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
1999-05-21
2001-04-03
Short, Patricia A. (Department: 1712)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
C525S330500, C525S424000, C525S437000, C525S440030, C525S420000, C525S453000, C525S457000, C525S523000, C525S528000, C427S385500, C427S386000, C427S388200, C427S389900, C427S391000, C427S393000, C427S393500, C008S445000, C008S465000, C008S466000, C528S068000, C528S069000, C528S085000, C564S252000
Reexamination Certificate
active
06211293
ABSTRACT:
BACKGROUND OF THE INVENTION
a) Field of the Invention This invention relates to a novel polycarbodiimide compound, a production process thereof, a resin composition, and a treatment method of an article.
b) Description of the Related Art
A variety of resinous treatments have conventionally been used for the resin finishing or color finishing of fibrous articles such as threads, yarns, strands, woven fabrics, nonwoven fabrics, and paper sheets. Further, diverse resin compositions have also been used to coat, resin-finish, surface-coat or print metal articles such as iron articles and aluminum articles, synthetic resin articles such as polyethylene, polypropylene polyvinyl chloride, ABS, polyester and nylon articles, plastic films such as polyethylene, polypropylene, polyvinyl chloride and polyester films, and wooden articles.
For example, a resin-base pigmented printing paste for a woven fabric contains a colorant, a polymeric binder and a crosslinking agent for the polymeric binder. Conventional usable examples of the polymeric binder include acrylate, vinyl and diene polymers containing reactive groups. They may be used in the form of aqueous emulsion polymerization mixtures. As such crosslinking agent, compounds containing one or more methylol, alkylmethylol, epoxy, isocyanate or cyclic ethylene-imine groups have been used to date. Similar polymeric binders and crosslinking agents have also been used in paints for metal articles, synthetic resin articles and wooden articles as well as gravure printing inks for plastic films.
In the fields of woven fabrics, paints, printing inks and the like, however, it is required, depending on the application, to effect crosslinking at a low temperature to room temperature without heating a resin at a high temperature upon crosslinking the same. It is also required from the hygienic standpoint that a resin composition for use in such fields be sufficiently non-toxic and safe.
To meet such requirements, carbodiimide compounds are attracting interests as crosslinking agents for polymeric binders. Recently, compounds with plural carbodiimido groups contained therein have been found to be useful as crosslinking agents for polymeric binders and also to have high levels of non-toxicity and safety. For example, it has been proposed to use as a crosslinking agent for a polymeric binder a linear carbodiimide compound available by reacting a carbodiimido-containing diisocyanate compound, which is in turn obtainable by condensation of plural molecules of a corresponding diisocyanate compound, with a monoisocyanate compound, a monohydric alcohol compound or a dihydric alcohol compound.
These carbodiimide compounds are highly valued in non-toxicity and safety over the conventional crosslinking agents and, when crosslinking is conducted at high temperatures, give satisfactory results. They are however accompanied by a drawback that, when crosslinking is conducted at low temperatures to room temperature, they cannot bring about satisfactory results in the dry/wet fastness to rubbing, the fastness to laundering, and the like especially when applied to woven fabrics of synthetic fibers. When used in paints, coating formulations, printing inks and the like, they cannot bring about satisfactory results either insofar as crosslinking is conducted at low temperatures to room temperature.
SUMMARY OF THE INVENTION
As is appreciated from the foregoing, there is an outstanding demand for a crosslinking agent which can achieve sufficient crosslinking of polymeric binders at low temperatures to room temperature in various applications while fully meeting non-toxicity and safety requirements.
It is therefore a primary object of the present invention to provide a crosslinking agent which has no problem in toxicity and safety and can sufficiently crosslink various polymeric binders at low temperatures to room temperature.
In one aspect of the present invention, there is thus provided a polyfunctional polycarbodiimide compound comprising at least four molecular chains containing a carbodiimido (—N═C═N—) group and bonded independently to a backbone.
The polyfunctional polycarbodiimide compound according to the present invention has no problem in toxicity and safety and is useful as a crosslinking agent for sufficiently crosslinking various polymeric binders at low temperatures to room temperature.
In another aspect of the present invention, there is also provided a process for the production of a polyfunctional carbodiimide compound, which comprises reacting (a) an isocyanate compound having at least one carbodiimido group and at least one isocyanate group with (b) a polyol, polyamine and/or aminoalcohol having at least four hydroxyl, primary amino and/or secondary amino groups in a molecule.
In a further aspect of the present invention, there is also provided a resin composition comprising a polymeric binder and a crosslinking agent, wherein the crosslinking agent is the above-described polyfunctional polycarbodiimide compound, and the polymeric binder has groups reactive with the crosslinking agent.
In a still further aspect of the present invention, there is also provided a method for the treatment of an article, which comprises applying the above-described resin composition to the article by a method selected from the group consisting of coating, textile printing, impregnation and printing, and then drying the resin composition.
DETAILED DESCRIPTION OF THE INVENTION AND PREFERRED EMBODIMENTS
The present invention will hereinafter be described in further detailed based on certain preferred embodiments.
The polyfunctional polycarbodiimide compound according to the present invention is compound in which four or more carbodiimido-containing molecular chains are independently bonded to a backbone chain. It can be obtained by reacting the isocyanate compound having one or more carbodiimido group and one or more isocyanate groups [(hereinafter called the “side chain component (a)”] with the polyol, polyamine and/or aminoalcohol having four or more hydroxyl, primary amino and/or secondary amino groups in a molecule [hereinafter called the “backbone component (b)”] and, if necessary, further reacting the monohydric alcohol or monoamine containing one hydroxyl group, primary amino group or secondary amino group in a molecule [hereinafter called the “terminal component (c)”].
Illustrative of the above-described polyfunctional polycarbodiimide compound are:
(1) Products which are each available by reacting an isocyanate compound (component a-1), which contains one or more carbodiimido groups and one isocyanate group, with the backbone component (b) at an equi-equivalent ratio, namely, at a ratio of 1:1 in equivalent.
(2) Products which are each available by reacting one of two isocyanate groups of an isocyanate group (component a-2), which contains one or more carbodiimido groups and the two isocyanate groups, with the backbone component (b) and then reacting the terminal component (c) with unreacted isocyanate groups, which are still remaining in the reaction product, at an equi-equivalent ratio, namely, at a ratio of 1:1 in equivalent.
(3) Products which are each available by reacting first the component (a-1) and then the component (a-2) with the backbone component (b) and further reacting the terminal component (c) with unreacted isocyanate groups, which are still remaining in the reaction product.
In each of the above-described reactions, a polyol, polyamine and/or aminoalcohol containing two or three hydroxyl, primary amino and/or secondary amino groups in a molecule may be added to the reaction system so that the molecular chain of the resultant compound is extended further.
The component (a-1) employed in the above-described reaction is available in a manner known per se in the art, namely, by reacting a di- or polyisocyanate compound, for example, in the presence of a carbodiimidation catalyst such as 3-methyl-1-phenyl-3-phosphorene-1-oxide to couple two isocyanate groups into a carbodiimide group while maintaining one of termina
Kawamura Tatsuo
Nakamura Michiei
Okura Ken
Shimanaka Hiroyuki
Sugawara Eiichi
Dainichiseika Color & Chemicals Mfg. Co. Ltd.
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
Short Patricia A.
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