Monomers, oligomers and polymers of sugars functionalized with straight or branched fatty acids and derivatives, their compositions and uses

Patent metadata

Field	Value
Publication number	US-12486382-B2
Application number	US-202117915866-A
Country	US
Kind code	B2
Filing date	Apr 16, 2021
Priority date	Apr 17, 2020
Publication date	Dec 2, 2025
Grant date	Dec 2, 2025

Abstract

The present invention relates to monomers, oligomers and polymers of sugars functionalized with straight or branched fatty acid and derivatives, their compositions and their uses.

First claim

The invention claimed is:

1 . A polyol fatty ester, comprising:
(i) a fatty moiety selected from:
a branched fatty moiety, which is a straight C14, C16, C18 or C20 lipid carboxyl group carrying a 10-methyl or 10-methylene branched substituent, or
a straight fatty moiety, which is a straight C14, C16, C18 or C20 lipid carboxyl group carrying a unique unsaturation in a position ranging from 7 to 10,
(ii) a polyol moiety having at least one hydroxyl group, which is a polymer composition of a C6 carbohydrate in the form of a dextrin having optionally branched polymer chain comprising more than 50 wt % of from 12 to 35 C6 carbohydrate monomers, wherein each polyol moiety in the said polymer is identical or different, wherein the polyol fatty ester contains at least one fatty moiety according to (i), which is linked by ester bonding to the at least one hydroxyl group of the polyol moiety according to (ii), wherein all the hydroxyl groups present on the polyol moiety are esterified.

2 . The polyol fatty ester of claim 1 , wherein the fatty moiety (i) is a branched fatty moiety selected from 10-methylstearyl, 10-methylenestearyl, 10-methylpalmityl, 10-methylenepalmityl, 10-methylarachidyl, 10-methylenearachidyl, 10-methylmyristyl or 10-methylenemyristyl, and their combinations.

3 . The polyol fatty ester of claim 2 , wherein the branched fatty moiety, when selected among 10-methylstearyl, 10-methylpalmityl, 10-methylarachidyl and 10-methylmyristyl, is chosen among (R) and(S) enantiomers.

4 . The polyol fatty ester of claim 1 , wherein the dextrin has optionally branched polymer chain comprising more than 50 wt % of from 15 to 30 C6 carbohydrate monomers.

5 . The polyol fatty ester of claim 1 , wherein the degree of substitution of the dextrin by the branched fatty moiety, per glucose unit, is higher than 2.70.

6 . The polyol fatty ester of claim 5 , wherein the branched fatty moiety is 10-methylstearyl; the polyol moiety is a dextrin polymer having in average 20 glucose units, and the degree of substitution of the dextrin by the branched fatty moiety is 3.10.

7 . The polyol fatty ester of claim 1 , further comprising at least one:
(i) linear or branched, saturated or unsaturated, C2-C24 lipid carboxyl, or (ii) linear or branched, saturated or unsaturated, C2-C24 lipid carboxyl, wherein at least one carbon atom is substituted with a C1-C6 alkoxy, C1-C6 alkoyloxy, C1-C6 alkylamino or C1-C6 dialkylamino, which is esterified to at least one further hydroxyl group of the dextrin polymer according to (ii).

8 . The polyol fatty ester of claim 7 , wherein the C2-C24 lipid carboxyl is chosen among acetyl, propionyl, acryloyl, and methacryloyl, and the C3-C24 lipid carboxyl is chosen among 2-acetyloxypropionyl, 2-methoxypropionyl, 2-ethoxypropionyl, 2-acetyloxyacetyl, 2-methoxyacetyl and 2-ethoxyacetyl.

9 . A first composition comprising at least 0.1 wt % and at most 99.9 wt % of a polyol fatty ester, according to claim 1 , and further comprising
(a) a linear or branched C8-C20 paraffin or olefin, and/or (b) a mono-, di- or tri-glyceride having a C4-C24 optionally unsaturated optionally branched fatty ester, and/or (c) a phospholipid comprising one or two C8-C24 optionally unsaturated fatty ester bound to glycerol 1-phosphate, and/or (d) water.

10 . The first composition according to claim 9 , comprising from 96 wt % to 40 wt % of polyol fatty ester, and from 4 wt % to 60 wt % of a fluid having an initial boiling point and a final boiling point in the range of from 373°K to 673°K, the fluid comprising more than 95 wt % of isoparaffins and less than 100 ppm aromatic by weight, based on the total weight of the fluid.

11 . The first composition according to claim 10 , wherein the fluid has a biodegradability at 28 days of at least 60%, measured according to OECD 306.

12 . The first composition according to according to claim 10 , wherein the fluid comprises:
C15 isoparaffins and C16 isoparaffins in a combined amount of 80 to 98% by weight based on the total weight of the fluid; or C16 isoparaffins, C17 isoparaffins and C18 isoparaffins in a combined amount of 80 to 98% by weight based on the total weight of the fluid; or C17 isoparaffins and C18 isoparaffins in a combined amount of 80 to 98% by weight based on the total weight of the fluid.

13 . A second composition comprising from 10 wt % to 90 wt % of the first composition according to claim 9 , and a lipophilic material.

14 . A method of preparing (a) a wettability modifying composition, (b) an oil-in-water or water-in-oil emulsion, (c) a pharmaceutical or veterinary form, (d) an antibacterial, insecticide, nematocide or antifungal, (e) an additive for polymer processing, (f) a food additive, (g) a non-metabolizable substitute of fat for weight control in mammalian species, (h) an additive for paper processing, (i) an additive for biotechnological processing and solubilization of proteins and immune active molecules, (j) a adhesive composition, (k) a biodegradable polymer, (l) a lubricant, (m) a coating, (n) a paint, (o) an insulating media, (p) an anticorrosion composition, (q) a gas permeation and diffusion mitigation, (r) a gelation of oil, or (s) a cosmetic composition comprising the step of adding the polyol fatty ester or composition thereof according to claim 1 .

15 . The polyol fatty ester of claim 2 , wherein the branched fatty moiety selected from 10-methylstearyl, 10-methylpalmityl, 10-methylarachidyl or 10-methylmyristyl, and their combinations, more preferably 10-methylstearyl or 10-methylpalmityl, and their combinations.

16 . The polyol fatty ester of claim 3 , comprising the (R) enantiomer.

17 . The polyol fatty ester of claim 1 , wherein the dextrin has optionally branched polymer chain comprising more than 50 wt % of from 17 to 23 C6 carbohydrate monomers.

18 . A method of preparing (a) a wettability modifying composition, (b) an oil-in-water or water-in-oil emulsion, (c) a pharmaceutical or veterinary form, (d) an antibacterial, insecticide, nematocide or antifungal, (e) an additive for polymer processing, (f) a food additive, (g) a non-metabolizable substitute of fat for weight control in mammalian species, (h) an additive for paper processing, (i) an additive for biotechnological processing and solubilization of proteins and immune active molecules, (j) a adhesive composition, (k) a biodegradable polymer, (l) a lubricant, (m) a coating, (n) a paint, (o) an insulating media, (p) an anticorrosion composition, (q) a gas permeation and diffusion mitigation, (r) a gelation of oil, or (s) a cosmetic composition comprising the step of adding the first composition of claim 9 .

19 . A method of preparing (a) a wettability modifying composition, (b) an oil-in-water or water-in-oil emulsion, (c) a pharmaceutical or veterinary form, (d) an antibacterial, insecticide, nematocide or antifungal, (e) an additive for polymer processing, (f) a food additive, (g) a non-metabolizable substitute of fat for weight control in mammalian species, (h) an additive for paper processing, (i) an additive for biotechnological processing and solubilization of proteins and immune active molecules, (j) a adhesive composition, (k) a biodegradable polymer, (l) a lubricant, (m) a coating, (n) a paint, (o) an insulating media, (p) an anticorrosion composition, (q) a gas permeation and diffusion mitigation, (r) a gelation of oil, or(s) a cosmetic composition comprising the step of adding the second composition of claim 13 .

20 . The second composition of

Assignees

• Totalenergies Onetech

Inventors

• Swoboda Benjamin
• Raboin Jean-Christophe

Classifications

• C08L2205/035

  containing four or more polymers in a blend · CPC title

• C08B31/04 Primary

  of organic acids {, e.g. alkenyl-succinated starch} · CPC title

• C08L3/06 Primary

  Esters · CPC title

• C08B3/10

  with five or more carbon-atoms, {e.g. valerate} · CPC title

• C08B37/0006

  Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid · CPC title