Crosslinkers and curable compositions including the same

Patent metadata

Field	Value
Publication number	US-12378340-B2
Application number	US-202017619195-A
Country	US
Kind code	B2
Filing date	Jun 10, 2020
Priority date	Jun 13, 2019
Publication date	Aug 5, 2025
Grant date	Aug 5, 2025

Abstract

Provided are novel crosslinkers and curable compositions including such crosslinkers. Bonded constructions including the disclosed curable compositions display high adhesion, elongation, and impact resistance even if the bonded substrate receives no surface treatment prior to bonding. Provided are elastomeric products including the curable compositions, methods of making the same, and uses thereof.

First claim

What is claimed is:

1. A crosslinker comprising:
a compound represented by the formula:
LR 1 q

wherein each R 1 is independently selected from a functional group represented by the formula:

wherein:
each R 2 is independently hydrogen or methyl;
n is an integer from 1 to 5, inclusive;
X is O, S, or NH; and
Y is a single bond or a divalent group represented by the formula:

wherein:
N′ is a nitrogen bonded to the carbonyl carbon of R 1 ; and
T is a divalent group selected from the group consisting of a linear alkylene, a cyclic alkylene, an unsubstituted arylene, a substituted arylene, and combinations thereof;
q is an integer of at least 2; and
L is an q-valent organic polymer comprising:
a monomer unit a) represented by the formula:

wherein R 3 is a hydrogen or a Z-terminated alkyl or heteroalkylene chain, wherein each Z-terminated chain may independently include a linkage selected from the group consisting of a secondary amino linkage, a tertiary amino linkage, an ether linkage, and combinations thereof, and wherein each Z is independently O, S, or NH; and
a monomer unit b) represented by the formula:

wherein n is an integer from 1 to 5, inclusive, each R 4 is independently hydrogen or alkyl, and each Z is independently O, S, or NH.

2. The crosslinker of claim 1 , wherein the q-valent organic polymer L has a number average molecular weight of from 4000 to 54000 grams per mole versus a polystyrene standard.

3. A curable composition comprising:
a monofunctional monomer;
a cure initiator system; and
the crosslinker of claim 1 .

4. The curable composition of claim 3 , wherein the monofunctional monomer is selected from the group consisting of methyl methacrylate, 2-hydroxyethyl methacrylate, methacrylic acid, 2-(2-butoxyethoxy)ethyl methacrylate, glycerol formal methacrylate, lauryl methacrylate, cyclohexyl methacrylate, phenyl methacrylate, and combinations thereof.

5. The curable composition of claim 3 , wherein the q-valent organic polymer L further comprises a monomer unit selected from the group consisting of monomer units represented by the formulas:

and combinations thereof, wherein
each R 6 is independently a hydrogen, a monomer unit selected from the group consisting of monomer units a)-e) and a Z-terminated alkyl chain, wherein the Z-terminated alkyl chain may include a linkage selected from the group consisting of a secondary amino linkage, a tertiary amino linkage, an ether linkage, and combinations thereof, and wherein Z is O, S, or NH.

6. The curable composition of claim 3 , wherein the q-valent organic polymer L further comprises a monomer unit represented by the formula:

wherein T is a divalent group selected from the group consisting of a linear alkylene, a cyclic alkylene, an unsubstituted arylene, a substituted arylene, and combinations thereof.

7. The curable composition of claim 3 , the composition further comprising a filler selected from the group consisting of a micro-fibrillated polyethylene, a fumed silica, talc, a wollastonite, an aluminosilicate clay, a phlogopite mica, calcium carbonate, a kaolin clay, and combinations thereof.

8. An elastomeric product prepared from at least one of the crosslinker of claim 1 , wherein the elastomeric product has a minimum ultimate elongation of at least 50%.

9. A method of bonding a first substrate to a second substrate, the method comprising:
mixing the curable composition of claim 3 with an accelerator to form an adhesive composition;
applying the adhesive composition to at least a portion of one surface of the first substrate;
covering the adhesive composition at least partially with at least a portion of one surface of the second substrate; and
allowing the adhesive composition to cure.

10. The method of claim 9 , wherein the portion of one surface of the first substrate is not subjected to a surface treatment before applying the adhesive composition thereto.

11. A bonded article comprising the elastomeric product of claim 8 bonded to a substrate.

12. The bonded article of claim 11 , comprising a glass lens bonded to a metal body using the elastomeric product.

13. A method of debonding a first substrate bonded to a second substrate with a bead of the elastomeric product of claim 8 , the method comprising:
pulling the bead away from at least one of the first or second substrates, wherein the bead stretchably releases from at least one of the first substrate or the second substrate.

14. The method of claim 13 , further comprising:
heating at least one of the elastomeric product, the first substrate, or the second substrate before pulling the bead away from at least one of the first substrate or the second substrate.

15. The method of claim 13 , further comprising pulling a non-metallic string through the elastomeric product between the first substrate and the second substrate to separate the first substrate and the second substrate.

16. The curable composition of claim 3 , wherein the q-valent organic polymer L comprises at least 70 wt. % of monomer unit b) monomers.

17. The curable composition of claim 3 , wherein the q-valent organic polymer L comprises 10 wt. % to 20 wt. % of monomer unit a) monomers.

18. The crosslinker of claim 1 , wherein the q-valent organic polymer L comprises at least 70 wt. % of monomer unit b) monomers.

19. The crosslinker of claim 1 , wherein the q-valent organic polymer L comprises 10 wt. % to 20 wt. % of monomer unit a) monomers.

20. The crosslinker of claim 1 , wherein Y is a single bond.

Assignees

• 3M Innovative Properties Company

Inventors

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

Classifications

• C09J4/06 Primary

  {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00 · CPC title

• C08K3/346

  Clay · CPC title

• C08K3/04

  Carbon · CPC title

• C08F220/20

  of polyhydric alcohols or phenols {, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate} · CPC title

• C08F222/1065

  of alcohol terminated (poly)urethanes, e.g. urethane(meth)acrylates · CPC title