JPS6264801A - Cellulose carbamate derivative - Google Patents

Abstract

NEW MATERIAL:A cellulose carbamate derivative comprising structural units of formula I, wherein 80-100% of R groups are those of formula II (wherein at least two of R1-5 are 1-3 C alkyl and the rest are H atoms) and the remaining 20-0% of them are H atoms (part of them may be other substituents). EXAMPLE:Cellulose tris (3,4-dimethylphenylcarbamate). USE:Extremely useful as a functional material such as a packing for optical resolution. PREPARATION:An alkyl-substituted phenyl isocyanate is reacted with microcrystalline cellulose in the presence of a catalyst such as a base, e.g., a tert, amine or a Lewis acid, e.g., a tin compound.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a novel polymer that is extremely useful as a functional material.

[Prior art and problems]

Cellulose triphenyl carbamate is already known to have excellent resolving ability as a liquid chromatography filler for optical resolution (Y, Okamoto).

M, Kawashima and K, Hatada;
J, A+n, Chem+Soc,.

issue, 5357 '84).

In the process of researching cellulose triphenyl carbamate derivatives, the present inventor discovered that alkyl-substituted phenyl carbamate derivatives are also easily obtainable and have excellent asymmetric discrimination ability as fillers for optical resolution.

[Means for solving problems]

That is, the present invention provides a cellulose-based cellulose-based product comprising a structural unit represented by the following general formula (in the formula, even if 80 to 100% of R is absent, two are C2 to C3 alkyl groups). This relates to carbamate derivatives.

In the cellulose-based carbamate bond, 80 to 100% of all hydroxyl groups contained in cellulose form carbamate bonds.

That is, in the above formula, 80 to 100% of R is the remaining 20
~0% is generally hydrogen, but some other substituents can also be used.

Also, at least two of R8-R6 are 01-C3
is an alkyl group, preferably a methyl group.

The remaining R8-R5 are hydrogen.

The degree of polymerization of the cellulose derivative of the present invention is 2 to 1.00.
0, preferably 10-500.

The method for synthesizing the alkyl-substituted phenyl carbamate derivative of cellulose according to the present invention can be applied directly to a reaction that produces a urethane from an isocyanate and an alcohol.

For example, cellulose tris(alkyl-substituted phenyl) carbamate is obtained by reacting an alkyl-substituted phenyl isocyanate with cellulose in the presence of a base such as a tertiary amine or a Lewis acid catalyst such as a tin compound.

Furthermore, incyanato groups can be easily synthesized by reacting phosgene with the amine groups of the corresponding aniline derivatives. 1 [Effects of the Invention] The cellulose derivative of the present invention is an extremely useful substance as a functional material, and is particularly useful as a filler for optical resolution.

([Examples] (1): The present invention will be described in detail below with reference to Examples, but the present invention is not limited to these Examples.

[Example 1] Synthesis of cellulose tris(3,4-dimethylphenylene::11')carbamate Microcrystalline cellulose (manufactured by Merck & Co., degree of polymerization i 110)
0) 1, Pyridi 750m1.3,4-Dime:
Tylphenyl isocyanate 6.5txt 100℃
After heating for 17 h at
Pour into Nord 500x/. The resulting precipitate was dried separately.

Yield 3.31g Yield 89% Element Analysis-5 = Example 2゜Synthesis of cellulose tris(3,5-dimethylphenyl) carbamate In the same manner as in Example 1, 1 g of microcrystalline cellulose and 3,5
3,5-dimethylphenylgarno(mate) was obtained from 6.5jIl of -dimethylphenyl isocyanate.

Yield 3.269 Yield rate: 88% Element analysis

Claims (1)

[Claims] A structural unit represented by the following general formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, 80 to 100% of R is ▲There are mathematical formulas, chemical formulas, tables, etc.▼, R_1～R
At least two of _5 are C_1 to C_3 alkyl groups)
A cellulose carbamate derivative comprising: