# US 4,395,353 A · Polyanionic heteropolysaccharide biopolymers

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- Number: US 4,395,353 A
- Document ID: US4395353A
- Status: Granted
- Kind: A
- Application number: 06/146,056
- Filed: 1980-05-14
- Granted: 1983-07-26
- Earliest claimed: 1979-02-22
- Assignees: Petroleum Fermentations N.V.
- Inventors: David L. Gutnick; Eugene Rosenberg; Igal Belsky; Zosim Zinaida
- Web page: https://patentgrep.com/patent/US4395353A

## CPC

- C09K 8/905: {Biopolymers}
- B01D 21/01: using flocculating agents (for purifying water C02F1/52; for liquid radioactive waste G21F9/10)
- C02F 1/5263: {using natural chemical compounds}
- C02F 1/682: {by addition of chemical compounds for dispersing an oily layer on water}
- C09K 23/16: Amines or polyamines
- C09K 23/30: Proteins; Protein hydrolysates
- C12N 1/205: Bacterial isolates
- C12P 1/04: by using bacteria
- C12P 19/26: Preparation of nitrogen-containing carbohydrates
- C12R 2001/01: Bacteria or Actinomycetales {; using bacteria or Actinomycetales}
- Y10S 210/925: using chemical agent
- Y10S 507/937: with emulsion
- Y10S 516/02: Organic and inorganic agents containing, except water
- Y10S 516/917: The agent contains organic compound containing oxygen
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)
- C02F: TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE (separation in general B01D; special arrangements on waterborne vessels of installations for treating water, waste water or sewage, e.g. for producing fresh water, B63J; adding materials to water to prevent corrosion C23F; treating radioactively-contaminated liquids G21F9/04; regeneration of reactants for recirculation into processes, see the relevant places for the processes)
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)
- C12P: FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {(brewing of beer C12C; producing vinegar C12J; producing specific peptides or proteins C07K; producing enzymes C12N9/00; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; measuring or testing processes involving enzymes or microorganisms C12Q; measuring or testing processes involving nucleic acid amplification reactions C12Q1/6844; fermentation processes to form a food composition, A21 or A23; compounds in general, see the relevant compound class, e.g. C01, C07)}
- C12R: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

Growth of Acinetobacter Sp. ATCC 31012 on various substrates and under varying conditions has been used to produce two classes of extracellular microbial protein-associated lipopolysaccharides (the "emulsans") which, on a weight-for-weight basis, are probably the most efficient emulsifiers discovered and which possess certain characteristics that permit these unique extracellular microbial lipopolysaccharides to be widely used in cleaning oil-contaminated vessels, oil spill management, and enhanced oil recovery by chemical flooding. Emulsans and apoemulsans, both of which biopolymers are strongly anionic, exhibit a high degree of specificity in the emulsification of hydrocarbon substrates which contain both aliphatic and cyclic components. In addition, these extracellular microbial polysaccharides as well as their O-deacylated and N-deacylated derivatives are adsorbed on and capable of flocculating aluminosilicate ion-exchangers, such as kaolin and bentonite.

## Claims

### Claim 1

Polyanionic heteropolysaccharide biopolymers in which (a) substantially all of the sugar moieties are N-acylated aminosugars, a portion of which is N-acylated-D-galactosamine and another portion of which is N-acylated aminouronic acid, a part of the N-acyl groups of such heteropolysaccharide being N-3-hydroxydodecanoyl groups; and (b) at least 0.2 micromoles per milligram of such heteropolysaccharide consisting of fatty acid esters in which (1) the fatty acids contain about 10 to about 18 carbon atoms and (2) about 50 percent by weight or higher of such fatty acids are composed of 2-hydroxydodecanoic acid and 3-hydroxydodecanoic acid.

### Claim 2 (depends on 1)

Polyanionic heteropolysaccharide biopolymers according to claim 1, in which the fatty acids of the 0-lipoacyl esters have an average equivalent weight from about 200 to about 230.

### Claim 3 (depends on 1)

Polyanionic heteropolysaccharide biopolymers according to claim 1, in which the fatty acids esters constitute at least 0.5 micromoles per milligram of such heteropolysaccharide.

### Claim 4 (depends on 1)

Polyanionic heteropolysaccharide biopolymers according to claim 1, in which the fatty acid esters constitute from about 0.5 to about 0.75 micromoles per milligram of such heteropolysaccharide.

### Claim 5 (depends on 1)

Polyanionic heteropolysaccharide biopolymers according to claim 1, in which the heteropolysaccharide is in the form of a salt of a divalent cation.

### Claim 6 (depends on 1, 2, 3, 4)

Polyanionic heteropolysaccharide biopolymers according to any of claims 1, 2, 3, 4, or 5 in which the ratio of 2-hydroxydodecanoic acid to 3-hydroxydodecanoic acid in the 0-lipoacyl portion of such heteropolysaccharide is in the range from about 1:4 to about 1:1.

### Claim 7 (depends on 1, 2, 3, 4)

Polyanionic heteropolysaccharide biopolymers according to any of claims 1, 2, 3, 4, or 5 in which the ratio of 2-hydroxydodecanoic acid to 3-hydroxydodecanoic acid in the 0-lipoacyl of such heteropolysaccharide is in the range from about 1:4 to about 1:2.

### Claim 8 (depends on 1, 2, 3, 4)

Polyanionic heteropolysaccharide biopolymers according to any of claims 1, 2, 3, 4, or 5, in which the heteropolysaccharide is in the form of its magnesium salt.

### Claim 9 (depends on 1, 2, 3, 4)

Polyanionic heteropolysaccharide biopolymers according to any of claims 1, 2, 3, 4, or 5, in which the heteropolysaccharide biopolymer is complexed with a protein and is characterized by a Specific Emulsification Activity of about 200 units per milligram or higher, where one unit per milligram of Specific Emulsification Activity is defined as that amount of emulsifying activity per milligram of the protein-complexed biopolymer which yields 100 Klett absorption units using a standard hydrocarbon mixture consisting of 0.1 ml of 1:1 (v/v) hexadecane/2-methylnaphthalene and 7.5 ml of Tris-Mg buffer.

### Claim 10 (depends on 1)

Polyanionic heteropolysaccharide biopolymers of claim 1 further comprising divalent metal, ammonium and quaternary ammonium salts of such polyanionic heteropolysaccharide biopolymers.