Zirconium-based and lanthanum-based ethylenically unsaturated metal salts
AssigneeArkema France
InventorGuillaume MONNIER
Life of this patent
Estimating the term…
Abstract
An ethylenically unsaturated and (co)polymerizable metal salt soluble in an ethylenically unsaturated reactive diluent is based on zirconium or on lanthanum and on an ethylenically unsaturated hemi-ester of a dicarboxylic acid. A process for the preparation of the salt and a crosslinkable composition comprising it are also disclosed. Uses of the metal salt include optical and dental uses, uses in composite materials, in moulding compositions, in 3D printing compositions and compositions for 3D articles and for coatings or adhesives. The finished crosslinked product which results from crosslinking the crosslinkable composition comprising the metal salt is also described.
Claims26
A (Co)polymerizable ethylenically unsaturated metal salt which is soluble in an ethylenically unsaturated reactive diluent, wherein the metal salt is a zirconium or zirconium oxide salt or a lanthanum salt with an ethylenically unsaturated hemi-ester of a dicarboxylic acid of formula (I):
- (X)n—R1—O2C—R—CO2 (I)
- and optionally, in addition to the said hemi-ester (I), in the presence of a saturated monocarboxylic acid of formula (II):
- R2CO2H, and that the said salt is defined according to one of the following formulae (Ill), (IV) or (V):
- [(X)nR1—O2C—R—CO2—]4-xZr(—O2CR2)x (III), with x=0 or 1 or 2 or 3,
- [(X)nR1—O2C—R—CO2—]2-xZr(=O)(—O2CR2)x (IV), with x=0 or 1, and
- [(X)nR1—O2C—R—CO2—]3-xLa(—O2CR2)x (V), with x=0 or 1 or 2,
- R being the residue, without the carboxyl groups, of a dicarboxylic acid of aliphatic, cycloaliphatic, aromatic or mixed structure,
- R1—(X)n being the residue, without OH, of an ethylenically unsaturated monoalcohol carrying n ethylenically unsaturated functional groups X chosen from (meth)acrylate (—CO2—C(R3)═CH2, with R3:
- —H or —CH3), vinyl (—CH2═CH2) or allyl (—CH2—CH2═CH2), with n being an integer ranging from 1 to 5 or from 1 to 3 or n being equal to 1, and
- R2 being the residue, without carboxylic group, of a saturated (without ethylenic unsaturation) monocarboxylic acid chosen from:
- a monoacid other than a dicarboxylic acid hemi-ester, the said monoacid being aliphatic, cycloaliphatic, heterocyclic, aromatic or mixed, or
- an acid hemi-ester of a dicarboxylic acid, of formula (VI):
- R′1—O2C—R′—CO2H,
- with, in this case, R2═R′1—O2C—R′—
- and
- R′1 being the residue of a saturated monoalcohol of aliphatic, cycloaliphatic, aromatic or mixed structure, and
- R′ being the residue of a dicarboxylic acid, without carboxyl groups, of saturated structure (without ethylenic unsaturation) of aliphatic, cycloaliphatic, aromatic or mixed structure, which can be identical to R when R is of saturated structure or which can be different from R,
- and optionally the said metal salt being in the form of a solution in an ethylenically unsaturated reactive diluent copolymerizable with the said salt.
(canceled)
Dependencies are inferred from the claim text.