US20020178515A1 - Cyclodextrin-containing pigment printing dyestuff with scent effects, preparation thereof and use thereof - Google Patents

Cyclodextrin-containing pigment printing dyestuff with scent effects, preparation thereof and use thereof Download PDF

Info

Publication number
US20020178515A1
US20020178515A1 US10/157,942 US15794202A US2002178515A1 US 20020178515 A1 US20020178515 A1 US 20020178515A1 US 15794202 A US15794202 A US 15794202A US 2002178515 A1 US2002178515 A1 US 2002178515A1
Authority
US
United States
Prior art keywords
cyclodextrin
oil
scent
dyestuff composition
printing
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US10/157,942
Inventor
Jens-Peter Moldenhauer
Gloria Kaluza
Peter Habereder
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wacker Chemie AG
Original Assignee
Wacker Chemie AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Wacker Chemie AG filed Critical Wacker Chemie AG
Assigned to WACKER-CHEMIE GMBH reassignment WACKER-CHEMIE GMBH ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HABEREDER, PETER, KALUZA, GLORIA, MOLDENHAUER, JENS-PETER
Publication of US20020178515A1 publication Critical patent/US20020178515A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/005—Compositions containing perfumes; Compositions containing deodorants
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/46—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing natural macromolecular substances or derivatives thereof
    • D06P1/48—Derivatives of carbohydrates

Definitions

  • a pigment printing dyestuff for textile finishing comprises a cyclodextrin (CD) or cyclodextrin derivative in turn capable of including a scent as a guest molecule.
  • CD cyclodextrin
  • cyclodextrin derivative in turn capable of including a scent as a guest molecule.
  • Cyclodextrins are cyclic oligosaccharides constructed of 6, 7 or 8 ⁇ (1-4)-linked anhydroglucose units.
  • the ⁇ -, ⁇ - or ⁇ -cyclodextrins, which are prepared by enzymatic conversion of starch, differ in the diameter of their hydrophobic cavity and are generally suitable for the inclusion of numerous lipophilic substances.
  • Cyclodextrin derivatives are prepared by chemical modification of the —OH groups of cyclodextrin. Examples of customary modifying chemistries are hydroxypropylation using propylene oxide and methylation using methyl halides.
  • the cyclodextrin derivatives thus obtained are substantially more soluble in water than native cyclodextrins and are capable of solubilizing inherently water-insoluble, hydrophobic substances in an aqueous medium by inclusion and formation of water-soluble complexes.
  • Printing is local color dyeing in zones corresponding to a pattern. Conformation to these zones dictated by the engraved pattern is ensured by the thickening of the color.
  • the type and size of the artistic design determine the printing process and the dyestuff paste application method. Each printing technique is carried out using a specific printing process, which is usually based on a uniform sequence of operations (printing, drying, steaming, washing).
  • the pigment printing process is known in textile finishing as an inexpensive technology which is easy to carry out.
  • patterns are applied to fabrics using suitable screen printing stencils, for example.
  • Screen printing stencils are partially pervious, so that a printing dyestuff, generally a printing paste, can be applied by means of suitable squeegees on a printing machine.
  • Pigment printing utilizes color dye pigments which are devoid of any chemical bonding to the substrate to be printed.
  • a binder is employed to combine with the pigments to form a kind of colored film.
  • binders are for example thermally crosslinkable acrylates, polyurethanes and butadiene-styrene copolymers. Other binders are known as well.
  • the system is thickened with thickeners to values which are preferably between 5 000 and 20 000 cSt. It is customary to reduce abrasion by adding a silicone emulsion which additionally is capable of positively influencing the hand as well.
  • the print After application to the textile, the print is dried and fixed. This is preferably accomplished by treating the print at around 150-190° C. for several minutes, in the course of which the water in the printing paste evaporates and the binder is rendered insoluble by crosslinking. As a result, the color dye pigment is bound to the substrate.
  • the print is not washed and so the pigment printing process creates virtually no wastewater. This process is therefore very popular for economic and ecological reasons; more than 50% of the world's printed yardage is produced in this way.
  • a printed fabric possesses visual appeal by virtue of color and design. But customers are increasingly desirous of additional, olfactory stimuli; that is, the fabric shall also have an appealing odor.
  • Odorants are volatile, by their very nature. Perfumed fabric would thus very rapidly lose its odor. To remedy this disadvantage, it is known to include odorants in microcapsules and to incorporate these doped microcapsules in printing pastes. The microcapsules are then fixed by the binder as well. If, then, a fabric which has been printed in this way is rubbed, the microcapsules will burst and immediately release the scent. Due to the high costs of such perfumed microcapsules, this method is costly and limited to a single emission of odorant. It has therefore only found very restricted use.
  • a pigment printing dyestuff composition which includes a cyclodextrin or cyclodextrin derivative in turn capable of including a scent as a guest molecule.
  • the printing dyestuff composition according to the invention preferably comprises a cyclodextrin or cyclodextrin derivative complexed with a scent.
  • the printing dyestuff composition according to the invention preferably includes from 1 to 15% by weight of cyclodextrin or cyclodextrin derivative, based upon the total weight of the composition.
  • the printing dyestuff composition preferably includes from 0.1 to 1.5% by weight of a scent, based upon the total weight of the composition.
  • the present invention provides a printing paste dyestuff composition, comprising
  • the present invention provides a printing paste dyestuff composition
  • a printing paste dyestuff composition comprising
  • the present invention provides a printing paste dyestuff composition
  • a printing paste dyestuff composition comprising
  • a cyclodextrin derivative in an amount ranging from 1% to 15% by weight, based upon the total weight of the dyestuff composition; a scent in an amount ranging from 0.1% to 1.5% by weight, based upon the total weight of the dyestuff composition;
  • water in an amount ranging from 40% to 60% by weight, based upon the total weight of the dyestuff composition; and from 23.5% to 58.9% by weight of a dye and an ingredient selected from the group consisting of a silicone dispersion, a polyurethane binder, a silicone oil, a thickener, and mixtures thereof.
  • scent as used herein also comprehends essences and aromas
  • the scent is preferably selected from the group consisting of fruity notes based on citral (lemon scent), allyl caproate, rose oil, substances having rose scent, citral, substances having lemon scent, apple aroma, vanillin, cinnamaldehyde (pineapple), prenyl acetate (banana), heliotropin (cherry), agruma oils; herbal notes based on lavender oil, rosemary oil, thyme oil, sage oil, peppermint oil, eucalyptus oil, tea tree oil, camomile oil, spicy notes based on cinnamaldehydes (cinnamon), eugenol (clove flower); woody notes based on sandalwood oil, cedar oil, cyprus oil and rosewood oil; flowery scents based on ionone (violet), terpineol (lilac), phenylethyl
  • Useful printing dyestuffs include all known, customary pigment printing dyes.
  • the pigment printing dyestuff is preferably a paste. More preferably, it is an aqueous pigment printing dyestuff or paste, of which aqueous pigment printing pastes are particularly preferred.
  • Cyclodextrins and cyclodextrin derivatives are soluble in water and therefore are readily incorporated into aqueous printing dyestuffs. Dissolved in water, they have the useful property of encapsulating water-insoluble odorants, so that these can be taken up in the aqueous system simply by stirring into an aqueous cyclodextrin solution.
  • the pigment printing dyestuff composition according to the invention is easily preparable by incorporating a cyclodextrin, a cyclodextrin derivative, a cyclodextrin or cyclodextrin derivative and subsequently a scent, a cyclodextrin-scent complex or a cyclodextrin derivative-scent complex in the printing dyestuff by stirring or kneading.
  • the incorporating is preferably effected at 20 to 60° C. under atmospheric pressure.
  • the incorporating time is preferably between 1 and 30 minutes.
  • the cyclodextrin-scent complex can be produced not only during the making of the printing dyestuff composition by addition of a scent to an aqueous cyclodextrin-containing printing dyestuff but also separately using an aqueous cyclodextrin solution and then be incorporated in a customary printing dyestuff.
  • a cyclodextrin-scent complex is preparable in a conventional manner, for example from solution or by the paste method.
  • An advantageous way is to prepare it from an aqueous solution or suspension of cyclodextrin or cyclodextrin derivative.
  • the CD concentration of the aqueous solution or suspension is between 1-60% by weight based upon the total weight of the aqueous solution or suspension. Preference is given to a CD concentration of 10-20% based upon the total weight of the aqueous solution or suspension.
  • the weight ratio of scent to CD is between 1:100 and 1:1, preferably between 1:20 and 1:5. The batches are intensively stirred or kneaded, depending on the consistency.
  • the reaction temperature is customarily at 20-80° C. Preference is given to a reaction temperature of 20-60° C. and more preference to a reaction temperature of 20-40° C.
  • the complexing time depends on the reaction temperature and is between a few minutes and several hours. Preference is given to a reaction time of 1 to 30 minutes.
  • the complexing is generally effected under atmospheric pressure.
  • the complexing preferably takes place in a contained system in order that loss of scent during the complexing may be prevented.
  • the printing dyestuff according to the intention is applied to the textile in a customary manner known for the corresponding non-cyclodextrin-containing printing dyestuff.
  • the odorants present in the printing dyestuff are then applied to the textile in the form of their cyclodextrin complexes in the course of the printing and drying operation and are fixed by the binder present in the printing ink.
  • the invention thus also provides for the use of a printing ink according to the invention for printing textiles.
  • the printing inks according to the invention make it possible to produce attractive, fragrant, printed textiles in a simple and inexpensive manner.
  • the invention thus also provides textiles printed with a pigment printing ink according to the invention.
  • Odorants may be chosen to harmonize with the dye and the design. For instance, rose oil can be combined with a red pigment to print a floral motif, or lemon oil can be combined with a yellow pigment and apple aroma with a green pigment to print fruit motifs. The unity of visual and olfactory sensations creates an hitherto unattainable whole.
  • the odor components are released under the influence or heat and moisture, i.e., conditions which are the natural result of the wearing of garments. Robust mechanical action as in the case of microcapsules is not needed.
  • the bound cyclodextrins are rechargeable with the scent, whereas microcapsules have to be irreversibly destroyed.
  • a textile printed with a pigment printing dyestuff Composition according to the invention can be provided with new scent simply by spraying with an aqueous scent solution or suspension, The scent is initially taken up by the cyclodextrin. As the printed garment is worn, the scent is then gradually released under the action of heat and moisture.
  • the invention thus further provides a process of spraying a textile according to the invention with an aqueous scent solution.
  • a printing paste was prepared at room temperature by the following method:
  • Emuldur DS 2360 BASF polyurethane binder
  • the printing paste was subsequently homogenized by stirring with a bladed stirrer at 800 rpm for 10 minutes.
  • This printing paste according to the invention was applied through a screen printing stencil bearing a rose motif onto bleached 100% cotton knit and dried.
  • the pink flowers exude an intense rose scent on contact with the naked forearm, for example, after adjustment to body heat and body moisture.
  • Example 1 was repeated with the following differences: the cyclodextrin used was hydroxypropyl- ⁇ -cyclodextrin (CAVASOL® W7 HP), the perfume oil was Citral 54450 from Drom and the dye used was Helizarin Yellow GTN (BASF), at 10 g per liter. This reduces the amount of water needed from 192 g to 183 g.
  • CAVASOL® W7 HP hydroxypropyl- ⁇ -cyclodextrin
  • BASF Helizarin Yellow GTN
  • This paste according to the invention was printed onto a customary 65/35 polyester/cotton fabric in a lemon motif.
  • the fruit design exuded a fresh fruity odor under conditions as mentioned in Example 1.

Abstract

A pigment printing dyestuff composition for textile finishing comprises a cyclodextrin or cyclodextrin derivative in turn capable of including a scent as a guest molecule.

Description

    BACKGROUND OF THE INVENTION
  • 1. Field of the Invention [0001]
  • A pigment printing dyestuff for textile finishing comprises a cyclodextrin (CD) or cyclodextrin derivative in turn capable of including a scent as a guest molecule. [0002]
  • 2. The Prior Art [0003]
  • Cyclodextrins (CD) are cyclic oligosaccharides constructed of 6, 7 or 8 α(1-4)-linked anhydroglucose units. The α-, β- or γ-cyclodextrins, which are prepared by enzymatic conversion of starch, differ in the diameter of their hydrophobic cavity and are generally suitable for the inclusion of numerous lipophilic substances. [0004]
  • Cyclodextrin derivatives are prepared by chemical modification of the —OH groups of cyclodextrin. Examples of customary modifying chemistries are hydroxypropylation using propylene oxide and methylation using methyl halides. The cyclodextrin derivatives thus obtained are substantially more soluble in water than native cyclodextrins and are capable of solubilizing inherently water-insoluble, hydrophobic substances in an aqueous medium by inclusion and formation of water-soluble complexes. [0005]
  • Printing is local color dyeing in zones corresponding to a pattern. Conformation to these zones dictated by the engraved pattern is ensured by the thickening of the color. The type and size of the artistic design determine the printing process and the dyestuff paste application method. Each printing technique is carried out using a specific printing process, which is usually based on a uniform sequence of operations (printing, drying, steaming, washing). [0006]
  • The pigment printing process is known in textile finishing as an inexpensive technology which is easy to carry out. In it, patterns are applied to fabrics using suitable screen printing stencils, for example. Screen printing stencils are partially pervious, so that a printing dyestuff, generally a printing paste, can be applied by means of suitable squeegees on a printing machine. Pigment printing utilizes color dye pigments which are devoid of any chemical bonding to the substrate to be printed. In order that they may nonetheless be fixed on the substrate, a binder is employed to combine with the pigments to form a kind of colored film. Such binders are for example thermally crosslinkable acrylates, polyurethanes and butadiene-styrene copolymers. Other binders are known as well. To ensure crisp contours in opposition to the capillary forces of the substrate, the system is thickened with thickeners to values which are preferably between 5 000 and 20 000 cSt. It is customary to reduce abrasion by adding a silicone emulsion which additionally is capable of positively influencing the hand as well. [0007]
  • After application to the textile, the print is dried and fixed. This is preferably accomplished by treating the print at around 150-190° C. for several minutes, in the course of which the water in the printing paste evaporates and the binder is rendered insoluble by crosslinking. As a result, the color dye pigment is bound to the substrate. The print is not washed and so the pigment printing process creates virtually no wastewater. This process is therefore very popular for economic and ecological reasons; more than 50% of the world's printed yardage is produced in this way. [0008]
  • A printed fabric possesses visual appeal by virtue of color and design. But customers are increasingly desirous of additional, olfactory stimuli; that is, the fabric shall also have an appealing odor. [0009]
  • Odorants, however, are volatile, by their very nature. Perfumed fabric would thus very rapidly lose its odor. To remedy this disadvantage, it is known to include odorants in microcapsules and to incorporate these doped microcapsules in printing pastes. The microcapsules are then fixed by the binder as well. If, then, a fabric which has been printed in this way is rubbed, the microcapsules will burst and immediately release the scent. Due to the high costs of such perfumed microcapsules, this method is costly and limited to a single emission of odorant. It has therefore only found very restricted use. [0010]
    • SUMMARY OF THE INVENTION
  • It is an object of the present invention to provide a pigment printing dyestuff for textile finishing that, after application to the textile, can be activated in the course of the wearing of the textile; possesses a long-lasting scent effect; and can be reactivated by reloading with odorant. [0011]
  • This object is achieved by a pigment printing dyestuff composition which includes a cyclodextrin or cyclodextrin derivative in turn capable of including a scent as a guest molecule. [0012]
  • The printing dyestuff composition according to the invention preferably comprises a cyclodextrin or cyclodextrin derivative complexed with a scent. [0013]
  • It is possible to use α-, β- or γ-cyclodextrin or derivatives thereof or mixtures thereof. Hydroxypropyl and methyl derivatives of α-, βor γ-cyclodextrin will be found to be particularly advantageous, [0014]
  • The printing dyestuff composition according to the invention preferably includes from 1 to 15% by weight of cyclodextrin or cyclodextrin derivative, based upon the total weight of the composition. [0015]
  • The printing dyestuff composition preferably includes from 0.1 to 1.5% by weight of a scent, based upon the total weight of the composition. [0016]
  • More particularly, the present invention provides a printing paste dyestuff composition, comprising [0017]
  • 70 g of methyl-β-cyclodextrin; dissolved in 400 g of deionized water; 7 g of perfume oil (a scent); 100 g of silicone dispersion; 100 g of polyurethane binder, 50 g of silicone oil emulsion; 1 g of dye; 192 g of deionized water; and 80 g of thickener. [0018]
  • Also, the present invention provides a printing paste dyestuff composition comprising [0019]
  • 70 g of hydroxypropyl-β-cyclodextrin; dissolved in 400 g of deionized water; 7 g of perfume oil (a scent); 100 g of silicone dispersion; 100 g of polyurethane binder; 50 g of silicone oil emulsion; 10 g/liter of dye; 183 g of deionized water; and 80 g of thickener. [0020]
  • In addition, the present invention provides a printing paste dyestuff composition comprising [0021]
  • a cyclodextrin derivative in an amount ranging from 1% to 15% by weight, based upon the total weight of the dyestuff composition; a scent in an amount ranging from 0.1% to 1.5% by weight, based upon the total weight of the dyestuff composition; [0022]
  • water in an amount ranging from 40% to 60% by weight, based upon the total weight of the dyestuff composition; and from 23.5% to 58.9% by weight of a dye and an ingredient selected from the group consisting of a silicone dispersion, a polyurethane binder, a silicone oil, a thickener, and mixtures thereof. [0023]
  • The term “scent” as used herein also comprehends essences and aromas, The scent is preferably selected from the group consisting of fruity notes based on citral (lemon scent), allyl caproate, rose oil, substances having rose scent, citral, substances having lemon scent, apple aroma, vanillin, cinnamaldehyde (pineapple), prenyl acetate (banana), heliotropin (cherry), agruma oils; herbal notes based on lavender oil, rosemary oil, thyme oil, sage oil, peppermint oil, eucalyptus oil, tea tree oil, camomile oil, spicy notes based on cinnamaldehydes (cinnamon), eugenol (clove flower); woody notes based on sandalwood oil, cedar oil, cyprus oil and rosewood oil; flowery scents based on ionone (violet), terpineol (lilac), phenylethyl alcohol/citronellol (rose), hydroxycitronellol (lily of the valley); alpha-hexylcinnamaldehyde/benzyl alcohol (jasmine), ylang-ylang oil (ylang-ylang); animalistic notes based on polycyclic and also macrocyclic compounds (musk); sweet, balsamic notes based on vanillin (vanilla), anethole (aniseed), benzaldehyde (almond), courmarin (moss, hay). [0024]
  • Useful printing dyestuffs include all known, customary pigment printing dyes. The pigment printing dyestuff is preferably a paste. More preferably, it is an aqueous pigment printing dyestuff or paste, of which aqueous pigment printing pastes are particularly preferred. [0025]
  • Cyclodextrins and cyclodextrin derivatives are soluble in water and therefore are readily incorporated into aqueous printing dyestuffs. Dissolved in water, they have the useful property of encapsulating water-insoluble odorants, so that these can be taken up in the aqueous system simply by stirring into an aqueous cyclodextrin solution. [0026]
  • The pigment printing dyestuff composition according to the invention is easily preparable by incorporating a cyclodextrin, a cyclodextrin derivative, a cyclodextrin or cyclodextrin derivative and subsequently a scent, a cyclodextrin-scent complex or a cyclodextrin derivative-scent complex in the printing dyestuff by stirring or kneading. [0027]
  • The incorporating is preferably effected at 20 to 60° C. under atmospheric pressure. The incorporating time is preferably between 1 and 30 minutes. [0028]
  • The cyclodextrin-scent complex can be produced not only during the making of the printing dyestuff composition by addition of a scent to an aqueous cyclodextrin-containing printing dyestuff but also separately using an aqueous cyclodextrin solution and then be incorporated in a customary printing dyestuff. [0029]
  • A cyclodextrin-scent complex is preparable in a conventional manner, for example from solution or by the paste method. An advantageous way is to prepare it from an aqueous solution or suspension of cyclodextrin or cyclodextrin derivative. [0030]
  • The CD concentration of the aqueous solution or suspension is between 1-60% by weight based upon the total weight of the aqueous solution or suspension. Preference is given to a CD concentration of 10-20% based upon the total weight of the aqueous solution or suspension. The weight ratio of scent to CD is between 1:100 and 1:1, preferably between 1:20 and 1:5. The batches are intensively stirred or kneaded, depending on the consistency. [0031]
  • The reaction temperature is customarily at 20-80° C. Preference is given to a reaction temperature of 20-60° C. and more preference to a reaction temperature of 20-40° C. The complexing time depends on the reaction temperature and is between a few minutes and several hours. Preference is given to a reaction time of 1 to 30 minutes. [0032]
  • The complexing is generally effected under atmospheric pressure. The complexing preferably takes place in a contained system in order that loss of scent during the complexing may be prevented. [0033]
  • Mixing this odorant-containing cyclodextrin solution with the customary ingredients of a pigment printing dyestuff composition gives a printing dyestuff having an individual scent note. [0034]
  • The printing dyestuff according to the intention is applied to the textile in a customary manner known for the corresponding non-cyclodextrin-containing printing dyestuff. The odorants present in the printing dyestuff are then applied to the textile in the form of their cyclodextrin complexes in the course of the printing and drying operation and are fixed by the binder present in the printing ink The invention thus also provides for the use of a printing ink according to the invention for printing textiles. [0035]
  • The printing inks according to the invention make it possible to produce attractive, fragrant, printed textiles in a simple and inexpensive manner. [0036]
  • The invention thus also provides textiles printed with a pigment printing ink according to the invention. [0037]
  • Odorants may be chosen to harmonize with the dye and the design. For instance, rose oil can be combined with a red pigment to print a floral motif, or lemon oil can be combined with a yellow pigment and apple aroma with a green pigment to print fruit motifs. The unity of visual and olfactory sensations creates an hitherto unattainable whole. [0038]
  • The printing dyestuff according to the invention, after it has been applied to the textile, offers two further advantages over the prior art: [0039]
  • Firstly, the odor components are released under the influence or heat and moisture, i.e., conditions which are the natural result of the wearing of garments. Robust mechanical action as in the case of microcapsules is not needed. [0040]
  • Secondly, the bound cyclodextrins are rechargeable with the scent, whereas microcapsules have to be irreversibly destroyed. [0041]
  • A textile printed with a pigment printing dyestuff Composition according to the invention can be provided with new scent simply by spraying with an aqueous scent solution or suspension, The scent is initially taken up by the cyclodextrin. As the printed garment is worn, the scent is then gradually released under the action of heat and moisture. [0042]
  • The invention thus further provides a process of spraying a textile according to the invention with an aqueous scent solution. [0043]
    • DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENT
  • The examples hereinbelow illustrate the invention.[0044]
    • EXAMPLE 1
  • A printing paste was prepared at room temperature by the following method: [0045]
  • 70 g of methyl-β-cyclodextrin (CAVASOL® W7 M) were dissolved in 400 g of deionized water. 7 g of rose type 131650 perfume oil from Kurt Kitzing GmbH, Wallerstein were added with stirring. After just 1 minute, the water-insoluble oil formed a clear solution in the cyclodextrin solution. [0046]
  • This solution was admixed with [0047]
  • 100 g of Finish CT 27 E (Wacker silicone dispersion), [0048]
  • 100 g of Emuldur DS 2360 (BASF polyurethane binder), [0049]
  • 50 g of Finish C 800 (Wacker silicone oil emulsion) and [0050]
  • 1 g of Helizarin Brilliant Red BBT (BASF). [0051]
  • Then [0052]
  • 192 g of deionized water and [0053]
  • 80 g of Appretan thickener 3308 (Clariant) were added to prepare 1 kg of printing paste. [0054]
  • The printing paste was subsequently homogenized by stirring with a bladed stirrer at 800 rpm for 10 minutes. [0055]
  • This printing paste according to the invention was applied through a screen printing stencil bearing a rose motif onto bleached 100% cotton knit and dried. The pink flowers exude an intense rose scent on contact with the naked forearm, for example, after adjustment to body heat and body moisture. [0056]
    • EXAMPLE 2
  • Example 1 was repeated with the following differences: the cyclodextrin used was hydroxypropyl-β-cyclodextrin (CAVASOL® W7 HP), the perfume oil was Citral 54450 from Drom and the dye used was Helizarin Yellow GTN (BASF), at 10 g per liter. This reduces the amount of water needed from 192 g to 183 g. [0057]
  • This paste according to the invention was printed onto a customary 65/35 polyester/cotton fabric in a lemon motif. The fruit design exuded a fresh fruity odor under conditions as mentioned in Example 1. [0058]
  • Accordingly, while only several embodiments of the present invention have been shown and described, it is obvious that many changes and modifications may be made thereunto without departing from the spirit and scope of the invention. [0059]

Claims (15)

What is claimed is:
1. A pigment printing dyestuff composition for textile finishing, comprising
a substance selected from the group consisting of a cyclodextrin and a cyclodextrin derivative; and said substance including a scent as a guest molecule.
2. The pigment printing dyestuff composition as claimed in claim 1,
wherein said cyclodextrin or cyclodextrin derivative is complexed with said scent.
3. The pigment printing dyestuff composition as claimed in claim 1,
wherein said cyclodextrin or cyclodextrin derivative is selected from the group consisting of a hydroxypropyl derivative of α-, β- and γ-cyclodextrin and a methyl derivative of α-, β- and γ-cyclodextrin.
4. The pigment printing dyestuff composition as claimed in claim 1,
wherein said cyclodextrin or cyclodextrin derivative is present in an amount ranging from 1% to 15% by weight, based upon the total weight of the dyestuff composition.
5. The pigment printing dyestuff composition as claimed in claim 1,
wherein said scent is present in an amount ranging from 0.1% to 1.5% by weight, based upon the total weight of the dyestuff composition.
6. The pigment printing dyestuff composition as claimed in claim 1,
wherein said scent is selected from the group consisting of fruity notes based on citral (lemon scent), allyl caproate, rose oil, substances having rose scent, citral, substances having lemon scent, apple aroma, vanillin, cinnamaldehyde (pineapple), prenyl acetate (banana), heliotropin (cherry), agruma oils; herbal notes based on lavender oil, rosemary oil, thyme oil, sage oil, peppermint oil, eucalyptus oil, tea tree oil, camomile oil; spicy notes based on cinnamaldehydes (cinnamon), eugenol (clove flower); woody notes based on sandalwood oil, cedar oil, cyprus oil and rosewood oil; flowery scents based on ionone (violet), terpineol (lilac), phenylethyl alcohol/citronellol (rose), hydroxycitronellol (lily of the valley); alpha-hexylcinnamaldehyde/benzyl alcohol (jasmine), ylang-ylang oil (ylang-ylang); animalic notes based on polycyclic and also macrocyclic compounds (musk); sweet, balsamic notes based on vanillin (vanilla), anethole (aniseed), benzaldehyde (almond), courmarin (moss, hay).
7. The pigment printing dyestuff composition as claimed in claim 1, further comprising
water and being an aqueous scent solution.
8. A pigment printing dyestuff composition as claimed in claim 1, further comprising
water and being a paste.
9. A process for preparing a pigment printing dyestuff composition comprising
incorporating a substance selected from the group consisting of a cyclodextrin, a cyclodextrin derivative, a cyclodextrin or cyclodextrin derivative and subsequently a scent, a cyclodextrin-scent complex and a cyclodextrin derivative-scent complex, in a pigment printing dyestuff by stirring or kneading.
10. In a method of printing textiles, the improvement comprises utilizing a pigment printing dyestuff composition as claimed in claim 1 for printing textiles.
11. Textiles printed with a pigment printing dyestuff composition as claimed in claim 1.
12. A process for reactivating a textile, which comprises
spraying said textile with an aqueous scent solution, as claimed in claim 7.
13. A printing paste dyestuff composition, comprising
70 g of methyl-β-cyclodextrin; dissolved in
400 g of deionized water;
7 g of perfume oil;
100 g of silicone dispersion;
100 g of polyurethane binder;
50 g of silicone oil emulsion;
1 g of dye;
192 g of deionized water; and
80 g of thickener.
14. A printing paste dyestuff composition comprising
70 g of hydroxypropyl-β-cyclodextrin; dissolved in
400 g of deionized water;
7 g of perfume oil;
100 g of silicone dispersion;
100 g of polyurethane binder;
50 g of silicone oil emulsion;
10 g/liter of dye;
183 g of deionized water; and
80 g of thickener.
15. A printing paste dyestuff composition comprising
a cyclodextrin derivative in an amount ranging from 1% to 15% by weight, based upon the total weight of the dyestuff composition;
a scent in an amount ranging from 0.1% to 1.5% by weight, based upon the total weight of the dyestuff composition;
water in an amount ranging from 40% to 60% by weight, based upon the total weight of the dyestuff composition; and
from 23.5% to 58.9%, by weight of a dye and an ingredient selected from the group consisting of a silicone dispersion, a polyurethane binder, a silicone oil, a thickener, and mixtures thereof.
US10/157,942 2001-05-31 2002-05-29 Cyclodextrin-containing pigment printing dyestuff with scent effects, preparation thereof and use thereof Abandoned US20020178515A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10126561A DE10126561A1 (en) 2001-05-31 2001-05-31 Pigment-based printing ink containing cyclodextrin with fragrance effects, process for their production and their use
DE10126561.1 2001-05-31

Publications (1)

Publication Number Publication Date
US20020178515A1 true US20020178515A1 (en) 2002-12-05

Family

ID=7686792

Family Applications (1)

Application Number Title Priority Date Filing Date
US10/157,942 Abandoned US20020178515A1 (en) 2001-05-31 2002-05-29 Cyclodextrin-containing pigment printing dyestuff with scent effects, preparation thereof and use thereof

Country Status (2)

Country Link
US (1) US20020178515A1 (en)
DE (1) DE10126561A1 (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030072952A1 (en) * 2001-05-23 2003-04-17 Alan Crabtree Process for printing textile fabrics
US20030094117A1 (en) * 2001-11-14 2003-05-22 In-Shan Sir Fragrant ink with microcapsule compounds to provide fragrance
US20080283693A1 (en) * 2007-05-15 2008-11-20 Evans Michael J F Propulsion apparatus and system
US20090029020A1 (en) * 2005-06-13 2009-01-29 Cargill, Incorporated Cyclodextrin inclusion complexes and methods of preparing same
US20090185985A1 (en) * 2006-06-13 2009-07-23 Cargill, Incorporated Large-particle cyclodextrin inclusion complexes and methods of preparing same
US20090214446A1 (en) * 2005-06-13 2009-08-27 Cargill, Incorporated Cyclodextrin inclusion complexes and methods of preparing same
US20100160623A1 (en) * 2006-12-27 2010-06-24 Cargill, Incorporated Cyclodextrin inclusion complexes and methods of preparing same
CN106079945A (en) * 2016-08-01 2016-11-09 太仓市鑫泰针织有限公司 A kind of printing method of bamboo fiber knitting product
JP2017210547A (en) * 2016-05-25 2017-11-30 株式会社パイロットコーポレーション Water-based ink composition for writing instrument and writing instrument using the same
CN109337408A (en) * 2018-11-29 2019-02-15 武汉职业技术学院 A kind of extracting method and its application of roselle natural dye
CN117402533A (en) * 2023-11-17 2024-01-16 佛山优博润科技有限公司 Ammonia gas visual response coating and preparation method and application thereof

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030072952A1 (en) * 2001-05-23 2003-04-17 Alan Crabtree Process for printing textile fabrics
US6776804B2 (en) * 2001-05-23 2004-08-17 Ciba Specialty Chemicals Corporation Process for printing textile fabrics
US20030094117A1 (en) * 2001-11-14 2003-05-22 In-Shan Sir Fragrant ink with microcapsule compounds to provide fragrance
US6706099B2 (en) * 2001-11-14 2004-03-16 Benq Corporation Fragrant ink with microcapsule compounds to provide fragrance
US20090214446A1 (en) * 2005-06-13 2009-08-27 Cargill, Incorporated Cyclodextrin inclusion complexes and methods of preparing same
US20090029020A1 (en) * 2005-06-13 2009-01-29 Cargill, Incorporated Cyclodextrin inclusion complexes and methods of preparing same
US20090185985A1 (en) * 2006-06-13 2009-07-23 Cargill, Incorporated Large-particle cyclodextrin inclusion complexes and methods of preparing same
US20100160623A1 (en) * 2006-12-27 2010-06-24 Cargill, Incorporated Cyclodextrin inclusion complexes and methods of preparing same
US20080283693A1 (en) * 2007-05-15 2008-11-20 Evans Michael J F Propulsion apparatus and system
JP2017210547A (en) * 2016-05-25 2017-11-30 株式会社パイロットコーポレーション Water-based ink composition for writing instrument and writing instrument using the same
CN106079945A (en) * 2016-08-01 2016-11-09 太仓市鑫泰针织有限公司 A kind of printing method of bamboo fiber knitting product
CN109337408A (en) * 2018-11-29 2019-02-15 武汉职业技术学院 A kind of extracting method and its application of roselle natural dye
CN117402533A (en) * 2023-11-17 2024-01-16 佛山优博润科技有限公司 Ammonia gas visual response coating and preparation method and application thereof

Also Published As

Publication number Publication date
DE10126561A1 (en) 2002-12-12

Similar Documents

Publication Publication Date Title
US20020178515A1 (en) Cyclodextrin-containing pigment printing dyestuff with scent effects, preparation thereof and use thereof
Eid et al. Recent developments in sustainable finishing of cellulosic textiles employing biotechnology
Buschmann et al. The use of cyclodextrins in textile processes—an overview
Abdelrahman et al. Review in textile printing technology
JP7416620B2 (en) Method for manufacturing microcapsules
JP2003190264A (en) Aromatic deodorizing composition for environment and aromatic deodorizer for environment containing the aromatic deodorizing composition for environment
CN103233368B (en) Preparation and application of modified melamine resin essence microcapsule finishing agent
CN105544230B (en) A method of using tea tree ethereal oil microcapsules flavoring on the textile
CN1993412A (en) Compositions for sustained release of volatile materials
CN105132169A (en) Green apple essence used for water-based ink and preparation method of green apple essence
CN105132170A (en) Lemon essence for water-based ink and preparation method of lemon essence
CN105087162A (en) Osmanthus flower essence for water-based ink and preparing method of osmanthus flower essence
Yıldırım et al. Printing with sustainable natural dyes and pigments
El-Sayed et al. Cyclodextrin usage in textile industry
Wang et al. Surface treatment of cotton using β-cyclodextrins sol–gel method
JP3813165B2 (en) Method for producing artificial flower using natural plant and finishing agent used therefor
Maulik et al. Sustainable dyeing and printing of knitted fabric with natural dyes
CN103619414B (en) Use at least one dihydroxy flavanols, manganese salt or zinc salt, hydrogen peroxide, carbonic acid（Hydrogen）The hair-dyeing method of salt, basifier and magnesium salts, molybdenum salt or calcium salt
CN107485047A (en) A kind of preparation method of essence spice for cigarette temperature control sustained-release micro-capsule
JP2021134468A (en) Long term holding sheet for flavor component
JP5671715B2 (en) Perfume emulsified dispersion
KR20020056779A (en) Fragrant textile produced by using fragrant coating composition and a process of producing same
DE102008000084A1 (en) Aqueous emulsion containing a cyclodextrin derivative, a fragrance and a polysorbate
JPH0252661A (en) Marking material having deodorant or deodorant exhalation function
RU2208431C1 (en) Hair dye

Legal Events

Date Code Title Description
AS Assignment

Owner name: WACKER-CHEMIE GMBH, GERMANY

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:MOLDENHAUER, JENS-PETER;KALUZA, GLORIA;HABEREDER, PETER;REEL/FRAME:012955/0030

Effective date: 20020516

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION