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United States Patent Office Patented July 31, 1973

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United States Patent Office Patented July 31, 1973 3,749,672 United States Patent Office Patented July 31, 1973 2 are: melamine-formaldehyde resins, open-chain urea 3,749,672 formaldehyde resins and cyclic urea-formaldehyde resins. STABLIZED SOLUTIONS OF N-HALO COMPOUNDS After a number of washings, fabrics made from such William C. Goiton, Springfield, and Andrew F. Rutkiewic, synthetic polymers acquire a yellowish color and often West Chester, Pa., assignors to E. I. du Pont de 5 decompose when exposed to high temperatures. Non Nemours and Company, Wilmington, Del. synthetic fabrics, such as wool and silk are also yellowed No Drawing. Continuation-in-part of application Ser. No. when treated with strong hypochlorite bleaches. 6,540, Jan. 28, 1970, which is a continuation-in-part of In addition, hypochlorite bleaches exhibit a more rapid application Ser. No. 768,165, Oct. 16, 1968, which in decomposition upon storage and are, therefore, less turn is a continuation-in-part of application Ser. No. 0. stable than oxygen bleaches. In contrast, oxygen bleaches 729,461, May 15, 1968, all now abandoned. This ap do not have the high bleaching ability of hypochlorite plication Apr. 19, 1971, Ser. No. 135,373 bleaches, but their use in household laundry applications nt. C. Cld 7/54 results in less dye removal from the fabric and less fabric U.S. C. 252-95 12 Clains damage. 15 The deficiencies of the prior art bleaching compositions ABSTRACT OF THE DISCLOSURE make it desirable to produce a bleaching composition Described and claimed are stable aqueous systems con which has a bleaching ability approaching that of the taining an N-hydrogen compound and a hypobromite, strong hypochlorite bleaches but which is as safe for hypochlorite or hypoiodite in equilibrium with the corre dyes and fabrics as the oxygen bleaches. sponding N-halo compound or compounds. Stability is 20 Although bleaching compositions containing aqueous provided by inclusion of a buffer which maintains pH solutions of a hypochlorite, an N-hydrogen compound of the system between 4 and 11. The systems can be and the corresponding N-chloro compound or com used wherever gradual release of active halogen is de pounds, are known in the prior art, such compositions sired, e.g. as household laundry or industrial bleaches are designed for immediate use as a bleach because of or as agents for control of micro-organisms in process 25 their inherent instability and rapid loss of bleaching Water streams. activity. Solid N-chloro compounds, for example, are sold and used as bleaching compositions and are designed for such immediate use because of their relative in CROSS-REFERENCE TO RELATED stability in solution APPLICATIONS 30 N-chloro compounds have also been used heretofore to control the growth of micro-organisms in process water This application is a continuation-in-part of Ser. No. streams. U.S. Pat. 3,328,294, issued June 27, 1967, de 6,540, filed Jan. 28, 1970, now abandoned, which is a scribes the use of N-monochlorosulfamic acid and N,N- continuation-in-part of Ser. No. 768,165, filed Oct. 16, dichlorosulfamic acid and their alkali and alkaline earth 1968, now abandoned, which is in turn a continuation metal salts for this purpose, especially in papermaking. in-part of Ser. No. 729,461, filed May 15, 1968, and When placed in the process stream at very low concen now abandoned In the first two applications, the stabi tration, the N-chlorosulfamic acid slowly releases hypo lized solutions of this inveniton were described with chlorite. However, as described in column 5, lines 21 to 31 reference to their use as household laundry bleaches. of the patent, in concentrated solution the N-chlorosul In this continuing application and the application im 40 famic acid decomposes relatively rapidly. The N-chloro mediately preceding there are described other uses for sulfamic acid must, therefore, be used within a short time the solutions, especially the use in controlling micro after it is prepared. It is not suitable for preparation organisms. and subsequent storage without great loss of active chlo rine. This loss prevents long transportation and storage BACKGROUND OF THE INVENTION 45 which are necessary for a commercial product. Bleaching agents are divided into two basic classes: SUMMARY OF THE INVENTION oxidizing bleaches and reducing bleaches. Reducing According to this invention, there are provided aqueous bleaches, such as bisulfite-containing compositions, are systems which contain an N-hydrogen compound and a primarily used in the textile industry. On the other hand, 50 hypobromite, hypochlorite or hypoiodite, in equilibrium oxidizing bleaches, which contain compounds such as with the corresponding N-halo compound or compounds, chlorine, low oxyacids of chlorine, N-chloro compounds the N-halo compounds being present in a concentration and compounds containing a peroxy linkage, are com of 1 x 108 to 1.0 molar. The systems have improved monly used as household laundry bleaches and in paper stability due to control of the stoichiometry and inclu pulp bleaching. The most widely used oxidizing bleaches 55 sion of a buffer, the mole ratio of buffer to N-halo com for household laundry applications are the hypochlorite pound being at least 1:10, which maintains the pH in a and oxygen bleaches. Hypochlorite bleaches normally stable range between 4 and 11. The invention also pro contain 5 to 6 percent by weight aqueous solutions vides a method of making the above aqueous systems, of Sodium hypochlorite. Oxygen bleaches, sometimes in which the N-halo compounds are N-bromo or N called the safe bleaches, contain persulfate or perborate 60 chloro compounds, which comprises mixing the N-hydro compounds such as potassium mono-persulfate and sodi gen compound with a hypobromite or hypochlorite in um perborate. Although hypochlorite bleaches have a the presence of water and a buffer which maintains the better bleaching capability than oxygen bleaches, the use pH in a stable range between 4 and 11. The systems con of hypochlorite bleaches often results in fabric damage taining hypoiodite and N-iodo compounds in equilibrium and excessive dye removal. It is known, for example, 65 with N-hydrogen compounds are made by reacting the that strong hypochlorite bleaches have a harmful effect elemental iodine with the N-hydrogen compound in water on textiles and textile-treating resins made from synthetic in presence of an alkali and a buffer. polymers which contain a significant portion of NH The invention can be best explained by referring to a groups in the resin molecule. Examples of such polymers Specific embodiment, e.g. an aqueous solution of N,N-di 3,749,672 3 4. chlorosulfamate. The equilibrium equations for this sys above equilibrium equations for the hypochlorite-sulfa tem are as follows: mate system, free hypochlorite increases with increasing hydroxyl ion concentration. For this reason, the preferred HNSO---OC-seCIHNSOa --OH solutions are those which are buffered to a pH in the CHNSO---OClseClNSOa --OH range of 7 to 11. The equilibrium of this system favors the formation of 5 When used as a bleaching composition the N,N-di N,N-dichlorosulfamate ion, so the concentration of free chlorosulfamate solutions provide a unique balance be hypochlorite, i.e. hypochlorite present in Solution at tween a bleaching ability which approaches that of strong equilibrium conditions, is maintained at a low level. How: hypochlorite bleaches, and fabric and dye safety which ever, as the free hypochlorite is depleted during use of 0. approximates the safety of oxygen bleaches. In addition, the solution, more hypochlorite is produced, owing to the the solutions exhibit improved stability as compared to tendency of the system to return to equilibrium. Thus, the sodium hypochlorite solutions. solution can be used where it is desired to have a con trolled availability of hypochlorite ion, e.g. as a household DESCRIPTION OF THE PREFERRED laundry bleach or as an additive to process water streams 5 EMBODEMENTS for controlling growth of micro-organisms. In the former use, due to the fact that there is a small As used in this invention the term N-hydrogen com amount of hypohalite present, the system may safely be pound means a Bronsted acid amide which contains at used to bleach dyed fabrics without adversely affecting the least 1 N-H bond. That is, N-hydrogen compounds are fabric or the dye. In the latter case, the slow release of 20 those having an N-H or NH2 group adjacent to an hypochlorite minimizes undesirable side reactions, such electron withdrawing functional group such as C=O, as the corrosion of the process equipment and attack on S=O or P-O. In this invention N-hydrogen compounds materials other than the micro-organisms. are limited to those having a dissociation constant (pKb) Dichlorosulfamates decompose under highly alkaline greater than 5 with the proviso that the conjugate base conditions (pH>11), forming nitrogen gas, sulfate, and 25 of the Bronsted acid is not halogen or halogen oxide. chloride, and under acid conditions, by hydrolysis, to Examples are below: chloramines and sulfuric acid. In either case, decomposi tion causes the system to become more acid. This de composition is relatively slow at pH's between 4 and 11, Acid Acid amide derivative but under extreme acid or alkaline conditions, the de 30 Hydrogen cyanide-------- Cyanamide, dicyandiamide, melamine. Carbonic acid------------ Ethyl carbamate, urea, thiourea, 1,3-di composition becomes rapid. Heretofore, compositions of methylbiuret, methyl phenylbiuret, iso N,N-dichlorosulfamates have not been synthesized in high cyaniric acid, barbituric acid, 6-methyl yield (>90%) since, in the prior art syntheses, the pH 5,5-dimethylhydantoin,uracil, uron, 2-imidazolinone, 2-pyrimidinone. ethylene urea, was allowed to stray outside these limits.
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