ACCELERATE CURE OF MOISTURE CURABLE POLYURETHANE ADHESIVE COMPOSITIONS USEFUL FOR BONDING GLASS

• US 20190309198A1
• Filed: 06/14/2019
• Published: 10/10/2019
• Est. Priority Date: 05/08/2014
• Status: Active Grant

• 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: Zhou, Lirong, Sophiea, Daniel P.
• Granted Patent: US 11,180,686 B2
• 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 18/2027 having two nitrogen atoms in the ring
• CPC Class Codes: C08G 18/2063 having two nitrogen atoms in the condensed ring system
• CPC Class Codes: C08G 18/2081 containing at least two non-condensed heterocyclic rings
• CPC Class Codes: C08G 18/244 tin salts of carboxylic acids
• CPC Class Codes: C08G 18/307 Atmospheric humidity
• CPC Class Codes: C08G 18/40 High-molecular-weight compounds C08G18/2805 takes precedence
• CPC Class Codes: C08G 18/4072 Mixtures of compounds of group C08G18/63 with other macromolecular compounds
• CPC Class Codes: C08G 18/48 Polyethers
• CPC Class Codes: C08G 18/4804 Two or more polyethers of different physical or chemical nature
• CPC Class Codes: C08G 18/4812 Mixtures of polyetherdiols with polyetherpolyols having at least three hydroxy groups
• CPC Class Codes: C08G 18/4825 Polyethers containing two hydroxy groups C08G18/4833 - C08G18/5096 take precedence
• CPC Class Codes: C08G 18/4829 Polyethers containing at least three hydroxy groups C08G18/4833 - C08G18/5096 take precedence
• CPC Class Codes: C08G 18/50 having heteroatoms other than oxygen
• CPC Class Codes: C08G 18/5021 having nitrogen
• CPC Class Codes: C08G 18/5024 containing primary and/or secondary amino groups
• CPC Class Codes: C08G 18/63 Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers
• CPC Class Codes: C08G 18/632 onto polyethers
• CPC Class Codes: C08G 18/73 acyclic
• CPC Class Codes: C08G 18/7671 containing only one alkylene bisphenyl group
• CPC Class Codes: C08G 18/7831 : containing biuret groups
• CPC Class Codes: C08G 2190/00 : Compositions for sealing or packing joints
• CPC Class Codes: C08K 5/12 : of cyclic polycarboxylic acids
• CPC Class Codes: C08K 5/17 : Amines; Quaternary ammonium compounds
• CPC Class Codes: C09J 175/08 : from polyethers
• CPC Class Codes: C09J 2475/00 : Presence of polyurethane
• CPC Class Codes: C09J 5/00 : Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers

Abstract

The adhesive system of the invention is especially useful in bonding replacement windows into vehicles. They allow for sufficient working time while still realizing a fast drive away time. The adhesive system is comprised of a moisture curable adhesive and a cure accelerator that may be applied using a simple single caulk gun and may be applied at ambient temperatures such as −10° C. and about 45° C. The cure accelerator is comprised of a polyol having a backbone that has at least one amine in the backbone. The moisture curable adhesive typically is comprised of an isocyanate terminated prepolymer.

Claims

1. An adhesive system comprised of a moisture curable adhesive comprised of an isocyanate terminated prepolymer and a plasticizer, and a separate cure accelerator comprised of a first polyol having a backbone comprised of at least one amino group characterized by an apparent pH of at least 10 and an average OH functionality of at least 2 to 4.5 and present in an amount of 5% to 50% by weight of the cure accelerator;

wherein the cure accelerator includes 20% to 80% by weight of the cure accelerator of a polyol not having an amino group, and the amount of any water in the cure accelerator is less than 1 weight percent, based on the total weight of the cure accelerator and the moisture curable adhesive;

wherein the adhesive system, upon curing, is substantially free c

wherein a volume ratio of the moisture curable adhesive to the cure accelerator is 5 to 200.

2. The adhesive system of claim 1, wherein the prepolymer is comprised of an isocyanate terminated polyether prepolymer, and the cure accelerator includes from 0 to 500 ppm water, based on the total weight of the cure accelerator and the moisture curable adhesive.

3. The adhesive system of claim 2, wherein the isocyanate terminated polyether prepolymer is comprised of a polyether backbone comprised of an ethylene oxide, a propylene oxide, or combination of these.

4. The adhesive system of claim 1,

wherein the first polyol having an amino group has an OH # of at least about 250.

5. The adhesive system of claim 1, wherein said first polyol has an OH # of at least 550.

6. The adhesive system of claim 1, wherein the moisture curable adhesive is further comprised of at least one of the following a filler and a catalyst.

7. The adhesive system of claim 6, wherein the plasticizer is linear, branched or combination thereof.

8. The adhesive system of claim 1, wherein the first polyol has an average OH functionality of at least 3.5 to 4.2.

9. The cure system of claim 1, wherein the amino groups are all tertiary amines.

10. The adhesive system of claim 4, wherein the cure accelerator includes 10 to 35 percent of one or more fillers based on the weight of the cure accelerator.

11. The adhesive system of claim 10, wherein the cure accelerator includes from 0 to 500 ppm water, based on the total weight of the cure accelerator and the moisture curable adhesive.

12. The adhesive system of claim 11, wherein the cure accelerator includes 0.01% to 2% catalyst, based on the total weight of the cure accelerator.

17. A method for adhering a first substrate to a second substrate with the adhesive system of claim 1 comprising the steps of:

a) providing the adhesive system including the moisture curable adhesive and the cure accelerator;

wherein the moisture curable adhesive and the cure accelerator are separately provided;

b) mixing the cure accelerator and the adhesive composition to form an adhesive mixture;

c) applying the adhesive mixture to at least a portion of the first substrate;

d) contacting the first substrate having the adhesive mixture thereon with the second substrate such that the adhesive mixture is therebetween; and

e) allowing the adhesive mixture to cure bonding said substrates together.

19. A structure comprising:

a first substrate adhered to an optically transparent substrate with the adhesive system of claim 1, wherein the adhesive system is cured and substantially free of bubbling.

13. An adhesive system

comprised of a moisture curable adhesive comprised of an isocyanate terminated prepolymer and a plasticizer, and a separate cure accelerator comprised of a polyol having a backbone comprised of about 3.0 to about 6 amino groups and an average OH functionality of at least 2 to 4.5;

wherein the polyol having an amino group has an apparent pH of at least 10;

wherein the cure accelerator includes 20% to 80% by weight of the cure accelerator of a polyol not having an amino group, and the amount of any water in the cure accelerator is sufficiently low so that bubbling is avoided upon curing the adhesive system;

wherein the adhesive system, upon curing, is substantially free of bubbles.

14. The adhesive system of claim 13, wherein the moisture curable adhesive and cure accelerator are provided in a volumetric ratio of moisture curable adhesive/cure accelerator of 5 to 200.

15. The adhesive system of claim 14, wherein said volumetric ratio is at most 20.

16. The adhesive system of claim 13, wherein the apparent pH is at least 11.

18. A method of adhering a first substrate and a second substrate with the adhesive system of claim 13 comprising the steps of:

a) providing the adhesive system including the moisture curable adhesive and the cure accelerator, wherein the moisture curable adhesive and cure accelerator are separately provided;

b) mixing the cure accelerator and the moisture curable adhesive to form an adhesive mixture;

c) applying the adhesive mixture to at least a portion of the first substrate;

d) contacting the first substrate having the adhesive mixture thereon with the second substrate such that the adhesive mixture is therebetween; and

e) allowing the adhesive mixture to cure bonding said substrates together.

20. A structure comprising:

a first substrate adhered to an optically transparent substrate with the adhesive system of claim 13, wherein the adhesive system is cured and substantially free of bubbling.