IP Library Granted Patent US 11,319,402
Granted Patent B2
US 11,319,402 · App. 17/053,822 · Granted May 3, 2022

Method for producing a polyisocyanate polymer and a polyisocyanurate plastic

Inventors: Heiko Hocke (Leverkusen, DE); Mathias Matner (Neuss, DE); Dirk Achten (Leverkusen, DE); Hans-Josef Laas (Odenthal, DE); Dieter Mager (Leverkusen, DE)
Assignee: COVESTRO INTELLECTUAL PROPERTY GMBH & CO. KG
C08G18/755C08G18/092C08G18/097C08G18/161C08G18/168C08G18/1808C08G18/225C08G18/722C08G18/73C08G18/792C08J5/043C09D179/04C08G2115/02C08J2379/04
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Quick Facts
Patent No.
US 11,319,402
App. No.
17/053,822
Granted
May 3, 2022
Kind
B2
Abstract

The invention relates to a method for producing a polyisocyanate polymer and to the polyisocyanate polymer obtainable from the method and to the use thereof as part of a two-stage method for producing a polyisocyanurate plastic, in particular for producing coatings, films, semi-finished products or molded parts containing such a polyisocyanurate plastic.

Claims (39)

1. A process for producing a semifinished product, comprising

a) providing a reaction mixture comprising a component having isocyanate-reactive groups, wherein a molar ratio of isocyanate groups to isocyanate-reactive groups is at least 3:1, the reaction mixture comprising

(i) a polyisocyanate composition A,

(ii) a catalyst B1 that catalyzes the reaction of isocyanate groups to give uretdione groups, and

(iii) a catalyst B2 that catalyzes the reaction of isocyanate and uretdione groups to give isocyanurate groups, wherein catalyst B1 is different than catalyst B2;

b) wetting a fiber, a woven fabric, a nonwoven scrim or a knit with the reaction mixture; and

c) catalytically polymerizing the polyisocyanate composition A to give a polyisocyanate polymer C that forms a layer on the fiber, the woven fabric, the nonwoven scrim or the knit, wherein the polyisocyanate polymer C has a modulus G″ of ≥1*10 6 Pa as determined by a plate/plate rheometer at 1/s at 23° C. based on ISO 6721-10:2015-09 and comprises uretdione groups; and

wherein the catalytic polymerization is conducted at an average temperature of not more than 100° C. over a period of 30 minutes up to 14 days.

2. A process for producing a composite material having a matrix comprising a polyisocyanurate plastic, comprising

a) providing a reaction mixture comprising a component having isocyanate-reactive groups, wherein a molar ratio of isocyanate groups to isocyanate-reactive groups is at least 3:1, the reaction mixture comprising

(i) a polyisocyanate composition A,

(ii) a catalyst B1 that catalyzes the reaction of isocyanate groups to give uretdione groups, and

(iii) a catalyst B2 that catalyzes the reaction of isocyanate and uretdione groups to give isocyanurate groups, wherein catalyst B1 is different than catalyst B2;

b) wetting a fiber, a woven fabric, a nonwoven scrim or a knit with the reaction mixture; and

c) catalytically polymerizing the polyisocyanate composition A to give a polyisocyanate polymer C that forms a layer on the fiber, the woven fabric, the nonwoven scrim or the knit, wherein the polyisocyanate polymer C has a modulus G″ of ≥1*10 6 Pa as determined by a plate/plate rheometer at 1/s at 23° C. based on ISO 6721-10:2015-09 and comprises uretdione groups, and wherein the catalytic polymerization is conducted at an average temperature of not more than 100° C. over a period of 30 minutes up to 14 days; and

d) comprising catalytically trimerizing polyisocyanate polymer C to give a polyisocyanurate plastic D at a temperature of at least 100° C., wherein the temperature in process step d) is at least 20° C. higher than the temperature in process step c).

3. A process for producing a polyisocyanurate plastic D, comprising

a) providing a polyisocyanate polymer C having a modulus G″ of at least 1*10 6 Pa as determined by a plate/plate rheometer at 1/s at 23° C. based on ISO 6721-10:2015-09, comprising

(i) uretdione groups; and

(ii) a catalyst B2 that catalyzes the reaction of uretdione groups to give isocyanurate groups;

obtained by

a1) providing a reaction mixture comprising a component having isocyanate-reactive groups, wherein a molar ratio of isocyanate groups to isocyanate-reactive groups is at least 3:1, the reaction mixture comprising

(i) a polyisocyanate composition A,

(ii) a catalyst B1 that catalyzes the reaction of isocyanate groups to give uretdione groups, and

(iii) a catalyst B2 that catalyzes the reaction of isocyanate and uretdione groups to give isocyanurate groups, wherein catalyst B1 is different than catalyst B2; and

a2) catalytically polymerizing the polyisocyanate composition A to give the polyisocyanate polymer C;

wherein the polymerization to give the polyisocyanate polymer C is conducted at an average temperature of not more than 100° C. over a period of 30 minutes up to 14 days, and

b) catalytically trimerizing polyisocyanate polymer C to give a polyisocyanurate plastic D at a temperature between 100° C. and 400° C., wherein the temperature in catalytically trimerizing polyisocyanate polymer C to give polyisocyanate plastic D is at least 20° C. higher than the temperature in catalytically polymerizing the polyisocyanate composition A to prepare the polyisocyanate polymer C.

4. The process as claimed in claim 3 , wherein the polyisocyanate polymer C is provided in process step a) at a site at least 10 m removed from a site at which the catalytic trimerization in process step b) is performed.

5. The process as claimed in claim 3 , wherein the polyisocyanate polymer C provided in process step a) is reshaped prior to performing the catalytic trimerization in process step b).

6. The process as claimed in claim 1 , wherein a proportion of aliphatically and cycloaliphatically bonded isocyanate groups in the polyisocyanate composition A is at least 80 mol % based on a total amount of all isocyanate groups present therein.

7. The process as claimed in claim 1 , wherein the catalyst B2, at temperatures of not more than 60° C., by comparison with catalyst B1, has a reaction rate coefficient for the conversion of isocyanate groups k(T) ISOB2 that is at least a factor of 2 less than the reaction rate coefficient k(T) ISOB1 .

8. The process as claimed in claim 1 , wherein the polyisocyanate polymer C has a glass transition temperature of not more than 60° C.

9. An isocyanurate plastic obtained by the process as claimed in claim 3 .

10. A semifinished product obtained by the process as claimed in claim 1 .

11. A coating, film, semifinished product or molding comprising the polyisocyanurate plastic D prepared by the process as claimed in claim 3 .

12. The process as claimed in claim 1 , wherein the component comprising isocyanate-reactive groups comprises the polyisocyanate composition A, the catalyst B1, the catalyst B2, or a combination thereof.

13. The process as claimed in claim 2 , wherein the component comprising isocyanate-reactive groups comprises the polyisocyanate composition A, the catalyst B1, the catalyst B2, or a combination thereof.

14. The process as claimed in claim 3 , wherein the component comprising isocyanate-reactive groups comprises the polyisocyanate composition A, the catalyst B1, the catalyst B2, or a combination thereof.

Assignments (3)
MERGER Recorded Oct 29, 2024
From: COVESTRO INTELLECTUAL PROPERTY GMBH & CO. KG
To: COVESTRO DEUTSCHLAND AG
Reel/Frame 069272/0414 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 9, 2020
From: HOCKE, HEIKO; MATNER, MATHIAS; ACHTEN, DIRK; LAAS, HANS-JOSEF; MAGER, DIETER
To: COVESTRO DEUTSCHLAND AG
Reel/Frame 054309/0179 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 9, 2020
From: COVESTRO DEUTSCHLAND AG
To: COVESTRO INTELLECTUAL PROPERTY GMBH & CO. KG
Reel/Frame 054309/0196 →
Priority Claims (1)
EP 18172967 · May 17, 2018 · regional
Continuity (1)
Related Publication 20210246255A1 · Aug 12, 2021
Cited By (1)
US 12,492,281