(Meth)acrylate compound, and copolymer and homopolymer comprising repeating unit derived from same

Patent metadata

Field	Value
Publication number	US-10214598-B2
Application number	US-201515508809-A
Country	US
Kind code	B2
Filing date	Sep 25, 2015
Priority date	Sep 30, 2014
Publication date	Feb 26, 2019
Grant date	Feb 26, 2019

Abstract

The present specification relates to a (meth)acrylate compound, and a copolymer and a homopolymer including a repeating unit derived therefrom.

First claim

The invention claimed is:

1. A (meth)acrylate compound represented by the following Chemical Formula 1:

in Chemical Formula 1,
at least one of R1 and R2 is hydrogen and a remainder is an alkyl group having 1 to 10 carbon atoms,
L1 is —N(H)C(═O)N(H)—; or —N(H)C(═O)-L4-C(═O)N(H)—,
L2 to L4 are the same as or different from each other, and are each independently an alkylene group having 1 to 10 carbon atoms unsubstituted or substituted by an alkyl group,
in the case where L2 and L3 are the same as or different from each other and are each independently an unsubstituted alkylene group having 1 to 10 carbon atoms, one of R1 and R2 is an alkyl group having 1 to 10 carbon atoms,
m and n are each 1 or 2,
when m is 2, two L2s are the same as or different from each other, and
when n is 2, two L3s are the same as or different from each other.

2. The (meth)acrylate compound of claim 1 , wherein Chemical Formula 1 is obtained by a reaction of an aziridine compound and a (meth)acrylic acid; or by a reaction of an aziridine compound and a hydroxyalkyl (meth)acrylate or a hydroxycycloalkyl (meth)acrylate.

3. The (meth)acrylate compound of claim 2 , wherein the aziridine compound is represented by the following Chemical Formula 2 or 3:

in Chemical Formulas 2 and 3,
R3 to R11 are the same as or different from each other, and are each independently hydrogen; or an alkyl group having 1 to 10 carbon atoms,
L12 and L14 are the same as or different from each other, and are each independently an alkylene group having 1 to 10 carbon atoms unsubstituted or substituted by an alkyl group,
m1 is 1 or 2, and
in the case where m1 is 2, two L12s are the same as or different from each other.

4. The (meth)acrylate compound of claim 2 , wherein the hydroxyalkyl (meth)acrylate or the hydroxycycloalkyl (meth)acrylate is represented by the following Chemical Formula 4:

in Chemical Formula 4,
R12 is hydrogen; or an alkyl group having 1 to 10 carbon atoms, and
R13 is an alkyl group having 1 to 10 carbon atoms substituted by at least one hydroxy group (—OH); or a cycloalkyl group having 3 to 10 carbon atoms substituted by at least one hydroxy group (—OH).

5. The (meth)acrylate compound of claim 1 , wherein Chemical Formula 1 is represented by the following Chemical Formula 1-1 or 1-2:

in Chemical Formulas 1-1 and 1-2,
L2 to L4 are the same as or different from each other, and are each independently an alkylene group having 1 to 10 carbon atoms unsubstituted or substituted by an alkyl group,
in the case where L2 and L3 are the same as or different from each other and are each independently an unsubstituted alkylene group having 1 to 10 carbon atoms, one of R1 and R2 is an alkyl group having 1 to 10 carbon atoms,
m and n are each 1 or 2,
when m is 2, two L2s are the same as or different from each other, and
when n is 2, two L3s are the same as or different from each other.

6. The (meth)acrylate compound of claim 1 , wherein the (meth)acrylate compound is represented by any one of the following Chemical Formulas 1-3 to 1-5:

7. A copolymer comprising:
a repeating unit derived from the (meth)acrylate compound according to claim 1 .

8. A homopolymer comprising:
a repeating unit derived from the (meth)acrylate compound according to claim 1 .

9. The homopolymer of claim 8 , wherein a glass transition temperature (Tg) of the homopolymer is 100° C. to 300° C.

10. The homopolymer of claim 8 , wherein a storage modulus of the homopolymer measured by a DMA (dynamic mechanical analysis) method at 25° C. is 3000 to 30000 MPa.

11. The homopolymer of claim 8 , wherein a gel fraction of the homopolymer is 85% to 100%.

12. The homopolymer of claim 8 , wherein, of an IR spectrum of the homopolymer, a peak of a region band of 1408 cm −1 which is a C═C band of a (meth)acrylate group of a repeating unit derived from the (meth)acrylate compound of the homopolymer is reduced as compared to a peak of an IR spectrum of the (meth)acrylate compound.

13. The homopolymer of claim 8 , wherein, of an IR spectrum of the homopolymer, an integral value of peak areas of a region band of 1408 cm −1 which is a C═C band of a (meth)acrylate group of a repeating unit derived from the (meth)acrylate compound of the homopolymer is reduced by 80% or more based on 100% of an integral value of peak areas of an IR spectrum of the (meth)acrylate compound.

Assignees

• Lg Chemical Ltd

Inventors

• Park Kwang Seung
• Lee Mi Rin
• Park Jun Wuk
• Huh Eunsoo
• Jeon Sung Hyun

Classifications

• C08F22/36

  Amides or imides · CPC title

• C07C275/04

  having nitrogen atoms of urea groups bound to acyclic carbon atoms · CPC title

• C07C219/08

  having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton · CPC title

• C08L33/04

  Homopolymers or copolymers of esters {(C08L43/04 takes precedence)} · CPC title

• C08F22/1006

  of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate · CPC title