2 and R 3 or R 3 and R 4 or R 4 and R 5 , together with the part-structure —O—CH 2 —NR 7 —CH 2 — attached to the benzene ring, may optionally form a second tetrahydrooxazine ring, or R 2 and R 3 and R 4 and R 5 , together with the part-structures —O—CH 2 —NR 7 —CH 2 — and —O—CH 2 —NR 8 —CH 2 — attached to the benzene ring, may optionally form a second and a third tetrahydrooxazine ring,
wherein R 7 and R 8 are each independently a hydrocarbyl radical having from 1 to 3000 carbon atoms and are interrupted by one or more heteroatoms selected from the group consisting of O, S and NR 6 moieties, with the proviso that at least one of R 2 , R 3 , R 4 , or R 5 is a polyisobutenyl radical having a number-average molecular weight M n of from 200 to 40,000.

2. The antioxidant according to claim 1 , in which the remaining substituents from the group of R 2 , R 3 , R 4 , R 5 which are not polyisobutenyl radicals having a number-average molecular weight M n of from 200 to 40,000 each independently is a hydrogen atom, a hydroxyl group or, when they are hydrocarbyl radicals, linear or branched C 1 - to C 4 -alkyl radicals.

3. The antioxidant according to claim 1 , wherein the remaining substituents from the group of R 2 , R 3 , R 4 , R 5 which are not polyisobutenyl radicals having a number-average molecular weight M n of from 200 to 40,000 each independently is a hydrogen atom, a methyl radicals and a tert-butyl radical.

4. The antioxidant according to claim 1 , wherein the remaining substituents from the group of R 2 , R 3 , R 4 , R 5 which are not polyisobutenyl radicals having a number-average molecular weight M n of from 500 to 15,000 each independently is a hydrogen atom, a hydroxyl group or a linear or branched C 1 - to C 4 -alkyl radical.

5. The antioxidant according to claim 1 , wherein the remaining substituents from the group of R 2 , R 3 , R 4 , R 5 which are not polyisobutenyl radicals having a number-average molecular weight M n of from 900 to 1,100 each independently is a hydrogen atom, a hydroxyl group or a linear or branched C 1 - to C 4 -alkyl radical.

6. The antioxidant according to claim 1 , wherein R 3 and R 4 or R 4 and R 5 , together with a part-structure —O—CH 2 —NR 7 —CH 2 — oxygen-attached via the substituent R 4 form a second tetrahydrooxazine ring.

7. A fuel composition comprising a fuel and at least one antioxidant of the formula I as defined in claim 1 .

8. The fuel composition according to claim 7 , wherein the fuel is selected from the group consisting of a diesel fuel, a gasoline fuel, and a turbine fuel.

9. The fuel composition according to claim 7 , further comprising at least one of a diluent and a Mannich adduct.

10. The fuel composition according to claim 9 , wherein the composition comprises a Mannich adduct and the Mannich adduct is the reaction product of polyisobutene-substituted phenols with formaldehyde and mono- or polyamines selected from the group of ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, and dimethylaminopropylamine.

11. An additive concentrate for fuels, comprising at least one antioxidant of formula I as defined in claim 1 and optionally at least one of a diluent and an additive.

12. The additive concentrate according to claim 11 , further comprising a Mannich adduct.

13. The additive concentrate according to claim 12 , wherein the Mannich adduct is the reaction product of polyisobutene-substituted phenols with formaldehyde and mono- or polyamines selected from the group of ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, and dimethylaminopropylamine.

14. The antioxidant according to claim 1 , wherein R 1 is a 3-dimethylaminopropyl-radical.

15. The antioxidant according to claim 1 , wherein
R 2 , R 3 and R 5 are each independently a hydrogen atom or a linear or branched C 1 to C 4 -alkyl radical, and
R 4 is a polyisobutenyl radical having a number-average molecular weight M n of from 200 to 40,000.

Assignees

• Basf Se

Inventors

• Lange Arno
• Mach Helmut
• Rath Hans Peter
• Posselt Dietmar

Classifications

• C10L1/238

  obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds {(C10L1/221 takes precedence)} · CPC title

• C10L1/221

  compounds of uncertain formula; reaction products where mixtures of compounds are obtained · CPC title

• C10L1/1832

  mono-hydroxy (C10L1/1802, C10L1/1805, C10L1/1808, C10L1/1811, C10L1/1814, C10L1/1817, C10L1/1828 take precedence) · CPC title

• C10L2250/04

  Additive or component is a polymer · CPC title

• C08K5/5333

  Esters of phosphonic acids · CPC title