Adhesion promoters for curable compositions

Patent metadata

Field	Value
Publication number	US-11168237-B2
Application number	US-201917250156-A
Country	US
Kind code	B2
Filing date	Jun 12, 2019
Priority date	Jun 14, 2018
Publication date	Nov 9, 2021
Grant date	Nov 9, 2021

Abstract

Adhesion promoters, Curable compositions containing the adhesion promoters, cured compositions that are formed from the curable compositions, and articles containing the cured compositions are provided. The adhesion promoter has at least one epoxide group and a plurality of hydrolyzable silyl groups. The curable compositions include an adhesion promoter, an epoxy resin, and a curing agent for the epoxy resin that has at least two amino groups that are primary and/or secondary amino groups.

First claim

What is claimed is:

1. An adhesion promoter having at least one epoxide group and a plurality of hydrolyzable silyl groups, the adhesion promoter being a ring-opened adduct of
a) a polyepoxide comprising at least three epoxide groups;
b) an aminosilane of Formula (I)
HN(R 1 )(Z 1 —Si(L 1 ) x (L 2 ) 3-x )  (I)

wherein
R 1 is alkyl, or a group of formula —Z 1 —Si(L 1 ) x (L 2 ) 3-x ;
L 1 is a hydrolyzable group;
L 2 is an alkyl;
x is an integer equal to 1, 2, or 3;
Z 1 is a divalent linking group having 1 to 12 carbon atoms; and

c) an isocyanato silane of Formula (II)
O═C═N—Z 2 —Si(L 3 ) y (L 4 ) 3-y   (II)

wherein
L 3 is a hydrolyzable group;
L 4 is an alkyl;
y is an integer equal to 1, 2, or 3;
Z 2 is a divalent linking group having 1 to 12 carbon atoms.

2. The adhesion promoter of claim 1 , wherein the adhesion promoter has at least one group of Formula (III)
—CH[O—(CO)—NH—Z 2 —Si(L 3 ) y (L 4 ) 3-y ]—CH 2 —N(R 1 )(Z 1 —Si(L 1 ) x (L 2 ) 3-x )  (III)

where groups R 1 , Z 1 , Z 2 , L 1 , L 2 , L 3 , L 4 , x, and y are the same as defined in Formula (I) and Formula (II).

3. The adhesion promoter of claim 2 , wherein Formula (III) is of Formula (III-A)
—CH[O—(CO)—NH—Z 2 —Si(L 3 ) 3 ]—CH 2 —N(R 1 )(Z 1 —Si(L 1 ) 3 )  (III-A)

where groups R 1 , Z 1 , Z 2 , L 1 , and L 3 are the same as defined in Formula (III).

4. A curable composition comprising:
a curable component comprising
an adhesion promoter having at least one epoxide group and a plurality of silyl groups, the adhesion promoter being a ring-opened adduct of
a) a polyepoxide comprising at least two three epoxide groups;
b) an aminosilane of Formula (I)
HN(R 1 )(Z 1 —Si(L 1 ) x (L 2 ) 3-x )  (I)

wherein
R 1 is alkyl, or a group of formula —Z 1 —Si(L 1 ) x (L 2 ) 3-x ;
L 1 is a hydrolyzable group;
L 2 is an alkyl;
x is an integer equal to 1, 2, or 3;
Z 1 is a divalent linking group having 1 to 12 carbon atoms;

c) an isocyanato silane of Formula (II)
O═C═N—Z 2 —Si(L 3 ) y (L 4 ) 3-y   (II)

wherein
L 3 is a hydrolyzable group;
L 4 is an alkyl;
y is an integer equal to 1, 2, or 3; and
Z 2 is a divalent linking group having 1 to 12 carbon atoms;

an epoxy resin having at least two epoxide groups; and
a curing agent for the epoxy resin, the curing agent having at least two amino groups that are primary and/or secondary amino groups.

5. The curable composition of claim 4 , wherein the curable composition comprises a first part and a second part with the curing agent being in the first part and the adhesion promoter and the epoxy resin being in the second part.

6. The curable composition of claim 4 , wherein moles of reactive amine hydrogens (—N—H groups) to moles of epoxide groups is in a range of 1.5:1 to 1:1.5.

7. The curable composition of claim 4 , wherein the curable component comprises up to 80 weight percent epoxy resin, 0.1 to 10 weight percent adhesion promoter, and up to 60 weight percent curing agent.

8. The curable composition of claim 4 , wherein the curable composition comprises 60 to 100 weight percent curable component and 0 to 40 weight percent inorganic filler.

9. A cured composition comprising a cured reaction product of the curable composition of claim 4 .

10. An article comprising a first substrate and the cured composition of claim 9 positioned adjacent to the first substrate.

11. The article of claim 10 , further comprising a second substrate and wherein the cured composition is positioned between the first substrate and the second substrate.

12. The article of claim 10 , wherein the first substrate and/or the second substrate has groups that react with the hydrolyzable silyl groups of the adhesion promoter to form a covalent bond bonding the adhesion promoter to the first substrate and/or to the second substrate.

13. A dispenser comprising a first chamber and a second chamber,
the first chamber comprising a curing agent for an epoxy resin having at last two epoxide groups, the curing agent having at least two amino groups that are primary and/or secondary amino groups; and
the second chamber comprising the epoxy resin having at least two epoxide groups and an adhesion promoter having at least one epoxide group and a plurality of silyl groups, the adhesion promoter being a ring opened adduct of
1) a polyepoxide comprising at least three epoxide groups;
2) an aminosilane of Formula (I)
HN(R 1 )(Z 1 —Si(L 1 ) x (L 2 ) 3-x )  (I)

wherein
R 1 is alkyl, or a group of formula —Z 1 —Si(L 1 ) x (L 2 ) 3-x ;
L 1 is a hydrolyzable group;
L 2 is an alkyl;
x is an integer equal to 1, 2, or 3; and
Z 1 is a divalent linking group having 1 to 12 carbon atoms;

3) an isocyanato silane of Formula (II)
O═C═N—Z 2 —Si(L 3 ) y (L 4 ) 3-y   (II)

wherein
L 3 is a hydrolyzable group;
L 4 is an alkyl;
y is an integer equal to 1, 2, or 3; and
Z 2 is a divalent linking group having 1 to 12 carbon atoms.

Assignees

• 3M Innovative Properties Co

Inventors

• Lee Hae-Seung H
• Schlechte Jay S

Classifications

• C09J163/00 Primary

  Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins · CPC title

• C08G18/718

  containing silicon · CPC title

• C08G59/4014

  Nitrogen containing compounds · CPC title

• C08G59/3281

  containing silicon · CPC title

• C08K5/5445

  containing at least one Si-N bond · CPC title