# US 10,370,482 B2 · Lactam-functionalized polymer, compositions and applications thereof

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- Number: US 10,370,482 B2
- Document ID: US10370482B2
- Status: Granted
- Kind: B2
- Application number: 15/636,991
- Filed: 2017-06-29
- Published: 2018-01-04
- Granted: 2019-08-06
- Earliest claimed: 2016-07-01
- Assignees: Hercules Incorporated
- Applicants: Hercules LLC
- Inventors: Kelly A. Brush; Todd A. Brugel
- Web page: https://patentgrep.com/patent/US10370482B2

## CPC

- C08G 18/833: {by nitrogen containing compounds (by azo compounds C08G18/85)}
- C08F 8/30: Introducing nitrogen atoms or nitrogen-containing groups
- C08F 283/065: {on to unsaturated polyethers, polyoxymethylenes or polyacetals}
- C08G 18/48: Polyethers
- C08G 18/728: {Polymerisation products of compounds having carbon-to-carbon unsaturated bonds and having isocyanate or isothiocyanate groups or groups forming isocyanate or isothiocyanate groups}
- C08G 65/33327: {cyclic}
- C08G 65/337: containing other elements (organic compounds containing halogens only as halides of a carboxyl group C08G65/332)
- C08G 69/14: Lactams
- C09D 171/02: Polyalkylene oxides
- C08F 2810/40: taking place solely at one end or both ends of the polymer backbone, i.e. not in the side or lateral chains
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)

## Abstract

A lactam-functionalized polymer is disclosed. The lactam-functionalized polymer includes lactam-functionalized polyacetal polyether, polyhemiaminal polyether or polyaminal polyether. The applications of the lactam-functionalized polymer are also disclosed.

## Claims

### Claim 1

A lactam-functionalized polymer comprising:
a polymer backbone and at least one lactam-containing moiety attached to the polymer backbone or pendant on the polymer backbone, wherein the polymer backbone is selected from the group consisting of polyacetal polyether, polyhemiaminal polyether, polyaminal polyether, and combinations thereof.

### Claim 2 (depends on 1)

The lactam-functionalized polymer of claim 1, wherein the at least one lactam-containing moiety is attached to at least one end of the polymer backbone.

### Claim 3 (depends on 2)

The lactam-functionalized polymer of claim 2, wherein the at least one lactam-containing moiety has a general formula (I):
wherein R is a substituted or unsubstituted hydrocarbon diradical optionally having at least one heteroatom and is attached to a carbon or nitrogen atom on the lactam ring, and b is from 1 to 5.

### Claim 4 (depends on 3)

The lactam-functionalized polymer of claim 3, wherein R is selected from the group consisting of a substituted or unsubstituted alkylene, alkenyl, aryl, alkylaryl, arylalkylene, arylalkenyl, cyclic, cycloaliphatic and polycyclic, optionally having at least one heteroatom.

### Claim 5 (depends on 4)

The lactam-functionalized polymer of claim 4, wherein R is an alkylene having 1 to 30 carbon atoms, optionally having at least one heteroatom.

### Claim 6 (depends on 3)

The lactam-functionalized polymer of claim 3, wherein the at least one lactam-containing moiety has one or both of the following general formulas:
wherein L is a direct bond, or a substituted or unsubstituted alkylene optionally having at least one heteroatom; A is hydrogen, OXnH, SXnH, or NR4XnH; R1- R4 are identical or different and are each independently hydrogen, linear or branched alkyl having 1 to 30 carbons, or saturated or unsaturated hydrocarbon rings having 3 to 10 carbons, optionally having at least one heteroatom; X is the lactam-containing moiety of Formula (III) or (IV); n is from 0 to 500; ; and b is from 1 to 5.

### Claim 7 (depends on 2)

The lactam-functionalized polymer of claim 2, wherein the at least one lactam-containing moiety has a general formula (II):
wherein R′ and R″ are identical or different and are each independently hydrogen or a substituted or unsubstituted hydrocarbon diradical optionally having at least one heteroatom, and R″ is attached to a carbon atom on the lactam ring, and b is from 1 to 5 with the proviso that R′ or R″ or both R′ and R″ are a substituted or unsubstituted hydrocarbon diradical optionally having at least one heteroatom.

### Claim 8 (depends on 7)

The lactam-functionalized polymer of claim 7, wherein R′ and R″ are identical or different and are each independently selected from the group consisting of a substituted or unsubstituted alkylene, alkenyl, aryl, alkylaryl, arylalkylene, arylalkenyl, cyclic, cycloaliphatic and polycyclic, optionally having at least one heteroatom.

### Claim 9 (depends on 8)

The lactam-functionalized polymer of claim 8, wherein R′ and R″ are identical or different and are each independently an alkylene having 1 to 30 carbon atoms, optionally having at least one heteroatom.

### Claim 10 (depends on 7)

The lactam-functionalized polymer of claim 7, wherein R′ and R″ are identical or different
and are each independently hydrogen,
wherein L is attached to the lactam ring, and is a direct bond, or a substituted or unsubstituted alkylene optionally having at least one heteroatom; A is hydrogen, OXnH, SXnH, or NR4XnH R1-R4 are identical or different and are each independently hydrogen, linear or branched alkyl having 1 to 30 carbons, or saturated or unsaturated hydrocarbon rings having 3 to 10 carbons, optionally having at least one heteroatom; X is the lactam-containing moiety of Formula (II); n is from 0 to 500; and b is from 1 to 5 with the proviso that R′ or R″ or both R′ and R″ are a substituted or unsubstituted hydrocarbon diradical optionally having at least one heteroatom.

### Claim 11 (depends on 1)

The lactam-functionalized polymer of claim 1, wherein the polymer further comprises at least one hydrophobic moiety to form a hydrophobically modified lactam-functionalized polymer.

### Claim 12 (depends on 11)

The lactam-functionalized polymer of claim 11, wherein the hydrophobically modified lactam-functionalized polymer comprises at least one hydrophobic moiety attached to at least one end of the lactam-functionalized polymer.

### Claim 13 (depends on 12)

The lactam-functionalized polymer of claim 12, wherein the at least one hydrophobic moiety is selected from the group consisting of substituted or unsubstituted alkyl, alkenyl, aryl, alkylaryl, arylalkyl, arylalkenyl, cyclic, cycloaliphatic, and polycyclic, optionally having at least one heteroatom.

### Claim 14 (depends on 11)

The lactam-functionalized polymer of claim 11, wherein the number of the at least one hydrophobic moiety is from 1 to 500.

### Claim 15 (depends on 1)

The lactam-functionalized polymer of claim 1, wherein the number of the at least one lactam-containing moiety is from 1 to 500.

### Claim 16

A method for preparing a lactam-functionalized polymer comprising:
1) reacting a hydroxyl polyether or hydroxyl polyetheramine with a gem-dihalide to form a polymer backbone; and
2) reacting the polymer backbone with at least one compound comprising at least one lactam moiety to form the lactam-functionalized polymer.

### Claim 17 (depends on 16)

The method of claim 16, wherein the at least one compound further comprises at least one reactive functional group.

### Claim 18 (depends on 17)

The method of claim 17, wherein the at least one compound has a general formula (V):
where Y is Cl, Br, I, F, OH, SH, or NR7R8; R5and R6are identical or different and are each independently hydrogen, Cl, Br, I, F, OH, SH, NR7R8, linear or branched alkyl having 1 to 30 carbons, or saturated or unsaturated hydrocarbon rings having 3 to 10 carbons, optionally having at least one heteroatom; R7 and R8 are identical or different and are each independently hydrogen, linear or branched alkyl having 1 to 30 carbons, or saturated or unsaturated hydrocarbon rings having 3 to 10 carbons, optionally having at least one heteroatom; a is from 1 to 20; and b is from 1 to 5.

### Claim 19 (depends on 17)

The method of claim 17, wherein the at least one compound has a general formula (VII):
wherein Y is O, S, or NR7Z is O, S, or NR7; R5 and R6 are identical or different and are each independently hydrogen, Cl, Br, I, F, OH, SH, NR7R8, linear or branched alkyl having 1 to 30 carbons, or saturated or unsaturated hydrocarbon rings having 3 to 10 carbons, optionally having at least one heteroatom; R7 and R8 are identical or different and are each independently hydrogen, linear or branched alkyl having 1 to 30 carbons, or saturated or unsaturated hydrocarbon rings having 3 to 10 carbons, optionally having at least one heteroatom; a is from 1 to 20; and b is from 1 to 5.

### Claim 20 (depends on 16)

The method of claim 16, wherein the lactam-functionalized polymer further reacts with at least one compound comprising at least one hydrophobic moiety.