Composition including monomer with a carboxylic acid group, monomer with a hydroxyl group, and crosslinker and related articles and methods

Patent metadata

Field	Value
Publication number	US-11739172-B2
Application number	US-202117553473-A
Country	US
Kind code	B2
Filing date	Dec 16, 2021
Priority date	Dec 17, 2020
Publication date	Aug 29, 2023
Grant date	Aug 29, 2023

Abstract

The composition includes an acrylic monomer having a carboxylic acid group, an acrylic monomer having a hydroxyl group, and a compound composed of divalent segments L and at least two X groups. The divalent segments L are represented by the formula

Each divalent segment L is respectively directly bonded to two secondary N atoms, two tertiary N atoms, or a secondary and a tertiary N atom. Each R 1 represents an alkylene group having from 1 to 4 carbon atoms, and at least some of the R 1 groups are —CH 2 —CH 2 —CH 2 —CH 2 —. Each X group is independently represented by the formula CH 2 ═C(R)—C(O)—O—V-W—C(O)—. The acrylic monomer having a carboxylic acid group is present in an amount of at least 20 percent by weight, based on the total weight of acrylic-functional compounds. Articles and a method of using the composition are also described.

First claim

What is claimed is:

1. A composition comprising:
at least 20 percent by weight, based on the total weight of acrylic-functional compounds in the composition, of an acrylic monomer comprising a carboxylic acid group;
an acrylic monomer comprising a hydroxyl group; and
a compound comprising divalent segments L and at least two X groups, wherein the divalent segments L are represented by the formula:

wherein each divalent segment L is respectively directly bonded to:
i) two secondary N atoms, each directly bonded to a further divalent segment L or an X group, or
ii) two tertiary N atoms, each directly bonded to “p” further divalent segments L and (2−p) X groups, wherein “_p_” is 0, 1, or 2, or
iii) a secondary N atom directly bonded to a further divalent segment L or an X group; and a tertiary N atom directly bonded to “_p_” further divalent segments L and (2−p) X groups, wherein “_p_” is 0, 1, or 2,

wherein each R 1 independently represents an alkylene group having from 1 to 4 carbon atoms, with the proviso that at least some of the R 1 groups are —CH 2 —CH 2 —CH 2 —CH 2 —, wherein each “_n_” independently represents a positive integer, and wherein each X group is independently represented by the formula
CH 2 ═C(R)—C(O)—O—V-W—C(O)—

wherein each R is independently hydrogen or methyl, wherein each W is independently O, S, or NR 2 , wherein R 2 is hydrogen or alkyl having up to 4 carbon atoms, and wherein each V is independently alkylene that is optionally interrupted by at least one ether linkage or amine linkage and optionally substituted by hydroxyl.

2. The composition of claim 1 , wherein the acrylic monomer comprising the hydroxyl group is present in an amount of at least 25 percent by weight, based on the total weight of the acrylic-functional compounds in the composition.

3. The composition of claim 2 , wherein the compound comprising divalent segments L and at least two X groups is present in an amount in a range from 20 percent by weight to 35 percent by weight, based on the total weight of the acrylic-functional compounds in the composition.

4. The composition of claim 2 , further comprising a toughening agent.

5. The composition of claim 2 , further comprising filler.

6. The composition of claim 2 , packaged as a first part of a two-part adhesive composition, wherein a second part of the two-part adhesive composition comprises a free-radical initiator.

7. An adhesive comprising the composition of claim 2 at least partially cured with a free-radical initiator, wherein the adhesive has a glass transition temperature in a range from 100° C. to 150° C.

8. An article bonded with the composition of claim 2 at least partially cured with a free-radical initiator, wherein the article comprises polyamide.

9. A method of making a bonded article comprising a first substrate and a second substrate, the method comprising:
combining the composition of claim 1 with a free-radical initiator to provide an adhesive composition;
applying the adhesive composition on at least one of the first substrate or the second substrate;
adhering the first substrate and the second substrate using the adhesive composition; and
allowing the adhesive composition to at least partially cure to make the bonded article.

10. The method of claim 9 , wherein at least one of the first substrate or the second substrate comprises polyamide.

11. The composition of claim 1 , wherein the acrylic monomer comprising the hydroxyl group is present in an amount of at least 5 percent by weight and up to 20 percent by weight, based on the total weight of the acrylic-functional compounds in the composition.

12. The composition of claim 11 , further comprising at least one alkyl acrylate or alkyl methacrylate.

13. The composition of claim 11 , further comprising at least one of methyl methacrylate, lauryl methacrylate, or isobornyl methacrylate.

14. The composition of claim 11 , further comprising methyl methacrylate, lauryl methacrylate, and isobornyl methacrylate.

15. The composition of claim 11 , wherein the compound comprising divalent segments L and at least two X groups is present in an amount in a range from 20 percent by weight to 35 percent by weight, based on the total weight of the acrylic functional compounds in the composition.

16. The composition of claim 11 , further comprising a toughening agent.

17. The composition of claim 11 , further comprising filler.

18. The composition of claim 11 , packaged as a first part of a two-part adhesive composition, wherein a second part of the two-part adhesive composition comprises a free-radical initiator.

19. An adhesive comprising the composition of claim 11 at least partially cured with a free-radical initiator, wherein the adhesive has a glass transition temperature in a range from 100° C. to 150° C.

20. An article bonded with the composition of claim 11 at least partially cured with a free-radical initiator, wherein the article comprises polyamide.

Assignees

• 3M Innovative Properties Company

Inventors

• Rotto Nelson T
• Mahoney Wayne S
• Kropp Michael A
• Ostlund Anthony J
• Klimovica Kristine
• Spawn Carol-Lynn

Classifications

• C08F220/36 Primary

  containing oxygen in addition to the carboxy oxygen {, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate} · CPC title

• C08F220/06

  Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof · CPC title

• C08F220/14

  Methyl esters {, e.g. methyl (meth)acrylate} · CPC title

• C08F220/1811

  C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate · CPC title

• C08F220/1812

  C12-(meth)acrylate, e.g. lauryl (meth)acrylate · CPC title