Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1998-09-10
2000-08-08
O'Sullivan, Peter
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
564396, 564398, 564399, 564431, 564434, 564443, 564446, 564461, C07C20926, C07C21136, C07C21140
Patent
active
061004308
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to an alicyclic polyamine which is useful as, for example, the diamine component of thermoplastic and thermosetting polymers and to a process for producing-the same.
BACKGROUND TECHNOLOGY
With the expanding application of polyurethane, polyamide, polyimide, and epoxy resin in recent years, there exists a demand for improvements in various polymer properties including weather resistance, water resistance, heat resistance, resistance to chemicals, electrical characteristics, and mechanical characteristics. In order to improve those polymer properties, several compounds, which are rather complicated in molecular structure, have been proposed for use as the diamine component of polymers. Among them are isophoronediamine, 4,4'-diamino-3,3'-diethyldiphenylmethane, diaminodiphenyl ether, 1,4-diaminobutane, and tolylenediamine, and so forth.
However, because of their complicated molecular structures, those diamines cannot be easily synthesized with high efficiency and at low cost on a commercial scale. Moreover, because the toxic prussic acid is generally used as an auxiliary starting material, their production on a commercial scale involves difficulties.
Meanwhile, as the curing agent for epoxy resin, there are known aliphatic polyamines such as diethylenetriamine, triethylenetetramine, diethylaminopropylamine, etc.; alicyclic polyamines such as isophoronediamine,etc.; and aromatic polyamines such as xylenediamine, diaminodiphenylsulfone,etc.; and so forth.
However, with those polyamines, all the above-mentioned polymer properties can hardly be implemented in a well-assorted balance.
It is, therefore, an object of the present invention to provide a polyamine useful as the diamine component of polymers and a process for producing the polyamine.
It is another object to provide a technology for providing the polyamine efficiently and a low cost.
DISCLOSURE OF INVENTION
Having explored into the art for accomplishing the above objects, the inventors of the present invention found that alicyclic polyamines having a certain defined structure are useful as the diamine component of various polymers and have perfected the present invention.
Thus, an alicyclic polyamine of the present invention is a compound of the following general formula(1). ##STR2## wherein Y.sub.1 represents a saturated aliphatic hydrocarbon group; R.sup.1 through R.sup.4 may be the same or different and each represents hydrogen, an alkyl group, a cycloalkyl group, an aryl group, or an aralkyl group. This aliphatic polyamine can be produced by reductive amination of a 3-formylcycloalkanone or 3-formylcycloalkenone.
As used in this specification, the term "alicyclic polyamine" means an alicyclic compound containing two or more similar or dissimilar primary, secondary, and/or tertiary amino groups.
BEST MODE FOR CARRYING OUT THE INVENTION
Alicyclic Polyamine
Referring to any alicyclic polyamine of the above formula (1), the bivalent saturated aliphatic hydrocarbon group designated by Y.sub.1 may be straight-chain or branched, and, in the case of a branched-chain hydrocarbon group, the same carbon atom may be substituted by 1 or 2 alkyl groups. The aliphatic hydrocarbon group includes, for example, C.sub.1-10 alkylene groups such as methylene, ethylene, propylene, trimethylene, 2-methyltrimethylene, 2,2-dimethyltrimethylene, tetramethylene, 2-methyltetramethylene, 2,2-dimethyltetramethylene, pentamethylene, hexamethylene, and so forth. Preferred straight-chain and branched alkylene groups are C.sub.2-8 alkylene groups, with C.sub.2-6 alkylene groups being particularly preferred.
Those aliphatic hydrocarbon groups may each be substituted, in suitable positions, by various substituent groups, for example, amino, hydroxy, C.sub.1-4 alkoxy, carboxy, alkoxycarbonyl, alicyclic hydrocarbon groups (cycloalkyl, cycloalkenyl, cycloalkinyl, etc.), and/or aromatic hydrocarbon groups (aryl groups such as phenyl).
Referring, further, to the above formula (1), R.sup.1 through R.sup.4 are the same or different an
REFERENCES:
patent: 3352913 (1967-11-01), Schmitt et al.
patent: 4925974 (1990-05-01), Gras
Poth et al., Chem Abst. 103:23851, 1985.
Hahn et al., Chem Abst. 102:96206, 1985.
Matsuoka Kazuyuki
Yagihara Hiroshi
Yamamoto Ken-ichi
Daicel Chemical Industries Ltd.
O'Sullivan Peter
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