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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US
United States
Prior art keywords
bridged
compound
halotriazine
compounds
composition according
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US343576A
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English (en)
Inventor
Frank Fred Loffelman
Thomas Eugene Brady
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Priority to US343576A priority Critical patent/US3907698A/en
Priority to AU65718/74A priority patent/AU6571874A/en
Priority to AR252502A priority patent/AR203840A1/es
Priority to IT49216/74A priority patent/IT1004369B/it
Priority to NL7403230A priority patent/NL7403230A/xx
Priority to DE2412952A priority patent/DE2412952A1/de
Priority to JP49030658A priority patent/JPS49127881A/ja
Priority to BR742144A priority patent/BR7402144D0/pt
Priority to FR7409573A priority patent/FR2222431B1/fr
Priority to BE142219A priority patent/BE812565A/xx
Priority to DD177355A priority patent/DD111421A5/xx
Application granted granted Critical
Publication of US3907698A publication Critical patent/US3907698A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/39Organic or inorganic per-compounds
    • C11D3/3902Organic or inorganic per-compounds combined with specific additives
    • C11D3/3905Bleach activators or bleach catalysts
    • C11D3/3907Organic compounds
    • C11D3/3917Nitrogen-containing compounds
    • C11D3/392Heterocyclic compounds, e.g. cyclic imides or lactames
    • CCHEMISTRY; METALLURGY
    • C02TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02FTREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00Treatment of water, waste water, or sewage
    • C02F1/50Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
    • CCHEMISTRY; METALLURGY
    • C02TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02FTREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00Treatment of water, waste water, or sewage
    • C02F1/72Treatment of water, waste water, or sewage by oxidation
    • C02F1/722Oxidation 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.

Landscapes

  • 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)
  • Wood Science & Technology (AREA)
  • Detergent Compositions (AREA)
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 (es) 1973-03-21 1974-02-22 Composicion de blanqueo activada con una halotriazina
IT49216/74A IT1004369B (it) 1973-03-21 1974-03-08 Composizione candeggiante
NL7403230A NL7403230A (xx) 1973-03-21 1974-03-11
DE2412952A DE2412952A1 (de) 1973-03-21 1974-03-18 Gekoppelte halogentriazine als bleichaktivatoren
JP49030658A JPS49127881A (xx) 1973-03-21 1974-03-19
BR742144A BR7402144D0 (pt) 1973-03-21 1974-03-19 Composicao alvejante ativada aperfeicoada
FR7409573A FR2222431B1 (xx) 1973-03-21 1974-03-20
BE142219A BE812565A (fr) 1973-03-21 1974-03-20 Compositions de blanchiment contenant des triazines halogenees pontees comme activateurs de blanchiment
DD177355A DD111421A5 (xx) 1973-03-21 1974-03-21

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US343576A US3907698A (en) 1973-03-21 1973-03-21 Bridged halotriazine compounds as bleach activators

Publications (1)

Publication Number Publication Date
US3907698A true US3907698A (en) 1975-09-23

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ID=23346670

Family Applications (1)

Application Number Title Priority Date Filing Date
US343576A Expired - Lifetime US3907698A (en) 1973-03-21 1973-03-21 Bridged halotriazine compounds as bleach activators

Country Status (11)

Country Link
US (1) US3907698A (xx)
JP (1) JPS49127881A (xx)
AR (1) AR203840A1 (xx)
AU (1) AU6571874A (xx)
BE (1) BE812565A (xx)
BR (1) BR7402144D0 (xx)
DD (1) DD111421A5 (xx)
DE (1) DE2412952A1 (xx)
FR (1) FR2222431B1 (xx)
IT (1) IT1004369B (xx)
NL (1) NL7403230A (xx)

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

Also Published As

Publication number Publication date
AU6571874A (en) 1975-08-21
FR2222431A1 (xx) 1974-10-18
BE812565A (fr) 1974-09-20
FR2222431B1 (xx) 1977-10-07
DE2412952A1 (de) 1974-09-26
IT1004369B (it) 1976-07-10
JPS49127881A (xx) 1974-12-06
NL7403230A (xx) 1974-09-24
BR7402144D0 (pt) 1974-11-05
DD111421A5 (xx) 1975-02-12
AR203840A1 (es) 1975-10-31

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