# US 10,308,891 B2 · Hydraulic fluid compositions

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- Number: US 10,308,891 B2
- Document ID: US10308891B2
- Status: Granted
- Kind: B2
- Application number: 14/914,225
- Filed: 2014-08-13
- Published: 2016-07-21
- Granted: 2019-06-04
- Earliest claimed: 2013-08-31
- Assignees: Houghton Technical Corp.
- Applicants: Houghton Technical Corp.
- Inventors: Douglas C. Caskey, Jr.; Kenneth R. Cavanaugh
- Web page: https://patentgrep.com/patent/US10308891B2

## CPC

- C10M 169/04: Mixtures of base-materials and additives
- C09K 8/03: Specific additives for general use in well-drilling compositions
- C10M 103/00: Lubricating compositions characterised by the base-material being an inorganic material (containing more than 10% water C10M173/00)
- C10M 129/08: containing at least 2 hydroxy groups
- C10M 129/26: Carboxylic acids; Salts thereof
- C10M 133/08: containing hydroxy groups
- C10M 133/44: Five-membered ring containing nitrogen and carbon only
- C10M 135/02: Sulfurised compounds
- C10M 137/04: Phosphate esters
- C10M 137/12: having a phosphorus-to-carbon bond
- C10M 173/02: not containing mineral or fatty oils
- E21B 7/00: Special methods or apparatus for drilling
- E21B 7/12: Underwater drilling (using heave compensators E21B19/09)
- C10M 2207/022: containing at least two hydroxy groups
- C10M 2207/123: polycarboxylic
- C10M 2207/127: polycarboxylic
- C10M 2215/042: containing hydroxy groups; Alkoxylated derivatives thereof
- C10M 2215/222: Triazines
- C10M 2215/223: Five-membered rings containing nitrogen and carbon only
- C10M 2219/02: Sulfur-containing compounds obtained by sulfurisation with sulfur or sulfur-containing compounds
- C10M 2219/085: containing carboxyl groups; Derivatives thereof
- C10M 2223/04: Phosphate esters
- C10M 2223/043: Ammonium or amine salts thereof
- C10N 2030/06: Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
- C10N 2030/26: {Waterproofing or water resistance}
- C10N 2040/08: Hydraulic fluids, e.g. brake-fluids
- C10M: LUBRICATING COMPOSITIONS (well drilling compositions C09K8/02); USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION (mould release, i.e. separating, agents for metals B22C3/00, for plastics or substances in a plastic state, in general B29C33/56, for glass C03B40/02; textile lubricating compositions D06M11/00, D06M13/00, D06M15/00; immersion oils for microscopy G02B21/33)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- E21B: EARTH OR ROCK DRILLING; OBTAINING OIL, GAS, WATER, SOLUBLE OR MELTABLE MATERIALS OR A SLURRY OF MINERALS FROM WELLS
- C10N: INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS

## Abstract

A novel hydraulic fluid composition for application to drilling equipment is described herein. These hydraulic fluid compositions permit effective monitoring or controlling well-head pressure of a well during drilling on land or offshore. The hydraulic fluid compositions prevent uncontrolled flow of gas, oil, or another well fluid out of an underground formation during a drilling or extraction process when applied to the drilling equipment. Accordingly, provided is a hydraulic fluid concentrate which contains a water-soluble phosphate ester and a sulfide compound containing at least one S—S linkage, at least 10 carbon atoms and at least one terminal carboxylate group, wherein the S—S linkage bridges two alkyl groups. Additional components can be added to the concentrate and include one or more alkaline compound, one or more dicarboxylic acid or salt thereof, a water-soluble corrosion inhibitor, a water-soluble biocide, a pour point depressant, and water, ethylene glycol, or a combination thereof. The concentrate is then further diluted by the customer for use as described herein. Particularly, these compositions are effective in reducing seawater corrosion of a metal in contact with the hydraulic fluid composition, reducing bioaccumulation in oil drilling equipment contacted with the hydraulic fluid composition, and have low toxicity to sea life.

## Claims

### Claim 1

An aqueous hydraulic fluid concentrate comprising:
(a) a phosphate ester that substantially dissolves in water;
(b) a sulfide compound comprising at least one S—S linkage, at least 10 carbon atoms, and at least one terminal carboxylate group, wherein said S—S linkage bridges two alkyl groups; wherein the ratio of the phosphate ester to the sulfide compound is between 1:1 and 4:1; and
(c) water.

### Claim 2 (depends on 1)

The hydraulic fluid concentrate of claim 1, further comprising one or more of:
an alkaline compound;
a dicarboxylic acid or salt thereof;
a water-soluble corrosion inhibitor;
a water-soluble biocide;
a pour-point depressant; and
ethylene glycol.

### Claim 3 (depends on 2)

The hydraulic fluid concentrate according to claim 2, wherein said alkaline compound is an alkanolamine.

### Claim 4 (depends on 3)

The hydraulic fluid concentrate according to claim 3, wherein said alkanolamine is monoethanolamine, triethanolamine, or a combination thereof.

### Claim 5 (depends on 2)

The hydraulic fluid concentrate according to claim 2, wherein said corrosion inhibitor is an optionally substituted benzotriazole.

### Claim 6 (depends on 5)

The hydraulic concentrate according to claim 5, wherein said benzotriazole is of the structure:
(i) wherein:
R9 is H, C1 to C10 alkyl, or C1 to C6 hydroxyalkyl; and
R10 is H or CH2NR112; and
R11 is H or C1 to C6 alkyl; or
(ii) the compound of (i), wherein R9 is CH2CH2OH; or
(iii) the compound of (i), wherein R11 is CH3; or
(iv) the compound of (i),wherein said optionally substituted benzotriazole is selected from the group consisting of tolyltriazole, 1,2,4-benzotriazole, and 1,2,3-benzotriazole.

### Claim 7 (depends on 2)

The hydraulic fluid concentrate according to claim 2, wherein said dicarboxylic acid is a C8 to C18 dicarboxylic acid or a C10 to C12 dicarboxylic acid or wherein said pour point depressant is a glycol or is ethylene glycol or wherein said water-soluble biocide is triazine.

### Claim 8 (depends on 2)

The hydraulic fluid concentrate according to claim 2, comprising about 40 to about 75% w/w of water, or a combination of water and ethylene glycol.

### Claim 9 (depends on 1)

The hydraulic fluid concentrate according to claim 1, wherein said phosphate ester has the structure:
wherein:
R1R2, and R3 are, independently, OH, optionally substituted C1 to C30 alkoxy, optionally substituted —O—(CH2O)n—(C1 to C30 alkyl), optionally substituted —O—(CH2O)n—(C2 to C30 alkenyl), optionally substituted —O—(CH2O)n—(C2 to C30 alkynyl), —O—(CH2CH2O)n—(C1 to C30 alkyl), —O—(CH2CH2O)n—(C2 to C30 alkenyl), —O—(CH2CH2O)n—(C2 to C30 alkynyl), —O—(CH2CH(CH3)O)n—(C1 to C30 alkyl), —O—(CH2CH(CH3)O)n—(C2 to C30 alkenyl), —O—(CH2CH(CH3)O)n—(C2 to C30 alkynyl), —O—(CH2CH2O)n(CH2CH(CH3)O)n—(C1 to C30 alkyl), —O—(CH2CH2O)n(CH2CH(CH3)O)n—(C2 to C30 alkenyl), —O—(CH2CH2O)n(CH2CH(CH3)O)n—(C2 to C30 alkynyl), —O—(C1 to C30 alkyl)—(OCH2)n—(C1 to C30 alkyl), optionally substituted —O—(C1 to C30 alkyl)—(OCH2CH2)n—(C1 to C30 alkyl), optionally substituted —O—(C1 to C30 alkyl)—(OCH2CH(CH3))n—(C1 to C30 alkyl), optionally substituted —O—(C1 to C30 alkyl)-(OCH2)n—(C2 to C30 alkenyl), optionally substituted —O—(C1 to C6 alkyl)ORAORB; and
RA and RB are, independently, C1 to C30 alkyl, C2 to C30 alkenyl, or C2 to C30 alkynyl.

### Claim 10 (depends on 1)

The hydraulic fluid concentrate according to claim 1, wherein said phosphate ester is:
a C6 to C18 trialkoxyalkyl phosphate ester, each alkoxyalkyl moiety comprising 1 part by weight of an ester or a mixture of esters selected from the group consisting of a trialkyl ester of phosphoric acid and C4 to C9 alkyl alcohols; or
a C6 to C10 trialkyloxyalkyl phosphate ester comprising butoxyethyl, phenoxyethyl, octoxyethyl, butoxybutyl moieties.

### Claim 11 (depends on 1)

The hydraulic fluid concentrate according to claim 1, wherein said sulfide compound contains one —S—S— linkage; or a —S—S—S— linkage; or a —S—S—S—S— linkage.

### Claim 12 (depends on 1)

The hydraulic fluid concentrate according to claim 1, wherein each of said alkyl group bridged by said S—S linkage is terminated with a carboxylate or an amide.

### Claim 13 (depends on 1)

The hydraulic fluid concentrate according to claim 1, wherein said sulfide compound is sulfurized 9-octadecenoic acid comprising at least one terminal amide group on said alkyl.

### Claim 14 (depends on 1)

An aqueous hydraulic fluid composition comprising:
(a) about 1 to about 10% w/w of said hydraulic fluid concentrate of claim 1; and
(b) about 90 to about 99% w/w of water, or a combination of water and ethylene glycol.

### Claim 15 (depends on 14)

A method for monitoring or controlling well-head pressure of a well during drilling or for preventing uncontrolled flow of gas, oil, or another well fluid out of an underground formation during a drilling or extraction process, said method comprising:
(a) performing said drilling or extraction using a hydraulic fluid composition of claim 14;
(b) applying said hydraulic fluid to a blowout preventer; or
(c) performing (a) or (b) in a marine environment.

### Claim 16 (depends on 14)

A method for drilling offshore oil or gas, said method comprising:
(a) applying said hydraulic fluid composition of claim 14 to the drilling equipment; and
(b) drilling said offshore oil using said drilling equipment; and
(c) optionally applying said hydraulic fluid composition to the blowout preventer of said drilling equipment.

### Claim 17 (depends on 1)

The hydraulic fluid concentrate according to claim 1, wherein said phosphate ester is olelyl alcohol ethoxylated phosphate.

### Claim 18

A product comprising:
(i) a first container comprising a phosphate ester that substantially dissolves in water;
(ii) a second container comprising a sulfide compound comprising at least one —S—S— linkage, at least 10 carbon atoms and at least one terminal carboxylate group, wherein said —S—S— linkage bridges two alkyl groups;
(iii) a third container comprising one or more alkaline compound;
(iv) a fourth container comprising one or more dicarboxylic acid or salt thereof;
(v) a fifth container comprising a water-soluble corrosion inhibitor;
(vi) a sixth container comprising a water-soluble biocide; and
(vii) a seventh container comprising a pour point depressant.

### Claim 19

An aqueous hydraulic fluid composition comprising:
(a) from 0.5 to 10% w/w of a phosphate ester that substantially dissolves in water;
(b) about 1 to 10% by weight of a sulfide compound comprising at least one S—S linkage, at least 10 carbon atoms and at least one terminal carboxylate group, wherein said S—S linkage bridges two alkyl groups; wherein the ratio of the phosphate ester to the sulfide compound is between 1:1 and 4:1;
(c) about 1 to 12% by weight of one or a combination of alkaline compounds sufficient to maintain a pH>7;
(d) about 1 to 10% by weight dicarboxylic acid or salt thereof;
(e) about 0.001 to 3% by weight of a corrosion inhibitor;
(f) about 1 to 10% of a biocide that substantially dissolves in water;
(g) about 10 to 30% by weight of a pour-point depressant; and
(h) the balance water.