US3756776A - Bleaching process and composition - Google Patents

Bleaching process and composition Download PDF

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Publication number
US3756776A
US3756776A US00151911A US3756776DA US3756776A US 3756776 A US3756776 A US 3756776A US 00151911 A US00151911 A US 00151911A US 3756776D A US3756776D A US 3756776DA US 3756776 A US3756776 A US 3756776A
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United States
Prior art keywords
bleaching
peroxide
benzoyl
peroxides
detergent
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Expired - Lifetime
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US00151911A
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English (en)
Inventor
P Speakman
D Stewart
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Procter and Gamble Co
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Procter and Gamble Co
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Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/39Organic or inorganic per-compounds
    • C11D3/3945Organic per-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
    • D06L4/15Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen using organic agents

Definitions

  • This invention relates to a bleaching process and to bleaching compositions employing an organic bleaching a cut.
  • Certain organic peroxygen compounds have been disclosed as bleaching agents effective at these lower temperatures.
  • One class includes the organic aliphatic and aromatic peroxycarboxylic acids, and especially the more effective aromatic percarboxylic acids such as those described in US. Pat. 3,075,921 issued Jan. 29, 1963 to Brocklehurst et al. These compounds, however, are generally unstable; they tend to lose their activity rapidly in storage, and in some cases may be explosive. Thus, they are difiicult to handle in processing and in use. Furthermore, this instability is intensified by traces of metals such as iron, nickel, cobalt, copper and the like.
  • the organic peroxides and in particular the diacyl peroxides, comprise another class of peroxygen bleaching agents. Some of these compounds are described in Belgian patent specification 603,768. These substances hydrolyze in the presence of water to form peroxycarboxylic acids, which are believed to be the substances actually responsible for the bleaching activity.
  • the organic peroxides tend to be unstable and in some cases are explosive. Many are only slightly soluble in water, and therefore, hydrolyze slowly at moderate washing temperatures. Thus, little of the actual bleaching agent may be released in the duration of an ordinary washing process.
  • Dibenzoyl peroxide is an example of an unstable and slightly-soluble peroxide compound.
  • Benzoyl succinyl peroxide is one of the preferred diacyl peroxides set forth in Belgian specification 603,768; this compound is soluble in water, under neutral or alkaline conditions. Nevertheless, it is unstable in detergent compositions. Explosivity tests indicate that it may detonate upon impact. Although detergent compositions are unlikely to be subjected in ordinary use to the impact applied in an impact test (as described in Example III hereafter),
  • benzoyl glutaryl peroxides of this invention are stable in detergent compositions and are non-explosive, even in the presence of metal ions such as iron, nickel, cobalt, copper and the like.
  • metal ions such as iron, nickel, cobalt, copper and the like.
  • these benzoyl glutaryl peroxides being soluble in alkaline washing and bleaching liquors, hydrolyze rapidly during a washing or bleaching process, forming an aromatic peroxy acid as the effective bleaching agent.
  • the benzoyl glutaryl peroxides are, therefore, very valuable bleaching agents for use at temperatures below about C.; they are also effective at higher temperatures.
  • the present invention provides a process for bleaching textile materials which comprises treating such materials with an aqueous solution of a benzoyl glutaryl peroxide of the general formula where R is phenyl or substituted phenyl.
  • the present invention provides bleaching compositions containing a benzoyl glutaryl peroxide of the invention in combination with a detergent salt and/or organic surface active agent.
  • benzoyl glutaryl peroxides suitable herein are those corresponding to the hereinbefore described formula.
  • Preferred peroxides are those where the benzoyl radical is unsubstituted or is substituted by one or more chlorine, methyl or methoxy groups.
  • Suitable substituted benzoyl glutaryl peroxides include m-chloro benzoy] glutaryl peroxide, p-methylbenzoyl glutaryl peroxide, p-methoxybenzoyl glutaryl peroxide.
  • the peroxides of the invention are employed in a solution at a concentration which provides from 1 to 200 p.p.m. by weight of available oxygen in the solution.
  • a preferred concentration is from 5 to 150 p.p.n1., especially from 10 to 40 ppm.
  • the benzoyl glutaryl peroxides of the invention can be prepared in accordance with methods known in the art. Suitable methods of preparation include, for example, reaction of an aromatic peroxy acid with glutaric anhydride in a suitable solvent, or reaction of an aroylchloride with mono perglutaric acid in the presence of an equivalent weight of a base.
  • Suitable methods of preparation include, for example, reaction of an aromatic peroxy acid with glutaric anhydride in a suitable solvent, or reaction of an aroylchloride with mono perglutaric acid in the presence of an equivalent weight of a base.
  • the preparation of benzoyl glutaryl peroxide is disclosed by Zeit. f. Physio]. Chemie, 323, pp. 211-235 (1961), incorporated by reference herein.
  • compositions are preferably, but not necessarily, particulate solids.
  • the compositions can contain inorganic or organic detergent builder salts. They can contain, for example, alkaline inorganic builder salts such as the alkali metal carbonates, silicates, phosphates and polyphosphates.
  • Suitable organic water-soluble builder salts include the aminopolycarboxylates, particularly sodium nitrilotriacetates, organic polyphosphonates such as ethane-l-hydroxy-l, l-diphosphonates, sodium citrate, sodium gluconate and the like.
  • the builder salts herein are employed in an amount of from 1% to 99% by weight of the compositions of the invention.
  • Neutral diluent salts such as alkali metal chlorides or sulfates can be employed.
  • Compatible watersoluble organic surface-active agents, including anionic, nonionic, Zwitterionic and ampholytic detergents can also be present, for example, in an amount of up to by weight.
  • the amounts of these components, i.e., the inorganic or organic builder salts and organic surface-active agents used depend on both the nature of the organic detergent and the intended purpose of the products. Normally the proportions of such components will correspond to a weight ratio of builder to detergent of from about 30:1 to 1:4, preferably from 9:1 to 1:1.
  • Particularly suitable organic anionic detergents are the water-soluble soaps and the alkyl benzene sulfonates, especially linear alkyl benzene sulfonates, alkyl sulfates, olefin sulfates and other organic sulfates and sulfonates.
  • Suitable nonionic detergents include the polyethylene oxide condensates with polypropylene oxides, e.g., the Pluronics (trade name), or with fatty alcohols, alkyl phenols, fatty acids and the like.
  • Suitable detergents herein are those described in U.S. Pat. 3,351,558 to Roger B. Zimmerer at column 6, line 59 to column 9, line 69, incorporated herein by reference.
  • compositions can also contain the usual minor components of conventional bleaching and washing compositions such as colors, perfume, tarnish inhibitors stabilizers for the bleach, optical brighteners, enzymes, dust preventatives, suds-enhancing or suds-depressing agents, abrasives and the like.
  • compositions of the invention provide desira ble oxidizing and bleaching functions to facilitate the removal of soils and stains on fabrics treated therewith.
  • the compositions can be used in connection with conventional laundering operations such as soaking, washing, rinsing and the like to remove soils and stains from laundered fabrics, such as cottons, linens and the like.
  • the peroxides described hereinbefore are more stable during storage in detergent compositions than prior known water-soluble organic peroxy bleaching agents, it is desirable to provide protection from atmospheric or other moisture and from other components of the compositions. This can be effected for instance, by coating the peroxide with an inert material, or by mixing the peroxides with an inert or stabilizing substance and coating the mixture. Alternatively the mixture can be agglomerated or extruded in the form of noodles, ribbons, flakes or the like. Other suitable methods of providing protection from moisture can be employed.
  • the proportion of the benzoyl glutaryl peroxide in the compositions of the invention should be such as to provide a concentration of available oxygen in the ranges defined hereinbefore when the compositions are used at the intended concentration in a bleaching or washing liquor.
  • the compositions intended to be used at conventional concentrations for household washing would normally contain enough benzoyl glutaryl peroxide to provide from 0.1% to 3% by weight of the composition of available oxygen, preferably 0.2% especially from 0.2% to 1%.
  • a process for bleaching textile materials which consists essentially of treating such materials with an aqueous solution of benzoyl glutaryl peroxide of the formula parts per million by weight of available oxygen in solution.
  • a bleaching composition consisting essentailly of a mixture of a water-soluble organic detergent selected from the group consisting of anionic, nonionic, Zwitterionic and ampholytic detergents and a water-soluble inorganic or oragnic detergency builder salt in a ratio of detergency builder salt to detergent of from 30:1 to 1:4; and a benzoyl peroxide bleaching agent of the formula RCO 'OO CO (CH CO H wherein R is phenyl or substituted phenyl; said substituted phenyl being substituted with one or more Cl, OCH or -CH;; radicals.
  • the bleaching composition of claim 7 having sufiicient benzoyl glutaryl peroxide to provide from 0. 1% to 3% by weight of the composition of available oxygen.
  • composition of claim 8 wherein the ratio of builder salt to detergent is from about 3:1 to 100:1, especially from 9:1 to 1:1.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (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)
  • Detergent Compositions (AREA)
US00151911A 1970-06-15 1971-06-10 Bleaching process and composition Expired - Lifetime US3756776A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB5896/71A GB1293063A (en) 1970-06-15 1970-06-15 Bleaching process and composition
GB2887570 1970-06-15

Publications (1)

Publication Number Publication Date
US3756776A true US3756776A (en) 1973-09-04

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US00151911A Expired - Lifetime US3756776A (en) 1970-06-15 1971-06-10 Bleaching process and composition
US00151910A Expired - Lifetime US3756775A (en) 1970-06-15 1971-06-10 Bleaching process and composition

Family Applications After (1)

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US00151910A Expired - Lifetime US3756775A (en) 1970-06-15 1971-06-10 Bleaching process and composition

Country Status (9)

Country Link
US (2) US3756776A (fr)
BE (1) BE768469A (fr)
CA (2) CA969711A (fr)
CH (1) CH540974A (fr)
DE (1) DE2128945A1 (fr)
ES (1) ES392022A1 (fr)
FR (1) FR2095265B1 (fr)
GB (1) GB1293063A (fr)
NL (1) NL7108112A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5000874A (en) * 1987-06-26 1991-03-19 Sandoz Ltd. Concentrated compositions and their use as stabilizers for peroxide-containing alkaline liquors

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4391723A (en) * 1981-07-13 1983-07-05 The Procter & Gamble Company Controlled release laundry bleach product
US4847089A (en) * 1986-07-16 1989-07-11 David N. Kramer Cleansing and distinfecting compositions, including bleaching agents, and sponges and other applicators incorporating the same
US4917815A (en) * 1988-06-10 1990-04-17 Sterling Drug Inc. Stable aqueous aromatic percarboxylic acid solution
EP0717102A1 (fr) 1994-12-09 1996-06-19 The Procter & Gamble Company Composition détergente liquide pour lave-raisselle automatique contenant des peroxydes de diacyle
DE69515331T2 (de) * 1994-12-09 2000-10-19 The Procter & Gamble Company, Cincinnati Diacylperoxydteilchen enthaltende zusammensetzungen für automatische geschirreinigung
JPH11503787A (ja) * 1995-04-17 1999-03-30 ザ、プロクター、エンド、ギャンブル、カンパニー ジアシルペルオキシドを含有する複合粒子の製法および用途
US5776877A (en) * 1995-05-25 1998-07-07 The Clorox Company Liquid peracid precursor colloidal dispersions: macroemulsions
US5681805A (en) * 1995-05-25 1997-10-28 The Clorox Company Liquid peracid precursor colloidal dispersions: microemulsions
US5663133A (en) * 1995-11-06 1997-09-02 The Procter & Gamble Company Process for making automatic dishwashing composition containing diacyl peroxide
JP2000500808A (ja) 1996-07-24 2000-01-25 ザ、プロクター、エンド、ギャンブル、カンパニー ブリーチを含有したスプレーしうる液体またはゲル洗剤組成物

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5000874A (en) * 1987-06-26 1991-03-19 Sandoz Ltd. Concentrated compositions and their use as stabilizers for peroxide-containing alkaline liquors

Also Published As

Publication number Publication date
BE768469A (fr) 1971-12-14
FR2095265B1 (fr) 1974-03-08
GB1293063A (en) 1972-10-18
NL7108112A (fr) 1971-12-17
CH540974A (de) 1973-08-31
DE2128945A1 (de) 1971-12-16
CA969712A (en) 1975-06-24
US3756775A (en) 1973-09-04
FR2095265A1 (fr) 1972-02-11
ES392022A1 (es) 1974-08-01
CA969711A (en) 1975-06-24

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