JP2002212879A - Method for reducing wrinkle in fabric and improving feeling - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a method useful for the absorption and retention of water in a natural and synthetic fabric by which the wrinkles of clothes are reduced and the feeling of the fabric is improved. SOLUTION: A material is treated for reducing the wrinkles, imparting temporary crease resistance, and improving the feeling. The method comprises applying the solution of the treating composition in an amount effective for imparting the temporal crease resistance and antifouling properties to the material (the treating composition contains hydroxyurea or hydroxyamide), and drying the treating composition at a surrounding temperature (the hydroxyurea compound contains one urea and at least one hydroxy group, and the hydroxyamide compound contains at least one amide group and at least one hydroxy group).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a method for reducing wrinkles,
In the treatment of materials to provide temporary wrinkle resistance, improve the feel (tactile sensation) of the fabric, and increase water absorption,
It relates to using a treatment composition comprising a hydroxyurea or hydroxyamide compound. More specifically, the method of the present invention involves applying the hydroxy compound to the material in solution, neat or as a mist, and drying the material at ambient temperature without applying an external heat source. The treatment composition can also be included in a laundry detergent or fabric softener.

[0002]

BACKGROUND OF THE INVENTION Wrinkle-free clothing, fabrics and other materials are:
It is seen in a more favorable view than the same material with wrinkles. Therefore, reducing the wrinkles of fabrics and other materials,
Many methods have been developed to develop anti-wrinkle materials. It is well known in the art to use thermosetting resins or reactants to provide wrinkle resistance and dimensional stability to textile materials. These materials, known as "aminoplast resins", include the reaction products of formaldehyde with compounds such as urea, thiourea, ethylene urea, dihydroxyethylene urea, melamine, and the like. A significant disadvantage of using these materials is that they contain free formaldehyde. It is present on treated fabrics and finished garments during the preparation and storage of finishing agents and their use during the processing of textiles. Also, when the fabric or garment made therefrom is stored under wet conditions, more free formaldehyde is produced.

[0003] Even the presence of less than 1% free formaldehyde, based on the total weight of the product, not only because of the unpleasant odor, it also treats and treats the technician making the agent and the treated fabric. This is undesirable because it is an allergen and irritant that causes severe reactions to technicians as well as those who handle and wear garments made from the treated fabric.

[0004] Solutions containing lubricants, such as silicone compounds, are known to reduce the friction between fibers which causes the fibers to slip too much together, thereby reducing wrinkling. Such compounds are known in the art, for example, in US Pat. No. 5,968,404 and WO 11/2.
No. 4857.

US Pat. No. 5,879,749 discloses a polyfunctional molecule having at least two functional groups selected from carboxyls, anhydrides and amines, which is crosslinked using a (hydroxyalkyl) urea crosslinker. Are described. U.S. Pat. No. 5,965,466 describes the use of hydroxyalkyl ureas and / or .beta.-hydroxyalkyl amides to impart permanent press properties to textiles containing cellulose fibers. U.S. Pat. No. 4,076,917 describes beta-hydroxyalkylamides as curing agents for polymers containing one or more carboxy or anhydride functional groups. These references require a heating step after applying the composition to the fabric to cause a crosslinking reaction.

Treating the textile with a resin composition that does not contain or release formaldehyde,
U.S. Pat. No. 3,260,565 is known, which describes finishing agents formed by the reaction of alkyl or aryl ureas or thioureas with glyoxal. U.S. Pat. Nos. 4,332,586 and 4,300,898 describe alkylated glyoxal / cyclic urea condensates as textile crosslinkers. U.S. Pat. No. 4,295,846 describes a finishing agent for textiles prepared by the reaction of glyoxal with an aqueous solution of urea or, in contrast, disubstituted urea. However, these agents have the disadvantage of having the lowest permanent press properties. JP-A-53-44567 describes finishing agents formed by the reaction of ethylene urea and glyoxal, but they also do not have satisfactory properties.

[0007] Pending US patent application Ser. No. 09 / 456,3.
No. 58 describes a textile anti-wrinkle composition containing a polyhydroxyalkyl urea anti-wrinkle agent having at least two urea moieties.

[0008]

There is a need for a material treatment composition that can be applied to a material to reduce wrinkles and provide temporary permanent press properties without the need to add an external heat source after application. . Ideally, the treatment composition should be one that does not emit formaldehyde. Surprisingly, it has been found that hydroxyurea or hydroxyamide compounds reduce wrinkles when applied to fabrics by means such as spraying, without the need for the addition of an external heat source. This method allows consumers to easily and cost effectively impart wrinkle resistance to clothing at home and even reduce wrinkles in the garment they are wearing. Further, there is a need for a wrinkle-preventing treatment that does not discolor the fabric. In addition, the treatment should not have the strong effect of counteracting soil removal, unlike silicone, which is difficult to clean because it attracts oily soils. Finally, there is a need for materials that do not leave an oily type finish in the fabric. The method of the present invention satisfies these needs.

[0009]

SUMMARY OF THE INVENTION The present invention is directed to a method of treating a material, comprising applying an effective amount of a treating agent to the material to provide temporary wrinkle resistance. The treatment composition comprises:
Includes hydroxy compounds that are either hydroxyureas or hydroxyamides. The material treatment composition can be applied to garments, fabrics and textiles to reduce wrinkles and provide temporary wrinkle resistance to the material without the need for external heat sources. It is further noted that the composition does not deposit on clothing or ironing and that there is no residual flakes, even on dark fabrics. The treatment composition can also be incorporated into a laundry detergent or fabric softener, and can thus be applied to the material during a wash or rinse cycle. The treated material has both a tactile sensation of softness and moisture absorption. In addition, the fabric has no discoloration and, unlike the silicones typically used, the material does not retain oily stains.

[0010] The present invention is directed to a method of providing a material with reduced wrinkling, permanent press properties and improved feel, and increased moisture absorption. As used herein, “wrinkle resistance” is synonymous with wrinkle resistance, no ironing property, dimensional stability, shrink resistance, and wrinkle recovery. The method includes applying a treatment composition of a hydroxy compound to the material and drying the material at ambient temperature without the application of an external heat source to impart wrinkle resistance to the material. The treatment composition is essentially free of formaldehyde and can be applied in solution or neat.

[0011] The material treated in the method of the present invention comprises a natural or synthetic material. The material may be a leather-like material or a fibrous material. The fiber material can be natural, synthetic or a mixture thereof. Such materials include, but are not limited to, fabrics, textiles, woven fabrics, and finished products made from these materials. Preferably the material is a cellulosic fabric or textile, which may be a woven or woven fabric, and 100% cellulosic fabrics such as cotton, rayon and linen, and blends such as polyester / cotton or polyester / Including rayon. The fibrous material may be non-cellulosic natural or synthetic fibers such as nylon, silk and polyester. White and colored (printed, dyed, yarn dyed, cross dyed etc.)
The material can be effectively treated with the material treatment composition of the present invention.
The material may include new garments or worn garments, including previously worn and / or washed garments.

The hydroxy compound is either hydroxyurea or hydroxyamide. Hydroxyureas useful in the present invention have one urea function and at least one
Containing one hydroxy functional group. As used herein, the term urea refers to one N-CO-N moiety, wherein the other two bonds of each nitrogen atom form an additional bond; It is found in the description of the book and in the examples. The urea and hydroxyl functions may be separated from one another by one carbon atom in the compound. Preferably they are separated by at least two carbon atoms. Hydroxyamides useful in the present invention are those containing at least one amino function and at least one hydroxyl function. Preferably, the hydroxy compound should not be a formaldehyde emitter. Preferred compounds of the present invention are either hydroxyalkyl ureas or β-hydroxyalkyl amides or mixtures thereof.

Preferred hydroxyureas are derived from urea and contain only one urea group, at least one hydroxyl group, and at least two carbon atoms located between the urea group and each hydroxyl group. The two carbons located between the hydroxyl and urea groups may be in a linear, branched or substituted form. Hydroxyurea is represented by structure (1) as follows.

[0014]

Embedded image(Where R¹ Is CR^Five R⁶ R⁷ And R^Two Is H or
R^Five And R^Three Is H or R^Five And R^Four Is H, R
¹ Or R^Five Where R^Five Is H, CH_Two OH, C
HR⁸ CHR⁹ OH, CHR⁸ CHR⁹ CHR^TenOh
Or C₁ ~ C_Four Alkyl, R⁶ Is H, CH_Two O
H, CHR⁸ CHR⁹ OH, CHR⁸ CHR ⁹ CHR^Ten
OH or C₁ ~ C_Four Alkyl, R⁷ Is H, CH
_Two OH, CHR⁸ CHR⁹ OH, CHR⁸ CHR⁹ CH
R^TenOH or C₁ ~ C_Four Alkyl, wherein R⁸ 
Is H, methyl or ethyl;⁹ Is H or methyl
Or ethyl and R^TenIs H, methyl or ethyl
)

A preferred hydroxyurea compound is N-2-
Hydroxyethyl urea, N, N-bis (2-hydroxyethyl) urea, tetrakis (2-hydroxyethyl) urea, tris (2-hydroxyethyl) urea, N, N'-
Bis (2-hydroxyethyl) urea, N, N'-bis (3-hydroxypropyl) urea, N, N'-bis (4
-Hydroxybutyl) urea, N-methyl-D-glucourea and 2-urea-2-ethyl-1,3-propanediol. Most preferably, the hydroxyurea compound is
N, N'-bis (2-hydroxyethyl) urea.
Combinations of hydroxyurea compounds can also be used in the method of the present invention.

[0016] Hydroxyurea is the reaction product of urea and alkanolamine with the evolution of ammonia. Preferred alkanolamines include, but are not limited to, diethanolamine, monoethanolamine, 2-ethanolamine.
Amino-2-methyl-1,3-propanediol, bis (hydroxymethyl) aminomethane, 2-methyl-3-
Includes amino-1-propanol and 2-methylaminoethanol. Methods for preparing hydroxyurea compounds are described in US patent application Ser. No. 08 / 783,350,
It is incorporated herein by reference.

Preferred hydroxyamide compounds are β-hydroxyalkylamide compounds represented by the following structure (II):

Embedded image

In structure (II), A is a bond, hydrogen or alkyl radical containing from 1 to 60 carbon atoms;
Saturated or unsaturated alkyl radicals, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, eicosyl, triacontyl, tetracontyl, pentacontyl, hexylcontyl and the like, aryl, for example, mononuclear Or a dinuclear aryl, for example, phenyl, naphthyl, etc., a tri-lower alkyleneamino, for example, trimethyleneamino, triethyleneamino or the like, or an unsaturated radical containing one or more ethylenic groups, for example, ethenyl, 1-methylethenyl, 3 -Butenyl-1,3-diyl, 2-propeter-1,2-diyl, carboxy lower alkenyl, for example, 3-carboxy-2-propenyl and the like, lower alkoxycarbonyl lower alkenyl, for example, 3-ethoxycarbonyl Is a monovalent or polyvalent organic radical derived from 2-propenyl, R ¹¹ is hydrogen, 1-5 lower alkyl carbon atoms, such as methyl, ethyl, n- propyl, n- butyl, sec- Butyl, t-butyl, pentyl or the like or a hydroxy lower alkyl of 1 to 5 carbon atoms, such as hydroxyethyl, 3-hydroxypropyl, 2-hydroxypropyl, 4-hydroxybutyl, 3-hydroxybutyl,
-Hydroxy-2-methylpropyl, 5-hydroxypentyl, 4-hydroxypentyl, 3-hydroxypentyl, 2-hydroxypentyl and isomers of pentyl, wherein R ¹² and R ¹³ are hydrogen, 1 to 5 carbon atoms. The same or different radicals selected from straight-chain or branched lower alkyl, or one of the R ¹² radicals and one of the R ¹³ radicals bonded together with a carbon atom, for example cyclopentyl, cyclohexyl, etc. Where n is an integer having a value of 1 or 2, and n ′ is an integer having a value of 0 to 2 or when n ′ is 0.

Preferred β-hydroxyalkyl compounds are represented by the following structure (III):

Embedded image

In the structure (III), R ¹¹ is H, lower alkyl or HO (R ¹³ ) ₂ C (R ¹² ) ₂ C—;
And n 'in each 1, -A- is - (CH _{2) m} - and is, m is 0-8, preferably 2-8, each R ¹² is H, R ¹³ in each case Is H and the other is H
Or alkyl of C ₁ -C _5. That is, R ¹¹ ,
R ¹³ and m have the meanings indicated exactly. The most preferred β-hydroxyalkylamide compound is represented by the following structure (IV).

[0021]

Embedded image R ¹³ is H or -CH ₃ in structure (IV). β
Particular examples of -hydroxyalkylamide compounds are bis [N, N-di (β-hydroxyethyl)] adipamide,
Bis [N, N-di (β-hydroxypropyl)] succinamide, bis [N, N-di (β-hydroxyethyl)] azeramide, bis [N, N-di (β-hydroxypropyl)] adipamide and bis [ N-methyl-N-
(Β-hydroxyethyl)] oxamide.

The β-hydroxyalkylamide compound is
A known compound or from ambient temperature to about 200 ° C
Can be prepared by treating the ester with an amine at a temperature in the range of Suitable esters are prepared by esterifying the corresponding acid according to standard esterification procedures. Among the acids used to make the β-hydroxyalkylamide crosslinkers, oxalic, malonic, succinic, glutaric, adipic, pimelic, suberic, azelaic, sebacic, 1,4-
Cyclohexanoic acid and the like and alkyl derivatives thereof are preferred. Dimer and trimer acids are also used. Suitable amines used to prepare the β-hydroxyalkylamide compounds are 2-aminoethanol, 2-methylaminoethanol, 2-ethylaminoethanol, 2-n-propylaminoethanol, 2,2′-iminodiethanol , 2-aminopropanol, 2,2'-iminodiisopropanol, 2-aminocyclohexanol, 2-aminocyclopentanol, 2-aminomethyl-2-methylethanol, 2-n-butylaminoethanol,
Methylamino-1,2-dimethylethanol, 2-amino-2-methyl-1-propanol, 2-amino-2-
Methyl-1,3-propanediol, 2-amino-2-
Ethyl-1,3-propanediol and 2-amino-2
-Hydroxymethyl-1,3-propanediol. β-Hydroxyalkylamide compounds are prepared by the method described in US Pat. No. 4,076,917, the description of which is incorporated herein by reference.

[0023] The treatment composition of the present invention can be used either as is or as a solution. It can also be formulated in liquid or powdered laundry detergents or fabric softeners. A solution is a solution of any solvent that forms a solution or suspension with the hydroxy compound. Examples of useful solvents include, but are not limited to, water, acetone and alcohols such as methanol, ethanol,
Propanol and butanol and mixtures of such solvents. The preferred solvent is water. The pH of the aqueous solution containing the hydroxy compound is from about 1 to about 12, more preferably from about 2 to about 10, and most preferably from 4 to 7. Most preferably, the pH of the aqueous solution containing the hydroxy compound
Is about 3 to about 8. In the method of the present invention, the desired pH
It is understood that any means of adjusting the pH of the aqueous solution may be used to achieve The treatment composition comprises, in addition to the hydroxy compound, a surfactant, a buffer, a dye, an electrolyte, a builder, a modified or unmodified cellulosic compound, a modified or unmodified starch, a cationic, nonionic or zwitterionic. It may contain one or more compounds selected from the group comprising certain polymers, enzymes, cyclodextrins, silicones and fragrances.

Any method of applying the treatment composition to the material is acceptable. Some examples of application methods include spray or mist application, application in a wash or rinse cycle during the washing process, application from a sheet of material containing the treatment compound, e.g., in a drier, and application of the treatment composition. Including, but not limited to, immersion in the containing solution.

The preferred method for applying the treatment composition to the material is pump or aerosol spray or mist application or other methods known in the art. One useful method for personal use is spraying or application from a mist bottle. The treatment composition may be applied to garments that are being worn as well as garments that are not being worn. The mist is
For example, it can occur in industrial or consumer equipment designed for an application, such as a machine for handling household clothes or a machine for washing clothes.

The material may be impregnated with an aqueous solution of the treatment composition. As used herein, "impregnation" refers to the penetration of a solution into a fibrous matrix of a material and the distribution of the solution into and through the gap in a preferably substantially uniform manner. The solution wraps, surrounds and / or impregnates the individual fibers substantially throughout the thickness of the material, as opposed to only forming a surface coating of the material.

[0027] The treatment composition can be applied to the textile during the textile manufacturing process as part of a no-iron finishing operation. If the textile is not treated in the textile manufacturing process, the treatment composition is washed, most preferably
It can be applied to rinsing water in the rinsing cycle of the washing process at home or in a coin laundry.

[0028] The treatment composition may also be transferred to the material to be treated by contact with another material impregnated with the treatment composition. One example would be the addition of a sheet containing the treatment composition of the present invention to a dryer or tumble apparatus and transfer of the treatment composition to the laundry by contact in the dryer. Since no heat is required for the method of the invention, this method of application is useful for no heating or low temperature fixation. Application with impregnated sheets may also include using such sheets in home dry cleaning.

Further, the treatment composition may be applied by dipping the textile in a solution containing the treatment composition.

The material treated with the treatment composition of the present invention is dried at ambient temperature without the need for an external heat source. While the application of an external heat source could increase the speed of the drying process,
It is not required for the method of the invention. Such heat sources include, but are not limited to, the temperatures found in clothes dryers.

The hydroxy compound is present in an amount sufficient to provide from about 0.00001 to about 10% of the hydroxy compound to the material, based on the oven dried mass of the material. Preferably, the hydroxy compound is in an amount sufficient to provide from about 0.1 to about 5%, more preferably from about 0.5 to about 2%, by weight of the hydroxy compound, based on the oven-dried weight of the material. Exists.

A dilute solution of the substance is typically sprayed onto the fabric. The spray solution may contain 0.001 to 20% by weight, preferably 0.1 to 10% by weight, most preferably 0.5 to 5% by weight of the hydroxyurea compound.

The treatment composition of the present invention can be formulated as part of a laundry detergent or fabric softener. The treatment composition can be formulated in both liquid and powdered or tableted detergents. Hydroxy compounds are present in detergents or fabric softeners at 0.00
It is present at from 01 to 20%, preferably from 0.1 to 10%, most preferably from 0.5 to 5%. The treatment compositions of the present invention can be incorporated into detergents or fabric softeners using standard methods known in the art. Application of the treatment composition to the material occurs during a normal cleaning and / or rinsing cycle.

The laundry detergent compositions containing the hydroxy compounds of the present invention are typical for laundry detergents, including, but not limited to, surfactants, builders and cobuilders, dispersants, enzymes, fillers and dyes. Components that are specifically found could also be included. In addition to providing reduced wrinkles and improved feel, the hydroxy compounds of the present invention also serve as dissolution aids for detergents in tablet or sachet form, facilitating faster dissolution of hard ingredients into detergent powders. will do.

The hydroxy compound may be encapsulated in a substance such as starch, modified starch, cellulosic, or modified cellulosic for delivery to the material to be treated.

The method of the present invention imparts wrinkle resistance to the treated material. In addition, the treated textile has a tactile sensation of softness and retains smoothness even after washing.

[0037]

The following non-limiting examples illustrate further aspects of the present invention. Example 1 106.2 g of diethanolamine and 61.24 g of urea were charged to a 250 mL flask equipped with a condenser, thermometer, stirrer and nitrogen purge needle. The mixture was heated at 115 ° C. for 5 hours. A nitrogen purge was used to remove the evolving ammonia. 0.1N progress of reaction
The remaining diethanolamine was monitored by titration with hydrochloric acid. Clear water containing N, N-bis (2-hydroxyethyl) urea (hydr
oscopic) liquid was obtained.

Examples 2-7 The following amines were reacted with urea according to the procedure described in Example 1. ─────────────────────────────────── Example amine mass (g) urea (g) ──── ─────────────────────────────── 2 ethanolamine 61 60 3 3-amino-1-propanol 150 60 4 2-amino 2-ethyl-1,3-119 30 propanediol (AEPD) 5 ethanolamine 122 606 diethanolamine 210 60 7 4-aminobutanol 124 ─────────────────

Example 8 212.4 g of diethanolamine in 212.4 g of water was neutralized to pH 4 with 101.85 g of concentrated sulfuric acid. Then a solution of 168.99 g of potassium cyanate in 260 g of water was added and the mixture was heated to 90 ° C. for 3 hours. After cooling to ambient temperature, potassium sulfate precipitated and was filtered off. The filter cake was washed with 425 g hot ethanol. The recovered ethanol was then added to the contents of the filtrate and the filtrate became cloudy. A white precipitate was removed by filtration, and then ethanol was removed by distillation to obtain a viscous liquid solution of N, N-bis (2-hydroxyethyl) urea. Using another acid, such as sulfuric acid, to neutralize the amine, the product could likewise be obtained. Also, other cyanates, such as sodium cyanate, could be used.

Example 9 According to the procedure of Example 8, 195.2 in 200 g of water.
2 g of N-methyl-D-glucamine was reacted with 98.08 g of sulfuric acid. After adjusting the pH to 4, a flask containing 100 g of water was charged with 81.11 g of potassium cyanate. The mixture was heated to 70 ° C. for 2 hours. After cooling to 0 ° C., the precipitated calcium sulfate by-product was removed by filtration. The filtrate was treated with 250 mL of hot methanol and further filtered to remove any residual salt by-product. Next, methanol was removed by vacuum distillation to obtain a solution containing N-methyl-D-glucourea.

Example 10 Using the procedure described in Example 1, the reaction can be effectively carried out using reflux water as a means for removing the generated ammonia. 105 g of diethanolamine, 25 g of water and 60 g of urea were charged into a 250 mL flask equipped with a heating mantle, stirrer and thermometer and reacted at 115 ° C. for 8 hours.

Example 11 A flask equipped with a heating mantle, stirrer and condenser was charged with 210 g of diethanolamine and 90 g of dimethyl carbonate. Fill the contents of the flask with 8
Heated to 0 ° C. and allowed to stir for 3 hours. Volatile by-products,
For example, methanol was removed by vacuum distillation. A mixture containing tetrakis (2-hydroxyethyl) urea was obtained.

Example 12 A solution of 99 g of n-butyl isocyanate in 40 mL of tetrahydrofuran was added over 1 hour to a solution of 106 g of diethanolamine in 700 mL of methanol, keeping the temperature below 30 ° C. After the addition, the mixture was stirred for 1 hour, then the solvent was removed by vacuum distillation to give a white solid, N'-butyl-N, N-bis (2
-Hydroxyethyl) urea was obtained.

Examples 13-14 Following the procedure described in Example 12, the following amines were reacted with isocyanates. ──────────────────────────────────── Example Amine mass (g) Isocyanate mass (g) ── ────────────────────────────────── 13 ethanolamine 61 N-butyl isocyanate 99 14 N-methyl-D- 196 N-butyl isocyanate 99 glucoamine ────────────────────────────────────

Example 15 A 500 mL flask equipped with a stirrer and a condenser was charged with 145.1 g of 40% glyoxal and 90 g of urea. The temperature was kept at 30 ° C. for 6 hours. The resulting solution contained 4,5-dihydroxyimidazolidone.

Example 16 A 15.24 cm (6 inch) by 27.94 cm (11 inch) cotton swatch is sprayed with a solution of the compound of the example so that 7 × 10 ^-4 moles of material are delivered to the fabric. did. Allow the swatch to dry overnight, then use AATC
C (American Association of Textile Chemists and C
olorists) Measured as in Test Method 128-1980. A pairwise comparison of wrinkled swatches was used in place of the standard evaluation method found in Section 6. A less wrinkled swatch was scored 2 and a more wrinkled fabric was assigned a value of 1. Each swatch was given a rating of 1.5 when there was no difference in the appearance of the fabric. The sum of each swatch was added and called the "grading total". By this method, it was found that swatches with higher grade totals were less wrinkled by panelists.

Table 1 ───────────────────────────────── Example Total grade (higher the less wrinkles)） ──────────────────────────────── 126 221 water 15 ──────────── ─────────────────────

Example 16 A 12.7 cm (5 inch) by 12.7 cm (5 inch) size swatch is sprayed with an aqueous solution of the material of the example to a concentration for the swatch as shown in Table 2. did. Samples were equilibrated by conditioning the swatches in a desiccator maintained at a constant humidity level. After conditioning, the fabric sample was loaded on a TGA meter at room temperature, equilibrated at 25 ° C. for 30 seconds, and then heated to 100 ° C. and 105 ° C.
For 10 minutes. The TGA measurement was carried out under the ultra-pure N _2. The instrument detected the mass loss of the sample as a percentage of the total starting sample mass. The experimental error was about 0.5.
The mass loss was found to be due to water loss rather than concomitant decomposition. Total water loss is effectively the absorption of water at 100% relative humidity. The total water absorption for each material is shown in Table 2. Samples treated with the hydroxyurea material were found to absorb more water than untreated samples.

Table 2: Moisture effects of hydroxyurea モ ル moles of substance / G swatch Water absorption relative humidity 100% Substance (mol / g) (mass increase%) ────────────────────────────── ──── 1 5.11 × 10 ⁻³ 40.8 2 5.02 × 10 ⁻³ 42.9 9 5.38 × 10 ⁻³ 54.2 13 5.54 × 10 ⁻³ 33.9 14 5 .15 × 10 ^-3 37.4 12 4.98 × 10 ^-3 31.7 Water 0 14.4 水─────────

Example 18-Tactile sensation of the fabric For the tactile sensation test of the fabric, 3
% (N, N-bis (2-hydroxyethylurea)), Example 2 (N-2-hydroxyethylurea) and Example (N-methyl-D-glucourea). These solutions were sprayed onto a 10 inch square swatch of cotton, 50/50 cotton polyester blend and polyester for 10 seconds. The swatch was then ironed and dried. The panel was asked to evaluate the tactile sensation of the fabric by comparing each sample and the swatches of the same fabric blank that was sprayed with deionized water, ironed and dried. Each individual determined whether the sample was better, worse, or equal to blank.

The results were counted by assigning one point to the sample that felt better than the blank, subtracting one point for the sample with a worse rating than the blank, and giving a zero point to the sample that felt equal to the blank. The total score for each individual sample was then added together. The results are shown in the graph (FIG. 1).

Examples 1 and 2 when applied to cotton
Received the highest score (4 points each). Example 1 received 3 points for poly-cotton and 2 points for polyester. Example 2 scored 2 points for each of poly-cotton and polyester. In Example 9, 2 points were obtained for polyester, 1 point for cotton, and 0 point for poly-cotton, which were insufficient performance.

In order to determine the one with the best overall performance, points were added together for the use of one product for each of the individual fabrics. Example 1 obtained the best overall score of 9 points. Example 2 immediately followed with 8 points. In Example 9, three total scores were obtained. The highest score obtained was 11 points.

After this evaluation, a water drop was placed on each sample,
The percentage of absorption was evaluated visually. Although there appeared to be no difference in the rate at which water was absorbed by the various swatches, Example 2
And the polyester samples ironed in Examples 9 and 1 appeared to dry faster than the blanks.

Example 19 Preparation of Granular Detergent Test Composition A typical intense granular detergent composition can be prepared containing one or more hydroxy compounds of the present invention. All of these granular detergent compositions have the following basic formula: Table 3 成分 Ingredient mass% ─────────── ─────────────────────── C ₁₂ linear alkyl benzene sulfonate 9.31 C _14-15 alkyl ether (0.35E0) sulfate 12.74 zeolite builder 27 2.79 sodium carbonate 27.31 PEG 4000 1.60 dispersant 2.26 C _12-13 alcohol ethoxylate (9E0) 1.5 sodium perborate 1.03 soil release polymer 0.41 enzyme 0.59 hydroxy compound 3. 0 Perfume, whitening agent, suds suppressor, other minor components, moisture, sulfate residue ────────────────────────────── ──── 100%

Example 20 Preparation of a Liquid Detergent Test Composition A typical heavy duty liquid detergent composition can be prepared containing one or more hydroxy compounds of the present invention. All of these granular detergent compositions have the following basic formula: Table 4 ────────────────────────────────── Component mass% ─────────── ─────────────────────── C _12-15 alkyl ether (2.5) sulfate 38 C ₁₂ glucose amide 6.86 citric acid 4.75 C _{12 -14} fatty acid 2.00 enzyme 1.02 MEA 1.0 propanediol 0.36 borax 6.58 dispersant 1.48 Na toluenesulfonate 6.25 hydroxy compound 1.0 dye, fragrance, whitening agent, preservative , Foam inhibitor, other trace components, water residue 100%

Example 21 Preparation of a Granular Detergent Test Composition A typical granular detergent composition can be prepared containing one or more hydroxy compounds of the present invention. All of these granular detergent compositions have the following basic formula: Table 5 成分 Ingredients Example Comparative example (% by mass) (% by mass) ─ Ｎａ NaC ₁₂ linear alkyl benzene sulfonate 9.40 9.40 NaC _14-15 alkyl Sulfonate 11.26 11.26 Zeolite builder 27.79 27.29 Sodium carbonate 27.31 27.31 PEG4000 1.60 1.60 Dispersant, Na polyacrylate 2.26 2.26 C _12-13 alkyl ethoxylate (E9) 1.5 1.5 Sodium perborate 1.03 1.03 Hydroxy compound 2.00 Other additional components Residue Residual ─────────────────── １００ 100% 100%

Example 22 A typical dilute fabric softener formulation is listed below. Table 6 Formulation of diluted traditional softener (single activator) ^{a a} ─ Formulation A 成分 Ingredient% ─────────── ─────────────────────── Distearyl dimethyl ammonium chloride (75% active) 6-9 hydroxy compound 0.1-3.0 fragrance 0.2- 0.5 Colorant 0.001 Water residue ────────────────────────────────── Formulation B Ｂ ────────────────────────────── Quaternary dialkylimidazoline (75% active) 6-9 hydroxy compound 0.1-3 0.0 Perfume 0.2-0.5 Colorant 0.001 Preservative Agent + ──────────────────────────────────

Example 23 Example of a concentrated fabric softener composition Table 7 Rinse conditioner (mixed activator) used three times in concentration ──────────────── Compound C ────────────────────────────────成分 Ingredient% ────────────────────────────────── Distearyl dimethyl ammonium chloride 75% 14 Hydroxy compound 3 Lanolin 2 Ethoxylated fatty acid 4 CaCl ₂ 0.05 Water, fragrance, coloring agent Residue ───────────────────────────────── ─ Formulation D ────────────────────────────────── Distearyl dimethyl ammonium chloride 5 -10 amidoamine 5-10 imidazoline 3.75-5.25 hydroxy compound 0.1-2.0 electrolyte 0.05-0.4 water, fragrance, colorant residue ──────────── ──────────────────────

Example 24 Concentrated Fabric Softener Composition Table 8 Example of Concentrated Biodegradable Formulation ────── Formulation E (product with 37.5% activator) ──────────────────────────────成分 component (%) ア ミ ド amidoamine 23.45 diester 4 (quat ) 14.05 hydroxy compound 1.25 HCl 1.10 CaCl ₂ 0.55 emulsifier 0.5 perfume 2 colorant 0.03 water residue ─────────────── Formulation F ───────────────────────────────── ─ AB ─────────────エ ス テ ル Ester 4 (quat) 52 2 Imidazoline-substituted ester 1730 Isopropanol-1.5 Silicone 0.5-Hydroxy compound 0.250 0.75 polyethylene glycol 1.2 --- coloring agent, fragrance, CaCl ₂ , Na citrate, water residue residue ────────────────────────── ────────

Example 25: Example of sheet composition for dryer

[Table 1]

[Brief description of the drawings]

FIG. 1 shows the tactile panel results of a fabric.

Continuation of front page (72) Inventor Suzanne H. Goodson United States, Pennsylvania 18976, Warrington, Creekside Court 4005 F-term (reference) 4H003 AB19 AB31 AC08 DA01 EA12 EA16 EA20 EA28 EB17 EB18 EB28 EB36 EC01 ED02 EE05 FA21 4L033 AC01 AC04 AC15 BA79

Claims (2)

[Claims] 1. A method of treating a material to reduce wrinkles and provide temporary wrinkle resistance to the material and to improve the tactile sensation, comprising: a) temporarily wrinkling and soiling the material; Applying an effective amount of a treatment composition to impart properties, said treatment composition comprising a hydroxy compound, and b) drying said treatment composition at ambient temperature without the need to apply an external heat source Wherein the hydroxy compound comprises: 1) a hydroxyurea containing one urea and at least one hydroxy moiety or 2) a hydroxyamide containing at least one amide and at least one hydroxyl moiety. The method comprising: 2. The method of claim 1 wherein: a) said (hydroxyalkyl) urea has the structure Wherein R ¹ is CR ⁵ R ⁶ R ⁷ , R ² is H or R ⁵ , R ³ is H or R ⁵ , R ⁴ is H, R
¹ or R ⁵ , wherein R ⁵ is H, CH ₂ OH,
CHR ⁸ CHR ⁹ OH, CHR ⁸ CHR ⁹ CHR ¹⁰ OH
Or C ₁ -C ₄ alkyl, wherein R ⁶ is H, CH ₂ O
H, CHR ⁸ CHR ⁹ OH, CHR ⁸ CHR ⁹ CHR ¹⁰
OH or C ₁ -C ₄ alkyl, and R ⁷ is H, CH
₂ OH, CHR ⁸ CHR ⁹ OH, CHR ⁸ CHR ⁹ CH
R ¹⁰ OH or C ₁ -C ₄ alkyl, wherein R ⁸
Is H, methyl or ethyl, R ⁹ is H, methyl or ethyl, and R ¹⁰ is H, methyl or ethyl), b) said β-hydroxyalkylamide has the structure Wherein A is a bond, hydrogen, a mono- or polyvalent organic radical derived from a saturated or unsaturated alkyl, aryl, tri-lower alkylene amino or ethylenically unsaturated radical containing from 1 to 60 carbon atoms. A radical, R
¹¹ is selected from the group consisting of hydrogen, lower alkyl having 1 to 5 carbon atoms and hydroxyalkyl having 1 to 5 carbon atoms, and R ¹² and R ¹³ are hydrogen, 1 to 5 carbon atoms. Independently selected from the group consisting of straight or branched lower alkyl having one of the R ¹² and R ¹³ radicals, together with the carbon atom to which they are attached, forming a cycloalkyl, wherein n is An integer of 1 or 2; n 'is an integer of 0 to 2; when n' is 0, n
Is 2.).