MXPA97003102A - Compaction of halohidantoin and amida grasa yproducto de la mi - Google Patents
Compaction of halohidantoin and amida grasa yproducto de la miInfo
- Publication number
- MXPA97003102A MXPA97003102A MXPA/A/1997/003102A MX9703102A MXPA97003102A MX PA97003102 A MXPA97003102 A MX PA97003102A MX 9703102 A MX9703102 A MX 9703102A MX PA97003102 A MXPA97003102 A MX PA97003102A
- Authority
- MX
- Mexico
- Prior art keywords
- composition
- ethylene
- fatty amide
- group
- methyl
- Prior art date
Links
- 238000005056 compaction Methods 0.000 title claims abstract description 12
- 241000670727 Amida Species 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 42
- 239000007787 solid Substances 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- -1 amide fatty acid Chemical class 0.000 claims abstract description 8
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 6
- 239000000194 fatty acid Substances 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000460 chlorine Substances 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 150000002193 fatty amides Chemical class 0.000 claims description 36
- RKISUIUJZGSLEV-UHFFFAOYSA-N N-[2-(octadecanoylamino)ethyl]octadecanamide Chemical group CCCCCCCCCCCCCCCCCC(=O)NCCNC(=O)CCCCCCCCCCCCCCCCC RKISUIUJZGSLEV-UHFFFAOYSA-N 0.000 claims description 24
- 239000000047 product Substances 0.000 claims description 18
- 239000005977 Ethylene Substances 0.000 claims description 16
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 16
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 10
- 239000011230 binding agent Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- PIICEJLVQHRZGT-UHFFFAOYSA-N 1,2-ethanediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 150000004665 fatty acids Chemical class 0.000 claims description 5
- FWXPXBWRCSMEIY-UHFFFAOYSA-N 16-methyl-N-[2-(16-methylheptadecanoylamino)ethyl]heptadecanamide Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)NCCNC(=O)CCCCCCCCCCCCCCC(C)C FWXPXBWRCSMEIY-UHFFFAOYSA-N 0.000 claims description 4
- ORAWFNKFUWGRJG-UHFFFAOYSA-N Docosanamide Chemical compound CCCCCCCCCCCCCCCCCCCCCC(N)=O ORAWFNKFUWGRJG-UHFFFAOYSA-N 0.000 claims description 4
- 229940116335 LAURAMIDE Drugs 0.000 claims description 4
- HETBCUMLBCUVKC-UHFFFAOYSA-N N-[2-(dodecanoylamino)ethyl]dodecanamide Chemical compound CCCCCCCCCCCC(=O)NCCNC(=O)CCCCCCCCCCC HETBCUMLBCUVKC-UHFFFAOYSA-N 0.000 claims description 4
- 229940037312 STEARAMIDE Drugs 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- HSEMFIZWXHQJAE-UHFFFAOYSA-N hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(N)=O HSEMFIZWXHQJAE-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 claims description 4
- LTHCSWBWNVGEFE-UHFFFAOYSA-N octanamide Chemical compound CCCCCCCC(N)=O LTHCSWBWNVGEFE-UHFFFAOYSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 2
- 125000004432 carbon atoms Chemical group C* 0.000 claims 6
- VRLDVERQJMEPIF-UHFFFAOYSA-N DBDMH Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 claims 3
- ARGMAZDAEWCYMG-UHFFFAOYSA-N N-[2-(nonanoylamino)ethyl]nonanamide Chemical compound CCCCCCCCC(=O)NCCNC(=O)CCCCCCCC ARGMAZDAEWCYMG-UHFFFAOYSA-N 0.000 claims 3
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims 3
- VSJRBQDMBFFHMC-UHFFFAOYSA-N 5-ethyl-5-methylimidazolidine-2,4-dione Chemical compound CCC1(C)NC(=O)NC1=O VSJRBQDMBFFHMC-UHFFFAOYSA-N 0.000 claims 2
- UAXZKOFYXXDTFH-UHFFFAOYSA-N N-[2-(hexadecanoylamino)ethyl]hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(=O)NCCNC(=O)CCCCCCCCCCCCCCC UAXZKOFYXXDTFH-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 abstract description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
- 235000019359 magnesium stearate Nutrition 0.000 description 8
- 239000000654 additive Substances 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 230000000996 additive Effects 0.000 description 3
- 230000003247 decreasing Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000004328 sodium tetraborate Substances 0.000 description 3
- 235000010339 sodium tetraborate Nutrition 0.000 description 3
- ZKEDCOQHFGQDFW-UHFFFAOYSA-N N-[2-(octanoylamino)ethyl]octanamide Chemical compound CCCCCCCC(=O)NCCNC(=O)CCCCCCC ZKEDCOQHFGQDFW-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000035939 shock Effects 0.000 description 2
- 230000035882 stress Effects 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- PIEXCQIOSMOEOU-UHFFFAOYSA-N 1-bromo-3-chloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Br)C(=O)N(Cl)C1=O PIEXCQIOSMOEOU-UHFFFAOYSA-N 0.000 description 1
- GSDQVZMTWWSMNU-UHFFFAOYSA-N 1-chloroimidazolidine-2,4-dione Chemical compound ClN1CC(=O)NC1=O GSDQVZMTWWSMNU-UHFFFAOYSA-N 0.000 description 1
- PQRDTUFVDILINV-UHFFFAOYSA-N BCDMH Chemical compound CC1(C)N(Cl)C(=O)N(Br)C1=O PQRDTUFVDILINV-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- NOPVNWCIHNOJKG-UHFFFAOYSA-N CO[NH-] Chemical compound CO[NH-] NOPVNWCIHNOJKG-UHFFFAOYSA-N 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N Hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N N-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 description 1
- WNCFYFLYHFIWIL-UHFFFAOYSA-N N-[2-(docosanoylamino)ethyl]docosanamide Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)NCCNC(=O)CCCCCCCCCCCCCCCCCCCCC WNCFYFLYHFIWIL-UHFFFAOYSA-N 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M Sodium stearate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 230000003115 biocidal Effects 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L cacl2 Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 150000001469 hydantoins Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000001050 lubricating Effects 0.000 description 1
- 238000005461 lubrication Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000135 prohibitive Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004642 transportation engineering Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Abstract
The present invention relates to a composition for compaction comprising a mixture of: A) at least one N-halohydantoin having the formula: wherein R1 and R2 are independently selected from lower alkyl groups having from 1 to 12 carbons , and wherein X1 and X2 are independently selected from the group consisting of bromine, chlorine and hydrogen, at least one of X1 and X2 being halogen, and B) an amount of a saturated, usually solid, amide fatty acid effective to agglutinate said composition
Description
COMPOSITION OF HALOHIDANTOI NA AND GREASE AMID AND PRODUCT THEREOF BACKGROUND OF THE INVENTION The N-halohydantoin compounds are commercially used in industrial and recreational water treatment to provide biocidal action and to control the growth of bacteria. Recently, these compounds have also been used in automatic domestic toilet bowl cleaners. Examples of N-halohydantoins which are currently being used in these applications include N, N'-dichloro and N, N'-dibromo derivatives, as well as mixtures of N, N'-chloro and -bromo derivatives. The N-halohydantoin compounds are normally produced as solid particles. They are often compacted by mechanical pressure in forms such as agglomerates, tablets and discs. These "compacts" are usually subject to various stresses and shocks during packaging, transportation and end use.
Because of this, it is highly convenient to have a composition for compaction that is not only easily molded, but also better resists stresses and shocks. Several binders have been used in the compaction process. However, most organic materials can not be used as binders with N-halohydantoins given the strong oxidation properties of N-halodantoins. Severe reactivity with the N-halohydantoins results in substantial discoloration of the finished product.
The Patent of E. U.A. No. 3,412,021 teaches the use of polymers as binders, with copious amounts of water, to form 1-bromo-3-chloro-5,5-dimethylhydantoin in bars or rods. A paste is made consisting of at least 25% water. However, excess water renders the polymers inactive, thus preventing healing. The resulting compacts are not acceptable. In addition, the compacts formed by this process are not as hard as is convenient, unless a drying process is carried out by subsequent application. The cost of evaporating water to form an acceptable product is prohibitive. The patent of E. U.A. 4,677, 130, describes the addition of alkali metal or alkaline earth metal salts in dried particles to N-halohydantoins, and then compaction. While this process does not require water (as in the patent of US Pat. No. 3,412,021), the use of alkaline earth metal salts has several disadvantages. For example, while the compactor formed, v.gr. , using magnesium stearate, it is thermally stable, has a lower decomposition temperature (measured by differential scanning calorimetry). This is caused by the reaction between N-halohydantoin and the alkaline earth metal salt. The discoloration of the products results when the ambient temperature is not sufficiently controlled. Nor is it possible to modify the dissolution rate of N-halohydantoin using alkaline salts. It is convenient to modify the dissolution rate, for example, to extend the functional lives of toilet bowl cleaners and urinal tablets.
Canadian patent 1, 230, 825 describes the use of borax (e.g., Na2B O7.5H2O) as a binder for N-halogenated hydantoins. The addition of borax produces tablets that are essentially dust-free, have a high minimum breaking strength and have dissolution characteristics that can be modified by varying the amount of borax. However, the Indian patent requires a separate additive, such as stearic acid or sodium stearate to lubricate die surfaces. Said additives melt at low temperatures (e.g., 55-56 ° C), resulting in a markedly lower decomposition temperature for the compacted products. SUMMARY OF THE INVENTION Fatty, saturated, normally solid amides have been found to be fully compatible with N-halohydantoins to form compacted products, while at the same time lubricating and processing surfaces. The fatty amides also increase the resistance to collapse and decrease the rate of dissolution of the compacted product. In a modality, the invention relates to a composition for compaction comprising an N-halohydrintoin and an effective amount of a saturated, normally solid, amide binder. In another embodiment, the invention relates to a method for forming compacted N-halo-oxydantoin wherein the N-halo-oxydantoin is mixed with the fatty amide and then compressed to form a compacted product. In another embodiment, the invention relates to the compacted product of N-halohydrogentoin and fatty amide. Brief Description of the Drawings Fatty, saturated, normally solid amide waxes can be used to compact haiohydantoins in order to provide stable final forms. Conventional compacted forms, including tablets, agglomerates and pellets, can be made using this invention. However, it is also intended that the word "compacted" encompass any other products resulting from the compression of N-halohydantoins, such as granules, bars and other agglomerates. "Normally solid" refers to fatty amides that are solid at room temperature. The compacted forms according to the invention show markedly increased resistance to collapse and rupture. Additionally, they show better thermal stability than those made with, for example, alkaline earth metal salts such as magnesium stearate (a conventional binder / lubricant used in N-halohydantoin forming operations). In this invention, N-haiohydantoin compounds of the formula shown can be used.
Ri and R2 are independently selected from alkyl groups (having 1 to 12 carbons), and Xi and X2 are independently selected from bromine, chlorine and hydrogen, at least one of Xi and X2 being halogen. In preferred embodiments, R ^ is methyl and R2 is either methyl or ethyl. Preferred haiohydantoins include 1, 3-d-chloro-5,5-d-methyl-hydantoin; 1, 3-d i bromo-5,5-di methylenithine; and combinations of these derivatives. Another preferred embodiment includes a mixture of halogen derivatives of 5-methyl-5-ethylhydantoin, such as, the mixtures currently sold under the trade names Dantobrom® RW and Dantochlor®. Examples of saturated, normally solid, amides which can be combined with N-halohydantoins include primary fatty amides having from 6 to 22 carbons, such as stearamide, palmitamide, caprylamide, lauramide, and behenamide, and secondary fatty amides. The secondary fatty amides which are the reaction products of ethylenediamine and fatty acids containing from 6 to 22 carbons are preferred. Most preferred of this type are ethylene bis-stearamide (EBS) and ethylene bisisostearamide. Ethylene bisamides can be synthesized from a variety of fatty acids and ethylenediamine. All have exceptionally high melting points for organic waxes and, interestingly, their melting point with decreasing molecular weight is increased. As shown by the examples in Table 1, the melting points are increased from 124 ° C for ethylene [N-stearamide, N'-cyclohexyl (methoxyamide)] to a high of 166 ° C for ethylene biscaprylamide. TABLE 1 ETHYLENE BISAMIDE FUSION SCALE (° C) Ethylene biscaprylamide 166-168 Ethylene bisperalgamide 159- 165 Ethylene bislauramide 154- 159 [N-stearamide, N'-benzoamide] ethylene Bispalmitamide ethylene 147- 150 Bistearamide ethylene 140-145 Ethylene bisbehenamide 139 [N-stearamide, N'-cyclohexyl (methoxamide)] ethylene It has been found that even small amounts of fatty amide provide significant benefits, such as increased hardness of the compacted product, increased stability and Lubrication during compaction. The amount of fatty amide is preferably from about 0.1% to about
% by weight. In a preferred embodiment, the amount of fatty amide is about 10% by weight. The fatty amide can be conventionally mixed with the N-halohydantoin using a commercially available mixer.
Examples of such mixers are a cone mixer V (Paterson-Kelley), a "Henschel" type mixer, a ball mill and a rotary cone mixer. If desired, other additives may be employed, including inorganic salts such as borate and calcium chloride. To compact the stirred mixture, conventional equipment can be used, such as an agglomerate forger, pelletizer, granulator (Chilsinator), slam press, "Carver" type press, "Bepex" compactor, or rotary tablet press. In some cases, a previous compaction step can be used to produce a granular product. For example, corrugated sheets can be formed, and then broken to form granules. Also, if desired, the compacted product can be broken into a specific sieve size and used for subsequent compaction. It is intended that the following examples illustrate the invention, but not in such a way as to limit its scope. EXAMPLE 1 1, 3-d icloro-5,5-di methyl h ida ntoi na / 1,3-d-chloro-5-ethyl-5-methylhydantoin (DCDMH / DCMH) (Dantoclor®), and a bromo- Mixed chlorohydantoin (BCHM) (Dantobrom RW®) was mixed with ethylene bisestearamide (EBS). The mixtures were prepared by mixing by hand until a homogeneous powder was obtained. The compaction was carried out using a Carver press. The tablets were prepared in 2.54 cm cubes compacted for 5 seconds at a pressure of 9,000 kg. Samples and storage temperatures are displayed immediately: TABLE 2 MU ESTRA TEMP. OBSERVATION
50% DCDMH / DCEMH 26 ° C Hard White Tablet
50% EBS Same 50 ° C Hard White Tablet
50% BCHM 26 ° C Hard White Tablet
50% EBS Same 50 ° C Hard White Tablet
In each case, after 1 month, the compacted mass remained as a hard white tablet. This shows that there was no adverse reaction between N-haloohyntho- nin and EBS, even at considerably higher temperatures than those normally experienced in storage areas during the summer. EXAMPLE 2 DCDMH / DCEMH and EBS were compacted to form tablets of 10 g at the following ratios: 100: 0; 98: 2; 95: 5; 90: 10; 80:20; and 50:50. Each tablet was placed in a separate jar and fixed to a rotating apparatus that rotated the tablets for three hours. The samples were taken every twenty minutes during the first hour and then every hour. As shown in Figure 1, the tablet visibly decreased in proportion to the weight of the EBS present. Interestingly, the addition of only 2% by weight of EBS was visibly reduced by 25%, measured by the weight of the remaining tablet against the weight loss of morons and fines. Even at this low level of additive, a significant increase in tablet integrity resulted. Additional gains in tablet integrity were achieved at high levels of EBS, up to the mixture of DCDMH / DCEMH: EBS at 50:50. EXAMPLE 3 Each tablet of Example 2 was evaluated for hardness using an Instron ™ multi-purpose tester. Figure 2 indicates the relative hardness of each compact. As shown, the hardness of the tablet increased dramatically only with small additions of EBS. EXAMPLE 4 Tablets prepared with 95% DCDMH / DCEMH and 5%
EBS were compared with tablets containing 95% DCDMH / DCEMH and 5% magnesium stearate, using differential scanning calorimetry (CBD). The CBD data was analyzed to determine the principle of decomposition and exothermic heat. The results are shown in Table 3.
TABLE 3 MU ESTRA TEMP. DESC. (° C) EXOTERMIA (CAL / G)
BCHM 182 75.6 95% BCHM 167 175.2 5% EBS 95% BCHM 142 220.0 5% Magnesium stearate
These results demonstrate the improved inherent stability of N-haloohynditoin tablets containing EBS compared to tablets containing magnesium stearate. As shown, the BCHM by itself decomposes at 182 ° C. When 5% magnesium stearate was used, the temperature was only reduced to 167 ° C. This shows that EBS is a more stable chemical additive for N-halohydantoins than magnesium stearate. In addition, when decomposition occurred, less exotherm was observed with EBS than with magnesium stearate. This also indicates superior stability of EBS. It was also found that the addition of EBS to haiohydantoins decreases the rate of dissolution of N-halohydantoin tablets (Figure 3). As little as 2% of EBS substantially decreased the dissolution rate of DCDMH / DCHMH and BCHM (measured ppm total halogen). EXAMPLE 5 The effect of various amounts of ethylenebisamide on the integrity of the tablet, when combined with bromochlorodimethylhydantoin (BCDMH) is shown in Table 4. Tablets were formed as described in Example 1. TABLE 4 BCDMH / EBS Appearance of Tablet 100/0 Tablet torn, flaked 95/5 Slightly separated 90/10 Tablet with good solidity
As shown, the addition of 10% ethylene bisestearamide markedly improved tablet compaction and integrity, allowing the BCDMH to be tabletted without the need for other additives or binders.
Claims (30)
- CLAIMS 1. A composition for compaction comprising a mixture of: (A) at least one N-haloohynditoin having the formula: wherein Rt and R2 are independently selected from lower alkyl groups having from 1 to 12 carbons, and wherein X and X2 are independently selected from the group consisting of bromine, chlorine and hydrogen, at least one of X and X2 being halogen; and (B) an amount of a saturated, normally solid, fatty amide effective to bind said composition.
- 2. The method of claim 1, wherein Rt is methyl and R2 is methyl or ethyl.
- 3. The composition of claim 1, wherein said fatty amide is a primary fatty amide having from 6 to 22 carbon atoms.
- The composition of claim 3, wherein said fatty amide is selected from the group consisting of stearamide, palmitamide, caprylamide, lauramide, and behenamide.
- 5. The composition of claim 1, wherein said fatty amide is a reaction product of ethylenediamine a fatty acid having from 6 to 22 carbon atoms.
- The composition of claim 5, wherein said fatty amide is selected from the group consisting of ethylene bisestearamide, ethylene bisisostearamide, ethylene biscaprilamide, ethylene bispelargamide, ethylene bislauramide, and ethylene bispalmitamide.
- The composition of claim 6, wherein said fatty amide is ethylene bis-stearamide.
- The composition of claim 1, wherein said N-halohydantoin is selected from the group consisting of 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin and a halogen derivative of 5-methyl-5-ethylhydantoin.
- 9. The composition of claim 1, comprising two N-halohydantoins mixed with said fatty amide.
- 10. A method for forming a compacted N-halo-oxytocin product comprising: (A) mixing at least one N-halohydantoin having the following formula: wherein R% and R2 are independently selected from lower alkyl groups having from 1 to 12 carbons, and wherein X- and X are independently selected from the group consisting of bromine, chlorine and hydrogen, at least one of X ^ and X2 being halogen; with an amount of a saturated fatty amide, usually solid, effective to bind said product; and (B) compressing the mixture to form said compacted N-halohydantoin product. eleven .
- The method of claim 10, wherein Ri is methyl and R2 is methyl or ethyl.
- The composition of claim 10, wherein said fatty amide is a primary fatty amide having from 6 to 22 carbon atoms.
- The composition of claim 10, wherein said fatty amide is selected from the group consisting of stearamide, palmitamide, caprylamide, lauramide, and behenamide.
- The composition of claim 10, wherein said fatty amide is a reaction product of ethylenediamine a fatty acid having from 6 to 22 carbon atoms.
- 15. The composition of claim 14, wherein said fatty amide is selected from the group consisting of ethylene bistearamide, ethylene bisisostearamide, ethylene biscaprilamide, ethylene bispelargamide, ethylene bislauramide, and ethylene bispalmithamide.
- 16. The composition of claim 15, wherein said fatty amide is ethylene bis-stearamide.
- The composition of claim 10, wherein said N-halohydantoin is selected from the group consisting of 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin and a halogen derivative. of 5-methyl-5-ethylhydantoin.
- 18. The composition of claim 10, comprising two N-halohydantoins mixed and compressed.
- 19. A product of compacted N-halo-oxytocin comprising: (A) at least one N-haloohynditoin having the formula: wherein Rt and R2 are independently selected from lower alkyl groups having from 1 to 12 carbons, and wherein X and X2 are independently selected from the group consisting of bromine, chlorine and hydrogen, at least one of X and X2 being halogen; and (B) an amount of a saturated, normally solid, fatty amide effective to bind said composition.
- The method of claim 19, wherein Ri is methyl and R2 is methyl or ethyl. twenty-one .
- The composition of claim 19, wherein said fatty amide is a primary fatty amide having from 6 to 22 carbon atoms.
- The composition of claim 16, wherein said fatty amide is selected from the group consisting of stearamide, palmitamide, caprylamide, lauramide, and behenamide.
- 23. The composition of claim 19, wherein said fatty amide is a reaction product of ethylenediamine a fatty acid having from 6 to 22 carbon atoms.
- The composition of claim 23, wherein said fatty amide is selected from the group consisting of ethylene bisestearamide, ethylene bisisostearamide, ethylene biscaprilamide, ethylene bispelargamide, ethylene bislauramide, and ethylene bispalmithamide.
- 25. The composition of claim 24, wherein said fatty amide is ethylene bis-stearamide.
- 26. The composition of claim 19, wherein said N-halohydantoin is selected from the group consisting of 1,3-dichloro-5,5-dimethylhydantoin, 1,3-dibromo-5,5-dimethylhydantoin and a halogen derivative. of 5-methyl-5-ethylhydantoin.
- The composition of claim 26, wherein said N-halohydantoin is a halogen derivative of 5-methyl-5-ethylhydanothine.
- 28. The composition of claim 19, wherein said fatty amide is present in an amount between 0.1% and 25% by weight of said composition.
- 29. The composition of claim 19, wherein said fatty amide is present in an amount equal to about 10% by weight of said composition.
- 30. In a process for compacting an N-haloohydantoin, wherein said N-haloohydantoin is mixed with a binder and compressed to form a compacted product, the improvement comprising using a saturated fatty amide, usually solid as the binder. SUMMARY The N-halohydantoins are advantageously compacted with saturated, normally solid, amides.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/330,251 US5565576A (en) | 1994-10-27 | 1994-10-27 | Halohydantoin and fatty amide composition for compaction, process of compacting and product produced thereby |
US08330251 | 1994-10-27 |
Publications (2)
Publication Number | Publication Date |
---|---|
MX9703102A MX9703102A (en) | 1998-07-31 |
MXPA97003102A true MXPA97003102A (en) | 1998-11-09 |
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