US3075921A - Substituted peroxybenzoic acid bleaching agents - Google Patents

Substituted peroxybenzoic acid bleaching agents Download PDF

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Publication number
US3075921A
US3075921A US6379A US637960A US3075921A US 3075921 A US3075921 A US 3075921A US 6379 A US6379 A US 6379A US 637960 A US637960 A US 637960A US 3075921 A US3075921 A US 3075921A
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Prior art keywords
peroxybenzoic acid
solid
substituted
bleaching agent
acid
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Expired - Lifetime
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US6379A
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English (en)
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Brocklehurst Peter
Pengilly Peter John
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Procter and Gamble Co
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Procter and Gamble Co
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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
    • C11D3/3945—Organic per-compounds
    • 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0039—Coated compositions or coated components in the compositions, (micro)capsules

Definitions

  • Peroxybenzoic acid has been known and used for a long time as an oxidizing agent in preparative and analytical chemistry. Unfortunately, peroxybenzoic acid possesses poor stability, decomposing at the approximate rate of 10% per week at room temperature even when maintained in an isolated state. Undoubtedly due largely to this drawback, it has not been found practicable to utilize peroxybenzoic acid as an industrial oxidizing agent, for example as an industrial bleaching agent. This is particularly unfortunate since peroxybenzoic acid is potentially an excellent bleaching agent and markedly superior to sodium perborate which is a bleaching agent normally used in household washing preparations. Thus peroxybenzoic acid in alkaline solution bleaches tea stained cloth in five minutes at 130 F. to an extent which is only to be achieved in ten minutes at the boil using alkaline hydrogen peroxide of equivalent available oxygen content.
  • a solid detergent composition comprising an active detergent ingredient and a peroxybenzoic acid which is substituted in the benzene nucleus by at least one group selected from nitro-, chloro-, cyano-, lower alkyland lower alkoxy-groups, the substitution being such that the substituted peroxybenzoic acid has a melting point not lower than 50 C.
  • Table I is illustrative of the melting points, stability and bleaching effects using various substituents.
  • the percentage colour removal obtained by sodium perborate used under the same conditions at the same available oxygen content in the bleach bath was 4%.
  • the available oxygen content is determined as follows:
  • 0.05 gm. of the peroxyacid is weighed into a 250 ml. conical flask and 10 ml. of dioxane is added.
  • 10 ml. glacial acetic acid When the pcroxyacid is completely dissolved 10 ml. glacial acetic acid and 10 ml. of 10% aqueous potassium iodide solution are added followed by 50 ml. distilled water.
  • the iodine is titrated with 0.025 N sodium thiosulphate solution using thyodene indicator near the end point.
  • the bleaching power of the peroxyacids is determined by adding sufficient of the peroxyacid to a 0.5% aqueous solution of a commercial heavy-duty synthetic detergent composition containing no other bleaching agent to give an available oxygen content of the solution of 50 parts per million.
  • the pH is adjusted to 9.0 by addition of caustic soda or sulphuric acid as necessary.
  • a 2-inch square of tea-stained cotton is agitated in this solution for 5 minutes at F. and is then rinsed and dried.
  • the reflectance of the cloth is measured by an EEL Reflectance Spectrophotometer.
  • the percentage colour removal is reflectance of bleached cloth minus reflectance of stained cloth divided by reflectance of desized cloth minus reflectance of stained cloth, and multiplied by 100.
  • a tea solution is prepared byboiling 28 gm. tea in 1 litre distilled water under reflux for one hour and then filtering the solution.
  • a piece of desized cotton cloth, 2 feet x 3 feet, is boiled in this filtered solution for one hour and is then rinsed with 3 cold distilled water until no more colour can be removed and finally dried.
  • Table I shows that the substituted peroxybenzoic acids with higher melting points have greater stability than those with lower melting points. It is clear that those compounds with melting points above 50 C. are sufficiently stable to be of value as bleaching agents in commercial solid detergent products while those with melting point below 50 C. are too unstable to be of value commercially.
  • peroxyacids are effective bleaching agents in the temperature range 100-175 F., they are eminently suitable for use in textile washing operations such as are carried out in domestic washing machines.
  • the detergent compositions of the invention may contain as active detergent ingredient, soap and/or synthetic detergents. Particularly suitable are anionic synthetic detergents such as alkyl benzene sulphonates,'alkyl sulphates, fatty acyl isethionates and fatty acyl taurides.
  • anionic synthetic detergents such as alkyl benzene sulphonates,'alkyl sulphates, fatty acyl isethionates and fatty acyl taurides.
  • the compositions may also contain the customary alkaline builder salts such as pyrophosphates, tripolyphosphates and the normal additives such as solid suspending agents (e.g.
  • Such detergent compositions for household washing purposes are generally alkaline, and the incorporation therein of the substituted peroxybenzoic acid is liable to impair the stability of the substituted peroxybenzoic acid. This can be largely overcome by pelletizi-ng the substituted peroxybenzoic acid alone or in admixture with an inorganic neutral or acid salt so as to give pellets of, say, A" diameter. This considerably reduces the relative area of contact between the substituted peroxybenzoic acid and the other ingredients of the washing composition and so renders the substituted peroxy-compound more immune against loss of stability. Moreover, the substituted peroxybenzoic acid may be protected from contact with the other ingredients of the mixture by coating it, preferably in pellet form, with an inert protective material which is removed by solution or melting when the Washing composition is used in normal washing operations.
  • an inert protective material which is removed by solution or melting when the Washing composition is used in normal washing operations.
  • a suitable protective material is parafiin wax of iodine value (I.V.) 10 or less, and melting point below about 120 F.
  • Table II below shows the-improvement of stability of 2,4-dichloroperoxybenzoic acid (DC PBA) in a heavy duty synthetic detergent composition which is achieved by pelletizing it, with or without subsequent coating, before mixing with the detergent powder.
  • the table shows the percentage decomposition of the DCPBA, as measured by loss of available oxygen, in detergent powder when stored for three months at 70 F. in a carton.
  • silicate content of the detergent powder was replaced by sodium sulphate.
  • the pellets contained by weight DCPBAand 50% by weight inorganic salt.
  • the weight ratio of wax i r to pellet was 0.25:1.
  • the wax used had I.V. l0 and melting point -1l0 F.
  • Peroxybenzoic acid itself may be prepared by reacting dibenzoyl peroxide with sodium methoxide under anhydrous conditions at low temperature (below 0 C.) followed by acidification according to the chemical equation:
  • the nuclear substituted peroxybenzoic acids are obtainable by the same procedure, using the appropriately substituted dibenzoyl peroxides.
  • Table III are given the starting materials and yields in thus preparing substituted peroxybenzoic acids.
  • the substituted dibenzoyl peroxides, used as starting materials, are obtainable from the appropriately substituted benzoyl chloride by the method of Swain, Stockmayer and Clarke (J. Amer. Chem. Soc. 72, 5426 1950)
  • the substituted peroxybenzoic acids may be purified by recrystallisation from chloroform or by sublimation.
  • the mother liquor was diluted with an equal volume of petroleum ether (boiling point 40-60" C.), cooled to -80C., filtered rapidly and the crystals dried in a vacuum desiccator to give a purity of 98.1%.
  • peroxyacids which can be purified by the same technique are 4-nitro-, 4-chloro and 4-methyl-peroxybenzoic acids.
  • a water-soluble detergent composition consisting essentially of a solid active anionic synthetic detergent ingredient which is present in sufficient amount to remove soil from textile materials, said solid active anionic synthetic detergent ingredient being selected from the group consisting of alkyl benzene sulphonates, alkyl sul phates, fatty acyl isethionates and fatty acyl taurides; and, a solid substituted peroxybenzoic acid bleaching agent which is present in suflicient amount to provide bleaching activity and is characterized by a stability to de composition in its solid state, said peroxybenzoic acid bleaching agent being substituted in the benzene nucleus by at least one radical selected from the group consisting of nitro, chloro, cyano, lower alkyl and lower alkoxy radicals, the substitution being such that the substituted peroxybenzoic acid bleaching agent has a melting point of at least 50 C.
  • a water-soluble detergent composition consisting essentially of a solid active anionic synthetic detergent ingredient which is present in sufiicient amount to remove soil from textile materials, said solid active anionic synthetic detergent ingredient being selected from the group consisting of alkyl benzene sulphonates, alkyl sulphates, fatty acyl isethionates and fatty acyl taurides; and, a solid substituted peroxybenzoic acid bleaching agent which is present in sufficient amount to provide bleaching activity and is characterized by a melting point of at least 50 C.
  • peroxybenzoic acid bleaching agent being selected from the group consisting of 2-chloro-, 3- chloro-, 4-chloro-, 2,4-dichloro-, 2-nitro-, 3-nitro-, 4-nitro-, 3-methyl-, 4-methyl-, 4-methoxy-, 4-tertiary butyl-, 4isopropyl-, 4-cyano-, and 2-chloro-4-nitroperoxybenzoic acids.
  • a water-soluble detergent composition consisting essentially of a solid active anionic synthetic detergent ingredient which is present in suflicient amount to remove soil from textile materials, said solid active anionic synthetic detergent ingredient being selected from the group consisting of alkyl benzene sulphonates, alkyl sulphates, fatty acyl isethionates and fatty acyl taurides; and, a solid substituted peroxybenzoic acid bleaching agent which is present in suflicient amount to provide bleaching activity and is characterized by a melting point of at least 50 C. and a stability to decomposition in its solid state, said peroxybenzoic acid bleaching agent being 2,4-dichloroperoxybenzoic acid.
  • an inorganic non-alkaline salt selected from the group consisting of ammonium sulphate, sodium sulphate, sodium hydrogen sulphate, and disodium dihydrogen pyrophosphate
  • a water-soluble detergent composition consisting essentially of (a) a detergent ingredient for removing soil from textile materials, said detergent ingredient consisting essentially of 23% by weight sodium dodecyl benzene sulphonate 39% by weight sodium tripolyphosphate 7% by weight silicate solids 1% by weight sodium carboxymethyl cellulose 19% by weight sodium sulfate 3% by weight coconut monoethanolamide 8% by weight water, and

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  • Chemical & Material Sciences (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)
  • Inorganic Chemistry (AREA)
  • Detergent Compositions (AREA)
US6379A 1959-02-11 1960-02-03 Substituted peroxybenzoic acid bleaching agents Expired - Lifetime US3075921A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB4843/59A GB886188A (en) 1959-02-11 1959-02-11 Detergent compositions
GB3356859 1959-10-02

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US (1) US3075921A (zh)
BE (1) BE587389A (zh)
CH (1) CH390442A (zh)
DE (1) DE1105092B (zh)
FR (1) FR1247242A (zh)
GB (1) GB886188A (zh)
NL (1) NL248201A (zh)

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3248336A (en) * 1964-04-06 1966-04-26 Fmc Corp Aqueous bleaching solutions of peroxycarboxylic acids
US3384596A (en) * 1965-12-30 1968-05-21 Dow Chemical Co Peroxy acid bleaching systems
US3988433A (en) * 1973-08-10 1976-10-26 The Procter & Gamble Company Oral compositions for preventing or removing stains from teeth
US4058131A (en) * 1974-09-16 1977-11-15 Colgate-Palmolive Company Improving hair body and manageability with diperisophthalic acid
US4483778A (en) * 1983-12-22 1984-11-20 The Procter & Gamble Company Peroxygen bleach activators and bleaching compositions
US4486327A (en) * 1983-12-22 1984-12-04 The Procter & Gamble Company Bodies containing stabilized bleach activators
EP0150532A1 (en) 1983-12-22 1985-08-07 The Procter & Gamble Company Peroxygen bleach activators and bleaching compositions
US4539130A (en) * 1983-12-22 1985-09-03 The Procter & Gamble Company Peroxygen bleach activators and bleaching compositions
US4655781A (en) * 1984-07-02 1987-04-07 The Clorox Company Stable bleaching compositions
US4659519A (en) * 1984-07-02 1987-04-21 The Clorox Company Process for synthesizing alkyl monoperoxysuccinic acid bleaching compositions
US4859800A (en) * 1986-11-06 1989-08-22 The Clorox Company Phenoxyacetate peracid precursors
US4886658A (en) * 1988-12-14 1989-12-12 The Procter & Gamble Company Oral treatment method for reducing plaque with reduced staining
US4956117A (en) * 1986-11-06 1990-09-11 The Clorox Company Phenoxyacetate peracid precursors and perhydrolysis systems therewith
US5049305A (en) * 1986-11-06 1991-09-17 Zielske Alfred G Phenoxyacetate peracid precursors and perhydrolysis systems therewith
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
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
US5753138A (en) * 1993-06-24 1998-05-19 The Procter & Gamble Company Bleaching detergent compositions comprising bleach activators effective at low perhydroxyl concentrations
US5879409A (en) * 1996-02-23 1999-03-09 The Procter & Gamble Company Bleach additive and bleaching compositions having glycine anhydride activators
US6197737B1 (en) * 1993-05-20 2001-03-06 The Procter & Gamble Company Bleaching compounds comprising substituted benzoyl caprolactam bleach activators
US20060094617A1 (en) * 2004-11-01 2006-05-04 Price Kenneth N Benefit agent delivery system comprising ionic liquid
US20090233829A1 (en) * 2004-11-01 2009-09-17 Stacie Ellen Hecht Multiphase cleaning compositions having ionic liquid phase
WO2011070171A1 (en) 2009-12-10 2011-06-16 Galderma Research & Development Derivatives of novel peroxides, method of preparation thereof and use thereof in human medicine as well as in cosmetics for the treatment or prevention of acne
WO2011070170A1 (en) 2009-12-10 2011-06-16 Galderma Research & Development Novel peroxide derivatives, their process of preparation and their use in human medicine and in cosmetics for the treatment or prevention of acne

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2653738A1 (de) * 1976-11-26 1978-06-01 Schuelke & Mayr Gmbh Feste, in waessrigen systemen antimikrobielle wirksamkeit entwickelnde mittel
DE2725067A1 (de) * 1977-06-03 1978-12-14 Schuelke & Mayr Gmbh Alkohlisches desinfektionsmittel mit sporizider wirkung
US7786065B2 (en) * 2005-02-18 2010-08-31 The Procter & Gamble Company Ionic liquids derived from peracid anions

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1539701A (en) * 1920-11-24 1925-05-26 Firm Naamlooze Vennootschap In Process of bleaching, preserving, and increasing the baking qualities of flour and of other milling products
US1950956A (en) * 1931-10-19 1934-03-13 Marshall Field & Company Method of coating chloramine and product thereof
US2222830A (en) * 1937-10-14 1940-11-26 Monsanto Chemicals Stabilized reactive salt mixture

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1539701A (en) * 1920-11-24 1925-05-26 Firm Naamlooze Vennootschap In Process of bleaching, preserving, and increasing the baking qualities of flour and of other milling products
US1950956A (en) * 1931-10-19 1934-03-13 Marshall Field & Company Method of coating chloramine and product thereof
US2222830A (en) * 1937-10-14 1940-11-26 Monsanto Chemicals Stabilized reactive salt mixture

Cited By (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3248336A (en) * 1964-04-06 1966-04-26 Fmc Corp Aqueous bleaching solutions of peroxycarboxylic acids
US3384596A (en) * 1965-12-30 1968-05-21 Dow Chemical Co Peroxy acid bleaching systems
US3988433A (en) * 1973-08-10 1976-10-26 The Procter & Gamble Company Oral compositions for preventing or removing stains from teeth
US4058131A (en) * 1974-09-16 1977-11-15 Colgate-Palmolive Company Improving hair body and manageability with diperisophthalic acid
US4483778A (en) * 1983-12-22 1984-11-20 The Procter & Gamble Company Peroxygen bleach activators and bleaching compositions
US4486327A (en) * 1983-12-22 1984-12-04 The Procter & Gamble Company Bodies containing stabilized bleach activators
EP0150532A1 (en) 1983-12-22 1985-08-07 The Procter & Gamble Company Peroxygen bleach activators and bleaching compositions
US4539130A (en) * 1983-12-22 1985-09-03 The Procter & Gamble Company Peroxygen bleach activators and bleaching compositions
US4655781A (en) * 1984-07-02 1987-04-07 The Clorox Company Stable bleaching compositions
US4659519A (en) * 1984-07-02 1987-04-21 The Clorox Company Process for synthesizing alkyl monoperoxysuccinic acid bleaching compositions
US4859800A (en) * 1986-11-06 1989-08-22 The Clorox Company Phenoxyacetate peracid precursors
US4956117A (en) * 1986-11-06 1990-09-11 The Clorox Company Phenoxyacetate peracid precursors and perhydrolysis systems therewith
US5049305A (en) * 1986-11-06 1991-09-17 Zielske Alfred G Phenoxyacetate peracid precursors and perhydrolysis systems therewith
US4886658A (en) * 1988-12-14 1989-12-12 The Procter & Gamble Company Oral treatment method for reducing plaque with reduced staining
US6197737B1 (en) * 1993-05-20 2001-03-06 The Procter & Gamble Company Bleaching compounds comprising substituted benzoyl caprolactam bleach activators
US6352562B1 (en) 1993-05-20 2002-03-05 The Procter & Gamble Co. Method of cleaning fabrics using bleaching compounds comprising substituted benzoyl caprolactam 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
US5753138A (en) * 1993-06-24 1998-05-19 The Procter & Gamble Company Bleaching detergent compositions comprising bleach activators effective at low perhydroxyl concentrations
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
US5879409A (en) * 1996-02-23 1999-03-09 The Procter & Gamble Company Bleach additive and bleaching compositions having glycine anhydride activators
US20060094617A1 (en) * 2004-11-01 2006-05-04 Price Kenneth N Benefit agent delivery system comprising ionic liquid
US20090233829A1 (en) * 2004-11-01 2009-09-17 Stacie Ellen Hecht Multiphase cleaning compositions having ionic liquid phase
US7928053B2 (en) 2004-11-01 2011-04-19 The Procter & Gamble Company Multiphase cleaning compositions having ionic liquid phase
US7939485B2 (en) 2004-11-01 2011-05-10 The Procter & Gamble Company Benefit agent delivery system comprising ionic liquid
WO2011070171A1 (en) 2009-12-10 2011-06-16 Galderma Research & Development Derivatives of novel peroxides, method of preparation thereof and use thereof in human medicine as well as in cosmetics for the treatment or prevention of acne
WO2011070170A1 (en) 2009-12-10 2011-06-16 Galderma Research & Development Novel peroxide derivatives, their process of preparation and their use in human medicine and in cosmetics for the treatment or prevention of acne
CN102740826A (zh) * 2009-12-10 2012-10-17 盖尔德马研究及发展公司 新型过氧化物的衍生物、其制备方法及其在人类医学中以及在化妆品中用于治疗或预防痤疮的用途
CN102740826B (zh) * 2009-12-10 2014-12-31 盖尔德马研究及发展公司 过氧化物的衍生物、其制备方法及其在人类医学中以及在化妆品中用于治疗或预防痤疮的用途
US9102607B2 (en) 2009-12-10 2015-08-11 Galderma Research & Development Peroxide derivatives, their process of preparation and their use in human medicine and in cosmetics for the treatment or prevention of acne

Also Published As

Publication number Publication date
NL248201A (zh) 1900-01-01
BE587389A (zh)
DE1105092B (de) 1961-04-20
FR1247242A (fr) 1980-10-17
CH390442A (fr) 1965-04-15
GB886188A (en) 1962-01-03

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