Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1988-10-13
1990-01-02
Killos, Paul J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
C07L 6952
Patent
active
048914401
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
The present invention relates to a process for producing unsaturated quaternary ammonium salts represented by General Formula II: ##STR3## (in which R.sub.1 represents a hydrogen atom or a methyl group; R.sub.2 and R.sub.3 each represents an alkyl group containing 1 to 4 carbon atoms; A represents an oxygen atom or an --NH-- group; B represents an alkylene group containing 1 to 4 carbon atoms; R.sub.4 represents an alkyl group containing 1 to 4 carbon atoms or a benzyl group; and X.sup.- represents a halogen anion) which comprises treating cationic vinyl monomers represented by General Formula I: ##STR4## (in which R.sub.1, R.sub.2, R.sub.3, A and B have the same me as defined above) with an alkyl halide or an aralkyl halide. More particularly, it relates to a process for producing unsaturated quaternary ammonium salts of very high quality which contain impurities in only small quantities.
Homopolymers or water-soluble copolymers of the unsaturated quaternary ammonium salts represented by general formula II are highly useful water soluble cationic polymers utilizable as an agent for improving the yield of various additives upon paper making; as an agent for improving filtration of water upon paper making; as an agent for recovering white water; as an agent for processing fibrous pulp; as an filtration aid for sludge; or as a polymeric flocculant.
PRIOR ART
In one known process for producing such unsaturated quaternary ammonium salts, unsaturated tertiary amines are converted into corresponding quaternary salts by being allowed to react with an alkyl halide or an aralkyl halide in an organic medium. It is however not preferable to produce the quaternary ammonium salts of General Formula II in an organic solvent system which exhibits a chain transfer effect. This is because polymerization of the quaternary ammonium salts or copolymerization thereof with other monomers is generally carried out in an aqueous medium since polymers of the salts are employed :n an aqueous solution. In view of the above, there have been proposed in recent years various processes for producing the unsaturated quaternary salts in an aqueous medium.
In connection with this, there have been presented two problems to be taken into consideration upon production of the quaternary salts from the unsaturated tertiary amines.
Firstly, the cationic monomers represented by General Formula I or II are monomers having an extremely high polymerizability. As is well known, various proposals have been made for the prevention of their polymerization during production or storage. For example, Japanese Patent Publication No. 10,340/84 discloses that the polymerization of the quaternary ammonium salts of dialkylaminoalkyl (meth)acrylates occurs when the amount of oxygen dissolved in the aqueous solution thereof is small and that the polymerization of the salts dissolved in an aqueous solvent can be prevented by incorporating 50 to 1,000 ppm (based on the quaternary salts) of polymerization inhibitors and 1.8 ppm or more (based on the aqueous solution) of oxygen into the aqueous solution.
Secondly, there is a serious disadvantage that, in cases where the unsaturated quaternary ammonium salts are produced in water, the corresponding tertiary amines are susceptible to hydrolysis (in particular, in the cases where the tertiary amines are aminoesters represented by General Formula I in which A is an oxygen atom), and hence (meth)acrylic acid tends to be formed as a by-product. The desired unsaturated quaternary ammonium salts are cationic monomers based on their structure, whereas (meth)acrylic acid formed by the hydrolysis is an anionic monomer. Accordingly, if the polymerization is carried out in the presence of both of the monomers, there is formed a water-soluble substance, i.e., so-called ion complex. Consequently, the resulting polymer could not fully exhibit its effect as a polymeric electrolyte. It is therefore necessary that the desired unsaturated quaternary ammonium salts do not contain such a hydrolyzed product. Becau
REFERENCES:
CA 82(16): 99986d.
CA 87(16):120502h.
CA 93(10): 984802.
CA 106(14):102702e.
Harada Kazuya
Mukouyama Hideaki
Nagamoto Akiyoshi
Nagatsu Yoshirou
Killos Paul J.
Kohjin Co., Ltd.
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