US3907698A - Bridged halotriazine compounds as bleach activators - Google Patents

Bridged halotriazine compounds as bleach activators Download PDF

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Publication number
US3907698A
US3907698A US343576A US34357673A US3907698A US 3907698 A US3907698 A US 3907698A US 343576 A US343576 A US 343576A US 34357673 A US34357673 A US 34357673A US 3907698 A US3907698 A US 3907698A
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bridged
compound
halotriazine
compounds
composition according
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US343576A
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Frank Fred Loffelman
Thomas Eugene Brady
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Wyeth Holdings LLC
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American Cyanamid Co
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Priority to US343576A priority Critical patent/US3907698A/en
Priority to AU65718/74A priority patent/AU6571874A/en
Priority to AR252502A priority patent/AR203840A1/en
Priority to IT49216/74A priority patent/IT1004369B/en
Priority to NL7403230A priority patent/NL7403230A/xx
Priority to DE2412952A priority patent/DE2412952A1/en
Priority to JP49030658A priority patent/JPS49127881A/ja
Priority to BR742144A priority patent/BR7402144D0/en
Priority to BE142219A priority patent/BE812565A/en
Priority to FR7409573A priority patent/FR2222431B1/fr
Priority to DD177355A priority patent/DD111421A5/xx
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/39—Organic or inorganic per-compounds
    • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
    • C11D3/3905—Bleach activators or bleach catalysts
    • C11D3/3907—Organic compounds
    • C11D3/3917—Nitrogen-containing compounds
    • C11D3/392—Heterocyclic compounds, e.g. cyclic imides or lactames
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/72—Treatment of water, waste water, or sewage by oxidation
    • C02F1/722—Oxidation by peroxides

Definitions

  • A represents a group selected from vinylene, phenylene, biphenylene, stilbyl and ethynylenebis(pphenylene) groups
  • Z represents a group selected from -O, S- or N(H)-
  • n is an integer selected from zero and one
  • X and X individually represent chlorine, bromine or fluorine
  • R and R individually represent halogen, hydroxy, mercapto, alkyl, alkenyl, alkoxy, alkylmercapto, aryl, aryloxy, arylmercapto, dialkoxyphosphinyl or Cl- -NH- "1 Y NQ/N where R and R are as defined in formula I, above.
  • the bleaching compositions of the invention contain the activating compound and the hydrogen peroxidereleasing compound in a molar ratio ranging from about lzl tov about 1210, respectively, with a preferred range of about 1:1 to 1:3.
  • the actual ratio of activator to bleach can, of course, be varied widely for varying applications.
  • oxygen bleaches useful in these bleaching compositions are hydrogen peroxide and organic peroxides and inorganic peroxygen salts that liberate hydrogen peroxide in water.
  • peroxide bleaching compounds are urea peroxide, benzoyl peroxide, methyl ethyl ketone peroxide, and the like.
  • inorganic peroxygen bleaching compounds are alkali metal perborates, percarbonates, perphosphates, persulfates, monopersulfates, and the like. Mixtures of two or more bleaching compounds can, of course, beused if desired. 7
  • peroxide releasing compounds as mentioned above may be used in the compositions of the invention, preferred peroxide-releasing compounds are sodium perborate (for economic considerations) and sodium percarbonate (for ecological considerations).
  • the activated bleach compositions of the invention are useful for bleach applications for various substrates including fabrics, particularly when'incorporated with detergent compositions for household or commercial laundering purposes.
  • a most important property of such detergent compositions is the ability to remove stains including food stains such as those of coffee, tea, wine and the like as well as to maintain purity of white in uncolored textiles.
  • soiling in general may be removed such as grass stains, urine stains and the like.
  • such detergent compositions may contain other optional additives such as germicides, fungicides, enzymes, optical brighteners, colorants, perfumes, thickeners, emulsion or suspension stabilizers, and the like, including builders, such as sodium phosphate, salts, carbonates, silicates, and the like as usually encountered in the art.
  • the detergent component of such activated bleach compositions may be any of the conventional types such as anionic, cationic, nonionic or amphoteric.
  • anionic detergents include the alkali metal or alkaline earth metal salts of higher alkylbenzene sulfonates, olefin sulfonates, higher alkyl sulfates and higher fatty acid monoglyceride sulfates.
  • typically suitable cationic detergents include tetraalkyl ammonium salts in which one of the alkyl groups contains approximately 12 to 18 carbons such as dodecyltrimethylammonium chloride or ethyldimethyloctadecylammonium methosulfate.
  • amphoteric detergents are those detergent compounds possessing both cationic and anionic sites and include, for example, amino fatty acids such as dimethylaminopropionic acid and iminodifatty acids such as methyliminodilauric acid.
  • nonionic detergents examples include polyglycol ethers of alkanol amides of higher fatty acids and also polyglycol-ethers of higher alkanols and higher fatty acids.
  • Bleaching compositions may generally be used also for their germicidal properties in various applications for control of microbial growth. Applications may be made to any surface or substrate where such control is desired.
  • compositions of the invention are especially efficacious since the usually lower temperatures of these environments prevent effective use of other antimicrobial agents.
  • a related utility is the treatment of water supplies to render the same fit for human consumption or for industrial use, such as the sanitization of field water for consumption by military personnel or the treatment of industrial process water so it can be reused in industrial processes or by the surrounding community.
  • the compositions also may be employed in admixture with detergents for use as home or industrial germicidal detergents, or in hair bleaching compositions containing peroxygen compounds.
  • test procedure was as follows: Five-gram swatches of desized, 80 X 80 cotton fabric are stained with tea in the following manner. Five tea bags are 5 before and after laundering using a Hunter Model 25-M Reflectometer with a blue filter. The swatches are backed with a white procelain plate and read once on each side. Fluorescent effect is excluded from all readings.
  • the swatches are then immersed in the tea and the boiling is continued for another five minutes.
  • the swatches are then removed from the tea, wrung out, dried at 2002l5F., rinsed in cold water and again dried.
  • R and R may be hydrogen, cyanoalkyl, carboxyalkyl, ehloroalkyl, alkoxyalkyl, sulfoalkyl, aryl, sulfoaryl, acylaminoaryl or carbamoylalkyl, or where R; and R taken together may be joined to complete a heterocyclic ring selected from morpholine, piperazine and piperidine rings.
  • composition according to claim 1 wherein the mole ratio of the bridged halotriazine compound to the hydrogen peroxide-releasing compound is from about 1:1 to about 1:10
  • a composition according to claim 1 wherein the hydrogen peroxide-releasing compound is sodium perborate or sodium percarbonate.
  • a composition according to claim 3 wherein the bridged halotriazine compound is represented by the formula 5.
  • a composition according to claim 3 wherein the bridged halotriazine compound is represented by the 1H3 EH 6.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Hydrology & Water Resources (AREA)
  • Environmental & Geological Engineering (AREA)
  • Water Supply & Treatment (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
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  • Detergent Compositions (AREA)

Abstract

Bridged halotriazine compounds of the formula

WHERE A represents a group selected from vinylene, phenylene, biphenylene, stilbyl and ethynylenebis(p-phenylene) groups; Z represents a group selected from -O-, -S- or -N(H)-; n is an integer selected from zero and one; X1 and X2 individually represent chlorine, bromine or fluorine; and R1 and R2 individually represent halogen, hydroxy, mercapto, alkyl, alkenyl, alkoxy, alkylmercapto, aryl, aryloxy, arylmercapto, dialkoxyphosphinyl or

WHERE R3 and R4 may be hydrogen, alkyl, cyanoalkyl, hydroxyalkyl, carboxyalkyl, chloroalkyl, alkoxyalkyl, sulfoalkyl, aryl, sulfoaryl, acylaminoaryl or carbamoylalkyl, or where R3 and R4 taken together may be joined to complete a heterocyclic ring selected from morpholine, piperazine and piperidine rings; are effective as bleach activators for peroxygen bleaching compositions.

Description

United States Patent 1 Loffelman et a].
[ 1 Sept. 23, 1975 1 BRIDGED HALOTRIAZINE COMPOUNDS AS BLEACH ACTIVATORS [75] Inventors: Frank Fred Loffelman, Somerville;
Thomas Eugene Brady, Piscataway, both of NJ.
[73] Assignee: American Cyanamid Company,
Stamford, Conn.
22 Filed: Mar. 21, 1973 211 Appl. No.: 343,576
[52] U.S. Cl. 252/99; 252/102; 252/186; 252/543 [51] Int. Cl. ...C11D 3/26; C1 1D 7/32; C11D 7/38; COlB 15/00 [58] Field of Search 252/543, 186,95, 99, 102; 8/111; 260/248 CS [56] References Cited UNITED STATES PATENTS 2,763,650 9/1956 Ackermann 252/99 X 2,956,898 10/1960 Fleck 8/111 X 3,704,228 11/1972 Eckert et a1.. 252/117 3,741,903 6/1973 Evans v. 252/95 Primary Examiner-Benjamin R. Padgett Assistant Examiner-Christine M. Nucker Attorney, Agent, or Firm-John L. Sullivan [57] ABSTRACT Bridged halotriazine compounds of the formula where R, and R may be hydrogen, alkyl, cyanoalkyl, hydroxyalkyl, carboxyalkyl, chloroalkyl, alkoxyalkyl, sulfoalkyl, aryl, sulfoaryl, acylaminoaryl or carbamoylalkyl, or where R and R taken together may be joined to complete a heterocyclic ring selected from morpholine. piperazine and piperidine rings; are effective as bleach activators for peroxygen bleaching compositions.
6 Claims, N0 Drawings BRIDGED HALOTRIAZINE COMPOUNDS AS BLEACH ACTIVATORS This invention relates to bleaching compositions and more particularly to improved bleaching compositions comprising hydrogen peroxide or hydrogen peroxidereleasing compound and as an activator for the peroxide-releasing compound a bridged halotriazine represented by the formula:
where A represents a group selected from vinylene, phenylene, biphenylene, stilbyl and ethynylenebis(pphenylene) groups; Z represents a group selected from -O, S- or N(H)-; n is an integer selected from zero and one; X and X individually represent chlorine, bromine or fluorine; and R and R individually represent halogen, hydroxy, mercapto, alkyl, alkenyl, alkoxy, alkylmercapto, aryl, aryloxy, arylmercapto, dialkoxyphosphinyl or Cl- -NH- "1 Y NQ/N where R and R are as defined in formula I, above.
As illustrative of compounds which can be used as activators in the bleach compositions of the present invention, there may be mentioned the following.
so r:
W 5 osc- Y scan CHaO-fw Kym H Cla CH- -cl N(CH CH OH) N(CH CH OH) The bleaching compositions of the invention contain the activating compound and the hydrogen peroxidereleasing compound in a molar ratio ranging from about lzl tov about 1210, respectively, with a preferred range of about 1:1 to 1:3. The actual ratio of activator to bleach can, of course, be varied widely for varying applications. I
The. oxygen bleaches useful in these bleaching compositions are hydrogen peroxide and organic peroxides and inorganic peroxygen salts that liberate hydrogen peroxide in water. Examples of peroxide bleaching compounds are urea peroxide, benzoyl peroxide, methyl ethyl ketone peroxide, and the like. Examples of inorganic peroxygen bleaching compounds are alkali metal perborates, percarbonates, perphosphates, persulfates, monopersulfates, and the like. Mixtures of two or more bleaching compounds can, of course, beused if desired. 7
Although the various peroxide releasing compounds as mentioned above may be used in the compositions of the invention, preferred peroxide-releasing compounds are sodium perborate (for economic considerations) and sodium percarbonate (for ecological considerations).
The activated bleach compositions of the invention are useful for bleach applications for various substrates including fabrics, particularly when'incorporated with detergent compositions for household or commercial laundering purposes. A most important property of such detergent compositions is the ability to remove stains including food stains such as those of coffee, tea, wine and the like as well as to maintain purity of white in uncolored textiles. Aside from food stains, soiling in general may be removed such as grass stains, urine stains and the like.
In addition to the detergent, peroxygen-releasing compound and peroxygen bleach activator, such detergent compositions may contain other optional additives such as germicides, fungicides, enzymes, optical brighteners, colorants, perfumes, thickeners, emulsion or suspension stabilizers, and the like, including builders, such as sodium phosphate, salts, carbonates, silicates, and the like as usually encountered in the art.
The detergent component of such activated bleach compositions may be any of the conventional types such as anionic, cationic, nonionic or amphoteric.
Examples of typically suitable anionic detergents include the alkali metal or alkaline earth metal salts of higher alkylbenzene sulfonates, olefin sulfonates, higher alkyl sulfates and higher fatty acid monoglyceride sulfates.
Examples of typically suitable cationic detergents include tetraalkyl ammonium salts in which one of the alkyl groups contains approximately 12 to 18 carbons such as dodecyltrimethylammonium chloride or ethyldimethyloctadecylammonium methosulfate.
Examples of suitably typical amphoteric detergents are those detergent compounds possessing both cationic and anionic sites and include, for example, amino fatty acids such as dimethylaminopropionic acid and iminodifatty acids such as methyliminodilauric acid.
Examples of typical nonionic detergents include polyglycol ethers of alkanol amides of higher fatty acids and also polyglycol-ethers of higher alkanols and higher fatty acids.
Bleaching compositions may generally be used also for their germicidal properties in various applications for control of microbial growth. Applications may be made to any surface or substrate where such control is desired.
The treatment of swimming pool water and swimming pool surfaces with the compositions of the invention is especially efficacious since the usually lower temperatures of these environments prevent effective use of other antimicrobial agents. A related utility is the treatment of water supplies to render the same fit for human consumption or for industrial use, such as the sanitization of field water for consumption by military personnel or the treatment of industrial process water so it can be reused in industrial processes or by the surrounding community. The compositions also may be employed in admixture with detergents for use as home or industrial germicidal detergents, or in hair bleaching compositions containing peroxygen compounds.
The following examples and tests will serve to illustrate the invention.
EXAMPLES l and 2 Evaluation of Compounds as Bleach Activators Representative bridged halotriazine compounds of the invention were evaluated as bleach activators applied with sodium perborate and a detergent. In the evaluation tests, the mole ratio of activator used to sodium perborate was 1:1.1, although a lesser amount of activator was also tested.
The test procedure was as follows: Five-gram swatches of desized, 80 X 80 cotton fabric are stained with tea in the following manner. Five tea bags are 5 before and after laundering using a Hunter Model 25-M Reflectometer with a blue filter. The swatches are backed with a white procelain plate and read once on each side. Fluorescent effect is excluded from all readings.
The reflectance readings are averaged and the pera cent stain removal is obtained in accordance with the following formula in which R is the symbol for Reflectance:
R (bleached) minus R (stained) Total Stam removal: R (unstained) minus R (stained) Control runs are also made foreach set or'series of evaluation tests using detergent and sodium perborate r with nolactivator. The percent stain removed may vary somewhat on the Control due to variations in the cloth and the tea used to produce the stains.
The test results obtained are shown in Table I wherein the activator compounds tested are identified by the R and R radicals thereof in the general formula shown at the top of the Table.
TABLE I H 01- I -N- ca=cn- N T 03H 7c Stain Removed Wgt. of Activator Ex. No. R R2 (Control) (g.) Stain Removed 1 -N-H NH 35.9 2.50 45.5 .50 42.8
2 -ocH., -0CH 35.9 2.50 55.6 .50 40.4
placed in one liter of water and boiled for five minutes. We claim:
The swatches are then immersed in the tea and the boiling is continued for another five minutes. The swatches are then removed from the tea, wrung out, dried at 2002l5F., rinsed in cold water and again dried.
Two of the stained cotton swatches are placed in a stainless steel Terg-O-Tometer, a test washing machine, manufactured by U.S. Testing Company and used in the detergent trade for evaluation purposes. Forty grams of unstained cotton fabric and one liter of distilled water at F. are then added so as to provide a typical household washing machine water to cloth ratio of about 20:1. There are then added 2.0 grams of Tide (an anionic alkylaryl sulfonate type detergent), 0.33 gram of anhydrous sodium perborate (or an equivalent of hydrated material) and the indicated amount of the activator compound. The Terg-O-Tometer is op- 1. An activated bleaching composition comprising hydrogen peroxide or a hydrogen peroxide-releasing compound and an activating amount of a bridged halo triazine compound represented by the formula:
where R and R may be hydrogen, cyanoalkyl, carboxyalkyl, ehloroalkyl, alkoxyalkyl, sulfoalkyl, aryl, sulfoaryl, acylaminoaryl or carbamoylalkyl, or where R; and R taken together may be joined to complete a heterocyclic ring selected from morpholine, piperazine and piperidine rings.
2. A composition according to claim 1 wherein the mole ratio of the bridged halotriazine compound to the hydrogen peroxide-releasing compound is from about 1:1 to about 1:10,
3. A composition according to claim 1 wherein the hydrogen peroxide-releasing compound is sodium perborate or sodium percarbonate.
4. A composition according to claim 3 wherein the bridged halotriazine compound is represented by the formula 5. A composition according to claim 3 wherein the bridged halotriazine compound is represented by the 1H3 EH 6. A composition according to claim 1 containing a detergent.

Claims (6)

1. AN ACTIVATED BLEACHING COMPOSITION COMPRISING HYDROGEN PEROXIDE OR A HYDROGEN PEROXIDE-RELEASING COMPOUND AND AN ACTIVATING AMOUNT OF A BRIDGED HALO TRIAZINE COMPOUND REPRESENTED BY THE FROMULA:
2. A composition according to claim 1 wherein the mole ratio of the bridged halotriazine compound to the hydrogen peroxide-releasing compound is from about 1:1 to about 1:10.
3. A composition according to claim 1 wherein the hydrogen peroxide-releasing compound is sodium perborate or sodium percarbonate.
4. A composition according to claim 3 wherein the bridged halotriazine compound is represented by the formula
5. A composition according to claim 3 wherein the bridged halotriazine compound is represented by the formula
6. A composition according to claim 1 containing a detergent.
US343576A 1973-03-21 1973-03-21 Bridged halotriazine compounds as bleach activators Expired - Lifetime US3907698A (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
US343576A US3907698A (en) 1973-03-21 1973-03-21 Bridged halotriazine compounds as bleach activators
AU65718/74A AU6571874A (en) 1973-03-21 1974-02-18 Bridged halotriazines as bleach activators
AR252502A AR203840A1 (en) 1973-03-21 1974-02-22 WHITENING COMPOSITION ACTIVATED WITH A HALOTRIAZINE
IT49216/74A IT1004369B (en) 1973-03-21 1974-03-08 BLEACH COMPOSITION
NL7403230A NL7403230A (en) 1973-03-21 1974-03-11
DE2412952A DE2412952A1 (en) 1973-03-21 1974-03-18 COUPLED HALOGENTRIAZINES AS BLEACH ACTIVATORS
JP49030658A JPS49127881A (en) 1973-03-21 1974-03-19
BR742144A BR7402144D0 (en) 1973-03-21 1974-03-19 PERFECTED ACTIVATED WHITE COMPOSITION
BE142219A BE812565A (en) 1973-03-21 1974-03-20 BLEACHING COMPOSITIONS CONTAINING HALOGENATED TRIAZINES PONTED AS BLEACH ACTIVATORS
FR7409573A FR2222431B1 (en) 1973-03-21 1974-03-20
DD177355A DD111421A5 (en) 1973-03-21 1974-03-21

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JP (1) JPS49127881A (en)
AR (1) AR203840A1 (en)
AU (1) AU6571874A (en)
BE (1) BE812565A (en)
BR (1) BR7402144D0 (en)
DD (1) DD111421A5 (en)
DE (1) DE2412952A1 (en)
FR (1) FR2222431B1 (en)
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NL (1) NL7403230A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3986971A (en) * 1975-11-25 1976-10-19 American Cyanamid Company 2,4-diisocyanato-6-halo-s-triazines as peroxygen bleach activators
US4105501A (en) * 1975-10-23 1978-08-08 Nippon Kokan Kabushiki Kaisha Method for producing metallurgical coke
US4145183A (en) * 1975-12-19 1979-03-20 E. I. Du Pont De Nemours And Company Method for the oxidative treatment of textiles with activated peroxygen compounds
US4820437A (en) * 1986-09-18 1989-04-11 Lion Corporation Bleaching composition
US5087385A (en) * 1986-11-06 1992-02-11 The Clorox Company Acyloxynitrogen peracid precursors
US5760227A (en) * 1994-03-24 1998-06-02 Clariant Finance (Bvi) Limited Compounds of the s-triazine series

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2763650A (en) * 1956-09-18 Derivatives of x
US2956898A (en) * 1960-10-18 Certification of correction
US3704228A (en) * 1969-06-07 1972-11-28 Henkel & Cie Gmbh Washing agents containing a textile softener
US3741903A (en) * 1968-12-12 1973-06-26 Lever Brothers Ltd Detergent compositions

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2763650A (en) * 1956-09-18 Derivatives of x
US2956898A (en) * 1960-10-18 Certification of correction
US3741903A (en) * 1968-12-12 1973-06-26 Lever Brothers Ltd Detergent compositions
US3704228A (en) * 1969-06-07 1972-11-28 Henkel & Cie Gmbh Washing agents containing a textile softener

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4105501A (en) * 1975-10-23 1978-08-08 Nippon Kokan Kabushiki Kaisha Method for producing metallurgical coke
US3986971A (en) * 1975-11-25 1976-10-19 American Cyanamid Company 2,4-diisocyanato-6-halo-s-triazines as peroxygen bleach activators
US4145183A (en) * 1975-12-19 1979-03-20 E. I. Du Pont De Nemours And Company Method for the oxidative treatment of textiles with activated peroxygen compounds
US4820437A (en) * 1986-09-18 1989-04-11 Lion Corporation Bleaching composition
US5087385A (en) * 1986-11-06 1992-02-11 The Clorox Company Acyloxynitrogen peracid precursors
US5760227A (en) * 1994-03-24 1998-06-02 Clariant Finance (Bvi) Limited Compounds of the s-triazine series
US5998306A (en) * 1994-03-24 1999-12-07 Clariant Finance (Bvi) Limited Methods of finishing textile materials

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FR2222431B1 (en) 1977-10-07
BE812565A (en) 1974-09-20
AR203840A1 (en) 1975-10-31
DE2412952A1 (en) 1974-09-26
JPS49127881A (en) 1974-12-06
DD111421A5 (en) 1975-02-12
AU6571874A (en) 1975-08-21
NL7403230A (en) 1974-09-24
BR7402144D0 (en) 1974-11-05
FR2222431A1 (en) 1974-10-18
IT1004369B (en) 1976-07-10

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