Radiation imagery chemistry: process – composition – or product th – Electric or magnetic imagery – e.g. – xerography,... – Post imaging process – finishing – or perfecting composition...
Reexamination Certificate
2002-04-29
2004-10-26
Acquah, Samuel A. (Department: 1711)
Radiation imagery chemistry: process, composition, or product th
Electric or magnetic imagery, e.g., xerography,...
Post imaging process, finishing, or perfecting composition...
C528S361000, C528S363000, C528S364000, C430S108200, C430S127000, C430S137170, C430S311000, C430S332000, C435S130000, C435S132000, C435S136000, C435S137000, C435S155000, C435S162000, C435S253300
Reexamination Certificate
active
06808854
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a polyhydroxyalkanoate (hereinafter simply “PHA”) containing a novel structural unit and a production process thereof. More specifically, the present invention is directed to a process for producing a novel PHA containing a 3-hydroxyalkanoic unit which has a substituted phenylsulfinyl group and/or a substituted phenylsulfonyl group as a substituent at the end of its side chain, in which microorganisms capable of producing a PHA are cultured to produce and accumulate in the cell the PHA containing the 3-hydroxyalkanoic unit having the corresponding substituted phenylsulfanyl group as a substituent, and a sulfide-type sulfur in the PHA is selectively oxidized and converted into a sulfinyl or sulfonyl group, producing the desired PHA which is biodegradable.
This invention further relates to a charge control agent; a toner binder and a toner for developing electrostatic latent images, used in recording processes which utilize electrophotography, electrostatic recording, magnetic recording or the like, an image-forming method making use of the toner, and an image-forming apparatus therefor. More particularly, it relates to a charge control agent, a toner binder and a toner for developing electrostatic latent images, used in electrophotographic, electrostatic-recording and electrostatic-printing apparatus such as copying machines, printers and facsimile machines, an image-forming method making use of the toner, and an image-forming apparatus therefor. Still more particularly, it relates to a negatively charging charge control agent having higher safety for the human body and environment, a toner binder and a toner for developing electrostatic latent images, making use of such a charge control agent, an image-forming method making use of the toner, and an image-forming apparatus therefor.
2. Related Background Art
It has hitherto been reported that many microorganisms produce poly-3-hydroxybutyric acid (PHB) or other PHAs and accumulate it in the cell (“Handbook of Biodegradable Plastics”, Biodegradable-Plastic Institute, K.K. N.T.S, pp.178-197, 1995). Like conventional plastics, these polymers can be utilized for the production of various products by melt processing or the like. Also, since they are biodegradable, they have an advantage of being completely broken down by microorganisms in the natural world, and by no means remain in natural environment to cause pollution unlike many conventional synthetic polymeric compounds. They also have superior adaptability to living bodies and are expected to be applicable as medical flexible members.
It is known that such PHAs produced by microorganisms may have various compositions and structures depending on types of microorganisms used for its production, the composition of culture medium, the conditions for culture and so forth. Researches on how to control such compositions and structures have hitherto chiefly been made from the viewpoint of the improvement in physical properties of PHAs.
(1) Biosyntheses of PHAs by the polymerization of a monomer unit having a relatively simple structure such as 3-hydroxybutyric acid (hereinafter simply “3HB”), include the following:
(a) Those which involve 3HB and 3-hydroxyvaleric acid (hereinafter “3HV”):
Japanese Patent Publications No. 6-15604, No. 7-14352, No. 8-19227, etc., and Japanese Patent Application Laid-Open No. 5-7492.
(b) Those which involve 3HB and 3-hydroxyhexanoic acid (hereinafter “3HHx”):
Japanese Patent Application Laid-Open No. 5-93049 and No. 7-265065.
(c) Those which involve 3HB and 4-hydroxybutyric acid (hereinafter “4HB”):
Japanese Patent Application Laid-Open No. 9-191893.
(d) Those which involve 3-hydroxyalkanoates having 6 to 12 carbon atoms:
Japanese Patent No. 2642937.
(e) Biosynthesis utilizing a single fatty acid as a carbon source. Products are substantially the same as those of (d); Appl. Environ. Microbiol., 58(2), 746, 1992.
All these are PHAs which are comprised of monomer units having an alkyl group in the side chain, i.e., “usual PHA”, and produced through &bgr;-oxidation of hydrocarbons or synthesis of fatty acids from saccharides by the aid of microorganisms.
(2) When, however, broader application of such PHAs produced by microorganisms, e.g., application as functional polymers is taken into account, a PHA in which a substituent other than an alkyl group has been introduced in the side chain, i.e., “unusual PHA” is expected to be very useful. Examples of such a substituent may include those containing aromatic rings (such as a phenyl group and a phenoxy group), and unsaturated hydrocarbons, an ester group, an allyl group, a cyano group, halogenated hydrocarbons and epoxides. Of these, researches are enthusiastically made especially on PHAs having aromatic rings.
(a) Those which contain a phenyl group or a partially substituted phenyl group:
Macromol. Chem. Phys., 191, 1957-1965 (1990) and Macromolecules, 24, 5256-5260 (1991) report that
Pseudomonas oleovorans
produces a PHA containing 3-hydroxy-5-phenylvaleric acid as a unit, using 5-phenylvaleric acid as a substrate.
Macromolecules, 29, 1762-1766 (1996) reports that
Pseudomonas oleovorans
produces a PHA containing 3-hydroxy-5-(4′-tolyl)valeric acid as a unit, using 5-(4′-tolyl)valeric acid as a substrate.
Macromolecules, 32, 2889-2895 (1999) reports that
Pseudomonas oleovorans
produces a PHA containing 3-hydroxy-5-(2′, 4′-dinitrophenyl)valeric acid and 3-hydroxy-5-(4′-nitrophenyl)valeric acid as units, using 5-(2′, 4′-dinitrophenyl)valeric acid as a substrate.
(b) Those which contain a phenoxyl group or a partially substituted phenoxyl group:
Macromol. Chem. Phys., 195, 1665-1672 (1994) reports that
Pseudomonas oleovorans
produces a PHA copolymer of 3-hydroxy-5-phenoxyvaleric acid with 3-hydroxy-9-phenoxynonanoic acid, using 11-phenoxyundecanoic acid as a substrate.
Japanese Patent No. 2989175 discloses inventions which are concerned with a homopolymer comprised of 3-hydroxy-5-(monofluorophenoxy)pentanoate (3H5(MFP)P) units or 3-hydroxy-5-(difluorophenoxy)pentanoate (3H5(DFP)P) units, and a copolymer containing at least the (3H5(MFP)P) unit or the (3H5(DFP)P) unit;
Pseudomonas putida
capable of synthesizing such polymers; and processes for producing the above polymers by the use of the genus
Pseudomonas
. It is reported that, as the effect, a polymer having a phenoxyl group substituted at the side-chain terminal with 1 or 2 fluorine atom(s) can be synthesized by assimilating a long-chain fatty acid having a substituent and that stereo-regularity (isotacticity) and water repellency can be imparted while having a high melting point and retaining good processability.
In addition to such fluorine-substituted products, cyano-group- or nitro-group-substituted products are also being researched.
Can. J. Microbiol., 41, 32-43 (1995) and Polymer International, 39, 205-213 (1996) report that a PHA containing 3-hydroxy-p-cyanophenoxyhexanoic acid or 3-hydroxy-p-nitrophenoxyhexanoic acid as a monomer unit is produced using octanoic acid and p-cyanophenoxyhexanoic acid or p-nitrophenoxyhexanoic acid as a substrate by the use of
Pseudomonas oleovorans
strain ATCC 29347 and
Pseudomonas putida
strain KT 2442.
These reports are useful in order to obtain polymers which, differently from commonly available PHAs having an alkyl group in the side chain, all have an aromatic ring in the side chain, and have physical properties arising therefrom.
(3) Without being confined merely to changes in physical properties, research in a new category is being conducted to produce a PHA having a suitable functional group in the side chain.
For example, Macromolecules, 31, 1480-1486 (1996) and Journal of Polymer Science: Part A: Polymer Chemistry, 36, 2381-2387 (1998) report that a PHA containing at the side-chain terminal a unit having a vinyl group is synthesized, then the product synthesized is epoxidized with an oxidizing agent, thereby a PHA containing a highly reactive epoxy group at the side-chai
Imamura Takeshi
Kenmoku Takashi
Sugawa Etsuko
Yano Tetsuya
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