US3907698A - Bridged halotriazine compounds as bleach activators - Google Patents

Bridged halotriazine compounds as bleach activators Download PDF

Info

Publication number: US3907698A
Authority: US; United States
Prior art keywords: bridged; compound; halotriazine; compounds; composition according
Prior art date: 1973-03-21
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

Other languages

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.)

1973-03-21

Filing date

1973-03-21

Publication date

1975-09-23

1973-03-21 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1973-03-21 Priority to US343576A priority Critical patent/US3907698A/en

1974-02-18 Priority to AU65718/74A priority patent/AU6571874A/en

1974-02-22 Priority to AR252502A priority patent/AR203840A1/es

1974-03-08 Priority to IT49216/74A priority patent/IT1004369B/it

1974-03-11 Priority to NL7403230A priority patent/NL7403230A/xx

1974-03-18 Priority to DE2412952A priority patent/DE2412952A1/de

1974-03-19 Priority to BR742144A priority patent/BR7402144D0/pt

1974-03-19 Priority to JP49030658A priority patent/JPS49127881A/ja

1974-03-20 Priority to BE142219A priority patent/BE812565A/fr

1974-03-20 Priority to FR7409573A priority patent/FR2222431B1/fr

1974-03-21 Priority to DD177355A priority patent/DD111421A5/xx

1975-09-23 Application granted granted Critical

1975-09-23 Publication of US3907698A publication Critical patent/US3907698A/en

1992-09-23 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 34
239000012190 activator Substances 0.000 title abstract description 16
239000007844 bleaching agent Substances 0.000 title abstract description 13
239000000203 mixture Substances 0.000 claims abstract description 30
-1 vinylene, phenylene, biphenylene Chemical group 0.000 claims abstract description 14
238000004061 bleaching Methods 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 20
239000003599 detergent Substances 0.000 claims description 18
229960001922 sodium perborate Drugs 0.000 claims description 7
YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 claims description 7
230000003213 activating effect Effects 0.000 claims description 3
VTIIJXUACCWYHX-UHFFFAOYSA-L disodium;carboxylatooxy carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OOC([O-])=O VTIIJXUACCWYHX-UHFFFAOYSA-L 0.000 claims description 3
229940045872 sodium percarbonate Drugs 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract description 6
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract description 6
125000000217 alkyl group Chemical group 0.000 abstract description 5
125000003118 aryl group Chemical group 0.000 abstract description 5
150000002431 hydrogen Chemical class 0.000 abstract description 5
239000000460 chlorine Substances 0.000 abstract description 4
125000004183 alkoxy alkyl group Chemical group 0.000 abstract description 3
125000005242 carbamoyl alkyl group Chemical group 0.000 abstract description 3
125000004181 carboxyalkyl group Chemical group 0.000 abstract description 3
125000004966 cyanoalkyl group Chemical group 0.000 abstract description 3
125000000623 heterocyclic group Chemical group 0.000 abstract description 3
125000003386 piperidinyl group Chemical group 0.000 abstract description 3
125000004964 sulfoalkyl group Chemical group 0.000 abstract description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 2
125000003342 alkenyl group Chemical group 0.000 abstract description 2
125000003545 alkoxy group Chemical group 0.000 abstract description 2
125000004414 alkyl thio group Chemical group 0.000 abstract description 2
125000004104 aryloxy group Chemical group 0.000 abstract description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 2
229910052794 bromium Inorganic materials 0.000 abstract description 2
229910052801 chlorine Inorganic materials 0.000 abstract description 2
125000004965 chloroalkyl group Chemical group 0.000 abstract description 2
229910052731 fluorine Inorganic materials 0.000 abstract description 2
239000011737 fluorine Substances 0.000 abstract description 2
229910052736 halogen Inorganic materials 0.000 abstract description 2
150000002367 halogens Chemical class 0.000 abstract description 2
125000002768 hydroxyalkyl group Chemical group 0.000 abstract description 2
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
244000269722 Thea sinensis Species 0.000 description 6
238000012360 testing method Methods 0.000 description 6
239000004744 fabric Substances 0.000 description 5
235000014113 dietary fatty acids Nutrition 0.000 description 4
238000011156 evaluation Methods 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
150000002978 peroxides Chemical class 0.000 description 4
229920000742 Cotton Polymers 0.000 description 3
125000002091 cationic group Chemical group 0.000 description 3
230000002070 germicidal effect Effects 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
125000000129 anionic group Chemical group 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
235000013305 food Nutrition 0.000 description 2
238000004900 laundering Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000000758 substrate Substances 0.000 description 2
230000009182 swimming Effects 0.000 description 2
238000005406 washing Methods 0.000 description 2
QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
ZPYXMGLVTMUGJV-UHFFFAOYSA-N 12-[11-carboxyundecyl(methyl)amino]dodecanoic acid Chemical compound OC(=O)CCCCCCCCCCCN(C)CCCCCCCCCCCC(O)=O ZPYXMGLVTMUGJV-UHFFFAOYSA-N 0.000 description 1
QCYOIFVBYZNUNW-UHFFFAOYSA-N 2-(dimethylazaniumyl)propanoate Chemical compound CN(C)C(C)C(O)=O QCYOIFVBYZNUNW-UHFFFAOYSA-N 0.000 description 1
WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
241001387976 Pera Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
WUUOYCPDGWDPRO-UHFFFAOYSA-N ethyl-dimethyl-octadecylazanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CC WUUOYCPDGWDPRO-UHFFFAOYSA-N 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000002304 perfume Substances 0.000 description 1
125000005342 perphosphate group Chemical group 0.000 description 1
JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
238000011012 sanitization Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
239000004753 textile Substances 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
210000002700 urine Anatomy 0.000 description 1

Classifications

- 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)
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 (fr)	1973-03-21	1974-03-11
DE2412952A DE2412952A1 (de)	1973-03-21	1974-03-18	Gekoppelte halogentriazine als bleichaktivatoren
BR742144A BR7402144D0 (pt)	1973-03-21	1974-03-19	Composicao alvejante ativada aperfeicoada
JP49030658A JPS49127881A (fr)	1973-03-21	1974-03-19
BE142219A BE812565A (fr)	1973-03-21	1974-03-20	Compositions de blanchiment contenant des triazines halogenees pontees comme activateurs de blanchiment
FR7409573A FR2222431B1 (fr)	1973-03-21	1974-03-20
DD177355A DD111421A5 (fr)	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

Family

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 (fr)
JP (1)	JPS49127881A (fr)
AR (1)	AR203840A1 (fr)
AU (1)	AU6571874A (fr)
BE (1)	BE812565A (fr)
BR (1)	BR7402144D0 (fr)
DD (1)	DD111421A5 (fr)
DE (1)	DE2412952A1 (fr)
FR (1)	FR2222431B1 (fr)
IT (1)	IT1004369B (fr)
NL (1)	NL7403230A (fr)

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

1973
- 1973-03-21 US US343576A patent/US3907698A/en not_active Expired - Lifetime
1974
- 1974-02-18 AU AU65718/74A patent/AU6571874A/en not_active Expired
- 1974-02-22 AR AR252502A patent/AR203840A1/es active
- 1974-03-08 IT IT49216/74A patent/IT1004369B/it active
- 1974-03-11 NL NL7403230A patent/NL7403230A/xx unknown
- 1974-03-18 DE DE2412952A patent/DE2412952A1/de active Pending
- 1974-03-19 JP JP49030658A patent/JPS49127881A/ja active Pending
- 1974-03-19 BR BR742144A patent/BR7402144D0/pt unknown
- 1974-03-20 BE BE142219A patent/BE812565A/fr unknown
- 1974-03-20 FR FR7409573A patent/FR2222431B1/fr not_active Expired
- 1974-03-21 DD DD177355A patent/DD111421A5/xx unknown

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

Publication	Publication Date	Title
US3986972A (en)	1976-10-19	Acyl nitrile compounds as peroxygen bleach activators
US5143641A (en)	1992-09-01	Ester perhydrolysis by preconcentration of ingredients
CA1069259A (fr)	1980-01-08	Decolorant, et methode de decoloration
EP0290081B1 (fr)	1990-10-31	Composition détergente et blanchiment amélioré pour le nettoyage de tissus
US6139769A (en)	2000-10-31	Bleaching-active metal complexes
US4199466A (en)	1980-04-22	Activated bleaching process and compositions therefor
US3775333A (en)	1973-11-27	N-acyl azolinones as peroxygen bleach activators
US3882035A (en)	1975-05-06	Iminodiacetonitrile derivatives as peroxygen bleach activators
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