Chemistry: fertilizers – Processes and products – Forms or conditioning
Patent
1985-01-18
1986-07-15
Evans, J. E.
Chemistry: fertilizers
Processes and products
Forms or conditioning
2605025R, 2605025E, 514144, 558176, 558 87, C07F 938, C07F 940, A01N 3102
Patent
active
046004297
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel guanidated aminophosphonic acid compounds and to the use of these compounds as biocides. The invention further relates to a process for the preparation of the guanidated aminophosphonic acid compounds and to novel aminophosphonic acid compounds useful as intermediates in this process.
The novel compounds of the invention have the general formula ##STR2## wherein Z and Z', which may or may not be equal, are hydrogen, a lower alkyl group having 1 to 4 carbon atoms or an alkali metal, Y is hydrogen or an amidine group, m is 1 to 3, n is 4 to 16 and p is 1 to 3. The invention also covers acid addition salts.
The compounds of the above given formula can be classed as guanidated N-(aminoalkyl)aminoalkanephosphonic acid derivatives and in the formula the lower alkyl esters, half esters and also the alkali metal mono- or di- salts are included.
The compounds are characteristic in that they contain both a phosphonic acid type group, ##STR3## and at least one guanidino group, ##STR4## and in that they are based on alkylene amines.
The pure compounds of the free phosphonic acids are fine white crystalline solids, and they are all soluble in water. The solubility in water decreases somewhat with increasing chain lengths. The esters are less soluble in water but soluble in alcohols and other solvents. As a rule the acid addition salts of the guanidated aminophosphonic acid compounds are much more soluble in water than the free acids and also more soluble in alcohols.
Preferred compounds are those containing alkylene groups having from 4 to 14 carbon atoms, and especially from 6 to 14 carbon atoms. Further, compounds of the general formula I given above wherein p equals 1 are preferred, i.e. the compounds based on alkylene diamines. Compounds wherein m is 1 are preferred to those wherein m equals b 2 or 3.
It should be understood that when p is 2 or 3, n does not necessarily have to be the same for the different alkylene groups. These might of course vary as a result of the use of technical amines having varying chain lengths as starting material. It should further be understood that when p is 2 or 3, either one, two or three of the Y-groups may be amidine groups, ##STR5## the rest being hydrogen. This depends on the guanidation reagent used in the preparation process and will be described more in detail below. However, compounds wherein all groups Y are hydrogen are preferred.
The invention also relates to a method for the preparation of guanidated N-(aminoalkyl)aminoalkanephosphonic acid derivatives of the above given formula (I), said method comprising reacting a halogenoalkanephosphonic acid compound with an alkylene di- or polyamine and guanidation of the so obtained product.
The first step of the preparation method comprises reacting a halogenoalkanephosphonic acid compound having the formula ##STR6## wherein Z and Z', as above, independent of each other are hydrogen, a lower alkyl group having 1 to 4 carbon atoms or an alkali metal, and m is 1 to 3, preferably 1, and wherein X is a halogen, suitably chlorine or bromine and most preferably chlorine, with an alkylene di- or polyamine of the formula. used as starting material.
The reaction between the halogenoalkanephosphonic acid compound and the amine is carried out in aqueous solution and at an elevated temperature. The temperature is suitably within the range of from 50.degree. to 100.degree. C. and preferably from 70.degree. to 100.degree. C. The reaction rate will of course vary with the temperature and also with the starting materials; usually a reaction time of up to about 20 hours will be sufficient. The reaction can be carried out under reflux. After the reaction is completed water and optionally excess of unreacted amine are removed, e.g. by distillation, and the product is isolated.
The aminoalkylaminophosphonic acid derivatives of the general formula ##STR7## are then guanidated using conventional guanidation reagents such as cyanamide, O-alkylisoureas, S-alkylisothioureas or salts of these etc. The temperature at
REFERENCES:
patent: 2599807 (1952-06-01), Bersworth
patent: 3322863 (1967-05-01), Rabourne et al.
patent: 3470112 (1969-09-01), Irani et al.
patent: 3769406 (1973-10-01), Anatol et al.
Oskes et al, "Chem Abstr.", vol. 78, No. 6 (1977) 30806 V (p. 41, col. 1).
Cameron David G.
Hudson Harry R.
Lagerlund Inger
Pianka Max
Stroomberg Anita
Evans J. E.
KenoGard AB
Philpitt Fred
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