Photochromic compositions and photochromic films

• US 8,323,535 B2
• Filed: 10/31/2008
• Issued: 12/04/2012
• Est. Priority Date: 11/01/2007
• Status: Active Grant

• Current Assignee: LG Chem Limited (LG Corporation)
• Original Assignee: LG Chem Limited (LG Corporation)
• Inventors: Choi, Hyeon, Kim, Jee-Seon, Kim, Woo-Sung, Hong, Young-Jun
• Primary Examiner(s): Ahvazi, Bijan
• Application Number:
  US12/740,965
• Publication Number:
  US 20100295003A1
• Time in Patent Office: 1,495 Days
• Field of Search: 522/100, 522/101, 522/13, 522/18, 522/102, 522/103, 522/153, 522/150, 522/167, 522/75, 522/181, 252/582, 252/586, 252/588, 252/589, 264/1.1, 264/1.27, 264/1.32, 264/1.36, 264/494, 264/496, 359/241, 359/242, 359/244, 359/265, 359/267, 359/275, 351/159, 351/160.R, 351/162, 351/163, 351/159.01, 523/106, 523/108, 523/135, 526/204, 428/137, 296/216.01, 296/84.1, 296/96.19, 296/97.1
• US Class Current: 252/586
• CPC Class Codes: C09D 133/14 of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
• CPC Class Codes: Y10T 428/24322 Composite web or sheet

Abstract

The present invention relates to a photochromic composition comprising multifunctional (meth)acrylate-based monomers having two or more functional groups, a photochromic dye and an aromatic vinyl compound, in which the content of the aromatic vinyl compound is more than 30% by weight and 70% by weight or less, a photochromic film produced by using the same, and a method for producing the photochromic film.

Claims

1. A photochromic composition comprising multifunctional (meth)acrylate-based monomers having two or more functional groups, a photochromic dye and an aromatic vinyl compound,

wherein the content of the aromatic vinyl compound is more than 30% by weight and 70% by weight or less, and the content of the multifunctional (meth)acrylate-based monomers having two or more function groups is more than 30% by weight,

wherein the multifunctional (meth)acrylate-based monomers having two or more functional group further comprises one or mixtures of two or more selected from the group consisting of dipentaerythritol hexaacrylate (DPHA), dipentaerythritol hydroxy pentaacrylate, pentaerythritol tetraacrylate, pentaerythritol triacrylate, trimethylene propyl triacrylate (TMPTA), propoxyate glycerol triacrylate and trimethylpropane ethoxy triacrylate;

and

wherein the photochromic composition further comprises a stabilizer, and the total content of the photochromic due and the stabilizer is 1.5% by weight to 5% by weight.

2. The photochromic composition according to claim 1, wherein the aromatic vinyl compound comprises at least one selected from styrene, styrene derivatives, divinylbenzene, and divinylbenzene derivatives.

3. The photochromic composition according to claim 1, wherein the aromatic vinyl compound comprises styrene or derivatives thereof in an amount of more than 30% by weight and 70% by weight or less.

4. The photochromic composition according to claim 1, wherein the multifunctional (meth)acrylate-haled monomer having two or more functional groups comprises one or mixtures of two or more selected from bisphenol A acrylate monomer and polyalkylene glycol di(meth)acrylate.

5. The photochromic composition according to claim 4, wherein the multifunctional (meth)acrylate-based monomer having two or more functional groups includes BP4PA (diaerylate of propylene oxide modified bisphenol A), EGDA (ethlyeneglycoldiacrylate) and EGDMA (ethyleneglycoldimethacrylate).

6. The photochromic composition according to claim 1, wherein the photochromic composition comprises long chain monomers having 15 or more C—

C bonds between the double bonds of the functional groups in an amount of 50% by weight or more, based on the total amount of the monomers, and short chain monomers having 15 or less C—

C;

bonds between the double bonds of the functional groups in an amount of less than 50% by weight, based on the total amount of the monomers.

7. The photochromic composition according to claim 1, wherein the photochromic dye is a spiro-oxazine or naphthopyran-based organic compound.

8. The photochromic composition according to claim 1, wherein the photochromic composition further comprises one or more additives selected from the group consisting of a polymerization initiator, a UV absorber, an antioxidant, a chain transfer agent, an IR absorber, an anti-foaming agent, an antistatic agent, and a release agent.

9. A photochromic film formed by curing the photochromic composition according to claim 1.

10. A transparent article, comprising a transparent substrate and the photochromic film according to claim 9 that is provided on at least one side of the transparent substrate.

11. The transparent article according to claim 10, comprising a structure of interposing the photochromic film between two transparent substrates.

12. The transparent article according to claim 11, comprising an adhesive layer that is interposed between the transparent substrate and the photochromic film.

13. The transparent article according to claim 10, wherein the transparent article is glasses for vehicles and buildings, high durability ski goggles, or functional signboard.

14. A method for producing a photochromic film comprising the steps of injecting the photochromic composition according to claim 1 into a space that is formed between a pair of substrates and a gasket

that is disposed between a pair of substrates, and curing it, wherein after the curing step, the gasket has a contraction ratio of 10% or more.

15. A method for producing a photochromic film comprising the steps of injecting the photochromic composition according to claim 1 into a space that is formed between a pair of substrates and a gasket that is disposed between a pair of substrates, and curing it, wherein after the curing step, the gasket has a contraction ratio being the same as or higher than that of the photochromic composition.