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1, 2-substituted imidazolinium salt and treatment of cellulosic fibrous materials therewith

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US2874074A
US2874074A US58336656A US2874074A US 2874074 A US2874074 A US 2874074A US 58336656 A US58336656 A US 58336656A US 2874074 A US2874074 A US 2874074A
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Carl E Johnson
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NAT ALUMINATE CORP
NATIONAL ALUMINATE Corp
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS, OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/35Heterocyclic compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/06Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C07D233/08Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
    • C07D233/12Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D233/14Radicals substituted by oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/06Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C07D233/08Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
    • C07D233/12Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D233/16Radicals substituted by nitrogen atoms

Description

United States Patent 2,874,074 1,2-SUBSTITUTED 'IMIDAZOLINVIUM 1 SALT AND TREATMENT OF CELLULOSIC FIBROUS MATE-" RIALS THEREWITH Carl E. Johnson, Westch ester, IlL, assignor to National Aluminate Corporation, Chicago, III., a corporation of Delaware I i No Drawing. Application May -8, 1956 Serial N0. 583,366

21 Claims. 01'. 1175-1595 This invention relates to the chemical treatment of fibrous materials, such as textiles and paper, whereby useful properties are imparted thereto. Particularly, it relates to treating textiles with new chemical softening agents, lubricants and water repellent agents. In another embodiment the invention is concerned with new and valuable chemical compositions.

It is an object of the invention to provide new and useful softeners and lubricants for fibrous materials such as textiles and paper.

A further object is to provide textilesofteners which are relatively non-toxic and do not tend as yellow bleached fabrics. Other objects will appear hereinafter,

It has been found that fibrous materials when treated with a colloidally dispersible l,2-substitutedimidazolinium salt which contains at least two higher aliphatic hydrocarbon radicals, each having at-least ll carbon atoms,

have their texture rendered soft and luxurious to the touch. Textiles such as cotton fabrics impregnated with these compounds as a' rinse after washing are pleasingly soft and fiuify and give theappearance of being sun dried. The colloidally dispersible 1,2-substituted imidazolinium salts when added to the rinse water in small amounts after typical laundering operationsimpart a soft downy hand to the treated fabrics. Dosages in the rinse water can range from .00l% to 1% by weight to apreferred treatment range of .005 to. .01.% by weight.

It has been the experience of theart'that textile treatments must usually be water soluble to be effective. Water dispersible materials have beende'emed'imperfect for such operations as textile softening. Surprisingly, however, it has been discovered that while the water soluble imidazolinium salts were relatively ineffective as softeners and lubricants the colloidally dispersible 1,2-substituted imidazolinium salts gave superior-results when employed-i 50 2,874,074 r amed Feb. 17, 1959 where D represents a divalent, non-amino organic radical containing, less than25 carbon atoms, composed ,of

elements from thegroup consisting of C, I-I, O and N; D represents a divalent organic radical containing less than 25 carbon atoms, composed of elements from the group consisting of C, I -I, :Q and N, and containing at least one amino group; R is a member of the class consisting of hydrogen and aliphatic and cycloaliphatic hydrocarbon radicals (e. g., cyclopentyl, cyclohexyl); R is a member of I the group consisting of alkyl, substituted alkyl (e. g., hydroxyalkyl such as HQCH CH HOCH CH CH halo-alkyl such as .clCH CI-l BrCH CI-l cinnamyl,.etc.), with the proviso that at least' two ofthe radicals R and R contain at least'll carbon atoms in an aliphatic chain; A represents an'anion and is usually halide; Y and Z arehydro'gen or a lower alkyl group containing notmore than 6 carbon, atoms.

A preferred species} of compositions corresponding ,to

the type illustrated"inlFormula'lI above-has the structure:

wherein .R is a member ofthe class consisting of ali- 5 phatic' and vcycloaliphatic hydrocarbon radicals and R' is ber, preferably 1 to 3, hal represents halide and n is a member of the group consisting of alkyl, substituted alkyl and aralkyl radicals, with the proviso that at least two of the radicals R and R contain from 15 to 23 carbon atoms in an aliphatic chain,x is a small whole numan integer of 2 or more, preferably- 2 to 6.

Examples of the 'l,2'-'substituted imidazolines from which the imidazolinium compounds of the invention may be formed, are described inWilson U. S. Patents 2,267,965 and 2,355,837. The imidazolines are usually formed by'reactingan acid, andin the present instance preferably a fattyacid ofat least 12 carbon atoms, with air alkylene polyamine (e. g., ethylene diamine, 1,2-

propylene diamine) or a hydroxyalkyl alkylene polyamrn'ete. g., hydroxyethylethylene diamine) or a polyalkylene polyamine (e. g., diethylene triamine, triethylene tetramine,.or tetraethylene pentamine). Some of the more readily available and preferred materials for preparing the starting imidazolines are the various .fatty acids or mixtures of such acids as occur in various fats and oils and the polyamine compounds, diethylene triamine, tetraethylene pentamine and aminoethyl ethanolamine. Stearic acid and diethylene triamine when reacted to form 1-(2-aminoethy1)-2-heptadecyl imidazoline offers an excellent starting material. Another preferred irnidazoline is 1-(2-hydroxyethyl)-2-heptadecyl imidazoline.

The additional long chain alkyl groups may be conveniently attached to the substituted radical in the l-position of the preferred imidazolines by; acylation or esterification with a suitable acid of appropriate chain length. Thus, 1-(2-aminoethyl)-2-heptadecyl imidazoline may be reacted with stearic acid under basic conditions to produce 1-(Z-stearoylaminoethyl)-2-heptadecyl imidazoline, which is then quaternized with an alkylating agent, such as benzyl chloride, to produce the imidazolinium salt, 1-

(2-stearoylaminoethyl)-2-heptadecyl-1-benzyl imidazolinium chloride.

In another preferred embodiment, an imidazoline formed from stearic acid and ethylene diamine, e. g., 2- heptadecyl imidazoline, is acylated with capric acid and then alkylated with octadecyl chloride to produce 2-heptadecyl, l-decanoyl, l-octadecyl imidazolinium chloride.

Other illustrative compounds that are colloidally dispersible in aqueous media and are useful in the practice of the invention are:

(l) l (2 stearoxyethyl ethylstearate) 2 decyl-l-methyl imidazolinium chloride.

(2) 1 (N stearoylaminoethyl aminoethyl) 2 heptadcyl-l-ethyl imida zolinium bromide.

(3) 1 (2 hydroxyethyl) 2 heptadecyl 1 octadecyl imidazolinium bromide.

-' hepta- (4) 1 (2 palmitoylaminoethyl) 2 ethyl 1 hexadecyl imidazolinium chloride.

(S) 1 (2 palmitoylaminoethyl) 2 heptadecyl 1- hexadecyl imidazolinium chloride. (6) 1 (2 stearoylaminoethyl) 2 heptadecyl l- (2,3-hydroxypropane) imidazolinium chloride.

(7) 1 (2 stearoylaminoethyl) 2 heptadecyl 1- propyl imidazolinium' chloride.

(8) 1 (2 stearoxyethyl) 2 imidazolinium chloride.

In the above compounds the following alkylating agents were used in the preparation of the imidazolinium salts: (1) methyl chloride; (2) ethyl bromide; (3) octadecyl bromide; (4) hexadecyl chloride; (5) hexadecyl chloride; 6) l-chloro-2,3-dihydroxy propane; (7 propyl chloride; and (8) benzyl chloride.

Any anion form of the imidazolinium salt other than halide may be employed. Sulfates, nitrates, nitrites, phosphates and carbonates produce useful treating agents.

It is thus apparent that long chain alkyl groups may be introduced into the ll-substituted imidazoline by a number of methods and at several places in the molecule.

heptadecyl 1 benizyl Two interesting alkylating agents for the 1,2-substituted' imidazolines have the following structural formulae:

III i ll RO-CCH: halogen Boom-043E, halogen Formula III is prepared by esterifying an alcohol with a halo-acetic acid to produce an ester. In Formula IV, halogen-2,3-hydroxy propane, produced by hydrolyzing an epihalohydrin, is esterified by an acid. In each case' C I O l i R VII . VIII I +halwherein R, D. 'D',"Y and Z have the significance shown in Formulae I and II, R has the significance shown for R in Formulae III and IV and hal is a halide anion.

v Specific examples of classes of compounds that fall within the above are shown below:

wherein each R above is an alkyl 'group and at least two the R- radicals are saturated.

R's contain from to 23 carbon atoms, and hal is a halide anion. Y I v v In a more preferred embodiment of compositions useful in the invention the R attached to the 2-carbon atom of the 'imidazolinium ring is a saturated 17 carbon atom alkyl group and each other R a saturated l8carbon atom alkyl group. Especially useful compositions are provided when only two of the possible three or more higher aliphatic hydrocarbon groups are'long hydrocarbon chains; Thus the two compounds illustrated by the following structural formulae are highly suitable for use as textile softeners. 1 w I where R is an alltyl group containing from 15 to 23 carbon atoms.

In conducting numerous tests, it was found that the preferred speciesof colloidally dispersible 1,2-substituted imidazolinium salts contained only two saturated alkyl groups .havingfrom .15. to 23 carbonatoms.v The compositions prepared from fatty acids or alcohols. especi-. ally the saturated compounds, such as lauric acid, as well as the corresponding alcohols,. are extremely useful. Stearic acid or stearyl alcohol give-exceptionally good results.

In all of the foregoing chemical formulae one or more of the radicals R can also be an unsaturated hydrocarbon group. For example, at the'2-position the radical R can be the heptadecenyl radical which results when oleic acid is condensed with. ethylene diamine, hydroxyethylethylenediamine, diethylenetriamine, triethylenetetramine or tetraethylenepentarnine g to produce the imidazoline. Likewise, hydrocarbon radicals attached at the 1-position can be unsaturated' -Thus, allyl chloride and other unsaturated quaternizing halides can be usedins'tead of-the saturated 'quaternizinfgfagents pre- VioiIsIydes'cribedJ In general, however-{the best results are obtained when the aliphatic --In order to evaluate the compositions described above as textile softeners, the followingtest method-"was emploYed. The test specimenswere cotton .diapers and cotton wash cloths which were indelibly numbered in one corner for purposes of identification. A portable 4'-gallon, 1%- pound capacity washer' and spin drier was used-to treat from to 1 pound of fabrics The specimens were washed three minutes in 4 gallons of Chicago tap water containing 75 cc. 'of'*a commercial "anionic detergent. The water was drained and the test cloths spun dry for one minute. The washer was refilled with water to which had been added the treating chemicalifrom an isopropanol suspension thereof.- The rinse cycle was conducted for 3 minutes, the washer drained and the specimens again spin dried for 1 minute. Another similar rinse cycle was run on washed by untreated specimens for purposes of comparison. Both the treated and untreated specimens were felt by at least 12 persons who gave their hydrocarbon chains of 6 opinions as to whether a treated spe'cimenwas soft and fluffy or whether it was relatively rough to the feel. The results of these tests were listed below in Table I. In these tests the specimens were room dried before testing.

Table I Percent by weight- Percent of treatof persons Composition ment in whofound rinse softness water 4 1 .oor 1. 1-(2 stearoylamlnoethyl)-2-heptadecyl-l-benzyl -.05 r 100 imidazolinium chloride; .01 100 4 .1 100 0 0 f N-orn 01' 2 C17H35C\ I as CH OHrCHzOH 100 J V 0 o l i Cis M 3. 1-(2-hydroxyethyl)-2-heptadecyl-1-benzy1 imid- .001 0 azolinlum chloride 0. 1 3 Y .001 100 4. 1-(2-amlnoethyl)-2-heptadecyl-1-octadecy1 lmid- .05 100 azolinium chloride"-. 0. 01 103 Composition 3 was a water soluble compound and was ineffective in comparison with the other colloidally dispersible 1,2-substituted imidazolinium salts.

It is desirable to place the materials in a low molecular weight aliphatic alcohol such as isopropanol to prevent freezing during shipment. The higher dosages have the effect of making the fabrics treated soft and fiuffy even after several subsequent washings without treatment. When dosages of about .05% to 1% by weight are used inthe rinse operation, water repellency is imparted to the fabrics. If the user does not desire such an effect, treatments can be temporarily suspended or the dosagediminished until such effects are mitigated. f In'any event, simple experimentations can determine optimum concentrations. y

-- The compositions of: the invention are-relatively stable when-prepared in an alcohol or water suspension.

butinthe-event separation occurs after a lapse'of time, heating or fagitation will restore the suspension'to its original condition. Laboratory tests'haveishown fabrics treated in accordance with the invention will not yellow with ageor with repeated treatment. The compositions are safe for home use when employed in the concentrations suggested herein. r

The compositions of the invention are especially use ful in treating hydratable fibers and cloth or sheets in which such fibers predominate, especially cellulosefibers such as cotton or blends of fibers in whichcellulos e predominates. The invention is also applicable to the treat ment ofwood' fibers andcloth', glass fibers and cloth, and s'yntheticfibers and cloth made-therefromor madefrom blends of synthetic fibers and natural fibers, e. g., blends of Dacron (polyethyleneterephthalate) and wool, blends containing Orlon (acrylic fiber) and the like.

The treatment is especially advantageous where it is desired to overcome harshness. of feel or. to enhance softness to touch or to enhance water repellancy of cloth or paper. i i

In all the compositions shown,' the quaternization'of' the l',=2'substituted imidazolines'is shown tobe on the 1- nitrogen atom. This is believed tobe correct. If, how

ever; quaterniza'tion' occursat the 3-nitrogen atom suchis deemed an equivalency for'the purpose of the invention.

The invention is hereby claimedas follows;

1. .The method of treating cellulosic fibrous materials which comprises applying, thereto an aqueous dispersion of a colloidally dispersible 1,2-substituted imidazolinium salt which contains at least two and not more than three higher aliphatic hydrocarbon radicals each having at least 11 carbon atoms, one of which higher aliphatic hydrocarbon radicals is in the 2-position of the imidazoline ring and another of which is in at least one of the l-position of the imidazoline ring and the cation radical.

2. The method of softening cotton textiles which comprises applying thereto an aqueous dispersion of a colloidally dispersible 1,2-substituted imidazolinium salt which contains atleast two andnot higher than three higher aliphatic hydrocarbon radicals each having at least 11 carbon atoms, one of which higher aliphatic hydrocarbon radicals is in the 2-position of the imidazoline ring and another of which is in at least one of the 1-position of the imidazoline ring and the cation radical.

3. The method of softening textiles which comprises applying thereto an aqueous dispersion of a colloidally dispersible 1,2-substituted imidazolinium salt from the group consisting of wherein DR togetherrepresents an ester and D'R represents an amide in which R in each instance is the acid portion and in which D represents a divalent, non-amino organic radical containing less than 25 carbon atoms, composed of elements from the group consisting of C, H, O and N; D represents a divalent, organic radical containing less than 25 carbon atoms, composed of elements from the group consisting of C, H, O and N; R is a member of the class consisting of hydrogen and aliphatic and cycloaliphatic hydrocarbon radicals; R is a member ofthe group consisting of alkyl, substituted alkyl and aralkyl radicals, with the proviso that at least two of the radicals R and R contain at least 11 carbon atoms'in an aliphatic chain; A represents an anion, and Y and- Z are selected from the group consisting of hydrogen and a lower alkyl group containing not more than 6 carbon. atoms.

4. The method of claim 3 wherein the 1,2-substituted imidazolinium salt is applied to the textiles from an aqueous medium containing from .001% to 1% by weight of said 1,2-substituted imidazolinium salt.

-5. The, method of claim 3 wherein the textile is predominantly cotton.

6-. The method of softening textileswhich comprises applying thereto a colloidally dispersible 1,2-substituted imidazolinium salt having the formula ber of the group consisting .of alkyl, substituted alkyl and aralkyl radicals, with the proviso that at least two of textile is pre- 10. The method of softening textiles which comprises applying thereto a colloidally dispersible 1,2-substituted imidazolinium salt of the formula o 01110111011 I O wherein R is an alkyl group containingfrom 15 to 23 carbon atoms.

11. The method of softening textiles which comprises applying thereto a colloidally dispersible 1,2-substituted imidazolinium salt of the formula Y wherein R is an alkyl group of at least 11 carbon atoms.

12. A cellulosic fiber ofithe type used in textiles and paperimpregnated with aminor amount of a-colloidally dispersible 1,2-substituted imidazolinium salt which=contains at least two and not more thanthree higher aliphatic'hydrocarbon radicals eachlhaving at'leastll carbon atoms, one of which higher aliphatic hydrocarbon radicals in the 2-position of the imidazoline ring and anotherof which is in at leastone of the 1-positi0n of they imidazoline ring and the cation radical.

13. As a composition, a 1,2-substituted imidazolini-um salt from the group consisting of More wherein DR together represents an ester and D'R represents an amide in which R in each instance is the acid portion and in which D represents a divalent, non-amino organic radical containing less than 25 carbon atoms composed of elements from the group consisting of C, H, O and N; D represents a divalent organic radical containing less than 25 carbon atoms, composed of elements from the group consisting of C, H, O and N; R is a member of the class consisting of hydrogen and aliphatic and cycloaliphatic hydrocarbon radicals; R is an alkyl radical; A represents anion and Y and Z are selected from the group consisting of hydrogen and a lower alkyl group containing not more than 6 carbon atoms.

14. A composition of the formula wherein R is an alkyl group of at least 11 carbon atoms and hal represents halide.

15. A composition of the formula rs sv 16. A composition of the formula wherein R is an alkyl group of at least 11 carbon atoms.

17. A composition of the formula Y Ii). 18. Asa composition; a L2-substituted imidazolinium salt from the group consisting of I .,....B. -'fh and - H "Phalwherein DR together represents an ester and D'R represents an amide in which R in each instance is the acid portion and in which D represents a divalent non-amino organic radical containing at least 25 carbon atoms, composed of the elements from the group consisting of C, H, O and N; D represents a divalent organic radical containing less than 25 carbon atoms composed of elements from the group consisting of C, H, O and N; R is a member of the class consisting of hydrogen and aliphatic and cycloaliphatic hydrocarbon radicals; R is an alkyl radical; hal represents halide and Y and Z are selected from the group consisting of hydrogen and a'lower alkyl group containing not more than 6 carbon atoms.

19. A composition of the formula o 11- -o-d-n HOCH:

wherein R is an alkyl group containing from 15 to 23 carbon atoms.

20. A composition of the formula N-0H, R-C

N-CH2 wherein R is an alkyl group containing from 15 to 23 carbon atoms.

21. A composition of the formula wherein R is an alkyl group containing from 15 to 23 carbon atoms.

(References on following page) UNITED STATES-PATENTS-' l Wilson Dec. 30, 1941;; Wilson Aug. 15, 1944 Shonle Jan. 3, 1950 Weldon Nov. 17, 1953 Winsqr Jan. 10, 1956

Claims (1)

1. THE METHOD OF TREATING CELLULOSIC FIBROUS MATERIALS WHICH COMPRISES APPLYING THERETO AN AQUEOUS DISPERSION OF A COLLOIDALLY DISPERSIBLE 1,2-SUBSTITUED IMIDAZOLINIUM SALT WHICH CONTAINS AT LEAST TWO AND NOT MORE THAN THREE HIGHER ALIPHATIC HYDROCARBON RADICALS EACH HAVING AT LEAST 11 CARBON ATOMS, ONE OF WHICH HIGHER ALIPHATIC HYDROCARBON RADICALS IS IN THE 2-POSITION OF THE IMIDAZOLINE RING AND ANOTHER OF WHICH IS IN AT LEAST ONE OF THE 1-POSITION OF THE IMIDAZOLINE RING AND THE CATION RADICAL.
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US2995520A (en) * 1956-06-11 1961-08-08 Nalco Chemical Co Treatment of fibrous materials and compositions therefor
US3056705A (en) * 1958-06-19 1962-10-02 Owens Corning Fiberglass Corp Surface treated glass and similar fibers
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US3138610A (en) * 1961-03-10 1964-06-23 Gen Aniline & Film Corp Substituted imidazolines
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US3329560A (en) * 1961-11-29 1967-07-04 Basf Ag Quaternary vinylimidazolinium copolymer dispersions, methods of application of same to paper and sized paper thereof
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US4095941A (en) * 1974-10-04 1978-06-20 Hoechst Aktiengesellschaft Fiber preparation agents to produce a marked separating capability
US4210763A (en) * 1974-10-21 1980-07-01 Sandoz Ltd. Water-soluble acid addition or quaternary ammonium salts useful in eliminating or preventing the brightening effects of anionic optical brighteners
US4529803A (en) * 1979-12-12 1985-07-16 The Dow Chemical Company Process for preparing imidazolinium compounds
FR2583752A1 (en) * 1985-06-19 1986-12-26 Kao Corp Process for preparing compounds of 1,2-substituted imidazoline
US4954635A (en) * 1989-09-06 1990-09-04 The Procter & Gamble Company Process for preparing quaternized imidazoline fabric conditioning compounds
US5116520A (en) * 1989-09-06 1992-05-26 The Procter & Gamble Co. Fabric softening and anti-static compositions containing a quaternized di-substituted imidazoline ester fabric softening compound with a nonionic fabric softening compound
US5322640A (en) * 1993-06-01 1994-06-21 Nalco Chemical Company Water soluble corrosion inhibitors
US5730839A (en) * 1995-07-21 1998-03-24 Kimberly-Clark Worldwide, Inc. Method of creping tissue webs containing a softener using a closed creping pocket
US6040288A (en) * 1997-02-21 2000-03-21 Rhodia Inc. Fabric color protection compositions and methods
WO2008154633A2 (en) 2007-06-12 2008-12-18 Rhodia Inc. Detergent composition with hydrophilizing soil-release agent and methods for using same
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
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
US8895482B2 (en) 2011-08-05 2014-11-25 Smart Chemical Services, Lp Constraining pyrite activity in shale
US8993506B2 (en) 2006-06-12 2015-03-31 Rhodia Operations Hydrophilized substrate and method for hydrophilizing a hydrophobic surface of a substrate

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US8993506B2 (en) 2006-06-12 2015-03-31 Rhodia Operations Hydrophilized substrate and method for hydrophilizing a hydrophobic surface of a substrate
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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
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
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