Lowly lactone-modified reactive monomer composition, acrylic polyol resins produced with the same, curable resin compositions and coating compositions
AssigneeDaicel Chemical Industries, Ltd.
InventorAkira Okazaki
Life of this patent
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Abstract
This invention provides a hydroxyalkyl(meth)acrylate composition modified by a small amount of lactones in which a proportion of monomers having two or more continuous chains of lactone is less than 50% (area % by GPC). This invention also provides methods for synthesizing such a composition. This invention also provides an acrylic polyol resin comprising the hydroxyalkyl(meth)acrylate composition, a carboxylic group-containing acrylate composition modified by a small amount of lactones, and a polyester unsaturated monomer modified by a small amount of lactones. Uses of these materials in curable resins, coating compositions, and finishing agents are also provided.
Claims13
A curable resin composition comprising:
- (i) 0.5-80 parts by weight of an acrylic polyol resin (A) comprising
- a hydroxyalkyl(meth)acrylate composition having
- 0.3 to less than 1.0 mole of polymerized lactone monomer being polymerized by ring-opening with respect to 1 mole of hydroxyalkyl(meth)acrylate, wherein the content of the lactone monomer in the hydroxyalkyl(meth)acrylate composition is 0-10% by weight, and
- a proportion of monomers having two or more continuous chains (n≧2) of lactones less than 37.4% (area by GPC),
- the hydroxyalkyl(meth)acrylate composition being represented by formula (1) described below,
- where
- R, R1, R2, and R3 are independently a hydrogen or a methyl group,
- “j” is an integer of 2-6,
- xn pieces of R4 and R5 are independently a hydrogen or an alkyl group having a carbon number of 1-12,
- “n” is an integer greater than or equal to zero, and
- an average value of “n” in the composition is not less than 0.3 to less than 1.0, and
- (ii) 0.5 parts by weight of a melamine resin (B),
- wherein the total of (A) and (B) does not exceed 100 parts by weight.
A thermosetting resin composition which comprises:
- 2-50 parts of an acrylic polyol resin (VII-A) containing a the hydroxyalkyl(meth)acrylate composition comprising
- 0.3 to less than 1.0 mole of polymerized lactone monomer being polymerized by ring-opening with respect to 1 mole of hydroxyalkyl(meth)acrylate, wherein the content of the lactone monomer in the hydroxyalkyl(meth)acrylate composition is 0-10% by weight, and
- a proportion of monomers having two or more Continuous chains (n≧2) of lactones less than 37.4% (area by GPC),
- the hydroxyalkyl(meth)acrylate composition being represented by formula (1) described below,
- where
- R, R1, R2, and R3 are independently a hydrogen or a methyl group,
- “j” is an integer of 2-6,
- xn pieces of R4 and R5 are independently a hydrogen or an alkyl group having a carbon number of 1-12,
- “x” is 4-7,
- “n” is an integer greater than or equal to zero, and
- an average value of “n” in the hydroxyalkyl(meth)acrylate composition is not less than 0.3 to less than 1.0,
- and 30-80 parts of an acrylic copolymer (VII-B) having an alkoxylsilyl group, wherein the total of (VII-A) and (VII-B) is 100 parts by weight.
A method for the preparation of a carboxylic group-containing acrylate composition (a′) represented by a general formula (VIII-3) described below, said method comprising:
- reacting a hydroxyalkyl(meth)acrylate composition, said hydroxyalkyl(meth)acrylate composition comprising 0.3 to less than 1.0 mole of polymerized lactone monomer being polymerized by ring-opening with respect to 1 mole of hydroxyalkyl(meth)acrylate, wherein the content of the lactone monomer in the composition is 0-10% by weight, and
- a proportion of monomers having two or more continuous chains (n≧2) of lactones less than 37.4% (area by GPC),
- the composition being represented by formula (1) described below,
- where
- R, R1, R2, and R3 are independently a hydrogen or a methyl group,
- “j” is an integer of 2-6,
- xn nieces of R4 and R5 are independently a hydrogen or an alkyl group having a carbon number of 1-12,
- x is 4-7,
- “n” is an integer greater than or equal to zero, and
- an average value of “n” in the composition is not less than 0.3 to less than 1.0, with a carboxylic acid or anhydride thereof (VIII-b) represented by a general formula (VIII-2) described below,
- (in the formula, R, R1, R2, and R3 are independently a hydrogen or a methyl group, j is an integer of 2-6, xn pieces of R4 and R5 are independently a hydrogen or an alkyl group having a carbon number of 1-12, “x” is 4-7, “n” is an integer greater than or equal to zero, an average value of “n” in said composition is not less than 0.3 to less than 1.0, R9 is a residual group of a carboxylic acid, and “m” is an integer of 1-3).
A method for the preparation of a polyester unsaturated monomer composition, comprising a small amount of lactones, wherein 0.3-less than 1.0 mole of a lactone monomer is polymerized by ring-opening with respect to 1 mole of a radically polymerizable unsaturated monomer containing carboxylic group, whereby, a proportion of monomers having not less than 2 continuous chains (n≧2) of lactones is adjusted to less than 50% (GPC area).
A method for the preparation of a polyester unsaturated monomer composition comprising:
- polymerizing, by ring-opening, 0.3 - less than 1.0 mole of a lactone monomer with respect to 1 mole of a radically polymerizable unsaturated monomer containing carboxylic group by using stannous halide, monobutylin tris-2-ethylhexanate, stannous octoate, dibutylin dilaurate, or a mixture thereof as a catalyst, and
- separating the unreacted radically polymerizable unsaturated monomer containing carboxylic group.
Dependencies are inferred from the claim text.