IP Library Granted Patent US 11,499,075
Granted Patent B2
US 11,499,075 · App. 16/636,430 · Granted Nov 15, 2022

Isocyanate functional adhesive which bonds primerless to silanated acrylic polyol based coatings

Inventors: Dietmar Golombowski (Horgen, CH); Andreas Lutz (Freienbach, CH); Stefan Schmatloch (Freienbach, CH); Huide D. Zhu (Auburn Hills, MI)
Assignee: DDP SPECIALTY ELECTRONICS MATERIALS US, LLC
C09J175/08C08G18/10C08G18/4812C08G18/7671C08K13/02C08K2201/006
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Quick Facts
Patent No.
US 11,499,075
App. No.
16/636,430
Granted
Nov 15, 2022
Kind
B2
Abstract

Disclosed is a composition including one or more isocyanate functional prepolymers; one or more catalysts for the reaction of isocyanate moieties and active hydrogen containing moieties; one or more mercapto silanes; one or more amino silanes, isocyanato silanes or a mixture thereof; one or more reinforcing fillers comprising one or more high surface area carbon blacks; one or more untreated calcium carbonates; one or more polyisocyanates having an isocyanate functionality of about 2 or greater; and one or more linear plasticizers. Preferably, the isocyanate functional prepolymer is prepared in the presence of at least a portion of the linear plasticizer. Preferably, the isocyanate functional polymer is prepared in the presence of a dialkyl malonate. The composition may be one-part adhesive composition. Also disclosed are methods of applying the compositions to substrates. The composition bonds primerlessly to hard to bond to coatings, such as coatings prepared from compositions including a silanated component, such as a silanated acrylopolyols, or having silica clusters.

Claims (28)

1. A composition comprising:

a) one or more isocyanate functional prepolymers;

b) one or more catalysts for the reaction of isocyanate moieties and active hydrogen containing moieties;

c) 0.6 to about 1.1 percent by weight of one or more mercapto silanes, based on the weight of the composition;

d) 0.1 to 1.3 percent by weight of one or more amino silanes, isocyanato silanes or a mixture thereof, based on the weight of the composition;

e) one or more reinforcing fillers comprising one or more high surface area carbon blacks;

f) one or more untreated calcium carbonates;

g) one or more polyisocyanates having an isocyanate functionality of about 2 or greater; and

h) a linear plasticizer, wherein the isocyanate functional prepolymer is prepared in the presence of the linear plasticizer and/or the plasticizer is added after preparing the isocyanate functional prepolymer;

wherein the composition optionally includes a dialkyl malonate.

2. A composition according to claim 1 , wherein the composition includes the dialkyl malonate and the isocyanate functional prepolymer is prepared in the presence of at least a portion of the dialkyl malonate.

3. A composition according to claim 1 , wherein the composition comprises one or more amino silanes.

4. A composition according to claim 1 , wherein the amino silane has one secondary amine.

5. A composition according to claim 1 wherein the amino silane is a bis(di or tri alkoxy silyl alkyl) amine.

6. A composition according to claim 1 wherein the reinforcing filler has an oil absorption number of about 80 to about 120 g/100 ml.

7. A composition according to claim 1 , wherein the dialkyl malonate is present in an amount of about 0.05 to about 1 percent by weight of the composition.

8. A composition according to claim 1 , wherein the linear plasticizer is a linear phthalate.

9. A composition according to claim 1 , wherein the one or more polyisocyanates having an isocyanate functionality of about 2.0 or greater comprises a trimer of an aliphatic polyisocyanate, a polymeric MDI or a mixture thereof.

10. A composition according to claim 1 , wherein the one or more polyisocyanates having an isocyanate functionality of about 2.0 or greater comprises a trimer of an aliphatic polyisocyanate.

11. A composition according to claim 1 , which comprises:

a) from about 30 to about 65 percent by weight of the one or more isocyanate functional prepolymers (preferably prepared in the presence of a linear plasticizer and a dialkyl malonate) including any linear plasticizer and any dialkyl malonate in the isocyanate prepolymers (preferably the one or more isocyanate functional prepolymers includes a portion having one or more isocyanate groups in an amount of about 22 percent by weight to about 55 percent by weight;

b) from about 0.03 to about 1.6 percent by weight of the one or more catalysts for the reaction of isocyanate moieties and active hydrogen containing moieties;

c) from about 0.3 to about 1.5 percent by weight of the one or more mercapto silanes;

d) from about 0.4 to about 2.0 percent by weight of the one or more amino silanes, isocyanato silanes, or a mixture thereof;

e) from about 15 to about 30 percent by weight of the one or more reinforcing fillers comprising one or more high surface area carbon blacks; and

f) from about 8 to about 20 percent by weight of the one or more untreated calcium carbonates; and

g) from greater than 0 to about 3 percent by weight of the one or more polyisocyanates having an isocyanate functionality of about 2.0 or greater; and

the dialkyl malonate is present in an amount of about 0.05 to about 1 percent by weight, all percentages are based on the weight of the composition.

Assignments (6)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 1, 2021
From: GOLOMBOWSKI, DIETMAR; LUTZ, ANDREAS; SCHMATLOCH, STEFAN
To: DOW EUROPE GMBH
Reel/Frame 055444/0346 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 1, 2021
From: ZHU, HUIDE D.
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 055444/0435 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 1, 2021
From: DOW EUROPE GMBH
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 055444/0564 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 1, 2021
From: DOW GLOBAL TECHNOLOGIES LLC
To: THE DOW CHEMICAL COMPANY
Reel/Frame 055451/0474 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 1, 2021
From: THE DOW CHEMICAL COMPANY
To: DDP SPECIALTY ELECTRONIC MATERIALS US, INC.
Reel/Frame 055452/0432 →
CHANGE OF NAME Recorded Mar 1, 2021
From: DDP SPECIALTY ELECTRONIC MATERIALS US, INC.
To: DDP SPECIALTY ELECTRONIC MATERIALS US, LLC
Reel/Frame 055527/0298 →
Continuity (2)
Provisional Application 62565514 · Sep 29, 2017
Related Publication 20200339847A1 · Oct 29, 2020