IP Library Granted Patent US 10,370,482
Granted Patent B2
US 10,370,482 · App. 15/636,991 · Granted Aug 6, 2019

Lactam-functionalized polymer, compositions and applications thereof

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Quick Facts
Patent No.
US 10,370,482
App. No.
15/636,991
Granted
Aug 6, 2019
Kind
B2
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 (30)

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.

2. 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.

3. 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.

4. 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.

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

6. 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, OX n H, SX n H, or NR 4 X n H; R 1 - R 4 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.

7. 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.

8. 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.

9. 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.

10. 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, OX n H, SX n H, or NR 4 X n H R 1 -R 4 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.

11. 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.

12. 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.

13. 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.

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

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

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.

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

18. 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 NR 7 R 8 ; R 5 and R 6 are identical or different and are each independently hydrogen, Cl, Br, I, F, OH, SH, NR 7 R 8 , 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; R 7 and R 8 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.

19. The method of claim 17 , wherein the at least one compound has a general formula (VII):

wherein Y is O, S, or NR 7 Z is O, S, or NR 7 ; R 5 and R 6 are identical or different and are each independently hydrogen, Cl, Br, I, F, OH, SH, NR 7 R 8 , 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; R 7 and R 8 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.

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

Assignments (5)
RELEASE OF SECURITY INTEREST Recorded Jan 10, 2020
From: THE BANK OF NOVA SCOTIA
To: HERCULES LLC; ISP INVESTMENTS LLC
Reel/Frame 051561/0676 →
SUPPLEMENTAL SECURITY AGREEMENT Recorded May 24, 2019
From: HERCULES LLC; ISP INVESTMENTS LLC
To: THE BANK OF NOVA SCOTIA
Reel/Frame 049286/0434 →
CHANGE OF NAME Recorded Jul 12, 2017
From: HERCULES INCORPORATED
To: HERCULES LLC
Reel/Frame 043166/0044 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 29, 2017
From: BRUSH, KELLY A.; BRUGEL, TODD A.
To: HERCULES INCORPORATED
Reel/Frame 042863/0617 →
CHANGE OF NAME Recorded Jun 29, 2017
From: HERCULES INCORPORATED
To: HERCULES LLC
Reel/Frame 043040/0226 →