Isocyanate-terminated prepolymers based on polyoxymethylene-polyoxyalkylene block copolymers, process for the preparation and use thereof

Patent metadata

Field	Value
Publication number	US-2023235110-A1
Application number	US-202118042800-A
Country	US
Kind code	A1
Filing date	Aug 30, 2021
Priority date	Sep 1, 2020
Publication date	Jul 27, 2023
Grant date	—

Abstract

The present invention relates to isocyanate-terminated prepolymers based on polyoxymethylene-polyoxyalkylene block copolymers, to a process for their preparation, and to the use of these isocyanate-terminated prepolymers as isocyanate components in 1- and 2-component systems for coatings, adhesives and sealants.

First claim

1 . A process for preparing an isocyanate-terminated prepolymer comprising reacting
A. at least one aliphatic, cycloaliphatic, araliphatic and/or aromatic polyisocyanate, wherein component A has an NCO content according to DIN EN ISO 11909:2007-05 of 15% to 60% by weight, B. at least one polyoxymethylene-polyoxyalkylene block copolymer having a hydroxyl number according to DIN 53240-2:2007-11 of 15 mg KOH/g to 200 mg KOH/g, C. i) at least one amino-containing polyether based on propylene oxide having a hydroxyl number according to DIN 53240-2:2007-11 of 40 to 80 mg KOH/g, an OH functionality of 4.0 and an amine content according to DIN EN 9702:1998 in the range from 0.5% to 1.0% by weight,
ii) optionally at least one amino-containing polyether based on based on ethylene oxide, propylene oxide or a mixture of ethylene oxide and propylene oxide having an NH 2 -functionality of 2 or 3, with the exception of amino-containing polyethers of component Ci, and
D. optionally auxiliaries containing protic acids (D2) and/or auxiliaries which are not protic acids of D2 (D1).

2 . The process as claimed in claim 1 , characterized in that component B consists of a polyoxymethylene-polypropylene oxide block copolymer or a polyoxymethylene-polyoxyalkylene carbonate block copolymer.

3 . The process as claimed in claim 1 , wherein at least component B has been prepared in the presence of a double metal cyanide catalyst, and component B contains at least some of the double metal cyanide catalyst, wherein the content of double metal cyanide catalyst based on the total amount of components B and C is 10 to 5000 ppm determined using the amount of metal content from the double metal cyanide catalyst determined according to DIN ISO 17025 (August 2005).

4 . The process as claimed in claim 1 , wherein the at least one polyoxymethylene-polyoxyalkylene block copolymer of component B has a hydroxyl number according to DIN 53240-2:2007-11 of 15 mg KOH/g to 150 mg KOH/g.

5 . The process as claimed in claim 1 , wherein the at least one amino-containing polyether of component Ci has a hydroxyl number according to DIN 53240-2:2007-11 of 45 to 75 mg KOH/g.

6 . The process as claimed in claim 1 , wherein the at least one amino-containing polyether of component Ci has an amine content according to DIN EN 9702:1998 of 0.56% to 0.94% by weight.

7 . The process as claimed in claim 1 , wherein component A comprises at least one aromatic polyisocyanate.

8 . The process as claimed in claim 1 , wherein the isocyanate-terminated prepolymer is a reaction product of a composition comprising:
50% to 70% by weight of component A, 15% to 30% by weight of component B, 10% to 30% by weight of component Ci, 0% to 15% by weight of component Cii, 0.10% to 0.20% by weight of component D1, and 0% to 0.50% by weight of component D2,
wherein the % by weight values are based on the sum of all components of the composition.

9 . An isocyanate-terminated prepolymer obtained by the process as claimed in claim 1 .

10 . (canceled)

11 . A paint, adhesive or sealant system containing at least one isocyanate-terminated prepolymer as claimed in claim 17 .

12 . The paint, adhesive or sealant system as claimed in claim 11 , wherein the system is a 1-component moisture-curable system which comprises no isocyanate-reactive components in addition to the at least one isocyanate-terminated prepolymer.

13 . The paint, adhesive or sealant system as claimed in claim 11 , wherein the system is a 2-component moisture-curable system which comprises at least one isocyanate-reactive component in addition to the at least one isocyanate-terminated prepolymer.

14 . A substrate coated or bonded with paint, adhesive or sealant systems as claimed in claim 11 .

15 . The process as claimed in claim 2 , wherein the block copolymer comprises two terminal polyoxyalkylene blocks.

16 . The process as claimed in claim 7 wherein the at least one aromatic polyisocyanate comprises 1,5-naphthalene diisocyanate, diisocyanatodiphenylmethane, poly(methylene phenyl isocyanate), diisocyanatomethylbenzene, or a mixture thereof.

17 . An isocyanate-terminated prepolymer comprising a reaction product of a composition comprising:
A. at least one aliphatic, cycloaliphatic, araliphatic and/or aromatic polyisocyanate, wherein component A has an NCO content according to DIN EN ISO 11909:2007-05 of 15% to 60% by weight, B. at least one polyoxymethylene-polyoxyalkylene block copolymer having a hydroxyl number according to DIN 53240-2:2007-11 of 15 mg KOH/g to 200 mg KOH/g, C. i) at least one amino-containing polyether based on propylene oxide having a hydroxyl number according to DIN 53240-2:2007-11 of 40 to 80 mg KOH/g, an OH functionality of 4.0 and an amine content according to DIN EN 9702:1998 in the range from 0.5% to 1.0% by weight,
ii) optionally at least one amino-containing polyether based on based on ethylene oxide, propylene oxide or a mixture of ethylene oxide and propylene oxide having an NH 2 -functionality of 2 or 3, with the exception of amino-containing polyethers of component Ci, and
D. optionally auxiliaries containing protic acids (D2) and/or auxiliaries which are not protic acids of D2 (D1).

18 . The isocyanate-terminated prepolymer of claim 17 , wherein the isocyanate-terminated prepolymer is a reaction product of a composition comprising:
50% to 70% by weight of component A, 15% to 30% by weight of component B, 10% to 30% by weight of component Ci, 0% to 15% by weight of component Cii, 0.10% to 0.20% by weight of component D1, and 0% to 0.50% by weight of component D2,
wherein the % by weight values are based on the sum of all components of the composition.

Assignees

• Covestro Deutschland Ag

Inventors

• Zorn Anna-Marie
• Thiebes Christoph
• Baumbach Beate
• Hill Annika
• Weinkraut Michael
• Schuetze Mike

Classifications

• C08G18/10 Primary

  Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step · CPC title

• C08G18/5021

  having nitrogen · CPC title

• C08G18/307

  Atmospheric humidity · CPC title

• C09J175/08

  from polyethers · CPC title

• C08G2170/00

  Compositions for adhesives · CPC title