Method for the synthesis of polymer carbodiimides with added cesium salts, polymer carbodiimides, and use thereof

Patent metadata

Field	Value
Publication number	US-10351652-B2
Application number	US-201615735295-A
Country	US
Kind code	B2
Filing date	Jun 14, 2016
Priority date	Jun 15, 2015
Publication date	Jul 16, 2019
Grant date	Jul 16, 2019

Abstract

The present invention relates to processes for producing polymeric carbodiimides by addition of cesium salts and to polymeric carbodiimides produced by this process and to the use thereof as a hydrolysis inhibitor, especially in polyurethane (PU)-based systems, preferably thermoplastic TPU, PU adhesives, PU casting resins, PU elastomers or PU foams.

First claim

What is claimed is:

1. A process for producing polymeric carbodiimides of formula (I)
R 1 —R 2 —(—N═C═N—R 2 —) m —R 1   (1),

in which:
m represents an integer from 2 to 500,
R 2 =C 1 -C 18 -alkylene, C 5 -C 18 -cycloalkylene, arylene, C 7 -C 18 alkylarylene and/or C 7 -C 18 -aralkylene, and
R 1 =—NCO, NCNR 2 , NHCONHR 4 , —NHCONHR 2 , —NHCONR 4 R 5 or —NHCOOR 6 , wherein in R 1 :
independently of one another, R 4 and R 5 are identical or different and represent a C 1 -C 6 -alkyl, C 6 -C 10 -cycloalkyl or C 7 -C 18 -aralkyl radical, and
R 6 has one of the definitions of R 1 or represents a polyester or a polyamide radical or —(CH 2 ) h —O—[(CH 2 ) k —O] g —R 7 , where:
h=1-3, k=1-3, g=0-12; and
R 7 =H or C 1 -C 4 -alkyl,

the process comprising carbodiimidizing isocyanate-containing compounds of formula (II)
O═C═N—R 2 —R 1   (II),

optionally in the presence of isocyanate-containing compounds of formula (III)
O═C═N—R 2   (III),

wherein R 1 and R 2 are as defined above,

in the presence of at least one basic cesium salt, and at a temperature of 120° C. to 220° C.

2. The process as claimed in claim 1 , wherein the basic cesium salt is cesium carbonate and/or cesium alkoxide.

3. The process as claimed in claim 1 , wherein the isocyanate-containing compounds of formula (II) comprise:
any of (IIa), (IIb), (IIc) or (IId) alone, or (IIa) and (IIb) together, wherein these compounds correspond to the following formulae

4. The process according to claim 1 , wherein the basic cesium salt is employed in a concentration of 0.1 to 20 wt %, based on the overall mixture.

5. The process according to claim 1 , further comprising, following the carbodiimidization, filtering off and/or removing the basic cesium salts by extraction using a solvent.

6. The process as claimed in claim 1 , further comprising conducting the carbodiimidization in the presence of a solvent.

7. The process according to claim 6 , wherein the solvent comprises at least one C 7 -C 22 -alkylbenzene.

8. A Stabilizer comprising at least 90% of the polymeric carbodiimides according to claim 1 and less than 1 ppm of organic phosphorus compounds.

9. A process for producing polyurethanes, the process comprising one of:
reacting polyester polyols with isocyanates in the presence of the polymeric carbodiimides produced according to claim 1 , or
reacting polyester polyols with isocyanates, and following the reaction, adding the polymeric carbodiimides produced according to claim 1 .

10. The process according to claim 9 , wherein the polymeric carbodiimide is employed in an amount of 0.1 to 2 wt %.

11. The process according to claim 9 , wherein the polymeric carbodiimide is employed in an amount of 1.0 to 1.5 wt %, based on the overall mixture.

12. The process as claimed in claim 1 , wherein:
m represents an integer from 3 to 20;
R 2 =C 7 -C 18 alkylarylene and/or C 7 -C 18 -aralkylene; and
the temperature is 160° C. to 200° C.

13. The process as claimed in claim 12 , wherein:
m represents an integer from 4 to 10;
the isocyanate-containing compounds of formula (II) comprise:
any of (IIa), (IIb), (IIc) or (IId) alone, or (IIa) and (IIb) together, wherein these compounds correspond to the following formulae

and
the basic cesium salt is employed in a concentration of 0.1 to 20 wt %, based on the overall mixture.

14. The process as claimed in claim 1 , wherein:
the basic cesium salt is cesium methoxide, and the basic cesium salt is employed in a concentration of 2 to 4 wt %, based on the overall mixture; and
the isocyanate-containing compounds of formula (II) are converted in the presence of the isocyanate-containing compounds of formula (III) at a temperature of 180° C. to 200° C.

Assignees

• Lanxess Deutschland Gmbh

Inventors

• Laufer Wilhelm
• Herd Oliver
• Sperber Rolf

Classifications

• C08G18/797

  containing carbodiimide and/or uretone-imine groups · CPC title

• C08G18/7671

  containing only one alkylene bisphenyl group · CPC title

• C08G18/025 Primary

  the polymeric products containing carbodiimide groups · CPC title

• C07C267/00 Primary

  Carbodiimides · CPC title

• C09J175/06

  from polyesters · CPC title