US3033704A - Rendering fabric anti-static, soft, and microorganisms resistant - Google Patents

Rendering fabric anti-static, soft, and microorganisms resistant Download PDF

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Publication number
US3033704A
US3033704A US814149A US81414959A US3033704A US 3033704 A US3033704 A US 3033704A US 814149 A US814149 A US 814149A US 81414959 A US81414959 A US 81414959A US 3033704 A US3033704 A US 3033704A
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fabric
formulation
cationic surface
surface active
active agent
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US814149A
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Joseph C Sherrill
Warner M Linfield
Byron E Marsh
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Armour and Co
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Armour and Co
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Priority to US814149A priority Critical patent/US3033704A/en
Priority to FR827558A priority patent/FR1257409A/en
Priority to GB17588/60A priority patent/GB930333A/en
Priority to DEA34679A priority patent/DE1195265B/en
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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
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • 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
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic

Definitions

  • the fabric is impregnated with a mixture of at least one cationic surface active agent and at least one organomercurial germicide to render such fabric substantially anti-static and soft and at least partially free from microorganisms.
  • treatment of the fabrics is obtained in a laundering process in which a laundered fabric is contacted in a rinsing operation with an aqueous solution of a mixture of at least one cationic surface active agent and at least one organomercurial germicide to impregnate the fabric with at least a portion of the organomercurial and the cationic surface active agent, and in which the treated fabric is then at least substantially dehydrated.
  • the alkyl group represented by R in the above formulae may be a natural mixture thereof derived from tallow, soybean or coconut oil.
  • cationic surface active agents which include a greater number of the long-chain alkyl groups demonstrate better fabric softening properties, Whereas a greater number of short-chain alkyl groups included in the cationic surface active agent tends towards better germicidal activity. Accordingly, compounds having the Formula labove tend toward greater germicidal activity than those having the Formula 2 above, whereas compounds having the Formula 2 tend toward greater fabric-- softening action than those having the Formula 1 above.
  • cationic surface active agents having Formulae 1 and 2 above in which R represents an alkyl radical containing from 12 to 18 carbon atoms, wherein R is a benzyl radical, wherein R is a methyl radical, and wherein X is chloride.
  • organomercurial germicide may be employed in the treatment of this invention, better results are obtained with phenylmercuric compounds such asthe acetate, propionate, butyrate, chloride, bromide or iodide thereof.
  • fabrics after laundering, are immersed in a rinse water containing a mixture of at least one cationic surface active agent and at least one organomercurial germicide in which mixture the organomercurial is included in a ratio of from 1 to 10% by weight of the cationic surface active agent, and
  • the cationic surface agent is included in a ratio of from 0.03 to 0.3% by weight of the fabric.
  • the advantages of this invention may be obtained by employing from 1 to 10% of the organomercurial in combination with the cationic surface active agent, better results are obtained with a ratio of organomercurial of from 4 to 8% by weight of the cationic surface active agent.
  • a ratio of organomercurial of from 4 to 8% by weight of the cationic surface active agent.
  • Especially desirable for utilization in this invention is a mixture of about 5.5 to 6% by weight of the organomercurial in combination with the cationic surface active agent.
  • the ratio of cationic surface active agent to fabric employed in this invention may be from 0.03 to 0.3% by weight, better results are obtained at a ratio of 0.065 to 0.1 by weight of cationic surface active agent in contact with the fabric. Furthermore, it has been found that from 0.03 to 0.065% by weight of cationic surface.
  • active agent in combination with the fabric facilitates pressing operations by rendering the fabric easier to :handle
  • tactile softness is achieved especially at a ratio of 7 tained at a ratio of about 43 ppm. of organomercurial in combination with the fabric.
  • a mixture of at least one cationic surface active agent and at least one organomercurial germicide can be packaged in the aforementioned ratio to be employed in laundering plants by introduction into a rinse water at the hereinbefore described concentration. After the rinsing operation has been completed, the fabrics canbe separated from the bulk of the rinse water, and then subjected to dehydration.
  • Example I The following formulation has been employed in the treatment of this invention:
  • Concentration 1 This is a. cationic surface active agent having formula (3) above in which the alkyl radicals represented by R1 are derived from tallow, soybean or coconut fatty acids, in which R3 represents an alkyl radical containing less than 3 carbon atoms, and in which X represents methyl sulfate.
  • Arquad-S This is a cationic surface active agent having the formula (1) above in which the alhyl radical represented by R1 is derived from tallow fatty acids, in which R; and R3 represent methyl radicals, and in which X represents chloride.
  • the phcnylmcrcuric propionate is first wettcd and finely dispersed in the hexylene glycol so that no lumps remain. This dispersion is thoroughly mixed with melted Softener 2-132 which has been preheated to a temperature of about 140 to 150 F.
  • thercsulting mixture is added slowly, with agitation, to 1 the water and dye solution which has been heated to a temp eraturc of about 120 to 130 F.
  • a temp eraturc of about 120 to 130 F.
  • the viscosity of the mixture should be permitted to rise as high as the mixing equipment allows, and thereafter the viscosity is controlled by the addition to the mixture of small increments of the sodium sulfate.
  • the Arquad-S may be slowly added to the mixture at room temperature, whereupon a reduction in viscosity will be obtained.
  • the brightener and perfume are added to the mixture, and agitation thereof is continued until the mass has become homogeneous. However, prolonged agitation after addition to the mixture of the brightener is not desirable.
  • the batch should be processed through a colloid mill or homogenizer.
  • the foregoing sequence-of addition of the ingredients is important in that the prcmixing of the cationic surface active agents, namely the Softener 2-132 and the Arquad- S, results in a relatively high concentration of chloride ion in the acidic medium, and consequently agglomeration of the phenylmcrcuric propionate in the mixture, which agglomeration is difiicult to disperse.
  • the cationic surface active agents namely the Softener 2-132 and the Arquad- S
  • This formulation may be introduced into the rinse water on the basis of 12 fluid ounces per one hundred pounds of fabric. Accordingly, there will be obtained in the rinse water 0.111% of the cationic surface active agent in combination with the fabric. Also, there will be obtained with this formulation in the rinse water about 63 ppm. of phenylmercuric propionate in combination with the fabric.
  • Example II There may be employed in the rinsing process of this invention the formulation of Example I in which, instead of the mixture of Softener 2-132 and Arquad-S specified in the formulation thereof, 20% of Softener 2-132 is utilized. Accordingly, there will be provided in the formulation 15% of active Softener2-132.
  • Example III There may be employed in the rinsing process of this invention the formulation of Example I in which, instead of the mixture of Softener 2-132 and Arquad-S, 20% of A-rquad 2HT (75%) is substituted. Accordingly, the formulation will include 15% of active Arquad 2HT.
  • Arquad 2HT is a cationic surface active agent having the Formula 2 above in which the alkyl radicals represented by R are derived from partially hydrogenated tallow fatty acids, in which. R and R represent methyl radicals and in which X is chloride.
  • Example IV There may be employed in the rinsing process of this invention the formulation of Example I in which, instead of phcnylmercuric propionatc, 0.85% of phenylmcrcuric acetate is substituted.
  • Example V There may be employed in the rinsing process of this invention the formulation of Example I in which, instead of the mixture of Softener 2-132 and Arquad-S, a mixture of 13.40% of Arquad ZHT (75%) and 10.00% of Arquad-S is substituted. Accordingly, there will be included in the formulation 10.0% of active Arquad' 2HT and 5.0% of active Arquad-S.
  • Example VI There may be employed-in the rinsing process of this invention the formulation of Example I in which, instead of the Softener 2-132 and Arquad-S and phenylmercuric propionatc, 13.40% of Arquad 2HT and 10.00% of Arquad-S and 0.85 of phcnylmcrcuric acetate is substituted. Accordingly, there will be included in the formulation 10.0% of active Arquad 2HT and 5.0% of active Arqua'd-S.
  • Example VII There may be employed in the rinsing process of this invention the formulation of Example I in which, instead of Softener 2-132, 10.0% active of a cationic surface active agent having FormulaZ above in which the alkyl radicals represented by R contain 12 carbon atoms, in which R and R represent methyl radicals, and in which X represents chloride. Also, instead of phenylmercun'c propionate, 0.85% phenylmercuric chloride is substituted. The pH of the formulation is adjusted to an alkaline level with an alkaline salt or an alkali. Accordingly, there will be included in the formulation 10.0% active of the above described cationic agent and 5.0% active Arquad-S.
  • Example IX There may be employed in the rinsing process of this invention the formulation of Example I in which, instead of a mixture of Softener 2-132 and Arquad-S, 10.0% active of a cationic agent having Formula 3 above in which R is an alkyl radical containing 12 carbon atoms, in which R is a methyl radical, and in which X represents chloride, 5.0% active of a cationic agent having Formula 1 above with the substitution therein being the same as for Arquad-S with the exception that X represents chloride instead of'mothyl sulfate. Also 0.85% phenylmercuric butyrate is substituted for the phenylmcrcuric propionate specified in the formula of Example I.
  • Example X There may be employed in the rinsing process of this invention the formulation of Example I in which is substituted, instead of a mixture of Softener 2-132 and Arquad-S, 15 active of a cationic agent having the Formula 3 above in which R represents alkyl radicals derived from tallow, soybean or coconut fatty acids, in which R is a benzyl radical, and in which X represents chloride, is substituted.
  • Example XI There may be employed in the rinsing process of this invention the formulation of Example I in which is substituted, instead of a mixture of Softener 2-132 and Arquad-S, 15% active of a cationic agent having the Formula 3 above in which R represents alkyl radicals containing 22 carbon atoms, in which R represents a methyl radical, and in which X represents phenylsulfonate or benzylsulfonate.
  • Example XII There may be employed in the rinsing process of this invention the formulation of Example I in which is substituted, instead of a mixture of Softener 2-132 and Arquad-S, 15% active of a cationic agent having the Formula 3 above in which R is an alkyl radical containing carbon atoms, in which R represents a methyl radical and in which X represents phenylsulfonate or benzylsulfonate. Also, there is substituted for the phenylmermuric propionate therein, 0.85% of phenylmercuric butyrate.
  • Example XIII There may be employed in the rinsing process of this invention the formulation of Example I in which is substituted, instead of a mixture of Softener 2-132 and Arquad-S, active of a cationic agent having the Formula 1 above in which R is an alkyl radical containing 10 to 22 carbon atoms derived from tallow, soybean or coconut fatty acids, in which R represents a benzyl radical, in which R is a methyl radical, and in which X represents a chloride ion. Also, instead of phenylmercuric propionate, 0.85 of phenylmercuric acetate is substitutcd.
  • Example XIV There may be employed in the rinsing process of this invention the formulation of Example I in which is substituted, instead of a mixture of Softener 2-132 and Arquad-S, 13.40% of Arquad 2HT (75%) and 5.0% active of a cationic agent having the formula 2% HG OH I I] HG CH wherein R is an alkyl radical containing 12 carbon atoms and wherein X represents chloride or bromide. Accordingly, the formulation will include 10.0% of active Arquad 2HT and 5.0% of active alkyl pyridinium halide described above.
  • Example XV There may be employed in the rinsing process of this invention the formulation of Example I in which is substituted, instead of Arquad-S and phenylmercuric propionate, 5.0% active of a cationic agent having the formula of Example XIII wherein R1 is an alkyl radical having 18 carbon atoms and wherein X represents a chloride or bromide anion and 0.85% phenylmercuric butyrate. Accordingly, the formulation will include 10.0% of active Softener 2-132 and 5.0% of active alkyl pyridinium halide described above.
  • Example XVI There may be employed in the rinsing process of this invention the formulation of Example I in which is substituted, instead of .a mixture of Softener 2-132 and Arquad-S, 15.0% active of a cationic agent having the formula wherein R is an alkyl radical containing 10 carbon atoms, wherein R is an ethanol radical, wherein R is a methyl radical, and wherein X represents methyl sulfate. Also, instead of phenylmercuric propionate, phenylmercuric acetate is substituted.
  • Example XVII There may be employed in the rinsing process of this invention the formulation of Example I in which is substituted, instead of a mixture of Softener 2-132 and Arquad-S and phenylmercuric propionate, 15.0% active of a cationic agent having the formula of Example XVI wherein R is an alkyl radical containing 22 carbon atoms, wherein R is an ethanol radical, wherein R is a methyl radical, and wherein X is phenyl sulfonate or benzyl sulfonate, and 0.85% phenylmercuric butyrate.
  • a cationic agent having the formula of Example XVI wherein R is an alkyl radical containing 22 carbon atoms, wherein R is an ethanol radical, wherein R is a methyl radical, and wherein X is phenyl sulfonate or benzyl sulfonate, and 0.85% phenylmercuric butyrate.
  • Example XVIII Example XIX There may be employed in the rinsing process of this invention the formulation of Example I in which is substituted, instead of Softener 2-132 and Arquad-S and phenylmercuric propionate, 13.4% of Arquad 2HT and 5.0% active of a cationic agent of the type Hyamine 1622 (Rohm and Haas) and 0.85% phenylmercuric acetate. Accordingly, the formulation will include of active Arquad 2HT and 5.0% of active Hyamine 1622.
  • Example XX There may be employed in the rinsing process of this invention the formulation of Example I in which is substituted, instead of Arquad-S, 5.0% active of a cationic agent of the type Emcol E-607.
  • Example XXI There may be employed in the rinsing process of this invention the formulation of Example I in which is substituted, instead of Softener 2-132 and Arquad-S and phenylmercuric propionate, 13.40% of Arquad 2HT (75 and 5.0% active of a cationic agent of the type Emcol E-ll and 0.85% phenylmercuric acetate. Accordingly, the formulation will include 10.0% of active Arquad 2HT and 5.0% of active Emcol E-ll.
  • Example XXII There may be employed in the rinsing process of this invention the formulation of Example I in which is substituted, instead of Arquad-S, 5% active of a cationic agent of the type Emcol E-ll. Accordingly, the formulation will include 10.0% of active Softener 2-132 and 5.0% of active Emcol E-ll.
  • Example XXIII There may be employed in the rinsing process of this invention the formulation of Example 1, except that 0.36 instead of 0.8% phenylmercuric propionate is used. This formulation is utilized in the rinsing process on the basis of liquid ounces per one hundred pounds of fabric. Accordingly there will be obtained in the rinse water 0.03% of the cationic surface active agent in combination with the fabric. Also, there will be obtained with this formulation in the rinse water about 7 ppm. of phenylmercuric propionate in combination with the fabric.
  • Example XXIV There may be employed in the rinsing process of this invention the formulation of Example XXII, except that 32 /2 fluid ounces are used per 100 pounds of fabric. Accordingly there will be obtained in the rinse water 0.3% of the cationic surface active agent in combination with the fabric. Also, there will be obtained with this formulation in the rinse water about 70 p.p.m. phenylmercuric propionate in combination with the fabric.
  • Example XXV There may be employed in the rinsing process of this invention the formulation of Example 1, except that 0.15 instead of 0.85% phenylmercuric propionate is used. This formulation is used on the basis of 7 /2 fluid ounces per one himdred pounds of fabric. Accordingly there will be obtained in the rinse water 0.07% of the cationic surface active agent in combination with the fabric. Also, there will be obtained with this formulation in the rinse water about 7 ppm. of phenylrnercuric propionate in combination with the fabric.
  • Example XXVI There may be employed in the rinsing process of this invention the formulation of Example I, except that 1.5 instead of 0.85 phenylmercuric propionate is used. This formulation is used on the basis of 7 /2 fluid ounces per one hundred pounds of fabric. Accordingly there will be obtained in the rinse water 0.07 of the cationic surface active agent in combination with the fabric. Also there will be obtained with this formulation in the rinse water about 70 ppm. phenylmercuric propionate in combination with the fabric.
  • Example XX VII The enhanced impregnation of the fabric with the organomercurial, and the consequent increased antibacterial effect, obtained by the treatment of this invention, can be demonstrated as follows:
  • the cationic surface active agent quaternized imidazoline
  • phenylmercuric propionate was included in the rinse water at a concentration of 50 ppm. of the fabric.
  • the fabrics were first treated in rinse water with the cationic surface active agent, and, after draining the first rinse water, a second rinse water-containing the phenylmercuric propionate was contacted with the fabric.
  • the results were asfollows:
  • the evaluation of the treated fabric was obtained by introducing a portion of the fabric on seeded agar plates which were incubated at a temperature of 98.6 F. for a period of 24 hours.
  • the term zones of inhibition refers to the width in mm. of no-growth areas of agar surrounding the treated fabric.
  • phenylrnercuric propionate and phenylrnercuric acetate specified in the formulations of these examples, there may be employed as the organornercurial in this rinsing process phenylmercuric chloride, bromide, iodide and butyrate.
  • the FDA strain No. 209 of S. aureus is a standard microorganism employed in experimentation. It has been found that zones of inhibition against this organism in the order of 3-5 mm. results in a minimal effect against resistant strains of S. aureus, and that similar zones of inhibition represent minimal effects against ammonia-producing microorganisms. On the other hand, it has been shown that zones of inhibition in the order of 7-12 mm. indicate effectiveness against resistant strains of S. aureus. Consequently, it will be seen that the treatment of this invention results in the impregnation of the fabric with an amount of the organomercurial adequate to obtain inhibition of growth of resistant strains of S. aureus, whereas the treatment of the fabric with separate rinses of the cationic surface active agent and of the organomercurial provide impregnation of the fabric with the organomercurial in such concentration as to provide inhibition of these resistant strains.
  • a laundering and fabric-softening process the steps of rinsing a laundered fabric in an aqueous solution of a mixture of' at least one cationic surface active agent and at least one organornercurial germicide, said organomercurial germicide being included in said mixture in a ratio of from 1 to 10% by weight of said cationic surface active agent, and said cationic surface active agent being employed in a ratio of from 0.03 to 0.3% by weight of said fabric, to impregnate said fabric with at least a portion of said organomercurial germicide and said cationic surface active agent, and then at least substantially dehydrating said fabric.

Description

United States Patent Office 3,033,704 Patented May 8, 1 962 3,033,704 RENDERIN G FABRIC ANTI-STATIC, SOFT, AND
MICROURGANISMS RESlSTANT Joseph C. Sherrill, Park Forest, Warner M. Linfield,
Evanston, and Byron E. Marsh, Brookfield, III., assignors, by mesne assignments, toArmour and Company, Chicago, 11]., a corporation of Delaware No Drawing. Filed May 19, 1959, Ser. No. 814,149 3 Claims ((31. 11747) dering fabrics soft, anti-static and substantially lint-free by the treatment thereof with cationic surface active agents, the provision of fabrics also at least partially free from microorganisms in a laundering process has not as yet been satisfactorily obtained.
Accordingly, it is an object of this invention to provide .alaundering process in which a fabric is rendered substantially anti-static and lint-free and soft, while at the same time rendering the fabric at least partially free from microorganisms. Other advantages will become apparent as the specification proceeds.
In the special treatment of this invention the fabric is impregnated with a mixture of at least one cationic surface active agent and at least one organomercurial germicide to render such fabric substantially anti-static and soft and at least partially free from microorganisms.
In a preferred aspect of this invention, treatment of the fabrics is obtained in a laundering process in which a laundered fabric is contacted in a rinsing operation with an aqueous solution of a mixture of at least one cationic surface active agent and at least one organomercurial germicide to impregnate the fabric with at least a portion of the organomercurial and the cationic surface active agent, and in which the treated fabric is then at least substantially dehydrated.
.Although the advantages of this invention may be achieved with any cationic surface active agent, better results are obtained with a cationic surface active agent of the group having the formulae wherein R is an alkyl radical containing from 10 to 22 carbon atoms, wherein R represents a benzyl radical or an alkyl radical containing less than 3 carbon atoms, wherein R is an alkyl radical containing less than 3 carbon atoms, and wherein X represents an anion of the group consisting of chloride, bromide, sulfate and an alkyl sulfate in which the alkyl radical contains less than 5 carbon atoms. Furthermore, the alkyl group represented by R in the above formulae may be a natural mixture thereof derived from tallow, soybean or coconut oil. Also, it is known that cationic surface active agents which include a greater number of the long-chain alkyl groups demonstrate better fabric softening properties, Whereas a greater number of short-chain alkyl groups included in the cationic surface active agent tends towards better germicidal activity. Accordingly, compounds having the Formula labove tend toward greater germicidal activity than those having the Formula 2 above, whereas compounds having the Formula 2 tend toward greater fabric-- softening action than those having the Formula 1 above. Even better results may be obtained with cationic surface active agents having Formulae 1 and 2 above in which R represents an alkyl radical containing from 12 to 18 carbon atoms, wherein R is a benzyl radical, wherein R is a methyl radical, and wherein X is chloride.
Although any organomercurial germicide may be employed in the treatment of this invention, better results are obtained with phenylmercuric compounds such asthe acetate, propionate, butyrate, chloride, bromide or iodide thereof. 1
In the preferred practice of this invention fabrics, after laundering, are immersed in a rinse water containing a mixture of at least one cationic surface active agent and at least one organomercurial germicide in which mixture the organomercurial is included in a ratio of from 1 to 10% by weight of the cationic surface active agent, and
in which the cationic surface agent is included in a ratio of from 0.03 to 0.3% by weight of the fabric. After the fabric has been impregnated with at least a portion of the mixture of the organomercurial and the cationic surface active agent, the fabric is at least substantially dehydrated.
Although the advantages of this invention may be obtained by employing from 1 to 10% of the organomercurial in combination with the cationic surface active agent, better results are obtained with a ratio of organomercurial of from 4 to 8% by weight of the cationic surface active agent. Especially desirable for utilization in this invention is a mixture of about 5.5 to 6% by weight of the organomercurial in combination with the cationic surface active agent.
'Although the ratio of cationic surface active agent to fabric employed in this invention may be from 0.03 to 0.3% by weight, better results are obtained at a ratio of 0.065 to 0.1 by weight of cationic surface active agent in contact with the fabric. Furthermore, it has been found that from 0.03 to 0.065% by weight of cationic surface.
active agent in combination with the fabric facilitates pressing operations by rendering the fabric easier to :handle,
whereas tactile softness is achieved especially at a ratio of 7 tained at a ratio of about 43 ppm. of organomercurial in combination with the fabric.
It is anticipated that a mixture of at least one cationic surface active agent and at least one organomercurial germicide can be packaged in the aforementioned ratio to be employed in laundering plants by introduction into a rinse water at the hereinbefore described concentration. After the rinsing operation has been completed, the fabrics canbe separated from the bulk of the rinse water, and then subjected to dehydration.
This invention is further illustrated in the following specific examples:
Example I The following formulation has been employed in the treatment of this invention:
Concentration 1 This is a. cationic surface active agent having formula (3) above in which the alkyl radicals represented by R1 are derived from tallow, soybean or coconut fatty acids, in which R3 represents an alkyl radical containing less than 3 carbon atoms, and in which X represents methyl sulfate.
Arquad-S. This is a cationic surface active agent having the formula (1) above in which the alhyl radical represented by R1 is derived from tallow fatty acids, in which R; and R3 represent methyl radicals, and in which X represents chloride.
3 This is a dye of the pigment group.
This is an optical brightener of the arylimidazole type.
Any perfume may be employed in this type of formulation, which perfumes are well-known and widely used.
In preparing this formulation, the phcnylmcrcuric propionate is first wettcd and finely dispersed in the hexylene glycol so that no lumps remain. This dispersion is thoroughly mixed with melted Softener 2-132 which has been preheated to a temperature of about 140 to 150 F.
thercsulting mixture is added slowly, with agitation, to 1 the water and dye solution which has been heated to a temp eraturc of about 120 to 130 F. As the melted softenerorganomercurial dispersion is added to the solution the viscosity of the mix will increase gradually due to gel formation. The viscosity of the mixture should be permitted to rise as high as the mixing equipment allows, and thereafter the viscosity is controlled by the addition to the mixture of small increments of the sodium sulfate. After the batch has been uniformly blended, the Arquad-S may be slowly added to the mixture at room temperature, whereupon a reduction in viscosity will be obtained. Thereafter the brightener and perfume are added to the mixture, and agitation thereof is continued until the mass has become homogeneous. However, prolonged agitation after addition to the mixture of the brightener is not desirable. After the mixing has been completed, the batch should be processed through a colloid mill or homogenizer.
The foregoing sequence-of addition of the ingredients is important in that the prcmixing of the cationic surface active agents, namely the Softener 2-132 and the Arquad- S, results in a relatively high concentration of chloride ion in the acidic medium, and consequently agglomeration of the phenylmcrcuric propionate in the mixture, which agglomeration is difiicult to disperse.
This formulation may be introduced into the rinse water on the basis of 12 fluid ounces per one hundred pounds of fabric. Accordingly, there will be obtained in the rinse water 0.111% of the cationic surface active agent in combination with the fabric. Also, there will be obtained with this formulation in the rinse water about 63 ppm. of phenylmercuric propionate in combination with the fabric.
Example II There may be employed in the rinsing process of this invention the formulation of Example I in which, instead of the mixture of Softener 2-132 and Arquad-S specified in the formulation thereof, 20% of Softener 2-132 is utilized. Accordingly, there will be provided in the formulation 15% of active Softener2-132.
4 Example III There may be employed in the rinsing process of this invention the formulation of Example I in which, instead of the mixture of Softener 2-132 and Arquad-S, 20% of A-rquad 2HT (75%) is substituted. Accordingly, the formulation will include 15% of active Arquad 2HT. Arquad 2HT is a cationic surface active agent having the Formula 2 above in which the alkyl radicals represented by R are derived from partially hydrogenated tallow fatty acids, in which. R and R represent methyl radicals and in which X is chloride.
Example IV There may be employed in the rinsing process of this invention the formulation of Example I in which, instead of phcnylmercuric propionatc, 0.85% of phenylmcrcuric acetate is substituted.
Example V There may be employed in the rinsing process of this invention the formulation of Example I in which, instead of the mixture of Softener 2-132 and Arquad-S, a mixture of 13.40% of Arquad ZHT (75%) and 10.00% of Arquad-S is substituted. Accordingly, there will be included in the formulation 10.0% of active Arquad' 2HT and 5.0% of active Arquad-S.
Example VI There may be employed-in the rinsing process of this invention the formulation of Example I in which, instead of the Softener 2-132 and Arquad-S and phenylmercuric propionatc, 13.40% of Arquad 2HT and 10.00% of Arquad-S and 0.85 of phcnylmcrcuric acetate is substituted. Accordingly, there will be included in the formulation 10.0% of active Arquad 2HT and 5.0% of active Arqua'd-S.
Example VII Example VIII There may be employed in the rinsing process of this invention the formulation of Example I in which, instead of Softener 2-132, 10.0% active of a cationic surface active agent having FormulaZ above in which the alkyl radicals represented by R contain 12 carbon atoms, in which R and R represent methyl radicals, and in which X represents chloride. Also, instead of phenylmercun'c propionate, 0.85% phenylmercuric chloride is substituted. The pH of the formulation is adjusted to an alkaline level with an alkaline salt or an alkali. Accordingly, there will be included in the formulation 10.0% active of the above described cationic agent and 5.0% active Arquad-S.
Example IX There may be employed in the rinsing process of this invention the formulation of Example I in which, instead of a mixture of Softener 2-132 and Arquad-S, 10.0% active of a cationic agent having Formula 3 above in which R is an alkyl radical containing 12 carbon atoms, in which R is a methyl radical, and in which X represents chloride, 5.0% active of a cationic agent having Formula 1 above with the substitution therein being the same as for Arquad-S with the exception that X represents chloride instead of'mothyl sulfate. Also 0.85% phenylmercuric butyrate is substituted for the phenylmcrcuric propionate specified in the formula of Example I.
Example X There may be employed in the rinsing process of this invention the formulation of Example I in which is substituted, instead of a mixture of Softener 2-132 and Arquad-S, 15 active of a cationic agent having the Formula 3 above in which R represents alkyl radicals derived from tallow, soybean or coconut fatty acids, in which R is a benzyl radical, and in which X represents chloride, is substituted.
Example XI There may be employed in the rinsing process of this invention the formulation of Example I in which is substituted, instead of a mixture of Softener 2-132 and Arquad-S, 15% active of a cationic agent having the Formula 3 above in which R represents alkyl radicals containing 22 carbon atoms, in which R represents a methyl radical, and in which X represents phenylsulfonate or benzylsulfonate.
Example XII There may be employed in the rinsing process of this invention the formulation of Example I in which is substituted, instead of a mixture of Softener 2-132 and Arquad-S, 15% active of a cationic agent having the Formula 3 above in which R is an alkyl radical containing carbon atoms, in which R represents a methyl radical and in which X represents phenylsulfonate or benzylsulfonate. Also, there is substituted for the phenylmermuric propionate therein, 0.85% of phenylmercuric butyrate.
-- Example XIII There may be employed in the rinsing process of this invention the formulation of Example I in which is substituted, instead of a mixture of Softener 2-132 and Arquad-S, active of a cationic agent having the Formula 1 above in which R is an alkyl radical containing 10 to 22 carbon atoms derived from tallow, soybean or coconut fatty acids, in which R represents a benzyl radical, in which R is a methyl radical, and in which X represents a chloride ion. Also, instead of phenylmercuric propionate, 0.85 of phenylmercuric acetate is substitutcd.
Example XIV There may be employed in the rinsing process of this invention the formulation of Example I in which is substituted, instead of a mixture of Softener 2-132 and Arquad-S, 13.40% of Arquad 2HT (75%) and 5.0% active of a cationic agent having the formula 2% HG OH I I] HG CH wherein R is an alkyl radical containing 12 carbon atoms and wherein X represents chloride or bromide. Accordingly, the formulation will include 10.0% of active Arquad 2HT and 5.0% of active alkyl pyridinium halide described above.
Example XV There may be employed in the rinsing process of this invention the formulation of Example I in which is substituted, instead of Arquad-S and phenylmercuric propionate, 5.0% active of a cationic agent having the formula of Example XIII wherein R1 is an alkyl radical having 18 carbon atoms and wherein X represents a chloride or bromide anion and 0.85% phenylmercuric butyrate. Accordingly, the formulation will include 10.0% of active Softener 2-132 and 5.0% of active alkyl pyridinium halide described above.
6 Example XVI There may be employed in the rinsing process of this invention the formulation of Example I in which is substituted, instead of .a mixture of Softener 2-132 and Arquad-S, 15.0% active of a cationic agent having the formula wherein R is an alkyl radical containing 10 carbon atoms, wherein R is an ethanol radical, wherein R is a methyl radical, and wherein X represents methyl sulfate. Also, instead of phenylmercuric propionate, phenylmercuric acetate is substituted.
Example XVII There may be employed in the rinsing process of this invention the formulation of Example I in which is substituted, instead of a mixture of Softener 2-132 and Arquad-S and phenylmercuric propionate, 15.0% active of a cationic agent having the formula of Example XVI wherein R is an alkyl radical containing 22 carbon atoms, wherein R is an ethanol radical, wherein R is a methyl radical, and wherein X is phenyl sulfonate or benzyl sulfonate, and 0.85% phenylmercuric butyrate.
Example XVIII Example XIX There may be employed in the rinsing process of this invention the formulation of Example I in which is substituted, instead of Softener 2-132 and Arquad-S and phenylmercuric propionate, 13.4% of Arquad 2HT and 5.0% active of a cationic agent of the type Hyamine 1622 (Rohm and Haas) and 0.85% phenylmercuric acetate. Accordingly, the formulation will include of active Arquad 2HT and 5.0% of active Hyamine 1622.
Example XX There may be employed in the rinsing process of this invention the formulation of Example I in which is substituted, instead of Arquad-S, 5.0% active of a cationic agent of the type Emcol E-607.
Example XXI There may be employed in the rinsing process of this invention the formulation of Example I in which is substituted, instead of Softener 2-132 and Arquad-S and phenylmercuric propionate, 13.40% of Arquad 2HT (75 and 5.0% active of a cationic agent of the type Emcol E-ll and 0.85% phenylmercuric acetate. Accordingly, the formulation will include 10.0% of active Arquad 2HT and 5.0% of active Emcol E-ll.
Example XXII There may be employed in the rinsing process of this invention the formulation of Example I in which is substituted, instead of Arquad-S, 5% active of a cationic agent of the type Emcol E-ll. Accordingly, the formulation will include 10.0% of active Softener 2-132 and 5.0% of active Emcol E-ll.
Example XXIII There may be employed in the rinsing process of this invention the formulation of Example 1, except that 0.36 instead of 0.8% phenylmercuric propionate is used. This formulation is utilized in the rinsing process on the basis of liquid ounces per one hundred pounds of fabric. Accordingly there will be obtained in the rinse water 0.03% of the cationic surface active agent in combination with the fabric. Also, there will be obtained with this formulation in the rinse water about 7 ppm. of phenylmercuric propionate in combination with the fabric.
Example XXIV There may be employed in the rinsing process of this invention the formulation of Example XXII, except that 32 /2 fluid ounces are used per 100 pounds of fabric. Accordingly there will be obtained in the rinse water 0.3% of the cationic surface active agent in combination with the fabric. Also, there will be obtained with this formulation in the rinse water about 70 p.p.m. phenylmercuric propionate in combination with the fabric.
Example XXV There may be employed in the rinsing process of this invention the formulation of Example 1, except that 0.15 instead of 0.85% phenylmercuric propionate is used. This formulation is used on the basis of 7 /2 fluid ounces per one himdred pounds of fabric. Accordingly there will be obtained in the rinse water 0.07% of the cationic surface active agent in combination with the fabric. Also, there will be obtained with this formulation in the rinse water about 7 ppm. of phenylrnercuric propionate in combination with the fabric.
Example XXVI There may be employed in the rinsing process of this invention the formulation of Example I, except that 1.5 instead of 0.85 phenylmercuric propionate is used. This formulation is used on the basis of 7 /2 fluid ounces per one hundred pounds of fabric. Accordingly there will be obtained in the rinse water 0.07 of the cationic surface active agent in combination with the fabric. Also there will be obtained with this formulation in the rinse water about 70 ppm. phenylmercuric propionate in combination with the fabric.
Example XX VII The enhanced impregnation of the fabric with the organomercurial, and the consequent increased antibacterial effect, obtained by the treatment of this invention, can be demonstrated as follows:
In this comparison, the cationic surface active agent, quaternized imidazoline, was included in a rinse water at a ratio of 0.079% by weight of the fabrics, while phenylmercuric propionate was included in the rinse water at a concentration of 50 ppm. of the fabric.
In one process of this comparison, the fabrics were first treated in rinse water with the cationic surface active agent, and, after draining the first rinse water, a second rinse water-containing the phenylmercuric propionate was contacted with the fabric. The results were asfollows:
Concentrations, Staphylococcus aureus OVVF 1 (FDA Strain No. 209), zones of inhibition (mm.) Cationic Mercurial (percent) (p.p.rn.)
1 2 3 4 Avg.
Experiment 1a 0.079 50 5 4 1 3 3 Experiment 0.079 50 5 4 1 5 4 1 0n weight of fabric.
Ina second process, a mixture of the cationic surface active agent and the phenylmercuric propionate was in- 8 2 troduced into a single rinse water which was contacted with the fabrics. The results were as follows:
1 0n weight of fabric.
In the foregoing, the evaluation of the treated fabric was obtained by introducing a portion of the fabric on seeded agar plates which were incubated at a temperature of 98.6 F. for a period of 24 hours. The term zones of inhibition refers to the width in mm. of no-growth areas of agar surrounding the treated fabric.
These results indicate that a greateramount of phenylmercuric propionate is impregnated in the fabric when a mixture of the phenylmercuric propionate and the cationic surface active agent is contacted with the fabric in comparison with the treatment of the fabric with sep arate rinses of the cationic surface active agent and of the phenylmercuric propionate, and consequently that a greater anti-bacterial effect is thereby obtained.
Instead of the phenylrnercuric propionate and phenylrnercuric acetate specified in the formulations of these examples, there may be employed as the organornercurial in this rinsing process phenylmercuric chloride, bromide, iodide and butyrate.
The FDA strain No. 209 of S. aureus is a standard microorganism employed in experimentation. It has been found that zones of inhibition against this organism in the order of 3-5 mm. results in a minimal effect against resistant strains of S. aureus, and that similar zones of inhibition represent minimal effects against ammonia-producing microorganisms. On the other hand, it has been shown that zones of inhibition in the order of 7-12 mm. indicate effectiveness against resistant strains of S. aureus. Consequently, it will be seen that the treatment of this invention results in the impregnation of the fabric with an amount of the organomercurial adequate to obtain inhibition of growth of resistant strains of S. aureus, whereas the treatment of the fabric with separate rinses of the cationic surface active agent and of the organomercurial provide impregnation of the fabric with the organomercurial in such concentration as to provide inhibition of these resistant strains.
While in the foregoing specification various embodiments of this invention have been illustrated in considerable detail for the purpose of illustration, it will be apparent to those skilled in the art that this invention is susceptible to other embodiments and that many of these details can be varied widely without departing from the basic concept and spirit of the invention.
We claim:
1. In a laundering and fabric-softening process, the steps of rinsing a laundered fabric in an aqueous solution of a mixture of' at least one cationic surface active agent and at least one organornercurial germicide, said organomercurial germicide being included in said mixture in a ratio of from 1 to 10% by weight of said cationic surface active agent, and said cationic surface active agent being employed in a ratio of from 0.03 to 0.3% by weight of said fabric, to impregnate said fabric with at least a portion of said organomercurial germicide and said cationic surface active agent, and then at least substantially dehydrating said fabric.
2. In a laundering process for softening fabrics, the steps of rinsing a laundered fabric in an aqueous solution of a mixture of at least one phenylmercuric com gound and at least one cationic surface active agent selected from the group having the formula wherein R represents an alkyl radical containing from 10 to 22 carbon atoms, wherein R is selected from the group consisting of a benzyl radical and an alkyl radical containing less than 3 carbon atoms, wherein R represents an alkyl radical containing less than 3 canbon atoms and wherein X is an anion selected from the group consisting of chloride, bromide, sulfate and an alkyl sulfate in which the alkyl radical contains less than 5 carbon atoms, said phenylmercuric compound being included in said mixture in a ratio of from 4 to 8% by weight of said cationic surface active agent, and said cationic surface active agent being employed in a ratio of'frorn 0.065 to 0.1% by weight of said fabric, to impregnate said fabric with at least a portion of said phenylmercuric compound and said cationic surface active agent, and then at least substantially dehydrating said fabric.
3. Treatment to render fabrics substantially anti-static and soft and at least partially free from microorganisms by rinsing a fabric in an aqueous solution containing at least one cationic surface active agent and at least one organomercurial germicide to impregnate the fabric with at least a portion of said cationic surfiace active agent and said organomercurial germicide, and then at least substantially dehydrating said fabric, said organomercurial germicide being employed in a ratio of from 1 to 10% by weight of said cationic surface-active agent.
References Cited in the file of this patent UNITED STATES PATENTS 2,423,261 'Sowa 4 July 1, 1947 2,536,750 Kamlet Jan. 2, 1951 2,734,830 I-Iagge etal l Feb. 14, 1956 2,898,262 Dietz Aug. 4, 1959 FOREIGN PATENTS 605,442 Great Britain July 23, 1948 132,125 Australia Apr. 11, 1949

Claims (1)

1. IN A LAUNDERING AND FABRIC-SOFTENING PROCESS, THE STEPS OF RINSING A LAUNDERED FABRIC IN AN AQUEOUS SOLUTION OF A MIXTURE OF AT LEAST ONE CATIONIC SURFACE ACTIVE AGENT AND AT LEAST ONE ORGANOMERCURIAL GERMICIDE, SAID ORGANOMERCURIAL GERMICIDE BEING INCLUDED IN SAID MIXTURE IN A RATIO OF FROM 1 TO 10% BY WEIGHT OF SAID CATIONIC SURFACE ACTIVE AGENT, AND SAID CATIONIC SURFACE ACTIVE AGENT BEING EMPLOYED IN A RATIO OF FROM 0.03 TO 0.3% BY WEIGHT OF SAID FABRIC, TO IMPREGNATE SAID FABRIC WITH AT LEAST A PORTION OF SAID ORGANOMERCURIAL GERMICIDE AND SAID CATIONIC SURFACE ACTIVE AGENT, AND THEN AT LEAST SUBSTANTIALLY DEHYDRATING SAID FABRIC.
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FR827558A FR1257409A (en) 1959-05-19 1960-05-18 Laundering process
GB17588/60A GB930333A (en) 1959-05-19 1960-05-18 Improvements in and relating to the rendering of fabrics substantially anti-static and soft and at least partially free from micro-organisms
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US3314743A (en) * 1963-11-07 1967-04-18 Gagliardi Domenick Donald Processes for treatment of preformed articles of olefin polymers and resulting products
US3360470A (en) * 1963-05-28 1967-12-26 Colgate Palmolive Co Laundering compositions
US3379565A (en) * 1962-12-26 1968-04-23 Monsanto Co Process for applying anti-static finish to a textile material
US3442692A (en) * 1965-08-13 1969-05-06 Conrad J Gaiser Method of conditioning fabrics
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US3650667A (en) * 1969-02-26 1972-03-21 Steiner American Corp Laundry process for producing fabrics that are substantially free from bacteria and bacterial spores
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US3899616A (en) * 1973-11-09 1975-08-12 Frank A Simonelli Fungistatic fabric treatment
US3904533A (en) * 1963-07-16 1975-09-09 Lever Brothers Ltd Fabric conditioners
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US4304610A (en) * 1979-06-22 1981-12-08 S. C. Johnson & Son, Inc. Carpet cleaning method
US4529803A (en) * 1979-12-12 1985-07-16 The Dow Chemical Company Process for preparing imidazolinium compounds
US4895667A (en) * 1988-05-24 1990-01-23 The Dial Corporation Fabric treating compositions
US5643498A (en) * 1994-08-19 1997-07-01 Rhone-Poulenc Inc. Quaternary cationic surfactants having multiple hydrophobic and hydrophilic groups
US5789371A (en) * 1997-04-22 1998-08-04 Rhodia Inc. Amphoteric surfactants having multiple hydrophobic and hydrophilic groups
US6040288A (en) * 1997-02-21 2000-03-21 Rhodia Inc. Fabric color protection compositions and methods
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US20080312118A1 (en) * 2007-06-12 2008-12-18 Rhodia Inc. Hard surface cleaning composition with hydrophilizing agent and method for cleaning hard surfaces
US20080311055A1 (en) * 2007-06-12 2008-12-18 Rhodia Inc. Mono-, di- and polyol alkoxylate phosphate esters in oral care formulations and methods for using same
US20080312120A1 (en) * 2007-06-12 2008-12-18 Rhodia Inc. Detergent composition with hydrophilizing soil-release agent and methods for using same
US20090023618A1 (en) * 2007-07-20 2009-01-22 Rhodia Inc. Method for recovering crude oil from a subterranean formation
US7524800B2 (en) 2007-06-12 2009-04-28 Rhodia Inc. Mono-, di- and polyol phosphate esters in personal care formulations

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Cited By (39)

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US3227456A (en) * 1961-12-15 1966-01-04 Eric O Sonneman Golf ball coated with a surface active chemical agent
US3379565A (en) * 1962-12-26 1968-04-23 Monsanto Co Process for applying anti-static finish to a textile material
US3360470A (en) * 1963-05-28 1967-12-26 Colgate Palmolive Co Laundering compositions
US3904533A (en) * 1963-07-16 1975-09-09 Lever Brothers Ltd Fabric conditioners
US3314743A (en) * 1963-11-07 1967-04-18 Gagliardi Domenick Donald Processes for treatment of preformed articles of olefin polymers and resulting products
DE1297573B (en) * 1965-06-09 1969-06-19 Geigy Ag J R Use of an optical brightener and a hand-improving agent in one and the same bath
US3442692A (en) * 1965-08-13 1969-05-06 Conrad J Gaiser Method of conditioning fabrics
US3650667A (en) * 1969-02-26 1972-03-21 Steiner American Corp Laundry process for producing fabrics that are substantially free from bacteria and bacterial spores
US3887476A (en) * 1973-07-16 1975-06-03 Ashland Oil Inc Quaternary ammonium derivatives of bisimidazoline compounds for use as fabric softeners
US3954634A (en) * 1973-07-27 1976-05-04 S. C. Johnson & Son, Inc. Stable, low-viscosity fabric softener
US3899616A (en) * 1973-11-09 1975-08-12 Frank A Simonelli Fungistatic fabric treatment
US4304610A (en) * 1979-06-22 1981-12-08 S. C. Johnson & Son, Inc. Carpet cleaning method
US4529803A (en) * 1979-12-12 1985-07-16 The Dow Chemical Company Process for preparing imidazolinium compounds
US4895667A (en) * 1988-05-24 1990-01-23 The Dial Corporation Fabric treating compositions
US5643498A (en) * 1994-08-19 1997-07-01 Rhone-Poulenc Inc. Quaternary cationic surfactants having multiple hydrophobic and hydrophilic groups
US6121222A (en) * 1996-12-27 2000-09-19 Rhodia Inc. Anionic surfactants having multiple hydrophobic and hydrophilic groups
US6040288A (en) * 1997-02-21 2000-03-21 Rhodia Inc. Fabric color protection compositions and methods
US5789371A (en) * 1997-04-22 1998-08-04 Rhodia Inc. Amphoteric surfactants having multiple hydrophobic and hydrophilic groups
WO2001059052A1 (en) * 2000-02-08 2001-08-16 Unilever Plc Fabric conditioning compositions
US20030166486A1 (en) * 2000-02-08 2003-09-04 David Machin Fabric conditioning compositions
US20080028986A1 (en) * 2006-06-12 2008-02-07 Rhodia, Inc. Hydrophilized substrate and method for hydrophilizing a hydrophobic surface of a substrate
US8993506B2 (en) 2006-06-12 2015-03-31 Rhodia Operations Hydrophilized substrate and method for hydrophilizing a hydrophobic surface of a substrate
US7550419B2 (en) 2007-06-12 2009-06-23 Rhodia Inc. Mono-, di- and polyol alkoxylate phosphate esters in oral care formulations and methods for using same
US20090233837A1 (en) * 2007-06-12 2009-09-17 Rhodia Inc. Detergent composition with hydrophilizing soil-release agent and methods for using same
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US20080312118A1 (en) * 2007-06-12 2008-12-18 Rhodia Inc. Hard surface cleaning composition with hydrophilizing agent and method for cleaning hard surfaces
US7524808B2 (en) 2007-06-12 2009-04-28 Rhodia Inc. Hard surface cleaning composition with hydrophilizing agent and method for cleaning hard surfaces
US7524800B2 (en) 2007-06-12 2009-04-28 Rhodia Inc. Mono-, di- and polyol phosphate esters in personal care formulations
US20090124525A1 (en) * 2007-06-12 2009-05-14 Rhodia Inc. Hard surface cleaning composition with hydrophilizing agent and method for cleaning hard surfaces
US20080311055A1 (en) * 2007-06-12 2008-12-18 Rhodia Inc. Mono-, di- and polyol alkoxylate phosphate esters in oral care formulations and methods for using same
US7557072B2 (en) 2007-06-12 2009-07-07 Rhodia Inc. Detergent composition with hydrophilizing soil-release agent and methods for using same
US20080312120A1 (en) * 2007-06-12 2008-12-18 Rhodia Inc. Detergent composition with hydrophilizing soil-release agent and methods for using same
US8293699B2 (en) 2007-06-12 2012-10-23 Rhodia Operations Hard surface cleaning composition with hydrophilizing agent and method for cleaning hard surfaces
US7867963B2 (en) 2007-06-12 2011-01-11 Rhodia Inc. Mono-, di- and polyol phosphate esters in personal care formulations
US7919449B2 (en) 2007-06-12 2011-04-05 Rhodia Operations Detergent composition with hydrophilizing soil-release agent and methods for using same
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US7608571B2 (en) 2007-07-20 2009-10-27 Rhodia Inc. Method for recovering crude oil from a subterranean formation utilizing a polyphosphate ester
US20090023618A1 (en) * 2007-07-20 2009-01-22 Rhodia Inc. Method for recovering crude oil from a subterranean formation

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