Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From carboxylic acid or derivative thereof
Reexamination Certificate
1998-07-24
2001-02-13
Hampton-Hightower, P. (Department: 1714)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From carboxylic acid or derivative thereof
C528S332000, C528S363000, C528S373000, C525S410000, C525S418000, C525S419000, C524S252000, C424SDIG001
Reexamination Certificate
active
06187897
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a vinyl-group-containing dendrimer and a curable composition containing said dendrimer. More specifically, it relates to a curable composition containing a vinyl-group-containing dendrimer which can be used as a film-forming material such as a coating composition or an ink or as a raw material for a sealant, a molding material, an adhesive or a tackiness agent and which can be cured by heat or radiation to give a cured film. Further, the present invention relates to a curable composition which is a heat- or radiation-curable composition and can be applied to a vehicle for a printing ink or a coating composition or an adhesive.
PRIOR ART
Conventionally, resin solutions containing organic solvents are used as a coating composition, an adhesive, a tackiness agent, an ink, a filler and a molding material. The above resin solutions dissipate a large amount of the organic solvent in the steps of application, charging and curing. With increasing concerns about global and working environments, limitations have come to be imposed on the use of the above resin solutions. For this reason, there have been developed resin materials such as a water-soluble resin, a powder, a hot melt, and the like. A water-based resin composition requires a large amount of heat for evaporating water which is a dispersing agent, and further, since it often contains an organic solvent to some extent for improving its coatability, a waste liquid disposal remains to be solved. When used for coating or charging, a powder or a hot melt differ from conventional ones to a great extent in application and charging, and it is therefore newly required to introduce new equipment or facilities. For overcoming the above problems, the resin solution has been converted to a high solid or the water-based resin has been improved. Due to these efforts, it is considered that the use amount of the resin solutions tends to decrease further clearly. As a fundamental solution, however, it is strongly desired to develop a solventless liquid resin composition which is free of problems on environmental pollution, safety, hygiene, ignition, explosion, etc., and which can be widely applied and can be easily applied or charged.
Typical examples that can be referred to as a solventless liquid resin composition are radiation-curable resin compositions. Conventional radiation-curable resin compositions contain low-viscosity monomers such as various acrylic monomers, reactive oligomers such as urethane acrylate, epoxy acrylate or ester acrylate and optionally other resin component. The low-viscosity monomer is used mainly as a reactive diluent for controlling the viscosity of the composition. A composition containing a large amount of the low-viscosity monomer shrinks in volume when cured, and a cured film is fragile. Further, there is another problem that a residual monomer is odorous. It has been therefore desired to decrease the amount of the reactive diluent and increase the molecular weight thereof.
For improving a cured product in mechanical performance, it is preferred to incorporate a reactive oligomer, and it is further preferred to incorporate a resin material having a high molecular weight. Since, however, these materials have a high viscosity or are in a solid state, it is required to use a large amount of a reactive diluent in view of the fluidity of a composition before it is cured. The amount of the above materials is therefore limited. A cured product obtained by curing the conventional radiation curable resin composition is therefore poor in cured product properties such as hardness, toughness, mechanical properties and chemical resistance, and it is much inferior to a cured product obtained from a solvent-containing or water-based resin composition. For improving the film performance, there has been developed a radiation-curable resin composition containing a large amount of a reactive oligomer and a resin material having a large molecular weight. However, it contains a reactive diluent having a low molecular weight or an organic solvent for decreasing its viscosity to an applicable level, and under the circumstances, it cannot be said that it is improved in view of the environment.
Further, with developments in studies of polymers having hyper branched structures such as a comb-shaped polymer, a star-shaped polymer and dendrimers, studies of dendrimers terminated with a methacryl group are under way (Ref. Shi. W. et al., J. Appl. Polym. Sci. 59, 12, 1945 (1996)., Moszner N. et al., Macromol. chem. Phys., 197, 2, 621 (1996, JP-A-8-231864). However, known compounds are neither sufficient in curability as a radiation-curable material nor sufficient in adhesion to a substrate. Further, although it can be said that known compounds unquestionably have a low viscosity as compared with linear compounds having the same molecular weight, it cannot be said that the purpose in obtaining a low-viscosity resin composition by incorporating a large amount is fully achieved.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide a vinyl-group-containing dendrimer which can serve to decrease the amount of a low-molecular-weight compound having safety and performance problems and which can give a resin composition having a high molecular weight but a low viscosity and having excellent performance as a coating (film).
It is another object of the present invention to provide a polyfunctional, solventless and curable resin composition containing the above vinyl-group-containing dendrimer.
It is further another object of the present invention to provide a vinyl-group-containing dendrimer which can give a resin composition capable of forming a film (coating) by a conventional coating method using a roll coater or knife coater or by a conventional printing method such as an offset printing method, a gravure printing method, a letterpress printing method or a screen printing method, and a curable resin composition containing the above vinyl-group-containing dendrimer.
It is still further another object of the present invention to provide a curable resin composition containing a vinyl-group-containing dendrimer, which can be cured by any one of conventional triggers such as heating, ultraviolet light, infrared light, electron beam and &ggr; ray.
It is yet further another object of the present invention to provide a curable resin composition containing a vinyl-group-containing dendrimer, which is curable in the absence of a catalyst or a polymerization initiator when cured under irradiation with electron beams, &ggr; rays, and the like.
Further, it is another object of the present invention to provide a curable resin composition containing a vinyl-group-containing dendrimer, which is suitable for use in a vehicle for a printing ink or a coating composition or in an adhesive.
According to the present invention, there is provided a vinyl-group-containing dendrimer comprising a core portion, branching portions, branches and at least 4 terminal portions, and containing, as the terminal portions, at least one long-chain group selected from the class consisting of the groups of the following formulae (1-1), (1-2) and (1-3),
—C
n
H
2n
R
1
(1-1)
(C
x
H
2x
O)
m
R
2
(1-2)
—C
y
H
2y
O(COC
z
H
2z
O)
k
R
2
(1-3)
wherein R
1
is a phenyl group or a hydrogen atom, n is an integer of 4 to 25, x is an integer of 1 to 6, R
2
is a phenyl group or an alkyl group having 1 to 22 carbon atoms, y is an integer of 2 to 22, z is an integer of 2 to 15, m is an integer of 1 to 25 and k is an integer of 1 to 20, or at least one active-hydrogen-containing group selected from the class consisting of the following general formulae (2-1) to (2-5),
—NHR
3
(2-1)
wherein R
3
is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms,
—COOH (2-2)
—OH (2-3)
—Si(OR
4
)
3-h
(OH)
h
(2-4)
wherein R
4
is an alkyl group having 1 to 8 carbon atoms or a phenyl group and h is an integer of 1 to 3,
—P═O(OH)
2
(2-5)
Kawashima Miki
Nakamura Minoru
Tanaka Hiroaki
Hampton-Hightower P.
Toyo Ink Manufacturing Co. Ltd.
Wenderoth , Lind & Ponack, L.L.P.
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