THREE-COMPONENT POLYURETHANE ADHESIVE COMPOSITIONS

• US 20200131414A1
• Filed: 06/13/2018
• Published: 04/30/2020
• Est. Priority Date: 07/11/2017
• Status: Abandoned Application

• Current Assignee: Ddp Specialty Electronic Materials US, LLC (DuPont de Nemours, Inc.)
• Original Assignee: Ddp Specialty Electronic Materials Us, Inc. (DuPont de Nemours, Inc.)
• Inventors: Grunder, Sergio, Schmatloch, Stefan, Kunz, Joel
• Application Number:
  US16/618,834
• Publication Number:
  US 20200131414A1
• Time in Patent Office: Days
• CPC Class Codes: C08G 18/12 using two or more compounds having active hydrogen in the first polymerisation step
• CPC Class Codes: C08G 18/165 covered by C08G18/18 and C08G18/24
• CPC Class Codes: C08G 18/2063 having two nitrogen atoms in the condensed ring system
• CPC Class Codes: C08G 18/242 organometallic compounds containing tin-carbon bonds
• CPC Class Codes: C08G 18/283 Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
• CPC Class Codes: C08G 18/3206 aliphatic
• CPC Class Codes: C08G 18/4063 Mixtures of compounds of group C08G18/62 with other macromolecular compounds
• CPC Class Codes: C08G 18/4825 Polyethers containing two hydroxy groups C08G18/4833 - C08G18/5096 take precedence
• CPC Class Codes: C08G 18/4833 Polyethers containing oxyethylene units
• CPC Class Codes: C08G 18/4841 containing oxyethylene end groups
• CPC Class Codes: C08G 18/6204 Polymers of olefins unsaturated polymers of conjugated dienes C08G18/69
• CPC Class Codes: C08G 18/6674 with compounds of group C08G18/3203
• CPC Class Codes: C08G 18/6677 having at least three hydroxy groups
• CPC Class Codes: C08G 18/73 acyclic
• CPC Class Codes: C08G 18/7671 containing only one alkylene bisphenyl group
• CPC Class Codes: C08G 18/797 containing carbodiimide and/or uretone-imine groups
• CPC Class Codes: C08G 18/798 containing urethdione groups
• CPC Class Codes: C08K 2003/2227 of aluminium
• CPC Class Codes: C08K 2201/005 Additives being defined by their particle size in general
• CPC Class Codes: C08K 2201/006 Additives being defined by their surface area
• CPC Class Codes: C08K 3/04 : Carbon
• CPC Class Codes: C08K 3/346 : Clay
• CPC Class Codes: C08K 3/36 : Silica
• CPC Class Codes: C08K 9/06 : with silicon-containing compounds
• CPC Class Codes: C09J 175/08 : from polyethers

Abstract

Disclosed are latent three-component polyurethane adhesive compositions which includes; (a) a first polyol component comprising (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; (iii) from 0.01 to 1 weight percent, based on the total weight of the first polyol component, of one or more latent room temperature organometallic catalysts; and (iv) from 0.01 to 1 weight percent, based on the total weight of the first polyol component, of one or more one or more blocked cyclic amidine compound catalysts or one or more phenol-blocked cyclic amidine compounds catalysts; (b) a second polyol component comprising (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; (iii) from 0.01 to 1 weight percent, based on the total weight of the second polyol component, of one or more latent room temperature organometallic catalysts; and (iv) from 0.01 to 1 weight percent, based on the total weight of the second polyol component, of one or more blocked cyclic amidine compound catalysts or one or more phenol-blocked cyclic amidine compounds catalysts; and (c) an isocyanate component comprising (i) one or more isocyanate compounds; wherein the isocyanate component and the first and second polyol components are contacted at an isocyanate index of 0.5 to 2.

Claims

1. A three-component polyurethane adhesive composition comprising:

(a) a first polyol component comprising (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;

(iii) from 0.01 to 1 weight percent, based on the total weight of the first polyol component, of one or more latent room temperature organometallic catalysts; and

(iv) from 0.01 to 1 weight percent, based on the total weight of the first polyol component, of one or more one or more blocked cyclic amidine compound catalysts or one or more phenol-blocked cyclic amidine compounds catalysts;

(b) a second polyol component comprising (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;

(iii) from 0.01 to 1 weight percent, based on the total weight of the second polyol component, of one or more latent room temperature organometallic catalysts; and

(iv) from 0.01 to 1 weight percent, based on the total weight of the second polyol component, of one or more blocked cyclic amidine compound catalysts or one or more phenol-blocked cyclic amidine compounds catalysts; and

(c) an isocyanate component comprising (i) one or more isocyanate compounds;

wherein the isocyanate component and the first and second polyol components are contacted at an isocyanate index of 0.5 to 2.

2. The three-component polyurethane adhesive composition of claim 1, wherein the one or more polyols having a hydroxyl equivalent weight of 400 to 2000 and a nominal hydroxyl functionality of 2 to 4 of the first polyol component and the second polyol component are the same or different and are one or more polyether polyols.

3. The three-component polyurethane adhesive composition of claim 1, wherein the one or more aliphatic diol chain extenders of the first polyol component and the second polyol component are the same or different and each have a hydroxyl equivalent weight of 200 or less and two aliphatic hydroxyl groups per molecule.

4. The three-component polyurethane adhesive composition of claim 1, wherein the isocyanate component includes both aliphatic and aromatic isocyanates.

5. The three-component polyurethane adhesive composition of claim 1, wherein the one or more latent room temperature organometallic catalysts of the first polyol component and the second polyol component are the same or different and contain tin, zinc or bismuth.

6. The three-component polyurethane adhesive composition of claim 5, wherein the one or more latent room temperature organometallic catalysts of the first polyol component and the second polyol component are the same or different and are zinc alkanoates, bismuth alkanoates, dialkyltin alkanoates, dialkyl tin mercaptides, dialkyl tin bis(alkylmercaptoacetates), dialkyltin thioglycolates or mixtures thereof.

7. The three-component polyurethane adhesive composition of claim 1, wherein the one or more blocked cyclic amidine compound catalysts or the one or more phenol-blocked cyclic amidine compounds catalysts comprise 1,8-Diazabicyclo[5.4.0]undec-7-ene) or 1,5-Diazabicyclo[4.3.0]non-5-ene.

8. The three-component polyurethane adhesive composition of claim 1, wherein:

the first polyol component (a) comprises 0.02 to 0.3 weight percent, based on the total weight of the first polyol component, of the one or more latent room temperature organometallic catalysts (iii); and

0.03 to 0.5 weight percent, based on the total weight of the first polyol component, of the one or more blocked cyclic amidine compound catalysts or the one or more phenol-blocked cyclic amidine compounds catalysts (iv); and

the second polyol component (b) comprises 0.02 to 0.3 weight percent, based on the total weight of the second polyol component, of the one or more latent room temperature organometallic catalysts (iii); and

0.03 to 0.5 weight percent, based on the total weight of the second polyol component, of the one or more blocked cyclic amidine compound catalysts or the one or more phenol-blocked cyclic amidine compounds catalysts (iv).

9. The three-component polyurethane adhesive composition of claim 1, comprising a volume ratio of the first polyol component to the second polyol component to the isocyanate component of 0.1:

49.9;

50 to 49.9;

0.1;

50.

10. The three-component polyurethane adhesive composition of claim 1, having an open time of 3 minutes or greater after contacting the first polyol component, the second polyol component and the isocyanate component.

11. The three-component polyurethane adhesive composition of claim 10, having an open time of 6 minutes or greater after contacting the first polyol component, the second polyol component and the isocyanate component.

12. The three-component polyurethane adhesive composition of claim 1, wherein at least one of the first polyol component, the second polyol component and the isocyanate component further comprises one or more particulate fillers.

18. The process according to claim 1, wherein at least one of the first polyol component, the second polyol component and the isocyanate component of the three-component polyurethane adhesive composition further comprises one or more particulate fillers.

13. A process for preparing a three-component polyurethane adhesive composition comprising:

(a) metering a first stream comprising a first polyol component into an in-line mixing unit, wherein the first polyol component comprises (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;

(iii) from 0.01 to 1 weight percent, based on the total weight of the first polyol component, of one or more latent room temperature organometallic catalysts; and

(iv) from 0.01 to 1 weight percent, based on the total weight of the first polyol component, of one or more blocked cyclic amidine compound catalysts or one or more phenol-blocked cyclic amidine compounds catalysts;

(b) metering a second stream comprising a second polyol component into the in-line mixing unit, wherein the second polyol component comprises (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;

(iii) from 0.01 to 1 weight percent, based on the total weight of the second polyol component, of one or more latent room temperature organometallic catalysts; and

(iv) from 0.01 to 1 weight percent, based on the total weight of the second polyol component, of one or more blocked cyclic amidine compound catalysts or one or more phenol-blocked cyclic amidine compounds catalysts;

(c) metering a third stream comprising an isocyanate component into the in-line mixing unit, wherein the isocyanate component comprises (i) one or more isocyanate compounds;

wherein the isocyanate component and the first and second polyol components are contacted at an isocyanate index of 0.5 to 2;

wherein the first polyol component, second polyol component and isocyanate component are contacted in the in-line mixing unit to form the three-component polyurethane adhesive composition; and

(d) dispensing the three-component polyurethane adhesive composition.

14. The process according to claim 13, wherein the first polyol component, the second polyol component and the isocyanate component are contacted in the in-line mixing unit for a time of from 0.1 to 60 seconds to form the three-component polyurethane adhesive composition.

15. The process according to claim 13, wherein the one or more latent room temperature organometallic catalysts of the first polyol component and the second polyol component are the same or different and are zinc alkanoates, bismuth alkanoates, dialkyltin alkanoates, dialkyl tin mercaptides, dialkyl tin bis(alkylmercaptoacetates), dialkyltin thioglycolates or mixtures thereof, and the one or more blocked cyclic amidine compound catalysts or the one or more phenol-blocked cyclic amidine compounds catalysts of the first polyol component and the second polyol component are the same or different and are 1,8-Diazabicyclo[5.4.0]undec-7-ene) or 1,5-Diazabicyclo[4.3.0]non-5-ene.

16. The process according to claim 13, wherein the three-component polyurethane adhesive composition comprises a volume ratio of the first polyol component to the second polyol component to the isocyanate component of 0.1:

49.9;

50 to 49.9;

0.1;

50.

17. The process according to claim 13, wherein the three-component polyurethane adhesive composition comprises a volume ratio of the first polyol component to the second polyol component to the isocyanate component of 0.1:

49.9;

50 to 49.9;

0.1;

50, and further wherein the three-component polyurethane adhesive composition has an open time of 3 minutes or greater after contacting the first polyol component, the second polyol component and the isocyanate component.

19. The process according to claim 13, wherein the in-line mixing unit is one of a static mixing unit or a dynamic mixing unit.

20. The process according to claim 13, further comprising:

(e) applying the three-component polyurethane adhesive composition to at least a portion of a first substrate; and

(f) contacting a second substrate with the first substrate with the three-component polyurethane adhesive composition being disposed between the first and second substrate.