High refractive index, UV-curable monomers and coating compositions prepared therefrom
Disclosed herein are high refractive index monomers that are curable by ultraviolet light. These monomers may be a component of curable compositions useful in the preparation of optical articles. Also disclosed is a method of synthesizing the monomers.
1. A high refractive index monomer, comprising:
a compound according to formula (I)
wherein Z is an ethylenically unsaturated group;
X is O, S, or NH;
L 1 and L 2 are each independently C 1 -C 3 alkylene, —(C 1 -C 3 alkylene)-S—(C 1 -C 3 alkylene)-, or —(C 1 -C 3 alkylene)-O—(C 1 -C 3 alkylene)-;
R is hydrogen or C 1 -C 6 alkyl;
R 1 and R 2 are each independently N-containing heteroaryl, or N-containing heteroaryl(C 1 -C 6 alkylene)-, each of which group is substituted with 0 to 5 substituents independently chosen from halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, (C 1 -C 4 alkyl)S—, C 1 -C 4 haloalkyl, and C 1 -C 4 haloalkoxy; and
Y 1 and Y 2 are each independently O, S, NH.
2. The monomer of claim 1 , wherein Z is acryloyl, methacryloyl, vinyl, or allyl; X is O or S; and R is hydrogen.
3. The monomer of claim 1 , wherein L 1 and L 2 are each independently methylene; ethylene; —(C 1 alkylene)-S—(C 2 alkylene)-, or —(C 2 alkylene)-S—(C 1 alkylene)-; —(C 1 alkylene)-O—(C 2 alkylene)-, or —(C 2 alkylene)-O—(C 1 alkylene)-.
4. The monomer of claim 1 , wherein R 1 and R 2 are each independently benzo[d]thiazolyl, benzo[d]oxazolyl, benzofuranyl, benzothiophenyl, benzoxadiazolyl, imidazolyl, indolyl, isoxazolyl, oxazolyl, N-phenothiazinyl, pyrazinyl, pyrazolopyrimidinyl, pyrazolyl, pyridizinyl, pyridyl, pyrimidinyl, pyrrolyl, quinolinyl, tetrazolyl, thiazolyl, thienylpyrazolyl, or triazolyl.
5. The monomer of claim 4 , wherein Y 1 and Y 2 are S.
6. The monomer of claim 1 , wherein the compound is 1,3-bis(benzo[d]thiazol-2-ylthio)propan-2-yl acrylate; 1,3-di(10H-phenothiazin-10-yl)propan-2-yl acrylate.
7. A high refractive index monomer comprising:
a compound according to formula (VI)
wherein Z is an ethylenicaily unsaturated group; X is O, S, or NH;
L3 and L4 are each independently
—(C 1 -C 3 alkylene)-S—(C 1 -C 3 alkylene)-,
or
—(C 1 -C 3 alkylene)-O—(C 1 -C 3 alkylene)-;
R is hydrogen or C1-C6 alkyl;
R10 and R11 are each independently aryl, including phenyl or naphthyl, aryl (C1-C6 alkylene)-; heteroaryl, or heteroaryl (C1-C6 alkylene)-; each or which group is substituted with 0 to 5 substituents independently chosen from halogen, C1-C4 alkyl, C1-C4 alkoxy, (C1-C4 alkyl)-S—, C1-C4 haloalkyl, and C1-C4 haloalkoxy.
8. The monomer of claim 7 , wherein Z is acryloxy, methacryloxy, vinyl or allyl; X is O or S; and R is hydrogen.
9. The monomer of ciaim 7 , wherein L3 and L4 are each independently —(—C 1 alkylene)-S—(C 2 alkylene)-; —(C 2 alkylene)-S—(C 1 alkylene); —(C 1 alkylene)-O—(C 2 alkylene)-; or (C 2 alkylene)-O—(C 1 alkylene)-.
10. The monomer of claim 7 , wherein R 10 and R 11 are each independently phenyl, 3-bromophenyl, 4-bromophenyl, 2,4,6-tribromophenyl, naphthyl, benzo[d]thiazolyl, benzo[d]oxazolyl, benzofuranyl, benzothiophenyl, benzooxadiazolyl, dihydrobenzodioxynyl, furanyl, imidazolyl, indolyl, isoxazolyl, oxazolyl, N-phenothiazinyl, pyranyl, pyrazinyl, pyrazolopyrimidinyl, pyrazolyl, pyridizinyl, pyridyl, pyrimidinyl, pyrrolyl, quinolinyl, tetrazolyl, thiazolyl, thienylpyrazolyl, thiophenyl, or triazolyl.
11. The monomer of claim 7 , wherein the compound is 1,3-bis(2-phenylthio)ethylthio)propan-2-yl acrylate.