Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Compositions to be polymerized by wave energy wherein said...
Reexamination Certificate
2002-01-31
2004-03-16
Seidleck, James J. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Compositions to be polymerized by wave energy wherein said...
C522S086000, C522S087000, C522S088000, C522S089000, C522S090000, C522S097000, C522S096000, C527S301000, C527S312000, C527S313000, C527S314000, C435S174000, C435S182000, C424S484000, C424S486000, C424S488000, C424S489000, C424S490000, C424S493000, C424S497000, C424S499000
Reexamination Certificate
active
06706778
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to a process for the production of molded particles for microbial cell-immobilization.
2. Description of the Prior Arts
There have been known various methods to immobilize microorganisms, such as encapsulation method, physical adsorption method and covalent bond method. Lump-like or sheet-like immobilized matters which are produced by these methods are usually cut or crushed fine before they are applied to microbial reaction. In these cases, however, immobilized matters often adhere to one another at the face, which decreases the efficiency of microbial reaction. On this account, it has recently been proposed to immobilize microorganism cells in the form of molded particles so that they may have less contact area and therefore be readily flowable, and to thereby increase the efficiency of microbial reaction [e.g., Japanese Patent Publication No. Sho 62 (1987)-19837, Japanese Patent Application Laid-Open No. Hei 10 (1998)-2109691].
Conventional molded particles for microbial cell-immobilization which comprise photocurable resin or thermocurable resin as a main component have, however, had a problem that, owing to their poor adhesiveness to the cell of negatively-charged microorganisms such as genus Pseudomonas, genus Paracoccus and genus Nitrosomonas, these conventional molded particles give only insufficient biological activity. Hence, improvement in this problem has been desired.
It is the primary objective of this invention to provide molded particles for microbial cell-immobilization which have improved adhesiveness to microbial cells.
As a result of assiduous study in order to attain the above-mentioned objective, the inventors of this invention have now found out that the adhesiveness of microbial cells to particulate carrier can be markedly improved by using, as a constituent material for particulate carrier for immobilization, a novel hydrophilic urethane resin which is prepared by making tertiary amino group-containing diol react with polyisocyanate compound, and further by introducing two or more ethylenically unsaturated groups. Thus, the inventors have completed this invention.
SUMMARY OF THE INVENTION
According to one aspect of this invention, there is provided a process for the production of molded particles for microbial cell-immobilization which is characterized in that:
an aqueous liquid composition which comprises:
(a) an ethylenically unsaturated group-containing hydrophilic urethane resin which is obtained by making tertiary amino group-containing diol (i), which is selected from the group consisting of product (i-1) from a reaction between a diglycidyl compound and a secondary amine which is free of hydroxyl group and product (i-2) from a reaction between a monoglycidyl compound and a secondary amine which has hydroxyl group, react with polyisocyanate compound (ii) so that isocyanate group may exceed hydroxyl group in said diol (i), and further by making thus produced isocyanate group-containing urethane resin (iii) react with compound (v) which has both ethylenically unsaturated group and hydroxyl group;
(b) a polymerization initiator; and
(c) water-soluble macromolecular polysaccharides which are capable of gelation by contact with metal ion;
is gelatinized, in an aqueous medium which contains metal ion, to be particulate gel, which is then subjected to photopolymerization and/or thermopolymerization by which to cause the crosslinking reaction of ethylenically unsaturated group in said particulate gel.
According to another aspect of this invention, there is provided a process for the production of molded particles for microbial cell-immobilization which is characterized in that:
an aqueous liquid composition which comprises:
(a) an ethylenically unsaturated group-containing hydrophilic urethane resin which is obtained by making tertiary amino group-containing diol (i), which is selected from the group consisting of product (i-1) from a reaction between a diglycidyl compound and a secondary amine which is free of hydroxyl group and product (i-2) from a reaction between a monoglycidyl compound and a secondary amine which has hydroxyl group, react with polyisocyanate compound (ii) so that hydroxyl group in said diol (i) may exceed isocyanate group in said polyisocyanate compound (ii), and further by making thus produced hydroxyl group-containing urethane resin (iv) react with compound (vi) which has both ethylenically unsaturated group and isocyanate group;
(b) a polymerization initiator; and
(c) water-soluble macromolecular polysaccharides which are capable of gelation by contact with metal ion;
is gelatinized, in an aqueous medium which contains metal ion, to be particulate gel, which is then subjected to photopolymerization and/or thermopolymerization by which to cause the crosslinking reaction of ethylenically unsaturated group in said particulate gel.
In the following, the process of this invention for the production of molded particles for microbial cell-immobilization is explained in more detail.
DETAILED DESCRIPTION OF THE INVENTION
The molded particles of this invention are produced as follows: an aqueous liquid composition which comprises, as essentially components, (a) a hydrophilic urethane resin, (b) a polymerization initiator and (c) water-soluble macromolecular polysaccharides, is dripped or poured into an aqueous medium which contains metal ion, and is thus gelatinized to be particulate gel, which is then subjected to photopolymerization and/or thermopolymerization by which to cause the reaction and curing of ethylenically unsaturated group in said particulate gel.
Hydrophilic Urethane Resin (a)
The hydrophilic urethane resin which is component (a) in the above-mentioned aqueous liquid composition is an ethylenically unsaturated group-containing hydrophilic urethane resin which is obtained by making a tertiary amino group-containing diol (i), which is selected from the group consisting of product (i-1) from a reaction between a diglycidyl compound and a secondary amine which is free of hydroxyl group and product (i-2) from a reaction between a monoglycidyl compound and a secondary amine which has hydroxyl group, react with polyisocyanate compound (ii), and further by making thus produced isocyanate group-containing urethane resin (iii) or hydroxyl group-containing urethane resin (iv) react with compound (v) which has both ethylenically unsaturated group and hydroxyl group, or with compound (vi) which has both ethylenically unsaturated group and isocyanate group.
First, from a reaction, which is to be conducted by any known method, either between diglycidyl compound and a secondary amine which is free of hydroxyl group, or between monoglycidyl compound and a secondary amine which has hydroxyl group, there is obtained reaction product (i-1) or (i-2) each of which has a tertiary amino group and two hydroxyl groups in a molecule, i.e., tertiary amino group-containing diol (i).
Diglycidyl compound which is used for the production of reaction product (i-1) is a compound which has, in a molecule, two glycidyl groups as follows:
As examples of such a compound, there are mentioned diglycidyl ether compounds and alicyclic diglycidyl compounds. Examples of diglycidyl ether compounds include diglycidyl ether of bisphenols such as bisphenol A, bisphenol F and bisphenol S; and diglycidyl ether of alkylene glycols (preferably C
2
-C
9
alkylene glycols) or of polyalkylene glycols (preferably C
2
-C
3
polyalkylene glycols), such as neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, ethyleneglycol diglycidyl ether, diethyleneglycol diglycidyl ether, polyethyleneglycol diglycidyl ether, propyleneglycol diglycidyl ether, dipropyleneglycol diglycidyl ether and polypropyleneglycol diglycidyl ether. As products of these compounds on the market, there are mentioned EPOLEAD NT212, EPOLEAD NT214, EPOLEAD NT228 and EPOLEAD CDM manufactured by Daicel Chemical Industries, Ltd., and DENACOL EX-201, DENACOL EX-211, DENACOL EX-212, DENACOL EX-810, DENACOL EX-811, DENA
Miyagawa Kenji
Seko Kenji
Yoshitake Junya
Kansai Paint Co. Ltd.
McClendon Sanza L
Seidleck James J.
Wenderoth , Lind & Ponack, L.L.P.
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