IP Library › Granted Patent US 11,511,522
Granted Patent B2
US 11,511,522 · App. 16/486,993 · Granted Nov 29, 2022

High performance photocurable optically clear adhesive

Inventors: Lan Hong Liu (Rosemount, MN); Jianhui Xia (Woodbury, MN); Thomas P. Klun (Lakeland, MN); David A. Kowitz (St. Paul, MN); Audrey A. Sherman (Woodbury, MN)
Assignee: 3M Innovative Properties Company
B32B17/10A47G21/14A47L19/02B32B7/12B32B27/36C09J4/06C09J9/00B29C69/00B32B2255/10B32B2255/26B32B2307/412B32B2315/08B32B2367/00B32B2457/20
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Quick Facts
Patent No.
US 11,511,522
App. No.
16/486,993
Granted
Nov 29, 2022
Kind
B2
Abstract

The present invention is an optically clear, curable adhesive including a polyvinylbutyral, a polyurethane (meth)acrylate, a (meth)acrylate monomer, and a photoinitiator. The polyvinylbutyral has a dynamic viscosity of between about 9 and about 13 mPa·s and a polyvinyl alcohol weight percent of less than about 18%. The polyurethane (meth)acrylate includes the reaction product of a diol, at least one diisocyanate, and a hydroxyfunctional (meth)acrylate or an isocyanatofunctional (meth)acrylate. When the optically clear, curable adhesive is placed between two transparent substrates and made into a laminate, the laminate has a haze of less than about 6%, a transmission of greater than about 88%, and an optical clarity of greater than about 98% when cured. The optically clear, curable adhesive also has a peel adhesion of at least about 100 g/cm based on ASTM 3330 when cured.

Claims (41)

1. An optically clear, curable adhesive comprising:

a polyvinylbutyral having a dynamic viscosity of between about 9 and about 30 mPa·s and having a polyvinyl alcohol weight percent of between about 14% and about 21%;

a polyurethane (meth)acrylate comprising the reaction product of:

a diol;

at least one diisocyanate; and

a hydroxyfunctional (meth)acrylate or an isocyanatofunctional (meth)acrylate;

a (meth)acrylate monomer; and

a photoinitiator;

wherein when the optically clear, curable adhesive is placed between two transparent substrates and made into a laminate, the laminate has a haze of less than about 6%, a transmission of greater than about 88% and optical clarity of greater than about 98% when cured, and

wherein the optically clear, curable adhesive has a peel adhesion of at least about 100 g/cm based on ASTM 3330 when cured.

2. The optically clear, curable adhesive of claim 1 , wherein the diol is selected from one of a poly(tetramethylene oxide) diol having a number average molecular weight of about 2,000 g/mol or less, a poly(propylene oxide) diol having a number average molecular weight of about 2,000 g/mol or less, and a polycaprolactone diol having a number average molecular weight of about 2,000 g/mol or less.

3. The optically clear, curable adhesive of claim 1 , wherein the at least one diisocyanate is an aliphatic diisocyanate.

4. The optically clear, curable adhesive of claim 1 , further comprising a hydroxyfunctional monomer with an aromatic moiety.

5. The optically clear, curable adhesive of claim 1 , wherein the polyvinylbutyral has a weight average molecular weight between about 10,000 g/mol and about 25,000 g/mol.

6. The optically clear, curable adhesive of claim 1 , wherein the polyurethane (meth)acrylate has a weight average molecular weight between about 2,745 g/mol and about 63,000 g/mol.

7. The optically clear, curable adhesive of claim 1 , wherein the polyvinylbutyral has a polyvinyl acetate weight percent of between about 1% and about 8%.

8. The optically clear, curable adhesive of claim 1 , wherein the optically clear, curable adhesive comprises between about 30% and about 70% by weight polyvinylbutyral.

9. The optically clear, curable adhesive of claim 1 , wherein the optically clear, curable adhesive comprises between about 10% and about 60% by weight polyurethane (meth)acrylate.

10. The optically clear, curable adhesive of claim 1 , wherein the optically clear, curable adhesive comprises between about 10% and about 60% by weight (meth)acrylate monomer.

11. The optically clear, curable adhesive of claim 1 , wherein the (meth)acrylate monomer comprises at least one of monofunctional or difunctional acrylates.

12. An optically clear laminate comprising:

a first substrate;

a second substrate; and

an optically clear, curable adhesive positioned between the first substrate and the second substrate, the optically clear, curable adhesive comprising:

a polyvinylbutyral having a dynamic viscosity of between about 9 and about 30 mPa·s and having a polyvinyl alcohol weight percent of between about 14% and about 21%;

a polyurethane (meth)acrylate comprising the reaction product of:

a diol;

at least one diisocyanate; and

a hydroxyfunctional (meth)acrylate or an isocyanatofunctional (meth)acrylate;

a (meth)acrylate monomer; and

a photoinitiator;

wherein when the optically clear, curable adhesive is placed between two transparent substrates and made into a laminate, the laminate has a haze of less than about 6%, a transmission of greater than about 88% and optical clarity of greater than about 98% when cured, and

wherein the optically clear, curable adhesive has a peel adhesion of at least about 100 g/cm based on ASTM 3330 when cured.

13. The optically clear laminate of claim 12 , wherein the diol is selected from one of a poly(tetramethylene oxide) diol having a number average molecular weight of about 2,000 g/mol or less, a poly(propylene oxicde) diol having a number average molecular weight of about 2,000 g/mol or less and a polycaprolactone diol having a number average molecular weight of about 2,000 g/mol or less.

14. The optically clear laminate of claim 12 , wherein the at least one diisocyanate is an aliphatic diisocyanate.

15. The optically clear laminate of claim 12 , wherein the polyvinylbutyral has a weight average molecular weight between about 10,000 g/mol and about 25,000 g/mol.

16. The optically clear laminate of claim 12 , wherein the polyurethane (meth)acrylate has a weight average molecular weight between about 2,745 g/mol and about 63,000 g/mol.

17. The optically clear laminate of claim 12 , wherein the polyvinylbutyral has a polyvinyl acetate weight percent of between about 1% and about 8%.

18. The optically clear laminate of claim 12 , wherein the optically clear, curable adhesive comprises between about 30% and about 70% by weight polyvinylbutyral.

19. The optically clear laminate of claim 12 , wherein the optically clear, curable adhesive comprises between about 10% and about 60% by weight polyurethane (meth)acrylate.

20. The optically clear laminate of claim 12 , wherein the optically clear, curable adhesive comprises between about 10% and about 60% by weight (meth)acrylate monomer.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2021
From: LIU, LAN HONG; XIA, JIANHUI; KLUN, THOMAS P.; KOWITZ, DAVID A.; SHERMAN, AUDREY A.
To: 3M INNOVATIVE PROPERTIES COMPANY
Reel/Frame 055032/0419 →
Continuity (2)
Provisional Application 62466664 · Mar 3, 2017
Related Publication 20200017720A1 · Jan 16, 2020
Cited By (1)
US 12,600,885