# US 7,745,546 B2 · Hydrocarbon-terminated polyether-polyamide block copolymers and uses thereof

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- Number: US 7,745,546 B2
- Document ID: US7745546B2
- Status: Granted
- Kind: B2
- Application number: 11/085,385
- Filed: 2005-03-21
- Published: 2005-07-28
- Granted: 2010-06-29
- Earliest claimed: 2001-01-24
- Assignees: Arizona Chemical Company
- Inventors: Richard C. MacQueen; Mark S. Pavlin
- Web page: https://patentgrep.com/patent/US7745546B2

## CPC

- A61K 8/042: {Gels}
- A61K 8/86: Polyethers
- A61K 8/88: Polyamides
- A61K 8/90: Block copolymers (A61K8/89 takes precedence)
- A61L 9/01: Deodorant compositions {(compositions released by contact with a liquid A61L9/05)}
- A61L 9/012: characterised by being in a special form, e.g. gels, emulsions {(A61L9/048 takes precedence)}
- A61Q 1/06: Lipsticks
- A61Q 15/00: Anti-perspirants or body deodorants (deodorisation of air A61L9/00)
- C08G 65/3324: {cyclic}
- C08G 65/333: containing nitrogen
- C08G 69/34: using polymerised unsaturated fatty acids
- C08G 69/40: Polyamides containing oxygen in the form of ether groups (C08G69/12, C08G69/32 take precedence)
- C08G 69/44: Polyester-amides
- C08G 81/00: Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers (involving only carbon-to-carbon unsaturated bond reactions C08F299/00 {; polyester-amides C08G69/44; polyester-imides C08G73/16; polyamides-imides C08G73/14; block- or graft polymers containing polysiloxane sequences C08G77/42})
- C08L 71/02: Polyalkylene oxides
- C11C 5/002: {Ingredients}
- C11D 3/37: Polymers {(polymeric surface-active agents C11D1/008; polysaccharides C11D3/222)}
- C11D 3/3719: {Polyamides or polyimides}
- C11D 3/3788: {Graft polymers}
- C11D 17/00: Detergent materials or soaps characterised by their shape or physical properties (shaping soap C11D13/14)
- C11D 17/0021: {Aqueous microemulsions}
- C11D 17/003: {Colloidal solutions, e.g. gels; Thixotropic solutions or pastes}
- C23F 11/173: Macromolecular compounds
- A61K 2800/262: Transparent; Translucent
- A61Q 1/02: Preparations containing skin colorants, e.g. pigments (preparations in powder form A61Q1/12)
- A61Q 1/04: for lips
- A61Q 1/10: for eyes, e.g. eyeliner, mascara
- A61Q 11/00: Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
- A61Q 13/00: Formulations or additives for perfume preparations (essential oils or perfumes per se C11B9/00)
- A61Q 19/00: Preparations for care of the skin
- C08L 77/00: Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain (of polyhydrazides C08L79/06; of polyamideimides or polyamide acids C08L79/08); Compositions of derivatives of such polymers
- C08L 101/16: the macromolecular compounds being biodegradable
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61L: METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES (preservation of bodies or disinfecting characterised by the agents employed A01N; preserving, e.g. sterilising, food or foodstuffs A23; preparations for medical, dental or toiletry purposes A61K)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C11C: FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C23F: NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE (working metal by laser beams B23K26/00; desurfacing by applying flames B23K7/00; working of metal by electro-erosion B23H; producing decorative effects by removing surface material, e.g. by engraving, by etching, B44C1/22; electrolytic etching or polishing C25F); INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25

## Abstract

A composition comprising (a) a resin composition comprising a block copolymer of the formula hydrocarbon-polyether-polyamide-polyether-hydrocarbon; and (b) a polar liquid. The block copolymer may be prepared by a process comprising reacting together reactants comprising dimer acid, diamine, and a polyether having termination at one end selected from amine, hydroxyl and carboxyl, and termination at another end selected from hydrocarbons. The polar liquid may be one or more of an aromatic liquid, a polar aprotic liquid, a ketone-containing liquid, an ester-containing liquid, an ether-containing liquid, an amide-containing liquid and a sulfoxide-containing liquid. The composition may be a gel at room temperature.

## Claims

### Claim 1

A copolymer of the formula:
wherein, independently,
R1 is C1-8 a hydrocarbon radical;
R2 is a C2-C4 hydrocarbon diradical;
R3 is a C2-C52 hydrocarbon diradical, wherein at least 50% of the diradicals are derived from dimer acid;
R4 is selected from C2-C8 hydrocarbon diradicals and polyether diradicals of the formula: —(R11—O)g—R11—, wherein R11 is a C2-C4 hydrocarbon diradical independently selected at each occurrence and g is an integer ranging from 2 to 50;
Z is selected from O and NH;
x and z are integers from 2 to 100; and
y is an integer equal to 1 or more that provides a copolymer molecular weight of from 2,000 to 50,000.

### Claim 2 (depends on 1)

The copolymer according to claim 1, wherein, independently, R1 is CH3 and Z is NH.

### Claim 3 (depends on 1)

The copolymer according to claim 1, wherein y is an integer from 1 to 10.

### Claim 4 (depends on 1)

The copolymer according to claim 1, wherein y is an integer equal to 1 or more that provides a copolymer number average molecular weight of from 2,000 to 50,000.

### Claim 5 (depends on 1)

A composition, comprising the copolymer according to claim 1; and at least one polar liquid.

### Claim 6 (depends on 5)

The composition according to claim 5, comprising from 5 to 50 wt % of the copolymer.

### Claim 7 (depends on 5)

The composition according to claim 5, wherein the at least one polar liquid comprises an ester-containing liquid.

### Claim 8 (depends on 7)

The composition according to claim 7, wherein the at least one polar liquid comprises an ester-containing liquid having formula R6—CO2—R6 or R6—CO2—R7—CO2—R6, wherein R6 and R7 are organic moieties having from 1 to 12 carbon atoms.

### Claim 9 (depends on 8)

The composition according to claim 8, wherein R6 is selected from C1-C12 alkyl, C1-C12 hydroxy-substituted alkyl, C1-C12 alkoxy-substituted C1-C12 alkyl, C6-C12 aryl-substituted C1-2 alkyl, C1-12 alkenyl, C1-12 hydroxyalkenyl, C1-12 alkoxy-substituted C1-C12 alkenyl, C6-C12 aryl, C1-C12 alkyl-substituted C6-C12 amyl, C6-C12 hydroxy-substituted aryl, and C6-C12 alkoxy-substituted C6-C12 aryl, and R7 is selected from C1-C12 alkylene, C1-C12 hydroxy-substituted alkylene, C2-C12 alkenylene, C6-C12 arylene, C6-C12 hydroxy-substituted arylene, and C1-C12 alkoxy-substituted C6-C12 arylene.

### Claim 10 (depends on 7)

The composition according to claim 7, wherein the ester-containing liquid comprises at least one aromatic ester.

### Claim 11 (depends on 10)

The composition according to claim 10, wherein the aromatic ester is at least one member selected from the group consisting of a (C1-C18 alkyl)benzoate, a (C1-C18 alkyl) salicylate, and a di(C1-C12 alkyl) phthalate.

### Claim 12 (depends on 5)

The composition according to claim 5, wherein the at least one polar liquid comprises at least one member selected from the group consisting of a lower alcohol, glycol, ether, glycol ether, polyalkyleneglycol ether, and polyol.

### Claim 13 (depends on 5)

The composition according to claim 5, wherein the at least one polar liquid comprises at least one member selected from the group consisting of propylene glycol, 2-methoxyethyl ether, diethylene glycol ethyl ether, ethylene glycol, hexylene glycol, ethylene glycol monophenyl ether, di(propylene glycol), di(propylene glycol) monomethyl ether, di(ethylene glycol) dimethyl ether, tripropylene glycol mono methyl ether, poly(ethylene glycol) and poly(propylene glycol).

### Claim 14 (depends on 5)

The composition according to claim 5, wherein the at least one polar liquid comprises from 5 to 90 wt % of at least one surfactant based upon the total weight of the surfactant and copolymer.

### Claim 15 (depends on 5)

The composition according to claim 5, wherein the polar liquid comprises an aromatic liquid.

### Claim 16 (depends on 15)

The composition according to claim 15, wherein the aromatic liquid is at least one member selected from the group consisting of a (C1-C18 alkyl)benzoate, a (C1-C18 alkyl) salicylate, and a di(C1-C12 alkyl) phthalate.

### Claim 17 (depends on 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16)

A personal care product, comprising any one of the compositions according to any one of claims 5 to 16; and a colorant.

### Claim 18 (depends on 1)

An antiperspirant, comprising the copolymer according to claim 1; and
at least one member selected from the group consisting of aluminum chlorohydrate, aluminum sesquichlorohydrate, aluminum dichlorohydrate, aluminum-zirconium chlorohydrates, and aluminum-zirconium polychlorohydrate complexed with glycine.

### Claim 19 (depends on 1)

A lipstick, comprising the copolymer according to claim 1;
at least one polar liquid; and at least one colorant.

### Claim 20 (depends on 1)

A sun care product, comprising the copolymer according to claim 1;
at least one (C1-C18 alkyl) salicylate; and at least one surfactant.

### Claim 21 (depends on 20)

The sun care product according to claim 20, further comprising at least one ester-containing liquid.

### Claim 22 (depends on 1)

An eye make-up product, foundation makeup product, or costume make-up product, comprising the copolymer according to claim 1; at least one ester-containing liquid; and at least one colorant.

### Claim 23 (depends on 1)

A wax, polish, cleaner, or stripper, comprising the copolymer according to claim 1; and at least one ester-containing liquid.

### Claim 24 (depends on 1)

A wax, polish, cleaner, or stripper, comprising the copolymer according to claim 1; and at least one aprotic liquid.

### Claim 25 (depends on 24)

The wax, polish, cleaner, or stripper according to claim 24, comprising from 5 to 90 wt % of at least one aprotic liquid based upon the total weight of the aprotic liquid and copolymer.

### Claim 26 (depends on 25)

The wax, polish, cleaner, or stripper according to claim 25, wherein the at least one aprotic liquid is at least one member selected from the group consisting of N-methyl pyrrolidinone, propylene carbonate, tetrahydrofuran, dimethyl sulfoxide, methylene chloride, and dichloroethane.

### Claim 27 (depends on 1)

A fragrance emitting article, comprising the copolymer according to claim 1; and at least one polar liquid wherein the polar liquid comprises at least one member selected from the group consisting of a liquid fragrance, an essential oil, and a fragrance chemical.

### Claim 28 (depends on 27)

The fragrance emitting article according to claim 27, comprising from 10 to 90 wt % of the at least one polar liquid based upon the total weight of the copolymer and polar liquid.

### Claim 29 (depends on 27)

The fragrance emitting article according to claim 27, comprising from 5 to 50 wt % of the copolymer based upon the total weight of the article.

### Claim 30 (depends on 27)

The fragrance emitting article according to claim 27, wherein the at least one polar liquid further comprises at least one ester-containing liquid.

### Claim 31 (depends on 27, 28, 29, 30)

The fragrance emitting article according to any one of claim 27 to 30, wherein the at least one polar liquid further comprises at least one member selected from the group consisting of a lower alcohol, glycol, ether, glycol ether, polyalkyleneglycol ether, and polyol.