Recovery of fibers from fiber reinforced polymers with Lewis bases

Patent metadata

Field	Value
Publication number	US-11208345-B2
Application number	US-202016845494-A
Country	US
Kind code	B2
Filing date	Apr 10, 2020
Priority date	Sep 29, 2016
Publication date	Dec 28, 2021
Grant date	Dec 28, 2021

Abstract

A composition comprising a Lewis base containing depolymerization liquid and methods of using the Lewis base depolymerization liquid to depolymerize the polymer component of fiber reinforced polymers to form free fibers.

First claim

What is claimed is:

1. A depolymerization mixture comprising a Lewis base having a boiling point of at least 150° C. at one atmosphere that resists ionization into cations and anions and a fiber reinforced polymer, wherein the Lewis base is triphenylphosphine oxide, triphenylphosphine sulfide, triphenylphosphine, 4-(dimethylamino)phenyldiphenylphosphine, triphenylphosphine selenide, tributyl phosphine oxide, tris(2-ethylhexyl)phosphine oxide, phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, trioctylphosphine oxide, triethylphosphine oxide, diphenylphosphine oxide, methyldiphenylphosphine oxide, Lawesson's reagent, or a mixture thereof, each of which is optionally substituted with one or more substituents selected from halogen, nitrate, sulfonic acid, alkyl, alkenyl, phenyl and aldehyde.

2. The depolymerization mixture of claim 1 further comprising partially decomposed polymer.

3. The depolymerization mixture of claim 2 wherein the Lewis base is triphenylphosphine oxide, triphenylphosphine sulfide, triphenylphosphine, 4-(dimethylamino)phenyldiphenylphosphine, triphenylphosphine selenide, tributyl phosphine oxide, tris(2-ethylhexyl)phosphine oxide, phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, trioctylphosphine oxide, triethylphosphine oxide, diphenylphosphine oxide, methyldiphenylphosphine oxide, Lawesson's reagent, or a mixture thereof.

4. The depolymerization mixture of claim 1 further comprising free fibers.

5. A depolymerization composition having a temperature of at least 200° C. and comprising a Lewis base having a boiling point of at least 150° C. at one atmosphere and a fiber reinforced polymer, wherein the Lewis base is triphenylphosphine oxide, triphenylphosphine sulfide, triphenylphosphine, 4-(dimethylamino)phenyldiphenylphosphine, triphenylphosphine selenide, tributyl phosphine oxide, tris(2-ethylhexyl)phosphine oxide, phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, trioctylphosphine oxide, triethylphosphine oxide, diphenylphosphine oxide, methyldiphenylphosphine oxide, Lawesson's reagent, or a mixture thereof, each of which is optionally substituted with one or more substituents selected from halogen, nitrate, sulfonic acid, alkyl, alkenyl, phenyl and aldehyde.

6. The depolymerization composition of claim 5 wherein the Lewis base is triphenylphosphine oxide, triphenylphosphine sulfide, triphenylphosphine, 4-(dimethylamino)phenyldiphenylphosphine, triphenylphosphine selenide, tributylphosphine oxide, tris(2-ethylhexyl)phosphine oxide, phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, trioctylphosphine oxide, triethylphosphine oxide, diphenylphosphine oxide, methyldiphenylphosphine oxide, or Lawesson's reagent.

7. The depolymerization composition of claim 5 further comprising free fibers.

8. The depolymerization composition of claim 7 wherein the free fibers are carbon fibers.

9. The depolymerization composition of claim 7 wherein the fiber reinforced polymer is a fiber reinforced thermoset polymer.

10. The depolymerization composition of claim 7 wherein the fiber reinforced polymer is an epoxy based polymer.

11. The depolymerization composition of claim 7 wherein the Lewis base is triphenylphosphine oxide, triphenylphosphine sulfide, triphenylphosphine, 4-(dimethylamino)phenyldiphenylphosphine, triphenylphosphine selenide, tributylphosphine oxide, tris(2-ethylhexyl)phosphine oxide, phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, trioctylphosphine oxide, triethylphosphine oxide, diphenylphosphine oxide, or Lawesson's reagent.

12. The depolymerization composition of claim 5 wherein the Lewis base is triphenylphosphine sulfide or triphenylphosphine selenide.

13. The depolymerization composition of claim 5 wherein the Lewis base is triphenylphosphine oxide.

14. The depolymerization liquid of composition 10 which is at a temperature of at least 325° C.

15. The depolymerization mixture of claim 2 wherein the Lewis base is triphenylphosphine oxide, triphenylphosphine sulfide, triphenylphosphine, 4-(dimethylamino)phenyldiphenylphosphine, triphenylphosphine selenide, tributylphosphine oxide, tris(2-ethylhexyl)phosphine oxide, phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, trioctylphosphine oxide, triethylphosphine oxide, diphenylphosphine oxide, or Lawesson's reagent.

16. The depolymerization mixture of claim 2 wherein the Lewis base is triphenylphosphine oxide, triphenylphosphine sulfide, triphenylphosphine, 4-(dimethylamino)phenyldiphenylphosphine, or triphenylphosphine selenide.

17. The depolymerization mixture of claim 2 wherein the Lewis base is tributylphosphine oxide, tris(2-ethylhexyl)phosphine oxide, phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, trioctylphosphine oxide, triethylphosphine oxide, or diphenylphosphine oxide.

18. The depolymerization mixture of claim 2 wherein the Lewis base is Lawesson's reagent.

19. The depolymerization mixture of claim 2 wherein the Lewis base is triphenylphosphine sulfide or triphenylphosphine selenide.

20. The depolymerization mixture of claim 2 wherein the Lewis base is triphenylphosphine oxide.

Assignees

• Boeing Co

Inventors

• Gross Adam F
• Rodriguez April R
• Nelson Ashley M
• Vajo John J
• Dalal Hardik
• George Panagiotis Emanuel
• Guan Xin N
• Davis Jr James Hillard

Classifications

• C08J11/26 Primary

  containing carboxylic acid groups, their anhydrides or esters · CPC title

• C08J2300/30

  Polymeric waste or recycled polymer · CPC title

• C03C13/00 Primary

  Fibre or filament compositions (manufacture of fibres or filaments C03B37/00) · CPC title

• C01B32/05

  Preparation or purification of carbon not covered by groups C01B32/15, C01B32/20, C01B32/25, C01B32/30 · CPC title

• C08J11/00 Primary

  Recovery or working-up of waste materials (recovery of plastics B29B17/00; polymerisation processes involving purification or recycling of waste polymers or their depolymerisation products C08B, C08C, C08F, C08G, C08H) · CPC title