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US3912648A - Ring halogen-free substituted triazine compounds as bleach activators - Google Patents

Ring halogen-free substituted triazine compounds as bleach activators Download PDF

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Publication number
US3912648A
US3912648A US343575A US34357573A US3912648A US 3912648 A US3912648 A US 3912648A US 343575 A US343575 A US 343575A US 34357573 A US34357573 A US 34357573A US 3912648 A US3912648 A US 3912648A
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composition according
halogen
ring halogen
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US343575A
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Thomas Eugene Brady
Frank Fred Loffelman
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Wyeth Holdings LLC
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American Cyanamid Co
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Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Priority to US343575A priority Critical patent/US3912648A/en
Priority to CA192,311A priority patent/CA1024702A/en
Priority to GB687074A priority patent/GB1428926A/en
Priority to AU65720/74A priority patent/AU474817B2/en
Priority to AR252501A priority patent/AR203190A1/en
Priority to IT49215/74A priority patent/IT1004368B/en
Priority to NL7403435A priority patent/NL7403435A/xx
Priority to JP49029285A priority patent/JPS49126581A/ja
Priority to DE2412953A priority patent/DE2412953A1/en
Priority to BE142218A priority patent/BE812564A/en
Priority to FR7409572A priority patent/FR2222430B1/fr
Priority to BR2200/74A priority patent/BR7402200D0/en
Priority to DD177356A priority patent/DD111422A5/xx
Application granted granted Critical
Publication of US3912648A publication Critical patent/US3912648A/en
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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

Definitions

  • This invention relates to bleaching compositions and more particularly to improved bleaching compositions comprising hydrogen peroxide or a hydrogen peroxidereleasing compound and as an activator for the peroxide-releasing compound a ring halogen-free triazine derivative represented by the formula:
  • A is a radical selected from pyridinium, dialkoxyphosphinyl, mercapto, (dialkylthiocarbamoyl) thio, alkyl sulfonyl, trihalomethyl and sulfophenoxy radicals; and R and R individually represent hydroxy, mercapto, alkyl, alkenyl, alkoxy, alkylmercapto, aryl, aryloxy, arylmercapto, dialkoxyphosphinyl or 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.
  • alkyl, alkenyl or alkoxy the term is intended to designate lower (i.e., C -C alkyl, lower (i.e., C -C alkenyl or lower (i.e., C -C )alk0xy.
  • ring halogen-free triazine derivatives defined by the above formula are derivatives of striazines, similarly substituted derivatives of unsymmetrical triazine rings are also contemplated as activators for the bleach composition of the invention.
  • Typical halogen-free triazine compounds useful as bleach activators in the bleach compositions of this invention are the following.
  • Thebleaching compositions of the invention contain the activating compound and the hydrogen peroxidereleasing compound in a molar ratio ranging from about 1:1 to about 1:10, respectively, with a preferred range of about 1:1 to l:3.
  • the actual ratio of activator to bleach can', of course, be varied widely for varying applications.
  • the 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, be used if desired.
  • 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 stains. including food stains such as those of coffee, tea,
  • 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 examples include the alkali metal or alkaline earth metal salts of higher alkylbenzene sulfonates, olefin, sulfonates,
  • Example 4-6 The compounds of Examples l-3, plus additional p e o y yp a p c e e gen compounds (Examples 4-6) were evaluated as activaare those detergent compounds possessing both cattonic and anionic sites and include, for example, amino l tors applied wlth and detergemf In fan acids such as dimeth lamino r0 ionic acid and the tests, the mole ratio of activator used to sodium 3 Y P P perborate was l:l.1. tmlnodifatty actds such as methyltmmodllaurtc acid.
  • test procedure was as follows: Five-gram Examples of typical noniontc detergents include d swatches of desized, 80 X 80 cotton fabric are stained polyglycolethers ofalkanolamides ofhigher fatty acids 5 with tea in the following maImeL Five tea bags are and aiscf poiygiycoi ethers of higher aikanois and higher I placed in one liter of water and boiled for five minutes. fatty acids' The swatches are then immersed in the tea and the boil- Bieaching compositions y gonei'aiiy be used aiso ing is continued for another five minutes.
  • the swatches for their germicidal properties in various applications are then removed from the tea wrung out dried at for oomli'oi of microbial growtii- Applications y be 200-2l5F., rinsed in cold water and again dried. made to any surface or substrate where such control is T f h i d cotton Swatches e l d i a desiredstainless steel Terg-O-Tometer, a test washing ma- The treatment of swimming pool water and swimchine, manufactured by U.S. Testing Company and ming pool surfaces with the compositions of the invenused in the detergent trade for evaluation purposes.
  • tion is especially efficacious since the usually lower Forty grams of unstained cotton fabric and one liter of temperatures of these environments prevent effective distilled water at 120F. are then added so as to provide use ofother antimicrobial agents.
  • a related utility is the a typical household washing machine water to cloth treatment of water supplies to render the same fit for ratio of about 20:1.
  • the Terg-O-Tometer is oprounding community.
  • the compositions also may be erated at 100 cycles per minute for fifteen minutes at employed in admixture with detergents for use as home a temperature of 120F.
  • the swatches are then reor industrial germicidal detergents, or in hair bleaching moved, rinsed with cold water, and dried at room temcompositions containing peroxygen compounds. perature.
  • a bleaching composition Comprising hydrogen hydrogen peroxide-releasing compound is sodium perperoxide or a hydrogen peroxide-releasing compound b r t or di -b r and an activating amount ofa ring halogen-free triazine 4.
  • R --A ring-halogen-free triazine compound is represented by I the formula H,CO I-- where A is a radical selected from the group consisting N N Y C19 of pyridinium, dialkoxyphosphinyl, mercapto, (dialkylthiocarbamoy1)thio, alkyl sulfonyl, trihalomethyl and sulfophenoxy radicals; and R and R are individually selected from the group consisting of hydroxy, mercapto, alkyl, alkenyl, alkoxy, alkylmercapto, aryl, aryloxy, arylmercapto, dialkoxyphosphinyl and 6.
  • a composition according to claim 4 wherein the ring halogen-free triazine compound is represented by the formula where R, and R are individually selected from the group consisting of hydrogen, alkyl, cyanoalkyl, hy- N 69 I droxyalkyl, carboxyalkyl, chloroalkyl, alkoxyalkyl, (NCCHZ)2N I/ ⁇ F sulfoalkyl, aryl, sulfoaryl, acylaminoalkyl and carbal moylalkyl, and where R and R taken together are 0 N N joined to complete a heterocyclic ring selected from V the group consisting of morpholine, piperazine and Cle piperidine rings.
  • 4 (OCHQ, 4 I -0- so n I NV" N N O P(OCH so,H.
  • composition according to claim 1 wherein the ring halogen-free triazine compound is represented by th? formula

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  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Ring halogen-free substituted triazine compounds of the formula

WHERE A is a radical selected from pyridinium, dialkoxyphosphinyl, mercapto, (dialkylthiocarbamoyl)thio, alkyl sulfonyl, trihalomethyl and sulfophenoxy radicals; and R1 and R2 individually represent 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 Brady et al.
[4 1 Oct. 14, 1975 RING HALOGEN-FREE SUBSTITUTED TRIAZINE COMPOUNDS AS BLEACH ACTIVATORS [75] Inventors: Thomas Eugene Brady, Piscataway;
Frank Fred Loffelman, Somerville, both of NJ.
[73] Assignee: American Cyanamid Company,
Stamford, Conn.
[22] Filed: Mar. 21, 1973 [21] Appl. No.: 343,575
Primary Examiner-Benjamin R. Padgett Assistant ExaminerB. Hunt Attorney, Agent, or FirmJohn L. Sullivan [57] ABSTRACT Ring halogen-free substituted triazine compounds of the formula where A is a radical selected from pyridinium, dialkoxyphosphinyl, mercapto, (dialkylthiocarbamoyl)thio, alkyl sulfonyl, trihalomethyl and sulfophenoxy radicals; and R and R individually represent hydroxy, mercapto, alkyl, alkenyl, alkoxy, alkylmercapto, aryl, aryloxy, arylmercapto, dialkoxyphosphinyl 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,
10 Claims, No Drawings RING HALOGEN-FREE SUBSTITUTED TRIAZINE COMPOUNDS AS BLEACH ACTIVATORS This invention relates to bleaching compositions and more particularly to improved bleaching compositions comprising hydrogen peroxide or a hydrogen peroxidereleasing compound and as an activator for the peroxide-releasing compound a ring halogen-free triazine derivative represented by the formula:
ll a-A where A is a radical selected from pyridinium, dialkoxyphosphinyl, mercapto, (dialkylthiocarbamoyl) thio, alkyl sulfonyl, trihalomethyl and sulfophenoxy radicals; and R and R individually represent hydroxy, mercapto, alkyl, alkenyl, alkoxy, alkylmercapto, aryl, aryloxy, arylmercapto, dialkoxyphosphinyl or 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. In each instance where alkyl, alkenyl or alkoxy is mentioned, the term is intended to designate lower (i.e., C -C alkyl, lower (i.e., C -C alkenyl or lower (i.e., C -C )alk0xy.
Although the ring halogen-free triazine derivatives defined by the above formula are derivatives of striazines, similarly substituted derivatives of unsymmetrical triazine rings are also contemplated as activators for the bleach composition of the invention.
Typical halogen-free triazine compounds useful as bleach activators in the bleach compositions of this invention are the following.
OCH
Ila
l man),
Lon
l CCh Thebleaching compositions of the invention contain the activating compound and the hydrogen peroxidereleasing compound in a molar ratio ranging from about 1:1 to about 1:10, respectively, with a preferred range of about 1:1 to l:3. The actual ratio of activator to bleach can', of course, be varied widely for varying applications.
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, be used if desired.
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 stains. including food stains such as those of coffee, tea,
. stains and the like.
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 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 monoglycer- Ex. ide sulfates. No. R, R Yield M.P.
Examples of typically suitable cationic detergents in- 1 N(CH2CN)2 N(CHZCN)Z 60% 246448 dm clude tetraalkyl ammonium salts in which one of the 2 cu o- CH 74% 13s mc. dec. alkyl groups contains approximately 12 to 18 carbons 5 3 CHQO N(CH2CN)= 67% such as dodecyltrimethylammonium chloride or ethyld- Evaluation of Compounds as Bleach Activate lmethyloctadecylammontum methosulfate.
Exam 1 S Suitabl t ical m hoteri d t r ts The compounds of Examples l-3, plus additional p e o y yp a p c e e gen compounds (Examples 4-6) were evaluated as activaare those detergent compounds possessing both cattonic and anionic sites and include, for example, amino l tors applied wlth and detergemf In fan acids such as dimeth lamino r0 ionic acid and the tests, the mole ratio of activator used to sodium 3 Y P P perborate was l:l.1. tmlnodifatty actds such as methyltmmodllaurtc acid.
The test procedure was as follows: Five-gram Examples of typical noniontc detergents inclu d swatches of desized, 80 X 80 cotton fabric are stained polyglycolethers ofalkanolamides ofhigher fatty acids 5 with tea in the following maImeL Five tea bags are and aiscf poiygiycoi ethers of higher aikanois and higher I placed in one liter of water and boiled for five minutes. fatty acids' The swatches are then immersed in the tea and the boil- Bieaching compositions y gonei'aiiy be used aiso ing is continued for another five minutes. The swatches for their germicidal properties in various applications are then removed from the tea wrung out dried at for oomli'oi of microbial growtii- Applications y be 200-2l5F., rinsed in cold water and again dried. made to any surface or substrate where such control is T f h i d cotton Swatches e l d i a desiredstainless steel Terg-O-Tometer, a test washing ma- The treatment of swimming pool water and swimchine, manufactured by U.S. Testing Company and ming pool surfaces with the compositions of the invenused in the detergent trade for evaluation purposes. tion is especially efficacious since the usually lower Forty grams of unstained cotton fabric and one liter of temperatures of these environments prevent effective distilled water at 120F. are then added so as to provide use ofother antimicrobial agents. A related utility is the a typical household washing machine water to cloth treatment of water supplies to render the same fit for ratio of about 20:1. There are then added 2.0 grams of human consumption or for industrial use, such as the Tide" (an anionic alkylaryl sulfonate type detergent), sanitization of field water for consumption by military 0.33 gram of anhydrous sodium perborate (or an equivpersonnel or the treatment of industrial process water alent of hydrated material) and the indicated amount so it can be reused in industrial processes or by the surof the activator compound. The Terg-O-Tometer is oprounding community. The compositions also may be erated at 100 cycles per minute for fifteen minutes at employed in admixture with detergents for use as home a temperature of 120F. The swatches are then reor industrial germicidal detergents, or in hair bleaching moved, rinsed with cold water, and dried at room temcompositions containing peroxygen compounds. perature.
The following examples and tests will serve to further Reflectance readings On the w che are aken both ill h i i before and after laundering using a Hunter Model 25-M Reflectometer with a blue filter. The swatches EXAMPLES are backed with a white procelain plate and read once on each side. Fluorescent effect is excluded from all Preparation of Pyridinium Compounds readings- The reflectance readings are averaged and the percent stain removal is obtained in accordance with the following formula in which R is the symbol for Reflec- Total R (bleached) minus R (stained) v Cl stain removal R (unstained) minus R (stained) 100 Control runs are also made for each set or series of R2 evaluation tests using detergent and sodium perborate with no activator. The percent stain removed may vary To a solution of the respective di-functional monosomewhat on the Control due to variations in the cloth chloro triazine in 100 ml. ethyl acetate is added a molar and the tea used to produce the stains. equivalent of pyridine (using a slight excess). The solid The test results obtained are shown in Table l where product forms almost immediately. The slurry is stirred the activator compounds are identified by the A, R for 4 hours, filtered and dried. No recrystallization is and R radicals thereof in the general formula shown at necessary. the top of the Table.
Table l R Wt. of Ex. 2 Stain Removed Activator Stain No. A R, R (Control) (g.) Removed l N(CH CN) N(CH CN) 35.9 1.10 44.9
TABLE I Continued RI-KNTEA Y Wt. of
Ex. Stain Removed Activator Stain No. A R R; (Control) (g.) Removed 2 -N OCH OCH;, 38.2 0.78 44.2
l 3 N OCH;, -N(CH CN) 42.5 0.96 50.5
"Prepared according to J. Org. Chem. 22. 444 (I957) Prepared according to 1.08. 1967. C. 466.
We claim: 3. A composition according to claim 1 wherein the l. A bleaching composition Comprising hydrogen hydrogen peroxide-releasing compound is sodium perperoxide or a hydrogen peroxide-releasing compound b r t or di -b r and an activating amount ofa ring halogen-free triazine 4. A composition according to claim 1 wherein A in compound represented by the formula: the ring halogen-free triazine compound is a pyridinium radical.
5. A composition according to claim 4 wherein the R --A ring-halogen-free triazine compound is represented by I the formula H,CO I-- where A is a radical selected from the group consisting N N Y C19 of pyridinium, dialkoxyphosphinyl, mercapto, (dialkylthiocarbamoy1)thio, alkyl sulfonyl, trihalomethyl and sulfophenoxy radicals; and R and R are individually selected from the group consisting of hydroxy, mercapto, alkyl, alkenyl, alkoxy, alkylmercapto, aryl, aryloxy, arylmercapto, dialkoxyphosphinyl and 6. A composition according to claim 4 wherein the ring halogen-free triazine compound is represented by the formula where R, and R are individually selected from the group consisting of hydrogen, alkyl, cyanoalkyl, hy- N 69 I droxyalkyl, carboxyalkyl, chloroalkyl, alkoxyalkyl, (NCCHZ)2N I/ \F sulfoalkyl, aryl, sulfoaryl, acylaminoalkyl and carbal moylalkyl, and where R and R taken together are 0 N N joined to complete a heterocyclic ring selected from V the group consisting of morpholine, piperazine and Cle piperidine rings. N(CHCN 2. A composition according to claim 1 wherein the mole ratio of the ring halogen-free triazine compound 7, A composition di to l i 4 h i h to the hydrogen peroxide-releasing compound is from ring halogen-free triazine compound is represented by about 1:1 to about 1:10. the formula 9 N aCO- I HS- -SH I N N N V CH NU-UC H 8, A composition according to claim 1 wherein the 10. A composition according to claim 1 wherein the ring halogen-free triazine compound is represented by ""8 halogen-free mazme compound represented y the formula the formula 3 if N CH3O), |4 (OCHQ, 4 I -0- so n I NV" N N O=P(OCH so,H.
9. A composition according to claim 1 wherein the ring halogen-free triazine compound is represented by th? formula

Claims (10)

1. A BLEACHING COMPOSITION COMPRISING HYDROGEN PEROXIDE OR A HYDROGEN PEROXIDE-RELEASING COMPOUND AND AN ACTIVATING AMOUNT OF A RING HALOGEN-FREE TRAZINE COMPOUND REPRESENTED BY THE FORMULA:
2. A composition according to claim 1 wherein the mole ratio of the ring halogen-free triazine 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 1 wherein A in the ring halogen-free triazine compound is a pyridinium radical.
5. A composition according to claim 4 wherein the ring-halogen-free triazine compound is represented by the formula
6. A composition according to claim 4 wherein the ring halogen-free triazine compound is represented by the formula
7. A composition according to claim 4 wherein the ring halogen-free triazine compound is represented by the formula
8. A composition according to claim 1 wherein the ring halogen-free triazine compound is represented by the formula
9. A composition according to claim 1 wherein the ring halogen-free triazine compound is represented by the formula
10. A composition according to claim 1 wherein the ring halogen-free triazine compound is represented by the formula
US343575A 1973-03-21 1973-03-21 Ring halogen-free substituted triazine compounds as bleach activators Expired - Lifetime US3912648A (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
US343575A US3912648A (en) 1973-03-21 1973-03-21 Ring halogen-free substituted triazine compounds as bleach activators
CA192,311A CA1024702A (en) 1973-03-21 1974-02-12 Ring-halogen-free substituted triazines as bleach activators
GB687074A GB1428926A (en) 1973-03-21 1974-02-14 Ring-halogen-free substituted triazines as bleach activators
AU65720/74A AU474817B2 (en) 1973-03-21 1974-02-18 Ring-halogen-free substituted triazines as bleach activators
AR252501A AR203190A1 (en) 1973-03-21 1974-02-22 WHITENING COMPOSITION
IT49215/74A IT1004368B (en) 1973-03-21 1974-03-08 BLEACH COMPOSITION
NL7403435A NL7403435A (en) 1973-03-21 1974-03-14
JP49029285A JPS49126581A (en) 1973-03-21 1974-03-15
DE2412953A DE2412953A1 (en) 1973-03-21 1974-03-18 ON THE RING HALOGEN-FREE SUBSTITUTED TRIAZINES AS BLEACH ACTIVATORS
BE142218A BE812564A (en) 1973-03-21 1974-03-20 SUBSTITUTED TRIAZINES CONTAINING NO HALOGEN ON THE CYCLE
FR7409572A FR2222430B1 (en) 1973-03-21 1974-03-20
BR2200/74A BR7402200D0 (en) 1973-03-21 1974-03-21 PERFECTED WHITE COMPOSITION
DD177356A DD111422A5 (en) 1973-03-21 1974-03-21

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JP (1) JPS49126581A (en)
AR (1) AR203190A1 (en)
AU (1) AU474817B2 (en)
BE (1) BE812564A (en)
BR (1) BR7402200D0 (en)
CA (1) CA1024702A (en)
DD (1) DD111422A5 (en)
DE (1) DE2412953A1 (en)
FR (1) FR2222430B1 (en)
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NL (1) NL7403435A (en)

Cited By (9)

* Cited by examiner, † Cited by third party
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US3986971A (en) * 1975-11-25 1976-10-19 American Cyanamid Company 2,4-diisocyanato-6-halo-s-triazines as peroxygen bleach activators
US4111651A (en) * 1977-10-03 1978-09-05 Fmc Corporation Sulfonic anhydrides in peroxygen bleaching
US4202786A (en) * 1978-12-22 1980-05-13 Fmc Corporation Peroxygen bleaching and compositions therefor
US4207070A (en) * 1978-10-10 1980-06-10 Fmc Corporation Peroxygen bleaching and compositions therefor
US4212757A (en) * 1978-12-22 1980-07-15 Fmc Corporation Peroxygen bleaching and compositions therefor
US4215003A (en) * 1978-11-20 1980-07-29 Fmc Corporation Peroxygen bleaching and compositions therefor
WO2005105303A1 (en) * 2004-04-29 2005-11-10 Ciba Specialty Chemicals Holding Inc. Use of metal complexes having bispyridylpyrimidine or bispyridyltriazine ligands as catalysts for reactions with peroxy compounds for bleaching coloured stains on hard surfaces
WO2005068074A3 (en) * 2004-01-12 2006-05-18 Ciba Sc Holding Ag Use of metal complex compounds comprising pyridine pryimidine or s-triazne derived ligands as catalysts for oxidations with organic peroxy acids and/or precursors of organic peroxy acid and h2o2
WO2007090461A1 (en) * 2006-02-06 2007-08-16 Ciba Holding Inc. Use of metal complex compounds as oxidation catalysts

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JP6668091B2 (en) * 2016-01-29 2020-03-18 ミヨシ油脂株式会社 UV absorber and resin member using the same

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US3055897A (en) * 1959-08-08 1962-09-25 Therachemie Chem Therapeut Process for the production of triazineperhydrate compounds
US3336228A (en) * 1955-05-09 1967-08-15 Fmc Corp Active chlorine compositions containing dichlorocyanuric acid and salts thereof
US3422020A (en) * 1965-02-11 1969-01-14 Henkel & Cie Gmbh Low-sudsing detergent compositions
US3775332A (en) * 1970-07-31 1973-11-27 Henkel & Cie Gmbh Method of activating per-compounds and solid activated per-compound compositions

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US3336228A (en) * 1955-05-09 1967-08-15 Fmc Corp Active chlorine compositions containing dichlorocyanuric acid and salts thereof
US2913460A (en) * 1956-09-10 1959-11-17 Procter & Gamble Composition having bleaching, sterilizing and disinfecting properties, and method of preparation thereof
US3055897A (en) * 1959-08-08 1962-09-25 Therachemie Chem Therapeut Process for the production of triazineperhydrate compounds
US3422020A (en) * 1965-02-11 1969-01-14 Henkel & Cie Gmbh Low-sudsing detergent compositions
US3775332A (en) * 1970-07-31 1973-11-27 Henkel & Cie Gmbh Method of activating per-compounds and solid activated per-compound compositions

Cited By (11)

* 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
US4111651A (en) * 1977-10-03 1978-09-05 Fmc Corporation Sulfonic anhydrides in peroxygen bleaching
US4207070A (en) * 1978-10-10 1980-06-10 Fmc Corporation Peroxygen bleaching and compositions therefor
US4215003A (en) * 1978-11-20 1980-07-29 Fmc Corporation Peroxygen bleaching and compositions therefor
US4202786A (en) * 1978-12-22 1980-05-13 Fmc Corporation Peroxygen bleaching and compositions therefor
US4212757A (en) * 1978-12-22 1980-07-15 Fmc Corporation Peroxygen bleaching and compositions therefor
WO2005068074A3 (en) * 2004-01-12 2006-05-18 Ciba Sc Holding Ag Use of metal complex compounds comprising pyridine pryimidine or s-triazne derived ligands as catalysts for oxidations with organic peroxy acids and/or precursors of organic peroxy acid and h2o2
US20090189119A1 (en) * 2004-01-12 2009-07-30 Torsten Wieprecht Use of metal complex compounds comprising pyridine pyrimidine or s-triazine derived ligands as catalysts for oxidations with organic peroxy acids and/or precursors of organic peroxy acids and h202
WO2005105303A1 (en) * 2004-04-29 2005-11-10 Ciba Specialty Chemicals Holding Inc. Use of metal complexes having bispyridylpyrimidine or bispyridyltriazine ligands as catalysts for reactions with peroxy compounds for bleaching coloured stains on hard surfaces
US20080000032A1 (en) * 2004-04-29 2008-01-03 Torsten Wieprecht Use of Metal Complexes Having Bispyridylpyrimidine or Bispyridyltriazine Ligands as Catalysts for Reactions With Peroxy Compounds for Bleaching Coloured Stains on Hard Surfaces
WO2007090461A1 (en) * 2006-02-06 2007-08-16 Ciba Holding Inc. Use of metal complex compounds as oxidation catalysts

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CA1024702A (en) 1978-01-24
DD111422A5 (en) 1975-02-12
BE812564A (en) 1974-09-20
IT1004368B (en) 1976-07-10
AU474817B2 (en) 1976-08-05
AR203190A1 (en) 1975-08-22
BR7402200D0 (en) 1974-11-05
NL7403435A (en) 1974-09-24
DE2412953A1 (en) 1974-09-26
JPS49126581A (en) 1974-12-04
AU6572074A (en) 1975-08-21
GB1428926A (en) 1976-03-24
FR2222430B1 (en) 1977-10-07
FR2222430A1 (en) 1974-10-18

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