Method for producing formaldehyde-alkyl carbonate-copolymers

Patent metadata

Field	Value
Publication number	US-10030100-B2
Application number	US-201415103329-A
Country	US
Kind code	B2
Filing date	Dec 5, 2014
Priority date	Dec 10, 2013
Publication date	Jul 24, 2018
Grant date	Jul 24, 2018

Abstract

The present invention relates to a method for producing formaldehyde-alkylene carbonate copolymers comprising the step of reacting trimeric, oligomeric and/or polymeric formaldehyde with an alkylene carbonate in the presence of a catalyst. Said invention further relates to copolymers obtainable by this method and the reaction products thereof with polyisocyanates.

First claim

The invention claimed is:

1. A method for producing formaldehyde-alkylene carbonate copolymers comprising the step of reacting trimeric, oligomeric and/or polymeric formaldehyde with an alkylene carbonate in the presence of a catalyst,
wherein
the reaction is carried out under pressurization with CO 2 .

2. The method as claimed in claim 1 , wherein the pressurization with CO 2 is carried out such that a CO 2 partial pressure of ≥15 bar is attained.

3. The method as claimed in claim 1 , wherein:
the catalyst comprises a metal M in an, oxidation state of ≥III, wherein M is selected from the consisting of group of B, Sc, Y, Ti, Zr, Hf and/or a lanthanide;
and/or
the catalyst comprises tin in an oxidation state of ≥II.

4. The method as claimed in claim 1 , wherein said formaldehyde comprises 1,3,5-trioxane.

5. The method as claimed in claim 1 , wherein the alkylene carbonate corresponds to the following formula:

wherein R 1 and R 2 are independently of one another selected from the group of hydrogen, linear C 1 - to C 16 -alkyl, C 3 - to C 16 -cycloalkyl, C 2 - to C 16 -alkenyl and aryl.

6. The method as claimed in claim 5 , wherein the alkylene carbonate is ethylene carbonate, propylene carbonate and/or butylene carbonate.

7. The method as claimed in claim 1 , wherein the catalyst comprises one or more of BF 3 .OEt 2 , TiCl 4 , ZrCl 4 , YbCl 3 and SnCl 2 .

8. The method as claimed in claim 1 , wherein the reaction is carried out at a temperature of ≥80° C. to ≤150° C.

9. The method as claimed in claim 8 , wherein said catalyst is added only once a predetermined temperature has been attained.

10. The method as claimed in claim 1 , further comprising the step of reacting the resultant copolymer with an OH-reactive compound.

11. The method as claimed in claim 10 , wherein the OH-reactive compound is selected from the group of anhydrides and/or of alkylene oxides.

12. The method as claimed in claim 10 , wherein the OH-reactive compound is selected from the group of polyisocyanates.

13. A formaldehyde-alkylene carbonate copolymer which comprises the reaction product obtained by reacting (i) trimeric, oligomeric and/or polymeric formaldehyde, with (ii) an alkylene carbonate, in the presence of (iii) a catalyst, and (iv) under pressurization with carbon dioxide, wherein the resultant formaldehyde-alkylene carbonate copolymer has a reflection in the infrared spectrum at 1735 cm −1 ±5 cm −1 of ≤86%.

14. A polyurethane polymer obtained by a method as claimed in claim 12 .

15. The copolymer as claimed in claim 13 , wherein said copolymer has a CO 2 content of ≥3.0 wt % to ≤33 wt %.

16. The formaldehyde-alkylene carbonate copolymer of claim 13 , wherein (i) said formaldehyde comprises 1,3,5-trioxane, (ii) said alkylene carbonate comprises cyclic propylene carbonate, and (iii) said catalyst comprises one or more of BF 3 .OEt 2 , TiCl 4 , ZrCl 4 , YbCl 3 and SnCl 2 .

Assignees

• Covestro Deutschland Ag

Inventors

• Wolf Aurel
• Peckermann Ilja
• Langanke Jens

Classifications

• C08L59/00

  Compositions of polyacetals; Compositions of derivatives of polyacetals (of polyvinyl acetals C08L29/14) · CPC title

• C08G18/44

  Polycarbonates · CPC title

• C08G18/72

  Polyisocyanates or polyisothiocyanates · CPC title

• C08G2/00 Primary

  Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances · CPC title

• C08G18/08

  Processes · CPC title