Curable and cured adhesive compositions

• US 10,941,321 B2
• Filed: 09/12/2016
• Issued: 03/09/2021
• Est. Priority Date: 09/30/2015
• Status: Active Grant

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Behling, Ross E., Clapper, Jason D., Everaerts, Albert I., Ting, Chun-Yi, Ellis, Mark F., Benson, Karl E., Xia, Jianhui
• Primary Examiner(s): Desai, Anish P
• Application Number:
  US15/761,997
• Publication Number:
  US 20180265748A1
• Time in Patent Office: 1,639 Days
• CPC Class Codes: C08F 216/36 by a ketonic radical
• CPC Class Codes: C08F 220/1804 C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
• CPC Class Codes: C08F 220/1806 C6-(meth)acrylate, e.g. (cyclo)hexyl (meth)acrylate or phenyl (meth)acrylate
• CPC Class Codes: C08F 220/1808 C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
• CPC Class Codes: C08F 220/1818 C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
• CPC Class Codes: C08F 220/20 of polyhydric alcohols or phenols , e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
• CPC Class Codes: C08F 220/301 and one oxygen in the alcohol moiety
• CPC Class Codes: C08F 220/36 containing oxygen in addition to the carboxy oxygen , e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
• CPC Class Codes: C08F 220/56 Acrylamide; Methacrylamide
• CPC Class Codes: C08F 265/04 on to polymers of esters
• CPC Class Codes: C08F 2810/20 leading to a crosslinking, either explicitly or inherently
• CPC Class Codes: C08J 2333/10 Homopolymers or copolymers of methacrylic acid esters
• CPC Class Codes: C08J 3/24 Crosslinking, e.g. vulcanising, of macromolecules mechanical aspects B29C35/00; crosslinking agents C08K
• CPC Class Codes: C09J 2203/326 for bonding electronic components such as wafers, chips or semiconductors
• CPC Class Codes: C09J 2301/414 presence of a copolymer
• CPC Class Codes: C09J 2433/00 Presence of (meth)acrylic polymer
• CPC Class Codes: C09J 7/385 Acrylic polymers
• CPC Class Codes: C09J 7/405 characterised by the substrate of the release liner
• CPC Class Codes: Y10T 428/2891 including addition polymer from alpha-beta unsaturated carboxylic acid [e.g., acrylic acid, methacrylic acid, etc.] Or derivative thereof

Abstract

Curable adhesive compositions are provided that can be cured using ultraviolet or visible light radiation. These curable adhesive compositions, which contain a curable (meth)acrylate copolymer, have a creep compliance that is less than 5(10⁻⁴) inverse Pascals at 25° C., a creep compliance that is greater than 1(10⁻³) inverse Pascals at 70° C., and a shear storage modulus greater than 40 kiloPascals when measured at 25° C. at a frequency of 1 radian/second.

Claims

1. A curable adhesive composition comprising (1) a curable (meth)acrylate copolymer having a weight average molecular weight in a range of 150,000 to 400,000 Da and (2) an optional photoinitiator, wherein the curable (meth)acrylate copolymer comprises:

a) a first monomeric unit of Formula (I) in an amount in a range of 50 to 94 weight percent based on a total weight of monomeric units in the curable (meth)acrylate copolymer

2. The curable adhesive composition of claim 1, wherein the curable (meth)acrylate copolymer further comprises a fifth monomeric unit that is a nitrogen-containing monomeric unit not of Formula (II).

3. The curable adhesive composition of claim 1, wherein the curable (meth)acrylate copolymer is free or substantially free of monomeric units derived from an acidic monomer, a vinyl ester monomer, or an anhydride-containing monomer.

4. The curable adhesive composition of claim 1, wherein the curable (meth)acrylate copolymer has a glass transition temperature equal to at least −

15°

C. when measured using Dynamic Mechanical Analysis at a frequency of 1 radian/second.

5. A cured adhesive composition comprising a cured (meth)acrylate copolymer, the cured adhesive composition being a reaction product resulting from exposing a curable adhesive composition to ultraviolet or visible light radiation, wherein the curable adhesive composition is of claim 1.

6. The cured adhesive composition of claim 5, wherein the cured adhesive composition is optically clear.

7. An article comprising a first substrate and a layer of the curable adhesive composition of claim 1 positioned adjacent to the first substrate.

8. The article of claim 7, wherein the layer of the curable adhesive composition is a die-cut film.

9. The article of claim 7, wherein the first substrate is a release liner.

10. The article of claim 8, wherein the article further comprises a second substrate and the die-cut film is positioned between the first substrate that is the release liner and a second substrate, the second substrate being a second release liner or an optical substrate.

11. An article comprising a first substrate, a second substrate, and a layer of the cured adhesive composition of claim 5, wherein the layer of the cured adhesive composition is positioned between the first substrate and the second substrate.

12. A method of preparing an article, the method comprising:

providing a first substrate, a second substrate, and a curable adhesive composition layer of claim 1;

forming a laminate comprising the first substrate, the second substrate, and the curable adhesive composition layer, wherein the curable adhesive composition layer is positioned between the first substrate and the second substrate; and

exposing the curable adhesive composition layer to ultraviolet or visible light radiation to form a cured adhesive composition layer.

13. The method of claim 12, wherein at least one of the first substrate and the second substrate has at least one feature and wherein forming the laminate comprises flowing the curable adhesive composition to cover an outer surface of the feature.

14. The method of claim 12, wherein the curable adhesive composition layer is cut with a die to have dimensions suitable for positioning between the first substrate and the second substrate.