CN117580993A - Textile product for drum drying - Google Patents

Textile product for drum drying Download PDF

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Publication number
CN117580993A
CN117580993A CN202280046011.6A CN202280046011A CN117580993A CN 117580993 A CN117580993 A CN 117580993A CN 202280046011 A CN202280046011 A CN 202280046011A CN 117580993 A CN117580993 A CN 117580993A
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China
Prior art keywords
group
fragrance
pro
textile article
textile
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CN202280046011.6A
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Chinese (zh)
Inventor
R·蔻特斯
R·克纳博
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Firmenich SA
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Firmenich SA
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Priority claimed from PCT/EP2022/067747 external-priority patent/WO2023275056A1/en
Publication of CN117580993A publication Critical patent/CN117580993A/en
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Abstract

The present invention relates to textile articles comprising a pro-fragrance compound that can be used in tumble drying. The invention also relates to a method for producing the textile product, and to the use of the textile product for improving, enhancing, giving and/or modifying the fragrance impression and/or fragrance intensity of garments during drum drying.

Description

Textile product for drum drying
Technical Field
The present invention relates to textile articles (textile articles) comprising pro-fragrance compounds which can be used for drum drying. The invention also relates to a method for producing the textile product, and to the use of the textile product for improving, enhancing, giving and/or modifying the fragrance impression and/or fragrance intensity of garments during drum drying.
Background
A well-known commercial product in the laundry care industry is a dry sheet (dry laundry). In use, the consumer typically uses at least one sheet during the drying cycle of the washing process. The dryer sheet is typically textile-based, wherein the textile material carries one or more ingredients to impart desired benefits to the garment during the drum drying process. These ingredients may be, for example, perfumes, antistatic agents, dye transfer inhibitors, brighteners, enzymes, anti-soil agents, anti-wrinkle agents, fabric softeners, and the like.
One of the main factors of customer satisfaction is that the drying sheet provides the laundry with a high intensity pleasant fragrance impression during the drum drying process for as long as possible, i.e. the pleasant fragrance impression should still last as long as possible after the drum drying process.
This goal is challenging because the high temperatures and simultaneous mechanical agitation during tumble drying can significantly affect the stability and longevity of many fragrance compounds. Thus, a pleasant fragrance impression of the laundry may be perceived directly after the drum drying process, but the effect may not be strong and/or durable.
One approach to address the above objectives is to encapsulate the fragrance compound within a carrier material prior to incorporation of the fragrance compound into the dry tablet. The encapsulated form of the fragrance compound can withstand the rather harsh conditions imposed during tumble drying and the encapsulated fragrance applied to the garment during tumble drying may not be released immediately but continuously, which results in an extended fragrance perception, wherein the fragrance is still perceived, typically after days or even months. However, encapsulation of the perfuming ingredients can be laborious and expensive.
Accordingly, other solutions are needed to improve and extend the fragrance impression provided to the laundry during the drum drying process.
Drawings
Fig. 1. Overall fragrance intensity of towels dried using unflavored dry sheets and towels dried using flavored dry sheets.
Detailed Description
The present invention relates to textile articles comprising a pro-fragrance compound,
wherein the pro-fragrance compound is a compound of formula (I),
wherein:
a) w represents an integer of 1 to 10000;
b) n represents 1 or 0;
c) m represents an integer of 1 to 6;
d) P represents a hydrogen atom or a group which is liable to generate an odorous alpha, beta-unsaturated ketone, aldehyde or carboxylate, and is represented by the following formula (II):
wherein the wavy line indicates the position of the bond between P and X; r is R 1 Represents hydrogen atom, C 1 To C 6 Alkoxy or C 1 To C 15 Straight, cyclic or branched alkyl, alkenyl or alkadienyl optionally substituted with 1 to 4C 1 To C 4 An alkyl group; and is also provided with
R 2 、R 3 And R is 4 Independently of one another, represents a hydrogen atom, an aromatic ring or C 1 To C 15 Straight, cyclic or branched alkyl, alkenyl or alkadienyl, possibly substituted by C 1 To C 4 An alkyl group; or R is 1 To R 4 Two or three of the groups are bonded together to form a group having 5 to 20 carbon atoms and including the group R 1 、R 2 、R 3 Or R is 4 Saturated or unsaturated rings of carbon atoms to which the radicals are bound, the rings possibly being substituted by C 1 To C 8 Linear, branched or cyclic alkyl or alkenyl groups; and provided that at least one P group satisfies formula (II) as defined above;
e) X independently of one another represents a functional group selected from the group consisting of the formulae i) to xiv):
wherein the wavy line is as defined above, the bold line indicates the position of the bond between X and G, and R 5 Represents hydrogen atom, C 1 To C 22 Saturated or unsaturated alkyl or aryl groups of (2), possibly substituted with C 1 To C 6 An alkyl or alkoxy group or a halogen atom; and provided that X may not be present when P represents a hydrogen atom;
f) G represents a polyvalent group (having a valence of m+1) derived from a cyclic, linear, alicyclic or branched alkyl group having 1 to 22 carbon atoms, a cyclic, linear, alicyclic or branched alkenyl group, a phenyl group, an alkylphenyl group or an alkenylphenyl hydrocarbon group which may have a substituent and contain 1 to 10 functional groups selected from the group consisting of halogens, alcohols, ethers, esters, ketones, aldehydes, carboxylic acids, thiols, thioethers, amines, quaternary amines and amides; and is also provided with
g) Q represents a hydrogen atom (w=1 and n=1 in this case), or represents a polymer or copolymer selected from the group consisting of poly (alkylimine), a peptide (e.g. polylysine) or a polysaccharide selected from cellulose, cyclodextrin and starch, or a cationic quaternized silicon polymer, or a polymer or random copolymer derived from monomer units selected from the group consisting of formulae a-1), a-2), a-3), B-1), B-2), C-1), C-2), and C-3):
Wherein hatching indicates the position of the bond between the monomer unit and G;
y represents oxygen or sulfur atom or NR 7 A group;
o, p, q, r, s, t, u and v each independently of the other represent a fraction between 0 and 1, with o+p+q=1, r+s=1 and t+u+v=1, with the proviso that o or p, and r and t are not equal to 0;
R 6 represents a hydrogen atom or is derived from natural or unnatural amino acids, e.g. glycine, alanine, phenylalanine, argininSide chains of acid, histidine, lysine, aspartic acid, glutamic acid, cysteine, methionine, glutamine, asparagine, threonine, serine, leucine, isoleucine, valine, tyrosine or tryptophan;
R 7 at the same time or independently represent a hydrogen atom or C 1 -C 16 A hydrocarbon group;
R 8 simultaneously or independently of one another:
-a hydrogen or halogen atom;
-C 1 -C 6 a hydrocarbyl group optionally containing 1 to 4 heteroatoms selected from the group consisting of oxygen and sulfur atoms;
-a carboxyl group of formula COOR, wherein R represents a hydrogen atom, C optionally containing 1 to 30 oxygen atoms 1 -C 60 Alkyl or alkenyl;
-OR 7 radicals or COR 7 A group; or alternatively
-pyrrolidone units linked by nitrogen atoms; and is also provided with
M represents a hydrogen atom, an alkali metal or alkaline earth metal ion.
The present invention relates to a textile article comprising a pro-fragrance compound of formula (I).
In a particular embodiment, the textile article is suitable for use in drum drying.
In a particular embodiment, the textile article is a drum dryer sheet, dryer bulb, dryer pouch or wipe. Preferably, the textile product is a drum-dried sheet.
In a particular embodiment, a textile article includes a textile carrier layer and a nonwoven fabric coating.
The textile carrier layer represents the basic structure of the textile article and comprises, preferably consists of, a woven fabric (nonwoven fabric) and/or a nonwoven fabric (non-woven fabric).
Preferably, the textile carrier layer comprises, preferably consists of, nonwoven. The nonwoven may comprise a bonded or filament-like product having a web or carded fibrous structure in which the fiber strength is suitable for carding, or alternatively, may comprise a fibrous mat in which the fibers or filaments are randomly distributed or in random array form (i.e., an array of fibers in the form of a carded web in which there is often a partial orientation of the fibers, as well as a fully random distributed orientation), or be substantially aligned. The fibers or filaments may be natural (e.g., wool, silk, jute, hemp, cotton, flax, sisal, or ramie) or synthetic (e.g., rayon, cellulose esters, polyethylene derivatives, polyolefins, polyamides, or polyesters). The nonwoven carrier layer may be manufactured by any method that is easily selected by a person skilled in the art. Examples include the methods disclosed in U.S. patent 5,246,603.
The textile carrier layer may be configured to provide desired physical properties such as, for example, absorbency, tensile strength, thickness, and the like. For example, the desired absorbency may be achieved by cumulatively increasing the thickness of the textile carrier layer, i.e., by stacking multiple carded webs or pads to a thickness sufficient to achieve the necessary absorbency properties, or by allowing fibers of sufficient thickness to be deposited on a screen.
By nonwoven coating is meant a coating that covers at least part of the surface of the textile carrier layer, preferably the entire surface of the textile carrier layer. The nonwoven coating is not textile-based, i.e. it does not comprise woven and/or nonwoven fabrics.
Preferably, the weight of the coating is 43 to 75 weight percent based on the total weight of the textile article.
In a particular embodiment, the nonwoven fabric coating comprises a softening agent. Preferably, the softening agent is methyl bis [ tallow) ethyl ] -2-hydroxyethyl ammonium methyl sulfate.
In a particular embodiment, the pro-fragrance compound of formula (I) is present in a textile carrier layer and/or a non-textile coating.
Preferably, the pro-fragrance compound according to formula (I) is present at least in the non-woven fabric coating, more preferably the pro-fragrance compound according to formula (I) is present only in the coating. Thus, the pro-fragrance compound according to formula (I) may be present on the surface of the non-woven fabric coating and/or within the coating, i.e. the pro-fragrance compound may be incorporated into the coating.
In this regard, the pro-fragrance compound may be sprayed onto the outermost surface of the coating to effect the presence of the pro-fragrance compound on the surface of the coating.
Furthermore, the pro-fragrance compound may be incorporated into the coating by, for example, adding the pro-fragrance compound to the coating in molten form, after which the coating is applied to the textile carrier layer.
According to the invention, the textile article comprises a pro-fragrance compound of formula (I).
A pro-fragrance or fragrance precursor is a compound capable of releasing one, two or more fragrance compounds, also known as PRMs (perfume raw materials), under external influence, thereby prolonging the perfuming effect of the PRMs. The release of one or more fragrance compounds is based on cleavage of chemical bonds in the pro-fragrance compound.
In a particular embodiment, the pro-fragrance compound of formula (I) releases one, two or three fragrance compounds. Preferably, the pro-fragrance compound of formula (I) releases a fragrance compound.
A "perfume compound" or "perfume raw material" is a compound that is used as an active ingredient in a perfuming formulation or composition to impart a hedonic effect; i.e. its main purpose is to impart or regulate a pleasant smell. In other words, the compounds to be considered as perfuming ingredients must be recognized by a person skilled in the art of perfumery as being able to impart or modify in an active or pleasant way the odor of a composition, not just as having an odor.
The external effect that triggers the release of the fragrance compound from the pro-fragrance compound of formula (I) may be exposure to light, air (ambient air)/oxygen, heat, moisture or enzymes.
"light" refers to any form of electromagnetic radiation, not limited to any particular wavelength. The release of PRMs from pro-fragrance compounds is generally more efficient at lower wavelengths (higher energy input).
In a particular embodiment, the pro-fragrance compound of formula (I) releases the fragrance compound by exposure to light.
For the sake of clarity, the expression "ambient air" or similar means the normal meaning understood by the person skilled in the art, i.e. oxidation takes place at room temperature, air and atmospheric pressure. In other words, the environment in which the compound is oxidized is air. It will be appreciated that the pro-fragrance is oxidized in ambient air. In particular, it is understood that the pro-fragrance does not necessarily require a pure oxygen environment, heat or a catalyst for oxidation.
In a particular embodiment, the pro-fragrance compound of formula (I) releases the fragrance compound by exposure to air (ambient air)/oxygen.
"heat" refers to any energy input caused by an elevated temperature. The temperature to be applied is not limited to a specific temperature range but depends on the individual pro-fragrances. It is within the knowledge of the skilled person to determine the appropriate temperature.
In a particular embodiment, the pro-fragrance compound of formula (I) releases the fragrance compound by exposure to heat.
The external impact that triggers the release of the PRM by the pro-fragrance compound may also be based on exposure to moisture (humidity). This requires that the pro-fragrance compound exhibit chemical bonds that are susceptible to water-induced cleavage. It is within the knowledge of one skilled in the art to identify pro-fragrance compounds having chemical bonds that are susceptible to water-induced cleavage.
In a particular embodiment, the pro-fragrance compound of formula (I) releases the fragrance compound by exposure to moisture.
The external impact that triggers the release of PRM by the pro-fragrance compound may also be based on exposure to one or more enzymes. This requires that the pro-fragrance compound exhibit chemical bonds that are capable of efficient cleavage in the presence of the enzyme. It is within the knowledge of the skilled person to determine which chemical bonds can be efficiently cleaved by a certain type of enzyme.
In a particular embodiment, the pro-fragrance compound of formula (I) releases the fragrance compound by exposure to one or more enzymes.
In a particular embodiment, the pro-fragrance compound promotes the release of the fragrance raw material based not only on one type of external influence as described above, but also on two or more of the above external influences, either simultaneously or independently of each other. However, for each pro-fragrance compound there is typically one or two types of release mechanisms, which are particularly effective or advantageous compared to other types that can be envisaged in theory. It is well within the knowledge of the skilled person to determine the main type of release mechanism of the existing pro-fragrances.
In a particular embodiment, the textile article comprises a pro-fragrance compound according to formula (I) that releases a fragrance compound upon exposure to air (ambient air)/oxygen and moisture.
In a particular embodiment, the textile article comprises at least one other pro-fragrance compound than the pro-fragrance compound according to formula (I). Thus, the textile article may comprise one, two, three, four, five or more other pro-fragrance compounds in addition to the pro-fragrance compound according to formula (I). The one or more other pro-fragrance compounds may also be pro-fragrance compounds falling within the formula (I). Other pro-fragrance compounds the PRM may be released by the same release mechanism as the pro-fragrance compound according to formula (I) or by another release mechanism. Under the release mechanism, external influences are understood to trigger the release of PRMs from the above-mentioned pro-fragrance compounds. Preferably, the at least one other pro-fragrance compound is selected from the group consisting of: 2-phenylethyl oxo (phenyl) acetate, 3, 7-dimethyloct-2, 6-dien-1-yl oxo (phenyl) acetate, 3, 7-dimethyl-2, 6-octadien-1-yl hexadecanoate, 3, 7-dimethyl-2, 6-octadien-1-yl succinate, bis (3, 7-dimethyloct-2, 6-dien-1-yl) succinate, hexadecanoate (2E, 6Z) -2, 6-nonadienyl ester, tetradecanoate (2E, 6Z) -2, 6-nonadien-1-yl ester, dodecanoic acid (2E, 6Z) -2, 6-nonadien-1-yl ester, (2- ((2-methylundec-1-en-1-yl) oxy) ethyl) benzene, 1-methoxy-4- (3-methyl-4-phenethoxy-3-en-1-yl) benzene, 1-methyl-2-nonadien-1-yl, 1-yl) undecano-2-1-yl, 2-methyl-1- (oct-3-yloxy) undec-1-ene, 1-methoxy-4- (1-phenethylen-1-en-2-yl) benzene, 1-methyl-4- (1-phenethylen-1-en-2-yl) benzene, 2- (1-phenethylen-1-en-2-yl) naphthalene, (2-phenethylenyl) benzene, 2- (1- ((3, 7-dimethyloct-6-en-1-yl) oxy) prop-1-en-2-yl) naphthalene, (2- ((2-pentylidene) methoxy) ethyl) benzene, 4-allyl-2-methoxy-1- ((2-phenylvinyl) oxy) benzene, (2- ((2-heptylethylen) methoxy) ethyl) benzene, 1-methoxy-4- (1-phenethylen-1-yl) benzene, (2- ((2-methyl-4- (2, 6-trimethylcyclohex-1-en-1-yl) but-1-yl) oxy) ethyl) benzene, 1-methoxy-4- (2-methyl-3-phenethoxyallyl) benzene, (2- ((2-isopropyl-5-methylcyclohexylidene) methoxy) ethyl) benzene, 1-isopropyl-4-methyl-2- ((2-pentylidene) methoxy) benzene, 2-methoxy-1- ((2-pentylidene) methoxy) -4-propylbenzene, 2-ethoxy-1- ((2-methoxy-2-phenylvinyl) oxy) -4-methylbenzene, 3-methoxy-4- ((2-methoxy-2-phenylvinyl) oxy) benzaldehyde, 1-isopropyl-2- ((2-methoxy) -2-phenylvinyl) oxy) -4-methylbenzene, 4- ((2- (hexyloxy) -2-phenylvinyl) oxy) -3-methoxybenzaldehyde, or a mixture thereof.
In a particular embodiment, X represents a functional group selected from the group consisting of formula ii), formula iii), formula viii), formula ix) and formula xiv). In a particular embodiment, X represents a functional group of formula ii).
The expression "odoriferous α, β -unsaturated ketone, aldehyde or carboxylate" as used in the definition of P is understood to mean an α, β -unsaturated ketone, aldehyde or carboxylate which is recognized by the person skilled in the art as being used as a perfuming ingredient in the perfumery industry. In general, the odorous α, β -unsaturated ketone, aldehyde or carboxylic acid ester is a compound having 8 to 20 carbon atoms, or even more preferably 10 to 15 carbon atoms.
Similarly, it is not possible to provide an exhaustive list of the currently known odoriferous compounds which can be used to synthesize the pro-fragrance compounds of formula (I) as defined above and which are subsequently released. However, the following may be named as preferred examples: alpha-damascenone, beta-damascenone, gamma-damascenone, delta-damascenone, 1- [ 6-ethyl-2, 6-dimethyl-3-cyclohexen-1-yl ] -2-buten-1-one, alpha-ionone (ionone, aromatic cordierite), beta-ionone, gamma-ionone, delta-ionone, beta-damascenone Ma Xitong, 2-methyl-1- (2, 6-trimethylcyclohex-3-en-1-yl) but-2-en-1-one, 1- [ 6-ethyl-2, 6-dimethyl-3-cyclohexen-1-yl ] -2-buten-1-one, 3-methyl-5-propyl-2-cyclohexen-1-one, 2-methyl-5- (1-propen-2-yl) -2-cyclohexen-1-one, 2, 5-dimethyl-5-phenyl-1-hexen-3-one, 1- (5, 5-dimethyl-1-cyclohexen-1-yl) -4-dien-1-one, alpha-8-methyl-2-octen-1-one, 1- (2, 3, 6-tetramethylcyclohexyl) but-2-en-1-one, 4- (2, 3, 6-tetramethylcyclohexyl) but-3-en-2-one, 2-cyclopentadecen-1-one, 4 a-dimethyl-6- (1-propen-2-yl) -4,4a,5,6,7, 8-hexahydro-2 (3H) -naphthalenone, (E) -3-phenylprop-2-enal (cinnamaldehyde), 2, 6-trimethylspiro [ bicyclo [3.1.1] heptane-3, 1' -cyclohexane ] -2' -en-4 ' -one, ethyl 2, 4-decdienoate, ethyl 2-octenoate, methyl 2-nonenoate, ethyl 2, 4-undecanedienoate, 4-methylpent-3-en-2-one, oct-2-en-4-one, and methyl 5, 9-dimethyl-2, 4, 8-decyltriaenoate.
In a particular embodiment, P represents a group selected from the group consisting of formulas (P-1) to (P-14) in any one of the isomeric forms:
wherein the wavy line has the meaning indicated above, the dotted line represents a carbon-carbon single bond or double bond, R a Is a hydrogen atom or methyl group, R b Represents a hydrogen atom, a hydroxy group or a methoxy group or C 1 -C 4 Straight-chain or branched alkyl, and R c Represents a hydrogen atom or C 1 -C 4 Linear or branched alkyl.
In a particular embodiment, P represents a group selected from the group consisting of:
wherein the wavy line has the meaning indicated above, the dotted line represents a single bond or a double bond, R a Is a hydrogen atom or a methyl group.
In a particular embodiment, P represents a group selected from the group consisting of formula (P-1), (P-2), (P-1) ', (P-2) ', (P-3), (P-7), (P-13), (P-14) or (P-14) ' as defined above. Preferably, P represents a group selected from the group consisting of formulas (P-1), (P-1) ', (P-2) ', (P-3) or (P-14) ' as defined above.
In a particular embodiment, G may represent a divalent cyclic, linear, alicyclic or branched alkyl, alkenyl, alkadienyl or alkylbenzene group having 1 to 22 carbon atoms, which may have substituents and contain 1 to 10 functional groups selected from the group consisting of ethers, esters, ketones, aldehydes, carboxylic acids, thiols, thioethers, amines, quaternary amines and amides.
In a particular embodiment, G represents a divalent linear or branched alkyl or alkenyl hydrocarbon group having 1 to 22 carbon atoms, which may have substituents and contain 1 to 5 functional groups selected from the group consisting of ethers, esters, ketones, aldehydes, carboxylic acids, thiols, thioethers, amines, quaternary amines and amides.
In a particular embodiment, G represents a divalent linear or branched alkyl or alkenyl hydrocarbon group having 2 to 15 carbon atoms, which may have substituents and contain 1 to 2 functional groups selected from ethers and esters.
In a particular embodiment, G represents a divalent linear alkyl or alkenyl hydrocarbon group having 3 to 15 carbon atoms, which may have substituents and contain an ester function.
In a particular embodiment, G represents a divalent linear alkyl or alkenyl hydrocarbon group having 3 to 14 carbon atoms.
In a particular embodiment, Q represents a hydrogen atom or a copolymer comprising at least one repeating unit of formula B-1 as defined above.
In a particular embodiment, Q represents a hydrogen atom or a copolymer comprising at least one repeating unit of formula B-1 and at least one repeating unit of formula B-2.
In a particular embodiment, R 7 At the same time or independently represent a hydrogen atom or C 1-3 An alkyl group. Preferably, R 7 Simultaneously or independently represents a hydrogen atom or a methyl or ethyl group. More preferably, R 7 Simultaneously or independently represents a hydrogen atom or a methyl group.
In a particular embodiment, the pro-fragrance compound according to formula (I) is characterized in that:
-w＝1；n＝1；m＝1；
-P represents a group liable to generate odorous α, β -unsaturated ketones, aldehydes, and is represented by the following formula (II):
wherein R is 2 、R 3 And R is 4 Independently of one another, represent a hydrogen atom, C 6 To C 10 Aromatic ring or C 1 To C 15 Straight-chain, cyclic or branched alkyl, alkenyl or alkadienyl groups, possibly substituted by C 1 To C 4 An alkyl group; or R is 1 To R 4 Two or three of the groups are bonded together to form a group having 5 to 20 carbon atoms and including the group R 1 、R 2 、R 3 Or R is 4 Saturated or unsaturated rings of carbon atoms to which the radicals are bound, the rings possibly being substituted by C 1 To C 8 Linear, branched or cyclic alkyl or alkenyl groups;
x represents ii)
G represents a divalent radical derived from a cyclic, linear or branched alkyl, alkenyl, phenyl, alkylphenyl or alkenylphenyl hydrocarbon radical having from 2 to 8 carbon atoms, optionally containing 1 or 2 oxygen, sulfur and/or nitrogen atoms,
-Q represents a polymer or random copolymer derived from formula B-1), wherein R 7 Represents C 1 -C 16 A hydrocarbon group.
In a particular embodiment, the pro-fragrance compound according to formula (I) is a linear polysiloxane copolymer comprising at least one repeating unit of formula (III):
wherein double hatching indicates bonding to another repeat unit.
The pro-fragrances of formula (III) release 2-methyl-5- (prop-1-en-2-yl) cyclohex-2-en-1-one as a fragrance compound, which is also known as carvone. Carvone exists in the form of two enantiomers, namely (R) - (-) -2-methyl-5- (1-propen-2-yl) -2-cyclohexen-1-one (L-carvone or levocarvone) and (S) - (+) -2-methyl-5- (1-propen-2-yl) -2-cyclohexen-1-one (D-carvone or dextro-carvone). These two enantiomers are reported to have slightly different mint odor notes. However, according to the present invention, both enantiomers are expected to have similar effects in view of the preparation and release efficiency of the copolymer. According to the invention carvone may be used as racemate or as a mixture enriched in one of the two enantiomers. Preferably, a mixture enriched in levocarvone is used.
In a particular embodiment, the pro-fragrance compound corresponds to formula (IV):
wherein P has the same meaning as defined above;
g represents a divalent radical derived from a linear OR branched alkyl OR alkenyl radical having 2 to 15 carbon atoms, possibly substituted by one OR more secondary-OR groups 9 、-NR 9 2 、-COOR 9 And R is 9 A selected group among the groups, wherein R 9 Represents a hydrogen atom or C 1 To C 6 Alkyl or alkenyl; and is also provided with
Q represents a hydrogen atom.
In a particular embodiment, the pro-fragrance compound according to formula (I) is selected from the group consisting of formulas a) to d):
wherein R represents C 1 -C 20 Alkyl or alkenyl, preferably C 6 -C 15 Alkyl or alkenyl, more preferably C 12 An alkyl group.
The fragrance precursor compounds of formula a) release delta-damascenone as a fragrance compound. The pro-fragrance is preferably (+ -) -trans-3- (dodecylthio) -1- (2, 6-trimethyl-3-cyclohexen-1-yl) -1-butanone. Delta-damascenone is also known as 1- [ (1 rs,2 sr) -2, 6-trimethyl-3-cyclohexen-1-yl ] -2-buten-1-one.
The fragrance precursor compounds of formula b) or c) release ionone (coumarone) as a fragrance compound. The pro-fragrances may be present as a mixture of isomers of formulae b) and c). The isomer mixture may have a weight ratio of formula b) and formula c) of 40:60 to 60:40. In particular, the isomer mixture may have a weight ratio of formula b) and formula c) of about 55:45. In particular, the pro-fragrance releases two isomers of ionone as fragrance compounds.
In particular, the fragrance precursor compound of formula b) releases α -ionone as a fragrance compound. The pro-fragrance of formula b) is preferably (±) -4- (dodecylthio) -4- (2, 6-trimethyl-2-cyclohexen-1-yl) -2-butanone. Alpha-ionone is also known as (+ -) - (3 e) -4- (2, 6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one.
In particular, the fragrance precursor compound of formula c) releases β -ionone as a fragrance compound. The pro-fragrance of formula c) is preferably (±) -4- (dodecylthio) -4- (2, 6-trimethyl-1-cyclohexen-1-yl) -2-butanone. Beta-ionone is also known as (3E) -4- (2, 6-trimethyl-1-cyclohexen-1-yl) -3-buten-2-one.
The fragrance precursor compounds of formula d) release oct-2-en-4-one as a fragrance compound. The pro-fragrance is preferably (+ -) -2- (dodecylthio) octan-4-one. The oct-2-en-4-one may be released as its (E) -or (Z) -isomer or a mixture thereof, the (E) -isomer being preferred.
In a particular embodiment, the pro-fragrance compound according to formula (I) is selected from the group consisting of: methyl or ethyl 2- (4-oxo-4- (2, 6-trimethylcyclohex-3-en-1-yl) butan-2-ylamino) -3- (4-oxo-4- (2, 6-trimethylcyclohex-3-en-1-yl) butan-2-ylthio) propanoate, methyl or ethyl 2- (4-oxo-4- (2, 6-trimethylcyclohex-2-en-1-yl) butan-2-ylamino) -3- (4-oxo-4- (2, 6-trimethylcyclohex-2-en-1-yl) butan-2-ylthio) propanoate methyl or ethyl 2- (2-oxo-4- (2, 6-trimethylcyclohex-1-en-1-yl) butan-4-ylamino) -3- (2-oxo-4- (2, 6-trimethylcyclohex-1-en-1-yl) butan-4-ylthio) propanoate, 2- (2-oxo-4- (2, 6-trimethylcyclohex-2-en-1-yl) butan-4-ylamino) -3- (2-oxo-4- (2, 6-trimethylcyclohex-2-en-1-yl) butan-4-ylthio) propanoic acid methyl or ethyl, 3- (dodecylthio) -1- (2, 6-trimethylcyclohex-3-en-1-yl) -1-butanone, 3- (dodecylthio) -1- (2, 6-trimethylcyclohex-2-en-1-yl) -1-butanone 3- (dodecylsulfonyl) -1- (2, 6-trimethylcyclohex-3-en-1-yl) butan-1-one, 4- (dodecylthio) -4- (2, 6-trimethylcyclohex-2-en-1-yl) -2-butanone, 4- (dodecylthio) -4- (2, 6-trimethylcyclohex-1-en-1-yl) -2-butanone, 2-dodecylthio-5-methyl-heptan-4-one, 2-cyclohexyl-1-dodecylthio-hept-6-en-3-one, 3- (dodecylthio) -5-isopropenyl-2-methylcyclohexanone, 2- (dodecylthio) -4-octanone, 2- (dodecylsulfonyl) octan-4-one, 4- (dodecylthio) -4-methylpentan-2-one, N, S-bis (4-oxo-4- (2, 6-trimethylcyclohex-3-en-1-yl) butan-2-yl) -L-cysteine methyl or ethyl ester, S- (4-oxo-4- (2, 6-trimethylcyclohex-3-en-1-yl) butan-2-yl) -L-cysteine methyl or ethyl ester, 4-oxooct-2-yl dodecanoate, and any mixtures thereof.
Preferably, the pro-fragrance compound of formula (I) is selected from the group consisting of: 3- (dodecyl thio) -1- (2, 6-trimethyl cyclohexyl)Methyl-3-en-1-yl butan-1-oneD) 3- (dodecylthio) -1- (2, 6-trimethylcyclohex-2-en-1-yl) butan-1-one, 4- (dodecylthio) -4- (2, 6-trimethylcyclohex-2-en-1-yl) butan-2-one (-/-)>I) And 4- (dodecylthio) -4- (2, 6-trimethylcyclohex-1-en-1-yl) butan-2-one (>I) 2- (dodecylthio) -4-octanone, 2- (dodecylsulfonyl) oct-4-one, 4- (dodecylthio) -4-methylpentan-2-one, N, S-bis (4-oxo-4- (2, 6-trimethylcyclohex-3-en-1-yl) butan-2-yl) -L-cysteine methyl or ethyl ester, S- (4-oxo-4- (2, 6-trimethylcyclohex-3-en-1-yl) butan-2-yl) -L-cysteine methyl or ethyl ester, 4-oxooct-2-yl dodecanoate, or any mixture thereof.
More preferably, the pro-fragrance compound of formula (I) is 3- (dodecylthio) -1- (2, 6-trimethylcyclohex-3-en-1-yl) butan-1-oneD) 4- (dodecylthio) -4- (2, 6-trimethylcyclohex-2-en-1-yl) butan-2-one (->I) 4- (dodecylthio) -4- (2, 6-trimethylcyclohex-1-en-1-yl) butan-2-one ( >I) Or mixtures thereof.
Still more preferably, the pro-fragrance compound of formula (I) is 3- (dodecylthio) -1- (2, 6-trimethylcyclohex-3-en-1-yl) butan-1-oneD) 4- (dodecylthio) -4- (2, 6-trimethylcyclohex-2-en-1-yl) butan-2-one (->I) And 4- (dodecylthio) -4- (2, 6-trimethylcyclohex-1-en-1-yl) butan-2-one (>I) Is a mixture of (a) and (b).
Most preferably, the pro-fragrance compound of formula (I) is 3- (dodecylthio) -1- (2, 6-trimethylcyclohex-3-en-1-yl) butan-1-oneD) And 4- (dodecylthio) -4- (2, 6-trimethylcyclohex-1-en-1-yl) butan-2-one (>I) Is a mixture of (a) and (b).
In a particular embodiment, the pro-fragrance compound is not included in the textile article based on deposition of the pro-fragrance compound during the washing process.
In a particular embodiment, the pro-fragrance compound according to formula (I) is unencapsulated. Unencapsulated means that the pro-fragrance compound according to formula (I) is not encapsulated in a polymeric carrier material prior to addition to the textile article according to the invention.
In a particular embodiment, the pro-fragrance compound according to formula (I) is dissolved in a solvent before being added to the textile article. Examples of suitable solvents are butanediol or propylene glycol, glycerol, dipropylene glycol and monoethers thereof, 1,2, 3-propanediol triacetate, dimethyl glutarate, dimethyl adipate, 1, 3-diacetoxypropyl-2-yl acetate, diethyl phthalate, isopropyl myristate, benzyl benzoate, benzyl alcohol, 2- (2-ethoxyethoxy) -1-ethanol, triethyl citrate, ethanol, water/ethanol mixtures, limonene or other terpenes, isoparaffins, for example under the trade name Those known (source: exxon Chemical), or glycol ethers and glycol ether esters, e.g. under the trademark +.>Those known (source: dow Chemical Company), or hydrogenated castor oil, for example under the trademark +.>Those known as RH 40 (source: BASF), or mixtures thereof. Thus in this embodiment, the textile article also comprises such a solvent.
The textile article comprises the pro-fragrance compound in an amount of 0.000086 to 1.875 wt%, preferably 0.000086 to 1.5 wt%, more preferably 0.000086 to 1 wt%, even more preferably 0.000086 to 0.75 wt%, yet even more preferably 0.001 to 0.375, most preferably 0.0172 to 0.1875 wt%, based on the total weight of the textile article.
In a particular embodiment, the pro-fragrance compound according to formula (I) is present in the non-woven coating, wherein the pro-fragrance compound is present in the coating in an amount of 0.0002 to 2.5 wt%, preferably in an amount of 0.0002 to 1 wt%, more preferably in an amount of 0.04 to 0.25 wt%, based on the total weight of the coating.
In a particular embodiment, the textile article further comprises a perfuming composition comprising:
i) At least one ingredient selected from the group consisting of a fragrance carrier and a fragrance base; and
ii) optionally, at least one fragrance adjuvant.
By "perfume carrier" is meant herein a material that is practically neutral from a perfume point of view, i.e. does not significantly alter the organoleptic properties of the perfuming ingredients. The carrier may be a liquid or a solid.
As liquid carriers, mention may be made, as non-limiting examples, of emulsifying systems, i.e. solvents and surfactantsA dosage system, or a solvent commonly used in perfumery. A detailed description of the nature and type of solvents commonly used in perfumery is not exhaustive. However, as non-limiting examples, solvents such as butanediol or propylene glycol, glycerol, dipropylene glycol and monoethers thereof, 1,2, 3-propanediol triacetate, dimethyl glutarate, dimethyl adipate, 1, 3-diacetoxypropyl-2-yl acetate, diethyl phthalate, isopropyl myristate, and the like can be cited,(rosin resins, available from Eastman), benzyl benzoate, benzyl alcohol, 2- (2-ethoxyethoxy) -1-ethanol, triethyl citrate or mixtures thereof, which are the most commonly used or naturally derived solvents such as glycerol or various vegetable oils such as palm oil, sunflower oil or linseed oil. For compositions comprising both a perfume carrier and a perfume base, other suitable perfume carriers may be ethanol, water/ethanol mixtures, limonene or other terpenes, isoparaffins, e.g. under the trademark Those well known (source: exxon Chemical), or glycol ethers and glycol ether esters, e.g. under the trademarkThose known (sources: dow Chemical Company), or hydrogenated castor oil, e.g. under the trade markThose known for RH 40 (source: BASF).
By solid carrier is meant a material to which the perfuming composition or some of the ingredients of the perfuming composition can be chemically or physically combined. Typically, such solid carriers are used to stabilize the composition, or to control the evaporation rate of the composition or certain ingredients. Solid supports are currently used in the art and the person skilled in the art knows how to achieve the desired effect. However, as non-limiting examples of solid carriers, there may be mentioned absorbent gums or polymers or inorganic materials, such as porous polymers, cyclodextrins, wood based materials, organic or inorganic gels, clays, gypsum, talc or zeolites.
As other non-limiting examples of solid carriers, encapsulating materials may be cited. Examples of such materials may include wall forming materials and plasticising materials such as glucose syrup, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetate, polyvinyl alcohol, proteins or pectins, vegetable gums such as acacia (gum arabic), urea, sodium chloride, sodium sulphate, zeolite, sodium carbonate, sodium bicarbonate, clay, talc, calcium carbonate, magnesium sulphate, gypsum, calcium sulphate, magnesium oxide, zinc oxide, titanium dioxide, calcium chloride, potassium chloride, magnesium chloride, zinc chloride, carbohydrates, sugars such as sucrose, mono-, di-, tri-and polysaccharides and derivatives such as chitosan, starch, cellulose, carboxymethyl methylcellulose, hydroxyethyl cellulose, ethylcellulose, propylcellulose, polyols/sugar alcohols such as sorbitol, maltitol, xylitol, erythritol and isomalt, polyethylene glycol (PEG), polyvinylpyrrolidone (PVP), polyvinyl alcohol, acrylamide, acrylic acid esters, polyacrylic acid and related substances, maleic anhydride copolymers, amine functional polymers, vinyl ethers, styrene, polystyrene sulfonates, vinyl acids, ethylene glycol-propylene glycol block copolymers, vegetable gums, acacia gums, pectins, xanthan gums, alginates, carrageenans, citric acid or any water-soluble solid acids, fatty alcohols or fatty acids and mixtures thereof, or in references such as h.scherz, hydrokolide: stabilisatoren, dickungs-und Geliermittel in Lebensmitteln, band 2der Schriftenreihe Lebensmittelchemie, Behr's Verlag GmbH&Co., hamburg, 1996. Encapsulation is a well known method to those skilled in the art and may be performed, for example, by using techniques such as spray drying, agglomeration or extrusion; or encapsulated by a coating including coacervation and complex coacervation techniquesComposition is prepared.
As non-limiting examples of solid supports, mention may be made in particular of core-shell capsules using resins of the aminoplast, polyamide, polyester, polyurea or polyurethane type or mixtures thereof (all of which are known to the person skilled in the art), phase separation processes initiated by using polymerization, interfacial polymerization, coacervation, etc. techniques or by these techniques together (all of which have been described in the prior art), and optionally in the presence of polymeric stabilizers or cationic copolymers.
Resins can be produced by polycondensation of aldehydes (e.g., formaldehyde, 2-dimethoxyacetaldehyde, glyoxal, glyoxylic acid or glycolaldehyde and mixtures thereof) with amines such as urea, benzoguanamine, gan Niaoji, melamine, methylolmelamine, methylated methylolmelamine, guanazol, and the like, and mixtures thereof. Alternatively, preformed resinous alkylated polyamines, e.g., under the trademark (source: cytec Technology Corp.), -a->(source: cytec Technology Corp.), -a->Or->(source: BASF) are commercially available.
Other resins are those obtained by polymerizing a polyhydric alcohol such as glycerin with a polyisocyanate such as hexamethylene diisocyanate, isophorone diisocyanate or a trimer of xylylene diisocyanate or biuret of hexamethylene diisocyanate, or a trimer of xylylene diisocyanate with trimethylolpropane (under the trade nameThe source is known: mitsui ChemicalsAmong them, biuret of xylylene diisocyanate with trimer of trimethylolpropane and hexamethylene diisocyanate is preferable.
Some research literature relating to the encapsulation of fragrances by polycondensation of amino resins, i.e. melamine based resins, with aldehydes includes articles such as Acta polymers published by k.dietrich et al, 1989,vol.40,pages 243,325 and 683 and 1990,vol.41,page 91. These articles have described various parameters affecting the preparation of such core-shell microcapsules according to prior art methods, which are also further detailed and exemplified in the patent literature. US 4'396'670 of Wiggins Teape Group Limited is a related early example of the latter. Since then, many other authors have enriched the literature in this area, not all published developments being possible here, but the general knowledge of encapsulation technology is very important. More recent targeted publications also relate to suitable uses of such microcapsules, for example by H.Y.Lee et al, articles Journal of Microencapsulation,2002,vol.19,pages 559-569, international patent publication WO01/41915 or S. And the article Chimia,2011,vol.65,pages 177-181 by et al.
The term "perfume base" is understood to mean a composition comprising at least one perfume compound. The perfume compounds have the same meaning as defined above. The pro-fragrance compounds are not considered fragrance compounds.
The nature and type of the perfume compounds present in the base do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them according to his general knowledge and to the intended use or application and the desired organoleptic effect. In general, these perfuming co-ingredients belong to different chemical classes as varied as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenes, nitrogen-or sulfur-containing heterocyclic compounds and essential oils, and the perfuming co-ingredients can be of natural or synthetic origin.
Examples of fragrance compounds commonly used in fragrance formulations are:
aldehyde fragrance component: decanal, dodecanal, 2-methylundecnal, 10-undecnal, octanal, nonanal and/or nonenal;
aromatic herbal ingredients: eucalyptus oil, camphor, eucalyptol, 5-methyltricyclo [ 6.2.1.0-2, 7- ] undec-4-one, 1-methoxy-3-hexanethiol, 2-ethyl-4, 4-dimethyl-1, 3-oxathiane (oxathiane), 2,7/8, 9/10-tetramethylspiro [5.5] undec-8-en-1-one, menthol and/or alpha-pinene;
Balsam component: coumarin, ethyl vanillin and/or vanillin;
citrus aroma component: dihydromyrcenol, citral, orange oil, linalyl acetate, citronellonitrile, orange terpene, limonene, 1-p-menthen-8-yl acetate and/or 1,4 (8) -p-menthadiene;
floral components: methyl dihydrojasmonate, linalool, citronellol, phenethyl alcohol, 3- (4-tert-butylphenyl) -2-methylpropionaldehyde, hexylcinnamaldehyde, benzyl acetate, benzyl salicylate, tetrahydro-2-isobutyl-4-methyl-4 (2H) -pyranol, beta-ionone (beta-citronellone), methyl 2- (methylamino) benzoate, (E) -3-methyl-4- (2, 6-trimethyl-2-cyclohexen-1-yl) -3-buten-2-one (1E) -1- (2, 6-trimethyl-2-cyclohexen-1-yl) -1-penten-3-one, 1- (2, 6-trimethyl-1, 3-cyclohexadien-1-yl) -2-buten-1-one, (2E) -1- (2, 6-trimethyl-2-cyclohexen-1-yl) -2-buten-1-one, (2E) -1- [2, 6-trimethyl-3-cyclohexen-1-yl ] -2-buten-1-one, (2E) -1- (2, 6-trimethyl-1-cyclohexen-1-yl) -2-buten-1-one, 2, 5-dimethyl-2-indanmethanol, 2, 6-trimethyl-3-cyclohexene-1-carboxylate, 3- (4, 4-dimethyl-1-cyclohexen-1-yl-propanal, hexyl salicylate, 3, 7-dimethyl-1, 6-nonadien-3-ol, 3- (4-isopropylphenyl) -2-methylpropanaldehyde, tricyclodecenyl acetate, geraniol, p-mentha-1-en-8-ol, 4- (1, 1-dimethylethyl) -1-cyclohexyl acetate, 1-dimethyl-2-phenylethyl acetate, 4-cyclohexyl-2-methyl-2-butanol, amyl salicylate, methyl high cis-dihydrojasmonate 3-methyl-5-phenyl-1-pentanol, tricyclodecenyl propionate, geranyl acetate, tetrahydrolinalool, cis-7-p-menthol, (S) -2- (1, 1-dimethylpropoxy) propyl propionate, 2-methoxynaphthalene, 2-trichloro-1-phenylethyl acetate, 4/3- (4-hydroxy-4-methylpentyl) -3-cyclohexene-1-carbaldehyde, pentylmennaldehyde, 8-decen-5-olide, 4-phenyl-2-butanone, isononyl acetate, 4- (1, 1-dimethylethyl) -1-cyclohexyl acetate, tricyclodecenyl isobutyrate, and/or a mixture of methyl ionone isomers;
The fruit fragrance comprises the following components: gamma-undecalactone, 2, 5-trimethyl-5-pentylcyclopentanone, 2-methyl-4-propyl-1, 3-oxathiane, 4-decalactone, ethyl 2-methyl-pentanoate, hexyl acetate, ethyl 2-methylbutanoate, gamma-nonolactone, allyl heptanoate, 2-phenoxyethyl isobutyrate, ethyl 2-methyl-1, 3-dioxolane-2-acetate, diethyl 3- (3, 3/1, 1-dimethyl-5-indanyl) propanal, diethyl 1, 4-cyclohexanedicarboxylate, 3-methyl-2-hexen-1-yl acetate, [ 3-ethyl-2-oxiranyl ] acetic acid 1- [3, 3-dimethylcyclohexyl ] ethyl ester and/or diethyl 1, 4-cyclohexanedicarboxylate;
green fragrance component: 2-methyl-3-hexanone (E) -oxime, 2, 4-dimethyl-3-cyclohexene-1-carbaldehyde, 2-tert-butyl-1-cyclohexyl acetate, styryl acetate, allyl (2-methylbutoxy) acetate, 4-methyl-3-decen-5-ol, diphenyl ether, (Z) -3-hexen-1-ol and/or 1- (5, 5-dimethyl-1-cyclohexen-1-yl) -4-penten-1-one;
musk components: 1, 4-dioxa-5, 17-cyclopentadecyldione, (Z) -4-cyclopentadec-1-one, 3-methylcyclopentadecone, 1-oxa-12-cyclohexadec-2-one, 1-oxa-13-cyclohexadec-2-one, (9Z) -9-cyclohexadec-1-one, 2- { 1S) -1- [ (1R) -3, 3-dimethylcyclohexyl ] ethoxy } -2-hydroxyethyl propionate, 3-methyl-5-cyclopentadec-1-one, 1,3,4,6,7,8-hexahydro-4, 6,7, 8-hexamethylcyclopenta [ G ] -2-benzopyran, propionic acid (1S, 1 'R) -2- [1- (3', 3 '-dimethyl-1' -cyclohexyl) ethoxy ] -2-methylpropyl propionate, oxacyclohexadec-2-one and/or propionic acid (1S, 1 'R) - [1- (3', 3 '-dimethyl-1' -cyclohexyl) ethoxycarbonyl ] methyl propionate;
The costustoot comprises the following components: 1- [ (1 RS,6 SR) -2, 6-trimethylcyclohexyl]-3-hexanol, 3-dimethyl-5- [ (1R) -2, 3-trimethyl-3-cyclopenten-1-yl]-4-penten-2-ol, 3,4 '-dimethyl spiro [ ethylene oxide-2, 9' -tricyclo [6.2.1.0 ] 2,7 ]Undec [4]Alkene, (1-ethoxyethoxy) cyclododecane, acetic acid 2,2,9,11-tetramethylspiro [5.5 ]]Undec-8-en-1-yl ester, 1- (octahydro-2, 3, 8-tetramethyl-2-naphthyl) -1-ethanone, patchouli oil, terpene fraction of patchouli oil,(1 'r, e) -2-ethyl-4- (2', 2',3' -trimethyl-3 '-cyclopenten-1' -yl) -2-buten-1-ol, 2-ethyl-4- (2, 3-trimethyl-3-cyclopenten-1-yl) -2-buten-1-ol, methyl cedrone, 5- (2, 3-trimethyl-3-cyclopentenyl) -3-methylpent-2-ol, 1- (2, 3, 8-tetramethyl-1, 2,3,4,6,7,8 a-octahydronaphthalen-2-yl) ethan-1-one and/or isobornyl acetate;
other ingredients (e.g., amber, powder, spicy or watery): dodecahydro-3 a,6, 9 a-tetramethylnaphtho [2,1-b ] furan and any stereoisomers thereof, piperonal, anisaldehyde, eugenol, cinnamaldehyde, clove oil, 3- (1, 3-benzodioxol-5-yl) -2-methylpropanaldehyde, 7-methyl-2H-1, 5-benzodioxepin-3 (4H) -one, 2, 5-trimethyl-1, 2,3, 4a,5,6, 7-octahydro-2-naphthol, 1-phenylvinyl acetate, 6-methyl-7-oxa-1-thia-4-azaspiro [4.4] nonane and/or 3- (3-isopropyl-1-phenyl) butanal.
In a particular embodiment, the at least one perfume compound is selected from the group consisting of: isopropyl myristate, 1, 4-dioxaheptadecane-5, 17-dione, 1-oxa-12/13-cyclohexadec-2-one, 2- (2-methyl-2-propanyl) cyclohexyl acetate, (3Z) -3-hexen-1-yl salicylate, (2E) -2-benzyleneoctanal, 1- (1, 2, 8-tetramethyl-1, 3,4,5,6, 7-hexahydronaphthalen-2-yl) ethanone, methyl 2- ((1 RS,2 RS) -3-oxo-2-pentylcyclopentyl) acetate, 1-dimethyl-2-phenylethyl butyrate 4- (4-hydroxyphenyl) -2-butanone, allyl heptanoate, (-) - (2E) -2-ethyl-4- [ (1R) -2, 3-trimethyl-3-cyclopenten-1-yl ] -2-buten-1-ol, 3-ethoxy-4-hydroxybenzaldehyde, 4-methoxybenzaldehyde, (+ -) -4-decalactone, (+ -) -3, 7-dimethyl-1, 6-octadien-3-ol, (+ -) -5-heptyldihydro-2 (3H) -furanone, tricyclo [5.2.1.0 (2, 6) ] dec-3/4-en-8-yl propionate, acetic acid (+ -) -1, 5-dimethyl-1-vinyl-4-hexenyl ester, (10E) -oxaheptadec-10-en-2-one, dipropylene glycol, 3-pentylthetra-2H-pyran-4-yl acetate, (+ -) - (3E) -4- (2, 6-trimethyl-1/2-cyclohexen-1-yl) -3-buten-2-one, 2-ethyl-3-hydroxy-4 (4H) -pyranone, ethyl 2-methyl-1, 3-dioxolan-2-acetate, allyl 3-cyclohexylpropionate, 1-dimethyl-2-phenylethyl acetate, 2, 4-dihydroxy-3, 6-dimethylbenzoate, β -pinene, (3E) -4- (2, 6-trimethyl-1-cyclohexen-1-yl) -3-buten-2-one, (+ -) - (2E) -1- (2, 6-trimethyl-2-cyclohexen-1-yl) -2-one, or any mixture thereof.
The at least one fragrance compound according to the invention may not be limited to the above-mentioned fragrance compounds and in any event many other such co-ingredients are listed in references such as the s.arctander works Perfume and Flavor Chemicals,1969,Montclair,New Jersey,USA, or newer versions thereof, or other works of similar nature, and in the patent literature which is abundant in the fragrance industry.
The term "perfume adjuvant" is understood to mean an ingredient capable of imparting additional benefits, such as color, specific light fastness, chemical stability, etc. A detailed description of the nature and type of adjuvants commonly used in perfuming bases cannot be exhaustive, but it must be mentioned that said ingredients are well known to a person skilled in the art. However, the following may be cited as specific non-limiting examples: viscosity agents (e.g., surfactants, thickeners, gelling agents, and/or rheology modifiers), stabilizers (e.g., preservatives, antioxidants, thermal/optical and/or buffering agents or chelating agents, such as BHT), colorants (e.g., dyes and/or pigments), preservatives (e.g., antimicrobial or antifungal or anti-irritant agents), abrasives, skin coolants, fragrance fixatives, insect repellents, ointments, vitamins, and mixtures thereof.
In a particular embodiment, the at least one perfume compound is encapsulated. The at least one perfume compound may be encapsulated, for example, in core-shell microcapsules. It will be appreciated that not only a single fragrance compound may be encapsulated within one microcapsule, but also a mixture of fragrance compounds may be encapsulated within one microcapsule.
Suitable materials for encapsulating fragrance compounds have been widely described in the prior art. As non-limiting examples, the microcapsule shell may be aminoplast-based, polyurea-based, or polyurethane-based.
In a particular embodiment, the perfuming composition is present in a textile carrier layer and/or a non-textile coating. Preferably, the perfuming composition is present in the nonwoven fabric coating. Preferably, the perfuming composition is incorporated into the nonwoven coating.
In a particular embodiment, the textile article further comprises at least one agent selected from the group consisting of antistatic agents, dye transfer inhibitors, brighteners, enzymes, soil repellants, anti-wrinkle agents, and fabric softening agents.
The fabric softener may comprise cationic nitrogen-containing compounds, such as quaternary ammonium compounds. In general, fabric softeners may include suitable cationic, anionic, nonionic and zwitterionic compounds. Suitable fabric softeners are well known to the skilled person.
Antistatic agents can minimize or eliminate charge build-up. Examples of antistatic agents are quaternary ammonium salts, aliphatic amines, phosphoric acid esters and ethylene glycol.
Dye transfer inhibition is an agent that prevents the transfer of dye from one textile article to another. Dye transfer inhibition agents are mainly polymers, present in various substances; for example, polyvinylpyrrolidone or polyimidazole may be used.
In addition, the skilled person is aware of suitable brighteners, enzymes, antifouling agents, anti-wrinkle agents which may further be present in the textile product.
In a particular embodiment, the textile article further comprises a protective overprint layer located outermost of the nonwoven fabric coating. The protective overprint layer may comprise a PEG (polyethylene glycol) solution, where the concentration of the PEG solution may be 60% in water.
Another aspect of the invention relates to a method for preparing a textile article according to the invention, comprising the step of adding an effective amount of a pro-fragrance compound according to formula (I) to the textile article.
In a particular embodiment, an effective amount of the pro-fragrance compound means that the amount of the pro-fragrance compound is 0.000086 to 1.875 wt%, preferably 0.000086 to 1.5 wt%, more preferably 0.000086 to 1 wt%, even more preferably 0.000086 to 0.75 wt%, still even more preferably 0.001 to 0.375, most preferably 0.0172 to 0.1875 wt%, based on the total weight of the textile article.
In a particular embodiment, the pro-fragrance compound according to formula (I) is incorporated into a textile carrier layer of a textile article.
In a particular embodiment, the pro-fragrance compound according to formula (I) is incorporated into a non-woven fabric coating and/or applied to the surface of the coating.
Preferably, the pro-fragrance compound according to formula (I) is incorporated into a non-woven fabric coating.
When incorporating the pro-fragrance compound into the non-woven fabric coating, the pro-fragrance compound is preferably added to the coating, after which the coating comprising the pro-fragrance compound is applied to the surface of the textile carrier layer. This can be accomplished, for example, by melting the coating and adding the pro-fragrance compound to the melt.
When the pro-fragrance compound is applied to the surface of the nonwoven fabric coating, the pro-fragrance compound is preferably sprayed onto the surface of the coating.
In a particular embodiment, the method further comprises the step of applying a protective overprint layer outermost to the nonwoven fabric coating. Preferably, the protective overprint layer comprises a PEG (polyethylene glycol) solution.
In a particular embodiment, the method further comprises the step of adding at least one agent selected from the group consisting of antistatic agents, dye transfer inhibitors, brighteners, enzymes, anti-soil agents, anti-wrinkle agents, and fabric softening agents. The agent may be incorporated into the textile carrier layer, the nonwoven fabric coating and/or applied to the surface of the coating.
In a particular embodiment, the pro-fragrance compound is not added to the textile article by a washing process. In other words, the pro-fragrance is not added to the textile article by deposition of pro-fragrance compounds onto the textile article during the washing process.
Another aspect of the invention relates to the use of a textile article according to the invention for improving, enhancing, giving and/or modifying the fragrance impression and/or fragrance intensity of garments during tumble drying.
The undergarment, each piece of cloth or laundry can be dried in the tumble dryer.
In a particular embodiment, the drum drying is carried out at a temperature of 45 to 70 ℃.
In a particular embodiment, the pro-fragrance of formula (I) is transferred from the textile article to the garment during drum drying. As a result, the pro-fragrance of formula (I) adheres to the drum-dried garment.
Another aspect of the invention relates to a method for improving, enhancing, imparting and/or modifying a fragrance impression and/or fragrance intensity of a garment, comprising the step of adding a textile article according to the invention to the garment during tumble drying.
Examples
Example 1
Preparation of a perfuming composition comprising a pro-fragrance:
The perfuming compositions were prepared by mixing the ingredients of table 1 below:
as pro-fragrance compounds, the perfuming compositions comprise 3- (dodecylthio) -1- (2, 6-trimethylcyclohex-3-en-1-yl) butan-1-one, 4- (dodecylthio) -4- (2, 6-trimethyl-1-cyclohex-1-yl) -2-butanone and 4- (dodecylthio) -4- (2, 6-trimethylcyclohex-2-en-1-yl) butan-2-one.
Preparation of flavored drum dried tablets:
methyl bis [ ethyl tallowate ] -2-hydroxyethyl methyl ammonium sulfate (softening active) was melted at 65 ℃ and the perfuming composition according to table 1 was incorporated into the melt at 5% by weight with stirring. The melt mixture was then applied uniformly to the surface of a precut nonwoven sheet (sheet weight of 0.65 g) fixed on a hot plate. The total amount of melt coated on the nonwoven was 1.3g. Thus, the total weight of the final perfumed drum dried tablet was 1.95g.
Washing and drying cycle:
cotton towels (25 pieces, each of about 33cm x 33cm in size and weighing about 50g each) were washed with unflavoured detergent (50 g) in a universal electrically stackable washer/dryer in a light white/medium setting.
The towels are then dried with either unflavored dry tablets or flavored dry tablets. The perfumed dry tablet is the dry tablet described above, comprising the perfuming composition according to table 1. After drying, the towels are stored in a box. Dry towel samples were randomly and blindly coded. The screened and experienced panelists were then instructed to evaluate the overall fragrance intensity of each sample (towel) on an unlabeled continuous linear scale, with 0 = no noticeable odor and 10 = very strong odor.
Sensory evaluation was performed at three time points (after 14 days, after 30 days and after 100 days). The results are shown in FIG. 1. For each time point, the towels dried using the flavored dry sheets clearly perceived a higher intensity of fragrance than the unflavored dry sheets (see fig. 1). For each time point, the left column in fig. 1 refers to the flavor intensity of the towels dried with the unflavored dry flakes, and the right column refers to the flavor intensity of the towels dried with the flavored dry flakes.
Even after drying and storage for 100 days, the towels dried with the flavored dry flakes still perceived significantly higher strength than towels dried with the unflavored dry flakes. Over such a long period of time, it can be effectively assumed that the higher fragrance intensity observed with towels dried with the perfumed dry sheet is not based solely on the presence of the fragrance compound, but rather on the presence of the pro-fragrance compounds 3- (dodecylthio) -1- (2, 6-trimethylcyclohex-3-en-1-yl) butan-1-one and 4- (dodecylthio) -4- (2, 6-trimethylcyclohex-1/2-en-1-yl) butan-2-one (as shown in Table 1), since it is expected that after such a long period of storage the conventional volatile fragrance compounds will no longer have a significant effect on the overall fragrance intensity. In contrast, the pro-fragrance compound continuously releases the fragrance compound, thereby providing a long-term fragrance impression to towels dried with the flavored dry tablets.
Example 2
A drum dried sheet was prepared as described in example 1. In the perfumed tumble dried sheet, the perfuming composition is thus contained in the non-woven fabric coating. This sample is referred to as the coating sample (C sample).
In addition, a perfumed drum-dried sheet was prepared by applying the perfuming composition as described in table 1 of example 1 directly onto a pre-cut nonwoven sheet (sheet weight of 0.65 g). The amount of perfuming composition added to the fabric was 0.065g, which is equal to the amount of perfuming composition present in the coating of sample C. The samples thus prepared comprise the perfuming composition in a textile carrier layer and are referred to as textile samples (tsample).
The cotton towel was washed as described in example 1 (25 pieces, each piece having dimensions of about 33cm x 33cm, each piece weighing about 50 g).
The towels were then dried with either the C or T samples as described in example 1.
After drying, the towels were stored in the cabinet for 7 days. Dry towel samples were randomly and blindly coded. The screened and experienced panelists (n=24) were then instructed to evaluate which of the dried towel samples had stronger fragrance intensity, i.e., the panelists had to decide whether the towels dried with the C sample or the towels dried with the T sample were perceived to have stronger fragrance intensity. Of the 24 panelists, 17 towel samples were selected for drying with sample C because of their stronger fragrance intensity; only 7 panelists selected towel samples dried with the T samples to have stronger fragrance intensity. Thus, it has been found that a perfumed tumble dried sheet (sample C) comprising a pro-fragrance compound in a non-woven fabric coating gives a significantly higher fragrance intensity (a level of significance of 95%) than a perfumed tumble dried sheet (sample T) comprising a pro-fragrance compound in a textile carrier layer.
Thus, it has been found that the pro-fragrance compound is particularly advantageous for fragrance delivery properties when present in a non-woven fabric coating.
Example 3
The perfumed drum dried tablets according to the invention have been prepared as described in example 1. However, instead of using the perfuming composition according to table 1, the perfuming composition according to table 2 was used as follows:
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a control drum-dried sheet was prepared in the same manner as described for the drum-dried sheet according to the present invention. However, to prepare a control tumble dry tablet, a perfuming composition according to table 2 was modified in which the pro-fragrance compound 3- (dodecylthio) -1- (2, 6-trimethylcyclohex-3-en-1-yl) butan-1-one was replaced by dipropylene glycol, i.e. the aforementioned pro-fragrance compound and the respective amounts thereof (5.5 wt.% total) had been replaced by dipropylene glycol in the perfuming composition for a control tumble dry tablet.
The drum-dried sheet according to the present invention and the control drum-dried sheet were then used twice in succession during the towel drying process to evaluate the reusability of the drum-dried sheet according to the present invention.
First wash and dry cycle:
the first set of tissues (25 pieces, each of size about 33cm x 33cm, each piece weighing about 50 g) was washed as described in example 1.
The towels were then dried as described in example 1 with a tumble dryer sheet according to the invention or a control tumble dryer sheet.
After drying, the towels were stored in the cabinet for 7 days. Dry towel samples were randomly and blindly coded. The screened and experienced panelists (n=26) were then instructed to evaluate which of the dried towel samples had stronger fragrance intensity, i.e., the panelists had to decide whether the towels dried with the drum-dried sheet according to the present invention or the towels dried with the control drum-dried sheet were perceived as stronger fragrance intensity. Of the 26 panellists, 18 selected towel samples dried with the drum-dried sheet according to the present invention had stronger fragrance intensity; only 8 panelists selected the towel samples dried with the control tumble dryer sheet to have a stronger fragrance intensity. Thus, it has been found that a tumble dried tablet according to the invention comprising a pro-fragrance compound results in a significantly higher fragrance intensity (a level of significance of 95%) compared to a control tumble dried tablet not comprising a pro-fragrance compound.
Second wash and dry cycle:
a second set of cotton towels (25 blocks, each block sized about 33cm x 33cm, each block weighing about 50 g) was washed as described in example 1.
During the drying of the second set of cotton towels, the drum drying tablets according to the invention and the control drum drying tablets were reused. Drying was performed as described in example 1.
After drying, the towels were stored in the cabinet for 7 days. Dry towel samples were randomly and blindly coded. The screened and experienced panelists (n=26) were then instructed to evaluate which of the dried towel samples had stronger fragrance intensity, i.e., the panelists had to decide whether the towels dried with the reusable roller dryer sheets according to the present invention or the towels dried with the reusable control roller dryer sheets perceived stronger fragrance intensity. Of the 26 panellists, 24 towel samples selected for drying with the drum-dried sheet according to the present invention had stronger fragrance intensity; only 2 panelists selected the towel samples dried with the control tumble dryer sheet to have a stronger fragrance intensity. Thus, it has been found that after repeated use of the drum-dried sheet, the drum-dried sheet according to the invention comprising the pro-fragrance compound results in a significantly higher fragrance intensity (a level of significance of 99%) compared to a control drum-dried sheet comprising no pro-fragrance compound.
Thus, it has been found that the drum-dried sheet according to the present invention is suitable for repeated use while still providing sufficient fragrance intensity.

Claims (15)

1. A textile article comprising a pro-fragrance compound,
wherein the pro-fragrance compound is a compound of formula (I),
wherein:
a) w represents an integer of 1 to 10000;
b) n represents 1 or 0;
c) m represents an integer of 1 to 6;
d) P represents a hydrogen atom or a group which is liable to generate an odorous alpha, beta-unsaturated ketone, aldehyde or carboxylate, and is represented by the following formula (II):
wherein the wavy line indicates the position of the bond between P and X; r is R 1 Represents hydrogen atom, C 1 To C 6 Alkoxy or C 1 To C 15 Straight, cyclic or branched alkyl, alkenyl or alkadienyl optionally substituted with 1 to 4C 1 To C 4 An alkyl group; and is also provided with
R 2 、R 3 And R is 4 Independently of one another, represents a hydrogen atom, an aromatic ring or C 1 To C 15 Straight, cyclic or branched alkyl, alkenyl or alkadienyl, possibly substituted by C 1 To C 4 An alkyl group; or R is 1 To R 4 Two or three of the groups are bonded together to form a group having 5 to 20 carbon atoms and including the group R 1 、R 2 、R 3 Or R is 4 Saturated or unsaturated rings of carbon atoms to which the radicals are bound, the rings possibly being substituted by C 1 To C 8 Linear, branched or cyclic alkyl or alkenyl groups; and provided that at least one P group satisfies the above A defined formula (II);
e) X independently of one another represents a functional group selected from the group consisting of the formulae i) to xiv):
wherein the wavy line is as defined above, the bold line indicates the position of the bond between X and G, and R 5 Represents hydrogen atom, C 1 To C 22 Saturated or unsaturated alkyl or aryl groups of (2), possibly substituted with C 1 To C 6 An alkyl or alkoxy group or a halogen atom; and provided that X may not be present when P represents a hydrogen atom;
f) G represents a polyvalent group (having a valence of m+1) derived from a cyclic, linear, alicyclic or branched alkyl group having 1 to 22 carbon atoms, a cyclic, linear, alicyclic or branched alkenyl group, a phenyl group, an alkylphenyl group or an alkenylphenyl hydrocarbon group which may have a substituent and contain 1 to 10 functional groups selected from the group consisting of halogens, alcohols, ethers, esters, ketones, aldehydes, carboxylic acids, thiols, thioethers, amines, quaternary amines and amides; and is also provided with
g) Q represents a hydrogen atom (w=1 and n=1 in this case), or represents a polymer or copolymer selected from the group consisting of poly (alkylimine), a peptide (e.g. polylysine) or a polysaccharide selected from cellulose, cyclodextrin and starch, or a cationic quaternized silicon polymer, or a polymer or random copolymer derived from monomer units selected from the group consisting of formulae a-1), a-2), a-3), B-1), B-2), C-1), C-2), and C-3):
Wherein hatching indicates the position of the bond between the monomer unit and G;
y represents oxygen or sulfur atom or NR 7 A group;
o, p, q, r, s, t, u and v each independently of the other represent a fraction between 0 and 1, with o+p+q=1, r+s=1 and t+u+v=1, with the proviso that o or p, and r and t are not equal to 0;
R 6 represents a hydrogen atom or a side chain from a natural or unnatural amino acid such as glycine, alanine, phenylalanine, arginine, histidine, lysine, aspartic acid, glutamic acid, cysteine, methionine, glutamine, asparagine, threonine, serine, leucine, isoleucine, valine, tyrosine or tryptophan;
R 7 at the same time or independently represent a hydrogen atom or C 1 -C 16 A hydrocarbon group;
R 8 simultaneously or independently of one another:
-a hydrogen or halogen atom;
-C 1 -C 6 a hydrocarbyl group optionally containing 1 to 4 heteroatoms selected from the group consisting of oxygen and sulfur atoms;
-a carboxyl group of formula COOR, wherein R represents a hydrogen atom, C optionally containing 1 to 30 oxygen atoms 1 -C 60 Alkyl or alkenyl;
-OR 7 radicals or COR 7 A group; or alternatively
-pyrrolidone units linked by nitrogen atoms; and is also provided with
M represents a hydrogen atom, an alkali metal or alkaline earth metal ion.
2. The textile article of claim 1 wherein the pro-fragrance compound of formula (I) is characterized by
-w＝1；n＝1；m＝1；
-P represents a group liable to generate odorous α, β -unsaturated ketones, aldehydes, and is represented by the following formula (II):
wherein R is 1 R is as defined in claim 1 2 、R 3 And R is 4 Independently of one another, represent a hydrogen atom, C 6 To C 10 Aromatic ring or C 1 To C 15 Straight-chain, cyclic or branched alkyl, alkenyl or alkadienyl groups, possibly substituted by C 1 To C 4 An alkyl group; or R is 1 To R 4 Two or three of the groups are bonded together to form a group having 5 to 20 carbon atoms and including the group R 1 、R 2 、R 3 Or R is 4 Saturated or unsaturated rings of carbon atoms to which the radicals are bound, the rings possibly being substituted by C 1 To C 8 Linear, branched or cyclic alkyl or alkenyl groups;
x represents ii)
G represents a divalent radical derived from a cyclic, linear or branched alkyl, alkenyl, phenyl, alkylphenyl or alkenylphenyl hydrocarbon radical having from 2 to 8 carbon atoms, optionally containing 1 or 2 oxygen, sulfur and/or nitrogen atoms,
-Q represents a polymer or random copolymer derived from formula B-1), wherein R 7 Represents C 1 -C 16 A hydrocarbon group.
3. The textile article according to claim 1 or 2, wherein either the pro-fragrance compound is selected from the group consisting of formulas a) to d):
wherein R represents C 1 -C 20 Alkyl or alkenyl;
or wherein the pro-fragrance compound is a linear polysiloxane copolymer comprising at least one repeating unit of the formula (III):
Wherein double hatching indicates bonding to another repeat unit.
4. The textile article according to any of the preceding claims, wherein the pro-fragrance compound is selected from the group consisting of: 3- (dodecylthio) -1- (2, 6-trimethylcyclohex-3-en-1-yl) butan-1-one, 2- (dodecylthio) -4-octanone, 2- (dodecylsulfonyl) oct-4-one, 3- (dodecylthio) -1- (2, 6-trimethylcyclohex-2-en-1-yl) butan-1-one, 4- (dodecylthio) -4- (2, 6-trimethylcyclohex-2-en-1-yl) butan-2-one, 4- (dodecylthio) -4- (2, 6-trimethylcyclohex-1-en-1-yl) butan-2-one, 4- (dodecylthio) -4-methylpent-2-one, N, S-bis (4-oxo-4- (2, 6-trimethylcyclohex-3-en-1-yl) butan-2-yl) -L-cysteine methyl or ethyl ester, S- (4-oxo-4- (2, 6-trimethylcyclohex-3-en-1-yl) butan-2-yl) -L-cysteine methyl or ethyl ester, 4-oxooct-2-yl dodecanoate, or any mixture thereof.
5. The textile article of any preceding claim, wherein the pro-fragrance compound is unencapsulated.
6. The textile article of any of the preceding claims, wherein the textile article comprises a textile carrier layer and a non-textile coating.
7. The textile article of claim 6, wherein the pro-fragrance compound is present in the textile carrier layer and/or the non-textile coating, preferably in the non-textile coating.
8. The textile article of any preceding claim, wherein the article comprises the pro-fragrance compound in an amount of 0.000086 to 1.875 wt%, preferably 0.001 to 0.375 wt%, more preferably 0.0172 to 0.1875 wt%, based on the total weight of the article.
9. The textile article of any preceding claim, wherein the textile article further comprises a perfuming composition comprising:
i) At least one ingredient selected from the group consisting of a fragrance carrier and a fragrance base; and
ii) optionally, at least one fragrance adjuvant.
10. The textile article of claim 9, wherein the perfuming composition is present in the nonwoven fabric coating.
11. The textile article according to any of the preceding claims, wherein the textile article is a drum-dried sheet, a drying sphere, a drying pouch or a wipe, preferably a drum-dried sheet.
12. The textile article of any of the preceding claims, wherein the textile article comprises at least one agent selected from the group consisting of antistatic agents, dye transfer inhibitors, brighteners, enzymes, soil repellants, anti-wrinkling agents, and fabric softeners.
13. A process for preparing a textile article as defined in any one of the preceding claims, comprising the step of adding an effective amount of a pro-fragrance compound of formula (I) to the textile article.
14. Use of a textile article as defined in any of claims 1 to 12 for improving, enhancing, giving and/or modifying the fragrance impression and/or fragrance intensity of garments during tumble drying.
15. A method for improving, enhancing, imparting and/or modifying the fragrance impression and/or fragrance intensity of a garment, comprising the step of adding a textile article as defined in any one of claims 1 to 12 to the garment during tumble drying.
CN202280046011.6A 2021-06-28 2022-06-28 Textile product for drum drying Pending CN117580993A (en)

Applications Claiming Priority (4)

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US202163215556P 2021-06-28 2021-06-28
US63/215,556 2021-06-28
EP21185796.6 2021-07-15
PCT/EP2022/067747 WO2023275056A1 (en) 2021-06-28 2022-06-28 Textile articles for tumble-drying

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