IP Library Granted Patent US 10,407,574
Granted Patent B2
US 10,407,574 · App. 15/784,603 · Granted Sep 10, 2019

Composition with self-healing property, film with self-healing property and device including the film

Inventors: Mikhail Kovalev (Suwon-si, KR); Chung Kun Cho (Suwon-si, KR); Myung Man Kim (Suwon-si, KR); Nobuji Sakai (Kanagawa-ken, JP)
Assignee: SAMSUNG ELECTRONICS CO., LTD.
C09D4/00C08F230/08C08F290/067C08G18/12C08G18/3206C08G18/34C08G18/4277C08G18/4825C08G18/664C08G18/6659C08G18/6674C08G18/672C08G18/755C09D135/02C09D175/16C08F2230/085C08K5/549
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Quick Facts
Patent No.
US 10,407,574
App. No.
15/784,603
Granted
Sep 10, 2019
Kind
B2
Abstract

A self-healing composition including, urethane (meth)acrylate having two (meth)acrylate groups, six or more urethane groups, and a substituted or unsubstituted polyhedral silsesquioxane.

Claims (46)

1. A self-healing composition comprising,

a urethane (meth)acrylate having two (meth)acrylate groups, and six or more urethane groups, and

a substituted or unsubstituted polyhedral silsesquioxane;

wherein the urethane (meth)acrylate is a reaction product of a C1 to C20 aliphatic diisocyanate, a C1 to C100 aliphatic diol, and a C1 to C20 hydroxyalkyl(meth)acrylate;

wherein the C1 to C100 aliphatic diol comprises

about 50 weight percent to about 99 weight percent of a C10 to C100 polyalkylene glycol or a polylactone glycol, and

about 1 weight percent to about 50 weight percent of C1 to C9 alkylene glycol, based on a total weight of the C1-C100 aliphatic diol in the urethane (meth)acrylate.

2. The self-healing composition of claim 1 , wherein the urethane (meth)acrylate is represented by Chemical Formula 1:

wherein, in Chemical Formula 1,

n is a number ranging from 2 to 30,

R 1 is a hydrogen atom or a methyl group,

R 2 and R 3 are each independently a substituted or unsubstituted C1 to C20 alkylene group, or a substituted or unsubstituted C3 to C20 cycloalkylene group, and

R 4 is a substituted or unsubstituted C1 to C10 alkylene, a C2 to C100 divalent functional group including an ether group, an ester group, or a combination of the ether group and the ester group, or a combination thereof.

3. The self-healing composition of claim 2 , wherein the —O—R 4 —O— moiety of Chemical Formula 1 is represented by Chemical Formula 4-1 to Chemical Formula 4-4, or a combination thereof:

wherein, in Chemical Formula 4-1 to Chemical Formula 4-4, R 11 to R 18 are each independently a substituted or unsubstituted C1 to C10 alkylene group, and

wherein, in Chemical Formula 4-2 to Chemical Formula 4-4, a, b, x, and y are each independently a number ranging from 2 to 100.

4. The self-healing composition of claim 3 , wherein the —O—R 4 —O— moiety of Chemical Formula 1 is represented by Chemical Formula 4-11 to Chemical Formula 4-17, or a combination thereof:

wherein, in Chemical Formula 4-14 to Chemical Formula 4-17, a1, a2, a3, x1, and y1 are each independently a number ranging from 2 to 100.

5. The self-healing composition of claim 2 , wherein R 3 of Chemical Formula 1 is represented by Chemical Formula 3-1 to Chemical Formula 3-6, or a combination thereof:

6. The self-healing composition of claim 2 , wherein R 2 of Chemical Formula 1 is a substituted or unsubstituted C2 to C6 alkylene group.

7. The self-healing composition of claim 1 , wherein a weight average molecular weight of the urethane (meth)acrylate ranges from about 3,000 grams per mole to about 100,000 grams per mole.

8. The self-healing composition of claim 1 , wherein a glass transition temperature of the urethane (meth)acrylate ranges from about −40° C. to about 40° C.

9. The self-healing composition of claim 1 , wherein the polyhedral silsesquioxane is substituted with an alkyl group, an aryl group, a (meth)acryl group, a vinyl group, an amino group, an alcohol group, a carboxyl group, a halogen group, or a combination thereof.

10. The self-healing composition of claim 1 , wherein the polyhedral silsesquioxane is substituted with a phenyl group.

11. The self-healing composition of claim 1 , wherein the composition further includes a hardener, a solvent, or a combination thereof.

12. The self-healing composition of claim 11 , wherein the polyhedral silsesquioxane is present in an amount of about 0.1 weight percent to about 20 weight percent based on a total solid content of the self-healing composition.

13. The self-healing composition of claim 11 , wherein the hardener is present in an amount of about 0.01 wt % to about 5 weight percent based on a total solid content of the composition.

14. A self-healing film comprising, a cured product of a self-healing composition, the self-healing composition comprising:

a urethane (meth)acrylate having two (meth)acrylate groups and six or more urethane groups, and

a substituted or unsubstituted polyhedral silsesquioxane,

wherein the urethane (meth)acrylate is a reaction product of a C1 to C20 aliphatic diisocyanate, a C1 to C100 aliphatic diol, and a C1 to C20 hydroxyalkyl(meth)acrylate;

wherein the C1 to C100 aliphatic diol comprises

about 50 weight percent to about 99 weight percent of a C10 to C100 polyalkylene glycol or a polylactone glycol, and

about 1 weight percent to about 50 weight percent of C1 to C 9 alkylene glycol, based on a total weight of the C1-C100 aliphatic diol in the urethane (meth)acrylate.

15. The self-healing film of claim 14 , wherein a scratch in the self-healing film formed by a pencil having a hardness of 4H at a load of 1 kilogram-force is self-healed in 20 minutes.

16. The self-healing film of claim 14 , wherein light transmittance of the self-healing film is greater than or equal to about 90% and a yellowness index of the self-healing film is less than or equal to about 1.

17. A device comprising the self-healing film of claim 14 .

18. The device of claim 17 , wherein the device is a foldable display.

19. A self-healing composition comprising,

a urethane (meth)acrylate having two (meth)acrylate groups, and six or more urethane groups, and

a substituted or unsubstituted polyhedral silsesquioxane,

wherein the polyhedral silsesquioxane is substituted with an alkyl group, an aryl group, a (meth)acryl group, an amino group, an alcohol group, a carboxyl group, a halogen group, a phenyl group, or a combination thereof.

20. A device comprising a self-healing film, the self-healing film comprising a cured product of a self-healing composition, the self-healing composition comprising:

a urethane (meth)acrylate having two (meth)acrylate groups and six or more urethane groups, and

a substituted or unsubstituted polyhedral silsesquioxane,

wherein the device is a foldable display.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 16, 2019
From: KOVALEV, MIKHAIL; CHO, CHUNG KUN; KIM, MYUNG MAN; SAKAI, NOBUJI
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 048890/0521 →
Priority Claims (1)
KR 10-2016-0136690 · Oct 20, 2016 · national
Continuity (1)
Related Publication 20180112080A1 · Apr 26, 2018