IP Library Granted Patent US 10,400,145
Granted Patent B2
US 10,400,145 · App. 15/579,745 · Granted Sep 3, 2019

Latent two-part polyurethane adhesives cured with infrared radiation

Inventors: Stefan Schmatloch (Horgen, CH); Joel Kunz (Horgen, CH)
Assignee: DOW GLOBAL TECHNOLOGIES LLC
C09J175/08B32B37/12C08G18/165C08G18/2063C08G18/242C08G18/244C08G18/482C08G18/4812C08G18/4837C08G18/5024C08G18/6674C08G18/798C08J3/24C08J3/244C08J3/28C09J5/06C09J11/04C09J175/04B32B7/12B32B2037/1253C08J2375/04C08K3/04C08K3/346C08K3/36C08K9/00C09J2205/31C09J2400/226C09J2475/00
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Quick Facts
Patent No.
US 10,400,145
App. No.
15/579,745
Granted
Sep 3, 2019
Kind
B2
Abstract

Two-component polyurethane adhesives include a polyol component and a polyisocyanate component. The polyol component includes a polyether polyol and an aliphatic diol chain extender, but is devoid of primary and second amine compounds. The polyisocyanate component includes one or more polyisocyanate compounds. The adhesive contains a mixture of a dialkyltinthioglycolate catalyst and an acid-blocked cyclic amidine catalyst. The tin catalyst is formulated into the polyol component, whereas the cyclic amidine catalyst can be formulated into either the polyol or the polyisocyanate components.

Claims (29)

1. A two-component polyurethane adhesive composition having a polyol component and an isocyanate component, wherein:

the polyol component includes:

a) at least 35 weight percent, based on the weight of the polyol component, of one or more polyols having a hydroxyl equivalent weight of 400 to 2000 and a nominal hydroxyl functionality of 2 to 4;

b) 2.5 to 6 equivalents, per equivalent of a), of one or more aliphatic diol chain extenders;

c) from 0.05 to 0.15 part by weight, per 100 parts by weight of component a), of one or more one or more latent room temperature organometallic catalysts; and

d) 0 to 60 weight percent, based on the weight of the polyol component, of at least one particulate filler, the polyol component being devoid of compounds having primary and/or secondary amino groups;

the polyisocyanate component includes:

at least 50% by weight of one or more organic polyisocyanate compounds; and

0 to 50% by weight of at least one particulate filler;

wherein the isocyanate equivalent weight of the polyisocyanate component and the hydroxyl equivalent weight of the polyol component are such that when the polyisocyanate component and the polyol component are mixed at a 1:1 ratio by volume the isocyanate index is 1.1 to 1.8, and further wherein the polyol component or the polyisocyanate component includes an acid-blocked cyclic amidine catalyst, wherein when the acid-blocked amidine catalyst is present in the polyol component, it is present in an amount of 0.10 to 0.25 parts by weight per 100 parts by weight component a) and the combined weight of the acid-blocked amidine catalyst and the one or more latent room temperature organometallic catalysts is up to 0.31 parts by weight per 100 parts by weight of component a), and the acid-blocked amidine catalyst is present in an amount of 0.10 to 0.35 parts by weight per 100 parts by weight of the polyisocyanate component when present in the polyisocyanate component.

2. The two-component polyurethane adhesive composition of claim 1 , wherein the polyol component contains 0.06 to 0.12 part by weight of the one or more latent room temperature organometallic catalysts per 100 parts by weight of component a).

3. The two-component polyurethane adhesive composition of claim 1 , wherein the acid-blocked amidine catalyst is in the polyol component, and is present in an amount of 0.10 to 0.22 part by weight per 100 parts by weight of component a).

4. The two-component polyurethane adhesive composition of claim 1 , wherein the acid-blocked amidine catalyst is in the polyisocyanate component, and is present in an amount of 0.10 to 0.25 part by weight per 100 parts by weight of component a).

5. The two-component polyurethane adhesive composition of claim 1 , wherein the acid-blocked amidine catalyst is an acid-blocked 1,8-diazabicycloundec-7-ene or 1,5-Diazabicyclo[4.3.0]non-5-ene.

6. The two-component polyurethane adhesive composition of claim 5 wherein the acid-blocked amidine catalyst is blocked with phenol, a substituted phenol, an aliphatic carboxylic acid having 1 to 24 carbon atoms or a mixture of two or more thereof.

7. The two-component polyurethane adhesive composition of claim 1 wherein the particulate filler constitutes 25 to 60% of the weight of the polyol component.

8. The two-component polyurethane adhesive composition of claim 1 wherein the particulate filler constitutes 20 to 50% of the weight of the polyisocyanate component.

9. The two-component polyurethane adhesive composition of claim 1 wherein the polyisocyanate component includes both aliphatic and aromatic isocyanates.

10. The composition according to claim 1 wherein the one or more latent room temperature organometallic catalysts contain tin, zinc or bismuth.

11. The composition according to claim 1 wherein the one or more latent room temperature organometallic catalysts are zinc alkanoates, bismuth alkanoates, dialkyltin alkanoates, dialkyl tin mercaptides, dialkyl tin bis(alkylmercaptoacetates), dialkyltin thioglycolates or mixtures thereof.

12. A composition according to claim 1 wherein the one or more latent room temperature organometallic catalysts are dialkyl tin mercaptides, dialkyl tin bis(alkylmercaptoacetates), dialkyltin thioglycolates or mixtures thereof.

13. A composition according to claim 1 wherein the one or more latent room temperature organometallic catalysts are dialkyltin thioglycolates.

14. A cured adhesive formed by mixing the components of the two-component polyurethane adhesive composition of claim 1 to form an adhesive mixture, and curing the mixed adhesive.

15. A method of bonding two substrates, comprising combining the components of the two-component polyurethane adhesive of claim 1 to form an adhesive mixture, forming a layer of the adhesive mixture at a bondline between two substrates to form an assembly, and curing the layer at the bondline to form a cured adhesive bonded to each of the substrates.

16. The method of claim 15 wherein the curing step is at least partially performed by applying infrared radiation to the assembly.

17. The method of claim 16 , wherein the curing is performed by partially curing the adhesive layer at the bondline by applying infrared radiation to the assembly and, in a subsequent and separate curing step, completing the cure of the adhesive layer.

18. The method of claim 15 wherein the acid-blocked amidine catalyst is in the polyisocyanate component, and is present in an amount of 0.10 to 0.25 part by weight per 100 parts by weight of component a).

19. A composition according to claim 1 wherein the aliphatic diol chain extender(s) each have a hydroxyl equivalent weight of up to 100.

20. A composition according to claim 1 wherein the aliphatic diol chain extender(s) includes monoethylene glycol, 1,4-butanediol or a mixture thereof.

Assignments (5)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 10, 2024
From: DOW GLOBAL TECHNOLOGIES LLC
To: THE DOW CHEMICAL COMPANY
Reel/Frame 069923/0030 →
CHANGE OF LEGAL ENTITY Recorded Sep 10, 2024
From: DDP SPECIALTY ELECTRONIC MATERIALS US, INC
To: DDP SPECIALTY ELECTRONIC MATERIALS US, LLC
Reel/Frame 068907/0881 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 10, 2024
From: THE DOW CHEMICAL COMPANY
To: DDP SPECIALTY ELECTRONIC MATERIALS US, INC
Reel/Frame 068922/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 29, 2018
From: SCHMATLOCH, STEFAN; KUNZ, JOEL
To: DOW EUROPE GMBH
Reel/Frame 044754/0423 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 29, 2018
From: DOW EUROPE GMBH
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 044754/0585 →
Continuity (5)
Provisional Application 62316677 · Apr 1, 2016
Provisional Application 62316680 · Apr 1, 2016
Provisional Application 62213650 · Sep 3, 2015
Provisional Application 62181359 · Jun 18, 2015
Related Publication 20180179320A1 · Jun 28, 2018