Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1991-10-15
1992-10-13
Evans, Joseph E.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
549529, 549531, 549539, C07D30316, C07D30314, C07D30112, C07D30100
Patent
active
051552434
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a composition which comprises compounds having an epoxy group and a hydroxyl group and is industrially useful as a raw material or modifier for various resins for use in coating compositions, adhesives, epoxy resins, and the like, and also relates to a process for producing the composition.
BACKGROUND ART
Conventionally known as compounds having an epoxy group and hydroxyl group are glycidol and the like.
However, these compounds have poor storage stability because they are unstable in the presence of a slight amount of an acid or alkali, so that the epoxy group readily reacts with a hydroxyl group and a polymerization reaction thus proceeds, and further, side reactions are apt to take place when these compounds are subjected to various reactions.
On the other hand, as another compound having an epoxy group and hydroxyl group, the compound ##STR4## is known.
However, although stable as compared with the above-described glycidol and the like, this compound has been unsuited for use in various applications because the following intramolecular reaction takes place. ##STR5##
This may be because the compound becomes stable in entropy due to the formation of the 6-membered rings within the molecule.
Further, since the above compound (II) is poor in flexibility, it poses problems when used in applications such as, for example, coating compositions.
DISCLOSURE OF THE INVENTION
An object of the present invention is to provide a compound having an epoxy group and hydroxyl group and free from the above-described disadvantages.
The present inventor has conducted intensive studies in order to attain the above object and, as a result, it has been found that a compound having a specific structure is excellent in stability, ring-opening polymerization reactivity, and the property of imparting flexibility. Further, processes for efficiently producing such a compound have also been found. The present invention has thus been accomplished.
That is, the present invention is: ##STR6## (wherein x represents an integer of 3 to 7, y represents a statistical distribution of integers of 0 to 50, R.sub.a and R.sub.b represent H, methyl group, or propyl group, and each of the groups of R.sub.a and R.sub.b may be replaced with any of the other groups simultaneously)"; and following structural formula ##STR7## (wherein x represents an integer of 3 to 7, y represents an integer of 0 to 50, R.sub.a and R.sub.b represent H, methyl group, or propyl group, and each of the groups of R.sub.a and R.sub.b may be replaced with any of the other groups simultaneously), characterized in that a compound having the structure ##STR8## is reacted with a lactone at 30.degree. to 200.degree. C. in the presence of a catalyst"; and following structural formula ##STR9## (wherein x represents an integer of 3 to 7, y represents an integer of 0 to 50, R.sub.a and R.sub.b represent H, methyl group, or propyl group, and each of the groups of R.sub.a and R.sub.b may be replaced with any of the other groups simultaneously), characterized in that a composition comprising compounds having the following structure ##STR10## is epoxidized at 0.degree. to 80.degree. C. using a peroxide".
The composition of this invention which comprises epoxy compounds (I) having a hydroxyl group can be produced by either of the following two processes.
That is, these are a process in which compound (II) is reacted with a lactone in the presence of a catalyst (hereinafter referred to as Route A) ##STR11## and a process in which a composition comprising compounds (III) is reacted with an epoxidizing agent (hereinafter referred to as Route B). ##STR12##
In the process of Route A, compound (II) as a raw material can be obtained by epoxidizing 3-cyclohexene 1-methanol with an epoxidizing agent.
Examples of the above epoxidizing agent include organic percarboxylic acids such as performic acid, peracetic acid, perpropionic acid, perbenzoic acid, m-chloroperbenzoic acid, and the like, peracetic acid produced from hydrogen peroxide and acet
REFERENCES:
patent: 2786066 (1957-03-01), Frostack et al.
Fujiwa Takaaki
Isobe Tomohisa
Daicel Chemical Industries Ltd.
Evans Joseph E.
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