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US3589857A - Process of bleaching textiles - Google Patents

Process of bleaching textiles Download PDF

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Publication number
US3589857A
US3589857A US677745A US3589857DA US3589857A US 3589857 A US3589857 A US 3589857A US 677745 A US677745 A US 677745A US 3589857D A US3589857D A US 3589857DA US 3589857 A US3589857 A US 3589857A
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Prior art keywords
bleaching
sodium
alkyl
peroxide
activator
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US677745A
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Leo Thomas Murray
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Colgate Palmolive Co
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Colgate Palmolive 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
    • C11D3/3902—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
    • 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
    • D06L4/10—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen
    • D06L4/12—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs using agents which develop oxygen combined with specific additives

Definitions

  • the present invention relates, in general, to compositions advantageously adapted for use in connection with fabric washing and bleaching operations and, in particu lar, to the provision of specific compounds and compositions for such purposes, said compositions being capable of providing an exceptionally high order of bleaching activity.
  • bleaching agents as an adjunct to fabric Washing operations is, of course, common practice if not a recognized necessity. Consequently, many of the detergent compositions currently available commercially contain predetermined amounts of bleaching agent as an essential ingredient; specific representatives of bleaching agents found to be suitable in this regard are well known in the art being extensively described in the published literature both patent and otherwise and include, for example, the chlorine bleaches such as the alkali metal hypochlorites; active oxygen-releasing peroxide compounds such as inorganic persalts e.g., the perborates, percarbonates, perphosphates, persilicates, persulfates, hydrogen peroxide, sodium peroxide and the like.
  • the chlorine bleaches such as the alkali metal hypochlorites
  • active oxygen-releasing peroxide compounds such as inorganic persalts e.g., the perborates, percarbonates, perphosphates, persilicates, persulfates, hydrogen peroxide, sodium peroxide and the like.
  • peroxide type bleaching agents are, in general, preferred for use being found to be markedly superior as regards capability of providing a fabric having a softer hand, improved absorbency, permanence of Whites and the like.
  • other types of bleaching agents currently enjoying relatively widespread commercial exploitation invariably yield fabrics having a pronounced tendency to develop spurious discoloration, e.g., yellowing.
  • fabric materials treated with bleachagents of this type in many instances, exhibit significant loss in strength and thus the frequency of bleaching may be such as to severely curtail the useful life of the fabric material.
  • washing operations requiring a comparatively high order of bleaching activity at reduced temperature ranges invariably necessitate resort to the use of bleaching agents other than those of the peroxide type despite the attendant disadvantages necessarily involved, e.g. with respect to 3,589,857 Patented June 29, 1971 possible impairment of fabric strength, inferior resistance to discoloration, etc.
  • activator compounds of this type function function together as a precursor system by which in situ generation of species providing effective bleaching means is made possible.
  • a primary object of the present invention resides in the provision of activator compounds specifically and advantageously adapted for conjoint use with peroxide compounds in bleach and/or detergent compositions wherein one or more of the disadvantages characterizing many of the compounds heretofore suggested for such purposes are eliminated, or at least alleviated to a substantial degree.
  • a further object of the present invention resides in the provision of activator compounds capable of augmenting the bleaching capacity of peroxide compounds to the extent of rendering such materials feasible for use in detergent and/or bleaching compositions at temperatures below about C.
  • Another object of the present invention resides in the provision of bleaching and detergent compositions capable of yielding fabric materials having satisfactory absorbency, softness of hand and resistance to discoloration for extended periods of time under varying conditions of use.
  • activator compounds beneficially adapted for use in conjunction with peroxide bleaching agents, said activator compounds comprising water soluble chloroformates selected from the group consisting of alkyl and aryl chloroformates.
  • chloroformate derivatives contemplated for use in accordance with the present invention may, for convenience, be represented according to the following structural formula:
  • R represents alkyl and preferably lower alkyl of from 1 to 4 carbon atoms e.g. methyl, ethyl, propyl, isobutyl, etc. and aryl e.g. phenyl.
  • substituents include, for example, halogen e.g. chloro, bromo, etc.
  • R represents methyl, ethyl, and phenyl respectively i.e., methyl chloroformate, ethylchloroformate, and phenylchloroformate.
  • chloroformate derivatives of the present invention are well known compounds with methods for their prepa ration being described in the published prior art, both patent and otherwise.
  • reference is made to, for example, Dumas, PeligotAnnales de Chimie et de Physique [2], 58, 52; ibid 54, 226 and Kempf, Journal fiir Praktician Chimie, [2], l, 403.
  • the chloroformate activators described herein are uniformly characterized in possessing outstanding capacity to augment the bleaching activity of peroxide compounds. This, of course, provides the salient advantage that the beneficial properties uniquely typical of the more mildlyacting peroxide bleaching agents such as typified by the perborates e.g. sodium perborate, are made possible at temperature ranges conventionally employed in home laundering operation.
  • a further advantage accrues from the fact that bleaching and/ or detergent composition formulated with the chloroformate activator are devoid of any tendency to weaken or otherwise deleteriously affect the strength of the fabric or textile material treated therewith, the term textile being used herein to connote synthetic fibers as well as products manufactured therewith.
  • compositions of the present invention may be utilized in connection with the bleaching and washing of cellulose as well as synthetic fibers such as polyamides without risk of fabric impairment.
  • the compositions described herein exhibit negligible tendency, if any, to attack the colorant present in the fiber.
  • the washed fabric material displays superior resistance to discoloration i.e., any yellowing tendency is not evident, while sustaining a high degree of whiteness over extended periods of time and use.
  • a further advantage relates to the fact that the chloroformate activator in combination with perborate bleaching agents in particular, affords to the user great latitude in determining and thus controlling the level of bleaching activity. This may be readily achieved in view of the comparatively mild bleaching action of the peroxides. Thus, any possibility of over-bleaching is minimized despite significant variations in the concentration of peroxide.
  • the chloroformate activators of the present invention may be effectively employed either singly or in admixtures comprising two or more.
  • the efficacy of a given manner of proceeding depends primarily upon the existing requirements i.e., the specific problem to be negotiated by the bleach composition.
  • optimum mixtures of chloroformates can be readily determined in a given circumstance by routine laboratory investigation.
  • the employment of the chloroformate in admixture presents, of course, the singular advantage that the beneficial properties of a plurality of chloroformates can be obtained in a single composition.
  • the relative proportions of bleaching agent and chloroformate activator employed may vary over a relatively wide range depending somewhat upon the nature of the composition being formulated. In general, beneficial results are readily obtained by the use of the activator in amounts sufficient to yield a chloroformate peroxide mole ratio within the range of from about 0.01 to about '2.0 with a range of from 0.1 to 2.0 being preferred.
  • the involved ingredients will comprise, essentially, the chloroformate activator and peroxide.
  • the peroxide compound will usually be utilized in amounts sufiicient to yield a concentration within the range of from about 1% to about 50%, weight basis, of total composition, with other ingredients including detergent, brightener, perfume, etc.
  • chloroformate activators described herein can likewise be employed to outstanding advantage in combination with one or more of the conventional activator compounds currently available commercially. Again, the choice of particular systems as well as concentrations lies largely within the discretion of the manufacturer. In any event, it is preferred that the chloroformate compound be used in major proportions in those instances wherein activator mixtures are employed.
  • the activator/bleaching agent system may be formulated together in a built detergent composition or alternatively as a separate bleach product.
  • the activator and bleach may be either intimately mixed or included in separate compartments of a water soluble film packet. Any of the usual methods for providing the normally liquid activator compound in powder or other suitable solid form may be resorted to for such purposes, e.g. encapsulation.
  • the significant increase in ARd for those cotton samples treated with the alkyl chloroformate activator-perborate systems indicates that a highly efficient and active bleaching function obtained when compared to the control sample subjected to the bleaching action of the perborate alone absent the activator additive.
  • the reflectance for a given material is a direct function of its degree of whiteness; thus, greater difference in the ARd value are indicative of correspondingly higher bleaching activity.
  • composition containing the chloroformate activators described herein can be provided in the form of a bleaching composition or alternatively in the form of a built detergent product.
  • Organic detergents suitable for use in accordance with the present invention encompass a relatively wide range of materials and may be of the anionic, non-ionic, cationic or amphoteric types.
  • the anionic surface active agents includes those surface active or detergent compounds which contain an organic hydrophobic group and an anionic solubilizing group.
  • anionic solubilizing groups are sulfonate, sulfate, carboxylate, phosphonate and phosphate.
  • Suitable anionic detergents which fall within the scope of the invention include the soaps, such as the water-soluble salts of higher fatty acids or rosin acids, such as may be derived from fats, oils and waxes of animal, vegetable or marine origin, e.g., the sodium soaps of tallow, grease, coconut oil, tall oil and mixtures thereof; and the sulfated and sulfonated synthetic detergents, particularly those having about 8 to 26, and preferably about 12 to 22, carbon atoms to the molecule.
  • the soaps such as the water-soluble salts of higher fatty acids or rosin acids, such as may be derived from fats, oils and waxes of animal, vegetable or marine origin, e.g., the sodium soaps of tallow, grease, coconut oil, tall oil and mixtures thereof
  • the sulfated and sulfonated synthetic detergents particularly those having about 8 to 26, and preferably about 12 to 22, carbon atoms to the molecule.
  • suitable synthetic anionic detergents there may be cited the higher alkyl mononuclear aromatic sulfonates such as the higher alkyl benzene sulfonates containing from 10 to 16 carbon atoms in the alkyl group in a straight or branched chain, e.g., the sodium salts of decyl, undecyl, dodecyl (lauryl), tridecyl, tetradecyl, pentadecyl, or hexadecyl benzene sulfonate and the higher alkyl toluene, xylene and phenol sulfonates; alkyl naphthalene sulfonate, ammonium diamyl naphthalene sulfonate, and sodium dinonyl naphthalene sulfonate.
  • the higher alkyl mononuclear aromatic sulfonates such as the higher alkyl benzene
  • anionic detergents are the olefin sulfonates, including long chain alkene sulfonates, long chain hydroxyalkane sulfonates or mixtures of alkenesulfonates and hydroxyalkanesulfonates.
  • paraffin sulfonates such as the reaction products of alpha olefins and bisulfites (e.g. sodium bisulfite), e.g. primary paraffin sulfonates of about 1020, preferably about 1520, carbon atoms; sulfates of higher alcohols; salts of a-sulfofatty esters (e.g. of about 10-20 carbon atoms, such as methyla-sulfomyristate or a-sulfotallowate).
  • alpha olefins and bisulfites e.g. sodium bisulfite
  • primary paraffin sulfonates of about 1020, preferably about 1520, carbon atoms
  • sulfates of higher alcohols e.g. salts of a-sulfofatty esters (e.g. of about 10-20 carbon atoms, such as methyla-sulfomyristate or a-sulfotallowate).
  • sulfates of higher alcohols are sodium lauryl sulfate, sodium tallow alcohol sulfate. Turkey red oil or other sulfated oils, or sulfates of monoor diglycerides of fatty acids (e.g.
  • alkyl poly (ethenoxy) ether sulfates such as the sulfates of the condensation products of ethylene oxide and lauryl alcohol (usually having 1 to 5 ethenoxy groups per molecule); lauryl or other higher alkyl glyceryl ether sulfonates; aromatic poly (ethenoxy) ether sulfates such as the sulfates of the condensation products of ethylene oxide and nonyl phenol (usually having 1 to 20 oxyethylene groups per molecule preferably 2-12).
  • the suitable anionic detergents include also the acyl sarcosinates (e.g. sodium lauroylsarcosinate) the acyl esters (e.g. oleic acid ester) of isothionates, and the acyl N-methyl taurides (e.g. potassium N-methyl lauroylor oleyl tauride).
  • acyl sarcosinates e.g. sodium lauroylsarcosinate
  • the acyl esters e.g. oleic acid ester
  • acyl N-methyl taurides e.g. potassium N-methyl lauroylor oleyl tauride
  • the most higher preferred water soluble anionic detergent compounds are the ammonium and substituted ammonium (such as mono-, diand triethanolamine), alkali metal (such as sodium and potassium) and alkaline earth metal (such as calcium and magnesium) salts of the higher alkyl sulfates, and the higher fatty acid monoglyceride sulfates.
  • the particular salt will be suitably selected depending upon the particular formulation and the proportions therein.
  • Nonionic surface active agents include those surface active or detergent compounds which contain an organic hydrophobic group and a hydrophilic group which is a reaction product of a solubilizing group such as carboxylate, hydroxyl, amido or amino with ethylene oxide or with the polyhydration product thereof, polyethylene g ycol.
  • nonionic surface active agents which may be used there may be noted the condensation products of alkyl phenols with ethylene oxide, e.g., the reaction product of isooctyl phenol with about 6 to 30 ethylene oxide units; condensation products of higher fatty alcohols such as tridecyl alcohol with ethylene oxide; ethylene oxide addends of monoesters of hexahydric alcohols and inner ethers thereof such as sorbitan, monolaurate, sorbitol mono-oleate and mannitan monopalmitate, and the condensation products of polypropylene glycol with ethylene oxide.
  • condensation products of alkyl phenols with ethylene oxide e.g., the reaction product of isooctyl phenol with about 6 to 30 ethylene oxide units
  • condensation products of higher fatty alcohols such as tridecyl alcohol with ethylene oxide
  • ethylene oxide addends of monoesters of hexahydric alcohols and inner ethers thereof such as sorbitan, monolau
  • Cationic surface active agents may also be employed. Such agents are those surface active detergent compounds which contain an organic hydrophobic group and a cationic solubilizing group. Typical cationic solubilizing groups are amine and quaternary groups.
  • suitable synthetic cationic detergents there may be noted the diamines such as those of the type RNHC H NH wherein R is an alkyl group of about 12 to 22 carbon atoms, such as N-Z-aminoethyl stearyl amine and N-2-aminoethyl myristyl amine; amide-linked amines such as those of the type R CONHC H NH wherein R is an alkyl group of about 9 to 20 carbon atoms, such as N-Z-amino ethyl-stearyl amide and N- amino ethyl myristyl amide; quaternary ammonium compounds wherein typically one of the groups linked to the nitrogen atom is an alkyl group of about 12 to 18 carbon atoms and three of the groups linked to the nitrogen atom are alkyl groups which contain 1 to 3 carbon atoms, including such 1 to 3 carbon alkyl groups bearing inert substituents, such as phenyl groups, and there is present an
  • Typical quaternary ammonium detergents are ethyl-dimethyl-stearyl ammonium chloride, benzyl-dimethylstearyl ammonium chloride, benzyl-dimethyl-stearyl ammonium chloride, trimethyl stearyl ammonium chloride, trimethyl-cetyl ammonium bromide, dimethyl-ethyl dilauryl ammonium chloride, dimethyl-propyl-myristyl ammonium chloride, and the corresponding methosulfates and acetates.
  • amphoteric detergents are those containing both an anionic and a cationic group and a hydrophobic organic group, which is advantageously a higher aliphatic radical, e.g. of -20 carbon atoms.
  • suitable amphoteric detergents are those containing both an anionic and a cationic group and a hydrophobic organic group, which is advantageously a higher aliphatic radical, e.g. of -20 carbon atoms.
  • N-long chain alkyl aminocarboxylic acids 1 2 e.g. of the formula R-NRCOOM
  • the long chain alkyl iminodicarboxylic acids Rs e.g. of the formula RgRCOO-
  • R is a long chain alkyl group, e.g. of about 10-20 carbons
  • R is a divalent radical joining the amino and carboxyl portions of an amino acid (e.g.
  • M is hydrogen or a saltforming metal
  • R is a hydrogen or another monovalent substituent (e.g. methyl or other lower alkyl)
  • R and R are monovalent substituents joined to the nitrogen by carbon-to-nitrogen bonds (e.g.
  • amphoteric detergents are N-alkyl-beta-aminopropionic acid; N-alkyl-betaiminodipropionic acid, and N-alkyl, N,N-dimethyl glycine; the alkyl group may be, for example, that derived from coco fatty alcohol, lauryl alcohol, myristyl alcohol (or a lauryl-myristyl mixture), hydrogenated tallow alcohol cetyl, stearyl, or blends of such alcohols.
  • the substituted aminopropionic and iminodipropionic acids are often supplied in the sodium or other salt forms, which may likewise be used in the practice of this invention.
  • amphoteric detergents examples include the fatty imidazolines such as those made by reacting a long chain fatty acid (e.g. of 10 to 20 carbon atoms) with diethylene triamine and monohalocarboxylic acids having 2 to 6 carbon atoms, e.g. l-coco 5 hydroxethyl-5-carboxymethylimidazoline; betaines containing a sulfonic group instead of the carboxylic group without an intervening nitrogen atom, e.g. inner salts of Z-trimethylamino fatty acids such as 2- trimethylaminolauric acid, and compounds of any of the previously mentioned types but in which the nitrogen atom is replaced by phosphorus.
  • a long chain fatty acid e.g. of 10 to 20 carbon atoms
  • diethylene triamine and monohalocarboxylic acids having 2 to 6 carbon atoms e.g. l-coco 5 hydroxethyl-5-carboxymethylimidazoline
  • the detergent composition may further contain one or more water-soluble builder salts which may be either Organic or inorganic in nature. Suitable representatives include the following:
  • Mixtures of two or more inorganic or organic salts can be used, as can mixtures of inorganic and organic salts.
  • water-soluble, alkali metal polyphosphate builder salts are particularly preferred herein. These salts form watersoluble complexes with calcium and magnesium ions found in hard water and thereby prevent the formation of insoluble salts which tend to deposit upon textiles during a washing cycle. Further, such phosphates enhance the detersive efficiency of anionic detergents, aid in controlling sudsing and powers and aid in keeping soil suspended in the washing bath after its removal from the soiled textiles.
  • compositions of the invention may be included in compositions of the invention, whether in solid or liquid form, by addition in a known manner to the aqueous mixtures or to the solidified product.
  • higher fatty acid amides such as coconut or lauric monoethanolamide, isopropanolamide and the like
  • hydrotrop'ic solubilizing agents such as xylene or toluene sulfonates
  • organic solubilizing agents such as ethanol, ethylene glycol and hexylene glycol
  • sodium carboxymethylcellulose and polyvinyl alcohol antiredeposition agents optical and fluorescent brightener materials
  • coloring agents corrosion inhibiting agents; germicides; perfumes, bluing agents; and the like.
  • Preferred compositions advantageously contain a hydrophobic colloidal cellulosic soil-suspending agent which is soluble or dispersible in water also.
  • the joint use of the combination of the cellulosic compound and polyvinyl alcohol is particularly effective for soil-suspension properties during the washing of a variety of fabrics, including both cotton and synthetic fibers such as nylon, Dacron, and resin-treated cottons.
  • the mixtures are used preferably in a total amount of 0.1 to 2 percent by weight of the solids.
  • Preferred cellulosic compounds are the alkali metal salts of a carboxy lower alkyl cellulose having up to 3 carbons in the alkyl group, such as the sodium and potassium salt of carboxymethylcellulose. Suitable salts are sodium carboxyethylcellulose; the cellulose sulfates and lower alkyl and hydroxyalkylcellulose ethers such as methyl-, ethyl-, and hydroxyethylcellulose.
  • the proportions of such ingredients are not particularly critical and may be selected in accordance with usual practice.
  • the organic detergent may be employed in concentrations ranging from about 2% and preferably from about 10% to about 50% by weight of the composition.
  • the builder salts, whether organic or inorganic, are preferably employed in concentrations ranging from about 10% to about by weight of the composition.
  • Exemplary of bleaching formulations capable of providing the improvements described herein include a composition comprising sodium carbonate (5 parts), sodium tripolyphosphate (30 parts), ethyl chloroformate (15.5 parts), sodium perborate (22 parts), alkylbenzenesulfonate (2 parts), with the remainder comprising on a. parts basis sodium sulfate, brightener, perfume, chelating agent, etc.
  • the bleaching and detergent compositions of the present invention entail the further advantage that they may be effectively employed over a relatively wide pH range in the virtual absence of risk of damage to the fabric material.
  • the desired pH may be readily obtained by the addition of suitable buffering agents to the bleaching solution.
  • the effectiveness of the bleaching or detergent composition at relatively high pH permits their advantageous use in combination with common house hold laundry soaps and detergents for preventive bleaching of fiber materials. In any event, a pH within the range of from about 6-10 is recommended for the vast majority of bleaching and washing applications.
  • a process of bleaching textiles comprising the steps of placing the textiles to be bleached in an aqueous solution of water-soluble, inorganic peroxide bleaching agent and a water-soluble chloroforrnate selected from the group consisting of C -C alkyl and phenyl chloroformates wherein the chloroformate peroxide mole ratio ranges from about .01 to about 2.0, allowing the textiles to remain in the solution for a normal washing period and rinsing the textiles.

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  • 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)
US677745A 1967-10-24 1967-10-24 Process of bleaching textiles Expired - Lifetime US3589857A (en)

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US67774667A 1967-10-24 1967-10-24
US67774567A 1967-10-24 1967-10-24

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US (1) US3589857A (de)
BE (2) BE722742A (de)
CH (2) CH492066A (de)
DE (2) DE1802015A1 (de)
DK (2) DK129057A (de)
FR (2) FR1589886A (de)
GB (2) GB1242287A (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3986973A (en) * 1975-10-24 1976-10-19 American Cyanamid Company Cyanoformates and cyanoformamides as bleach activators
US4120809A (en) * 1973-07-24 1978-10-17 Colgate-Palmolive Company Washing and bleaching with composition containing bleach activator and a nitrilotricarboxylic acid compound
US5132036A (en) * 1989-08-23 1992-07-21 Lever Brothers Company, Division Of Conopco, Inc. Laundry treatment product
US20070200415A1 (en) * 2006-02-27 2007-08-30 Eberlein David C Seating unit with adjustable components

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4110074A (en) * 1977-10-03 1978-08-29 Fmc Corporation Mixed carboxylic/sulfonic anhydrides in peroxygen bleaching
US4120651A (en) 1977-10-03 1978-10-17 Fmc Corporation Disulfones as peroxygen activators
US4215003A (en) 1978-11-20 1980-07-29 Fmc Corporation Peroxygen bleaching and compositions therefor
US4212757A (en) 1978-12-22 1980-07-15 Fmc Corporation Peroxygen bleaching and compositions therefor
US4202786A (en) 1978-12-22 1980-05-13 Fmc Corporation Peroxygen bleaching and compositions therefor

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4120809A (en) * 1973-07-24 1978-10-17 Colgate-Palmolive Company Washing and bleaching with composition containing bleach activator and a nitrilotricarboxylic acid compound
US3986973A (en) * 1975-10-24 1976-10-19 American Cyanamid Company Cyanoformates and cyanoformamides as bleach activators
US5132036A (en) * 1989-08-23 1992-07-21 Lever Brothers Company, Division Of Conopco, Inc. Laundry treatment product
US20070200415A1 (en) * 2006-02-27 2007-08-30 Eberlein David C Seating unit with adjustable components

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Publication number Publication date
DK129057A (de)
BE722740A (de) 1969-04-01
CH492067A (de) 1970-06-15
CH492066A (de) 1970-06-15
DE1802017A1 (de) 1969-05-08
GB1242106A (en) 1971-08-11
FR1589886A (de) 1970-04-06
FR1589888A (de) 1970-04-06
DK129056A (de)
BE722742A (de) 1969-04-01
DE1802015A1 (de) 1969-06-19
GB1242287A (en) 1971-08-11

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