# US 7,612,136 B2 · Anionic and other derivatives of non-ionic surfactants, methods for making, and uses in emulsion polymerization and polymer dispersions

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- Number: US 7,612,136 B2
- Document ID: US7612136B2
- Status: Granted
- Kind: B2
- Application number: 11/930,300
- Filed: 2007-10-31
- Published: 2008-05-15
- Granted: 2009-11-03
- Earliest claimed: 2006-11-03
- Assignees: Cognis IP Management GmbH
- Inventors: Ana Maria Fernandez; Michael Allen; Richard Crews
- Web page: https://patentgrep.com/patent/US7612136B2

## CPC

- C09K 23/017: {Mixtures of compounds}
- C08F 2/26: anionic
- C08F 2/30: non-ionic
- C08K 5/41: Compounds containing sulfur bound to oxygen
- C08K 5/51: Phosphorus bound to oxygen
- C11D 1/37: Mixtures of compounds all of which are anionic
- C11D 1/123: {derived from carboxylic acids, e.g. sulfosuccinates}
- C11D 1/146: {Sulfuric acid esters}
- C11D 1/29: Sulfates of polyoxyalkylene ethers
- C11D 1/345: {Phosphates or phosphites}
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL

## Abstract

An anionic surfactant concentrate and method for making includes providing compound (I) R1—OH where R1 represents a branched C6-22 radical with average branching of about 2-8 per radical; providing compound (II): where R2 represents a C8-16 radical; mixing (I) and (II); ethoxylating to obtain a reaction product; reacting with a sulfating, phosphating, or sulfitation agent to obtain R1—O—[CH2—CH2O]n-A and where R1 represents a branched C6-22 radical with average branching of about 2-8, R2 represents a C8-16 radical, A represents —SO3M, —PO3M, —PO3M2, —OCCH2CH(SO3Na)COO—, or HOOCCH2CH(SO3Na)COO—, M represents a positive counterion, n represents a value from 0-100, and x and y each represents a value from 0-100, where the sum of x and y represents a value of at least 1 to 100 are provided. Anionic surfactant compositions containing the concentrate and methods for stabilizing are also provided.

## Claims

### Claim 1

An anionic surfactant concentrate, comprising:
(a) a compound according to general formula (III):
R1—O—[CH2—CH2O]n-A (III)
wherein R1 represents a saturated or unsaturated, branched C6-22 radical with an average branching of about 2 to about 8 per radical, A represents —SO3M, —PO3M, —PO3M2, —OOCCH2CH(SO3Na)COO—, or HOOCCH2CH(SO3Na)COO—, M represents a positive counterion, and n represents a value from 0 to about 100; and
(b) a compound according to general formula (IV):
wherein R2 represents a saturated or unsaturated C8-16 radical, each A represents —SO3M, —PO3M, —PO3M2, —OOCCH2CH(SO3Na)COO—, or HOOCCH2CH(SO3Na)COO—, M represents a positive counterion, and x and y each represent a value from 0 to about 100, wherein the sum of x and y represents a value of at least 1 to 100.

### Claim 2 (depends on 1)

The anionic surfactant concentrate according to claim 1, wherein n represents a value from 0 to about 75.

### Claim 3 (depends on 1)

The anionic surfactant concentrate according to claim 1, wherein x and y each represents a value from 0 to about 75, and the sum of x and y represents a value of at least 1 to 75.

### Claim 4 (depends on 1)

The anionic surfactant concentrate according to claim 1, wherein R2 contains about 6 to about 14 carbon atoms.

### Claim 5 (depends on 1)

The anionic surfactant concentrate according to claim 1, wherein R1 predominantly contains 13 carbon atoms.

### Claim 6 (depends on 1)

The anionic surfactant concentrate according to claim 1, wherein R1 is saturated and has an average branching of about 2 to about 4 per radical.

### Claim 7 (depends on 1)

The anionic surfactant concentrate according to claim 1, wherein M is derived from the group consisting of: sodium hydroxide, ammonium hydroxide, potassium hydroxide, triethanolamine, isopropanolamine, and metal hydroxides.

### Claim 8 (depends on 1)

The anionic surfactant concentrate according to claim 1, wherein component (a) is present in an amount from about 99% to about 10% by weight, and component (b) is present in an amount from about 1% to about 90% by weight.

### Claim 9 (depends on 1)

The anionic surfactant concentrate according to claim 1, wherein the anionic surfactant concentrate is added to an emulsion polymer or a polymer dispersion as an additive in the emulsion polymerization of ethylenically unsaturated monomers to carry out the polymerization reaction.

### Claim 10

A method for making an anionic surfactant concentrate, comprising the steps of:
(a) providing at least one alcohol according to the general formula (1):
R1—OH (I)
wherein R1 represents a saturated or unsaturated, branched C6-22 radical with an average branching of about 2 to about 8 per radical;
(b) providing at least one diol according to the general formula (II):
wherein R2 represents a saturated or unsaturated C8-16 radical;
(c) combining compound (a) and compound (b) to form a mixture;
(d) ethoxylating the mixture to obtain a reaction product;
(e) reacting the reaction product with a compound selected from the group consisting of sulfating agents, phosphating agents, and sulfitation agents to obtain a sulfate, a phosphate ester, or a sulfosuccinate compound, respectively, according to general formula (III):
R1—O—[CH2—CH2O]n-A (III)
wherein R1 represents a saturated or unsaturated, branched C6-22 radical with an average branching of about 2 to about 8 per radical, A represents —SO3M, —PO3M, —PO3M2, —OOCCH2CH(SO3Na)COO—, or HOOCCH2CH(SO3Na)COO—, M represents a positive counterion, and n represents a value from 0 to about 100; and a compound according to general formula (IV):
wherein R2 represents a saturated or unsaturated C8-16 radical, A represents —SO3M, —PO3M, —PO3M2, —OOCCH2CH(SO3Na)COO—, or HOOCCH2CH(SO3Na)COO—, M represents a positive counterion, and x and y each represents a value from 0 to about 100, wherein the sum of x and y represents a value of at least 1 to 100; and
(f) diluting with water.

### Claim 11 (depends on 10)

The method according to claim 10, further comprising the step of neutralizing the sulfates or phosphate esters obtained in step (e) with an alkali source.

### Claim 12 (depends on 11)

The method according to claim 11, wherein the alkali source is selected from the group consisting of: sodium hydroxide, ammonium hydroxide, triethanolamine, and isopropanolamine, and metal hydroxides.

### Claim 13 (depends on 10)

The method according to claim 10, wherein step (d) further comprises conducting at a temperature of from about 100° C. to about 180° C., and at a maximum pressure of about 70 psi.

### Claim 14 (depends on 10)

The method according to claim 10, wherein step (d) further comprises adding an alkali catalyst.

### Claim 15 (depends on 1)

The anionic surfactant concentrate according to claim 1, to which water is added to form a liquid, anionic surfactant composition.

### Claim 16 (depends on 15)

The liquid, anionic surfactant composition according to claim 15, wherein the concentrate is present in an amount of from about 30% to about 90% by weight, based on the total weight of the liquid anionic surfactant composition.

### Claim 17 (depends on 15)

The liquid, anionic surfactant composition according to claim 15, wherein the viscosity at 25° C. is less than 2000 cps.

### Claim 18 (depends on 15)

The liquid, anionic surfactant composition according to claim 15, wherein the viscosity at 25° C. is less than 1000 cps.

### Claim 19 (depends on 15)

The liquid, anionic surfactant composition according to claim 15, wherein the liquid, anionic surfactant composition is added to an emulsion polymer or a polymer dispersion as an additive in the emulsion polymerization of ethylenically unsaturated monomers to carry out the polymerization reaction.

### Claim 20

A method for stabilizing an emulsion polymer or a polymer dispersion, comprising the step of:
adding, to an emulsion polymer or polymer dispersion, from about 0.3% to about 10% by weight of a liquid anionic surfactant composition, based on the total weight of the emulsion polymer or polymer dispersion, comprising:
(a) a compound according to general formula (III):
R1—O—[CH2—CH2O]n-A (III)
wherein R1 represents a saturated or unsaturated, branched C6-22 radical with an average branching of about 2 to about 8 per radical, A represents —SO3M, —PO3M, —PO3M2, —OOCCH2CH(SO3Na)COO—, or HOOCCH2CH(SO3Na)COO—, M represents a positive counterion, and n represents a value from 0 to about 100;
(b) a compound according to general formula (IV):
wherein R2 represents a saturated or unsaturated C8-16 radical, each A represents —SO3M, —PO3M, —PO3M2, —OOCCH2CH(SO3Na)COO—, or HOOCCH2CH(SO3Na)COO—, M represents a positive counterion, and x and y each represent a value from 0 to about 100, wherein the sum of x and y represents a value of at least 1 to 100; and
(c) water.