Manufacture of degradable polycyanurate bulk molding compositions

Patent metadata

Field	Value
Publication number	US-11767400-B2
Application number	US-202016994983-A
Country	US
Kind code	B2
Filing date	Aug 17, 2020
Priority date	Aug 17, 2020
Publication date	Sep 26, 2023
Grant date	Sep 26, 2023

Abstract

A process for the manufacture of a degradable polycyanurate bulk molding composition includes: contacting a liquid cyanate ester monomer with an additive material and a polymerization catalyst to form a reaction mixture; maintaining a temperature of the reaction mixture at about 80° C. to about 100° C. to form a polycyanurate product having a viscosity of about 120 to about 200 centipoise at 23° C.; heating a reinforcing filler at a temperature of about 50 to about 150° C. to form a pre-heated reinforcing filler; and blending the polycyanurate product with the pre-heated reinforcing filler to form the degradable polycyanurate bulk molding composition. The bulk molding composition can be used to form a degradable polycyanurate article.

First claim

What is claimed is:

1. A process for the manufacture of a degradable polycyanurate bulk molding composition, the process comprising:
contacting a liquid cyanate ester monomer with an additive material and a polymerization catalyst to form a reaction mixture;
maintaining a temperature of the reaction mixture at about 80° C. to about 100° C.;
monitoring a viscosity of the reaction mixture using an inline viscometer;
forming a polycyanurate product when the viscosity of the reaction mixture reaches about 120 to about 200 centipoise;
heating a reinforcing filler at a temperature of about 50 to about 150° C. to form a pre-heated reinforcing filler; and
blending the polycyanurate product having a temperature of 80-100° C. with the pre-heated reinforcing filler to form the degradable polycyanurate bulk molding composition.

2. The process of claim 1 , wherein
the liquid cyanate ester monomer comprises bisphenol E cyanate ester, and
the process comprises contacting bisphenol E cyanate ester and the additive material in the presence of the polymerization catalyst at a temperature of less than 40° C. for about 10 minutes to about 2 hours to form the reaction mixture.

3. The process of claim 1 , wherein
the liquid cyanate ester monomer comprises bisphenol A cyanate ester, and
the process further comprises:
melting bisphenol A cyanate ester to form the liquid cyanate ester monomer;
contacting the liquid cyanate ester monomer with the additive material in the absence of the polymerization catalyst at a temperature of about 80-100° C. for about 10 minutes to about 1 hour to form a blend; and
adding the polymerization catalyst to the blend to form the reaction mixture.

4. The process of claim 1 , comprising cooling or heating the reaction mixture to maintain the temperature of the reaction mixture at about 80° C. to about 100° C. to form the polycyanurate product.

5. The process of claim 1 , wherein the polymerization catalyst comprises a metal complex of cobalt, copper, chromium, manganese, tin, zinc, or a combination comprising at least one of the foregoing.

6. The process of claim 1 , wherein the polymerization catalyst is present in an amount of about 100 to 800 ppm based on an amount of a metal ion in the polymerization catalyst relative to an amount of the cyanate ester monomer.

7. The process of claim 1 , wherein the polymerization catalyst is added continuously.

8. The process of claim 1 , wherein the polymerization catalyst is added in single or multiple batches.

9. The process of claim 1 , wherein the reaction mixture is free of solvents.

10. The process of claim 1 , wherein the additive material comprises one or more of the following: an acid; a base; a polyol; or an epoxide.

11. The process of claim 1 , wherein the additive material is present in an amount of about 5 to about 30 wt % based on the total weight of the reaction mixture.

12. The process of claim 10 , wherein the additive material comprises the acid, which comprises one or more of the following: adipic acid; boric acid; citric acid; oxalic acid; sulfamic acid; ethylene diamine tetraacetic acid; itaconic acid; maleic acid; maleic anhydride; fumaric acid; phtalic acid; phtalic anhydride; or methyl-p-toluene sulfonate.

13. The process of claim 10 , wherein the additive material comprises the base, which comprises one or more of the following: sodium hydroxide; sodium carbonate; potassium hydroxide; potassium carbonate; lithium hydroxide; sodium silicate; sodium metasilicate pentahydrate; potassium silicate; calcium hydroxide; calcium oxide; cesium hydroxide; strontium hydroxide; rubidium hydroxide; or magnesium oxide.

14. The process of claim 1 , wherein the reinforcing filler comprises one or more of the following: carbon fibers; glass fibers; polymer fibers; or metal fibers.

15. The process of claim 1 , wherein the reinforcing filler is present in an amount of about 20 to about 60 wt. % based on the total weight of the degradable polycyanurate bulk molding composition.

16. The process of claim 1 , wherein the reinforcing filler is heated at about 110 to about 120° C. for about 3 to about 5 hours to form the pre-heated reinforcing filler.

17. The process of claim 1 , further comprising pouring the polycyanurate product into a mixer, and the pre-heated reinforcing filler is blended with the polycyanurate product in the mixer.

18. The process of claim 1 , wherein the additive material and the reinforcing filler are homogeneously dispersed in a matrix of a polycyanurate.

19. A process for the manufacture of a degradable article, the process comprising:
forming a degradable polycyanurate bulk molding composition via a process of claim 1 ; and
molding the bulk molding composition to form the degradable polycyanurate article.

Assignees

• Agrawal Devesh
• Sadana Anil
• Kovalchuk Anton
• Baker Hughes Oilfield Operations Llc

Inventors

• Agrawal Devesh
• Sadana Anil
• Kovalchuk Anton

Classifications

• C08G73/065 Primary

  Preparatory processes · CPC title

• B29C70/06

  Fibrous reinforcements only · CPC title

• C08J5/041

  with metal fibres · CPC title

• C08J5/042

  with carbon fibres · CPC title

• C08J5/043

  with glass fibres · CPC title