Recycling of acid-superbase conjugate ionic liquids by water removal in the lyocell spinning process

Patent metadata

Field	Value
Publication number	US-12509801-B2
Application number	US-202117926645-A
Country	US
Kind code	B2
Filing date	May 19, 2021
Priority date	May 19, 2020
Publication date	Dec 30, 2025
Grant date	Dec 30, 2025

Abstract

According to an example aspect of the present invention, there is provided a process for the production of a cellulose filaments or films, comprising the steps of dissolving a cellulose substrate in an ionic liquid consisting of the superbase cation 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-enium [mTBDH]+ and an anion to produce a solution forming a spinning dope, said anion being derived from an acid which is present at a stoichiometric excess to the superbase, extruding the spinning dope through a spinneret in a coagulation bath containing water to form filaments or films from the solution, withdrawing ionic liquid in an aqueous mixture with water from the coagulation bath, recovering the ionic liquid [mTBDH][OAc] from the aqueous mixture by removing water and optionally recycling the recovered ionic liquid to the dissolution step.

First claim

The invention claimed is:

1 . A process for the production of cellulose fibers, filaments, or a film, the process comprising:
preparing an ionic liquid by combining acetic acid as a source of acetate anion and 7-methyl-1,5,7-triazabicyclo [4.4.0]dec-5-enium ([mTBDH]+) as a superbase cation in a 10 to 20 mole % stoichiometric excess of the acetic acid to the [mTBDH]+ in the ionic liquid, wherein the prepared ionic liquid consists of [mTBDH]+ and acetate; dissolving a cellulose substrate in the ionic liquid to produce a spinning dope; extruding the spinning dope through a spinneret in a coagulation bath containing water to form the cellulose fibers, filaments or a film from the spinning dope; withdrawing the ionic liquid in an aqueous mixture with water from the coagulation bath; recovering the ionic liquid from the aqueous mixture by removing the water; and optionally recycling the recovered ionic liquid to the dissolving step.

2 . The process according to claim 1 , further comprising washing the cellulose fibers, filaments a film obtained from the coagulation bath with water and withdrawing further ionic liquid in an aqueous mixture with water from said washing step.

3 . The process according to claim 2 , comprising washing the cellulose fibers, filaments, or a film in the washing step with water at an ionic liquid concentration of 40 wt % or less.

4 . The process according to claim 2 , wherein the aqueous mixture withdrawn from the coagulation bath or from the washing step contains 40 wt % or less of ionic liquid.

5 . The process according to claim 1 , wherein the cellulose substrate comprises one or more of a paper pulp, a dissolving pulp, recycled cellulosic textile waste, recycled wastepaper, or a bleached dissolving pulp.

6 . The process according to claim 1 , wherein the spinning dope comprises 1,5,7-triazabicyclo [4.4.0]dec-5-ene (TBD) as an impurity in an amount up to 30 wt %.

7 . The process according to claim 6 , wherein the spinning dope comprises 1,5,7-triazabicyclo [4.4.0]dec-5-ene (TBD) as an impurity in an amount of from 10 to 30 wt %.

8 . The process according to claim 1 , wherein the spinning dope comprises water as an impurity in an amount of up to 7.5 wt %.

9 . The process according to claim 1 , wherein the recovered ionic liquid comprises one or more hydrolysis products selected from the group consisting of 1-[3-(methylammonium) propyl]-1,3-diazinan-2-one acetate ([H-mTBDH-1] [OAc]) and 1-(3-ammoniopropyl)-3-methyl-1,3-diazinan-2-one acetate ([H-mTBDH-2] [OAc]), wherein the hydrolysis products are present in an amount of ≤20 wt %, calculated from the weight of the recovered ionic liquid.

10 . The process according to claim 1 , wherein the ionic liquid is recycled by removing water from the aqueous mixture of the ionic liquid in a series of water-removal steps.

11 . The process according to claim 1 , wherein water is removed from the aqueous mixture by one or more evaporators selected from the group consisting of falling film evaporators, thin film evaporators, vapor recompression evaporators, and combinations thereof.

12 . The process according to claim 11 , wherein water is removed from the aqueous mixture in one or more evaporation plants comprising two or more evaporators selected from the group consisting of falling film evaporators, thin film evaporators, vapor recompression evaporators, and combinations thereof.

13 . The process according to claim 1 , wherein the amount of water present in the recovered ionic liquid is ≤7.5 wt %, calculated from the total weight of the recovered ionic liquid and the water.

14 . The process according to claim 1 , wherein the coagulation bath comprises the ionic liquid in a concentration of 40 wt % or less.

15 . The process according to claim 1 , comprising producing a cellulose fiber having a dry tenacity ≥35 cN/tex, a wet-to-dry tenacity of >0.80, and a modulus of toughness of ≥50 MPa.

16 . The process according to claim 1 , wherein the extruding step produces textile fibers.

Assignees

• Aalto Univ Foundation Sr

Inventors

• Sixta Herbert
• Elsayed Sherif
• Schlapp-Hackl Inge
• Witos Joanna
• Hellsten Sanna
• Uusi-Kyyny Petri
• Hummel Michael
• Alopaeus Ville

Classifications

• D01F13/00

  Recovery of starting material, waste material or solvents during the manufacture of artificial filaments or the like · CPC title

• Y02P70/62

  related technologies for production or treatment of textile or flexible materials or products thereof, including footwear · CPC title

• D01F13/02

  of cellulose, cellulose derivatives or proteins {(recovery of sodium sulfate from coagulation baths C01D5/006)} · CPC title

• D01F2/02 Primary

  from solutions of cellulose in acids, bases or salts · CPC title