Hydrophilic modification of water insoluble polysaccharide as surface-active agents

Patent metadata

Field	Value
Publication number	US-9815912-B2
Application number	US-201313841903-A
Country	US
Kind code	B2
Filing date	Mar 15, 2013
Priority date	Mar 19, 2012
Publication date	Nov 14, 2017
Grant date	Nov 14, 2017

Abstract

A surfactant produced by reacting naturally occurring polysaccharides that are not water soluble with a hydrophilic substituent on a carboxylic portion of the polysaccharide. In a second reaction, the surfactant is further substituted on a hydroxylic portion with a hydrophobic or lipophilic substituent, so as to make the reaction product both water soluble and capable of attracting oily material that is hydrophobic to be removed from a substrate by cleaning in water. Methods of making the surfactant and the follow-on reaction product are described.

First claim

What is claimed is:

1. A composition of matter, comprising:
a reaction product of a naturally occurring polysaccharide having a backbone structure comprising a plurality of monomer units, each monomer unit having at least one of a carboxylic group or an amine group and having at least one hydroxyl group, wherein said naturally occurring polysaccharide is selected from the group consisting of a polysaccharide derivative of polygalacturonic acid, and a polysaccharide derivative of alginic acid; and
a hydrophilic moiety configured to react with some of said at least one of a carboxylic group or an amine group of said naturally occurring polysaccharide, said hydrophilic moiety being 2-aminoethanesulfonate (taurine);
said reaction product retaining said backbone structure and having surface active properties in liquids, said reaction product being a non-toxic biodegradable surfactant that when present in water is configured to reduce a surface tension in deionized water of 73.02 mN/m to a surface tension in the range of 36.08 mN/m to 33.49 mN/m measured in 0.1% analyte concentration at 24° C. using the Du Noüy ring method.

2. The composition of matter of claim 1 , comprising a further reaction product retaining said backbone structure and having some of said at least one hydroxyl or one carboxylic acid group of said naturally occurring polysaccharide substituted with a hydrophobic or a lipophilic moiety, said hydrophobic or said lipophilic moiety comprising a selected one of lauryl alcohol, stearyl alcohol, and a saturated fatty alcohol of chain length in the range from C 5 to C 22 .

3. The composition of matter of claim 2 , wherein said hydrophobic or said lipophilic moiety is a naturally occurring fatty alcohol.

4. A method of making a composition of matter, comprising the steps of:
providing a naturally occurring polysaccharide having a backbone structure comprising a plurality of monomer units, each monomer unit having at least one of a carboxylic group or an amine group and having at least one hydroxyl group, wherein said naturally occurring polysaccharide is selected from the group consisting of a polysaccharide derivative of polygalacturonic acid, and a polysaccharide derivative of alginic acid;
reacting said naturally occurring polysaccharide with a hydrophilic moiety that substitutes for some of said at least one of a carboxylic group or an amine group of said naturally occurring polysaccharide, said hydrophilic moiety being 2-aminoethanesulfonate (taurine); and
recovering a reaction product that retains said backbone structure and is surface active in liquids, said reaction product when present in water is configured to reduce a surface tension in deionized water of 73.02 mN/m to a surface tension in the range of 36.08 mN/m to 33.49 mN/m measured in 0.1% analyte concentration at24° C. using the Du Noüy ring method.

5. The method of making a composition of matter of claim 4 , wherein said reacting step is performed using applied microwave energy.

6. The method of making a composition of matter of claim 4 , wherein said reacting step is performed using thermal energy.

7. The method of making a composition of matter of claim 4 , wherein said reacting step involves a catalyst.

8. The method of making a composition of matter of claim 4 , further comprising the steps of:
reacting said reaction product that retains said backbone structure with a hydrophobic or lipophilic moiety that substitutes for some of said at least one of a hydroxyl group or carboxylic acid group of said naturally occurring polysaccharide; and
recovering a second reaction product that retains said backbone structure and has both hydrophilic and hydrophobic/lipophilic properties.

9. The method of making a composition of matter of claim 8 , wherein said hydrophobic or lipophilic moiety is a naturally occurring fatty alcohol.

10. The method of making a composition of matter of claim 9 , wherein said naturally occurring fatty alcohol is a selected one of lauryl alcohol, stearyl alcohol, and a saturated fatty alcohol of chain length in the range from C 5 to C 22 .

11. The composition of matter of claim 1 , wherein said polysaccharide has a molecular weight in the range of 500 to 150,000 daltons.

12. The composition of matter of claim 2 , wherein said polysaccharide has a molecular weight in the range of 500 to 150,000 daltons.

Assignees

• Aris Zarif Farhana Mohd
• Bouldin Ryan M
• Nagarajan Ramaswamy
• Budhlall Bridgette
• Bavishi Vishal
• Univ Massachusetts

Inventors

• Aris Zarif Farhana Mohd
• Bouldin Ryan M
• Nagarajan Ramaswamy
• Budhlall Bridgette
• Bavishi Vishal

Classifications

• C08B37/0084

  Guluromannuronans, e.g. alginic acid, i.e. D-mannuronic acid and D-guluronic acid units linked with alternating alpha- and beta-1,4-glycosidic bonds; Derivatives thereof, e.g. alginates · CPC title

• C08B37/0045 Primary

  alpha-D-Galacturonans, e.g. methyl ester of (alpha-1,4)-linked D-galacturonic acid units, i.e. pectin, or hydrolysis product of methyl ester of alpha-1,4-linked D-galacturonic acid units, i.e. pectinic acid; Derivatives thereof · CPC title

• C12P19/26

  Preparation of nitrogen-containing carbohydrates · CPC title

• C08B37/003

  Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; Derivatives thereof · CPC title

• C08B37/00

  Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof (cellulose D21; {microbiological processes C12P}) · CPC title