WO1998041605A1 - Compositions pour conditionneur de tissus - Google Patents

Compositions pour conditionneur de tissus Download PDF

Info

Publication number
WO1998041605A1
WO1998041605A1 PCT/IB1998/000373 IB9800373W WO9841605A1 WO 1998041605 A1 WO1998041605 A1 WO 1998041605A1 IB 9800373 W IB9800373 W IB 9800373W WO 9841605 A1 WO9841605 A1 WO 9841605A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
units
perfume
composition
formula
Prior art date
Application number
PCT/IB1998/000373
Other languages
English (en)
Inventor
Axel Masschelein
Christiaan Arthur Jacques Kamiel Thoen
Original Assignee
The Procter & Gamble Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to JP54027698A priority Critical patent/JP2001515547A/ja
Priority to CA002282566A priority patent/CA2282566A1/fr
Priority to BR9808015-6A priority patent/BR9808015A/pt
Publication of WO1998041605A1 publication Critical patent/WO1998041605A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C11D3/502—Protected perfumes
    • C11D3/507—Compounds releasing perfumes by thermal or chemical activation
    • 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
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/3723—Polyamines or polyalkyleneimines
    • 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
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3792—Amine oxide containing polymers

Definitions

  • the present invention relates to a fabric care composition with effective perfume scent delivery on fabrics.
  • Fabrics which exhibit a fresh scent is one of the areas of concern to the consumers.
  • perfumes have been incorporated into the compositions for domestic treatment such as in when used in the conventional laundering processes such as pre-treatment, laundry cycle, rinse cycle, tumble drying process and combination thereof.
  • a problem encountered with conventional perfume is that, although they provide scented fabrics, they do not provide a long lasting perfume scent, that is a scent which will last longer than the use of the conventional perfume. Indeed, the fabrics treated with the conventional perfume will often first exhibit a burst of scent on the fresh treated fabric, but upon time the scent will decrease to an almost unnoticeable degree.
  • long-lasting scent it is meant a scent on treated fabrics which lasts a longer period of time than by the use of the perfume itself in the compositions, that is preferably more than 3 days and more preferably more than 6 days.
  • Pro-perfume compounds are known in the art to fulfill such need as described in WO 96/02625.
  • pro-perfume it is meant a compound which may or may not be odoriferous in itself but which, upon hydrolysis, produces a desirable odor which is characteristic of one or more of its hydrolysis products.
  • mixtures of pro- perfume compounds can also be considered a pro-perfume.
  • the pro-perfume component can be lost during the treating process, thereby diminishing the effect of these compounds on the treated fabric.
  • the Applicant has now surprisingly found that the use of an amino- functional polymer in a composition containing a pro-perfume component fulfills such a need. Indeed, the deposition and/or substantivity of the pro-perfume component on the treated fabric has been found increased.
  • Still another advantage of the invention is to provide a composition which provide an improved care to the colors of fabrics. Indeed, by the use of the amino-functional polymer, both an improved long-lasting scent as well as an improved color care on treated fabrics has been observed.
  • the present invention is a fabric care composition
  • a pro- perfume and an amino-functional polymer, characterised in that said pro- perfume is selected from the group consisting of: a)-a nonionic or anionic ester of an allylic alcohol perfume having the formula:
  • R is selected from the group consisting of nonionic or anionic substituted or unsubstituted C1 - C30 straight, branched or cyclic alkyl, alkenyl, alkynyl, alkylaryl, or aryl group; each of R', R", and R" ' is independently selected from the group consisting of hydrogen, or a nonionic or anionic substituted or unsubstituted C1 - C25 straight, branched or cyclic alkyl, alkenyl, alkynyl, alkylaryl, or aryl group; and n is an integer of 1 or greater;
  • R is selected from the group consisting of nonionic or anionic substituted or unsubstituted C1 - C30 straight, branched or cyclic alkyl, alkenyl, alkynyl, alkylaryl, or aryl group; each of R', R", and R"' is independently selected from the group consisting of hydrogen, or a nonionic or anionic substituted or unsubstituted C1 - C25 straight, branched or cyclic alkyl, alkenyl, alkynyl, alkylaryl, or aryl group; and n is an integer of 1 or greater;
  • R is selected from the group consisting of substituted or unsubstituted C1 -C30 straight, branched or cyclic alkyl, alkenyl, alkynyl, alkylaryl or aryl group; R' is a perfume alcohol with a boiling point at 760 mm Hg of less than about 300 C; and n and m are individually an integer of 1 or greater; and
  • a method for providing color care and perfume deposition and/or substantivity on treated fabrics upon domestic treatment which comprises the step of contacting the fabrics with a composition comprising a pro-perfume and an amino-functional polymer.
  • the contacting step may occur in an aqueous medium such as in a rinse cycle, pre-treatment process or in a non aqueous medium such as that which occurs during a tumble-drying process.
  • An essential component of the invention is an amino-functional polymer. Indeed, by the present component, the deposition and/or substantivity of the pro-perfume on the treated fabric is increased. Still another advantage of the amino-functional polymer is that they provide care to the colors of fabrics.
  • the amino-functional polymers of the present invention are water-soluble or dispersible, polyamines.
  • the amino-functional polymers for use herein have a molecular weight between 200 and 10 ⁇ , preferably between 600 and 20,000, most preferably between 1000 and 1 0,000.
  • These polyamines comprise backbones that can be either linear or cyclic.
  • the polyamine backbones can also comprise polyamine branching chains to a greater or lesser degree.
  • the polyamine backbones described herein are modified in such a manner that at least one, preferably each nitrogen of the polyamine chain is thereafter described in terms of a unit that is substituted, quaternized, oxidized, or combinations thereof.
  • the term "modification" as it relates to the chemical structure of the polyamines is defined as replacing a backbone -NH hydrogen atom by an R' unit (substitution), quaternizing a backbone nitrogen (quaternized) or oxidizing a backbone nitrogen to the N-oxide (oxidized).
  • substitution and “substitution” are used interchangably when referring to the process of replacing a hydrogen atom attached to a backbone nitrogen with an R' unit. Quaternization or oxidation may take place in some circumstances without substitution, but substitution is preferably accompanied by oxidation or quaternization of at least one backbone nitrogen.
  • linear or non-cyclic polyamine backbones that comprise the amino- functional polymer have the general formula:
  • cyclic polyamine backbones that comprise the amino-functional polymer have the general formula:
  • the above backbones prior to optional but preferred subsequent modification comprise primary, secondary and tertiary amine nitrogens connected by R "linking" units
  • primary amine nitrogens comprising the backbone or branching chain once modified are defined as V or Z "terminal" units.
  • V or Z "terminal" units when a primary amine moiety, located at the end of the main polyamine backbone or branching chain having the structure
  • Z "terminal" unit is modified according to the present invention, it is thereafter defined as a Z "terminal" unit, or simply a Z unit. This unit can remain unmodified subject to the restrictions further described herein below.
  • secondary amine nitrogens comprising the backbone or branching chain once modified are defined as W "backbone" units.
  • W backbone
  • tertiary amine nitrogens comprising the backbone or branching chain once modified are further referred to as Y "branching" units.
  • Y branch point of either the polyamine backbone or other branching chains or rings, having the structure
  • -[N-R]- is modified according to the present invention, it is thereafter defined as a Y "branching" unit, or simply a Y unit.
  • Y branching
  • some or all or the tertiary amine moieties can remain unmodified. These unmodified tertiary amine moieties by virtue of their position in the backbone chain remain “branching" units.
  • the R units associated with the V, W and Y unit nitrogens which serve to connect the polyamine nitrogens, are described herein below.
  • the polyamine backbone has the formula
  • Vn-k mYnY'k wherein k is the number of ring forming branching units.
  • the polyamine backbones of the present invention comprise no rings.
  • a fully non-branched linear modified polyamine according to the present invention has the formula
  • n is equal to 0.
  • the value for m ranges from a minimum value of 2 to 700, preferably 4 to 400, however larger values of m, especially when the value of the index n is very low or nearly 0, are also preferred.
  • Each polyamine nitrogen whether primary, secondary or tertiary, once modified according to the present invention, is further defined as being a member of one of three general classes; simple substituted, quaternized or oxidized. Those polyamine nitrogen units not modified are classed into V, W, Y, Y' or Z units depending on whether they are primary, secondary or tertiary nitrogens. That is unmodified primary amine nitrogens are V or Z units, unmodified secondary amine nitrogens are W units or Y' units and unmodified tertiary amine nitrogens are Y units for the purposes of the present invention.
  • Modified primary amine moieties are defined as V "terminal" units having one of three forms: a) simple substituted units having the structure:
  • Modified secondary amine moieties are defined as W "backbone" units having one of three forms: a) simple substituted units having the structure:
  • modified secondary amine moieties are defined as Y' units having one of three forms: a) simple substituted units having the structure:
  • Modified tertiary amine moieties are defined as Y "branching" units having one of three forms: a) unmodified units having the structure:
  • Certain modified primary amine moieties are defined as Z "terminal" units having one of three forms: a) simple substituted units having the structure:
  • a primary amine unit comprising one R' unit in the form of a hydroxyethyl moiety is a V terminal unit having the formula (HOCH2CH2>HN-.
  • the Z "terminal” unit derives from a terminal primary amino moiety of the structure -NH2- Non-cyclic polyamine backbones according to the present invention comprise only one Z unit whereas cyclic polyamines can comprise no Z units.
  • the Z "terminal” unit can be substituted with any of the R' units described further herein below, except when the Z unit is modified to form an N- oxide. In the case where the Z unit nitrogen is oxidized to an N-oxide, the nitrogen must be modified and therefore R' cannot be a hydrogen.
  • the polyamines of the present invention comprise backbone R "linking" units that serve to connect the nitrogen atoms of the backbone.
  • R units comprise units that for the purposes of the present invention are referred to as “hydrocarbyl R” units and “oxy R” units.
  • the "hydrocarbyl" R units are C2-C1 2 alkylene, C4-C1 2 alkenylene, C3-C1 2 hydroxyalkylene wherein the hydroxyl moiety may take any position on the R unit chain except the carbon atoms directly connected to the polyamine backbone nitrogens; C4-C1 2 dihydroxyalkylene wherein the hydroxyl moieties may occupy any two of the carbon atoms of the R unit chain except those carbon atoms directly connected to the polyamine backbone nitrogens; Cs-C-1 2 dialkylarylene which for the purpose of the present invention are arylene moieties having two alkyl substituent groups as part of the linking chain.
  • a dialkylarylene unit has the formula
  • the "oxy" R units comprise -(RlO) x R5(ORl) x - f
  • R units are selected from the group consisting of C2-C12 alkylene, C3-C12 hydroxyalkylene, C4-C12 dihydroxyalkylene, Cs-C-
  • R units are C2-C12 alkylene, C3-C12 hydroxy-alkylene, C4-C12 dihydroxyalkylene, -(R 1 O) x R 1 -, -(R 1 O) x R 5 (OR 1 ) x -, (CH 2 CH(OH)CH2O) z (R 1 O)yR l (OCH2CH-(OH)CH 2 ) w -, and mixtures thereof, even more preferred R units are C2-C12 alkylene, C3 hydroxyalkylene, and mixtures thereof, most preferred are C2-C ⁇ alkylene.
  • the most preferred backbones of the present invention comprise at least 50% R units that are ethylene.
  • R1 units are C2"C ⁇ alkylene, and mixtures thereof, preferably ethylene.
  • R 2 is hydrogen, and -(R ⁇ O) x B, preferably hydrogen.
  • R3 is C-
  • R ⁇ units serve as part of R' units described herein below.
  • R4 is C1-C12 alkylene, C4-C12 alkenylene, C8-C12 arylalkylene, CQ- C-
  • R5 is C-
  • R 5 is preferably ethylene, -C(O)-, -C(O)NHR6NHC(O)-, -R ⁇ OR 1 )-, -CH 2 CH(OH)CH 2 -, -CH 2 CH(OH)CH2 ⁇ (R 1 O)yR 1 OCH 2 CH- (OH)CH2-, more preferably -CH2CH(OH)CH 2 -.
  • R ⁇ is C2-C12 alkylene or C ⁇ -C-
  • the preferred "oxy" R units are further defined in terms of the R ⁇ , R 2 , and R5 units.
  • Preferred "oxy” R units comprise the preferred R ⁇ , R 2 , and R5 units.
  • the preferred cotton soil release agents of the present invention comprise at least 50% R ⁇ units that are ethylene.
  • Preferred R1 , R 2 , and R ⁇ units are combined with the "oxy" R units to yield the preferred "oxy” R units in the following manner.
  • R' units are selected from the group consisting of hydrogen, C1 -C22 alkyl, C3-C22 alkenyl, C7-C22 arylalkyl, C2-C22 hydroxyalkyl, - (CH 2 ) p CO 2 M, -(CH 2 ) q SO 3 M, -CH(CH 2 CO2M)CO 2 M, -(CH 2 ) p PO 3 M, - (R 1 O) m B, -C(O)R 3 , preferably hydrogen, C2-C22 hydroxyalkylene, benzyl, C-
  • CH(CH2CO2M)CO2M most preferably C-
  • R' A most preferred R' unit is (R 1 O) x B.
  • R' units do not comprise hydrogen atom when the V, W or Z units are oxidized, that is the nitrogens are N-oxides.
  • the backbone chain or branching chains do not comprise units of the following structure: O O O t t t
  • R' units do not comprise carbonyl moieties directly bonded to a nitrogen atom when the V, W or Z units are oxidized, that is, the nitrogens are N-oxides.
  • the R' unit - C(O)R 3 moiety is not bonded to an N-oxide modified nitrogen, that is, there are no N-oxide amides having the structure
  • B is hydrogen, C ⁇
  • M is hydrogen or a water soluble cation in sufficient amount to satisfy charge balance.
  • a sodium cation equally satisfies (CH2) p C02M, and -(CH2) q SO3M, thereby resulting in -
  • CH2>pCO2Na, and -(CH2) q SO3Na moieties More than one monovalent cation, (sodium, potassium, etc.) can be combined to satisfy the required chemical charge balance. However, more than one anionic group may be charge balanced by a divalent cation, or more than one mono-valent cation may be necessary to satisfy the charge requirements of a poly- anionic radical.
  • a -(CH2>pPO3M moiety substituted with sodium atoms has the formula -(CH2)pPO3Na3- Divalent cations such as calcium (Ca 2 + ) or magnesium (Mg 2 + ) may be substituted for or combined with other suitable mono-valent water soluble cations.
  • Preferred cations are sodium and potassium, more preferred is sodium.
  • X is a water soluble anion such as chlorine (Cl " ), bromine (Br) and iodine (I-) or X can be any negatively charged radical such as sulfate (SO4 2" ) and methosulfate (CH3SO3-).
  • indices have the following values: p has the value from 1 to 6, q has the value from 0 to 6; r has the value 0 or 1 ; w has the value 0 or 1 , x has the value from 1 to 100; y has the value from 0 to 1 00; z has the value 0 or 1 ; m has the value from 2 to 700, preferably from 4 to 400, n has the value from 0 to 350, preferably from 0 to 200; m + n has the value of at least 5.
  • x has a value lying in the range of from 1 to 20, preferably from 1 to 10.
  • the preferred amino-functional polymers of the present invention comprise polyamine backbones wherein less than 50% of the R groups comprise "oxy" R units, preferably less than 20% , more preferably less than 5%, most preferably the R units comprise no "oxy" R units.
  • the most preferred amino-functional polymers which comprise no "oxy" R units comprise polyamine backbones wherein less than 50% of the R groups comprise more than 3 carbon atoms.
  • ethylene, 1 ,2- propylene, and 1 ,3-propylene comprise 3 or less carbon atoms and are the preferred "hydrocarbyl" R units. That is when backbone R units are C2-C1 2 alkylene, preferred is C2-C3 alkylene, most preferred is ethylene.
  • the amino-functional polymers of the present invention comprise modified homogeneous and non-homogeneous polyamine backbones, wherein 1 00% or less of the -NH units are modified.
  • the term "homogeneous polyamine backbone” is defined as a polyamine backbone having R units that are the same (i.e., all ethylene). However, this sameness definition does not exclude polyamines that comprise other extraneous units comprising the polymer backbone which are present due to an artifact of the chosen method of chemical synthesis.
  • ethanolamine may be used as an "initiator" in the synthesis of polyethyleneimines, therefore a sample of polyethyleneimine that comprises one hydroxyethyl moiety resulting from the polymerization "initiator” would be considered to comprise a homogeneous polyamine backbone for the purposes of the present invention.
  • a polyamine backbone comprising all ethylene R units wherein no branching Y units are present is a homogeneous backbone.
  • a polyamine backbone comprising all ethylene R units is a homogeneous backbone regardless of the degree of branching or the number of cyclic branches present.
  • non-homogeneous polymer backbone refers to polyamine backbones that are a composite of various R unit lengths and R unit types.
  • a non- homogeneous backbone comprises R units that are a mixture of ethylene and 1 ,2-propylene units.
  • a mixture of "hydrocarbyl” and “oxy” R units is not necessary to provide a non-homogeneous backbone.
  • Preferred amino-functional polymers of the present invention comprise homogeneous polyamine backbones that are totally or partially substituted by polyethyleneoxy moieties, totally or partially quaternized amines, nitrogens totally or partially oxidized to N-oxides, and mixtures thereof.
  • polyethyleneoxy moieties totally or partially quaternized amines
  • nitrogens totally or partially oxidized to N-oxides, and mixtures thereof.
  • backbone amine nitrogens must be modified in the same manner, the choice of modification being left to the specific needs of the formulator.
  • the degree of ethoxylation is also determined by the specific requirements of the formulator.
  • the preferred polyamines that comprise the backbone of the compounds of the present invention are generally polyalkyleneimines (PAI's), preferably polyethyleneimines (PEI's), or PEI's connected by moieties having longer R units than the parent PAI's or PEI's.
  • PAI's polyalkyleneimines
  • PEI's polyethyleneimines
  • PEI's polyethyleneimines
  • Preferred amine polymer backbones comprise R units that are C2 alkylene (ethylene) units, also known as polyethylenimines (PEI's).
  • Preferred PEI's have at least moderate branching, that is the ratio of m to n is less than 4: 1 , however PEI's having a ratio of m to n of 2: 1 are most preferred.
  • Preferred backbones, prior to modification have the general formula:
  • PEI's will have a molecular weight greater than 200 daltons.
  • the relative proportions of primary, secondary and tertiary amine units in the polyamine backbone will vary, depending on the manner of preparation.
  • Each hydrogen atom attached to each nitrogen atom of the polyamine backbone chain represents a potential site for subsequent substitution, quaternization or oxidation.
  • polyamines can be prepared, for example, by polymerizing ethyleneimine in the presence of a catalyst such as carbon dioxide, sodium bisulfite, sulfuric acid, hydrogen peroxide, hydrochloric acid, acetic acid, etc.
  • a catalyst such as carbon dioxide, sodium bisulfite, sulfuric acid, hydrogen peroxide, hydrochloric acid, acetic acid, etc.
  • Specific methods for preparing these polyamine backbones are disclosed in U.S. Patent 2, 1 82,306, Ulrich et al., issued December 5, 1 939; U.S. Patent 3,033,746, Mayle et al., issued May 8, 1 962; U.S. Patent 2,208,095, Esselmann et al., issued July 1 6, 1 940; U.S. Patent 2,806,839, Crowther, issued September 1 7, 1 957; and U.S. Patent 2,553,696, Wilson, issued May 21 , 1 951 ; all herein incorporated by reference.
  • Formula I depicts an amino-functional polymer comprising a PEI backbone wherein all substitutable nitrogens are modified by replacement of hydrogen with a polyoxyalkyleneoxy unit, -(CH2CH2 ⁇ )H, having the formula
  • Formula II depicts an amino-functional polymer comprising a PEI backbone wherein all substitutable primary amine nitrogens are modified by replacement of hydrogen with a polyoxyalkyleneoxy unit, - (CH2CH2O)2H, the molecule is then modified by subsequent oxidation of all oxidizable primary and secondary nitrogens to N-oxides, said polymer having the formula
  • Formula III depicts an amino-functional polymer comprising a PEI backbone wherein all backbone hydrogen atoms are substituted and some backbone amine units are quaternized.
  • the substituents are polyoxyalkyleneoxy units, -(CH2CH2 ⁇ )7H, or methyl groups.
  • the modified PEI has the formula
  • Formula IV depicts an amino-functional polymer comprising a PEI backbone wherein the backbone nitrogens are modified by substitution (i.e. by -(CH2CH2O)3H or methyl), quaternized, oxidized to N-oxides or combinations thereof.
  • the resulting polymer has the formula
  • not all nitrogens of a unit class comprise the same modification.
  • the present invention allows the formulator to have a portion of the secondary amine nitrogens ethoxylated while having other secondary amine nitrogens oxidized to N-oxides.
  • This also applies to the primary amine nitrogens, in that the formulator may choose to modify all or a portion of the primary amine nitrogens with one or more substituents prior to oxidation or quaternization. Any possible combination of R' groups can be substituted on the primary and secondary amine nitrogens, except for the restrictions described herein above.
  • amino-functional polymer suitable for use herein are poly(ethyleneimine) with a MW 1 200, hydroxyethylated poly(ethyleneimine) from Polysciences, with a MW 2000, and 80% hydroxyethylated poly(ethyleneimine) from Aldrich.
  • a typical amount of amino-functional polymer to be employed in the composition of the invention is preferably up to 90% by weight, preferably from 0.01 % to 50% active by weight, more preferably from 0.1 % to 20% by weight and most preferably from 0.5% to 1 5% by weight of the composition.
  • Still another essential component of the invention is a pro-perfume component.
  • a suitable class of pro-perfume component for use in the present invention is a nonionic or anionic ester of an allylic alcohol perfume as described in WO 96/02625.
  • the pro-perfume has the formula:
  • R is selected from the group consisting of nonionic or anionic substituted or unsubstituted C-
  • R is selected from the group consisting of nonionic or anionic substituted or unsubstituted Ci - C20 straight, branched or cyclic alkyl, alkenyl, alkynyl, alkylaryl, or aryl group; at least one R' is hydrogen; R" is hydrogen; one R"' is hydrogen, methyl, or ethyl and the other R" ' is a straight, branched, or cyclic, nonionic or anionic substituted or unsubstituted, C-
  • a preferred pro-perfume within this class is a nonionic or anionic ester of an allylic alcohol perfume having the formula:
  • R is selected from the group consisting of nonionic or anionic substituted or unsubstituted C-
  • Preferred pro-perfume component of this class are those wherein the ester of the allylic alcohol perfume is selected from the group consisting of digeranyl succinate, dineryl succinate, geranyl neryl succinate, geranyl phenylacetate, neryl phenylacetate, geranyl laurate, neryl laurate, and mixtures thereof.
  • pro-perfume component suitable for use herein is a nonionic or anionic ester of a non-allylic alcohol perfume as described in US 5,531 ,91 0 and having the formula:
  • R is selected from the group consisting of nonionic or anionic substituted or unsubstituted C1 - C30 straight, branched or cyclic alkyl, alkenyl, alkynyl, alkylaryl, or aryl group; each of R', R", and R"' is independently selected from the group consisting of hydrogen, or a nonionic or anionic substituted or unsubstituted C1 - C25 straight, branched or cyclic alkyl, alkenyl, alkynyl, alkylaryl, or aryl group; and n is an integer of 1 or greater.
  • At least one R' is hydrogen; one R' " is hydrogen or a straight, branched or cyclic C1 -C20 alkyl or alkenyl group. More preferably, one R'" is hydrogen, methyl, ethyl, or alkenyl and another R'" is a staright, branched or cyclic C1 -C20 alkyl, alkenyl, or alkylaryl group.
  • esters of this class comprises esters of the following perfume alcohols: phenoxanol, floralol, ⁇ -citronellol, nonadyl alcohol, cyclohexyl ethanol, phenyl ethanol, isoborneol, fenchol, isocyclogeranol, 2-phenyl-1 -propanol and/or 3,7-dimethyl-1 -octanol.
  • esters of this class for use herein are: di- ⁇ -citronellyl maleate, dinonadyl maleate, diphenoxanyl maleate, di(3,7-dimethyl-1 - octanyl) succinate, di(cyclohexylethyl)maleate, di(floralyl)succinate and di(phenylethyl)adipate.
  • Still another class of pro-perfume component suitable for use herein are compounds having an ester of a perfume alcohol as described in US 5,562,847.
  • the ester includes at least one free carboxylate group and has the formula
  • R is selected from the group consisting of substituted or unsubstituted C1 -C30 straight, branched or cyclic alkyl, alkenyl, alkynyl, alkylaryl or aryl group; R' is a perfume alcohol with a boiling point at 760 mm Hg of less than about 300 C; and n and m are individually an integer of 1 or greater.
  • R is selected from the group consisting of substituted or unsubstituted C-
  • the esters are maleate, succinate, pyromellitate, trimellitate citrate, phthalate or adipate esters of the alcohol perfume.
  • formula (I) includes at least one free carboxylate group.
  • R' is a perfume alcohol with a boiling point at 760 mm Hg of less than about 300°C. While most any perfume alcohol having a boiling point of less than about 300 °C may be employed, preferred alcohols include geraniol, nerol, phenoxanol, floralol, ⁇ -citronellol, nonadol, cyclohexyl ethanol, phenyl ethanol, phenoxyethanol, isoborneol, fenchol, isocyclogeraniol, 2-phenyl-1 -propanol, 3,7-dimethyl-1 -octanol, anisyl alcohol, cinnamyl alcohol, dec-9-en-1 -ol, 3-methyl-5-phenyl-1 -pentanol, 7-p-methan-1 -ol, 2,6-dimethylloct-7-en-2-ol, (Z)-hex-3-en1 -ol, 1 -hexanol, 2-he
  • R' groups are selected from the group consisting of geraniol, nerol, phenoxanol, floralol, ⁇ -citronellol, nonadol, cyclohexyl ethanol, phenyl ethanol, phenoxyethanol, isoborneol, fenchol, isocyclogeraniol, 2-phenyl-1 -propanol, 3,7-dimethyl-1 -octanol, and combinations thereof and the ester is preferably selected from maleate, succinate adipate, phthalate, citrate or pyromellitate esters of the perfume alcohol.
  • esters of the present invention include geranyl succinate, neryl succinate, ( ⁇ -citronellyl) maleate, nonadyl maleate, phenoxanyl maleate, (3,7-dimethyl-1 -octanyl) succinate, (cyclohexylethyl) maleate, ( ⁇ -citronellyl)phthalate, floralyl succinate, and (phenylethyl) adipate.
  • esters satisfying the general formula (I) may also be employed in the present invention, such as monogeranyl citrate, di( ⁇ -citronellyl) pyromellitate and di(cyclohexylethyl) citrate and the isomers of all such compounds.
  • mixtures of pro-perfume compounds can also be used herein to provide a more elaborate scent.
  • a preferred class among the above disclosed classes of pro-perfumes is the class of nonionic or anionic ester of an allylic alcohol perfumes.
  • the optional pro-perfume component is typically in an amount of from 0.01 % to 10% by weight, preferably from 0.05% to 5%, and more preferably from 0.1 % to 2%, by weight of the composition.
  • An optional component of the invention is a dye fixing agent.
  • Dye fixing agents or “fixatives”, are well-known, commercially available materials which are designed to improve the appearance of dyed fabrics by minimizing the loss of dye from fabrics due to washing. Not included within this definition are components which are fabric softeners or those described hereinafter as amino-functional polymers.
  • Cationic fixatives are available under various trade names from several suppliers. Representative examples include: CROSCOLOR PMF (July 1 981 , Code No. 7894) and CROSCOLOR NOFF (January 1 988, Code No. 8544) from Crosfield; INDOSOL E-50 (February 27, 1 984, Ref. No.
  • Dye fixing agents suitable for use in the present invention are ammonium compounds such as fatty acid - diamine condensates e.g.
  • a typical amount of the dye fixing agent to be employed in the composition of the invention is preferably up 90% by weight, preferably up to 50% by weight, more preferably from 0.001 % to 10% by weight, most preferably from 0.5% to 5% active by weight of the composition.
  • a polyolefin dispersion may optionally be used in the composition of the invention in order to provide anti-wrinkles and improved water absorbency benefits to the fabrics.
  • the polyolefin is a polyethylene, polypropylene or mixtures thereof.
  • the polyolefin may be at least partially modified to contain various functional groups, such as carboxyl, carbonyl, ester, ether, alkylamide, sulfonic acid or amide groups. More preferably, the polyolefin employed in the present invention is at least partially carboxyl modified or, in other words, oxidized. In particular, oxidized or carboxyl modified polyethylene is preferred in the compositions of the present invention.
  • the polyolefin is preferably introduced as a suspension or an emulsion of polyolefin dispersed by use of an emulsifying agent.
  • the polyolefin suspension or emulsion preferably has from 1 to 50%, more preferably from 10 to 35% by weight, and most preferably from 1 5 to 30% by weight of polyolefin in the emulsion.
  • the polyolefin preferably has a molecular weight of from 1 ,000 to 1 5,000 and more preferably from 4,000 to 1 0,000.
  • the emulsifier may be any suitable emulsification or suspending agent.
  • the emulsifier is a cationic, nonionic, zwitterionic or anionic surfactant or mixtures thereof.
  • any suitable cationic, nonionic or anionic surfactant may be employed as the emulsifier.
  • Preferred emulsifiers are cationic surfactants such as the fatty amine surfactants and in particular the ethoxylated fatty amine surfactants.
  • the cationic surfactants are preferred as emulsifiers in the present invention.
  • the polyolefin is dispersed with the emulsifier or suspending agent in a ratio of emulsifier to polyolefin of from 1 : 1 0 to 3: 1 .
  • the emulsion includes from 0.1 to 50%, more preferably from 1 to 20% and most preferably from 2.5 to 10% by weight of emulsifier in the polyolefin emulsion.
  • Polyethylene emulsions and suspensions suitable for use in the present invention are available under the tradename VELUSTROL from HOECHST Aktiengesellschaft of Frankfurt am Main, Germany.
  • the polyethylene emulsions sold under the tradename VELUSTROL PKS, VELUSTROL KPA, or VELUSTROL P-40 may be employed in the compositions of the present invention.
  • compositions of the present invention will contain from 0.01 % to 8% by weight of the dispersible polyolefin, more preferably from 0.1 % to 5% by weight and most preferably from 0.1 % to 3% by weight of the polyolefin.
  • the polyolefin is added to the compositions of the present invention as an emulsion or suspension, the emulsion or suspension is added at sufficient enough quantities to provide the above noted levels of dispersible polyolefin in the compositions.
  • a non-polymeric chlorine scavenger is another optional component of the invention.
  • Suitable levels of chlorine scavengers in the compositions of the present invention may range from 0.01 % to 1 5%, preferably from 0.02% to 10%, most preferably from 0.25% to 5%, by weight of total composition. If both the cation and the anion of the scavenger react with chlorine, which is desirable, the level may be adjusted to react with an equivalent amount of available chlorine.
  • the chlorine scavengers for use herein are selected from the group consisting of non-polymeric ammonium salts.
  • Suitable non-polymeric ammonium salts for use herein have the general formula :
  • R 2 group is a C1 -C9 alkyl or substituted (e.g., hydroxy) alkyl, or hydrogen, preferably hydrogen.
  • Each R is a C1 -C4 alkyl or substituted (e.g., hydroxy) alkyl, or hydrogen, preferably methyl or hydrogen, more preferably hydrogen, and the counterion X " is a compatible anion, for example, chloride, bromide, citrate, sulfate, etc, preferably chloride.
  • non-polymeric ammonium salts are selected from ammonium chloride, ammonium sulfate; and mixtures thereof.
  • Ammonium chloride is a preferred inexpensive chlorine scavenger for use herein.
  • a fabric softener component may also be suitably used in the composition of the invention so as to provide softness and antistastic properties to the treated fabrics.
  • the fabric softener component will typically be present at a level sufficient to provide softening and antistatic properties. Typical levels are those conventionally used in fabric softening compositions, i.e from 1 % to 99% by weight of the composition.
  • the composition will preferably comprise a level of fabric softening components for liquid compositions of from 1 % to 5% by weight for the diluted compositions or from 5% to 80%, more preferably 10% to 50%, most preferably 1 5% to 35% by weight for concentrated compositions.
  • the level of nonionic softener component in the composition will typically be from 0.1 % to 1 0%, preferably from 1 % to 5% by weight.
  • the preferred level of fabric softener component will preferably be from 20% to 99%, more preferably from 30% to 90% by weight, and even more preferably from 35% to 85% by weight.
  • Said fabric softening component may be selected from cationic, nonionic, amphoteric or anionic fabric softening component.
  • the preferred, typical cationic fabric softening components include the water-insoluble quaternary-ammonium fabric softening actives, the most commonly used having been di-long alkyl chain ammonium chloride or methyl sulfate.
  • Preferred cationic softeners among these include the following:
  • DTDMAC ditallowyl dimethylammonium chloride
  • the quaternary ammonium compounds and amine precursors herein have the formula (I) or (II), below :
  • Q is selected from -O-C(O)-, -C(O)-O-, -O-C(O)-O-, -NR -C(O)-, - C(0)-NR4- ;
  • R1 is (CH 2 ) n -Q-T 2 or T3 ;
  • R 2 is (CH 2 )m-Q-T 4 or T ⁇ or R 3 ;
  • R 3 is C1 -C4 alkyl or C1 -C4 hydroxyalkyl or H;
  • R 4 is H or C1 - 4 alkyl or C1 -C4 hydroxyalkyl
  • T ⁇ , T 2 , T 3 , T 4 , T ⁇ are independently C6-C22 alkyl or alkenyl; n and m are integers from 1 to 4; and
  • X " is a softener-compatible anion.
  • Non-limiting examples of softener-compatible anions include chloride or methyl sulfate.
  • the alkyl, or alkenyl, chain T ⁇ , T 2 , T 3 , T 4 , T ⁇ must contain at least 6 carbon atoms, preferably at least 1 1 carbon atoms, more preferably at least 1 6 carbon atoms.
  • the chain may be straight or branched.
  • Tallow is a convenient and inexpensive source of long chain alkyl and alkenyl material.
  • the compounds wherein T ⁇ , T 2 , T 3 , T 4 , T ⁇ represents the mixture of long chain materials typical for tallow are particularly preferred.
  • quaternary ammonium compounds suitable for use in the aqueous fabric softening compositions herein include :
  • DSOEDMAC di(stearoyloxyethyl) dimethylammonium chloride
  • N,N-di(tallowoyl-oxy-ethyl)-N,N-dimethyl ammonium chloride where the tallow chains are at least partially unsaturated.
  • the level of unsaturation of the fatty chain can be measured by the Iodine Value (IV) of the corresponding fatty acid, which in the present case should preferably be in the range of from 5 to 200, preferably 5 to 1 50, and more preferably 5 to 100 with two categories of compounds being distinguished, having a IV below or above 25.
  • IV Iodine Value
  • the anion is merely present as a counterion of the positively charged quaternary ammonium compounds.
  • the nature of the counterion is not critical at all to the practice of the present invention.
  • the scope of this invention is not considered limited to any particular anion.
  • amine precursors thereof is meant the secondary or tertiary amines corresponding to the above quaternary ammonium compounds, said amines being substantially protonated in the present compositions due to the pH values.
  • Additional fabric softening materials may be used in addition or alternatively to the cationic fabric softener. These may be selected from nonionic, amphoteric or anionic fabric softening material. Disclosure of such materials may be found in US 4,327, 1 33; US 4,421 ,792; US 4,426,299; US 4,460,485; US 3,644,203; US 4,661 ,269; U.S 4,439,335; U.S 3,861 ,870; US 4,308, 1 51 ; US 3,886,075; US 4,233, 1 64; US 4,401 ,578; US 3,974,076; US 4,237,01 6 and EP 472, 1 78.
  • nonionic fabric softener materials typically have a HLB of from 2 to 9, more typically from 3 to 7.
  • Such nonionic fabric softener materials tend to be readily dispersed either by themselves, or when combined with other materials such as single-long-chain alkyl cationic surfactant described in detail hereinafter. Dispersibility can be improved by using more single-long-chain alkyl cationic surfactant, mixture with other materials as set forth hereinafter, use of hotter water, and/or more agitation.
  • the materials selected should be relatively crystalline, higher melting, (e.g. > 40°C) and relatively water-insoluble.
  • Preferred nonionic softeners are fatty acid partial esters of polyhydric alcohols, or anhydrides thereof, wherein the alcohol, or anhydride, contains from 2 to 1 8, preferably from 2 to 8, carbon atoms, and each fatty acid moiety contains from 1 2 to 30, preferably from 1 6 to 20, carbon atoms.
  • such softeners contain from one to 3, preferably 2 fatty acid groups per molecule.
  • the polyhydric alcohol portion of the ester can be ethylene glycol, glycerol, poly (e.g., di-, tri-, tetra, penta-, and/or hexa-) glycerol, xylitol, sucrose, erythritol, pentaerythritol, sorbitol or sorbitan. Sorbitan esters and polyglycerol monostearate are particularly preferred.
  • the fatty acid portion of the ester is normally derived from fatty acids having from 1 2 to 30, preferably from 1 6 to 20, carbon atoms, typical examples of said fatty acids being lauric acid, myristic acid, palmitic acid, stearic acid and behenic acid.
  • Highly preferred optional nonionic softening agents for use in the present invention are the sorbitan esters, which are esterified dehydration products of sorbitol, and the glycerol esters.
  • sorbitan monostearate is a suitable material. Mixtures of sorbitan stearate and sorbitan palmitate having stearate/palmitate weight ratios varying between 10: 1 and 1 : 10, and 1 ,5-sorbitan esters are also useful.
  • Glycerol and polyglycerol esters especially glycerol, diglycerol, triglycerol, and polyglycerol mono- and/or di-esters, preferably mono-, are preferred herein (e.g. polyglycerol monostearate with a trade name of Radiasurf 7248).
  • Useful glycerol and polyglycerol esters include mono-esters with stearic, oleic, palmitic, lauric, isostearic, myristic, and/or behenic acids and the diesters of stearic, oleic, palmitic, lauric, isostearic, behenic, and/or myristic acids. It is understood that the typical mono-ester contains some di- and tri-ester, etc.
  • the "glycerol esters” also include the polyglycerol, e.g., diglycerol through octaglycerol esters.
  • the polyglycerol polyols are formed by condensing glycerin or epichlorohydrin together to link the glycerol moieties via ether linkages.
  • the mono- and/or diesters of the polyglycerol polyols are preferred, the fatty acyl groups typically being those described hereinbefore for the sorbitan and glycerol esters.
  • the pH of the liquid compositions herein is an essential parameter of the present invention. Indeed, it influences the stability of the quaternary ammonium or amine precursors compounds, especially in prolonged storage conditions.
  • the pH as defined in the present context, is measured in the neat compositions at 20°C.
  • the neat pH measured in the above-mentioned conditions, must be in the range of from 2.0 to 4.5.
  • the pH of the neat composition is in the range of 2.0 to 3.5, while if it is in a diluted form, the pH of the neat composition is in the range of 2.0 to 3.0.
  • the pH of these compositions herein can be regulated by the addition of a Bronsted acid.
  • Suitable acids include the inorganic mineral acids, carboxylic acids, in particular the low molecular weight (C1 -C5) carboxylic acids, and alkylsulfonic acids.
  • Suitable inorganic acids include HCl, H2SO4, HNO3 and H3PO4.
  • Suitable organic acids include formic, acetic, citric, methylsulfonic and ethylsulfonic acid.
  • Preferred acids are citric, hydrochloric, phosphoric, formic, methylsulfonic acid, and benzoic acids.
  • Fully formulated fabric softening compositions preferably contain, in addition to the hereinbefore described components, one or more of the following ingredients.
  • Concentrated compositions of the present invention may require organic and/or inorganic concentration aids to go to even higher concentrations and/or to meet higher stability standards depending on the other ingredients.
  • Surfactant concentration aids are typically selected from the group consisting of single long chain alkyl cationic surfactants; nonionic surfactants; amine oxides; fatty acids; or mixtures thereof, typically used at a level of from 0 to 1 5% of the composition.
  • Suitable nonionic surfactants for use herein include addition products of ethylene oxide and, optionally, propylene oxide, with fatty alcohols, fatty acids and fatty amines.
  • Suitable compounds are substantially water-soluble surfactants of the general formula :
  • R 2 is selected from primary, secondary and branched chain alkyl and/or acyl hydrocarbyl groups; primary, secondary and branched chain alkenyl hydrocarbyl groups; and primary, secondary and branched chain alkyl- and alkenyl-substituted phenolic hydrocarbyl groups; said hydrocarbyl groups having a hydrocarbyl chain length of up to 20, preferably from 10 to 1 8 carbon atoms.
  • Y is typically -O-, -C(O)O-, -C(O)N(R)-, or -C(O)N(R)R-, in which R 2 and
  • R when present, have the meanings given hereinbefore, and/or R can be hydrogen, and z is of from 5 to 50, preferably of from 1 - to 30.
  • the nonionic surfactants herein are characterized by an HLB (hydrophilic- lipophilic balance) of from 7 to 20, preferably from 8 to 1 5.
  • nonionic surfactants examples include -Straight-Chain, Primary Alcohol Alkoxylates such as tallow alcohol- EO( 1 1 ), tallow alcohol-EO( 1 8), and tallow alcohol-EO(25); -Straight-Chain, Secondary Alcohol Alkoxylates such as 2-Ci 6EO( 1 1 ); 2- C 2 ⁇ EO(1 1 ); and 2-C 1 6 EO(14);
  • Phenol Alkoxylates such as p-tridecylphenol EO(1 1 ) and p- pentadecylphenol EO( 1 8), as well as
  • Inorganic viscosity control agents which can also act like or augment the effect of the surfactant concentration aids, include water-soluble, ionizable salts which can also optionally be incorporated into the compositions of the present invention.
  • ionizable salts can be used. Examples of suitable salts are the halides of the Group IA and IIA metals of the Periodic Table of the Elements, e.g., calcium chloride, magnesium chloride, sodium chloride, potassium bromide, and lithium chloride.
  • the ionizable salts are particularly useful during the process of mixing the ingredients to make the compositions herein, and later to obtain the desired viscosity.
  • the amount of ionizable salts used depends on the amount of active ingredients used in the compositions and can be adjusted according to the desires of the formulator. Typical levels of salts used to control the composition viscosity are from 20 to 20,000 parts per million (ppm), preferably from 20 to 1 1 ,000 ppm, by weight of the composition.
  • Alkylene polyammonium salts can be incorporated into the composition to give viscosity control in addition to or in place of the water-soluble, ionizable salts above.
  • these agents can act as scavengers, forming ion pairs with anionic detergent carried over from the main wash, in the rinse, and on the fabrics, and may improve softness performance. These agents may stabilize the viscosity over a broader range of temperature, especially at low temperatures, compared to the inorganic electrolytes.
  • alkylene polyammonium salts include l-lysine monohydrochloride and 1 ,5-diammonium 2-methyl pentane dihydrochloride.
  • the products herein can also contain from 0.0001 % to about 10%, more preferably from about 0.001 % to 5%, more preferably still, from about 0.01 % to about 1 % by weight of the composition of conventional perfume components.
  • Fully-formulated perfume composition can be prepared using numerous known perfume components of natural or synthetic origin.
  • the range of the natural raw substances can embrace not only readily-volatile, but also moderately-volatile and slightly-volatile components and that of the synthetics can include representatives from practically all classes of fragrant substances, as will be evident from the following illustrative compilation: natural products, such as tree moss absolute, basil oil, citrus fruit oils (such as bergamot oil, mandarin oil, etc.), mastix absolute, myrtle oil, palmarosa oil, patchouli oil, petitgrain oil Paraguay, wormwood oil, alcohols, such as farnesol, geraniol, linalool, nerol, phenylethyl alcohol, rhodinol, cinnamic alcohol, aldehydes, such as citral, HelionalTM, alpha-hexyl-cinnamaldehyde, hydroxycitronellal, LilialTM (p-tert.
  • butyl-alpha -methyldihydrocinnamaldehyde methylnonylacetaldehyde
  • ketones such as allylionone, alpha-ionone, beta -ionone, isoraldein (isomethyl- alpha -ionone), methylionone
  • esters such as allyl phenoxyacetate, benzyl salicylate, cinnamyl propionate, citronellyl acetate, citronellyl ethoxolate, decyl acetate, dimethylbenzylcarbinyl acetate, dimethylbenzylcarbinyl butyrate, ethyl acetoacetate, ethyl acetylacetate, hexenyl isobutyrate, linalyl acetate, methyl dihydrojasmonate, styrallyl acetate, vetiveryl acetate, etc., lactones, such as gamma-
  • any conventional fragrant acetal or ketal known in the art can be added to the present composition as an optional component of the conventionally formulated perfume (c) .
  • Such conventional fragrant acetals and ketals include the well-known methyl and ethyl acetals and ketals, as well as acetals or ketals based on benzaldehyde, those comprising phenylethyl moieties, or more recently developed specialties such as those described in a United States Patent entitled "Acetals and Ketals of Oxo-Tetralins and Oxo-lndanes, see U.S. Pat. No. 5 ,084,440, issued January 28, 1 992, assigned to Givaudan Corp.
  • perfume compositions for the fabric care composition of the invention include the enol ethers of alkyl-substituted oxo-tetralins and oxo-indanes as described in U.S. Pat. 5,332,725, July 26, 1 994, assigned to Givaudan; or Schiff Bases as described in U.S. Pat. 5,264,61 5, December 9, 1 991 , assigned to Givaudan.
  • the liquid carrier employed in the instant compositions is preferably at least primarily water due to its low cost, relative availability, safety, and environmental compatibility.
  • the level of water in the liquid carrier is preferably at least 50%, most preferably at least 60%, by weight of the carrier.
  • Mixtures of water and low molecular weight, e.g., ⁇ 200, organic solvent, e.g., lower alcohols such as ethanol, propanol, isopropanol or butanol are useful as the carrier liquid.
  • Low molecular weight alcohols include monohydric, dihydric (glycol, etc.) trihydric (glycerol, etc.), and higher polyhydric (polyols) alcohols.
  • Soil Release Polymers bacteriocides, colorants, perfumes, preservatives, optical brighteners, anti ionisation agents, antifoam agents, and the like.
  • adjunct ingredients conventional to the detergent formulators of laundry and cleaning products may also be used herein.
  • the following ingredients are described for the convenience of the formulator, but are not intended to be limiting thereof.
  • Detersive ingredients may also be used in the composition of the invention. Suitable detersive ingredients are those conventional to the detergent formulators of laundry and cleaning products. Typical of such conventional detersive ingredients include detersive surfactants, builders, bleaching compounds, and mixtures thereof.
  • Nonlimiting examples of surfactants useful herein typically at levels from 1% to 55%, by weight include the conventional C-
  • the conventional nonionic and amphoteric surfactants such as the C12-C18 alkyl ethoxylates ("AE") including the so-called narrow peaked alkyl ethoxylates and C ⁇ -Ci2 alkyl phenol alkoxylates (especially ethoxylates and mixed ethoxy /propoxy), C12 C18 betaines and sulfobetaines ("sultaines"), C10- 18 amine oxides, cationic surfactants and the like, can also be included in the overall compositions.
  • the C10- 18 N-alkyl polyhydroxy fatty acid amides can also be used. Typical examples include the C12- 18 N-methylglucamides. See WO 9,206,154.
  • sugar-derived surfactants include the N-alkoxy polyhydroxy fatty acid amides, such as C10- 18 N-(3-methoxypropyl) glucamide.
  • the N-propyl through N-hexyl C12- 18 glucamides can be used for low sudsing.
  • C10- 20 conventional soaps may also be used. If high sudsing is desired, the branched-chain C-
  • Detergent builders can optionally be included in the compositions herein to assist in controlling mineral hardness. Inorganic as well as organic builders can be used. Builders are typically used in fabric laundering compositions to assist in the removal of particulate soils.
  • the level of builder can vary widely depending upon the end use of the composition and its desired physical form.
  • the compositions will typically comprise at least 1 % builder, preferably from 1 % to 80%.
  • Liquid formulations typically comprise from 5% to 50%, more typically 5% to 30%, by weight, of detergent builder.
  • Granular formulations typically comprise from 1 % to 80%, more typically from 5% to 50% by weight, of the detergent builder.
  • Lower or higher levels of builder are not meant to be excluded.
  • Inorganic or P-containing detergent builders include, but are not limited to, the alkali metal, ammonium and alkanolammonium salts of polyphosphates (exemplified by the tripolyphosphates, pyrophosphates, and glassy polymeric meta-phosphates), phosphonates, phytic acid, silicates, carbonates (including bicarbonates and sesquicarbonates), sulphates, and aluminosilicates.
  • non-phosphate builders are required in some locales.
  • compositions herein function surprisingly well even in the presence of the so-called “weak” builders (as compared with phosphates) such as citrate, or in the so-called “underbuilt” situation that may occur with zeolite or layered silicate builders.
  • silicate builders are the alkali metal silicates, particularly those having a SiO2:Na2O ratio in the range 1 .0: 1 to 3.2: 1 and layered silicates, such as the layered sodium silicates described in U.S. 4,664,839.
  • NaSKS-6 is the trademark for a crystalline layered silicate marketed by Hoechst (commonly abbreviated herein as "SKS-6").
  • the Na SKS-6 silicate builder does not contain aluminum.
  • NaSKS-6 has the delta-Na2Si ⁇ 5 morphology form of layered silicate. It can be prepared by methods such as those described in German DE-A- 3,41 7,649 and DE-A-3, 742,043.
  • SKS-6 is a highly preferred layered silicate for use herein, but other such layered silicates, such as those having the general formula NaMSi x O2 x + 1 -yH2 ⁇ wherein M is sodium or hydrogen, x is a number from 1 .9 to 4, preferably 2, and y is a number from 0 to 20, preferably 0 can be used herein.
  • Various other layered silicates from Hoechst include NaSKS-5, NaSKS-7 and NaSKS-1 1 , as the alpha, beta and gamma forms.
  • the delta-Na2Si ⁇ 5 (NaSKS-6 form) is most preferred for use herein.
  • Other silicates may also be useful such as for example magnesium silicate, which can serve as a crispening agent in granular formulations, as a stabilizing agent for oxygen bleaches, and as a component of suds control systems.
  • carbonate builders are the alkaline earth and alkali metal carbonates as disclosed in German Patent Application No. 2,321 ,001 published on November 1 5, 1 973.
  • Aluminosilicate builders are useful in the present invention. Aluminosilicate builders are of great importance in most currently marketed heavy duty granular detergent compositions, and can also be a significant builder ingredient in liquid detergent formulations. Aluminosilicate builders include those having the empirical formula:
  • z and y are integers usually of at least 6, the molar ratio of z to y is in the range from 1 .0 to 0, and x is an integer from 0 to 264, and M is a Group IA or IIA element, e.g., Na, K, Mg, Ca with valence n.
  • Useful aluminosilicate ion exchange materials are commercially available. These aluminosilicates can be crystalline or amorphous in structure and can be naturally-occurring aluminosilicates or synthetically derived. A method for producing aluminosilicate ion exchange materials is disclosed in U.S. Patent 3,985,669, Krummel, et al, issued October 1 2, 1 976.
  • Preferred synthetic crystalline aluminosilicate ion exchange materials useful herein are available under the designations Zeolite A, Zeolite P (B), Zeolite MAP and Zeolite X.
  • the crystalline aluminosilicate ion exchange material has the formula:
  • x is from 20 to 30, especially 27.
  • This material is known as Zeolite A.
  • the aluminosilicate has a particle size of 0.1 -10 microns in diameter.
  • Organic detergent builders suitable for the purposes of the present invention include, but are not restricted to, a wide variety of polycarboxylate compounds.
  • polycarboxylate refers to compounds having a plurality of carboxylate groups, preferably at least 3 carboxylates.
  • Polycarboxylate builder can generally be added to the composition in acid form, but can also be added in the form of a neutralized salt. When utilized in salt form, alkali metals, such as sodium, potassium, and lithium, or alkanolammonium salts are preferred.
  • polycarboxylate builders include a variety of categories of useful materials.
  • One important category of polycarboxylate builders encompasses the ether polycarboxylates, including oxydisuccinate, as disclosed in Berg, U.S. Patent 3, 1 28,287, issued April 7, 1 964, and Lamberti et al, U.S. Patent 3,635,830, issued January 1 8, 1 972. See also "TMS/TDS" builders of U.S. Patent 4,663,071 , issued to Bush et al, on May 5, 1 987.
  • Suitable ether polycarboxylates also include cyclic compounds, particularly alicyclic compounds, such as those described in U.S. Patents 3,923,679; 3,835, 1 63; 4, 1 58,635; 4, 1 20,874 and 4, 102,903.
  • ether hydroxypolycarboxylates copolymers of maleic anhydride with ethylene or vinyl methyl ether, 1 , 3, 5-trihydroxy benzene-2, 4, 6-trisulphonic acid, and carboxymethyloxysuccinic acid
  • various alkali metal, ammonium and substituted ammonium salts of polyacetic acids such as ethylenediamine tetraacetic acid and nitrilotriacetic acid
  • polycarboxylates such as mellitic acid, pyromellitic, succinic acid, oxydisuccinic acid, polymaleic acid, benzene 1 ,3,5-tricarboxylic acid, carboxymethyloxysuccinic acid, and soluble salts thereof.
  • Citrate builders e.g., citric acid and soluble salts thereof (particularly sodium salt), are polycarboxylate builders of particular importance for heavy duty liquid detergent formulations due to their availability from renewable resources and their biodegradability. Citrates can also be used in granular compositions, especially in combination with zeolite and/or layered silicate builders. Oxydisuccinates are also especially useful in such compositions and combinations.
  • compositions of the present invention are the 3,3- dicarboxy-4-oxa-1 ,6-hexanedioates and the related compounds disclosed in U.S. Patent 4,566,984, Bush, issued January 28, 1 986.
  • Useful succinic acid builders include the C5-C20 a'kyl and alkenyl succinic acids and salts thereof. A particularly preferred compound of this type is do- decenylsuccinic acid.
  • succinate builders include: laurylsuccinate, myristylsuccinate, palmitylsuccinate, 2- dodecenylsuccinate (preferred), 2-pentadecenylsuccinate, and the like. Laurylsuccinates are the preferred builders of this group, and are described in EP 0,200,263.
  • Fatty acids e.g., Ci 2 ⁇ i 8 monocarboxylic acids such as oleic acid and/or its salts
  • Ci 2 ⁇ i 8 monocarboxylic acids such as oleic acid and/or its salts
  • Such use of fatty acids will generally result in a diminution of sudsing, which should be taken into account by the formulator.
  • the various alkali metal phosphates such as the well-known sodium tripolyphosphates, sodium pyrophosphate and sodium orthophosphate can be used.
  • Phosphonate builders such as ethane- 1 -hydroxy- 1 , 1 - diphosphonate and other known phosphonates (see, for example, U.S. Patents 3,1 59,581 ; 3,21 3,030; 3,422,021 ; 3,400,148 and 3,422,1 37) can also be used.
  • compositions herein may optionally contain bleaching agents or bleaching compositions containing a bleaching agent and one or more bleach activators.
  • bleaching agents will typically be at levels of from 1 % to 30%, more typically from 5% to 20%, of the detergent composition, especially for fabric laundering.
  • the amount of bleach activators will typically be from 0.1 % to 60%, more typically from 0.5% to 40% of the bleaching composition comprising the bleaching agent-plus-bleach activator.
  • the bleaching agents used herein can be any of the bleaching agents useful for detergent compositions in textile cleaning or other cleaning purposes that are now known or become known. These include oxygen bleaches as well as other bleaching agents.
  • Perborate bleaches e.g., sodium perborate (e.g., mono- or tetra-hydrate) can be used herein.
  • bleaching agent that can be used without restriction encompasses percarboxylic acid bleaching agents and salts thereof. Suitable examples of this class of agents include magnesium monoperoxyphthalate hexahydrate, the magnesium salt of metachloro perbenzoic acid, 4-nonylamino-4-oxoperoxybutyric acid and diperoxydodecanedioic acid.
  • Such bleaching agents are disclosed in U.S 4,483,781 , U.S 740,446, EP 0, 1 33,354, and U.S 4,41 2,934.
  • Highly preferred bleaching agents also include 6-nonylamino-6-oxoperoxycaproic acid as described in U.S 4,634,551 .
  • Peroxygen bleaching agents can also be used. Suitable peroxygen bleaching compounds include sodium carbonate peroxyhydrate and equivalent "percarbonate" bleaches, sodium pyrophosphate peroxyhydrate, urea peroxyhydrate, and sodium peroxide. Persulfate bleach (e.g., OXONE, manufactured commercially by DuPont) can also be used. A preferred percarbonate bleach comprises dry particles having an average particle size in the range from 500 micrometers to 1 ,000 micrometers, not more than 10% by weight of said particles being smaller than 200 micrometers and not more than 1 0% by weight of said particles being larger than 1 ,250 micrometers. Optionally, the percarbonate can be coated with silicate, borate or water-soluble surfactants. Percarbonate is available from various commercial sources such as FMC, Solvay and Tokai Denka.
  • Mixtures of bleaching agents can also be used.
  • Peroxygen bleaching agents, the perborates, the percarbonates, etc. are preferably combined with bleach activators, which lead to the in situ production in aqueous solution (i.e., during the washing process) of the peroxy acid corresponding to the bleach activator.
  • bleach activators Various nonlimiting examples of activators are disclosed in U.S 4,91 5,854, and U.S 4,41 2,934.
  • NOBS nonanoyloxybenzene sulfonate
  • ISONOBS 3,5,5-tri-methyl hexanoyl oxybenzene sulfonate
  • TAED tetraacetyl ethylene diamine
  • amido-derived bleach activators include (6-octanamido- caproyDoxybenzenesulfonate, (6-nonanamidocaproyl)- oxybenzenesulfonate, (6-decanamido-caproyl)oxybenzenesulfonate, and mixtures thereof as described in U.S. Patent 4,634,551 , incorporated herein by reference.
  • bleach activators comprises the benzoxazin-type activators disclosed by Hodge et al in U.S. Patent 4,966,723. Still another class of preferred bleach activators includes the acyl lactam activators. Highly preferred lactam activators include benzoyl caprolactam, octanoyl caprolactam, 3,5,5-trimethylhexanoyl caprolactam, nonanoyl caprolactam, decanoyl caprolactam, undecenoyl caprolactam, benzoyl valerolactam, octanoyl valerolactam, decanoyl valerolactam, undecenoyl valerolactam, nonanoyl valerolactam, 3,5,5- trimethylhexanoyl valerolactam and mixtures thereof. See also U.S. Patent 4,545,784, issued to Sanderson, October 8, 1 985, incorporated herein by reference, which discloses acyl caprolactam
  • Bleaching agents other than oxygen bleaching agents are also known in the art and can be utilized herein.
  • One type of non-oxygen bleaching agent of particular interest includes photoactivated bleaching agents such as the sulfonated zinc and/or aluminum phthalocyanines. See U.S. Patent 4,033,71 8, issued July 5, 1 977 to Holcombe et al. If used, detergent compositions will typically contain from 0.025% to 1 .25%, by weight, of such bleaches, especially sulfonate zinc phthalocyanine.
  • the bleaching compounds can be catalyzed by means of a manganese compound.
  • a manganese compound Such compounds are well known in the art and include, for example, the manganese-based catalysts disclosed in U.S. 5,246,621 , U.S. 5,244,594; U.S. 5, 1 94,41 6; U.S. 5, 1 1 4,606; and EP 549,271 A1 , 549,272A1 , 544,440A2, and 544,490A1 .
  • compositions and processes herein can be adjusted to provide on the order of at least one part per ten million of the active bleach catalyst species in the aqueous washing liquor, and will preferably provide from 0.1 ppm to 700 ppm, more preferably from 1 ppm to 500 ppm, of the catalyst species in the laundry liquor.
  • enzymes such as lipases, proteases, cellulase, amylases and peroxidases.
  • a preferred enzyme for use herein is a cellulase enzyme. Indeed, this type of enzyme will further provide a color care benefit to the treated fabric.
  • Cellulases usable herein include both bacterial and fungal types, preferably having a pH optimum between 5 and 9.5. U.S.
  • Still other preferred optional ingredients suitable for use herein include enzyme stabilisers, polymeric soil release agents, materials effective for inhibiting the transfer of dyes from one fabric to another during the cleaning process (i.e., dye transfer inhibiting agents), polymeric dispersing agents, suds suppressors, optical brighteners or other brightening or whitening agents, chelating agents, fabric softening clay, anti-static agents, other active ingredients, carriers, hydrotropes, processing aids, dyes or pigments, solvents for liquid formulations and solid fillers for bar compositions.
  • enzyme stabilisers materials effective for inhibiting the transfer of dyes from one fabric to another during the cleaning process (i.e., dye transfer inhibiting agents), polymeric dispersing agents, suds suppressors, optical brighteners or other brightening or whitening agents, chelating agents, fabric softening clay, anti-static agents, other active ingredients, carriers, hydrotropes, processing aids, dyes or pigments, solvents for liquid formulations and solid fillers for bar compositions.
  • the compositions can contain water and other solvents as carriers.
  • Low molecular weight primary or secondary alcohols exemplified by methanol, ethanol, propanol, and isopropanol are suitable.
  • Monohydric alcohols are preferred for solubilizing surfactant, but polyols such as those containing from 2 to 6 carbon atoms and from 2 to 6 hydroxy groups (e.g., 1 ,3-propanediol, ethylene glycol, glycerine, and 1 ,2-propanediol) can also be used.
  • the compositions may contain from 5% to 90%, typically 1 0% to 50% of such carriers.
  • compositions detergents When formulated as a granular detergent compositions, the compositions detergents can be prepared, for example, by spray-drying (final product density 520 g/l) or agglomerating (final product density above 600 g/l) the Base Granule. The remaining dry ingredients can then be admixed in granular or powder form with the Base Granule, for example in a rotary mixing drum, and the liquid ingredients (e.g., nonionic surfactant and perfume) can be sprayed on.
  • the liquid ingredients e.g., nonionic surfactant and perfume
  • the detergent compositions herein will preferably be formulated such that, during use in aqueous cleaning operations, the wash water will have a pH of between 6.5 and 1 1 , preferably between 7.5 and 1 0.5. Laundry products are typically at pH 9-1 1 . Techniques for controlling pH at recommended usage levels include the use of buffers, alkalis, acids, etc., and are well known to those skilled in the art.
  • a method for providing color care and pro-perfume deposition and/or substantivity on fabrics upon a domestic treatment By the present use of the composition according to the invention, an improved deposition of the pro-perfume on the treated fabric has been observed compared to compositions which do not contain a polyamino-functional polymer, thereby achieving a sustained and improved perfume scent on the treated fabric. Also, observed using the composition of the invention is an enhanced care to the color of fabrics compared to compositions which do not contain a polyamino-functional polymer.
  • the domestic treatment may comprises the step of contacting the fabrics with an aqueous medium comprising a composition as defined hereinbefore.
  • said aqueous medium is at a temperature between 2 to 40°C, more preferably between 5 to 25°C.
  • Still another type of domestic treatment is where the composition of the invention is applied on a substrate, such as a dryer-sheet.
  • a method for providing color care and perfume deposition and/or substantivity on fabrics upon domestic treatment which comprises the step of contacting the fabrics with a composition as defined hereinbefore, wherein said composition is applied on a substrate, preferably a dryer-sheet.
  • the compositions are used in tumble-drying processes.
  • improved pro-perfume deposition and/or substantivity on the fabric it is meant that the fabrics which are contacted with a composition of the invention exhibit a better or equal perfume deposition and/or substantivity on the fabric compared to compositions which comprise the pro-perfume but not the amino-functional polymer.
  • the benefit of pro-perfume deposition and/or substantivity on the treated fabric is assessed by evaluating the intensity of the perfume released from the pro-perfume component on lined- and tumble- dried fabrics after 6 days.
  • the method is carried out by a panel of 6 expert judges, trained to use sensory evaluations. In this instance, expert is defined as a person having at least 6 months training with demonstrated evidence of olfactive sensitivity.
  • the data obtained using the perfumers intensity scale are then averaged to give a consensus value for the perceived intensity of perfume.
  • the perfumers intensity scale is as follows:
  • color care it is meant that fabrics which have been in contact with a composition of the invention, as defined hereinbefore, and which after, and/or prior and/or simultaneously washed with a detergent composition exhibit a better fabric color appearance compared to fabrics which have not been contacted with said composition.
  • the color care benefit may either be assessed visually or by determination of the so-called delta-E values.
  • PSU panel score unit
  • Delta E is the computed color difference as defined in ASTM D2244, i.e the magnitude and direction of the difference between two psychophysical color stimuli defined by tristimulus values, or by chromaticity coordinates and luminance factor, as computed by means of a specified set of color-difference equations defined in the CIE 1976 CIELAB opponent-color space, the Hunter opponent-color space, the Friele-Mac Adam- Chickering color space or any equivalent color space.
  • compositions of the invention are suitable for use in any steps of the domestic treatment, that is as a pre-treatment composition, as a wash additive as a composition suitable for use in the rinse-cycle of the laundry cycle or applied on a dryer-sheet.
  • a pre-treatment composition of the invention may also be in a spray, foam, or aerosol form which for example can be suitable for use while ironing, or applied on the surfaces of the tumble dryer.
  • the abbreviated component identifications have the following meanings: DEQA Di-(tallowyl-oxy-ethyl) dimethyl ammonium chloride
  • DOEQA Di-(oleyloxyethyl) dimethyl ammonium methylsulfate
  • Fatty acid tallow fatty acid IV 18 Electrolyte Calcium chloride DTDMAMS Ditallow dimethyl ammonium methylsulfate SDASA 1 :2 Ratio of stearyldimethyl amine:triple-pressed stearic acid Glycosperse S- Polyethoxylated sorbitan monostearate available from Lonza
  • PEI 1800 E1 Ethoxylated polyethylene imine (MW 1800, at 50% active) as synthesised in Synthesis example 1
  • PEI 1800 E3 Ethoxylated polyethylene imine (MW 1 800, at 50% active) as synthesised as per Synthesis example 1
  • PEI 1800 Amine oxide of ethoxylated polyethylene imine (MW 1800,
  • PEI 1200 E1 Ethoxylated polyethylene imine (MW 1200, at 50% active in water) as synthesised in Synthesis example 5
  • PEI 1200 E2 Ethoxylated polyethylene imine (MW 1200, at 50% active in water) as synthesised per Synthesis example 5
  • PEI 1200 E7 Ethoxylated polyethylene imine (MW 1200, at 50% active in water) as synthesised per Synthesis example 5
  • PEI 1 200 E7 Amine oxide of ethoxylated polyethylene imine (MW 1 200, AO at 50% active) as synthesised as per Synthesis example 5 and 4
  • Dye Fix 1 Cationic dye fixing agent (50% active) available under the tradename Tinofix Eco from Ciba-Geigy
  • Dye Fix 2 Emulsified cationic dye fixative (30% active) available under the tradename Rewin SRF-0 from CHT-Beitlich
  • Citric acid Anhydrous citric acid Carbonate Anhydrous sodium carbonate with a particle size between 200 ⁇ m and 900 ⁇ m
  • Silicate Amorphous Sodium Silicate Si ⁇ 2:Na2 ⁇ ; 2.0 ratio
  • Step A)-The ethoxylation is conducted in a 2 gallon stirred stainless steel autoclave equipped for temperature measurement and control, pressure measurement, vacuum and inert gas purging, sampling, and for introduction of ethylene oxide as a liquid.
  • a ⁇ 20 lb. net cylinder of ethylene oxide (ARC) is set up to deliver ethylene oxide as a liquid by a pump to the autoclave with the cylinder placed on a scale so that the weight change of the cylinder could be monitored.
  • PEI polyethyleneimine
  • Epomin SP-01 8 having a listed average molecular weight of 1 800 equating to 0.41 7 moles of polymer and 1 7.4 moles of nitrogen functions
  • the autoclave is then sealed and purged of air (by applying vacuum to minus 28" Hg followed by pressurization with nitrogen to 250 psia, then venting to atmospheric pressure).
  • the autoclave contents are heated to 1 30 °C while applying vacuum. After about one hour, the autoclave is charged with nitrogen to about 250 psia while cooling the autoclave to about 105 °C.
  • Ethylene oxide is then added to the autoclave incrementally over time while closely monitoring the autoclave pressure, temperature, and ethylene oxide flow rate.
  • the ethylene oxide pump is turned off and cooling is applied to limit any temperature increase resulting from any reaction exotherm.
  • the temperature is maintained between 100 and 1 1 0 °C while the total pressure is allowed to gradually increase during the course of the reaction.
  • the temperature is increased to 1 1 0 °C and the autoclave is allowed to stir for an additional hour. At this point, vacuum is applied to remove any residual unreacted ethylene oxide.
  • Step B)- The reaction mixture is then deodorized by passing about 100 cu. ft. of inert gas (argon or nitrogen) through a gas dispersion frit and through the reaction mixture while agitating and heating the mixture to
  • the final reaction product is cooled slightly and collected in glass containers purged with nitrogen.
  • Step A If a PEI 1 800 E7 is desired, the following step of catalyst addition will be included between Step A and B.
  • Vacuum is continuously applied while the autoclave is cooled to about 50 °C while introducing 376 g of a 25% sodium methoxide in methanol solution (1 .74 moles, to achieve a 1 0% catalyst loading based upon PEI nitrogen functions).
  • the methoxide solution is sucked into the autoclave under vacuum and then the autoclave temperature controller setpoint is increased to 1 30 °C.
  • a device is used to monitor the power consumed by the agitator.
  • the agitator power is monitored along with the temperature and pressure. Agitator power and temperature values gradually increase as methanol is removed from the autoclave and the viscosity of the mixture increases and stabilizes in about 1 hour indicating that most of the methanol has been removed.
  • the mixture is further heated and agitated under vacuum for an additional 30 minutes.
  • Vacuum is removed and the autoclave is cooled to 1 05 °C while it is being charged with nitrogen to 250 psia and then vented to ambient pressure.
  • the autoclave is charged to 200 psia with nitrogen.
  • Ethylene oxide is again added to the autoclave incrementally as before while closely monitoring the autoclave pressure, temperature, and ethylene oxide flow rate while maintaining the temperature between 1 00 and 1 1 0 °C and limiting any temperature increases due to reaction exotherm.
  • 4500 g of ethylene oxide resulting in a total of 7 moles of ethylene oxide per mole of PEI nitrogen function
  • the temperature is increased to 1 10 °C and the mixture stirred for an additional hour.
  • reaction mixture is then collected in nitrogen purged containers and eventually transferred into a 22 L three neck round bottomed flask equipped with heating and agitation.
  • the strong alkali catalyst is neutralized by adding 1 67 g methanesulfonic acid (1 .74 moles).
  • PEI 1 800 E2, PEI 1 800 E3, PEI 1 800 E1 5 and PEI 1 800 E20 can be prepared by the above method by adjusting the reaction time and the relative amount of ethylene oxide used in the reaction.
  • Dimethyl sulfate (Aldrich, 3.8g, 0.030 mol) is added all at once to the rapidly stirring solution, which is then stoppered and stirred at room temperature overnight.
  • acetonitrile is evaporated on the rotary evaporator at ⁇ 60°C, followed by a Kugelrohr apparatus (Aldrich) at ⁇ 80°C to afford ⁇ 220g of the desired material as a dark brown viscous liquid.
  • a ⁇ r -NMR (D2O) spectrum shows the absence of a peak at ⁇ 58ppm corresponding to dimethyl sulfate.
  • a ⁇ H-NMR (D2O) spectrum shows the partial shifting of the peak at 2.5ppm (methylenes attached to unquaternized nitrogens) to ⁇ 3.0ppm.
  • the flask is stoppered, and after an initial exotherm the solution is stirred at room temperature overnight.
  • a 1 H- NMR (D2O) spectrum shows the total shifting of the methylene peaks at 2.5-3.0ppm to ⁇ 3.5ppm.
  • To the solution is added ⁇ 5g of 0.5% Pd on alumina pellets, and the solution is allowed to stand at room temperature for - 3 days.
  • Peroxide indicator paper shows that no peroxide is left in the system. The material is stored as a 46.5% solution in water.
  • polyethyleneimine having a molecular weight of 1 800 and ethoxylated to a degree of about 7 ethoxy groups per nitrogen (PEI- 1 800, E7) (209 g, 0.595 mol nitrogen, prepared as in Synthesis Example I), and hydrogen peroxide (1 20 g of a 30 wt % solution in water, 1 .06 mol).
  • PI- 1 800, E7 polyethyleneimine having a molecular weight of 1 800 and ethoxylated to a degree of about 7 ethoxy groups per nitrogen
  • hydrogen peroxide (1 20 g of a 30 wt % solution in water, 1 .06 mol).
  • Step A)-The ethoxylation is conducted in a 2 gallon stirred stainless steel autoclave equipped for temperature measurement and control, pressure measurement, vacuum and inert gas purging, sampling, and for introduction of ethylene oxide as a liquid.
  • a - 20 lb. net cylinder of ethylene oxide (ARC) is set up to deliver ethylene oxide as a liquid by a pump to the autoclave with the cylinder placed on a scale so that the weight change of the cylinder could be monitored.
  • PEI polyethyleneimine
  • Ethylene oxide is then added to the autoclave incrementally over time while closely monitoring the autoclave pressure, temperature, and ethylene oxide flow rate.
  • the ethylene oxide pump is turned off and cooling is applied to limit any temperature increase resulting from any reaction exotherm.
  • the temperature is maintained between 1 00 and 1 1 0 °C while the total pressure is allowed to gradually increase during the course of the reaction.
  • Step B)- The reaction mixture is then deodorized by passing about 100 cu. ft. of inert gas (argon or nitrogen) through a gas dispersion frit and through the reaction mixture while agitating and heating the mixture to 1 30 °C.
  • inert gas argon or nitrogen
  • the final reaction product is cooled slightly and collected in glass containers purged with nitrogen. In other preparations the neutralization and deodorization is accomplished in the reactor before discharging the product.
  • Step A If a PEI 1 200 E7 is desired, the following step of catalyst addition will be included between Step A and B.
  • Vacuum is continuously applied while the autoclave is cooled to about 50 °C while introducing 376 g of a 25% sodium methoxide in methanol solution (1 .74 moles, to achieve a 1 0% catalyst loading based upon PEI nitrogen functions).
  • the methoxide solution is sucked into the autoclave under vacuum and then the autoclave temperature controller setpoint is increased to 1 30 °C.
  • a device is used to monitor the power consumed by the agitator.
  • the agitator power is monitored along with the temperature and pressure. Agitator power and temperature values gradually increase as methanol is removed from the autoclave and the viscosity of the mixture increases and stabilizes in about 1 hour indicating that most of the methanol has been removed.
  • the mixture is further heated and agitated under vacuum for an additional 30 minutes. Vacuum is removed and the autoclave is cooled to 105 °C while it is being charged with nitrogen to 250 psia and then vented to ambient pressure. The autoclave is charged to 200 psia with nitrogen. Ethylene oxide is again added to the autoclave incrementally as before while closely monitoring the autoclave pressure, temperature, and ethylene oxide flow rate while maintaining the temperature between 1 00 and 1 10 °C and limiting any temperature increases due to reaction exotherm. After the addition of 4500 g of ethylene oxide (resulting in a total of 7 moles of ethylene oxide per mole of PEI nitrogen function) is achieved over several hours, the temperature is increased to 1 1 0 °C and the mixture stirred for an additional hour.
  • reaction mixture is then collected in nitrogen purged containers and eventually transferred into a 22 L three neck round bottomed flask equipped with heating and agitation.
  • the strong alkali catalyst is neutralized by adding 1 67 g methanesulfonic acid ( 1 .74 moles).
  • PEI 1 200 E2 PEI 1 200 E3, PEI 1 200 E1 5 and PEI 1 200 E20 can be prepared by the above method by adjusting the reaction time and the relative amount of ethylene oxide used in the reaction.
  • the corresponding amine oxide of the above ethoxylated PEI can also be prepared following synthesis Example 4.
  • Dimethyl sulfate (Aldrich, 8.48g, 0.067 mol) is added all at once to the rapidly stirring solution, which is then stoppered and stirred at room temperature overnight.
  • acetonitrile is evaporated on the rotary evaporator at — 60°C, followed by a Kugelrohr apparatus (Aldrich) at ⁇ 80°C to afford ⁇ 220g of the desired material as a dark brown viscous liquid.
  • a l (D2O) spectrum shows the absence of a peak at — 58ppm corresponding to dimethyl sulfate.
  • a " ⁇ - NMR (D2O) spectrum shows the partial shifting of the peak at 2.5ppm (methylenes attached to unquaternized nitrogens) to ⁇ 3.0ppm.
  • poly(ethyleneimine) poly(ethyleneimine), MW 1 200 which has been ethoxylated to a degree of 7, and - 9.5% quaternized with dimethyl sulfate (144g, - 0.37 mol oxidizeable nitrogen, prepared as in Example 6), hydrogen peroxide (Aldrich, 35.4g of a 50 wt% solution in water, 0.52 mol), and water (1 00g).
  • the flask is stoppered, and after an initial exotherm the solution is stirred at room temperature overnight.
  • a ⁇ H-NMR (D2O) spectrum shows the total shifting of the methylene peaks at 2.5-3.0ppm to ⁇ 3.5ppm.
  • composition 2 is a hydrophobic perfume composition, that is having wherein less than 25% by weight of the perfume comprises perfume ingredients having a Clog P of 3 or smaller as defined in US-5,460,736 Example 2
  • compositions for use as dryer-added sheets are in accordance with the invention.
  • liquid detergent formulation according to the present invention was prepared:

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Cosmetics (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

La présente invention, qui concerne une composition pour conditionneur de tissus, comprend un pro-parfum et un polymère à fonction amino. Cette composition garantit un meilleur dépôt du pro-parfum et/ou une meilleure persistance sur les tissus traités.
PCT/IB1998/000373 1997-03-14 1998-03-16 Compositions pour conditionneur de tissus WO1998041605A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP54027698A JP2001515547A (ja) 1997-03-14 1998-03-16 布地保護組成物
CA002282566A CA2282566A1 (fr) 1997-03-14 1998-03-16 Compositions pour conditionneur de tissus
BR9808015-6A BR9808015A (pt) 1997-03-14 1998-03-16 Composições para preservação de tecidos

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP97200777A EP0864642A1 (fr) 1997-03-14 1997-03-14 Compositions d'entretien des tissus
EP97200777.7 1997-03-14

Publications (1)

Publication Number Publication Date
WO1998041605A1 true WO1998041605A1 (fr) 1998-09-24

Family

ID=8228108

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB1998/000373 WO1998041605A1 (fr) 1997-03-14 1998-03-16 Compositions pour conditionneur de tissus

Country Status (7)

Country Link
EP (1) EP0864642A1 (fr)
JP (1) JP2001515547A (fr)
CN (1) CN1255158A (fr)
AR (1) AR012840A1 (fr)
BR (1) BR9808015A (fr)
CA (1) CA2282566A1 (fr)
WO (1) WO1998041605A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6187727B1 (en) * 1999-07-12 2001-02-13 Bush Boake Allen, Inc. Fragrance materials

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999021954A1 (fr) * 1997-10-29 1999-05-06 The Procter & Gamble Company Compositions pour lessives a mauvaises odeurs reduites et procedes de preparation desdites compositions
US6753307B1 (en) 1998-10-13 2004-06-22 The Procter & Gamble Company Laundry detergent compositions with a cationically charged dye maintenance polymer
BR9914502B1 (pt) * 1998-10-13 2008-11-18 composiÇÕes detergentes para lavagem de tecidos com um polÍmero de manutenÇço de corante carregado de forma catiânica e composiÇço para condicionamento de tecidos.
AR030176A1 (es) * 1999-12-22 2003-08-13 Procter & Gamble Composicion de lavar ropa y/o de limpiar y/o para el cuidado de las telas y metodos para proveer una deposicion aumentada y una liberacion retardada del agente de beneficio sobre superficies tratadas
EP1111034A1 (fr) 1999-12-22 2001-06-27 The Procter & Gamble Company Compositions de détergents et de nettoyants et/ou de soin des tissus
US20030158079A1 (en) * 2001-10-19 2003-08-21 The Procter & Gamble Company Controlled benefit agent delivery system
CN102037112A (zh) * 2008-05-28 2011-04-27 宝洁公司 具有良好稳定性的织物软化衣物洗涤剂
JP6607686B2 (ja) * 2015-03-26 2019-11-20 ライオン株式会社 繊維製品用の液体洗浄剤

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4372882A (en) * 1980-06-17 1983-02-08 The Procter & Gamble Company Detergent composition containing low level of substituted polyamines
US4597898A (en) * 1982-12-23 1986-07-01 The Proctor & Gamble Company Detergent compositions containing ethoxylated amines having clay soil removal/anti-redeposition properties
US4891160A (en) * 1982-12-23 1990-01-02 The Proctor & Gamble Company Detergent compositions containing ethoxylated amines having clay soil removal/anti-redeposition properties
US5500154A (en) * 1994-10-20 1996-03-19 The Procter & Gamble Company Detergent compositions containing enduring perfume

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4125752A1 (de) * 1991-08-03 1993-02-04 Basf Ag Polymerisate aus ethylenisch ungesaettigten, n-haltigen verbindungen, polymerisiert in gegenwart von monosacchariden, oligosacchariden, polysacchariden oder deren derivaten
US5559088A (en) * 1995-07-07 1996-09-24 The Proctor & Gamble Company Dryer-activated fabric conditioning and antistatic compositions with improved perfume longevity
US5531910A (en) * 1995-07-07 1996-07-02 The Procter & Gamble Company Biodegradable fabric softener compositions with improved perfume longevity
DE69534903T2 (de) * 1995-08-31 2007-01-18 The Procter & Gamble Company, Cincinnati Verwendung von Allylalkohol als ein Mittel zur Verminderung von schlechten Gerüchen
US5562847A (en) * 1995-11-03 1996-10-08 The Procter & Gamble Company Dryer-activated fabric conditioning and antistatic compositions with improved perfume longevity

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4372882A (en) * 1980-06-17 1983-02-08 The Procter & Gamble Company Detergent composition containing low level of substituted polyamines
US4597898A (en) * 1982-12-23 1986-07-01 The Proctor & Gamble Company Detergent compositions containing ethoxylated amines having clay soil removal/anti-redeposition properties
US4891160A (en) * 1982-12-23 1990-01-02 The Proctor & Gamble Company Detergent compositions containing ethoxylated amines having clay soil removal/anti-redeposition properties
US5500154A (en) * 1994-10-20 1996-03-19 The Procter & Gamble Company Detergent compositions containing enduring perfume

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6187727B1 (en) * 1999-07-12 2001-02-13 Bush Boake Allen, Inc. Fragrance materials

Also Published As

Publication number Publication date
CN1255158A (zh) 2000-05-31
CA2282566A1 (fr) 1998-09-24
AR012840A1 (es) 2000-11-22
BR9808015A (pt) 2000-03-08
JP2001515547A (ja) 2001-09-18
EP0864642A1 (fr) 1998-09-16

Similar Documents

Publication Publication Date Title
WO1998020102A1 (fr) Compositions de parfum
US6103678A (en) Compositions comprising a perfume and an amino-functional polymer
WO1998020098A1 (fr) Compositions respectant les couleurs
US5721202A (en) Perfumes for laundry and cleaning composition
US6184197B1 (en) Polymeric compound comprising one or more active alcohols
WO1998012296A1 (fr) Compositions pour l'entretien des couleurs
WO1998012236A1 (fr) Compose polymere comprenant un ou plusieurs alcools actifs
WO1998041605A1 (fr) Compositions pour conditionneur de tissus
WO1999016801A1 (fr) Compose glyoxylique comprenant un ou plusieurs ingredients actifs
US5670466A (en) Sulfonate perfumes for laundry and cleaning compositions
WO1999027055A1 (fr) Compositions de soin pour tissus
US6559243B1 (en) Glyoxylic compound comprising one or more active ingredient
CA2310434C (fr) Compositions adoucissantes stabilisees pour tissus
EP1034202A1 (fr) Composes copolymeres renfermant un ou plusieurs motifs monomeres actifs d'aldehyde
MXPA99008416A (en) Fabric care compositions
MXPA99004307A (en) Perfume compositions
MXPA99004187A (en) Color care compositions
MXPA99002627A (en) Polymeric compound comprising one or more active alcohols

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 98804979.1

Country of ref document: CN

AK Designated states

Kind code of ref document: A1

Designated state(s): BR CA CN JP MX US

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
ENP Entry into the national phase

Ref document number: 2282566

Country of ref document: CA

Ref document number: 2282566

Country of ref document: CA

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: PA/a/1999/008416

Country of ref document: MX

ENP Entry into the national phase

Ref document number: 1998 540276

Country of ref document: JP

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: 09381081

Country of ref document: US