GB855735A - Bleaching processes and compositions - Google Patents

Bleaching processes and compositions

Info

Publication number
GB855735A
GB855735A GB14921/58A GB1492158A GB855735A GB 855735 A GB855735 A GB 855735A GB 14921/58 A GB14921/58 A GB 14921/58A GB 1492158 A GB1492158 A GB 1492158A GB 855735 A GB855735 A GB 855735A
Authority
GB
United Kingdom
Prior art keywords
acyl
diacetyl
sodium
organoamide
rco
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
Application number
GB14921/58A
Inventor
Samuel Claude Bright
Francis Robert Maxwe Mcdonnell
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.)
Unilever PLC
Original Assignee
Unilever PLC
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 Unilever PLC filed Critical Unilever PLC
Priority to GB14921/58A priority Critical patent/GB855735A/en
Priority to FR794156A priority patent/FR1232554A/en
Priority to DEU6184A priority patent/DE1291317B/en
Publication of GB855735A publication Critical patent/GB855735A/en
Priority to US336068A priority patent/US3177148A/en
Expired legal-status Critical Current

Links

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
    • 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
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06LDRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/10Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen
    • D06L4/12Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen combined with specific additives

Landscapes

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

Abstract

N : N-diacetyl-p-chloroaniline is prepared by reacting p-chloroaniline with acetic anhydride in the presence of sodium acetate. N : N-dibutyrylaniline is prepared by reacting butyric acid with aniline in xylene solution to produce monobutyryl-aniline, which is then further reacted with butyric anhydride to produce N : N-dibutyrylaniline. N : N1-diacetylbarbitone is prepared by passing ketene into a solution of barbitone in ethylacetate containing a little concentrated sulphuric acid.ALSO:Textile materials are bleached with an aqueous solution of hydrogen peroxide and a "reactive" acyl organoamide, i.e. anacyl organoamide which, in the test described below, gives a titre of at least 1,5 ml. of 0,1 N sodium thiosulphate. The test is carried out by dissolving 2,5 g. of sodium pyrophosphate, 0,615g. of sodium perborate and 0,5g. of sodium dodecyl benzene sulphonate in 1000ml. of distilled water at 60 DEG C., adding an amount of amide such that, for each atom of available oxygen present, one molecule of amide is introduced, stirring vigorously at 60 DEG C. and, after 5 minutes, pipetting a 100 ml. portion of the solution on to 250 g. of cracked ice and 15 ml. of glacial acetic acid, adding 0.4g. of potassium iodide and titrating the liberated iodine with 0,1N sodium thiosulphate using starch as indicator. An "acyl organoamide" is defined as a compound of the formula: RCONR1R2 in which RCO is derived from an organic carboxylic acid, R1 is an acyl radical and R2 is any suitable radical as determined by the test described, e.g. alkyl, aryl, carboxylic acyl or sulphonic acyl. RCO is preferably an aliphatic radical containing 2-4 carbon atoms and any two of the radicals RCO, R1 and R2 can be linked together to form a divalent radical which, with the nitrogen, constitutes a heterocyclic ring, as in the N-acyl lactams and N-acyl anthranils. Suitable acyl organoamides are N : N- diacetylaniline, N : N-diacetyl -ptoluidine, N : N-diacetyl -pchloroaniline, N : N- dibutyrylaniline, dibenzanilide, N- acetylcaprolactam, N : N1- diacetyl-barbitone, N- acetylphthalimide, N-acetylsaccharin, N- acetyl anthranil and N : N- diacetyl -5 : 5- dimethyl hydantoin. The hydrogen peroxide may be added directly to the bleaching bath but it is preferably liberated from an inorganic persalt, e.g. an alkali metal perborate, percarbonate, perpyrophosphate or persilicate. Compositions comprising an inorganic persalt and a reactive acyl organoamide may be prepared, the compositions preferably containing 1/4 -4 molecules of reactive amide for each atom of available oxygen in the persalt. The compositions may also contain sufficient of an alkali-metal carbonate, silicate or phosphate, e.g. an orthophosphate, tripolyphosphate or pyrophosphate, to give the solution a pH of 8-11, and 10-50% of an organic detergent, which may be a soap or a soapless detergent, e.g. an alkylaryl sulphonate or alkylsulphate, together with conventional detergent adjuncts, e.g. alkali-metal sulphates, sodium carboxymethylcellulose and fluorescent brightening agents. Examples describe the bleaching of cotton fabrics. The Provisional Specification refers to the use of acylorganoamides in which R1 is an organic group linked by carbon direct to the nitrogen atom.ALSO:A detergent composition comprises an inorganic persalt and a "reactive" acyl organoamide, i.e. an acyl organoamide which fulfils the requirements of a test which is described, and which is defined as a compound of the formula RCONR1R2 in which RCO is derived from an organic carboxylic acid, R1 is an acyl radical and R2 is any suitable radical as determined by the test described, e.g. alkyl, aryl, carboxylic acyl or sulphonic acyl. RCO is preferably an aliphatic radical containing 2-4 carbon atoms and any two of the radicals RCO, R1 and R2 can be linked together to form a divalent radical which, with the nitrogen, constitutes a heterocyclic ring, as in the N-acyllactams and N-acylanthranils. Suitable acyl organoamides are N:N-diacetyl aniline, N:N - diacetyl - p - toluidine, N:N - diacetyl - p-chloroaniline, N:N-dibutyrylaniline, dibenzanilide, N-acetylcaprolactam, N:N1-diacetylbarbitane, N-acetylphthalimide, N-acetylsaccharin, N-acetylanthranil and N:N-diacetyl-5:5-dimethyl hydantoin. Specified persalts are alkali metal perborates, percarbanates, perpyrophosphates and persilicates, the compositions preferably containing 1/4 -4 molecules of reactive amide for each atom of available oxygen in the persalt. The detergent may be a soap or a soapless detergent, e.g. an alkyl aryl sulphanate or alkyl sulphate, and may be present to the extent of 10-50%. The composition may also contain alkali-metal sulphates, sodium carboxymethyl cellulose and fluorescent brightening agents, and sufficient of an alkali-metal carbonate, silicate, orthophosphate, tripolyphosphate or pyrophosphate, to give solutions of the composition a pH of 8-11. The Provisional Specification refers to the use of acyl organoamides in which R1 is an organic group linked by carbon direct to the nitrogen atom.
GB14921/58A 1958-05-09 1958-05-09 Bleaching processes and compositions Expired GB855735A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
GB14921/58A GB855735A (en) 1958-05-09 1958-05-09 Bleaching processes and compositions
FR794156A FR1232554A (en) 1958-05-09 1959-05-06 Bleaching processes and compositions
DEU6184A DE1291317B (en) 1958-05-09 1959-05-08 Process for bleaching textiles
US336068A US3177148A (en) 1958-05-09 1964-01-06 Bleaching processes and compositions

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB14921/58A GB855735A (en) 1958-05-09 1958-05-09 Bleaching processes and compositions

Publications (1)

Publication Number Publication Date
GB855735A true GB855735A (en) 1960-12-07

Family

ID=10049920

Family Applications (1)

Application Number Title Priority Date Filing Date
GB14921/58A Expired GB855735A (en) 1958-05-09 1958-05-09 Bleaching processes and compositions

Country Status (4)

Country Link
US (1) US3177148A (en)
DE (1) DE1291317B (en)
FR (1) FR1232554A (en)
GB (1) GB855735A (en)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3245913A (en) * 1964-09-15 1966-04-12 Monsanto Co Bleaching compositions containing acyl sulfonamides
US4422950A (en) 1980-12-09 1983-12-27 Lever Brothers Company Bleach activator granules and preparation thereof
US4786421A (en) * 1986-08-06 1988-11-22 Lever Brothers Company Fabric conditioning composition
US4892555A (en) * 1986-08-06 1990-01-09 Lever Brothers Company Method for conditioning fabrics
US5372740A (en) * 1993-09-03 1994-12-13 Lever Brothers Company, Division Of Conopco, Inc. Homogeneous liquid automatic dishwashing detergent composition based on sodium potassium tripolyphosphate
US5374369A (en) * 1993-10-14 1994-12-20 Lever Brothers Company, Division Of Conopco, Inc. Silver anti-tarnishing detergent composition
US5468410A (en) * 1993-10-14 1995-11-21 Angevaare; Petrus A. Purine class compounds in detergent compositions
US5480576A (en) * 1993-10-14 1996-01-02 Lever Brothers Company, Division Of Conopco, Inc. 1,3-N azole containing detergent compositions
EP0690122A2 (en) 1994-06-30 1996-01-03 The Procter & Gamble Company Detergent compositions
EP0693549A1 (en) 1994-07-19 1996-01-24 The Procter & Gamble Company Solid bleach activator compositions
EP0698661A2 (en) 1994-08-25 1996-02-28 Degussa Aktiengesellschaft Activators for inorganic peroxygen compounds and product containing them
US5584888A (en) * 1994-08-31 1996-12-17 Miracle; Gregory S. Perhydrolysis-selective bleach activators
EP0778339A2 (en) 1995-12-06 1997-06-11 Basf Corporation Improved non-phosphate machine dishwashing compositions containing polycarboxylate polymers and nonionic graft copolymers of vinyl acetate and polyalkylene oxide
EP0778340A2 (en) 1995-12-06 1997-06-11 Basf Corporation Improved non-phosphate machine dishwashing compositions containing copolymers of alkylene oxide adducts of allyl alcohol and acrylic acid
US5856282A (en) * 1994-12-22 1999-01-05 The Procter & Gamble Company Silicone compositions
US5985815A (en) * 1993-11-25 1999-11-16 Warwick International Group Limited Bleach activators
WO2011051681A1 (en) 2009-10-28 2011-05-05 Revolymer Limited Composite
WO2012140442A1 (en) 2011-04-15 2012-10-18 Revolymer Limited Particles with hydroxyl vinylic copolymer coating sensitive to ionic strength
EP3266762A1 (en) 2016-07-06 2018-01-10 3V SIGMA S.p.A Activators for peroxygenated compounds

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1297574B (en) * 1964-05-12 1969-06-19 Degussa Detergents and bleaches
CA783079A (en) * 1965-06-09 1968-04-16 Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler Agent for the bleaching and washing of textiles
FR1457677A (en) * 1965-09-23 1966-01-24 Colgate Palmolive Co Laundry washing process
GB1182143A (en) * 1966-03-01 1970-02-25 United States Borax Chem Bleaching Compositions and Methods.
DK128287A (en) * 1967-10-24
DE1802576A1 (en) * 1967-11-01 1969-08-07 Colgate Palmolive Co Bleach and detergent
US3715184A (en) * 1967-12-30 1973-02-06 Henkel & Cie Gmbh Method of activating per-compounds and solid activated per-compound compositions
GB1286459A (en) * 1968-12-12 1972-08-23 Unilever Ltd Detergent compositions
US3969257A (en) * 1971-07-23 1976-07-13 Colgate-Palmolive Company Washing and bleaching composition containing bleach, activator and a nitrilotricarboxylic acid compound
IT966940B (en) * 1972-12-05 1974-02-20 Unilever Nv DETERGENT COMPOSITION
US3886078A (en) * 1973-02-28 1975-05-27 American Cyanamid Co N-benzoylsaccharin as peroxygen bleach activator
US4300897A (en) * 1973-08-24 1981-11-17 Colgate-Palmolive Company Method for bleaching with peroxymonosulfate-based compositions
US4123376A (en) * 1973-08-24 1978-10-31 Colgate-Palmolive Company Peroxymonosulfate-base bleaching and bleaching detergent compositions
FI64639C (en) * 1978-09-27 1983-12-12 Unilever Nv BLEKNINGS- OCH RENGOERINGSKOMPOSITION
US4397757A (en) * 1979-11-16 1983-08-09 Lever Brothers Company Bleaching compositions having quarternary ammonium activators
DE3128336A1 (en) * 1981-07-17 1983-01-27 Henkel KGaA, 4000 Düsseldorf "METHOD FOR PRODUCING COATED NUCLEAR BLEACHING ACTIVATORS"
DE3304848A1 (en) * 1983-02-12 1984-08-16 Henkel KGaA, 4000 Düsseldorf ORGANIC CYANAMIDE COMPOUNDS AS ACTIVATORS FOR INORGANIC PER CONNECTIONS
CN1065563C (en) * 1993-05-20 2001-05-09 普罗格特-甘布尔公司 Bleaching compounds comprising N-acyl caprolactam for use in hand-wash or other low-water cleaning systems
ES2119204T3 (en) 1993-05-20 1998-10-01 Procter & Gamble BLEACHING COMPOUNDS INCLUDING REPLACED BENZOIL-CAPROLACTAMA BLEACHING ACTIVATORS.
US5998350A (en) * 1993-05-20 1999-12-07 The Procter & Gamble Company Bleaching compounds comprising N-acyl caprolactam and/or peroxy acid activators
US5405412A (en) * 1994-04-13 1995-04-11 The Procter & Gamble Company Bleaching compounds comprising N-acyl caprolactam and alkanoyloxybenzene sulfonate bleach activators
US5753138A (en) * 1993-06-24 1998-05-19 The Procter & Gamble Company Bleaching detergent compositions comprising bleach activators effective at low perhydroxyl concentrations
US5405413A (en) * 1993-06-24 1995-04-11 The Procter & Gamble Co. Bleaching compounds comprising acyl valerolactam bleach activators
US5635104A (en) 1993-06-24 1997-06-03 The Procter & Gamble Company Bleaching solutions and method utilizing selected bleach activators effective at low perhydroxyl concentrations
DE4412390A1 (en) * 1994-04-11 1995-10-19 Hoechst Ag Process for bleaching textiles
US5635103A (en) 1995-01-20 1997-06-03 The Procter & Gamble Company Bleaching compositions and additives comprising bleach activators having alpha-modified lactam leaving-groups
DE19530786A1 (en) 1995-08-22 1997-02-27 Hoechst Ag A bleaching composition containing polyoxometalates as a bleach catalyst
US5879409A (en) * 1996-02-23 1999-03-09 The Procter & Gamble Company Bleach additive and bleaching compositions having glycine anhydride activators
WO1998016610A2 (en) * 1996-10-15 1998-04-23 The Procter & Gamble Company Asymmetrical imide bleach activators and compositions employing the same

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US825883A (en) * 1905-07-10 1906-07-10 Walter Heinrici Stable solution of peroxid of hydrogen.
GB190516151A (en) * 1905-08-08 1906-01-04 Walter Heinrici A Process for Preparing a Stable Solution of Hydrogen Peroxide.
US2091186A (en) * 1935-01-11 1937-08-24 Du Pont Stabilization of bleach baths
US2576205A (en) * 1945-08-25 1951-11-27 Colgate Palmolive Peet Co Denture cleansing composition
DE1010048B (en) * 1953-05-20 1957-06-13 Degussa Process for washing fibrous materials or textile goods
US2809937A (en) * 1954-02-26 1957-10-15 Colgate Palmolive Co Germicidal detergent composition
GB782898A (en) * 1954-05-19 1957-09-18 Unilever Ltd Improvements in detergent compositions
BE549817A (en) * 1955-07-27
US2891912A (en) * 1956-06-21 1959-06-23 Gillette Co Opalescent detergent composition
AT187509B (en) * 1956-09-28 1956-10-25 Degussa Process for the treatment of polyamide fibers with peroxide-containing bleaches or detergents
US3061550A (en) * 1959-05-11 1962-10-30 Du Pont Textile bleaching composition

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3245913A (en) * 1964-09-15 1966-04-12 Monsanto Co Bleaching compositions containing acyl sulfonamides
US4422950A (en) 1980-12-09 1983-12-27 Lever Brothers Company Bleach activator granules and preparation thereof
US4786421A (en) * 1986-08-06 1988-11-22 Lever Brothers Company Fabric conditioning composition
US4892555A (en) * 1986-08-06 1990-01-09 Lever Brothers Company Method for conditioning fabrics
US5372740A (en) * 1993-09-03 1994-12-13 Lever Brothers Company, Division Of Conopco, Inc. Homogeneous liquid automatic dishwashing detergent composition based on sodium potassium tripolyphosphate
US5374369A (en) * 1993-10-14 1994-12-20 Lever Brothers Company, Division Of Conopco, Inc. Silver anti-tarnishing detergent composition
US5468410A (en) * 1993-10-14 1995-11-21 Angevaare; Petrus A. Purine class compounds in detergent compositions
US5480576A (en) * 1993-10-14 1996-01-02 Lever Brothers Company, Division Of Conopco, Inc. 1,3-N azole containing detergent compositions
US5985815A (en) * 1993-11-25 1999-11-16 Warwick International Group Limited Bleach activators
EP0690122A2 (en) 1994-06-30 1996-01-03 The Procter & Gamble Company Detergent compositions
EP0693549A1 (en) 1994-07-19 1996-01-24 The Procter & Gamble Company Solid bleach activator compositions
EP0698661A2 (en) 1994-08-25 1996-02-28 Degussa Aktiengesellschaft Activators for inorganic peroxygen compounds and product containing them
US5654269A (en) * 1994-08-25 1997-08-05 Degussa Aktiengesellschaft Activators for inorganic peroxo compounds and agents containing them
US5584888A (en) * 1994-08-31 1996-12-17 Miracle; Gregory S. Perhydrolysis-selective bleach activators
US5856282A (en) * 1994-12-22 1999-01-05 The Procter & Gamble Company Silicone compositions
EP0778339A2 (en) 1995-12-06 1997-06-11 Basf Corporation Improved non-phosphate machine dishwashing compositions containing polycarboxylate polymers and nonionic graft copolymers of vinyl acetate and polyalkylene oxide
EP0778340A2 (en) 1995-12-06 1997-06-11 Basf Corporation Improved non-phosphate machine dishwashing compositions containing copolymers of alkylene oxide adducts of allyl alcohol and acrylic acid
WO2011051681A1 (en) 2009-10-28 2011-05-05 Revolymer Limited Composite
WO2012140442A1 (en) 2011-04-15 2012-10-18 Revolymer Limited Particles with hydroxyl vinylic copolymer coating sensitive to ionic strength
EP3266762A1 (en) 2016-07-06 2018-01-10 3V SIGMA S.p.A Activators for peroxygenated compounds

Also Published As

Publication number Publication date
FR1232554A (en) 1960-10-10
US3177148A (en) 1965-04-06
DE1291317B (en) 1969-03-27

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