Composition and method of forming the same

Patent metadata

Field	Value
Publication number	US-2016304801-A1
Application number	US-201415101704-A
Country	US
Kind code	A1
Filing date	Dec 4, 2014
Priority date	Dec 6, 2013
Publication date	Oct 20, 2016
Grant date	—

Abstract

A composition comprises the reaction product of a dithiophosphate derivative and an amine. The reaction product is present in the composition in an amount of at least about 25 wt. %. The composition may include additional components. A method of forming the composition comprises the step of combining the dithiophosphate derivative and the amine to form the composition. A method of increasing thermal stability of a dithiophosphate derivative comprises the step of combining the dithiophosphate derivative and an amine. The dithiophosphate derivative can decompose to form hydrogen sulfide (H2S). However, the amine substantially prevents thermal decomposition of the dithiophosphate derivative. An example of the dithiophosphate derivative is 3-(di-isobutoxy-thiophosphorylsulfanyl)-2-methyl-propanoic acid. An example of the amine is ditridecyl amine. The composition can be used for a variety of applications. For example, the composition can be used as an antiwear compound/additive in lubricants, metalworking fluids, hydraulic fluids, etc.

First claim

1 . A composition comprising:
the reaction product of;
a dithiophosphate derivative, and
an amine;
wherein the reaction product is present in an amount of at least about 25 wt. %.

2 . The composition as set forth in claim 1 , wherein the reaction product is present in an amount of at least about 50 wt. %.

3 . The composition as set forth in claim 1 , wherein the reaction product is present in an amount of at least about 75 wt. %.

4 . The composition as set forth in claim 1 , wherein said dithiophosphate derivative is of the following general formula:

and wherein R 1 and R 2 independently of one another are C 3 -C 18 alkyl, C 5 -C 12 cycloalkyl, C 5 -C 6 cycloalkylmethyl, C 9 -C 10 bicycloalkylmethyl, C 9 -C 10 tricycloalkylmethyl, phenyl, or C 7 -C 24 alkylphenyl, alternatively R 1 and R 2 together are (CH 3 ) 2 C(CH 2 ) 2 ; R 3 is hydrogen or methyl; and the sum of n+m is at least 1.

5 . The composition as set forth in claim 4 , wherein R 1 and R 2 independently of one another are C 3 -C 18 alkyl, C 5 -C 6 cycloalkyl, or C 7 -C 18 alkylphenyl.

6 . The composition as set forth in claim 4 , wherein R 3 is hydrogen and the sum of n+m is from 1 to 25.

7 . The composition as set forth in claim 1 , wherein said dithiophosphate derivative is β-dithiophosphorylated propionic acid.

8 . The composition as set forth in claim 1 , wherein said amine has a number average molecular weight (M n ) less than about 3,000.

9 . The composition as set forth in claim 1 , wherein said amine has a number average molecular weight (M n ) less than about 2,000.

10 . The composition as set forth in claim 1 , wherein said amine is an aliphatic or cycloaliphatic amine.

11 . The composition as set forth in claim 1 , wherein said amine is a secondary aliphatic amine.

12 . The composition as set forth in claim 1 , wherein said amine is ditridecyl amine.

13 . The composition as set forth in claim 1 , further comprising free dithiophosphate derivative.

14 . The composition as set forth in claim 1 , meeting Occupational Safety & Health Administration (OSHA) Standards for hydrogen sulfide (H 2 S) exposure.

15 . The composition as set forth in claim 1 as an antiwear additive.

16 . A method of forming the composition as set forth in claim 1 , said method comprising the step of combining the dithiophosphate derivative and the amine to form the composition.

17 . A method of increasing thermal stability of a dithiophosphate derivative that decomposes to form hydrogen sulfide (H 2 S), said method comprising the step of combining the dithiophosphate derivative and an amine, wherein the amine substantially prevents thermal decomposition of the dithiophosphate derivative.

18 . The method as set forth in claim 16 , wherein a decomposition temperature of the dithiophosphate derivative is at least about 60° C.

19 . The method as set forth in claim 16 , wherein after the step of combining, H 2 S exposure from the dithiophosphate derivative does not exceed 10 ppm (15 mg/m 3 ).

20 . The method as set forth in claim 17 , wherein:
i) the dithiophosphate derivative is of the following general formula:

and
wherein R 1 and R 2 independently of one another are C 3 -C 18 alkyl, C 5 -C 12 cycloalkyl, C 5 -C 6 cycloalkylmethyl, C 9 -C 10 bicycloalkylmethyl, C 9 -C 10 tricycloalkylmethyl, phenyl, or C 7 -C 24 alkylphenyl, alternatively R 1 and R 2 together are (CH 3 ) 2 C(CH 2 ) 2 ; R 3 is hydrogen or methyl; and the sum of n+m is at least 1;
ii) the amine is an aliphatic or cycloaliphatic amine having a number average molecular weight (Mn) less than about 3,000; or
iii) both i) and ii).

Assignees

• Basf Se

Inventors

• Hoey Michael Dennis
• Scanlon Eugene
• Mensah Frederick
• Brown Douglas S
• Jung Alfred Karl
• Seibel Shaun Robert
• Hasenhuetl Patrick Daniel
• Schmitt Ralf Lorenz

Classifications

• C07F9/06

  without P—C bonds · CPC title

• C10N2030/50

  Emission or smoke controlling properties · CPC title

• C10N2040/12

  Gas-turbines · CPC title

• C10M159/123 Primary

  obtained by phosphorus or phosphorus-containing compounds, e.g. P x S x with organic compounds · CPC title

• C10N2040/08

  Hydraulic fluids, e.g. brake-fluids · CPC title