IP Library Granted Patent US 9,120,958
Granted Patent B2
US 9,120,958 · App. 13/816,988 · Granted Sep 1, 2015

Ultra-violet curable adhesive

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Quick Facts
Patent No.
US 9,120,958
App. No.
13/816,988
Granted
Sep 1, 2015
Kind
B2
Abstract

An adhesive may be formulated with a functional component that reacts in the presence of ultraviolet light with a neighboring functional component to form a nonreversible bond therebetween. The functional component may include at least one —C═C— functional group that is able to undergo dimerization with a neighboring component. A method for making the adhesive includes covalently bonding the functional component to a support polymer, wherein the functional component may be covalently bonded to the support polymer by a linking molecule. A kit containing the adhesive and an ultraviolet light source is also provided.

Claims (52)

1. An ultraviolet curable adhesive composition comprising;

components of formula

R-(L-X) n ,

wherein:

n is greater than or equal to 1;

R comprises a macromolecular polymer selected from the group consisting of cellulose, lignin, hemi-cellulose, chitin, dextran, starch, glycogen, pectin, inulin, and derivatives thereof and combinations thereof;

X comprises a heterocyclic compound comprising a functional group capable of dimerization with a neighboring X when exposed to ultraviolet light of an intensity sufficient for dimerization of the functional groups; and

L comprises a linking component for covalently bonding X to R.

2. The adhesive of claim 1 , wherein the functional group comprises at least one —C═C—.

3. The adhesive of claim 2 , wherein X comprises at least one of a diazine, diazine derivatives, and combinations thereof.

4. The adhesive of claim 2 , wherein X comprises at least one of pyridine, pyrazine, pyrimidine, pyridazine, and derivatives thereof and combinations thereof.

5. The adhesive of claim 1 , wherein X comprises at least one of thymine, uracil, cytosine, and derivatives thereof and combinations thereof.

6. The adhesive of claim 1 , wherein the adhesive has a fluidity prior to curing and a pliability after curing, the substantially linear molecular constituent has a length, and the length provides:

a correlated degree of fluidity to the pre-cured adhesive with longer length providing decreased fluidity; and

a correlated degree of pliability to the cured adhesive with longer length providing increased pliability.

7. An ultraviolet curable adhesive composition comprising components of formula

R-(L-X) n ,

wherein:

n is greater than or equal to 1;

R comprises a macromolecular polymer;

X comprises a heterocyclic compound comprising a functional group capable of dimerization with a neighboring X when exposed to ultraviolet light of an intensity sufficient for dimerization of the functional groups; and

L is a linking component for covalently bonding X to R, and L comprises at least one of substituted or unsubstituted linear alkenyls, and substituted or unsubstituted linear polyethers.

8. The adhesive of claim 7 , wherein L comprises at least one of polyoxymethylene, polyoxyethylene, polyoxypropylene, polytetrahydrofuran, and derivatives thereof and combinations thereof.

9. The adhesive of claim 8 , wherein:

X comprises at least one of thymine, uracil, cytosine, and derivatives thereof and combinations thereof;

R comprises at least one of cellulose, hemicellulose, lignin, and derivatives thereof and combinations thereof; and

L comprises —[CH 2 CH 2 O] m — wherein m≧1.

10. The adhesive of claim 7 , wherein:

the adhesive has a fluidity and a pliability; and

each L comprises at least one of —[CH 2 O] m —, —[CH 2 CH 2 O] m —, —[CH 2 CH 2 CH 2 O] m —, and —[CH 2 CH 2 CH 2 CH 2 O] m —, and combinations thereof, wherein m≧1, and increasing m correlates to decreased fluidity and increased pliability.

11. The adhesive of claim 7 , wherein L comprises —[CH 2 CH 2 O] m — wherein m is greater than or equal to 1 and less than or equal to about 50.

12. The adhesive of claim 1 , further comprising a preservative mixed with the components of formula R-(L-X) n , wherein the preservative comprises at least one of sodium benzoate and potassium benzoate, and the adhesive comprises about 0.1 wt % of the preservative.

13. An ultraviolet curable adhesive composition comprising components of formula

R-(L-X) n ,

wherein:

n is greater than or equal to 1;

R comprises at least one of cellulose, hemicellulose, lignin, and derivatives thereof and combinations thereof;

L is a linking component for covalently bonding X to R and comprises —O—C(O)O—(CH 2 CH 2 O) m —CH 2 CH 2 —, wherein m≧1; and

X comprises at least one of thymine, uracil, cytosine, and derivatives thereof and combinations thereof.

14. The adhesive of claim 13 , wherein the components of formula R-(L-X) n are

wherein:

m≧1; and

R 1 comprises trifluoromethyl, nitro, cyano, C 1 -C 20 alkyl, aryl, F, Cl, Br, I, C 1 -C 20 alkyl ether, C 1 -C 20 alkyl ester, benzyl halide, benzyl ether, aryl ether, hydroxyl, alkoxyl, amino, alkylamino, and dialkylamino.

15. The adhesive of claim 13 , wherein the components of formula R-(L-X) n are

wherein:

m≧1; and

R 1 comprises trifluoromethyl, nitro, cyano, C 1 -C 20 alkyl, aryl, F, Cl, Br, I, C 1 -C 20 alkyl ether, C 1 -C 20 alkyl ester, benzyl halide, benzyl ether, aryl ether, hydroxyl, alkoxyl, amino, alkylamino, and dialkylamino.

16. The adhesive of claim 13 , wherein the components of formula R-(L-X) n are

wherein:

m≧1; and

R 1 comprises trifluoromethyl, nitro, cyano, C 1 -C 20 alkyl, aryl, F, Cl, Br, I, C 1 -C 20 alkyl ether, C 1 -C 20 alkyl ester, benzyl halide, benzyl ether, aryl ether, hydroxyl, alkoxyl, amino, alkylamino, and dialkylamino.

17. The adhesive of claim 13 , wherein the components of formula R-(L-X) n are

Assignments (2)
RELEASE OF SECURITY INTEREST IN PATENTS, RECORDED ON JANUARY 29, 2019 AT REEL 048373 FRAME 0217 Recorded Sep 22, 2025
From: CRESTLINE DIRECT FINANCE, L.P., AS COLLATERAL AGENT
To: EMPIRE TECHNOLOGY DEVELOPMENT LLC
Reel/Frame 072936/0464 →
SECURITY INTEREST Recorded Jan 29, 2019
From: EMPIRE TECHNOLOGY DEVELOPMENT LLC
To: CRESTLINE DIRECT FINANCE, L.P.
Reel/Frame 048373/0217 →