Polyvinyl butyral-g-polylactide copolymer

Patent metadata

Field	Value
Publication number	US-10669357-B2
Application number	US-201615754853-A
Country	US
Kind code	B2
Filing date	Aug 22, 2016
Priority date	Aug 27, 2015
Publication date	Jun 2, 2020
Grant date	Jun 2, 2020

Abstract

Copolymers of a polyvinyl butyral backbone with polylactic acid grafts and their compounds are disclosed, which can be used to produce clear, flexible and ductile bio-based films. The copolymers are amorphous and have been shown to maintain clarity, flexibility, and ductility after continuous exposure to thermal aging at 80° C. for one week.

First claim

What is claimed is:

1. A copolymer of polyvinyl butyral-g-polylactide, wherein the copolymer is a reaction product of the polyvinyl butyral and lactide monomer polymerized to form polylactide in the presence of a catalyst, and wherein the weight ratio of polyvinyl butyral to polylactide ranges from about 1:18 to about 4:1.

2. The copolymer of claim 1 , wherein the copolymer comprises random repeating units of:

wherein x ranges from about 250 to about 2000; wherein y′+z′ ranges from about 100 to about 1200; wherein w ranges from 0 to about 100, and wherein n ranges from about 2 to about 10.

3. The copolymer of claim 1 , wherein the copolymer is a branched polymer of a backbone of the polyvinyl butyral and grafts of the polylactic acid, and wherein the polylactic acid has from 3 to about 4 mer units of lactide monomer.

4. The copolymer of claim 1 , wherein the polylactic acid has been polymerized from a selection of lactide monomers consisting of L-lactide, D-lactide, Meso-lactide, or any combination thereof.

5. The copolymer of claim 3 , wherein the copolymer is a comb polymer of a backbone of the polyvinyl butyral and grafts of the polylactide of consistent length of about 3 to about 4 mer units of lactide per graft to vinyl alcohol sites of the polyvinyl butyral.

6. A thermoplastic compound, comprising the copolymer of claim 1 , wherein the copolymer is an in-situ reaction product of polyvinyl butyral and lactide monomer polymerized on a backbone of the polyvinyl butyral to form grafts of polylactic acid in presence of a catalyst, optionally plasticizer, and optionally chain extender.

7. The compound of claim 6 , wherein the compound comprises from about 25 to about 99 weight percent of the copolymer and from about 0 to about 50 weight percent of the plasticizer.

8. The compound of claim 6 , wherein the copolymer is a reaction product of the polyvinyl butyral and the lactide monomer polymerized to form polylactide in the absence of plasticizer.

9. The compound of claim 6 , wherein the copolymer in the compound has no discernible melting temperature (T m ) as measured by ASTM D3418 at heating/cooling rates of 20° C./minute.

10. The compound of claim 6 , wherein the copolymer in the compound has a glass transition temperature (T g ) of between about 11° C. and about 46° C. as measured by ASTM D7426 at heating/cooling rates of 20° C./minute.

11. The compound of claim 6 , wherein the compound comprises from about 45 to about 95 weight percent of the copolymer, and from about 0 to about 40 weight percent of plasticizer.

12. The compound of claim 6 , wherein the polyvinyl butyral to lactide monomer weight ratio in the copolymer ranges from about 1:18 to about 4:1.

13. The compound of claim 6 , wherein the copolymer in the compound has no discernible melting temperature (T m ) following extrusion and after 7 days of exposure to a temperature of 80° C. as measured by ASTM D3418 at heating/cooling rates of 20° C./minute.

14. The compound of claim 6 , wherein the copolymer is a reaction product of the polyvinyl butyral and the lactide monomer polymerized to form polylactide in the presence of the chain extender epoxy-functional styrene-acrylate oligomer, and wherein tear resistance of the compound is greater than about 350 lbf/in as measured using ASTM D624.

15. The compound of claim 6 , further comprising one or more functional additives selected from the group consisting of adhesion promoters; biocides; antibacterials; fungicides; mildewcides; anti-fogging agents; anti-static agents; bonding, blowing and foaming agents; dispersants; fillers and extenders; fire and flame retardants and smoke suppressants; impact modifiers; initiators; lubricants; micas; pigments, colorants and dyes; plasticizers; processing aids; release agents; silanes, titanates and zirconates; slip and anti-blocking agents; stabilizers; stearates; ultraviolet light absorbers; viscosity regulators; waxes; branching agents, and combinations of them.

16. A plastic article of the compound of claim 6 .

17. The plastic article of claim 16 , in a shape selected from the group consisting of film, sheet, pellet, fiber, molded part, extruded part, 3D printed part, and thermoformed part.

18. A method of making the copolymer of claim 1 , comprising the step of in-situ polymerization of lactide monomer in presence of a catalyst and vinyl alcohol sites of polyvinyl butyral, wherein the catalyst drives polymerization of the lactide monomer to form polylactide grafts and transesterification between hydroxyl groups on the polyvinyl butyral with ester groups on the lactide monomer.

Assignees

• Polyone Corp

Inventors

• Duan Yannan
• Avakian Roger W

Classifications

• C08J2329/14

  Homopolymers or copolymers of acetals or ketals obtained by polymerisation of unsaturated acetals or ketals or by after-treatment of polymers of unsaturated alcohols · CPC title

• C08J5/18

  Manufacture of films or sheets · CPC title

• C08G63/08

  Lactones or lactides · CPC title

• C08F216/34 Primary

  by an aldehydo radical · CPC title

• C08F8/28

  Condensation with aldehydes or ketones · CPC title