Carbon fiber recovery compositions and methods

Patent metadata

Field	Value
Publication number	US-10611892-B2
Application number	US-201715482012-A
Country	US
Kind code	B2
Filing date	Apr 7, 2017
Priority date	Apr 7, 2017
Publication date	Apr 7, 2020
Grant date	Apr 7, 2020

Abstract

Methods and compositions for depolymerizing the polymer component of fiber reinforced polymers to facilitate the recovery of free fibers.

First claim

What is claimed is:

1. A method for recovering free fibers from a fiber reinforced polymer comprising:
admixing the fiber reinforced polymer with a depolymerization composition comprising an ionic salt and a protective compound that protects the ionic salt from degradation to form a recycle admixture; and
heating the recycle admixture to a processing temperature at which the protective compound is molten and at which the ionic salt dissolves in the protective compound and maintaining the recycle admixture at the processing temperature for a period of time sufficient to at least partially depolymerize a portion of the fiber reinforced polymer to yield free fiber and decomposed polymer.

2. The method of claim 1 wherein the ionic salt is liquid in the depolymerization composition at a temperature below 200° C.

3. The method of claim 1 wherein the ionic salt contains at least one of C, H, N, and P.

4. The method of claim 1 wherein the ionic salt includes one or more of a phosphonium ion, ammonium ion, hexafluorophosphate ion, imidazolium ion, pyrrolidinium ion, pyridinium ion, imide on, sulfonate ion, and a trifluoromethane sulfonyl imide (TFSI) ion.

5. The method of claim 1 wherein the ionic salt includes a phosphonium ion.

6. The method of claim 1 wherein the ionic salt includes at least one phenyl group.

7. The method of claim 1 wherein the ionic salt is one or more of 3-[2-(4-nitro-phenyl)-2-oxoethyl]-1-methylimidazolium (C 12 H 14 N 3 O 2 ); 3-[2-(3-chlorophenyl)-2-oxoethyl]-1-methylimidazolium (C 12 H 12 ClN 2 O); 3-[2-(4-chlorophenyl)-2-oxoethyl]-1-methylimidazolium (C 12 H 12 ClN 2 O); 1-ethyloxy-3-[4-nitrobenzyl] imidazolium (C 12 H 14 N 3 O 3 ); 1-methyloxy-3-[2-(4-chlorophenyl)-2-oxoethyl]imidazolium (C 12 H 12 ClN 2 O 2 ); 3-[2-(4-nitro-phenyl)-2-oxoethyl]-1-methylimidazolium (C 12 H 12 NO 3 ); 1-etheneoxy-3-[2,4-dichlorobenzyl] imidazolium (C 12 H 11 Cl 2 N 2 O); 1-ethyloxy-3-[2,4-dichlorobenzyl] imidazolium (C 12 H 13 C 12 N 2 O); 3-[2-(3,4-dichlorophenyl)-2-oxoethyl]-1-methylimidazolium (C 12 H 11 Cl 2 N 2 O); 1-hydrocinnamyl-3-methyl imidazolium (C 13 H 17 N 2 ); 1-nonyl-3-methylimidazolium (C 13 H 25 N 2 ); I-octyl-3-ethylimidazolium (C 13 H 25 N 2 ); 1,3-di-(1-butoxymethyl)-imidazolium (C 13 H 25 N 2 O 2 ); 1-Methyl-3-(2-oxo-2-o-tolyl-ethyl)-imidazolium (C 13 H 15 N 2 O); 1-(4-methoxynbutyl)-3-methylimidazolium (C 9 H 17 N 2 O); 1-[2-(2-methoxyethoxy)ethyl]-3-methyl imidazolium (C 9 H 17 N 2 O 2 ); 1,3-dibenzylimidazolium (C 10 H 10 N 2 ); 1-hexyl-3-methylimidazolium (C 10 H 19 N 2 ); 1-[2-phenyl-2-oxyethyl]-3-methyl imidazolium (C 10 H 11 N 2 O); 1-(3-cyano-propyl)-3-(2-cyano-ethyl)imidazolium (C 10 H 13 N 4 ); 1-(2-furan-2-yl-2-oxo-ethyl)-3-methylimidazolium (C 10 H 11 N 2 O 2 ); 1-hydroxy-3-[2,4-dichlorobenzyl]imidazolium (C 10 H 9 C 12 N 2 O); 1-benzyl-3-methylimidazolium (C 11 H 13 N 2 ); 1-benzyl-3-methylimidazolium (C 11 H 13 N 2 ); 1-heptyl-3-methylimidazolium (C 11 H 21 N 2 ); 1-hexyl-3-ethylimidazolium (C 11 H 21 N 2 ), 1,3-dibutylimidazolium (C 11 H 21 N 2 ), 1-(4-methoxyphenyl)-3-methylimidazolium (C 11 H 13 ON 2 ); phenyl-3-methylimidazolium (C 12 H 15 N 2 ); 1-methyl-3-(3-methyl-benzyl)-imidazolium (C 12 H 15 N 2 ); 1-methyl-3-(2-methyl-benzyl)-imidazolium (C 12 H 15 N 2 ); 3-[2-(4-bromo-phenyl)-2-oxoethyl]-1-methyl imidazolium (C 12 H 12 BrN 2 O); 1-octyl-3-methylimidazolium (C 12 H 23 N 2 ); phenylethanoyl-3-propylimidazolium (C 12 H 15 N 2 O); heptoxymethyl-3-methylimidazolium (C 12 H 23 N 2 O); 3-[2-(2-florophenyl)-2-oxoethyl]-1-methyl imidazolium (C 12 H 12 FN 2 O); 11-(1-propoxymethyl)-3-(1-butoxymethyl) imidazolium (C 12 H 23 N 2 O 2 ); 3-(4-Cyano-benzoyl)-1-methyl imidazolium (C 13 H 12 N 3 O); 3-[2-(4-methyloxyphenyl)-2-oxoethyl]-1-methyl imidazolium (C 13 H 15 N 2 O 2 ); 3-[2-(2-methyloxyphenyl)-2-oxoethyl]-1-methylimidazolium (C 13 H 15 N 2 O 2 ); 1-ethyloxy-3-[2-(4-chlorophenyl)-2-oxoethyl]imidazolium (C 13 H 14 ClN 2 O 2 ); 1-hydroxy-3-(3,4,5-trimethyloxybenzyl)imidazolium (C 13 H 17 N 2 O 4 ); 1-ethyl-3-[2-(4-bromo-phenyl)-2-oxoethyl]imidazolium (C 13 H 14 BrN 2 O); 1-methyl-3-[2,6-(S)-dimethylocten-2-yl]imidazolium (C 14 H 25 N 2 ); 1-octyl-3-propylimidazolium (C 14 H 27 N 2 ); 1-decyl-3-methylimidazolium (C 14 H 27 N 2 ); 3-[2-(1,2-dimethyloxyphenyl)-2-oxoethyl]-1-methylimidazolium (C 14 H 17 N 2 O); 3-(1,1-dimethyl-2-phenyl-2-oxoethyl)-1-methylimidazolium (C 14 H 17 N 2 O); 3-[2-(3,5-dimethoxylphenyl)-2-oxoethyl]-1-methylimidazolium (C 14 H 17 N 2 O 3 ); 3-[2-(3,4-dimethyloxyphenyl)-2-oxoethyl]-1-methylimidazolium (C 14 H 17 N 2 O); 1-(1-nonoxymethyl)-3-methylimidazolium (C 14 H 27 N 2 O); 3-[2-(3-ethoxylphenyl)-2-oxoethyl]-1-methylimidazolium (C 14 H 17 N 2 O 2 ); 3-[2-(4-ethoxylphenyl)-2-oxoethyl]-1-methylimidazolium (C 14 H 17 N 2 O 2 ); 1-(1-amyloxymethyl)-3-butoxymethyl imidazolium (C 14 H 17 N 2 O 2 ); 1-amyl-3-benzylimidazolium (C 15 H 21 N 2 ); 1-(1-hexyloxymethyl)-3-(1-butoxymethyl) imidazolium (C 15 H 29 N 2 O 2 ); 1-undecyl-3-methylimidazolium (C 15 H 29 N 2 ); 1-(1-decyloxymethyl)-3-methylimidazolium (C 15 H 29 N 2 O); 3-[2-(3-propyloxylphenyl)-2-oxoethyl]-1-methyl imidazolium (C 15 H 19 N 2 O 2 ); 3-[2-(3-methyloxylphenyl)-2-oxoethyl]-1-isopropylimidazolium (C 15 H 19 N 2 O 2 ); 3-[2-(2,4,6-trimethyloxyphenyl)-2-oxoethyl]-1-methylimidazolium (C 15 H 19 N 2 O 2 ); 3-[2-α-naphthyl-2-oxoethyl]-1-methylimidazolium (C 16 H 15 N 2 O); 1-(1-heptyloxymethyl)-3-(1-butoxymethyl) imidazolium) imidazolium (C 16 H 31 N 2 O 2 ); 1-dodecyl-3-methylimidazolium (C 16 H 31 N 2 ); 1-(1-undecyloxymethyl)-3-methylimidazolium (C 16 H 31 N 2 O); dimethylpropionyloxy)-3-[2-(4-chlorophenyl)-2-oxoethyl]imidazolium (C 16 H 18 ClN 2 O 3 ); 1-(1-dodecyloxymethyl)-3-methylimidazolium (C 17 H 33 N 2 O); 1-tridecyl-3-methylimidazolium (C 17 H 33 N 2 ); 1-benzyloxy-3-(2,4-dichlorobenzyl)imidazolium (C 17 H 15 C 12 N 2 O); 1-(4-benzoyl-benzyl)-3-methyl-imidazolium (C 18 H 17 N 2 O); 1-tetradecyl-3-methylimidazolium (C 18 H 35 N 2 ); 3-[2-(3-methyloxylphenyl)-2-oxoethyl]-1-phenylimidazolium (C 18 H 17 N 2 O 2 ); 1-(1-nonyloxymethyl)-3-(1-butoxymethyl)imidazolium (C 18 H 35 N 2 O 2 ); 1-(2-phenylethyloxy)-3-(2,5-dichlorobenzyl)imidazolium (C 18 H 17 C 12 N 2 O); 1-[2,4-dichlorophenylmethyloxyl]-3-[2-(4-chlorophenyl)-2-oxoethyl]imidazolium (C 18 H 14 C 13 N 2 O); 1-pentadecyl-3-methylimidazolium (C 19 H 37 N 2 ); 1-phenyloxy-3-[2-(4-dimethylamino-phenyl)-2-oxoethyl]imidazolium (C 19 H 20 N 3 O 2 ); 1-(1-decyloxymethyl)-3-(1-butoxy methyl)imidazolium (C 19 H 37 N 2 O 2 ); 1-hexadecyl-3-methylimidazolium (C 20 H 39 N 2 ); 1-(1-decyloxymethyl)-3-hexyl imidazolium (C 20 H 39 N 2 O); 1-(1-undecyloxymethyl)-3-(1-butoxy methyl)imidazolium (C 20 H 39 N 2 O); 1-(1-undecyloxymethyl)-3-hexyl imidazolium (C 21 H 41 N 2 O); 1-octadecyl-3-methylimidazolium (C 22 H 43 N 2 ); 1-cosyl-3-methylimidazolium (C 24 H 47 N 2 ); 1-(2-(2-(2-(2-(2-(2-(2-(methacryloyloxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)-3-ethylimidazolium (C 25 H 45 O 9 N 2 ); polymer of PEOimidazolium; 3-dihydroxy-2-bromoimidazolium (C 3 H 4 BrN 2 O 2 ); 1,3-dimethyl 5 chloroimidazolium (C 5 H 8 ClN); 2,4,5-trimethylimidazolium (C 6 H 11 N 2 ); 1,2,3-trimethylimidazolium (C 6 H 11 N 2 ); 1,3-dimethyl-nimtrimleimidazolium (C 6 H 8 N 3 S); 1,2-dimethyl-3-ethylimidazolium (C 7 H 13 N 2 ); 1-ethyl-3,5-dimethylimidazolium (C 7 H 13 N 2 ); 1-ethyl-2,3-dimethylimidazolium (C 7 H 13 N 2 ), 1,3-dimethyl-4-methylimidazolium (C 8 H 15 N 2 ); 1,2-methyl-3-propylimidazolium (C 8 H 15 N 2 ); 1,2-ethyl-3-methylimidazolium (C 8 H 15 N 2 ); 1-propyl-2,3-dimethylimidazolium (C 8 H 15 N 2 ); 1-butyl-2,3-dimethylimidazolium (C 9 H 17 N 2 ); 3-butyl-1-,5-dimethylimidazolium (C 9 H 17 N 2 ); 1,3-dimethyl-2-phenylimidazolium (C 11 H 13 N 2 ); 1-benzyl-2-methyl-3-propyl (C 13 H 19 N 2 ), 1-octyl-2,3-dimethylimidazolium (C 13 H 25 N 2 ); 1,3-dipr

Assignees

• Boeing Co

Inventors

• Gross Adam F
• Vajo John J
• Nelson Ashley M
• Rodriguez April R
• Dalal Hardik
• George Panagiotis E

Classifications

• C08J11/18

  by treatment with organic material · CPC title

• C07C63/28

  Salts thereof · CPC title

• D01F9/12

  Carbon filaments; Apparatus specially adapted for the manufacture thereof · 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

• C08K7/06

  Elements · CPC title