US3838124A - Derivatives of isocyanuric acid and processes for preparing the same - Google Patents

Derivatives of isocyanuric acid and processes for preparing the same Download PDF

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Publication number
US3838124A
US3838124A US00343076A US34307673A US3838124A US 3838124 A US3838124 A US 3838124A US 00343076 A US00343076 A US 00343076A US 34307673 A US34307673 A US 34307673A US 3838124 A US3838124 A US 3838124A
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United States
Prior art keywords
acid
isocyanuric acid
reaction
derivatives
approximately
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US00343076A
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English (en)
Inventor
E Matzner
R Mitchell
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Monsanto Co
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Monsanto Co
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Priority to NL7200247A priority Critical patent/NL7200247A/xx
Priority to FR7200646A priority patent/FR2121711B1/fr
Priority to DE19722200984 priority patent/DE2200984B2/de
Priority to CA132,092A priority patent/CA953724A/en
Priority to LU64569D priority patent/LU64569A1/xx
Priority to GB100072A priority patent/GB1354637A/en
Priority to BE777882A priority patent/BE777882A/fr
Application filed by Monsanto Co filed Critical Monsanto Co
Priority to US00343076A priority patent/US3838124A/en
Application granted granted Critical
Publication of US3838124A publication Critical patent/US3838124A/en
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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
    • D06M13/288—Phosphonic or phosphonous acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F5/00—Softening water; Preventing scale; Adding scale preventatives or scale removers to water, e.g. adding sequestering agents
    • C02F5/08—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents
    • C02F5/10—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances
    • C02F5/14—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances containing phosphorus
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
    • C07F9/3817—Acids containing the structure (RX)2P(=X)-alk-N...P (X = O, S, Se)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
    • C07F9/6521—Six-membered rings

Definitions

  • the present invention relates to a new class of isocyanuric acid derivatives and processes for preparing such compounds. More particularly, the present invention has as its primary object providing phosphorus-containing isocyanuric acid derivatives and processes for preparing the same.
  • R is hydrogen, phenyl, substituted phenyl or C alkyl and R and R, can be the same or different and are selected from the group consisting of hydrogen, metal ions, ammonium ions, alkyl ammonium ions, alkyl, alkenyl, aryl and alkaryl radicals.
  • the aforementioned metal ions may be monovalent or polyvalent and include without limitation alkali metals such as sodium, lithium and potassium; alkaline earth metal such as calcium and magnesium; aluminum; zinc; cadmium; manganese; nickel; cobalt; cerium; lead; tin; iron; chromium; and mercury. Where the metal ions are monovalent each R and R may individually be such metal ion. Where the metal ions are divalent each divalent metal ion will replace a pair of R radicals which may be R R R R or R +R, and may be from the same or ditferent isocyanuric acid derivative molecules. Likewise a trivalent metal ion such as chromium will replace three R radicals in a similar manner.
  • alkyl ammonium ions are those derived from amines having molecular weights below about 300. Particularly preferred are alkyl amines, alkylene amines and alkanol amines containing from 2 to about 10 carbon atoms and not more than two amine groups, including for example ethyl amine, diethyl amine, triethyl amine,
  • Useful alkyl and alkenyl radicals are those containing from 1 to about 18 carbon atoms and include both aliphatic and alicyclic radicals.
  • Preferred aliphatic radicals are those containing from 1 to about 8 carbon atoms while preferred alicyclic radicals are those having a total of from about 4 to 10 atoms up to 2 of which may be nitrogen, sulfur, oxygen or phosphorus with the remainder being carbon.
  • Useful aryl and alkaryl radicals are those containing up to about 40 carbon atoms and include phenyl, naphthyl, anthryl and phenanthryl, and hydroxy, halogen or amino substituted derivatives thereof.
  • Preferred alkyl aryl radicals are those wherein the alkyl has from 1 to about 6 carbon atoms.
  • the isocyanuric acid derivatives are prepared by reacting together (a) a phosphorus-containing material which is orthophosphorous acid, a combination of PO1 and H 0, or a dialkyl phosphite ester,
  • the Z-arninoethyl isocyanuric acid is prepared by the reaction of cyanuric acid with ethylene imine according to the procedure of N. Milstein, Journal of Chemical Engineering Data, Volume 13, -No. 2, page 275, April 1968.
  • Aldehydes that can be used in the processes of this invention to prepare the isocyanuric acid derivatives include those of the formula:
  • R is hydrogen, phenyl, substituted phenyl, or C alkyl.
  • Substituted phenyls include chlorophenyl, nitrophenyl, and C alkylphenyl.
  • aldehydes useful in the practice of the present invention include formaldehyde and paraformaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, benzaldehyde, tolualdehyde, chlorobenzaldehyde, and nitrobenzaldehyde.
  • aldehydes can be used per se or mixed with alcohol and/ or water in order to facilitate easier handling of the reaction mass, temperature control and the prevention of foaming.
  • formaldehyde which is a trademark for a 27% (United States) or 40% (British) formaldehyde solution
  • the preferred phosphors containing compound is orthophosphorous acid which is commercially available. It is to be understood, however, that while H PO is generally preferred the individual ingredients PCl and H 0 which react to make orthophosphorous acid can be used separately in the manufacturing process.
  • the orthophosphorous acid can be utilized in the process of the present invention either as the acid per se or in the form of one of its salts such as its monoor diammonium salts or its monoor dialkaline metal salts.
  • Such orthophosphorous acid salts will generally be utilized in combination with an amount of a supplementary acid sufiicient to maintain the pH of the reaction mixture below about 4 and to convert the orthophosphorous acid salt into the more reactive acid form.
  • the supplementary acid may be any strong acid as for example hydrochloric, sulfuric, hydrobromic, phosphoric, or sulfonic acid.
  • the actual preparation of the isocyanuric acid derivatives of the instant invention may be by any of several conventional routes which are taught in the literature.
  • the aldehyde reactant is formaldehyde or paraformaldehyde
  • the preferred route is the Mannich-type reaction described in the J. Org. Chem. 31, 1603-1607 (1966), in an article by Moedritzer and Irani.
  • stoichiometric amounts of the amine and phosphorous acid and a catalytic amount of hydrochloric acid are heated to reflux temperaure and 100% excess of aqueous formaldehyde or paraformaldehyde solution is added dropwise over a period of one to two hours. After refluxing for an additional period of one to two hours the resulting aminomethyl phosphonic acid is isolated by standard procedures.
  • reaction temperature be above about 85 C. and most preferably at reflux temperature.
  • hydrochloric acid be employed as a source of chloride ion and to maintain the reaction pH below about 4 and preferably below about 2. The low pH is most favorable to the desired reaction and the chloride ion serves to inhibit the oxidation of phosphorous acid to phosphoric acid.
  • strong acids can, of course be used to control pH- and the chloride ion may be introduced in other forms such as, for example, NaCl, KCl or other inorganic salts.
  • reaction process is carried out with conventional readily available chemical processing equipment.
  • a conventional heated glass lined reaction vessel equipped with an agitator and a reflux condenser is quite adequate to carry out this reaction.
  • the aldehyde reactant is an aliphatic or aromatic aldehyde other than formaldehyde as defined in Formula II above
  • the isocyanurate derivatives are preferably prepared by a process comprising the following steps:
  • a mixture of one mole of an aldehyde and 1-1.5 moles of phosphorus trichloride are heated in a sealed tube at a temperaure of from about to 250 C. for three to six hours. Required temperatures depend upon the specific aldehyde being used and temperatures of from to 200 C. are often adequate.
  • the reaction product is cooled and vacuum distilled to remove hydrogen chloride and unreacted phosphorus trichloride.
  • the reaction product which is the dichloride of chloroalkyl phosphonic acid is easily hydrolyzed by the action of water into the free chloroalkyl phosphonic acid, according to Step (2) above.
  • the selected chloroalkyl phosphonic acid prepared in accordance with the above is reacted with 2-aminoethyl isocyanuric acid to form the isocyanuric acid derivatives of the instant invention according to the general reaction described in Step (3) above which omits showing the intermediate steps of converting the chloroalkylphosphonic acid to the sodium salt, and converting the reaction product to the acid form.
  • the method of this reaction is described in Helv. Chim. Acta. 32, 1175 (1944) in an article by Schwarzenbach et al. The method requires a long reaction time, often several days, relatively high temperatures in the order of 80 C. and relatively high pH of 10-11. Because of hydrolysis of the chlorine-carbon bond in the chloroalkyl phosphonic acid, yields of the desired aminoalkylene phosphonic acid are low and the desired product must be separated from the hydroxy alkyl phosphonic acid secondary reaction product.
  • the acid and salt forms of the isocyanuric acid derivatives falling within Formula I of the present invention have utility in the field of treating water or aqueous systems and function as both a sequestering agent and as a threshold agent.
  • the term threshold as utilized herein refers to the chemical and/ or physical phenomenon that less than stoichiometric quantities of the particular isocyanuric acid derivatives can effectively prevent the precipitation and/or alter the crystal forms of various salts of metallic ions such as calcium, iron, copper and cobalt.
  • the threshold treatment of water is that technique by means of which less than stoichiometric quantities of the treating agent are added to interfere with the growth of crystal nuclei and thereby prevent the deposition of insoluble deposits.
  • the acid and ester forms of the isocyanuric acid derivatives falling within Formula I also have utility in the field of flame retardancy for cellulosic materials and specifically function as flame retardants therefor.
  • EXAMPLE I In a 2-liter flask are charged approximately 1480 milli liters of N,N-dimethyl formamide (DMF) and 129 grams of cyanuric acid. While stirring the mixture, a charge of approximately 43 grams of aziridine (ethylene) dissolved in 150 milliliters of DMF is added dropwise over a period of about 45 minutes. The temperature of the reaction mixture rises from about 27 C. to about 29 C. A fine white precipitate is formed during the addition. The overall re action mixture is continuously stirred for a period of 12 hours and then filtered. The resultant wet cake 154 grams) is Washed with absolute ethanol and then dried to obtain 125 grams of product which is characterized as a fine white powder. The yield is approximately 72.7% of theory and the product is analyzed as Z-aminoethyl isocyanuric acid which has the formula:
  • EXAMPLE II Into a 2-liter flask equipped with a water condenser and dropping funnel are charged approximately 96 grams (0.82 moles) of 70% orthophosphorous acid and 84 grams (0.85 moles) of 37% hydrochloric acid. The resultant mixture in the 2-liter flask is then heated to boiling while adding approximately 28.5 grams (0.17 moles) of the 2-aminoethyl isocyanuric acid prepared as described in Example I above. This Z-aminoethyl isocyanuric acid is added over a period of approximately 30 minutes. Approximately 60 milliliters of water is then charged (after the 30 minute addition period) into said reaction flask in order to obtain a homogeneous, clear solution having a boiling point of approximately 108 C.
  • the reaction mixture which is a clear solution, is cooled to 25 C.
  • An aliquot 50 grams of about 295 grams) of the solution is poured with stirring into milliliters of methanol, and there results a white precipitate.
  • the precipitate cake is reslurried in methanol, filtered and washed in the filter with methanol. Upon drying, approximately 2.0 grams of white solids are obtained. Referring to the entire batch, this represents a yield of approximately 11.8 grams of material and 19.3% of theory, based on the 2-aminoethyl isocyanuric acid utilized.
  • the white solids are analyzed, utilizing the P Nuclear Magnetic Resonance spectra (NMR) (which shows the presence of N-C-P linkage) and elemental analysis.
  • NMR Nuclear Magnetic Resonance spectra
  • the resultant white solids are found to contain substantially isocyanuryl ethyl imino di(methylenephosphonic acid) having the following structural formula:
  • the above analyses show the white solid material to contain some impurities.
  • the reaction product is found to have utility as a sequestration agent as demonstrated in Example IV hereinafter set forth.
  • EXAMPLE III Into a 2-liter flask equipped with a water condenser and dropping funnel are charged approximately 113 grams (0.82 moles) of diethyl phosphite (C H O) PHO. The phosphite is then heated to about 100 C. while adding approximately 28.5 (0.17 moles) of the 2-aminoethy1 isocyanuric acid prepared as described in Example I above. This 2-aminoethyl isocyanuric acid is added over a period of approximately 10 minutes.
  • C H O diethyl phosphite
  • the resultant mixture in the flask is maintained at about l00110" *C., and 27 grams (0.90 moles) of paraformaldehyde is added over a period of about three hours. At the end of the addition period, the reaction mixture is cooled to 25 C. The batch weighs 168 grams and is characterized by being an oily liquid. The oily liquid is analyzed, utilizing the P Nuclear Magnetic Resonance spectra (NMR) and elemental analysis. The resultant material is substantially the ester as shown by the following structural formula:
  • the amount of calcium nitrate solution added to each flask is sufiicient to provide ample data to plot the point of inflection at which the sequestrant-containing solution goes from a relatively clear solution to a turbid one. This inflection point is indicative of the amount of calcium that is sequestered by the particular sequestration agent.
  • isocyanuric acid derivatives falling within Formula I are their use as a sequestration agent in treating aqueous systems containing calcium ions to prevent the formation of calcium salts and scale therein.
  • EXAMPLEV In order to demonstrate the utility of the esters of the isocyanuric acid derivatives falling within Formula I, approximately 50 grams of the ester prepared in Example -III above are mixed with an inert solvent (carbon tetrachloride) in a 500 milliliter beaker in order to prepare a 10% by weight solution of said ester. After the slurry is prepared, a separate and individual switch of a 3" x 3" undyed cotton cloth is intimately contacted with the slurry by submerging such swatch in the slurry for approximately five minutes. The swatch is withdrawn from the slurry and dried for minutes in an oven which is maintained at a temperature of approximately 80 C. After 15 minutes at 80 C., the temperature is elevated to approximately 150 C. for 10 minutes in order to promote a reaction between the ester and the surface groups on the cotton fibers.
  • an inert solvent carbon tetrachloride
  • the dried swatch of treated cotton cloth is tested for flame retardancy by positioning the swatch over a Bunsen burner.
  • the flame is adjusted to a point at which the tip of the flame is approximately one inch beneath the treated cotton swatch; an untreated cotton swatch is used as a control for comparative purposes.
  • the flame underneath each of the individual cotton swatches (including the control) is maintained for approximately 35 seconds, and then is removed.
  • Visual observations indicate that while the control sample ignites and burns completely, the treated sample is self-extinguishing and is primarily only charred by this test.
  • one application of the esters of the isocyanuric acid derivatives falling within Formula I is their use as a fire retardant for cellulose material, such as cotton cloth.
  • An isocyanuric acid derivative having the formula 0 R1 ll dHI 0R OR HN/ NCHzCHN 4 o o o if dn-r -om OH; H
  • R is hydrogen, phenyl, halo-, nitroor C alkyl-substituted phenyl or C alkyl and R and R are selected from the group consisting of hydrogen, metal ions, ammonium ions, alkyl ammonium ions, C alkyl radicals, C alkenyl radicals, and aryl radicals, said aryl radicals being selected from the group consisting of phenyl, naphthyl, anthryl, and phenanthryl, and C alkyl, hydroxy, haloand amino-substituted derivatives thereof.
  • R and R are alkali metal ions selected from the group consisting of sodium, lithium, and potassium.
  • R and R each comprise one-half of a divalent metal ion selected from the group consisting of calcium, magnesium, zinc, cadmium, iron and copper.
  • R and R are each selected from the group consisting of hydrogen, C alkyl and phenyl.
  • a compound having the formula 10 A compound which is a metal salt of an acid having the formula References Cited UNITED STATES PATENTS 3,654,169 4/1972 Matzner et a1 260248 JOHN M. FORD, Primary Examiner US. Cl. X.R.
  • Col. 2 line 65 "phosphors" should rad phosphorus Col. 5 line 35 (ethylene) shbuld read (ethy'leneimin) Col. 7, line 43, "Switch? should rgad swatch Signed and sealed "this 17m ay of jnec'embr 1974.

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  • Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US00343076A 1971-01-11 1973-03-20 Derivatives of isocyanuric acid and processes for preparing the same Expired - Lifetime US3838124A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
NL7200247A NL7200247A (fr) 1971-01-11 1972-01-07
DE19722200984 DE2200984B2 (de) 1971-01-11 1972-01-10 Isocyanurylphosphonsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung
CA132,092A CA953724A (en) 1971-01-11 1972-01-10 Derivatives of isocyanuric acid and processes for preparing the same
LU64569D LU64569A1 (fr) 1971-01-11 1972-01-10
FR7200646A FR2121711B1 (fr) 1971-01-11 1972-01-10
GB100072A GB1354637A (en) 1971-01-11 1972-01-10 Isocyanuric acid derivatives
BE777882A BE777882A (fr) 1971-01-11 1972-01-10 Derives d'acide isocyanurique, et procedes pour les preparer
US00343076A US3838124A (en) 1971-01-11 1973-03-20 Derivatives of isocyanuric acid and processes for preparing the same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US10570771A 1971-01-11 1971-01-11
US00343076A US3838124A (en) 1971-01-11 1973-03-20 Derivatives of isocyanuric acid and processes for preparing the same

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BE (1) BE777882A (fr)
CA (1) CA953724A (fr)
DE (1) DE2200984B2 (fr)
FR (1) FR2121711B1 (fr)
GB (1) GB1354637A (fr)
LU (1) LU64569A1 (fr)
NL (1) NL7200247A (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4085283A (en) * 1975-04-19 1978-04-18 Stamicarbon, B.V. Phosphonate-isocyanurates
US4486359A (en) * 1979-07-09 1984-12-04 Alkaloida Vegyeszeti Gyar Process for the preparation of N-phosphonomethyl-glycine
US4587335A (en) * 1981-06-17 1986-05-06 Vincenzo Iannella Process for preparing 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-[(N-(2-pyridinyl)carboxamide)]-1,1-dioxide, phosphoric ester
US10066083B2 (en) * 2016-12-06 2018-09-04 International Business Machines Corporation Flame-retardant polyallyl and polyalkenyl isocyanurate compounds

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2157322B (en) * 1984-03-29 1987-10-21 Diversey Limited Removal of iron oxide deposits

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4085283A (en) * 1975-04-19 1978-04-18 Stamicarbon, B.V. Phosphonate-isocyanurates
US4486359A (en) * 1979-07-09 1984-12-04 Alkaloida Vegyeszeti Gyar Process for the preparation of N-phosphonomethyl-glycine
US4587335A (en) * 1981-06-17 1986-05-06 Vincenzo Iannella Process for preparing 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-[(N-(2-pyridinyl)carboxamide)]-1,1-dioxide, phosphoric ester
US10066083B2 (en) * 2016-12-06 2018-09-04 International Business Machines Corporation Flame-retardant polyallyl and polyalkenyl isocyanurate compounds
US10738176B2 (en) * 2016-12-06 2020-08-11 International Business Machines Corporation Flame-retardant polyallyl and polyalkenyl isocyanurate compounds

Also Published As

Publication number Publication date
FR2121711A1 (fr) 1972-08-25
NL7200247A (fr) 1972-07-13
BE777882A (fr) 1972-07-10
DE2200984A1 (de) 1972-07-20
LU64569A1 (fr) 1972-08-23
FR2121711B1 (fr) 1977-07-15
CA953724A (en) 1974-08-27
GB1354637A (en) 1974-06-05
DE2200984B2 (de) 1977-09-29

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