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
2002-03-27
2004-07-06
Lipman, Bernard (Department: 1713)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
C524S114000, C525S327200, C549S030000
Reexamination Certificate
active
06759484
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a method for inhibiting emission of odors from a composition containing a nucleophilic reagent and a polymer or compound having a five-membered ring dithiocarbonate(1,3-oxothiolane-2-thione) group, or a cured article obtained by curing the composition, which is useful in coating compositions, adhesives, inks, building sealants, semiconductor sealers, liners for civil engineering, optical materials, etc.; and a method for improving performances of the cured article.
This application is based on a patent application (Japanese Patent Application No. Hei 11-277733) filed in Japan, the content of which is incorporated herein by reference.
BACKGROUND ART
A polymer or compound having a five-membered ring dithiocarbonate group in a molecule is useful for various purposes. It is known that the polymer or compound is useful in coating compositions, adhesives, inks, building sealants, semiconductor sealers, liners used in civil engineering, optical materials, etc.
However, a composition itself containing a polymer or compound having a five-membered ring dithiocarbonate group and a nucleophilic reagent, and a cured article obtained by curing the composition have a problem in that an odor is emitted when it is heated to 60 to 80° C.
Japanese Patent Application Unexamined Publication No. Hei 9-59324 and WO98-45373 disclose compositions comprising a copolymer or compound having a five-membered ring dithiocarbonate group and a nucleophilic reagent. Both publciations also disclose optional addition of an epoxy resin to the composition comprising a copolymer or compound having a five-membered ring dithiocarbonate group and a nucleophilic reagent, and glycidyl(meth)acrylate as a monomer copolymerizable with a vinyl monomer having a five-membered ring dithiocarbonate group used in the preparation of a copolymer having a five-membered ring dithiocarbonate group, but do not describe an effect of inhibiting emission of odors.
Furthermore, Japanese Patent Application Unexamined Publication No. Hei 9-59324 discloses, in the examples, a vinyl-modified epoxy resin of a copolymer having a five-membered ring dithiocarbonate group. However, the publication does not describe an effect capable of inhibiting emission of odrs by modification with an epoxy resin.
Also, Japanese Patent Application Unexamined Publication No. Hei 8-302010 discloses that polythiourethane obtained by reacting a bifunctional five-membered ring dithiocarbonate compound with 1,&ohgr;-alkanediamine having 2 to 12 carbon atoms is useful as a curing agent of the epoxy resin.
Objects of the present invention are to provide a method for inhibiting emission of odors from a composition containing a nucleophilic reagent and a polymer or compound having a five-membered ring dithiocarbonate group, a cured article obtained by curing the composition, which is useful in coating compositions, adhesives, inks, building sealants, semiconductors sealers, liners for civil engineering, optical materials, etc.; and a method for improving performances of the cured article.
DISCLOSURE OF THE INVENTION
The method for inhibiting odors of the present invention is the method for inhibiting emission of odors comprising allowing a compound having an epoxy group to exist in a composition containing a nucleophilic reagent and at least a polymer or compound having a five-membered ring dithiocarbonate group represented by the following general formula (I), or in a cured article obtained by curing the composition,
wherein R
1
, R
2
and R
3
are the same or different and each represents a hydrogen atom or a lower alkyl group.
Further, by allowing the compound having an epoxy group to exist in the cured article, performances of the cured article can be improved. For example, in a cured article such as a coating film obtained by curing the composition, the hardness, strength, impact resistance, adhesion, water resistance, chemical resistance, weatherability, stain resistance, blocking resistance, or the like can be improved.
The present invention provides an inhibitor of emission of odors from a composition comprising a nucleophilic reagent and at least a polymer or compound having a five-membered ring dithiocarbonate group represented by the following general formula (I), or from a cured article obtained by curing the composition, and a performance improver for improving performances of the cured article. The inhibitor for emission of odors and the performance improver comprise a compound having an epoxy group.
The present invention provides a composition comprising a compound represented by the following general formula (III), a compound having an epoxy group, and a nucleophilic reagent,
wherein R
6
, R
8
, R
9
and R
11
are the same or different and each represents phenylene or cyclohexylene, 1 to 4 hydrogen atoms of which may be substituted with a halogen atom, R
7
and R
10
are the same or different and each represents methylene, C(CH
3
)
2
, an oxygen atom, CO, a sulfur atom or SO
2
, and m represents an integer of 0 to 40.
The present invention provides a compound having a five-membered ring dithiocarbonate group represented by the following general formula (IIIa).
BEST MODE FOR CARRYING OUT THE INVENTION
The present invention will now be described in detail.
In the definitions of the respective groups of the general formulas in the specification, the lower alkyl group includes, for example, a straight-chain or branched alkyl group having 1 to 6 carbon atoms, and is preferably an alkyl group having 1 to 4 carbon atoms.
Specific examples of the lower alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, an isopentyl group, a neopentyl group, and a hexyl group.
The polymer having a five-membered ring dithiocarbonate group represented by the general formula (I) includes, for example, a vinyl polymer, a polyester resin, an alkyd resin, a polyamide resin, polyether resin, a polyurethane resin, or a copolymer prepared by chemically bonding these resins, is preferably a copolymer, and is more preferably a vinyl copolymer. Specific examples thereof include a vinyl copolymer having a structural unit represented by the following general formula (II):
wherein R
1
, R
2
and R
3
are as defined above, R
4
and R
5
are the same or different and each represents a hydrogen atom or a lower alkyl group, and n represents an integer of 1 to 4.
In the definitions of the respective groups of the general formula (II), the lower alkyl group includes, for example, the same as those described above, and is preferably a methyl group or an ethyl group.
Examples of the other vinyl monomer, which is copolymerized with the monomer having a five-membered ring dithiocarbonate group as a raw material of the vinyl copolymer having a five-membered ring dithiocarbonate group, include known vinyl monomers, for example:
(meth)acrylic adid;
alkyl(meth)acrylates obtained from an alcohol having 1 to 18 carbon atoms and (meth)acrylic acid, such as methyl(meth)acrylate, ethyl(meth)acrylate, butyl(meth)acrylate, isobutyl(meth)acrylate, t-butyl(meth)acrylate, cyclohexyl(meth)acrylate, 2-ethylhexyl(meth)acrylate, lauryl(meth)acrylate, and stearyl(meth)acrylate;
aromatic vinyl compounds such as styrene, &agr;-methylstyrene, p-methylstyrene, dimethylstyrene, and divinylbenzene;
hydroxyalkyl(meth)acrylates such as 2-hydroxyethyl(meth)acrylate and 2-hydroxypropyl(meth)acrylate;
glycol di(meth)acrylates such as ethylene glycol di(meth)acrylate and butanediol di(meth)acrylate;
alkylaminoalkyl(meth)acrylates such as dimethylaminoethyl(meth)acrylate;
fluorine-containing vinyl monomers such as trifluoroethyl(meth)acrylate, pentafluoropropyl(meth)acrylate, perfluorocyclohexyl(meth)acrylate, 2,2,3,3-tetrafluoropropyl(meth)acrylate, and &bgr;-(perfluorooctyl)ethyl(meth)acrylate;
siloxane-containing vinyl monomers such as 1-[3-(meth)acryloxypropyl]-1,1,3,3,3-pentamethyldisiloxane, 3-(meth)acryloxypropyltris(trimethylsiloxane)silane, or AK-5
Gonno Akihiro
Hagino Harufumi
Kinoshita Nobuko
Murayama Toshikazu
Kyowa Yuka Co., Ltd.
Lipman Bernard
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