Resin containing phosphate group

Details Resin containing phosphate group Resin containing phosphate group

2002-12-26

2003-09-09

Pezzuto, Helen L. (Department: 1713)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Polymers from only ethylenic monomers or processes of...

C526S271000, C526S273000, C526S274000, C526S318440, C526S320000, C526S329200

Reexamination Certificate

active

06617409

ABSTRACT:

TECHNICAL FIELD
The present invention relates to a novel phosphate group-containing resin and a water based metallic coating material composition comprising the above phosphate group-containing resin.
BACKGROUND ART
A water based metallic coating material containing a metallic pigment such as aluminum flake has the problem that the metallic pigment is brought into contact with a large amount of water contained in the coating material and corroded to generate hydrogen gas. In order to solve this problem, it is proposed that phosphoric acid esters are added to a water based metallic coating material to protect the surface of a metallic pigment with the phosphoric acid esters making use of an adsorptive action exerted by an acidic hydroxyl group bonded to a phosphorus atom of the above esters to inhibit reaction caused by direct contact of water with the metallic pigment. However, it is difficult to inhibit this reaction over a long period of time in a water based metallic coating material comprising such phosphoric acid esters, and a metallic coating film formed has the defect that an adhesive property, a water resistance, a chipping resistance and a metallic finish feeling are not satisfactory.
Disclosed respectively are a water based metallic coating material comprising an aluminum flake treated with a phosphoric acid ester in Japanese Patent Application Laid-Open No. 168670/1983, a water based metallic coating material comprising a phosphoric acid ester of caprolactone in Japanese Patent Application Laid-Open No. 29607/1986, a water based metallic coating material comprising a reaction product of orthophosphoric acid and an epoxy compound in Japanese Patent Application Laid-Open No. 47771/1986, a water based metallic coating material comprising a phosphate-containing acryl polymer obtained from orthophosphoric acid and a glycidy group-containing acryl polymer in Japanese Patent Application Laid-Open No. 190765/1989 and a water based metallic coating material comprising a polymer of styrene and allyl alcohol and a reaction product of p-t-amylphenol and orthophosphoric acid or phosphorus pentaoxide in Japanese Patent Publication No. 46624/1990. However, all of these water based metallic coating materials have the defect that the coating films thereof are not satisfactory in an adhesive property, a water resistance and a metallic appearance.
DISCLOSURE OF THE INVENTION
It has been found that a phosphate group-containing resin which is a copolymer of two kinds of some specific phosphate group-containing polymerizable monomers and a polymerizable monomer having two tertiary alkyl groups in a molecule is excellent in an adsorptive property to the surface of a metallic pigment and effective for inhibiting a reaction of water with a metallic pigment over a long period of time and that a coating film formed from a water based metallic coating material comprising such phosphate group-containing resin is excellent in performances such as an adhesive property, a water resistance, a chipping resistance and a metallic finish feeling.
Thus, according to the present invention, provided is a phosphate group-containing resin obtained by copolymerizing:
(a) a polymerizable monomer having a phosphate group represented by a formula [—OPO(OR)(OH)] (wherein R represents a hydrocarbon group having 4 to 10 carbon atoms),
(b) a polymerizable monomer having a phosphoric acid group represented by a formula [—OPO(OH)
2
] and
(c) a (meth)acrylate base polymerizable monomer having two tertiary alkyl groups in a molecule, which is represented by:
wherein X represents hydrogen or methyl.
Further, according to the present invention, provided is a water based metallic coating material composition comprising the phosphate group-containing resin described above and a metallic pigment.
The phosphate group-containing resin and the water based metallic coating material composition which are provided by the present invention shall be explained below in further details.
EMBODIMENT OF THE INVENTION
Polymerizable Monomer (a) Having a Phosphoric Acid Monoester Group
The polymerizable monomer (a) is a phosphoric acid diester compound having each at least one phosphate group represented by a formula [—OPO(OR)(OH)] and polymerizable double bond in a molecule, wherein R represents a hydrocarbon group having 4 to 10 carbon atoms, and to be specific, it includes, for example, linear or branched chain alkyl groups such as butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, octyl, 2-ethylhexyl, decyl and isodecyl.
Included in the polymerizable monomer (a) are those obtained by reacting, for example, one acidic hydroxyl group contained in a phosphoric acid monoester represented by (HO)
2
PO(OR), for example, phosphate such as monobutyl phosphate (R═C
4
H
9
) and monoisodecyl phosphate (R═C
10
H
21
) with a glycidyl group-containing compound having a polymerizable double bond, for example, glycidyl acrylate and glycidyl methacrylate.
Polymerizable Monomer (b) Having a Phosphoric Acid Group
The polymerizable monomer (b) is a compound having each at least one a phosphoric acid group represented by a formula [—OPO(OH)
2
] and polymerizable double bond in a molecule, and to be specific, it includes, for example, (2-acryloyloxyethyl) acid phosphate, (2-methacryloyloxyethyl) acid phosphate, (2-acryloyloxypropyl) acid phosphate and (2-methacryloyloxypropyl) acid phosphate.
(Meth)acrylate Base Polymerizable Monomer (c)
The polymerizable monomer (c) is a compound represented by:
(wherein X represents hydrogen or methyl) in a molecule, and it has two tertiary alkyl groups in a molecule, in which three methyl groups are bonded to one carbon atom. Use of this monomer (c) makes it easy to allow metallic flakes to be aligned parallel to the coated face in the water based metallic coating material of the present invention and makes it possible to elevate the metallic appearance of the coating film.
Other Polymerizable Monomer (d)
The phosphate group-containing resin of the present invention is obtained by copolymerizing as essential components, the polymerizable monomer (a), the polymerizable monomer (b) and the polymerizable monomer (c) each described above, and if necessary, the other polymerizable monomer (d) in addition thereto can be used in combination as a copolymerization component.
The other polymerizable monomer (d) is a compound having at least one polymerizable double bond in a molecule other than the polymerizable monomers (a), (b) and (c) each described above, and it includes compounds exemplified below.
1) (Meth)acrylate base monomers: for example, C
1
to C
24
alkyl esters of (meth)acrylic acid such as methyl methacrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate and lauryl (meth)acrylate.
2) Hydroxyl group-containing monomers: for example, C
2
to C
10
hydroxyalkyl esters of (meth)acrylic acid, such as hydroxyethyl (meth)acrylate and hydroxypropyl (meth)acrylate.
3) Carboxyl group-containing monomers: for example, unsaturated carboxylic acids and anhydrides thereof such as (meth)acrylic acid, maleic acid and maleic anhydride.
4) Other monomers: for example, vinyl aromatic compounds such as styrene, &agr;-methylstyrene and vinyltoluene, (meth)acrylonitrile and vinyl acetate.
The phosphate group-containing resin of the present invention can be produced by copolymerizing the polymerizable monomers (a) to (d) each described above in the presence of a polymerization initiator by a conventionally known method, for example, a solution polymerization method. A use proportion of these polymerizable monomers in copolymerization shall not strictly be restricted and can be changed over a wide range depending on characteristics desired to the phosphate group-containing resin produced. In general, it can fall in the following range based on the total amount of the polymerizable monomers (a) to (d):
polymerizable
0.5 to 30% by weight, preferably 1 to
monomer (a):
20% by weight and particularly
preferably 1.5 to 15% by wei

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