High molecular weight ortho cresol-novolak resins and process for the preparation thereof using alcoholic or acidic organic solvents

• US 4,876,324 A
• Filed: 05/13/1987
• Issued: 10/24/1989
• Est. Priority Date: 06/08/1984
• Status: Expired due to Fees

• Current Assignee: Mitsubishi Petrochemical Co., Ltd. (Mitsubishi Chemical Group Corp.)
• Original Assignee: Mitsubishi Petrochemical Co., Ltd. (Mitsubishi Chemical Group Corp.)
• Inventors: Nakano, Yoshitomo, Kada, Masumi
• Primary Examiner(s): Kight, John
• Assistant Examiner(s): KRASS, FREDERICK F
• Application Number:
  US07/049,335
• Time in Patent Office: 895 Days
• Field of Search: 528/142, 528/144
• US Class Current: 528/142
• CPC Class Codes: C08G 8/10 with phenol
• CPC Class Codes: C08L 2666/22 Macromolecular compounds not provided for in C08L2666/16 - C08L2666/20
• CPC Class Codes: C08L 61/04 Condensation polymers of aldehydes or ketones with phenols only
• CPC Class Codes: C08L 61/06 of aldehydes with phenols
• CPC Class Codes: C08L 63/00 Compositions of epoxy resins; Compositions of derivatives of epoxy resins

Abstract

Orthocresol or a mixture of orthocresol and paracresol and an aldehyde compound or a derivative thereof are subjected to polycondensation in a solvent selected from an aliphatic alcohol having 3 to 12 carbon atoms, a glycol ether having 3 to 6 carbon atoms, benzyl alcohol and an aliphatic carboxylic acid having 2 to 6 carbon atoms, in the presence of an acid catalyst, to obtain linear and high molecular weight orthocresol-novolak resins or orthocresol/paracresol random copolymerized novolak resins which have a high softening point of 145° C. or higher and a high number average molecular weight of 1500 or more and which are highly soluble in alcohols and ketones and are highly compatible with resins.

Claims

1. A process for preparing a high molecular weight cresol-novolak resin having a softening point of 30°

C. or higher, consisting essentially of polycondensing orthocresol or a mixture of orthocresol and paracresol with an aldehyde compound or a derivative thereof in a solvent selected from the group consisting of C_3-12 aliphatic monoalcohols, C_3-6 monohydric glycol ethers and benzyl alcohol, in the presence of a protonic acid catalyst.

2. The process as claimed in claim 1, wherein said aldehyde is paraformaldehyde.

3. The process as claimed in claim 1, wherein said solvent is selected from the group consisting of methyl cellosolve, ethyl cellosolve, butyl cellosolve, and n-butanol.

4. The process as claimed in claim 1, wherein the amount of said solvent to be used is 150 to 300 parts by weight per 100 parts by weight of orthocresol.

5. The process of claim 1, wherein said polycondensing step consisting essentially of:

mixing said orthocresol or said mixture of orthocresol and paracresol, said aldehyde compound, said solvent and said catalyst to form a reaction mixture; and

heating said reaction mixture.

6. The process of claim 1, wherein said polycondensing step consisting essentially of:

mixing one of (a) said orthocresol or a mixture of orthocresol and paracresol, or (b) said aldehyde compound, said solvent, and said catalyst to form a reaction mixture;

heating said reaction mixture; and

adding said catalyst and one of (a) or (b) which was not used in said mixing step.

7. The method of claim 1, wherein said polycondensing step consisting essentially of the steps of:

mixing said orthocresol or said mixture of orthocresol and paracresol, said aldehyde component, and said solvent to form a reaction mixture;

heating said reaction mixture; and

adding said catalyst to said heated reaction mixture.

8. The process of claim 1, wherein said polycondensing step is conducted at a temperature of 95°

C. or higher.

9. The process of claim 8, wherein said polycondensing step is conducted at a temperature between about 105°

-150°

C.

10. The process of claim 1, wherein water is present in an amount of 15 wt. % or less during said polycondensing step.

11. The method of claim 10, wherein said water is present in an amount of 10 wt. % or less during said polycondensing step.