Phosphono paraffins

Patent metadata

Field	Value
Publication number	US-12084625-B2
Application number	US-202318130255-A
Country	US
Kind code	B2
Filing date	Apr 3, 2023
Priority date	Jan 11, 2017
Publication date	Sep 10, 2024
Grant date	Sep 10, 2024

Abstract

Aspects described herein generally relate to methods of making a phosphono paraffin comprising forming a reaction mixture by mixing a haloparaffin, a phosphite, and sodium iodide. Methods comprise heating the reaction mixture to form the phosphono paraffin. Aspects described herein further relate to a phosphono paraffin represented by formula (I):

wherein each instance of R 1 is independently —H or

wherein each instance of R 2 and R 3 is independently linear or branched C 1-20 alkyl, C 1-20 cycloalkyl, or aryl; the number of instances where R 1 is

of formula (I) is between about 2 and about 8; and n is an integer between 4 and 22.

First claim

What is claimed is:

1. A method of making a hydraulic fluid, comprising:
mixing components of a hydraulic fluid composition, wherein the components of the hydraulic fluid are comprised of:
a phosphono paraffin represented by formula (I):

wherein:
each instance of R 1 is independently —H or

each instance of R 2 and R 3 is independently C 1-20 alkyl, cycloalkyl of C 20 or less, or aryl;
n is an integer of 4 to 22; and
the number of instances where R 1 is

 of formula (I) is about 2 to about 8,

a phosphate,
an epoxide modifier, and
an additive.

2. The method of claim 1 , wherein the phosphono paraffin is selected from the group consisting of:

and combinations thereof, wherein each of R 1 and R 2 is independently C 1-20 alkyl, cycloalkyl of C 20 or less, or aryl.

3. The method of claim 1 , wherein the phosphate is selected from the group consisting of dibutyl phenyl phosphate, butyl diphenyl phosphate, tri-cresyl phosphate, and combinations thereof.

4. The method of claim 1 , wherein the epoxide modifier is 2-ethylhexyl 7-oxabicyclo[4.1.0] heptane-3-carboxylate.

5. The method of claim 1 , wherein the additive is selected from the group consisting of water, a phosphonate, an antioxidant, a mineral oil, a vegetable oil, a glycol, an ester, a silicone oil, an alkanol, an alkylated aromatic hydrocarbon, a polyalpholephin, a corrosion inhibitor, a siloxane, and combinations thereof.

6. The method of claim 1 , wherein the phosphono paraffin comprises about 50 w/v % to about 60 w/v % of the hydraulic fluid composition.

7. The method of claim 1 , wherein the hydraulic fluid composition comprises:
about 20 w/v % to about 30 w/v % dibutyl phenyl phosphate,
about 5 w/v % to about 10 w/v % butyl diphenyl phosphate, and
about 1 w/v % to about 5 w/v % tri-cresyl phosphate.

8. A method of making a hydraulic fluid, comprising:
mixing components of a hydraulic fluid composition, wherein the components of the hydraulic fluid are comprised of:
a phosphono paraffin represented by formula (II):

wherein:
each instance of R 1 is independently —H or

each instance of R 2 and R 3 is independently C 1-20 alkyl, cycloalkyl of C 20 or less, or aryl;
n is an integer of 4 to 22; and
the number of instances where R 1 is

 of formula (I) is about 2 to about 8,

a phosphonate,
an ester, and
an additive.

9. The method of claim 8 , wherein the phosphono paraffin is selected from the group consisting of:

and combinations thereof, wherein, each of R 1 and R 2 is independently C 1-5 alkyl, cycloalkyl of C 6 or less, or phenyl.

10. The method of claim 8 , wherein the phosphonate is an alkyl phosphonate.

11. The method of claim 10 , wherein the alkyl phosphonate is a monophosphonate represented by formula (III):

wherein each of R 17 , R 18 , and R 19 is independently C 1-20 alkyl, aryl, or C 1-20 alkylaryl.

12. The method of claim 8 , wherein the ester is selected from the group consisting of an organophosphate ester, a phthalate, an adipate, a phosphoric acid ester, a fatty acid, and combinations thereof.

13. The method of claim 12 , wherein the additive is selected from the group consisting of water, a phosphate, an antioxidant, a mineral oil, a vegetable oil, a glycol, an ester, a silicone oil, an alkanol, an alkylated aromatic hydrocarbon, a polyalpholephin, a corrosion inhibitor, a siloxane, and combinations thereof.

14. The method of claim 13 , wherein the phosophono paraffin comprises about 10 wt % to about 80 wt % of the hydraulic fluid composition.

15. The method of claim 14 , wherein the phosphonate comprises about 10 wt % to about 20 wt % of the hydraulic fluid composition.

16. A method of making a hydraulic fluid comprising:
mixing components of a hydraulic fluid composition, wherein the components of the hydraulic fluid are comprised of:
a phosphono paraffin represented by formula (IV):

wherein:
each instance of R 1 is independently —H or

each instance of R 2 and R 3 is independently C 1-20 alkyl, cycloalkyl of C 20 or less, or aryl;
n is an integer of 4 to 22; and
the number of instances where R 1 is

 of formula (I) is about 2 to about 8,

a siloxane, and
an additive.

17. The method of claim 16 , wherein the phosphono paraffin is selected from the group consisting of:

and combinations thereof wherein,
each of R 1 and R 2 is independently ethyl, isopropyl, butyl, or phenyl.

18. The method of claim 16 , wherein the siloxane is a polysilo

Assignees

• Boeing Co

Inventors

• Ballard Mathew John
• Casey Philip Stephen
• Holmes Susan Wan-Yi
• Way Cameron David

Classifications

• C10N2040/08

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

• C10N2030/12

  Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives · CPC title

• C10N2030/10

  Inhibition of oxidation, e.g. anti-oxidants · CPC title

• C10M2223/0603

  used as base material · CPC title

• C10M105/74 Primary

  containing phosphorus · CPC title