Photo-curable compositions containing high refractive index monomers for use in 3D printing applications
AssigneeArkema France
InventorsYann Stolz, Noemi Feillee
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Abstract
Disclosed are high refractive index monomers for ceramic/metal 3D printing applications. The compositions disclosed herein have a higher refractive index and thus better resolution and lower scattering of the light when employed in a composition to deposit ceramic or metallic particles. The disclosed compositions also include low refractive cross-linkers selected for their good thermal decomposition and reactivity to provide good cohesion during the 3D printing.
Claims18
A photo-curable composition for use in a composition suitable for three-dimensional printing, the photo-curable composition comprising:
- a. a monomer composition comprising at least one monomer having a refractive index of at least 1.49, wherein the at least one monomer is selected from the group consisting of
- i. at least one monomer selected from the group consisting of poly(oxy-1,2-ethanediyl), alpha-(1-oxo-2-propen-1-yl)-omega-(4-(1-methyl-1-phenylethyl)phenoxy)-, N-vinyloxazole, and N-vinylcarbazole,
- ii. at least one monomer of Formula I
- wherein,
- Z is an ethylenically unsaturated group;
- X is O, S, or NH;
- L1 and L2 are each independently C1-C3 alkylene, —(C1-C3 alkylene)-S—(C1-C3 alkylene)-, or —(C1-C3 alkylene)-O—(C1-C3 alkylene)-;
- R is hydrogen or C1-C6 alkyl;
- R1 and R2 are each independently aryl, aryl (C1-C6 alkylene)-, heteroaryl, or heteroaryl (C1-C6 alkylene)-, each of which group is substituted with 0 to 5 substituents independently selected from halogen, C1-C4 alkyl, C1-C4 alkoxy, (C1-C4 alkyl)S—, C1-C4 haloalkyl, and C1-C4 haloalkoxy;
- and Y1 and Y2 are each independently O, S, NH, or N,
- iii. at least one monomer of Formula II
- wherein,
- A is H or CH3, and
- Q is selected from the group consisting of ethylene glycol phenyl ether, poly(ethylene glycol phenyl ether acrylate), phenyl, hexylphenoxy, hexylphenoxy, 2-phenylethyl, 4-methylphenyl, 4-methylbenzyl, 2-2-methyphenylethyl, 2-3-methylphenylethyl, 2-4-methylphenylethyl, 2-(4-propylphenyl) ethyl, 2-(4-(1-methylethyl)phenyl)ethyl, 2-(4-methoxyphenyl)ethyl, 2-(4-chlorophenyl) ethyl, 2-(2-chlorophenyl)ethyl, 2-(3-chlorophenyl)ethyl, 2-(4-chlorophenyl) ethyl, 2-(4-bromophenyl)ethyl, 2-(3-phenylphenyl)ethyl, 2-(4-phenylphenyl) ethyl), and 2-(4-benzylphenyl)ethyl or Q is a moiety that includes at least one substituted or unsubstituted heteroaromatic ring,
- iv. at least one monomer of formula III,
- wherein
- A is H or Me,
- L is a bond, C1-C3 alkylene or —(CRcRd—CR′cR′d—O)m;
- each Rc, Rd, R′c and R′d is independently H or alkyl;
- m is 2 to 10;
- and
- Q′ corresponds to one of the following formulae:
- wherein the symbol ● corresponds to the point of attachment to linker L;
- b. a cross-linker;
- and
- c. a plasticizer.
The photocurable composition according to 1, wherein the photocurable composition comprises
- from about 5 wt. % to about 40 wt. % based on the total weight of the photo-curable composition of monomer composition a);
- from about 20 wt. % to about 65 wt. % based on the total weight of the photo-curable composition of cross-linker b);
- and
- from about 20 wt. % to about 65 wt. % based on the total weight of the photo-curable composition of plasticizer c).
Dependencies are inferred from the claim text.