US3007876A - Solid organic bleach compositions - Google Patents

Solid organic bleach compositions Download PDF

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Publication number
US3007876A
US3007876A US697793A US69779357A US3007876A US 3007876 A US3007876 A US 3007876A US 697793 A US697793 A US 697793A US 69779357 A US69779357 A US 69779357A US 3007876 A US3007876 A US 3007876A
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US
United States
Prior art keywords
chlorine
bleaching
compound
dione
tetrahydroquinazoline
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 - Lifetime
Application number
US697793A
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English (en)
Inventor
John R Schaeffer
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.)
Procter and Gamble Co
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Procter and Gamble 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.)
Filing date
Publication date
Priority to BE571630D priority Critical patent/BE571630A/xx
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Priority to US697793A priority patent/US3007876A/en
Priority to DEP21558A priority patent/DE1223978B/de
Priority to FR779436A priority patent/FR1215341A/fr
Priority to GB37611/58A priority patent/GB847566A/en
Application granted granted Critical
Publication of US3007876A publication Critical patent/US3007876A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C11D3/395—Bleaching agents
    • C11D3/3955—Organic bleaching agents
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/20—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which contain halogen
    • D06L4/27—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which contain halogen using organic agents

Definitions

  • This invention relates to a solid organic chlorinated bleaching and oxidizing agent.
  • the invention comprises a new class of compounds, N,N'-dichlorobenzoyleneureas.
  • Bleaching materials in powdered form are very de- They can be used alone to make an active bleaching solution or, more commonly, they can be used with powdered or granular detergents or cleansers, becoming active when used with water.
  • a suitable powdered bleach should have strong bleaching power, good stability, and reasonable compatibility with detergents or other materials with which it is to be associated, and should not have an objectionable odor.
  • Nearly all of the common powdered chlorinated bleaches are deficient in one or more of these properties, although chlorinated powdered bleaches which hydrolyze to form hypochlorous acid, a strong bleaching and oxidizing agent, are usually considered the most satisfactory.
  • Common inorganic powdered bleaches include sodium perborate which is low in practical bleaching capacity and calcium hypochlorite which furnishes calcium ions that increase water hardness.
  • chlorinated organic compounds have been developed.
  • those chlorinated organic compounds such as N-chloramines which have a high percentage of available chlorine, a term hereinafter defined, are undesirably odoriferous, e.g. some have a nauseating lachrymatory odor, are unstable, or are incompatible with materials with which they may be associated.
  • Those chlorinated organic compounds which do not have undesirable odors, which are stable or which are compatible with detergents usually have low bleaching activity or have a low percentage of available chlorine.
  • percent available chlorine is used to indi cate the oxidizing capacity of a chlorine containing compound. It is that weight of elemental chlorine (C1 that would exert the same oxidizing action as 100 parts of the chlorine compound in question.
  • N-chloramines which include chloramines, chloramides, chlorimines and chlorimides are discussed in volume 3 f the Kirk-Othmer Encyclopedia of Chemical Technology, pages 664-676.
  • hypochlorous acid is apparently formed from the available chlorine in the compound and the original amine, amide, imine or imide is formed when hydrogen from the water replaces the chloline as shown in the following general equation:
  • hypochlorous acid or hypochlorite ions resulting from the hydrolysis of the N-chloramines.
  • Hypochlorous acid and hypochlorite ions are believed to be the source of the bleaching activity of N-chloramines.
  • N-chloramines are unstable, losing most of the available chlorine which they contain within a very short time. Moreover, the bleaching effectiveness of an N-chloro organic compound cannot be predicted, even if itis stable.
  • N,N'dichlorobenzoyleneureas of this invention were found quite unexpectedly to be highly satisfactory stable bleaching agents with little odor since N-monochlorobenzoyleneurea is not stable.
  • the N,N'dichlorobenzoyleneureas of this invention can be produced by chlorinating benzoyleneurea or its simple derivatives.
  • Benzoyleneurea tetrahydroquinazoline-2,4-dione
  • Benzoyleneurea tetrahydroquinazoline-2,4-dione
  • Benzoyleneurea has the following structural formula:
  • a compound of this invention 1,3-dichloro-tetrahydroquinazoline-2,4-dione, can be obtained, for example, by replacing the hydrogen atoms attached to the nitrogen atoms of the heterocyclic ring with chlorine atoms.
  • Simple derivatives of 1,3 -dichloro-tetrahydroquinazoline-2,4-dione function as stable effective bleaching agents in substantially the same manner as the parent compound.
  • Simple derivatives are those compounds in which hydrogen atoms are substituted in the carbocyclic ring with monovalent radicals which do not affect the active chlorine atoms in the heterocyclic ring.
  • Such radicals are chloro, bromo, iodo, ethyl and methyl and can substitute hydrogen atoms in the 5, 6, 7 and 8 positions in the carbocyclic ring.
  • Example 1 The preferred method for producing 1,3-dichloro-tetrahydroquinazoline-2,4-dione involves introducing about four-moles of chlorine gas into an aqueous suspension of about one mole of benzoyleneurea and about 2.5 moles of sodium carbonate at a temperature of about C. The product is then recovered by filtering the reaction mixture, washing the filtrate three times with ice water and drying the product over phosphorous pentoxide. It has been observed that the chlorine gas should be added rapidly in order to ensure that the mole ratio of chlorine p to benzoyleneurea' is about 4:1. This much excess chlorine is necessary to prevent hydrolysis of the compound in the alkaline solution. If about three moles of chlorine is used the reaction product apparently has less stability.
  • 1,3-dichloro-tetrahydroquin azoline-2,4-dione after recrystallization, has about 60% available chlorine and will lose only about 6% of this available chlorine when the compoundis stored in a thin layer (about ,4 inch) for 10 days at 12 0 F. and 50% relative humidity.
  • V 4 sulfated fatty alcohol .(sodium salt) which was derived from 'the reduction of tallow and sodium polypropylene benzene sulfonate the polypropylene radical averaging about 12 carbons, 8% moisture, 6% sodium 7 V silicate and the remainder consisting of smallamounts of sodium carboxymethylcellulose, perfume, fluorescent brightening agents, lauryl alcohol and coconut oil fatty acid ethanolamide.
  • the bleach was present in an amount equivalent to 2.6% initial available chlorine by weight of the sample in each case.
  • the samples were stored in a layer /2 inch thick at 80 'F. for one month.
  • The'N,N'dichlorobenzoyleneurea compounds ofthis invention when used to bleach fabrics do not cause pinholing, acommon fault of most other solidchlorinated bleaches. Pinholing is the destruction of a very small area o f fabric due to high localized concentration of oxidizing agent. Even though the N,Ndichlorobenzoyleneureas are very effective bleaches and are only slightly soluble, they do not have this fault even when used with cotton fabrics which are particularly susceptible to am age under the conditions .described.
  • the bleaching capacity of chlorinated compounds is measured by their ability to oxidize the stains commonly found in soiled fabrics and other materials to colorless products. his well known'that while'dirt'can be washed away by detergents, stains require'the chemical action of oxidizing bleaches.
  • N,N'dichlorobenzoyleneureasof this invention are I believed to hydrolyze, especially in an alkaline solution,
  • the 'N,N'dichlorobenzoyleneureas are only slightly soluble in water, but it has been found that this'does not impair their high bleaching capacity as they are effectively dispersed in water. These compounds have a very slight chlorine odor which is inoifensive. They have ben observed to be compatible with detergent compositions.
  • the tests consisted of washing a piece of stained cloth in a Launderometer.
  • the Launderometer and its use are described in Schwartz and Perry, Surface Active Agents (1949),
  • a dry bleach composition characterized by a high degree of bleaching effectiveness, stability and compatibility comprising as its essential bleaching ingredient a N,N'dichlorobenzoyleneurea compound which has the structure X3 IO] X6 N-Cl where X X X and X are each a radical selected from the group consisting of hydrogen, chlorine, bromine, iodine, ethyl and methyl, and an inorganic water soluble alkaline agent said bleaching ingredient being present in suflicient amount to provide bleaching activity and said alkaline agent being present in sufficient amount to provide an alkaline solution when said composition is dispersed in water.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (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)
US697793A 1957-11-21 1957-11-21 Solid organic bleach compositions Expired - Lifetime US3007876A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BE571630D BE571630A (en, 2012) 1957-11-21
US697793A US3007876A (en) 1957-11-21 1957-11-21 Solid organic bleach compositions
DEP21558A DE1223978B (de) 1957-11-21 1958-10-20 Wasch- und Reinigungsmittel mit Bleichwirkung
FR779436A FR1215341A (fr) 1957-11-21 1958-11-18 Agent de blanchiment organique
GB37611/58A GB847566A (en) 1957-11-21 1958-11-21 Bleaching and oxidizing agents

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US697793A US3007876A (en) 1957-11-21 1957-11-21 Solid organic bleach compositions

Publications (1)

Publication Number Publication Date
US3007876A true US3007876A (en) 1961-11-07

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ID=24802564

Family Applications (1)

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US697793A Expired - Lifetime US3007876A (en) 1957-11-21 1957-11-21 Solid organic bleach compositions

Country Status (5)

Country Link
US (1) US3007876A (en, 2012)
BE (1) BE571630A (en, 2012)
DE (1) DE1223978B (en, 2012)
FR (1) FR1215341A (en, 2012)
GB (1) GB847566A (en, 2012)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4267325A (en) * 1979-02-27 1981-05-12 Cadbury-Schweppes Limited Bleaching agents
US4452868A (en) * 1982-12-29 1984-06-05 Gould Inc. Metal-chlorine cell with storage of chlorine

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2621162A (en) * 1952-12-09 J-propargyl-x-quinazolones and acid
US2938764A (en) * 1957-02-25 1960-05-31 Wyandotte Chemicals Corp Highly alkaline dichlorodimethylhydantoin bleaching solutions and methods

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2621162A (en) * 1952-12-09 J-propargyl-x-quinazolones and acid
US2938764A (en) * 1957-02-25 1960-05-31 Wyandotte Chemicals Corp Highly alkaline dichlorodimethylhydantoin bleaching solutions and methods

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4267325A (en) * 1979-02-27 1981-05-12 Cadbury-Schweppes Limited Bleaching agents
US4452868A (en) * 1982-12-29 1984-06-05 Gould Inc. Metal-chlorine cell with storage of chlorine

Also Published As

Publication number Publication date
DE1223978B (de) 1966-09-01
GB847566A (en) 1960-09-07
BE571630A (en, 2012)
FR1215341A (fr) 1960-04-15

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