# US 11,299,667 B2 · Fatty acid reaction products of dextrins or dextran formulated with a surfactant

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- Number: US 11,299,667 B2
- Document ID: US11299667B2
- Status: Granted
- Kind: B2
- Application number: 17/343,033
- Filed: 2021-06-09
- Published: 2021-11-04
- Granted: 2022-04-12
- Earliest claimed: 2020-04-29
- Assignees: Integrity Bio-Chemicals, LLC
- Applicants: Integrity Bio-Chemicals, LLC
- Inventors: Christopher P. Gardner; Stephen William Almond
- Web page: https://patentgrep.com/patent/US11299667B2

## CPC

- C09K 8/584: characterised by the use of specific surfactants
- C09K 8/604: {Polymeric surfactants}
- C09K 8/588: characterised by the use of specific polymers {(polymeric surfactants C09K8/584)}
- C09K 8/594: Compositions used in combination with injected gas {, e.g. CO2 orcarbonated gas}(C09K8/592 takes precedence)
- C09K 8/602: {containing surfactants}
- C09K 8/68: containing organic compounds
- C09K 8/703: {Foams}
- C09K 8/90: of natural origin, e.g. polysaccharides, cellulose
- C09K 8/94: Foams
- C11D 1/66: Non-ionic compounds {(C11D1/002, C11D1/004, C11D1/008 take precedence)}
- C11D 1/825: Mixtures of compounds all of which are non-ionic
- C11D 1/835: Mixtures of non-ionic with cationic compounds
- C11D 1/94: Mixtures with anionic, cationic or non-ionic compounds
- C11D 3/2079: {Monocarboxylic acids-salts thereof}
- C11D 3/22: Carbohydrates or derivatives thereof
- C11D 3/221: {Mono, di- or trisaccharides or derivatives thereof}
- C11D 3/222: {Natural or synthetic polysaccharides, e.g. cellulose, starch, gum, alginic acid or cyclodextrin}
- C11D 3/226: {esterified}
- C11D 11/04: by chemical means, e.g. by sulfonating in the presence of other compounding ingredients followed by neutralising
- C09K 2208/28: Friction or drag reducing additives
- C11D 1/46: Esters of carboxylic acids with amino alcohols; Esters of amino carboxylic acids with alcohols
- C11D 1/523: {Carboxylic alkylolamides, or dialkylolamides, or hydroxycarboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain one hydroxy group per alkyl group}
- C11D 1/662: {Carbohydrates or derivatives}
- C11D 1/72: Ethers of polyoxyalkylene glycols
- C11D 1/90: Betaines
- C11D 3/33: Amino carboxylic acids
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL

## Abstract

Compositions comprising a neutral surfactant or a reaction product thereof and a reaction product of a saccharide polymer and a fatty acid may be obtained in the presence of water and a hydroxide base (optionally in the presence of the neutral surfactant), the saccharide polymer comprising a dextran, a dextrin compound, or any combination thereof. The reaction product of the saccharide polymer and the fatty acid may be present at a concentration effective to lower surface tension of the neutral surfactant. Depending on the fatty acid identity, among other factors, the compositions may promote emulsification or de-emulsification. In addition, the compositions may promote foam formation under appropriate conditions. Treatment fluids comprising the compositions, including foamed treatment fluids, may be introduced into a subterranean formation to perform a treatment operation in which fluid emulsification or de-emulsification may occur. The reaction products may be incorporated in soaps and other personal care products.

## Claims

### Claim 1

A composition comprising:
an aqueous phase comprising an aqueous carrier fluid;
a neutral surfactant or a reaction product thereof; and
a reaction product of a saccharide polymer and a fatty acid, the saccharide polymer comprising a dextran, a dextrin compound, or any combination thereof, wherein the fatty acid consists of one or more straight chain fatty acids comprising about 4 to about 30 carbon atoms;
wherein the neutral surfactant or the reaction product thereof and the reaction product of the saccharide polymer and the fatty acid are dissolved as a solution in the aqueous phase; and
wherein the reaction product of the saccharide polymer and the fatty acid is present at a concentration effective to lower a surface tension of the neutral surfactant in the aqueous phase.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the saccharide polymer comprises a dextrin compound and the dextrin compound comprises a maltodextrin.

### Claim 3 (depends on 1)

The composition of claim 1, wherein the fatty acid comprises at least one fatty acid selected from the group consisting of butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelabonic acid, capric acid, undecylic acid, lauric acid, tridecylic acid, myristic acid, pentadecylic acid, palmitic acid, margaric acid, stearic acid, nonadecylic acid, arachidic acid, heneicosylic acid, behenic acid, trioscylic acid, lignoceric acid, pentacosylic acid, cerotic acid, carboceric acid, montanic acid, nonacosylic acid, melissic acid, crotonic acid, cervonic acid, linoleic acid, linolelaidic acid, linolenic acid, arachidonic acid, docosatetraenoic acid, myristoleic acid, palmitoleic acid, sappenic acid, vaccenic acid, paullinic acid, oleic acid, pinolenic acid, stearidonic acid, eleostearic acid, elaidic acid, gondoic acid, gadoleic acid, erucic acid, eicosenoic acid, eicosadiencoic acid, eicosatrienoic acid, eicosatetraenoic acid, docosadienoic acid, nervonic acid, mead acid, adrenic acid, and any combination thereof.

### Claim 4 (depends on 1)

The composition of claim 1, wherein the neutral surfactant comprises cocamide diethanolamine or a reaction product thereof.

### Claim 5 (depends on 1)

The composition of claim 1, wherein the reaction product of the saccharide polymer and the fatty acid is formed in the presence of the neutral surfactant.

### Claim 6 (depends on 1)

The composition of claim 1, wherein a molar ratio of fatty acid to saccharide polymer in the reaction product is about 0.2 or above on a basis of molesfatty acid:molesglucose monomers.

### Claim 7 (depends on 1)

The composition of claim 1, wherein the reaction product of the saccharide polymer is obtained in the presence of water and a hydroxide base.

### Claim 8 (depends on 1)

The composition of claim 1, wherein the reaction product of the saccharide polymer comprises a fatty ester reaction product.

### Claim 9 (depends on 1)

A foamable formulation comprising the composition of claim 1.

### Claim 10 (depends on 9)

The foamable formulation of claim 9, wherein the foamable formulation comprises a soap.

### Claim 11 (depends on 1)

A method comprising:
providing an aqueous fluid comprising the composition of claim 1; and
inducing foam formation in the aqueous fluid.

### Claim 12 (depends on 11)

The method of claim 11, wherein inducing foam formation comprises agitating the aqueous fluid to introduce gas thereto as a plurality of bubbles.

### Claim 13 (depends on 1)

The composition of claim 1, wherein a molar ratio of fatty acid to saccharide polymer in the reaction product is about 0.2 to about 1.0 on a basis of molesfatty acid:molesglucose monomers.