High molecular weight, insoluble carbodiimidization catalysts

• US 4,067,820 A
• Filed: 01/30/1976
• Issued: 01/10/1978
• Est. Priority Date: 02/01/1975
• Status: Expired due to Term

• Current Assignee: Bayer AG
• Original Assignee: Bayer AG
• Inventors: Block, Hans-Dieter, Schafer, Walter, Wagner, Kuno
• Primary Examiner(s): Cockeram, H.S.
• Application Number:
  US05/653,795
• Time in Patent Office: 711 Days
• Field of Search: 260/2.5 BF, 260/551 CD, 260/77.5 AB, 260/606.5 P, 260/2 H, 252/426, 252/428, 252/430, 252/431 P
• US Class Current: 502/159
• CPC Class Codes: B01J 2231/341 1,2-additions, e.g. aldol or Knoevenagel condensations
• CPC Class Codes: B01J 31/0259 comprising phosphorous acid (-ester) groups ((RO)P(OR')2) or the isomeric phosphonic acid (-ester) groups (R(R'O)2P=O), i.e. R= C, R'= C, H
• CPC Class Codes: B01J 31/0262 comprising phosphinous acid (-ester) groups (R2P(OR')) or the isomeric phosphine oxide groups (R3P=O) , i.e. R= C, R'= C, H
• CPC Class Codes: B01J 31/08 Ion-exchange resins
• CPC Class Codes: C08G 18/797 containing carbodiimide and/or uretone-imine groups
• CPC Class Codes: Y10S 521/901 Cellular polymer containing a carbodiimide structure

Abstract

The instant invention relates to novel carbodiimidization catalysts consisting of a high molecular weight, insoluble matrix and low molecular weight carbodiimidization catalysts fixed to the matrix via ionic bonds. The novel high molecular weight catalysts are suitable for the preparation of storage stable, catalyst free, equilibrium mixtures of organic carbodiimides, uretone imines and isocyanates. Either the carbodiimide, or the uretone imine or both may contain isocyanate groups. Alternatively, mono and/or polyisocyanates free from carbodiimide and uretone imine groups may be added to the equilibrium mixture. The catalysts according to the invention are capable of bringing about selective carbodiimidization of individual isocyanates in a mixture of various isocyanates.

Claims

1. High molecular weight carbodiimidization catalysts which are insoluble in water and in polyisocyanates and which consist of a high molecular weight, insoluble, organic or inorganic matrix and low molecular weight carbodiimidization catalysts bound to this matrix via ionic bonds.

2. Carbodiimidization catalysts according to claim 1 characterized in that the high molecular weight matrix contains basic ionizable groups and the low molecular weight carbodiimidization catalyst contains acid ionizable groups.

3. Carbodiimidization catalysts according to claim 2 characterized in that the low molecular weight carbodiimidization catalyst corresponds to the following general formula:

##STR59##wherein R¹ represents an alkyl, aryl or aralkyl group having up to 14 carbon atoms which may be substituted, preferably by halogen;

R², r³ and R⁴ each represent a C₁ -C₄ alkyl group, hydrogen, chlorine or bromine;

R⁵ represents hydrogen, a C₁ -C₁₂ alkyl group and, if b = 0 a C₆ -C₁₂ aryl group;

X and Y represent oxygen or sulphur; and

a and b = 0 or 1.

4. Carbodiimidization catalysts according to claim 3 characterized in that the high molecular weight matrix is a polystyrene which has been cross-linked with from 2 to 6% by weight of divinyl benzene.

5. A process for the preparation of high molecular weight carbodiimidization catalysts comprising contacting a high molecular weight, insoluble, inorganic or organic matrix which contains ionizable groups with a solution of low molecular weight carbodiimidization catalysts which contain ionizable groups, the charge of which is opposite in sign to that of the matrix.