Block copolymer having (meth) acryloyl groups in side chains...

Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...

Reexamination Certificate

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C525S332900, C525S387000

Reexamination Certificate

active

06177524

ABSTRACT:

TECHNICAL FIELD
The present invention relates to block copolymers having (meth)acryloyl groups in side chains, and to compositions containing the same. More particularly, the present invention relates to block copolymers having (meth)acryloyl groups in side chains that enable provision of hardened film exhibiting excellent adhesion to a substrate, solvent resistance, and gloss, when the copolymers are irradiated with an active energy beam such as a UV beam or an electron beam, and to compositions containing the same.
BACKGROUND ART
Conventionally, active-energy-beam-hardened type resin compositions, which are hardened through irradiation with an active energy beam such as a UV beam or an electron beam, have been practically used in the field of printing inks;
the field of coatings for plastic products, metallic products, furniture, and other products; the field of electrical insulation, e.g., insulating varnishes, insulating sheets, laminated boards, printed substrates, resist inks, and semiconductor-sealing agents; and other fields including the fields of adhesives, sealants, sizing agents for paper making, and lining materials. The resin compositions are utilized in such a variety of fields because they have the following advantages: (1) solvent-free and low environmental pollution; (2) remarkably high hardening speed to provide enhanced productivity of corresponding products; (3) remarkably low change in volume before and after hardening due to hardening as 100% solid matter; and (4) wide range of on-going development for coatings for plastics, paper, and inorganic materials; adhesives; and sealants due to low thermal loss by substrate materials or no thermal influence to substrate materials.
For example, epoxy (meth)acrylate resins which are obtained through ring-opening reaction of acrylic acid or methacrylic acid with epoxy groups of an epoxy resin are widely used as energy-beam-hardened type coatings, inks, and adhesives having the above-described characteristics. However, these widely used epoxy (meth)acrylate resins have disadvantages such as high degree of hardness and brittleness or high degree of shrinkage during hardening. For example, in the case in which such a resin is used as a printing ink for paper, printed ink generates cracks when the printed paper is folded. Also, in the case in which the resin is used as a coating for metal sheets of iron, aluminum, etc., the resultant film may easily generate cracks due to brittleness when the coated metal sheets is subjected to bend-processing to result in an unsuccessful processing, or adhesion of the coating to the metal sheets of iron, aluminum, etc. may sometimes be poor.
To overcome the disadvantages of such active-energy-beam-hardened type epoxy (meth)acrylate resins and active-energy-beam-hardened type epoxy resins, an object of the present invention is to provide block copolymers for hardenable resin compositions which provide a coating film exhibiting appropriate flexibility and exhibiting excellent adhesion, water resistance, and heat resistance, and remarkably excellent solvent resistance and gloss, and to provide a variety of hardenable resin compositions containing the copolymers.
DISCLOSURE OF THE INVENTION
In view of the foregoing, the present inventors have conducted earnest studies in order to provide block copolymers and hardenable resin compositions containing the same which meet to the above objects, and have found that block copolymers having (meth)acryloyl groups in side chains and compositions containing the copolymers exhibit hardenability and appropriate flexibility and exhibit excellent adhesion, water resistance, and heat resistance, and that the compositions provide a coating film having remarkably excellent solvent resistance and gloss. The present invention was accomplished based on this finding.
To solve the above problems, in one aspect of the present invention, there is provided a block copolymer having (meth)acryloyl groups in side chains, which copolymer is a ring-opening addition product of (meth)acryloyl-group-containing carboxylic acid to epoxy groups of a block copolymer obtained through epoxidation of double bonds derived from a conjugated diene compound contained in a base block copolymer formed of a polymer block of an aromatic vinyl compound and that of a conjugated diene compound.
The present invention also provides a block copolymer having (meth)acryloyl groups in side chains according to the first aspect of the present invention, wherein the conjugated diene compound contained in the epoxidized block copolymer is butadiene and/or isoprene.
The present invention also provides a block copolymer having (meth)acryloyl groups in side chains according to the first aspect of the present invention, wherein the epoxidized block copolymer has conjugated-diene-derived double bonds that are partially hydrogenated.
The present invention also provides a block copolymer having (meth)acryloyl groups according to the side chains in the first aspect of the present invention, wherein the epoxidized block copolymer is obtained by adding a (meth)acryloyl-group-containing carboxylic acid in an amount of 0.9-2.0 equivalents per equivalent of epoxy groups.
The present invention also provides a block copolymer having (meth)acryloyl groups in side chains according the first aspect of the present invention, wherein the (meth)acryloyl-group-containing carboxylic acid is selected from the compound group consisting of methacrylic acid, acrylic acid, 2-acryloyloxyethyl hydrogen phthalate, 2-acryloyloxypropyl hydrogen phthalate, 2-acryloyloxypropylhexahydro hydrogen phthalate, 2-acryloyloxypropyltetrahydro hydrogen phthalate, &bgr;-methacryloyloxyethyl hydrogen succinate, &bgr;-acryloyloxyethyl hydrogen succinate, and compounds represented by the following formulas (1) and (2):
CH
2
═CR
1
COOR
2
—O—(—COR
3
O—)
n
COR
4
—(—COOH)
m
  (1)
CH
2
═CR
1
CO—(—OR
3
CO—)
n
OH  (2)
{wherein R
1
represents hydrogen or a methyl group; each of R
2
, R
3
, and R
4
represents a C
1-10
aliphatic hydrocarbon group; and each of m and n represents an integer between 1 and 10 inclusive}.
The present invention also provides a block copolymer having (meth)acryloyl groups in side chains according to the first aspect of the present invention, wherein the (meth)acryloyl-group-containing carboxylic acid is monocarboxylic acid.
The second through fifth aspects of the present invention provide an adhesive composition, a sealant composition, a coating composition, and a sizing composition, respectively, containing the block copolymer having (meth)acryloyl groups in side chains according to the first aspect of the present invention.
BEST MODE FOR CARRYING OUT THE INVENTION
The present invention will next be described in detail.
The block copolymer having (meth)acryloyl groups in side chains according to the present invention comprises a base block copolymer containing a polymer block A predominantly formed of an aromatic vinyl compound, and a polymer block B predominantly formed of a conjugated diene compound. The copolymerization ratio of the vinyl aromatic compound to the conjugated diene compound in the base block copolymer is preferably {fraction (5/95)}-{fraction (70/30)} as a weight ratio, with {fraction (10/90)}-{fraction (60/40)} being particularly preferred. The base block copolymer has a number average molecular weight of 5000-500000, preferably 10000-200000, and has a molecular weight distribution [the ratio of weight average molecular weight (Mw) to number average molecular weight (Mn); i.e., (Mw/Mn)] of 10 or less. The molecular structure of the base block copolymer may be linear, branched, radial, or an arbitrary combination thereof. Examples of the polymer include vinyl aromatic compound-conjugated diene copolymers having a structure such as A-B-A, A-B, B-A-B-A, (A-B-)
4
Si, or A-B-A-B-A. Moreover, the base block copolymer contains a conjugated diene compound of which unsaturated bonds may be partially hydrogenated.
Examples of the vinyl aromatic compounds which con

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