Liquid optical adhesive compositions

Patent metadata

Field	Value
Publication number	US-9890304-B2
Application number	US-201314437214-A
Country	US
Kind code	B2
Filing date	Nov 26, 2013
Priority date	Dec 10, 2012
Publication date	Feb 13, 2018
Grant date	Feb 13, 2018

Abstract

The disclosure describes a curable composition comprising a first oligomer having a plurality of polymerizable groups; a second component comprising alkylene oxide repeat units and terminal polymerizable groups, a solvent monomer component; and a photoinitiator. The curable composition may be used as an adhesive in optical applications.

First claim

What is claimed is:

1. A curable adhesive composition comprising:
a) a first oligomer comprising;
i. greater than 50 parts by weight of (meth)acrylate ester monomer units derived from alkanols having an average carbon number of C 4 -C 18 ,
ii. hydroxyl-functional monomer units,
iii. monomer units having polymerizable groups wherein the polymerizable groups are pendent (meth)acrylate groups or terminal aryl ketone photoinitiator groups,

b) a second component having the general formula:

wherein R1 is hydrogen or methyl,
R2 is alkylene, arylene, or alkarylene,
for each m, R4 is independently a C 2 -C 4 alkylene oxide repeat units,
m ranges from 5 to 100; and
R3 is independently a residue of a diisocyanate, n=1 and
c) a diluent monomer component.

2. The curable adhesive composition of claim 1 wherein the polymerizable groups of the monomers units of the first oligomer are free-radically photopolymerizable groups.

3. The curable adhesive composition of claim 1 wherein R4 is C 3 alkylene oxide repeat units.

4. The curable adhesive composition of claim 1 wherein the second component has a number average molecular weight of no greater than 15,000 g/mole.

5. The curable adhesive composition of claim 1 wherein R3 independently comprises the residue of a cyclic aliphatic diisocyanate.

6. The curable adhesive composition of claim 1 wherein the adhesive composition comprises greater than 50 wt. % of the first oligomer and 0.5 to 50 wt-% of the second component.

7. The curable adhesive composition of claim 1 comprising less than 20 wt-% of the diluent monomer component.

8. The curable adhesive composition of claim 1 wherein the hydroxyl functional monomer has the general formula:

wherein
R 5 is a (hetero)hydrocarbyl group;
R 4 is —H or C 1 -C 4 alkyl; and
X 1 is —NR 4 — or —O—.

9. The curable adhesive composition of claim 1 wherein the monomer units having polymerizable group are pendent (meth)acrylate groups prepared by reaction of an oligomer having pendent hydroxyl functional groups with an acryloyl compound having co-reactive functional groups.

10. The curable adhesive composition of claim 1 wherein the monomer units having polymerizable groups comprise a (meth)acrylate compound comprising the terminal aryl ketone photoinitiator groups.

11. The curable adhesive composition of claim 1 wherein the first oligomer comprises 3 to 49 parts by weight of the hydroxyl-functional monomer units and 1 to 10 parts by weight of the monomer units having polymerizable groups.

12. The curable adhesive composition of claim 1 wherein the diluent monomer component comprises at least one monomer selected from acrylate ester monomer units, hydroxyl-functional monomer units, polar monomer units, silane-functional monomer units, and mixtures thereof.

13. The curable adhesive composition of claim 1 wherein the adhesive composition further comprises at least one component selected from photoinitiator, thermal initiator, additives, plasticizers, and tackifiers.

14. The curable adhesive composition of claim 1 wherein the first oligomer has a M w of 5,000 g/mole to 50,000 g/mole.

15. The curable adhesive composition of claim 1 , wherein the R3 is

wherein R5 is independently hydrogen or methyl.

Assignees

• 3M Innovative Properties Co
• 3M Innovative Properties Co

Inventors

• Yurt Serkan
• Clapper Jason D
• Behling Ross E
• Campbell Christopher J
• Ellis Mark F
• Krepski Larry R
• Fornof Ann R
• Gaddam Babu N
• Dizio James P

Classifications

• C09J133/14

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title

• C09J133/066

  containing -OH groups · CPC title

• C08F220/343

  in the form of urethane links · CPC title

• C09J133/08 Primary

  Homopolymers or copolymers of acrylic acid esters · CPC title

• C08L2312/00

  Crosslinking · CPC title