POLYOLS AND THEIR USE IN HYDROCARBON LUBRICATING AND DRILLING FLUIDS

• US 20120202723A1
• Filed: 02/03/2012
• Published: 08/09/2012
• Est. Priority Date: 02/04/2011
• Status: Abandoned Application

• Current Assignee: Lord Corporation (Parker-Hannifin Corporation)
• Original Assignee: Lord Corporation (Parker-Hannifin Corporation)
• Inventors: Abbey, Kirk J., Barber, Daniel E.
• Application Number:
  US13/365,776
• Publication Number:
  US 20120202723A1
• Time in Patent Office: Days
• US Class Current: 508/262
• CPC Class Codes: C07C 29/34 by condensation involving hydroxy groups or the mineral ester groups derived therefrom, e.g. Guerbet reaction
• CPC Class Codes: C07C 31/18 Polyhydroxylic acyclic alcohols
• CPC Class Codes: C09D 7/48 Stabilisers against degradation by oxygen, light or heat
• CPC Class Codes: C09K 2208/34 Lubricant additives
• CPC Class Codes: C09K 8/34 Organic liquids
• CPC Class Codes: C10M 105/14 polyhydroxy
• CPC Class Codes: C10M 2203/1006 used as base material
• CPC Class Codes: C10M 2205/0285 used as base material
• CPC Class Codes: C10M 2207/022 containing at least two hydroxy groups
• CPC Class Codes: C10M 2207/0225 used as base material
• CPC Class Codes: C10M 2209/1033 used as base material
• CPC Class Codes: C10M 2209/1085 used as base material
• CPC Class Codes: C10M 2223/045 Metal containing thio derivatives
• CPC Class Codes: C10N 2010/04 Groups 2 or 12
• CPC Class Codes: C10N 2030/06 Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
• CPC Class Codes: C10N 2030/08 Resistance to extreme temperature
• CPC Class Codes: C10N 2030/68 Shear stability
• CPC Class Codes: C10N 2040/08 Hydraulic fluids, e.g. brake-fluids
• CPC Class Codes: C10N 2050/02 dissolved or suspended in a carrier which subsequently evaporates to leave a lubricant coating
• CPC Class Codes: C10N 2050/10 Semi-solids; greasy
• CPC Class Codes: C10N 2070/00 : Specific manufacturing methods for lubricant compositions
• CPC Class Codes: H01F 1/447 : characterised by magnetoviscosity, e.g. magnetorheological, magnetothixotropic, magnetodilatant liquids electrorheological fluids C10M171/001

Abstract

Polyhydroxyl functional compounds that contain an all hydrocarbon backbone, wherein all of the hydroxyl groups are bonded to a primary carbon atom, are prepared through the reaction of an alpha, omega-terminal diol having a total of from about 6 to about 42 carbon atoms terminated with a mono-ol having a total of from about 4 to about 42 carbon atoms. The polyols can be used as additives in hydrocarbon oils, drilling fluids, industrial and automotive lubricating fluids, dispersants, engine lubricants, greases, coatings, adhesives, and also in magnetorheological fluids to improve various properties such as dispersion, wear protection, reduction of friction, high temperature stability, and improved aging.

Claims

1. A polyol composition comprising:

the reactant of a mono-ol with a diol;

wherein said mono-ol, independently, comprises

a compound having the formula R—

CH₂—

CH₂—

OH wherein R is a linear alkyl, branched alkyl, cyclic alkyl, or heterocyclic alkyl, or any combination thereof;

or

a compound having the formula Ar—

CH₂—

OH wherein Ar is a phenyl, pyridyl, furanyl, m- or p-alkylphenyl, or any other meta or para substituents compatible with the reaction conditions of said mono-ol with said diol;

or

a compound having the formula Ar′

-Q-CH₂—

CH₂—

OH where Q is —

(CR′

₂)—

_n, wherein n is from 1 to about 10, each R′

, independently, is H or R as defined above, and wherein Ar′

is phenyl, pyridyl, furanyl, o-, m-, p-alkylphenyl, o-, m-, or p-phenoxyphenyl, or any other ortho, meta, para substituents compatible with the reaction conditions of the mono-ol with said diol;

wherein said diol, independently, comprises

a compound having the formula R—

(CH₂—

CH₂—

OH)₂ wherein R is a linear alkyl, branched alkyl, cyclic alkyl, or heterocyclic alkyl, or any combination thereof;

or

a compound having the formula Ar(CH₂—

OH)₂ wherein Ar is m-phenyl, m- or m′

- or p- or p′

-diphenyl ether, or m- or m′

or p- or p′

-diphenylmethane, or any other ortho, meta, or para substituents compatible with the reaction conditions of said mono-ol with said diol;

or

a compound having the formula Ar′

(-Q-(CH₂)_k—

CH₂—

OH)₂ where each Q, independently, is —

(CR″

₂)—

_n, where each n, independently, is 0 or 1 to about 10 and each R″

, independently, can be H or R as defined hereinabove, where each k, independently, is 0 or 1, and wherein Ar′

can be a, o-, m-, or p-alkylphenyl, o-, m-, or p-phenoxyphenyl, or any other ortho, meta, or para substituents compatible with the reaction conditions of said mono-ol with said diol; and

wherein said R′

, Ar, and Ar′

of said different diol formulas can, independently, be the same or different, than said R, Ar, and Ar′

of said mono-ol.

3. The polyol composition of claim 1, containing beta branching and wherein said mono-ol comprises said compound having the formula R—

CH₂—

CH₂—

OH wherein R is a linear alkyl, and

wherein said diol comprises a compound having the formula R—

(CH₂—

CH₂—

OH)₂ wherein R is a branched alkyl having from about 2 to about 38 carbon atoms, or

wherein said diol comprises a mixture of R being branched alkyl and linear alkyl and the linear alkyl has from about 2 to about 10 carbon atoms.

4. The polyol composition of claim 3, wherein said branched alkyl diol has from about 28 to about 36 carbon atoms and the linear alkyl, if used, has 6 to about 8 carbon atoms.

5. The polyol composition of claim 1, comprising a compound having the formula:

6. The polyol composition of claim 5, wherein a is from 4 to about 21 carbon atoms, and wherein b is 10 to about 36 carbon atoms.

7. The polyol composition of claim 1, comprising a polyol compound having the formula

8. A magnetorheological fluid comprising the polyol composition of claim 1.

9. A magnetorheological fluid comprising the polyol composition of claim 3, wherein the magnetorheological fluid further comprises at least one or more of the following:

a carrier fluid, a antifriction agent, an antiwear agent, an extreme pressure agent, an anti-oxidant agent, or a viscosity modifier.

10. A magnetorheological fluid comprising the polyol composition of claim 3, wherein the magnetorheological fluid further comprises an organomolybdenum compound, or an organothiophosphorous compound, or a combination thereof.

11. A drilling fluid comprising the polyol composition of claim 1.

12. A drilling fluid comprising the polyol composition of claim 3.

13. A lubricating fluid comprising the polyol composition of claim 1.

14. A lubrication fluid comprising the polyol composition of claim 3.

15. An adhesive comprising the polyol composition of claim 1.

16. A coating comprising the polyol composition of claim 1.

17. A grease composition comprising the polyol composition of claim 1.

18. The polyol composition of claim 1:

wherein said mono-ol comprises a compound having the formula

19. The polyol composition of claim 1, wherein said mono-ol comprises (2-hydroxyethyl)cyclohexane, N-(6-hydroxyhexyl)piperidine, 3-phenylpropanol, 4-phenylbutanol, 4-(3-hydroxypropyl-pyridine, 3-(4-hydroxybutyl)furan, and any combination thereof.

20. The polyol composition of claim 1 wherein said polyol comprises a compound having the formula

21. The polyol composition of claim 1, wherein said polyol comprises a compound having the formula

22. An engine lubricating fluid comprising the polyol composition of claim 20, wherein the mole ratio of said one or more diols to said one or more mono-ols is from about 0.5 to about 2.0.

23. The polyol composition of claim 22, wherein said mono-ol is a branched mono-ol.

24. The polyol composition of claim 22, including zinc dialkyldithiophosphate.

25. The polyol composition of claim 24, including a base oil comprising natural fatty oils, mineral oils, polyphenylethers, dibasic acid esters, neopentylpolyol esters, phosphate esters, synthetic cycloparaffins and synthetic paraffins, synthetic unsaturated hydrocarbon oils, monobasic acid esters, glycol esters and ethers, silicate esters, silicone oils, silicone copolymers, synthetic hydrocarbons, poly-alpha-olefins derived from oligomerizing terminal alkenes such as 1-butene, 1-hexene, and the like, poly-alkylene-glycols such as oligomeric poly(propylene oxide), poly(butylenes oxide), and various alkylene oxide copolymers, naphthenic oils, diesel oils, and mixtures or blends thereof.

26. A friction reducing additive comprising the polyol composition of claim 20.

27. A drilling fluid additive comprising the polyol composition of claim 20, and wherein the mole ratio of said one or more diols to said one or more mono-ols is from about 1.5 to about 5.0.

2. A process for forming a polyol composition, comprising the steps of:

reacting a mono-ol with a diol in the presence of a basic catalyst;

wherein said mono-ol, independently, comprises

a compound having the formula R—

CH₂—

CH₂—

OH wherein R is a linear alkyl, branched alkyl, cyclic alkyl, or heterocyclic alkyl, or any combination thereof;

or

a compound having the formula Ar—

CH₂—

OH wherein Ar is a phenyl, pyridyl, furanyl, m- or p-alkylphenyl, or any other meta or para substituents compatible with the reaction conditions of said mono-ol with said diol; and

a compound having the formula Ar′

-Q-CH₂—

CH₂—

OH where Q is —

(CR′

₂)—

_n, wherein n is from 1 to about 10, each R′

, independently, is H or each R as defined above, and wherein Ar′

is phenyl, pyridyl, furanyl, o-, m-, p-alkylphenyl, o-, m-, or p-phenoxyphenyl, or any other ortho, meta, para substituents compatible with the reaction conditions of the mono-ol with said diol;

wherein said diol, independently, comprises;

a compound having the formula R—

(CH₂—

CH₂—

OH)₂ wherein R is a linear alkyl, branched alkyl, cyclic alkyl, or heterocyclic alkyl, or any combination thereof;

or

a compound having the formula Ar(CH₂—

OH)₂ wherein Ar is m-phenyl, m- or m′

- or p- or p′

-diphenyl ether, or m- or m′

or p- or p′

-diphenylmethane, or any other ortho, meta, or para substituents compatible with the reaction conditions;

or

a compound having the formula Ar′

(-Q-(CH₂)_k—

CH₂—

OH)₂ where each Q, independently, is —

(CR′

₂)_n—

, where each n, independently, is 0 or 1 to about 10 and each R″

, independently, can be H or R′

as defined hereinabove, where each k, independently, is 0 or 1, and wherein Ar′

can be a, o-, m-, or p-alkylphenyl, o-, m-, or p-phenoxyphenyl, or any other ortho, meta, or para substituents compatible with the reaction conditions, or

wherein R, Ar, and Ar′

of said diol can, independently, be the same or different than said R, Ar, and Ar′

of said mono-ol.