Resin composition and process for producing the same

Details Resin composition and process for producing the same Resin composition and process for producing the same

2001-02-28

2002-02-05

Acquah, Samuel A. (Department: 1711)

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

Synthetic resins

At least one aryl ring which is part of a fused or bridged...

C528S206000, C528S219000, C524S714000, C524S718000, C524S780000, C524S781000, C524S785000, C524S798000

Reexamination Certificate

active

06344516

ABSTRACT:

TECHNICAL FIELD
The present invention relates to a resin composition and a method for producing the same, and in particular to a curable resin composition useful as a raw material for urushi(oriental lacquer)-like coating, a material for forming a coating film, a compound for recording material, a raw material for ink, a raw material for coating, a raw material for adhesive, a raw material for an epoxy resin, a raw material for photoresist, a raw material for antioxidant, a molding material, a raw material for laminated material, a raw material for adhesive, a raw material for binder, a raw material of a phenol resin for casting, a raw material of a phenol resin for rubber blending, and a raw material of a phenol resin for fiber plate; and a method for producing the same.
BACKGROUND ART
A wide variety of a phenol-compound-containing vegetable oil are known, among which urushiol, thitsiol, laccol, and cardanol, which are all obtained from sap of an Anacardiaceae plant, have been used as coatings (raw material for resin for dyes). Urushiol, thitsiol, or laccol forms a cured coating film at room temperature by an enzymatic catalyst (laccase) contained in the sap. The enzymatic catalyst is labile to heat, generally, when these resins are heated at 70° C. or more, the enzyme is inactivated, to reduce the catalytic activity, thus preventing the formation of a cured film, but the resins can be cured at about 130° C. or more. The cured coating film is not only excellent in hardness, with excellent in flexibility, but also in beauty, such as gloss, so it has been used for producing urushi ware since ancient times. Further, a urushi coating called kuro-urushi is made up of about 95% or more solids, the remaining being water, and thus the urushi coating can be regarded not only as a solvent-free type coating or a high-solid coating of a room temperature-curing type, but also as an organic coating film having high durability, as can be seen in lacquered remains artifacts as old as 1000 years or more. Further, the urushi coating can also be regarded as a coating with little affection on the natural environment, because, unlike synthetic resin coatings, the urushi coating neither uses a large amount of organic solvent nor requires high temperatures for curing. As described above, the urushi coating is an ideal coating at present, when the consciousness of global environmental problems is increasing. However, there are the problems that the urushi is produced only a small amount; it is expensive, and it is poison for the skin, etc.
On the other hand, a cashew nut shell liquid, obtained from the Anacardiaceae cashew tree (
Anacardium occidentale
), is produced in a large amount; it is inexpensive; it occurs as a by-product in preparation of edible kernel, and it is industrially useful as a urushi-like coating and a friction material (brake linings, brake pads), etc.
The cashew nut shell liquid contains a phenol compound such as anacardic acid which is a major component. The number of carbon atoms in the side chain of this compound is 15, and the number of an unsaturated bond in the side chain is 0 to 3 (average=about 2). Additionally, it is known that cardanol, cardol, 2-methyl cardol, and the like, are contained in the cashew nut shell liquid. The cashew nut shell liquid may be used as such for industrial purposes, but a material whose major component is cardanol, which is obtained by heat-treating the cashew nut shell liquid, to decarbonate a carboxyl group in anacardic acid, is generally used as a raw material for industry.
This cashew nut shell liquid (including the heat-treated material) is generally converted into cashew varnish for use in the various utilities described above, and, as can be seen from the extreme similarity in structure between cardanol and urushiol mentioned above, the cashew nut shell liquid has been used as a substitute for urushi. In the case of the cashew nut shell liquid unlike urushi, however, the curing reaction does not proceed by the enzymatic catalyst contained in the sap, and therefore, hexamethylenetetramine, which is a condensate of formaldehyde, and ammonia, or of formalin is reacted with the raw oil whose major component is cardanol, to produce cashew varnish (cardanol prepolymer). Then, a metal drier usually used in an oily coating is added thereto, as a catalyst, to oxidize the site of side-chain olefins, and other materials, such as predetermined pigments, etc., are mixed therewith, to give a general cashew resin coating as an oxidative-polymerizable coating. The cashew resin coating produced in this manner may cause the generation of formalin (formaldehyde), which is highly toxic to the human body, not only during the production process but also after a product is formed therefrom. However, the consciousness toward environmental problems has increased in recent years, and from the viewpoint of deodorization of the living environment and safety, health, etc., for the human body, there is a demand for a synthesis process that does not use highly toxic formalin (formaldehyde) in the cashew coating, as well as for development of a resin that does not generate formalin (formaldehyde).
Further, the phenol compound in the vegetable oil, such as the cashew nut shell liquid, generally have an unsaturated aliphatic group, such as an alkenyl group in the side chain, and in consideration of using the aforementioned phenol compound as an oxidative-polymerizable resin for a coating, which resin is curable at a room temperature, it is important that the reaction be suitably regulated so that the side chain in the phenol compound do not react during the polymerization reaction. However, when the polymerization reaction was carried out using a conventional catalyst without using formalin, hexamethylenetetramine, etc., it is difficult to regulate the reaction as only the site of the aromatic ring having a phenolic hydroxyl group undergoes oxidative polymerization. For example, JP-A-58-47079 describes a method for producing cashew dust by adding an acid to a cashew nut shell liquid, and then heat-polymerizing it, and then curing and grinding it, and in this process, a polymer called cashew dust, which is insoluble in solvent, is obtained, and it is not usable as a coating resin. Even if the product is not the dust but a polymer which is soluble in an organic solvent, the polymerization reaction proceeds in an alkenyl group in the side chain in the cashew nut shell liquid (shown in Comparative Example 2 below), and thus the reactivity of the remaining phenol site, which do not react yet, is utilized to prepare a cured product therefrom, but aldehydes, such as formalin, etc., are used often for linking the phenol site, so it is problematic that the toxicity of aldehyde cannot be solved.
On the other hand, it have already been known that phenols can be polymerized using an iron complex as the catalyst in the presence of oxygen (e.g., JP-A-49-26264). Further, it have already been known that phenols can be polymerized using a transition metal complex as the catalyst in the presence of peroxides (e.g., JP-A-8-53545 and Polymer Bulletin, 42, 125 (1999)). In these processes, however, the reaction materials are phenol compounds themselves, and these prior art documents do not show any example in which a phenol-compound-containing vegetable oil are used as a monomer component. Further, these prior art examples do not describe about a production of a curable resin composition derived from a vegetable oil by oxidative polymerization of only phenolic hydroxyl group, in a vegetable oil of nature origin containing multiple phenol compounds having an unsaturated aliphatic group such as an alkenyl group in the side chain.
Further, in Japanese Patent No. 3030363, the present inventors revealed a liquid resin formed by polymerizing a cashew nut shell liquid by use of an enzymatic catalyst, but the catalyst for obtaining the resin was not a transition metal complex.
The present invention relates to a resin composition and a method for producing the same, and it provides a curable

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