CA2316503A1 - Fabric softener composition - Google Patents

Fabric softener composition Download PDF

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Publication number
CA2316503A1
CA2316503A1 CA2316503A CA2316503A CA2316503A1 CA 2316503 A1 CA2316503 A1 CA 2316503A1 CA 2316503 A CA2316503 A CA 2316503A CA 2316503 A CA2316503 A CA 2316503A CA 2316503 A1 CA2316503 A1 CA 2316503A1
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Prior art keywords
fabric
fragrance
enzyme
fragrance precursor
composition according
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CA2316503A
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French (fr)
Inventor
Markus Gautschi
Philippe Blondeau
Samuel Derrer
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Givaudan SA
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Givaudan Roure International SA
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Publication of CA2316503A1 publication Critical patent/CA2316503A1/en
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    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50Perfumes
    • C11D3/502Protected perfumes
    • C11D3/507Compounds releasing perfumes by thermal or chemical activation
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/835Mixtures of non-ionic with cationic compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D11/00Special methods for preparing compositions containing mixtures of detergents
    • C11D11/0094Process for making liquid detergent compositions, e.g. slurries, pastes or gels
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/38Products with no well-defined composition, e.g. natural products
    • C11D3/386Preparations containing enzymes, e.g. protease or amylase

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  • 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)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Fats And Perfumes (AREA)
  • Detergent Compositions (AREA)

Abstract

The present invention provides a fabric softening composition containing a surfactant as fabric softener, a fragrance precursor, as well as an enzyme suitable for cleaving the fragrance precursor. Upon application of a solution of the softening composition to a fabric, the fragrance precursor is cleaved by the enzyme and a desired odor is imparted to the fabric.
Processes for imparting an odor to a fabric using such compositions are also provided.

Description

Attorney Docket No. 12982/117615 FABRIC SOFTENING COMPOSITION
FIELD OF THE INVENTION
The present invention relates to a fabric softening composition that includes a surfactant as fabric softener and a fragrance precursor. Processes for preparing a fabric softening composition and imparting odor to a fabric are also provided.
BACKGROUND OF THE INVENTION
The usual process for cleaning fabrics includes washing the fabric with a detergent containing a surfactant, followed by rinsing and drying. Enzymes are incorporated into the detergents to improve the removal of stains. Proteases have been described to be useful in detergents to remove proteinaceous stains (See, e.g., Aunstrup, et al., U.S.
Patent No.
3,723,250). Amylases have been described to be useful in detergent compositions to remove starchy stains (See, e.g., McCarty, et al., U.S. Patent No. 3,627,688).
Lipases have been described to be useful in detergent compositions to improve the removal of fat soiling (See, e.g., Huge-Jensen, et al., U.S. Patent No. 4,810,414). The use of lipase in detergents has been reviewed by H. Andree, et al., J. Applied Biochem. 1980, 2, 218-229. Further, a non-dusting granulate containing a cellulase has been added to a detergent composition in order to reduce the harshness of the laundry (See, e.g., Barbesgaard, et al., U.S. Patent No.
4,435,307).
It is also known that applying an enzyme during the rinsing step, instead of the washing step, improves the enzymatic effect. Advantageously, the enzyme is applied in the last rinsing step together with a fabric softening and/or antistatic agent (such as a cationic surfactant, see, e.g., WO 91/13136). The addition of an enzyme during the last rinsing step improves the removal of fatty matters both with and without a cationic surfactant.
2 discloses a solid fabric softening composition for use in the rinsing step of a fabric washing process that includes a fabric softening conditioning compound, a lipase, F:\DMS\KCH\GIVAUDAN\A 12982v2.doc and a dispersing agent. Using such a solid fabric softening composition, significant cleaning benefits on white cotton were reportedly obtained while the softening effect was maintained.
A principal strategy currently employed to impart odors to consumer products is the admixing of the fragrance directly into the product. There are, however, several drawbacks to this strategy. The fragrance material can be too volatile, resulting in fragrance loss during manufacturing, storage, and use. Many fragrance materials are also unstable over time. This again results in fragrance loss during storage.
In many consumer products, it is desirable for the fragrance to be released slowly over time. Microencapsulation and inclusion complexes with cyclodextrins have been used to help decrease volatility, improve stability, and provide slow-release properties.
However, these methods are, for a number of reasons, often not successful. In addition, cyclodextrins can be too expensive.
Fragrance precursors for scenting fabrics washed in the presence of a lipase-containing detergent are described in WO 95/04809. Such fragrance precursors are cleaved by the lipase and a single odoriferous compound, either an odoriferous alcohol, aldehyde, or ketone is yielded. Thereby, a prolonged scenting effect on the fabric is obtained.
Despite this advantage, problems remain with the stability of different types of fragrance precursors. This problem was overcome by separating the enzyme and the fragrance precursor and incorporating the enzyme into the detergent and the fragrance precursor into the fabric softening composition. However, using this approach, a scenting effect by the fragrance precursors can only be achieved if an enzyme containing detergent is used in the washing step. As most consumers are not familiar with the detergent and fabric softener technology, it is likely that a fabric softening composition containing a fragrance precursor will be used in combination with a detergent not containing an enzyme, thus rendering the fragrance precursor system useless.
It is also known that during the laundry process some enzyme activity is lost, e.g. due to denaturation, or adsorption of the enzyme to soil. Therefore, the remaining enzyme activity may not be sufficient to cleave the fragrance precursors during the rinsing/drying cycle. In this case too, the precursor technology is not very efficient. This problem was partially overcome by increasing the dosage of enzyme, especially lipase, in the detergent. However, consumers have become increasingly aware of enzymes added to consumer goods which are manufactured by means of genetic engineering. Negative side effects usually associated with these enzymes, e.g. allergic reactions of the skin, have led to the marketing of safe, non-bio detergents. These types of non-bio detergents are not suitable in combination with enzyme cleavable fragrance precursors.
Currently used lipases e.g. LIPOLASE~, remove fatty stains mainly during the last stages of rinsing and drying steps.
Thereby also esters of short chain acids are cleaved leaving an unpleasant smell on the fabric. The latter may be overcome by introduction of enzymes, e.g. lipases, that are especially active during the washing step. However, with these types of new lipases, e.g.
LIPOPRIME~, designed for good stain removal during the washing cycle, a decrease in cleavage of fragrance precursors is observed during the drying cycle compared to LIPOLASE~.
SUMMARY OF THE INVENTION
In summary, the methods and compositions set forth above suffer from various drawbacks in producing a stable, long lasting and user friendly system to impart odor to a fabric. Accordingly, an object of the present invention is to provide a fragrance delivery system which yields a long lasting pleasant odor, especially a fresh odor or a clean scent, on a fabric.
Another object of the present invention is to provide a stable fragrance delivery system.
A further object of the present invention is to provide a fragrance delivery system, which works without special measures to be taken by the user.
A further object of the present invention is to avoid the problems of the old delivery systems.
One embodiment of the invention is a fabric softening composition for imparting an odor to a fabric that includes a surfactant, a fragrance precursor, and an enzyme that cleaves the fragrance precursor.
Another embodiment of the invention is a process for preparing a fabric softening composition as set forth above. This process includes mixing the surfactant, fragrance precursor, and enzyme, wherein the enzyme and the fragrance precursor are mixed into the composition last.
A further embodiment of the invention is a process for imparting an odor to a fabric.
This process includes rinsing the fabric with a composition containing a surfactant, a fragrance precursor, and an enzyme that will cleave the fragrance precursor.
The present invention also provides a process for imparting an odor to a fabric. This process includes adding a fabric softening composition to the fabric during a rinse step in a fabric cleaning process wherein the fabric softening composition includes a surfactant, a fragrance precursor, and an enzyme that will cleave the fragrance precursor.
The enzyme is then allowed to cleave the fragrance precursor to form a fragrance molecule which imparts a fresh, clean, long lasting scent to the fabric.
DETAILED DESCRIPTION OF THE INVENTION
It has been found that a fabric softening composition containing a surfactant as fabric softener, a fragrance precursor, and an enzyme suitable for cleaving the fragrance precursor, upon application to the rinsing step of a fabric cleaning process, imparts a fresh, clean and long lasting scent to the fabric and solves the problems set forth above.
The odor obtained on the fabric after using the softening composition of the present invention in the rinsing step is long lasting (up to 2-3 weeks) and is determined by the choice of the fragrance precursor(s).
Surprisingly, it has been found that the fabric softener composition of the invention is stable during storage. The odor develops generally during and/or after rinsing and during the drying cycle and continues for a longer period.
Due to the application of the fragrance precursor and the enzyme in the same composition or delivery system, no special knowledge is needed and no special measures have to be taken to obtain the desired result.
The fabric softening composition of the invention includes at least 0.01 wt%
of one or more fragrance precursors. In the present invention, it is preferred to use from about O.Olwt%
to about l5wt%, such as for example, from about O.lwt% to about lOwt%. It is also preferred to use from about 0.2% to about 2 % per weight of one or more fragrance precursors.
The fabric softening composition also includes an enzyme selected from the group of lipase, cellulase, protease, and amylase. The enzyme is present in the fabric softening composition in the range of 0.001 mg to 5 mg, preferably 0.01 mg to 2 mg of pure enzyme per liter of the fabric softening composition.
The fabric softening composition also includes from about 1 % to about 80% per weight of surfactants and other substances useful in fabric softening compositions and known to the skilled person. Such substances include, for example, preservatives, fragrances, and the like.
In a preferred embodiment, the fabric softening composition contains cationic surfactants. Additionally, the fabric softening composition may contain a non-ionic surfactant to assist in the dispersion of the cationic fabric softener in the water and to improve the rewetability of the fabric. The compositions of the present invention preferably include from about lwt% to about 80wt%, preferably from about 3wt% to about SOwt %, of a cationic surfactant. Diluted liquid compositions preferably contain from about 3wt% to about l5wt%
of a cationic surfactant. Concentrated liquid compositions preferably contain from about l2wt% to about SOwt%, more preferably from about l2wt% to about 35wt% of a cationic surfactant.
The fabric softening composition is preferably a liquid, however, granular, gelatinous or viscous, clear or translucent liquid embodiments are also part of the present invention.
The pH value of the fabric softening composition of the present invention is an important parameter influencing its stability and its resistance to microbial infection. The pH, as defined in the present context, is measured in the neat fabric softening composition at 20°C. For optimum hydrolytic stability, the pH of the neat composition is in the range from about 2.0 to about 5.0, preferably from about 2.0 to 3.5. The pH value of the composition may be adjusted to the desired range by addition of a Bronsted acid, such as for example inorganic mineral acids, carboxylic acids, and alkylsulfonic acids. The fragrance precursors, being preferably of the ester and carbonate type, and the fabric softeners of the ester type, are stable under these acidic conditions in the composition. The acidic pH value also ensures a satisfactory enzyme stability, especially of lipase, cellulase, amylase, and protease. Under these conditions, good stability of fragrance precursors as well as of fabric softener and antistatic agents was observed over a prolonged period of time.
The fabric softening composition of the invention is dissolved or diluted in the rinsing step of the washing cycle and is deposited onto the fabric surface due to the high substantivity of the individual compounds to the fabric. When a pH value of about 7 in the rinsing liquid is reached, the enzyme is activated and the fragrance precursor is cleaved to release the fragrance. The release of the fragrance may start either in the rinsing step or during the drying step where the water content of the fabric is reduced. After drying, the release of the fragrance continues. Depending on the precursors chosen, the fabric has a desired odor, e.g.
fresh and clean, for at least two weeks.
Using a detergent containing an enzyme for stain removal during the washing step followed by a fabric softening composition of the present invention during the rinsing step, a clean fabric with a long-lasting, fresh and clean scent may be obtained.
The fabric softening composition of the present invention may also include different fragrance precursors which are cleaved under different conditions, and enzymes that cleave at least one fragrance precursor.
The fabric softening compositions of the present invention may be prepared by combining the components set forth above according to the art. For example, a composition according to the present invention may be prepared by first admixing the surfactants with water at an elevated temperature. After cooling, further components e.g.
preservatives, fragrances, etc. may be added. The fragrance precursors and the enzymes may be added at any stage of the formulation. Preferably the precursors and enzymes are added at the last step of the mixing process. The fragrance precursors) may be added in neat form to the composition or, preferably, dissolved in a suitable solvent. The fragrance precursors may be added in encapsulated, spray-dried, or any other "protected form" known to those skilled in the art. The enzymes) may be added as a liquid or in any other form, e.g.
dried, encapsulated, extruded or spray-dried. It is possible to prepare a coencapsulate, coextrudate or any other form containing both the fragrance precursors(s) and the enzyme(s).
A fragrance precursor in the softening composition of the present invention may be a compound of formula:
YLm R"
wherein Y is a carrier residue, such as a polymer, a carbohydrate or any type of mono-or poly-carboxylic acid, to which a fragrant alcohol, aldehyde, ketone or oxime may be chemically bound;

L is a bivalent linker residue, such as dicarboxylic acids, amino acids, hydroxy acids and the like;
R is the residue of a fragrant alcohol, oxime, or of the enol form of a fragrant aldehyde or ketone;
m is 0 or an integer from 1 to n; and n is an integer > 1 and if n > 1 the residues R may be the same or different.
Fragrance precursors that meet this general formula are described, e.g. in WO 95/04809, in WO 96/02625, in WO 97/16523 or in WO 98/07683.
The following fragrance precursor compounds are preferred in the present invention:
(a) Formula I:
R2 R' HO (CR5R6)~OR~
R3 R4 .. I IO
wherein n is 1, 2 or 3;
R' to R6 are, independently, substituted or unsubstituted alkyl-, alkenyl-, alkinyl-, cycloalkyl-, cycloalkenyl- or aromatic-residues or hydrogen, wherein these residues may in addition contain one or more -O- and /or -C(O)- groups; and R' is a residue of a fragrant alcohol R'OH, wherein one or two rings may be built by the combination of the respective R' to R6 groups and this/these rings) may be further substituted by alkyl-groups;
(b) Formula II:
_g_ O
~ (II) R ~O~X R9 n wherein Rg is the residue of the enol form of an aldehyde or ketone;
X is a saturated or unsaturated bivalent hydrocarbon residue with a straight or branched chain with 1 to 20 carbon atoms optionally containing one or more heteroatoms, such as O, N, S, and/or P and/or a group -C(O)- and/or substituents of the formula -COOY, -OH, -C(O)-, or -NHZ where Y is H, a metal atom or R", and R" is the rest of an alcohol or phenol R"OH or has the same definition as Rg and is the same or different as Rg, R9 is a saturated or unsaturated, substituted or unsubstituted carbocyclic or heterocyclic residue or -COOY, wherein Y is H, a metal atom or R'°, and R'° is the rest of an alcohol or phenol or has the same definition as Rg and is the same or different as R8, and R9 may be H if X is substituted by -OH; and nis0orl;
(c) Formula IIIa:
O_a-~ Si(R'2)a CR'3H-CR'5HAC0(OR'4) (Ills) (d) Formula IIIb:
O_3-a Si(R~2)a CR'SACO(OR'4) CR~3H (Illb) or a mixture of IIa and IIIb, and if any other units) in the siloxanes are present, they are of (e) Formula IV:

R'sbSiO ~ (p z wherein R'Z is a substituted or unsubstituted C,_g alkyl group or a substituted or unsubstituted aryl group;
R'6 is a hydrogen atom, a monovalent C,_g hydrocarbon group or a monovalent C
i-s halogenated hydrocarbon group;
R'3 is a hydrogen atom, a substituted or unsubstituted C,_g alkyl group, a substituted or unsubstituted aryl group, or a bond connecting CR'3 and CR's;
R'S is a hydrogen atom, a substituted or unsubstituted C~_g alkyl group, or a substituted or unsubstituted aryl group;
A is (CR"2)n wherein R" is a substituted or unsubstituted C1-$ alkyl group or a substituted or unsubstituted aryl group, or a hydrogen atom;
n is 0-20, preferably 1 to 10, and each R" is the same or different;
OR'4 is the residue of an olfactive alcohol or of the enol form of an olfactive aldehyde or olfactive ketone;
a is 0, 1 or 2; and bis0, l,2or3;
(f) Formula V:

O
18 ~
R \O- _OZ R19 M
n wherein R'g is the residue of the enol form of an aldehyde or ketone;
R'9 is a saturated or unsaturated, substituted or unsubstituted C,-C3°
aliphatic residue with straight or branched chains optionally having one or more heteroatoms in the chain, the residue of the enol form of an aldehyde or ketone, the residue of an alcohol, -COOY or -OCOOY, wherein Y is H, a metal atom or Rz°, and RZ° is the rest of an alcohol RZ°OH or has the same definition as R'$;
Z is a saturated or unsaturated bivalent hydrocarbon residue with a straight or branched chain with 1 to 30 carbon atoms optionally containing one or more heteroatoms, and/or a group -C(O)- and/or substituents of the formula -COOY, -OCOOY, -OH, -C=O, or -NHz and Y is H, a metal atom or RZ', and RZ' is the rest of an alcohol RZ'OH
or has the same definition as R'8 and is the same or different as R'g; and nis0orl.
The heteroatoms in Z and in R'9, representing a C,-C3° aliphatic residue, may be O, N, S and/or P. The substituents of R'9, representing a C,-C3° aliphatic residue, may be ionic such as -NH3+ or COO-;
(g) Formula VI:
O
y / -O R22 n wherein Y is the residue of an organoleptic ketone or lactone of the formula YH;
Rzz is H or the residue of a mono- or polyalcohol of the formula Rzz-(OH)S
with s >_ 1;
p= 1 or2;
n >_ 1; and q=lor2 wherein if n > l, the residues of Y may be different or the same;
(h) Formula VII:
O R2s R2a ~ C~2R (VII) Rz~ RZS RZa wherein Rz3 is a residue of either an alcohol Rz30H, or a residue of an alcohol Rz30H
which further contains at least one remaining part of formula VII;
Rz4 to Rzg are independently H or substituted or unsubstituted, branched or unbranched alkyl-, alkenyl-, akinyl-, cycloalkyl-, cycloalkenyl-, or aromatic residues, preferably with 1 to 10 C atoms, or Rz4 or Rz5 is COZRz3; and/or at least one of the pairs Rz4+RzS, Rzs+Rz6~ Rzs+Rz', or Rzb+Rz', Rzb+Rzg form a saturated, unsaturated, or aromatic ring with 3 to 7 C atoms, preferably with 5 to 6 C atoms, wherein this/these rings) may be further substituted by one or more alkyl- and/or alkenyl residues and/or by one or more -COZRz9 groups wherein Rz9 is a residue of an alcohol Rz90H, whereby Rz9 is preferably Rz3.
The alcohol Rz30H is preferably organoleptic.

Other conventional components that release fragrant molecules by enzymatic, UV
and/or thermal cleavage from a carrier material may be included in the fabric softening compositions of the present invention.
In the present invention, the fabric softening composition further includes a fabric surfactant as a softener and/or an antistatic agent. In a preferred embodiment of the present invention, the fabric softening and/or antistatic agents are cationic surfactants. Suitable fabric softening compounds are well known to those skilled in the art and are e.g.
described by R.
Puchta, J. American Oil Chem. Soc. 1984, 61, 367-376 or by G.R. Whalley, happi 1995, February, 55-58, which is incorporated by reference as if recited in full herein. Preferred fabric softening agents which are constituents of the rinse added fabric softening compositions of the present invention are exemplified in the following non-limiting examples.
Preferred surfactants are cationic quaternary ammonium salts having two long hydrocarbyl chains, for instance two C$_zg, preferably C,z_za, hydrocarbyl chains. Preferably the hydrocarbyl groups are alkyl or alkenyl groups, which are optionally substituted or interrupted by other groups. Well-known species of substantially water-insoluble quaternary ammonium compounds have the formula:
Rya R33 +
N X-R3~ ~ ~ Rs2 wherein R3' and R3z are independently selected from hydrocarbyl groups of from about 8 to about 28, preferably about 12 to about 24 carbon atoms;
R33 and R34 are hydrocarbyl groups containing from 1 to about 4 carbon atoms;

X is an anion, preferably selected from halide, methosulfate, and ethylsulfate radicals.
Representative examples of these quaternary softeners include ditallow dimethyl ammonium chloride, ditallow dimethyl ammonium methyl sulphate, dihexadecyl dimethyl ammonium chloride, di(hydrogenated tallow) dimethyl ammonium methyl sulfate, dihexadecyl diethyl ammonium chloride, and di(coconut) dimethyl ammonium chloride.
Ditallow dimethyl ammonium chloride, di(hydrogenated tallow) dimethyl ammonium chloride, di(coconut) dimethyl ammonium chloride and di(coconut) dimethyl ammonium methosulfate are preferred examples of the quaternary softeners.
Other suitable quaternary softeners include dialkyl ethoxyl methyl ammonium methosulfate based on soft fatty acid, dialkyl ethoxyl methyl ammonium methosulfate based on hard fatty acid, and a material in which R33 and R34 represent methyl.
Preferably, R3' is C,3_l5, Rsz is CHzCH20COR35 where R35 is stearyl, and X is methosulfate.
The quaternary ammonium compound may be an ester-linked quaternary ammonium compound represented by the formula:
(Rss~H~(CH2)n -T-Rs7lm wherein each R36 group is independently selected from C,_6 hydrocarbyl, such as alkyl, alkenyl or hydroxyalkyl groups;
each R3' group is independently selected from Cg_28 linear or branched hydrocarbyl, such as alkyl or alkenyl groups;

T is -O- C- ~ -C -O- > -N- C- ~ -C -N-n is an integer from 0-5;
m is an integer from 1-4; and X- is an anion which is compatible with fabric softening ingredients, preferably selected from halide, methosulfate and ethylsulfate residues.
A preferred class of surfactants of this type is that of formula:
O +
HO-H2C- Hz ~ /CH2 CH2 O-C-R39 N X

wherein each R39 is a linear or branched alkyl or alkenyl chain containing at least 11 atoms such as tallow; and X~ is as defined above and, in particular, is methosulfate.
A material having R39 of tallow and X- of methosulfate is available from Witco under the trade name REWOQUAT WE 18.
Another example of this type of suitable material has an R39 of partially hardened tallow and X- of methosulfate.
Another preferred class of surfactants containing two ester groups is:
O +
H3 ~ /CH2 CH2 O-C-R4o -HN O X
H C \CH -CH2 O-C-R4o wherein R4° is a linear or branched alkyl or alkenyl residue such as tallow, or partially hardened tallow; and X' is an anion which is compatible with fabric softening. Preferred choices of X- are chloride or methosulfate.
Other ester-linked quaternary ammonium compounds, which may be used in the compositions of the present invention, are those of formula:
,841,4-m N~~CHZ)~-CH-T-R42, X -T-R42 m wherein each R4' is independently selected from C,~ hydrocarbyl, such as alkyl, alkenyl or hydroxyalkyl groups;
each R42 is independently selected from Cg_2g linear or branched hydrocarbyl, such as alkyl and alkenyl groups;
T is as described above;
n is an integer of from 0-5;
m is an integer from 1-4; and X- is an anion preferably selected from halide, methosulfate and ethylsulfate residues.
Another class of preferred water-insoluble cationic fabric softeners are the hydrocarbylimidazolinium salts believed to have the formula:
O
N~ I~ ~ _ R4si \ (CH2)2 -N- C-R X

R~
wherein R43 is a hydrocarbyl group containing from 1 to 4, preferably 1 or 2 carbon atoms;
R46 is a hydrocarbyl group containing from 8 to 25 carbon atoms;
R44 is a linear or branched hydrocarbyl group containing from 8 to 25 carbon atoms;
R45 is hydrogen or a hydrocarbyl containing from 1 to 4 carbon atoms; and X- is an anion, preferably a halide, methosulfate or ethylsulfate.
Preferred imidazolinium salts include 1-methyl-1-(tallowylamido-) ethyl-2-tallowyl-4,5-dihydroimidazolinium methosulfate and 1-methyl-1-(palmitoylamido) ethyl-2-octadecyl-4,5-dihydroimidazolinium chloride. Other useful imidazolinium salts are 2-heptadecyl-1-methyl-1-(2-stearylamido)-ethyl-imidazolinium chloride and 2-lauryl-1-hydroxyethyl-1-oleyl-imidazolinium chloride.
Another class of preferred fabric softeners is an inorganic or organic acid salt of a fabric softening compound of formula:
as _ R -C-H-(CH2)~ N-(CHZ)m N-C-R X

wherein R4' and R4g are independently C,2 to C3o aliphatic hydrocarbon residues;
R'9 is (CHZCHZO)PH, CH3 or H;
n=lto5;
m=lto5;
p = 1 to 10; and X- is an anion which is compatible with fabric softening ingredients.
Another preferred class of fabric softener is a biodegradable fatty ester quaternary ammonium compound of formula:

p +
R5' (CH2)q O-C -R5o -a N O aX
Rsz/ ~ CH -p-2~r C
wherein each RS° independently is an aliphatic hydrocarbon residue having from 8 to 22 carbon atoms;
RS' is (CHz)SRs3 where R53 is an alkoxy carbonyl residue containing from 8 to carbon atoms, benzyl, phenyl, C,-C4 alkyl substituted phenyl, OH or H;
R5z is (CHZ)~Rsa where R54 is benzyl, phenyl, C,-C4 alkyl substituted phenyl, OH, or H;
q, r, s, and t are each independently an integer from 1 to 3; and X- is an anion of valence a.
Other conventional components that have fabric softening effects and/or antistatic effects may also be added to the fabric softening composition of the present invention.
According to the present invention the fabric softening composition further includes an enzyme. Preferably the enzyme is a lipase, a cellulase, a protease, an amylase, or any combination of these agents. However, any other type of enzyme suitable to cleave fragrance precursors used in the present invention may be used.
Lipases of plant or animal origin (e.g. pancreas lipase) may be used in the invention, but microbial lipases are preferred for reasons of economy. Some lipases are known to be active in detergents. Because the conditions in the rinsing step are favorable for most lipases, many other lipases may be used. Examples of lipases that may be used in the present invention include those derived from the following microorganisms, indicated with reference:
Humicola, e.g., H. insolens (US 4,810,414) Pseudomonas, e.g., Ps. cepia or Ps. fluorescens (WO 89/04361) Fusarium, e.g., F. oxysporum (EP 130,064) Mucor (also called Rhizomucor), e.g., M. miehei Candida, e.g., C. cylindracea ( also called C. rugosa) or C. antarctica (WO
88/02775) Preferred lipases are commercially available enzymes, e.g., LIPOLASE~, LIPOLASE
ULTRA~, arid LIPOPRIME~ (Novo Nordisk) Proteases of plant or animal origin may be used in the invention, but microbial proteases are preferred for reasons of economy. Proteases useful in the present invention may, for example, be derived from Bacillus licheniformis. Preferred proteases are commercially available enzymes, e.g. ALCALASE~, SAVINASE~, EVERLASE~ and ESPERASE~ from 1 S Novo Nordisk; PURAFECT~, PURAFECT~ OX, and PROPERASE~ from Genencor.
Amylases of plant or animal origin may be used in the invention, but microbial amylases are preferred for reasons of economy. Amylases useful in the present invention may, for example, be derived from Bacillus subtilis. Preferred amylases are commercially available enzymes, e.g. TERAMYL~, BAN, and DURAMYL~ from Novo Nordisk, and PURASTAR~ ST, and PURASTAR"~ OxAm from Genencor.
Cellulases of plant or animal origin may be used in the invention, but microbial cellullases are preferred for reasons of economy. Cellulases useful in the present invention may, for example, be derived from Humicola insolens. Preferred cellulases are commercially available enzymes, e.g. CELLUZYME~, and CAREZYME~ from Novo Nordisk, and PURADEX~ HA, and Detergent Cellulase L from Genencor.

Compositions of the present invention may also include dispersing agents for assisting the dispersion of the fabric softeners in water. Suitable dispersing agents are known to those skilled in the art and include nonionic surfactants such as alkoxylated fatty alcohols and fatty acid partial esters of polyhydric alcohols, e.g. glycerol, erythrol, sorbitol and the like.
S The compositions of the present invention may be stabilized against microbial infection, preferably by incorporation of a stabilizing agent such as an inorganic salt (e.g.
NaCI), a sugar (e.g. sucrose and glucose), a polyol (e.g. glycerol and propylene glycol), and an alcohol (e.g. ethanol and isopropanol). These stabilizing agents are usually effective in amounts above 10%, especially above 20%. Other examples of suitable stabilizing agents useful in the present invention include organic acids, such as benzoic acid, sorbic acid, and the like, that are generally effective in amounts of O.Olwt%-2% at low pH (below 5). Other stabilizing agents are antioxidants, e.g, sulphur dioxide, 1,2-bent-iso-thiazolin-3-one (BIT), and parabens. Further additives may be added to improve enzyme stability in the fabric softening composition. These additives are selected depending on the nature of the enzymes) used in the fabric softening composition, and are known by those skilled in the art.
The compositions of the invention may further include other optional ingredients such as perfume, perfume carriers, fluorescers, colorants, hydrotropes, antifoaming agents, antiredeposition agents, optical brightening agents, anti-shrinking agents, anti-wrinkle agents, fabric crisping agents, anti-spotting agents, soil release agents, germicides, linear or branched silicones, fungicides, antimicrobial agents, antioxidants, preservatives, dyes, bleaches and bleach precursors, and ironing aids. These optional ingredients, if added, are preferably present at levels up to 5% by weight of the composition.
The following examples are provided to further illustrate the compositions and processes of the present invention, and are not intended to limit the scope of the invention in any way.

EXAMPLES
Example 1 A fabric softening composition of the present invention of the ester quat type, 4 x concentrate, was formulated as follows:
Ingredients Chemical Name %wt Part A

DEIONIZED WATER to 100.0 MgCl2 (saturated sol.) Magnesium chloride 1.0 Part B

REWOQUAT WE 18 di-(tallow carboxyethyl) hydroxy-ethyl15.0 methylammonium methosulfate GENAPOL O 100 ethoxylated fatty alcohol 2.0 ANTIFOAM DB 31 0.5 Part C

ISOPROPYL ALCOHOL 3.0 PRESERVATIVE QS

FRAGRANCE PRECURSOR'S 0.5 LIPOLASE~ 100L

While stirring and heating to 65°C, part A was mixed with part B
(preheated to 65°C).
After cooling to room temperature, part C was added to the mixture of A and B.
The pH value of the finished product was 2.60.
'~ The Fragrance Precursor used was:

O"O O"O

carbonic acid 2,3-bis-[Z]-hex-3-enyloxycarbonyloxy-propyl ester [Z]-hex-3-enyl ester Example 2 A fabric softening composition of the present invention of the ester quat type, 1 x concentrate, was formulated as follows:
Ingredients Chemical Name %wt Part A

DEIONIZED WATER to 100.0 Part B

REWOQUAT WE 18 Di-(tallow carboxyethyl) hydroxy-ethyl6.0 methylammonium methosulfate DOBANOL 25-9 Ethoxylated fatty alcohol C 0.5 ANTIFOAM DB 31 0.1 Part C

MYACIDE BT 30 2-bromo-2-nitropropane 1,3 0.03 diol PROXEL GXL Benzisothiazolinone sodium 0.02 salt FRAGRANCE PRECURSORZ~ 0.5 LIPOLASE~ 100L 0.05 While stirring and heating to 65°C, part A was mixed with part B
(preheated to 65°C).
After cooling to room temperature, part C was added to the mixture of A and B.
The pH value of the finished product was 3.50.
Z~ The Fragrance Precursor used was:

O
O O
O
O-succinic acid (Z)-hex-3-enyl ester 3-methoxycarbonylmethyl-2-pentyl-cyclopent-1-enyl ester Example 3 A fabric softener composition of the present invention of the quat type concentrate was formulated as follows:
Ingredients Chemical Name %wt Part A

DEIONIZED WATER to 100.0 CaClz Calcium chloride 0.6 Part B

ARQUAD 2 HT 75 13.0 Part C

DOW CORNING DB 100 Silicone 0.2 FORMALDEHYDE (10%) 0.15 FRAGRANCE PRECURSOR3~ 0.5 LIPOLASE~ 100L 0.05 While stirring and heating to 65°C, part A was mixed with part B
(preheated to 65°C).
After cooling to room temperature, part C was added to the mixture of A and B.
The pH value of the finished product is 3.20.

3~ Fragrance Precursor:
O
O
O
O
O
O' succinic acid 3,7-dimethyl-octa-2,6-dienyl ester 3-methoxycarbonylmethyl-2-pentyl-cyclopent-1-enyl ester Example 4 A fabric softener composition of the present invention of the quat type 1 x concentrate was formulated as follows:
Ingredients Chemical Name %wt Part A

DEIONIZED WATER to 100.0 Part B

ARQUAD 2 HT 75 4.5 Part C

ISOPROPYL ALCOHOL 0.85 MYACIDE 2-bromo-2-nitropropane 1,3-diol0.03 PROXEL GXL benziosthiazoline sodium salt0.02 FRAGRANCE PRECURSOR4~ 0.5 LIPOLASE~ 100L 0.05 While stirring and heating to 65°C, part A was mixed with part B
(preheated to 65°C).
After cooling to room temperature, part C was added to the mixture of A and B.

The pH value of the finished product was 3.20.
4~ The Fragrance Precursor used was:
2-(Z)-hex-3-enyloxycarbonyloxy-succinc acid 4-(3,7-dimethyl-oct-6-enyl) ester methyl ester.
O
O O~O~v O O
O
Example 5 A fabric softener composition of the present invention of the ester quat type, 4 x concentrate, was formulated as follows:
Ingredients Chemical Name %wt Part A _ DEIONIZED WATER to 100.0 MgCl2 (saturated sol.) Magnesium chloride 1.0 Part B

REWOQUAT WE 18 Di-(tallow carboxyethyl) hydroxy-ethyl15.0 methylammonium methosulfate GENAPOL O 100 Ethoxylated fatty alcohol C 2.0 ANTIFOAM DB 31 0.5 Part C

ISOPROPYL ALCOHOL 3.0 PRESERVATIVE QS

FRAGRANCE PRECURSORS 0.5 SAVINASE~ (16.0 L EX) 0.05 While stirring and heating to 65°C, part A was mixed with part B
(preheated to 65°C).
After cooling to room temperature, part C was added to the mixture of A and B.
The pH value of the finished product was 2.60.
O
~N O
O
O
O
O' 5~ The Fragrance Precursor used was:
(~-hex-3-enyloxycarbonylamino-acetic acid 3-methoxy-carbonylmethyl-2-pentyl-cyclopent-1-enyl ester.
Example 6 Washing and rinsing tests with the fabric softening compositions of the present invention demonstrate the long lasting fragrance delivery.
Fabric: 2 cotton terry towels size: 50x90 cm; weight: 250g/towel.
Washing: Miele WS 5405.
Detergent wash cycle : 40° C (program 4).
Detergent: A-C, as indicated below.
Rinsing: Miele WS 5405.
The fabric softening composition is added to the washing compartment via the dispenser.
Fabric softening composition: D-L, as indicated below.
Dosage of regular fabric softening composition (examples 2 and 4): 110 g.
Dosage of concentrated fabric softening composition (examples 1 and 3): 35 g.
Evaluation: After the washing and rinsing steps the towels are placed in a basket. The odor of the wet towels is evaluated by a panel of 10 perfumers.
The towels are line dried at ambient temperature overnight and are evaluated after 2, 5, 10, and 20 days by a panel of 10 perfumers. The panelists are asked to evaluate each towel and to indicate whether the fragrance material can be perceived. Panelists are also asked to indicate the preference of the two towels being presented, one being the control towel and one being the towel treated with the fabric softening composition of the present invention.
Detergent A: commercially available compact detergent, without enzymes Detergent B: commercially available compact detergent containing about 0.05-0.2%
of lipase Detergent C: detergent A
addition of 0.05% LIPOLASE~ 100T
Fabric softening composition D: according to example 1 Fabric softening composition E: according to example 1 without LIPOLASE~ 100L
Fabric softening composition F: according to example 3 Fabric softening composition G: according to example 3 without LIPOLASE~ 100L
Fabric softening composition H: according to example 2, containing 0.3 % of Carbonic acid 2,3-bis-[Z]-hex-3-enyloxycarbonyloxy-propyl ester [Z]-hex-3-enyl ester ('~) as the fragrance precursor.
Fabric softening composition I: according to example 2, containing 0.3 % of Carbonic acid 2,3-bis-[Z]-hex-3-enyloxycarbonyloxy-propyl ester [Z]-hex-3-enyl ester ('~) as the fragrance precursor, without LIPOLASE~ 100L.
Fabric softening composition K: according to example 4, containing 0.3 % of Carbonic acid 2,3-bis-[Z]-hex-3-enyloxycarbonyloxy-propyl ester [Z]-hex-3-enyl ester ('~) as the fragrance precursor.
Fabric softening composition L: according to example 4, containing 0.3 % of Carbonic acid 2,3-bis-[Z]-hex-3-enyloxycarbonyloxy-propyl ester [Z]-hex-3-enyl ester ('~) as the fragrance precursor, without LIPOLASE~ 100L.
Example 7 Two towels labeled #1 were washed with detergent A and subsequently rinsed with fabric softening composition D. Two other towels labeled #2 were washed with detergent B

and subsequently rinsed with fabric softening composition E, as described in example 6.
In a paired, blind test the panelists were asked to indicate the strength of the fragrance (cis-3-hexenol) and to indicate a preference for towel #1 or towel #2. The fragrance strength was rated as: no sensation, barely detectable, weak, moderate, strong, very strong, strongest imaginable.
Time Strength* Preference Towel # 1 Towel #2 Towel # 1 Towel #2 Wet Moderate Weak 8 2 2 days Strong Moderate 10 0 5 days Strong Weak 10 0 days Moderate Barely detect. 10 0 days Weak no sensation 10 0 * Average of panelist opinion ** Indicated as how many out of the 10 panelists Using the fabric softening composition of the present invention, containing a fragrance precursor for cis-3-hexenol, a fresh and clean green fragrance was perceived up to three 10 weeks. At most evaluation stages, the towels treated with the fabric softening composition of the present invention were preferred by all 10 perfumers participating in the evaluation.
Example 8 Two towels labeled #1 were washed with detergent A and subsequently rinsed with fabric softening composition F, as described in example 6. Two other towels labeled #2 were 15 washed with detergent B and subsequently rinsed with fabric softening composition G, as described in example 6.
In a paired, blind test the panelists were asked to indicate the strength of the fragrance (HEDIONE~ and geraniol) and to indicate a preference for towel # 1 or towel #2. The strength was rated as: no sensation, barely detectable, weak, moderate, strong, very strong, strongest imaginable.
Time Strength* Preference*

Towel # 1 Towel #2 Towel # 1 Towel #2 Wet Moderate Moderate 8 2 2 days Strong Moderate 9 1 days Strong Moderate 10 0 days Moderate Weak 10 0 days Weak Weak 10 0 * Average of panelist opinion 5 * * Indicated as how many out of the 10 panelists Using the fabric softening composition of the present invention, containing a fragrance precursor for HEDIONE~ and geraniol, a fresh and clean floral fragrance was perceived up to three weeks. At most evaluation stages the towels treated with the fabric softening composition of the present invention were preferred by all 10 perfumers participating in the 10 evaluation.
Example 9 Stability test:
According to example 6, towels labeled #1, #2, #3, and #4 were washed using the detergents and softeners given in the table below. All detergents and softeners used were 15 stored in glass bottles at 37°C for 1 month. The towels were line-dried and the strength of cis-3-hexenol, the fragrant material to be released slowly, was evaluated in a blind test by a panel of 10 trained perfumers. The strength was rated as: no sensation, barely detectable, weak, moderate, strong, very strong, strongest imaginable.
Towels Detergent Softener Cis-3-hexenol strength*

24 hours 48 hours # 1 A H Weak Moderate #2 C I Weak Weak #3 A K Weak Moderate #4 C L Weak Weak * Average of panelist opinion After one month of storage, equal or better results in strength were obtained for the fabric softening compositions of the present invention compared to a combination of detergent/softener where the precursor and the enzyme were separated, thus demonstrating the stability of the fabric softening compositions of the present invention.
The invention being thus described, it will be obvious that the same may be varied in many ways. Such variations are not to be regarded as a departure from the spirit and scope of the invention and all such modifications are intended to be included within the scope of the following claims.

Claims (15)

WHAT IS CLAIMED IS:
1. A fabric softening composition for imparting an odor to a fabric comprising: a surfactant, a fragrance precursor, and an enzyme that cleaves the fragrance precursor.
2. A composition according to claim 1 further comprising 1 to 80% by weight of a surfactant selected from the group consisting of anionic and cationic surfactants.
3. A composition according to claim 1 wherein the enzyme is selected from the group consisting of proteases, amylases, lipases, cellulases, and combinations thereof.
4. A composition according to claim 1 wherein the fragrance precursor is of the formula:
YLm Rn wherein Y is a carrier residue, L is a bivalent linker residue, m is O or an integer 1 to n, R is a residue of a fragrance molecule, yielding upon cleavage a fragrance RH and n is an integer ~
1.
5. A composition according to claim 4 wherein R is a residue of a fragrant alcohol, oxime, or residue of the enol form of an aldehyde or ketone.
6. A composition according to claim 1 wherein the fragrance precursor is cleaved by the enzyme.
7. A composition according to claim 6 wherein the enzyme cleaves the fragrance precursor in response to heat, moisture, UV, and increased pH.
8. A composition according to claim 1 wherein the enzyme is active at a water concentration of below 100% based on the dry weight of the dry fabric.
9. A composition according to claim 1 wherein 0.01 to 15% per weight of the composition is the fragrance precursor.
10. A composition according to claim 1 having a pH value of ~ 5Ø
11. A composition according to claim 1 comprising a Bronsted acid.
12. A composition according to claim 1 wherein the composition is in liquid form.
13. A process for preparing a fabric softening composition according to claim comprising mixing the surfactant, fragrance precursor, and enzyme, wherein the enzyme and the fragrance precursor are mixed into the composition last.
14. A process for imparting an odor to a fabric comprising rinsing the fabric with a composition comprising a surfactant, a fragrance precursor, and an enzyme that will cleave the fragrance precursor.
15. A process for imparting an odor to a fabric comprising:
(a) adding a fabric softening composition to the fabric during a rinse step in a fabric cleaning process wherein the fabric softening composition comprises a surfactant, a fragrance precursor, and an enzyme that will cleave the fragrance precursor;
and (b) allowing the enzyme to cleave the fragrance precursor to form a fragrance molecule which imparts a fresh, clean, long lasting scent to the fabric.
CA2316503A 1999-08-18 2000-08-17 Fabric softener composition Abandoned CA2316503A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
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EP99810739 1999-08-18

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ATE409512T1 (en) * 2001-12-13 2008-10-15 Firmenich & Cie COMPOUNDS FOR THE CONTROLLED RELEASE OF ACTIVE MOLECULES
JP5396213B2 (en) * 2009-09-16 2014-01-22 花王株式会社 Perfume composition for softener
KR101369087B1 (en) * 2012-07-17 2014-03-03 한국타이어 주식회사 Radial Tire capable of Detecting Deformation of Tire Bead

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