Water-borne polyamide-urea dispersions

Patent metadata

Field	Value
Publication number	US-9988555-B2
Application number	US-201414766918-A
Country	US
Kind code	B2
Filing date	Feb 3, 2014
Priority date	Feb 13, 2013
Publication date	Jun 5, 2018
Grant date	Jun 5, 2018

Abstract

Polymers are disclosed that incorporate large portions of elastomeric polyamide oligomers connected with polyisocyanates. These polymers have enhanced properties over similar polyurethanes due to better hydrolysis resistance of polyamides over polyesters and better UV resistance of polyamides over polyethers. Polyurea linkages can also improve properties over polyurethane linkages. Composites and hybrids of these polymers and other polyamides with vinyl polymers are also disclosed and claimed.

First claim

What is claimed is:

1. A liquid telechelic prepolymer comprising the reaction product of a telechelic polyamide, a polyisocyanate, and optionally other molecules with functional groups that react with isocyanate groups; wherein the polyisocyanate is characterized by having two or more isocyanate groups, the telechelic polyamide is characterized as having repeating units connected by linkages between the repeating units and having two or more Zerewitinoff groups that chemically react with isocyanate groups to form a chemical bond between a portion of said Zerewitinoff groups and the isocyanate group, further wherein the telechelic polyamide comprises repeat units connected with chemical linkages wherein desirably at least 10% of the total number of the heteroatom containing linkages connecting hydrocarbon type linkages are characterized as being amide linkages, at least 25% of the amide linkages are characterized as being tertiary amide linkages, and said liquid telechelic prepolymer having a viscosity measured by a Brookfield circular disc viscometer with the circular disc spinning at 5 rpm of less than 100,000 cps at a temperature of 70° C.

2. The liquid telechelic prepolymer according to claim 1 , further comprising a surface active dispersing agent as part of the prepolymer or as a separate molecule dissolved in said prepolymer.

3. The liquid telechelic prepolymer according to claim 2 , wherein said surface active dispersing agent comprises a nonionic oligomer chemically bound to said prepolymer.

4. The liquid telechelic prepolymer according to claim 3 , wherein said surface active dispersing agent comprise anionic species chemically bound to said prepolymer.

5. The liquid telechelic prepolymer according to claim 3 , wherein said surface active dispersing agent comprises a cationic species chemically bound to said prepolymer.

6. The liquid telechelic prepolymer according to claim 4 , wherein said anionic species comprises a carboxylic acid group.

7. The liquid telechelic prepolymer according to claim 5 , wherein said cationic species comprises a salt of a tertiary amine or a quaternary ammonium group.

8. The liquid telechelic prepolymer according to claim 1 , wherein said telechelic polyamide is characterized by having a weight average molecular weight of less than 10,000 g/mole.

9. The liquid telechelic prepolymer according to claim 1 , further comprising a solvent.

10. The liquid telechelic prepolymer according to claim 1 , wherein said prepolymer is formed by a ratio of isocyanate groups of said polyisocyanate to Zerewitinoff groups from said telechelic polyamide and optional other molecules from 20:1 to 1:1.

11. The liquid telechelic prepolymer according to claim 1 , formed into a dispersion in an aqueous media.

12. The liquid telechelic prepolymer according to claim 2 formed into a dispersion in aqueous media, optionally chain extended into a polymer and optionally containing a second polymer, said second polymer being without polyamide segments, said second polymer optionally either blended in a dispersed phase with said colloidally stabilized telechelic prepolymer or separately dispersed in water and thereafter blended with said colloidally stabilized telechelic prepolymer dispersed in water, wherein said optional second polymer, when present, is present in an amount of at least 10 wt. % based on the total polymeric solids in the dispersion and optionally where said second polymer is added as free radically polymerizable monomer(s) and thereafter is free radically polymerized into a second polymer, wherein said free radically polymerizable monomer(s) are added to said telechelic prepolymer prior to dispersion of said prepolymer in water or said monomer(s) being added to said prepolymer after the prepolymer is formed into a dispersion.

13. The liquid telechelic prepolymer, according to claim 11 , wherein said telechelic prepolymer is chain extended and formed into a self-supporting film, a coating, or an adhesive.

14. The liquid telechelic prepolymer, according to claim 1 , wherein at least 80% of said amide linkages are characterized as tertiary amide linkages, wherein said telechelic prepolymer is characterized as the reaction product of a hydroxyl terminated polyamide with a polyisocyanate and optionally other molecules, and said telechelic polyamide is comprised of one or more repeat units from a lactone of 4 to 10 carbon atoms and/or a hydroxyl carboxylic acid of 3 to 30 carbon atoms (in one embodiment said lactone and/or hydroxyl carboxylic acid is added after polymerization of an amine terminated polyamide and reacted with said amine terminated polyamide to convert to a hydroxyl terminated polyamide by being the terminal repeat unit on one or both ends of the polyamide).

15. The liquid telechelic prepolymer, according to claim 1 , wherein at least 50 wt. % of said polyamide oligomer comprises repeat units of the structure

wherein R a is the alkylene portion of the dicarboxylic acid and is a cyclic, linear, or branched, optionally including aromatic groups alkylene of 2 to 36 carbon atoms, optionally including up to 1 heteroatom per 3 or 10 carbon atoms of the diacid, and
wherein R b is a direct bond or a linear or branched, optionally being or including cyclic, heterocyclic, or aromatic portion(s), alkylene group, optionally containing up to 1 or 3 heteroatoms per 10 carbon atoms, of 2 to 60 carbon atoms and R c and R d connect together form a single linear or branched alkylene group of 1 to 8 carbon atoms.

16. The liquid telechelic prepolymer, according to claim 1 , wherein at least 70 wt. % of said polyamide oligomer comprises repeat units of the structure

17. The liquid telechelic prepolymer, according to claim 1 , wherein at least 80 wt. % of said polyamide oligomer comprises repeat units of the structure

18. The liquid telechelic prepolymer according to claim 11 formed into a dispersion in water, wherein at least 50 wt. % of said polyamide oligomer comprises repeat units of the structure

wherein R a is the alkylene portion of the dicarboxylic acid and is a cyclic, linear, or branched, optionally including aromatic groups alkylene of 2 to 36 carbon atoms, optionally including up to 1 heteroatom per 3 or 10 carbon atoms of the diacid, and
wherein R b is a direct bond or a linear or branched, optionally being or including cyclic, heterocyclic, or aromatic portion(s), alkylene group, optionally containing up to 1 or 3 heteroatoms per 10 carbon atoms, of 2 to 60 carbon atoms and R c and R d connect together form a single linear or branched alkylene group of 1 to 8 carbon atoms.

19. The liquid telechelic prepolymer according to claim 18 formed into a dispersion in water, wherein at least 80 wt. % of said polyamide oligomer comprises repeat units of the structure

Assignees

• Lubrizol Advanced Mat Inc

Inventors

• Erdodi Gabor
• Pourahmady Naser
• Lai John Ta-Yuan
• Pajerski Anthony D

Classifications

• C08G73/0633

  with only two nitrogen atoms in the ring · CPC title

• C08G69/34

  using polymerised unsaturated fatty acids · CPC title

• C09J175/12

  from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group · CPC title

• C08G18/0823

  containing carboxylate salt groups or groups forming them · CPC title

• C08G18/603 Primary

  Polyamides · CPC title