Claims
- 1. A product formed by the condensation of a mixture of difunctional tertiary amines and a molar quantity of 1,4-dichloro-2-butene that is substantially equal to the molar sum of the mixture of difunctional tertiary amines, said mixture of difunctional tertiary amines being selected from the group consisting of (a) 1,4-bis-(dimethylamino)-2-butene and N,N,N',N'-tetramethyl ethylene diamine, and (b) 1,4-bis-(dimethylamino)-2-butene and 1,4-bis-(methyl dodecylamino)-2-butene, the components of each mixture being present in a molar proportion of between 10% and 90% of the mixture.
Parent Case Info
This is a division of co-pending application Ser. No. 511,759, filed Oct. 3, 1974, issued as U.S. Pat. No. 3,928,323, which is a continuation-in-part of application Ser. No. 425,931, filed Dec. 18, 1973 and now issued as U.S. Pat. No. 3,874,870, dated Apr. 1, 1975.
This invention relates to a new class of microbiocidal agents. More particularly, the products of this invention are co-polymerization products made by condensing a mixture of two or more difunctional tertiary amines and a molar quantity of 1,4-dichloro-2-butene that is equal to the molar sum of the difunctional tertiary amines in the mixture.
The difunctional tertiary amines used in making the products of this invention are of the type ##STR1## where Z consists of from one to three divalent aliphatic radicals of 2 to 10 carbon atoms which may contain 0 to 2 double bonds or 0 to 2 hydroxy substituents; wherein R' and R" are either the same or different and wherein they may be (a) primary or secondary alkyls having 1 to 20 carbon atoms, where the sum of the carbon atoms in R' and R" is no greater than 36, (b) hydroxy or dihydroxy derivatives of the aforesaid primary or secondary alkyls, (c) benzyl, (d) alkyl benzyl or (e) combined with N to form a heterocyclic group of either 5, 6 or 7 atoms.
One of the features of the co-polymers of the present invention is that the quaternary ammonium moieties are part of the long polymeric chain rather than being quaternary ammonium moieties on branches that are bonded to the polymeric chain.
Another feature of the present invention is that the co-polymer is a unique reaction product and not a mere mechanical mixture of separate polymers. Therefore, the co-polymers of this invention cannot be separated into constituent components, as would be the case if they were mere mechanical mixtures.
Another feature of the present invention is that the primary chemical units comprising the polymeric chain are not identically repetitive as they would be if the product were an ordinary polymer. On the contrary, the several primary chemical units of the co-polymer are randomly distributed in the polymeric chain.
All of the above-described characteristics of the present invention are attained by causing a homogeneous mixture or solution of two or more difunctional tertiary amines to react with a molar quantity of 1,4-dichloro-2-butene which is equal to the molar sum of all of the components in the homogeneous mixture or solution of difunctional tertiary amines.
In this manner, if a homogeneous mixture or solution of 1,4-bis-(dimethylamino)-2-butene having the structure (CH.sub.3).sub.2 -- N--CH.sub.2 --CH= CH CH-- CH.sub.2 -- N-- (CH.sub.3).sub.2 and N,N'-dimethyl piperazine having the structure ##STR2## is reacted with a molar quantity of 1,4-dichloro-2-butene having the structure Cl-- CH.sub.2 -- CH= CH-- CH.sub.2 -- Cl equal to the molar sum of the two difunctional tertiary amines, the two primary units which are part of the polymeric chain would be: ##STR3## The ratio of the number of each of these units in the polymeric chain is very close to the molar ratio of the two difunctional tertiary amines in the starting mixture or solution, but the sequential order in which these two units appear in the polymeric chain is completely random, and therefore not identically repetitive.
The co-polymeric products of this invention are very effective microbiocides for use in controlling the microbial growth in circulatory and standing waters. They can, therefore, be used for the antimicrobial treatment of industrial waters, cooling tower water, humidifer water, swimming pools, and the like, as well as for general usage.
The following examples are illustrative of the present invention.
US Referenced Citations (8)
Divisions (1)
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Number |
Date |
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511759 |
Oct 1974 |
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Continuation in Parts (1)
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Number |
Date |
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425931 |
Dec 1973 |
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Patent Grant
4026945
