IP Library Granted Patent US 10,479,916
Granted Patent B2
US 10,479,916 · App. 15/579,738 · Granted Nov 19, 2019

Latent two-part polyurethane adhesives curable with infrared radiation

Inventors: Stefan Schmatloch (Horgen, CH); Joel Kunz (Horgen, CH); Sergio Grunder (Bachtobelstrasse, 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 10,479,916
App. No.
15/579,738
Granted
Nov 19, 2019
Kind
B2
Abstract

Disclosed are latent two-part polyurethane adhesives that rapidly develop adhesive strength when cured by application of infrared radiation containing a polyol component which includes; one or more polyols having a hydroxyl equivalent weight of 400 to 2000 and a nominal hydroxyl functionality of 2 to 4; one or more aliphatic diol chain extenders; and one or more latent room temperature organometallic catalysts; b) a polyisocyanate component containing one or more polyisocyanate compounds; and v) a carboxylic acid-blocked cyclic amidine compound and vi) a phenol-blocked cyclic amidine compound which each may be located in the polyol component or the isocyanate component. Further disclosed are methods of bonding structures together using the latent two-part polyurethane adhesives.

Claims (45)

1. A composition comprising a polyol component and an isocyanate component, wherein:

a) the polyol component includes;

i) one or more polyols having a hydroxyl equivalent weight of 400 to 2000 and a nominal hydroxyl functionality of 2 to 4;

ii) one or more aliphatic diol chain extenders; and

iii) one or more latent room temperature organometallic catalysts;

b) the polyisocyanate component includes:

iv) one or more polyisocyanate compounds;

wherein the polyisocyanate component includes isocyanate groups and the polyol component isocyanate-reactive groups wherein a ratio of a number of the isocyanate groups in the polyisocyanate component to a number of the isocyanate-reactive groups in the polyol component is about 1.0 to about 1.8; and v) one or more carboxylic acid-blocked cyclic amidine compounds and vi) one or more phenol-blocked cyclic amidine compounds are located in the polyol component or the isocyanate component and the composition is useful as a two-component polyurethane adhesive composition.

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

3. A 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.

4. 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.

5. A composition according to claim 1 wherein the one or more carboxylic acid-blocked cyclic amidine compounds and the one or more phenol-blocked cyclic amidine compounds comprise at least one of a carboxylic acid-blocked 1,8-Diazabicyclo[5.4.0]undec-7-ene) or 1,5-Diazabicyclo[4.3.0]non-5-ene or a phenol-blocked 1,8-Diazabicyclo[5.4.0]undec-7-ene) or 1,5-Diazabicyclo[4.3.0]non-5-ene.

6. A composition according to claim 1 wherein the one or more latent room temperature organometallic catalysts are present in an amount of about 0.005 to about 1.0 percent by weight based on the weight of the polyol component, the phenol blocked cyclic amidine compounds are present in an amount of about 0.01 to about 2.0 percent by weight based on the weight of the polyol or polyisocyanate component; and the carboxylic acid blocked cyclic amidine compounds are present in an amount of about 0.01 to about 2.0 percent by weight based on the weight of the polyol or polyisocyanate component.

7. A composition according claim 1 wherein the polyol component contains one or more particulate fillers.

8. A composition according to claim 1 wherein the polyisocyanate component contains one or more particulate fillers.

9. A composition according to claim 6 wherein:

the one or more polyols having a hydroxyl equivalent weight of 400 to 2000 and a nominal hydroxyl functionality of 2 to 4 are present in an amount of about 35 to about 80 percent by weight of the polyol component;

the one or more chain extenders are present in an amount of about 1 to about 10 percent by weight of the polyol component; and

the polyisocyanate compound is present in an amount of about 20 to about 65 percent by weight of the polyisocyanate component.

10. A composition according to claim 1 wherein the one or more latent room temperature organometallic catalysts are present in an amount of about 0.020 to about 0.050 percent by weight based on the weight of the polyol component, the phenol-blocked cyclic amidine compounds are present in an amount of about 0.01 to about 1.0 percent by weight based on the weight of the polyol or polyisocyanate component; and the carboxylic acid-blocked cyclic amidine compounds are present in an amount of about 0.01 to about 1.0 percent by weight based on the weight of the polyol or polyisocyanate component.

11. A composition according to claim 1 wherein the carboxylic acid-blocked cyclic amidine compound includes a cyclic amidine compound blocked with an aliphatic carboxylic acid having 1 to 24 carbon atoms or a mixture of two or more thereof.

12. A composition according to claim 1 wherein the phenol-blocked cyclic amidine compound includes a cyclic amidine compound blocked with a phenol, a substituted phenol, or a mixture of two or more thereof.

13. A composition according to claim 1 wherein the polyisocyanate component includes both aliphatic and aromatic isocyanates.

14. A composition according to claim 1 wherein the particulate filler constitutes about 10 to about 50 percent of the weight of the polyisocyanate component.

15. A composition according to claim 1 wherein the particulate filler constitutes about 25 to about 60 percent of the weight of the polyol component.

16. A method comprising

a) contacting the polyol component and the isocyanate component according to claim 1 and mixing to form a homogeneous mixture;

b) applying the mixture to a first substrate;

c) contacting a second substrate with the first substrate with the mixture of part a disposed between the first and second substrate; and

d) exposing a portion of the mixture to heat under conditions such that the mixture partially cures sufficiently such that the first and second substrate are bonded such that the substrates can be moved.

17. A method according to claim 16 which includes e) heating the two substrates at a temperature for a time to fully cure the mixture to bond the two substrates together.

18. A method according to claim 16 wherein the heat is applied in step d by infrared heating.

19. A method according to claim 17 wherein:

the time frame between steps d and e is about 24 hours or more; or

at least one of the substrates is a fiber reinforced plastic.

20. A composition comprising a polyol component and an isocyanate component, wherein:

a) the polyol component includes;

i) one or more polyols having a hydroxyl equivalent weight of 400 to 2000 and a nominal hydroxyl functionality of 2 to 4;

ii) one or more aliphatic diol chain extenders; and

iii) one or more latent room temperature organometallic catalysts;

b) the polyisocyanate component includes:

iv) one or more polyisocyanate compounds;

wherein

v) one or more carboxylic acid-blocked cyclic amidine compounds and

vi) one or more phenol-blocked cyclic amidine compounds are located in the polyol component or the isocyanate component and the composition is useful as a two-component polyurethane adhesive composition.

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; GRUNDER, SERGIO
To: DOW EUROPE GMBH
Reel/Frame 044755/0456 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 29, 2018
From: DOW EUROPE GMBH
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 044755/0497 →
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 20180179319A1 · Jun 28, 2018
Cited By (1)
US 1,119,918