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US3096524A - Process for improving crease-retention properties of cotton garments - Google Patents

Process for improving crease-retention properties of cotton garments Download PDF

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US3096524A
US3096524A US10212661A US3096524A US 3096524 A US3096524 A US 3096524A US 10212661 A US10212661 A US 10212661A US 3096524 A US3096524 A US 3096524A
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garment
crease
weight
butadiene
cotton
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Louis R Mizell
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Williamson Dickie Manufacturing Co LLC
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Williamson Dickie Manufacturing Co LLC
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    • 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/693—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural or synthetic rubber, or derivatives thereof
    • 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423—Amino-aldehyde resins
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
    • Y10T428/2419—Fold at edge
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
    • Y10T428/24628—Nonplanar uniform thickness material
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31855—Of addition polymer from unsaturated monomers
    • Y10T428/3188—Next to cellulosic

Definitions

  • This invention relates to an improved process for treating cotton garments, to cotton garments having improved crease-retention properties and, more particularly, to a process for treating cotton garments to impart thereto improved crease-retention properties.
  • Fabrics treated in this manner also have other improved properties, such as better shrinkage control, quicker drying, resistance to rotting, etc.
  • these thermosetting resins particularly the reductions in tear and tensile strengths and abrasionwresistance.
  • One principal disadvantage is that pressed creases which are formed in the treated cotton fabrics or garments are not retained after a plurality of washes and, even after the first wash, the crease is not as well defined as it was prior to the washing step.
  • Another object of this invention is to provide a process for forming on a cotton garment, a pressed crease which is resistant to a plurality of subsequent washings and which is still retained by the garment after these washlngs.
  • Still another object of this invention is to provide a cotton garment having a pressed crease formed therein, which crease is resistant to a plurality of launderings and is retained by the garment after each laundering.
  • one feature resides in impregnating the cotton garment with an aqueous emulsion of a mixture of cyclic ethylene urea-formaldehyde resin and from 1 to 2 parts by weight based on the weight of the resin of a butadiene-acrylonitrile copolymer having a 55% to 45% monomer ratio, respectively, extracting the excess mixture therefrom, forming a fold and heat-pressing along the line of fold to form a crease, and then curing the mixture of permanently set the crease therein.
  • Another feature resides in having the treated, creased 3,096,524 Patented July 9, 1963 garment contain about 5% by weight of the cyclic ethylene urea-formaldehyde resin and from about 510%, and preferably 8% by weight of the butadiene-acrylonitrile copolymer, based upon the weight of the dry garment prior to treatment.
  • a pressed crease may be formed in a cotton garment which crease is retained even after the garment is subjected to a plurality of washings or launderings, by first impregnating the garment with an aqueous emulsion vcontaining from 1 to 2 parts of a butadiene-acrylonitrile copolymer (55%-45% monomer ratio) per each part of a idimethyl cyclic ethylene ureaformaldehyde resin, extracting the emulsion to about a 5055% Wet pick-up of liquor, forming a fold in the garment, heat-pressing the fold until dry and curing the mixture on the fabric, the amount of resin and copolymer used in the emulsion being such as to have retained on the finished product about 5% of resin and from about 5 to 10% of the copolymer.
  • the crease-retention prop erties of the garment treated in the manner indicated above, even after numerous washings, are, superior to the same properties in a (fabric treated solely with the resin.
  • the amount of the elastomer is less than the amount of the CEU, namely 1% or 2% of the copolymer per 5% of the CEU resin, the crease retention properties of the garment are unsatisfactory.
  • Example 1 An aqueous emulsion containing the following ingredients was prepared:
  • Cyclic ethylene urea-formaldehyde (Rhonite R1) 20 Butadiene-acrylonitrile (Chemigum 235 CHS) 39 Water 35 35% solution of zinc nitrate (Rohm & Haas Catalyst polymer having a monomer ratio of 55 parts of butadiene to 45 parts of acrylonitrile, with the average particle size of the material being 2,500 Angstroms.
  • the product contains approximately 42% solids and the particles are dispersed in an aqueous medium with an anionic surface-active agent that gives the latex a high salt ion tolerance.
  • a pair of work pants made from tan, Type IV cotton twill cloth No. 9 was immersed in a bath of the above emulsion at room temperature for approximately a minute, until all parts of the garment were saturated. A longer immersion time is not harmful.
  • the work pants were then removed and permitted to drain for a few minutes before being extracted to 50% pick-up of liquor based on the original dry weight of the garment, and then laid out smoothly on a steam press.
  • the head of the steam press was held down until the pants were dry, after which the creased pants were hung vertically in a dryer and subjected to a temperature of 350 F. for five minutes, which cured the mixture and set the crease in the garment.
  • the treated garment had an increased weight, based upon the dry weight of the garment, of approximately 13%, and the increase due to the presence of about 5% by weight f th 3 resin and of about 8% by weight of the butadiene-acrylonitrile copolymer.
  • sodium aluminate was used as the curing catalyst in an amount equivalent to 0.5% of the rubber solids in solution.
  • the latex employed in Examples 4 and 5 is also a butadiene-acrylonitrile copolymer having a monomer ratio of 70-75 parts of the former to -25 parts of the latter, and is supplied by The B. F. Goodrich Company under its trademark Hycar 1571.
  • the triazone of Examples 8 and 9 is formed by reacting a dimethyl urea with a primary amine, such as ethylamine, and then reacting the product, triazone, with two moles of formaldehyde, under alkaline conditions, to produce the wash-wear agent triazone-formaldehyde, having the formula:
  • cotton garment when used in the above disclosure and in the claims, it is to be understood that it also includes garments containing a mixture of cotton and other fibers, but where the garment has most of the characteristics of a cotton garment, including the inability to retain a crease after one washing.
  • the aqueous material of Example 1 will contain a number of adjuvants, including a softener, such as silicone, polyethylene dispersion, cationic surface-active agent, etc., for imparting a soft hand and to improve tear strength and sewability of the fabric; a water-soluble polymer such as polyvinyl alcohol, modified starch or precondensed thermosetting resin, to impart a greater body to the fabric; a soft thermoplastic resin, such as acrylic resin, to improve the abrasion-resistance and tear strength ratio and to im part a soft, full hand; a silicone for durable softness and resistance to water-borne stains; and other additives, including other softeners and lubricants, depending upon the properties desired in the cotton garment.
  • a softener such as silicone, polyethylene dispersion, cationic surface-active agent, etc.
  • a water-soluble polymer such as polyvinyl alcohol, modified starch or precondensed thermosetting resin, to impart a greater body to the fabric
  • a proces for forming, on a cotton garment, a pressed crease which is resistant to a plurality of subsequent washings and which is still retained by the garment after said washings comprising, impregnating said garment with an aqueous'emulsion of a mixture of one part cyclic ethylene urea-formaldehyde resin and from 1 to 2 parts by weight, based upon said resin, of a butadiene-acrylonitrile copolymer having a monomer ratio of 55 parts butadiene to 45 parts of acrylonitrile, extracting excess emulsion from said garment, forming a fold in said garment and heat-pressing said garment along the line of fold to form a crease therein, and subjecting said garment to a temperature sufficient to eflfect curing of the mixture thereon, said treated garment having about 5% by weight of cyclic ethylene urea-formaldehyde and from about 5 to 10% by weight of butadiene-acrylonitrile copolymer thereon, said treated
  • a process for forming, on a cotton garment, a pressed crease which is resistant to a plurality of subsequent washings and which is still retained by the garment after said washings comprising impregnating said garment with a mixture of one part cyclic ethylene ureaformaldehyde resin and from -1 to 2 parts by weight of a butadiene-acrylonitrile copolymer having a monomer ratio of 55 parts butadiene to 45 parts of acrylonitrile, extracting said emulsion until the Weight of said garment is 50% greater than its dry weight, forming a fold in said garment and heat pressing said wet garment along the line of fold until dry to form a crease therein, and subjecting said garment to a temperature suificient to effect curing of the mixture thereon, said treatment garment having about 5% by weight of cyclic ethylene ureaformaldehyde and from about 5% to 10% by weight of butadiene-acrylonitrile copolymer thereon, based upon the dry weight of the garment
  • a cotton garment having a crease formed therein and having improved crease-retention properties, said crease being resistant to a plurality of washings and being substantially retained by said garment after said washings, said garment having cured thereon, as the creaseretaining agent, a mixture of about 5% by weight of cyclic ethylene urea-formaldehyde and from about 5 to 10% by weight of butadiene-acrylonitrile having a monomer ratio of 55 parts butadiene to 45 parts acrylonitrile, said crease being formed in said garment prior to the curing of said mixture.
  • a cotton garment having a pressed crease formed therein and having improved crease-retention properties, said pressed crease being resistant to a plurality of washings and being substantially retained by said garment after said washings, said garment having cured thereon,
  • crease-retaining agent a mixture of about 5% by weight of cyclic ethylene urea-formaldehyde and about 5% by weight of butadiene-acrylonitrile copolymer having a monomer ratio of 55 parts butadiene to parts acrylonitrile, said pressed crease being formed in said garment prior to the curing of said mixture.
  • a cotton garment having a pressed crease formed therein and having improved crease-retention properties, said pressed crease being resistant to a plurality of washings and being substantially retained by said garment after said washings, said garment having cured thereon, as the crease-retaining agent, a mixture of about 5% by weight of cyclic ethylene urea-formaldehyde and about 8% by weight of butadiene-acrylonitrile copolymer having a monomer ratio of parts butadiene to 45 parts acrylonitrile, said pressed crease being formed in said garment prior to the curing of said mixture.
  • a cotton garment having a pressed crease formed therein and having improved crease-retention properties, said pressed crease being resistant to a plurality of washings and being substantially retained by said garment after said washings, said garment having cured thereon, as the crease-retaining agent, a mixture of about 5% by weight of cyclic ethylene urea-formaldehyde and about 10% by weight of butadiene-acrylonitrile copolymer having a monomer ratio of 55 parts butadiene to 45 parts acrylonitrile, said pressed crease being formed in said garment prior to the curing of said mixture.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

United States Patent 3,096,524 PROCESS FOR IMPROVING CREASE-RETENTION PROPERTIES OF COTTON GARMENTS Louis R. Mizell, Springfield, Md., assignor to Williamson- Dickie Manufacturing Company, Fort Worth, Tex., a corporation of Texas No Drawing. Filed Apr. 11, 1961, Ser. No. 102,126
12 Claims. (Cl. 2-243) This invention relates to an improved process for treating cotton garments, to cotton garments having improved crease-retention properties and, more particularly, to a process for treating cotton garments to impart thereto improved crease-retention properties.
The use of various classes of chemicals or polymerizable resins for treating cellulosic textile materials, particularly cotton, to impart crease resistance and improved wash-and-wear properties thereto is well known. These chemicals and resins include formaldehyde, lglyoxal, acrolein, various urea-fiormaldehydes including dimethylol cyclic ethylene urea resins (CEU), melamine and modified melamine formaldehydes, epoxy resins and others of the thermosetting resins which can be condensed with aldehydes :or which can be polymerized on cotton with reaction to the cellulose molecules, or which can react without polymerization to cross-link cellulose molecules.
Fabrics treated in this manner also have other improved properties, such as better shrinkage control, quicker drying, resistance to rotting, etc. However, there are also certain undesirable eifects from the use of these thermosetting resins, particularly the reductions in tear and tensile strengths and abrasionwresistance. One principal disadvantage is that pressed creases which are formed in the treated cotton fabrics or garments are not retained after a plurality of washes and, even after the first wash, the crease is not as well defined as it was prior to the washing step. Since the garments or fabrics already have been treated with a crease-resistant or wrinkle-resistant resin, it is extremely ldiflicult to improve the appearance of the crease after the fabrics have been washed, since the fabric tends to resist the imparting of a crease thereto.
The importance of a commercial process which will enable creases to be applied to cotton garments, such as work-pants, work-shirts, pleated blouses and skirts, slacks, and the like, which creases will be substantially retained by the garments even after a plurality of washings and launderings, is readily evident.
Accordingly, it is an object of this invention to treat cotton garments to impart to them improved creaseretenti-on properties.
Another object of this invention is to provide a process for forming on a cotton garment, a pressed crease which is resistant to a plurality of subsequent washings and which is still retained by the garment after these washlngs.
Still another object of this invention is to provide a cotton garment having a pressed crease formed therein, which crease is resistant to a plurality of launderings and is retained by the garment after each laundering.
In attaining the objects of this invention, one feature resides in impregnating the cotton garment with an aqueous emulsion of a mixture of cyclic ethylene urea-formaldehyde resin and from 1 to 2 parts by weight based on the weight of the resin of a butadiene-acrylonitrile copolymer having a 55% to 45% monomer ratio, respectively, extracting the excess mixture therefrom, forming a fold and heat-pressing along the line of fold to form a crease, and then curing the mixture of permanently set the crease therein.
Another feature resides in having the treated, creased 3,096,524 Patented July 9, 1963 garment contain about 5% by weight of the cyclic ethylene urea-formaldehyde resin and from about 510%, and preferably 8% by weight of the butadiene-acrylonitrile copolymer, based upon the weight of the dry garment prior to treatment.
Other objects, features, and advantages of the invention will be more apparent from the disclosure herein.
It has been found that a pressed crease may be formed in a cotton garment which crease is retained even after the garment is subjected to a plurality of washings or launderings, by first impregnating the garment with an aqueous emulsion vcontaining from 1 to 2 parts of a butadiene-acrylonitrile copolymer (55%-45% monomer ratio) per each part of a idimethyl cyclic ethylene ureaformaldehyde resin, extracting the emulsion to about a 5055% Wet pick-up of liquor, forming a fold in the garment, heat-pressing the fold until dry and curing the mixture on the fabric, the amount of resin and copolymer used in the emulsion being such as to have retained on the finished product about 5% of resin and from about 5 to 10% of the copolymer. The crease-retention prop erties of the garment treated in the manner indicated above, even after numerous washings, are, superior to the same properties in a (fabric treated solely with the resin. However, when the amount of the elastomer is less than the amount of the CEU, namely 1% or 2% of the copolymer per 5% of the CEU resin, the crease retention properties of the garment are unsatisfactory.
The following example is merely illustrative of an embodiment of the invention, and is not to be considered as limiting the invention in any manner.
Example 1 An aqueous emulsion containing the following ingredients was prepared:
Parts by weight Cyclic ethylene urea-formaldehyde (Rhonite R1) 20 Butadiene-acrylonitrile (Chemigum 235 CHS) 39 Water 35 35% solution of zinc nitrate (Rohm & Haas Catalyst polymer having a monomer ratio of 55 parts of butadiene to 45 parts of acrylonitrile, with the average particle size of the material being 2,500 Angstroms. The product contains approximately 42% solids and the particles are dispersed in an aqueous medium with an anionic surface-active agent that gives the latex a high salt ion tolerance.
A pair of work pants made from tan, Type IV cotton twill cloth No. 9 was immersed in a bath of the above emulsion at room temperature for approximately a minute, until all parts of the garment were saturated. A longer immersion time is not harmful. The work pants were then removed and permitted to drain for a few minutes before being extracted to 50% pick-up of liquor based on the original dry weight of the garment, and then laid out smoothly on a steam press. The head of the steam press was held down until the pants were dry, after which the creased pants were hung vertically in a dryer and subjected to a temperature of 350 F. for five minutes, which cured the mixture and set the crease in the garment. The treated garment had an increased weight, based upon the dry weight of the garment, of approximately 13%, and the increase due to the presence of about 5% by weight f th 3 resin and of about 8% by weight of the butadiene-acrylonitrile copolymer.
Several pairs of cotton twill work pants were treated in the manner disclosed in Example 1, except that the treated garments having the pressed crease therein had different proportions of resin and butadiene-acrylonitrile copolymers cured thereon, or else the garments were treated with the resin alone or elastomer alone. The garments were washed and tumble-dried once and the creases compared, and then were washed and tumble-dried a total of twenty times and the creases compared. The results are set forth in the following table:
From the above table, it will be noted that the pressed crease retention of the garments treated in accordance with the invention, Examples 6 and 7, is greater after being laundered twenty times than is the pressed crease retention of the fabric treated with the resin of Example 2 after only one laundering.
Since no resin was present for Examples 4 and 5, sodium aluminate was used as the curing catalyst in an amount equivalent to 0.5% of the rubber solids in solution.
The latex employed in Examples 4 and 5 is also a butadiene-acrylonitrile copolymer having a monomer ratio of 70-75 parts of the former to -25 parts of the latter, and is supplied by The B. F. Goodrich Company under its trademark Hycar 1571. The triazone of Examples 8 and 9 is formed by reacting a dimethyl urea with a primary amine, such as ethylamine, and then reacting the product, triazone, with two moles of formaldehyde, under alkaline conditions, to produce the wash-wear agent triazone-formaldehyde, having the formula:
When the term cotton garment is used in the above disclosure and in the claims, it is to be understood that it also includes garments containing a mixture of cotton and other fibers, but where the garment has most of the characteristics of a cotton garment, including the inability to retain a crease after one washing.
It will be apparent that for commercial applications, the aqueous material of Example 1 will contain a number of adjuvants, including a softener, such as silicone, polyethylene dispersion, cationic surface-active agent, etc., for imparting a soft hand and to improve tear strength and sewability of the fabric; a water-soluble polymer such as polyvinyl alcohol, modified starch or precondensed thermosetting resin, to impart a greater body to the fabric; a soft thermoplastic resin, such as acrylic resin, to improve the abrasion-resistance and tear strength ratio and to im part a soft, full hand; a silicone for durable softness and resistance to water-borne stains; and other additives, including other softeners and lubricants, depending upon the properties desired in the cotton garment.
While zinc nitrate has been disclosed as the catalyst, other known catalysts for the C-EU may be used.
Having fully described the invention, what is claimed is:
1. A proces for forming, on a cotton garment, a pressed crease which is resistant to a plurality of subsequent washings and which is still retained by the garment after said washings, comprising, impregnating said garment with an aqueous'emulsion of a mixture of one part cyclic ethylene urea-formaldehyde resin and from 1 to 2 parts by weight, based upon said resin, of a butadiene-acrylonitrile copolymer having a monomer ratio of 55 parts butadiene to 45 parts of acrylonitrile, extracting excess emulsion from said garment, forming a fold in said garment and heat-pressing said garment along the line of fold to form a crease therein, and subjecting said garment to a temperature sufficient to eflfect curing of the mixture thereon, said treated garment having about 5% by weight of cyclic ethylene urea-formaldehyde and from about 5 to 10% by weight of butadiene-acrylonitrile copolymer thereon, based upon the dry weight of the garment.
2. The process for forming, on a cotton garment, a crease which is resistant to a plurality of subsequent washings and which is still retained by the garment after said washings, as defined in claim 1, wherein the amount of said mixture remaining on said garment after said treatment is about 5% by weight of said cyclic ethylene ureaformaldehyde and about 8% by weight of the butadieneacrylonitrile copolymer, based upon the dry weight of the garment.
3. The process for forming, on a cotton garment, a crease which is resistant to a plurality of subsequent washings and which is still retained by the garment after said washings, as defined in claim 1, wherein the amount of said mixture remaining on said garment after said treatment is about 5% by weight of said cyclic ethylene urea-formaldehyde and about 5% by weight of the butadiene-acrylonitrile copolymer, based upon the dry weight of the garment.
4. The process for forming, on a cotton garment, a crease which is resistant to a plurality of subsequent washings and which is still retained by the garment after said washings, as defined in claim 1, wherein the amount of said mixture remaining on said garment after said treatment is about 5% by weight of said cyclic ethylene urea-formaldehyde and about 10% by weight of the butadiene-acrylonitrile copolymer, based upon the dry weight of the garment.
5. A process for forming, on a cotton garment, a pressed crease which is resistant to a plurality of subsequent washings and which is still retained by the garment after said washings, comprising impregnating said garment with a mixture of one part cyclic ethylene ureaformaldehyde resin and from -1 to 2 parts by weight of a butadiene-acrylonitrile copolymer having a monomer ratio of 55 parts butadiene to 45 parts of acrylonitrile, extracting said emulsion until the Weight of said garment is 50% greater than its dry weight, forming a fold in said garment and heat pressing said wet garment along the line of fold until dry to form a crease therein, and subjecting said garment to a temperature suificient to effect curing of the mixture thereon, said treatment garment having about 5% by weight of cyclic ethylene ureaformaldehyde and from about 5% to 10% by weight of butadiene-acrylonitrile copolymer thereon, based upon the dry weight of the garment.
6. The process for forming, on a cotton garment, a crease which is resistant to a plurality of subsequent washings and which is still retained by the garment after said washings, as defined in claim 5, wherein the amount of said mixture remaining on said garment after said treatment is about 5% by weight of said cyclic ethylene urea-formaldehyde and about 8% by weight of the butadiene-acrylonitrile copolymer, based upon the dry weight of the garment.
7. The process for forming, on a cotton garment, a crease which is resistant to a plurality of subsequent washings and which is still retained by the garment after said washings, as defined in claim 5, wherein the amount of said mixture remaining on said garment after said treatment is about by weight of said cyclic ethylene urea-formaldehyde and about 5% by weight of the butadiene-acrylonitrile copolymer, based upon the dry weight of the garment.
8. The process for forming, on a cotton garment, a crease which is resistant to a plurality of subsequent washings and which is still retained by the garment after said washings, as defined in claim 5, wherein the amount of said mixture remaining on said garment after said treatment is about 5% by weight of said cyclic ethylene urea-formaldehyde and about by weight of the butadiene-acrylonitrile copolymer, based upon the dry weight of the garment.
9. A cotton garment having a crease formed therein and having improved crease-retention properties, said crease being resistant to a plurality of washings and being substantially retained by said garment after said washings, said garment having cured thereon, as the creaseretaining agent, a mixture of about 5% by weight of cyclic ethylene urea-formaldehyde and from about 5 to 10% by weight of butadiene-acrylonitrile having a monomer ratio of 55 parts butadiene to 45 parts acrylonitrile, said crease being formed in said garment prior to the curing of said mixture.
10. A cotton garment having a pressed crease formed therein and having improved crease-retention properties, said pressed crease being resistant to a plurality of washings and being substantially retained by said garment after said washings, said garment having cured thereon,
6 as the crease-retaining agent, a mixture of about 5% by weight of cyclic ethylene urea-formaldehyde and about 5% by weight of butadiene-acrylonitrile copolymer having a monomer ratio of 55 parts butadiene to parts acrylonitrile, said pressed crease being formed in said garment prior to the curing of said mixture.
11. A cotton garment having a pressed crease formed therein and having improved crease-retention properties, said pressed crease being resistant to a plurality of washings and being substantially retained by said garment after said washings, said garment having cured thereon, as the crease-retaining agent, a mixture of about 5% by weight of cyclic ethylene urea-formaldehyde and about 8% by weight of butadiene-acrylonitrile copolymer having a monomer ratio of parts butadiene to 45 parts acrylonitrile, said pressed crease being formed in said garment prior to the curing of said mixture.
12. A cotton garment having a pressed crease formed therein and having improved crease-retention properties, said pressed crease being resistant to a plurality of washings and being substantially retained by said garment after said washings, said garment having cured thereon, as the crease-retaining agent, a mixture of about 5% by weight of cyclic ethylene urea-formaldehyde and about 10% by weight of butadiene-acrylonitrile copolymer having a monomer ratio of 55 parts butadiene to 45 parts acrylonitrile, said pressed crease being formed in said garment prior to the curing of said mixture.
Warnock et al. Mar. 14, 1961

Claims (1)

1. A PROCES FOR FORMING, ON A COTTON GARMENT, A PRESS CREASE WHICH IS RESISTANT TO A PLURALITY OF SUBSEQUENT WASHINGS AND WHICH IS STILL RETAINED BY THE GARMENT AFTER SAID WASHINGS, COMPRISING, IMPREGNATING SAID GARMENT WITH AN AQUEOUS EMULSION OF A MIXTURE OF ONE PART CYCLIC ETHYLENE UREA-FORMALDEHYDE RESIN AND FROM 1 TO 2 PARTS BY WEIGHT, BASED UPON SAID RESIN, OF A BUTADIENE-ACRYLONITRILE COPOLYMER HAVING A MONOMER RATIO OF 55 PARTS BUTADIENE TO 45 PARTS OF ACRYLONITRILE, EXTRACTING EXCESS EMULSION FROM SAID GARMENT, FORMING A FOLD IN SAID GARMENT AND HEAT-PRESSING SAID GARMENT ALONG THE LINE OF FOLD TO FORM A CREASE THEREIN, AND SUBJECTING SAID GARMENT TO A TEMPERATURE SUFFICIENT TO EFFECT CURING OF THE MIXTURE THEREON, SAID TREATED GARMENT HAVING ABOUT 5% BY WEIGHT OF CYCLIC ETHYLENE UREA-FORMALDEHYDE AND FROM ABOUT 5 TO 10% BY WEIGHT OF BUTADIENE-ACRYLONITRILE COPOLYMER THEREON, BASED UPON THE DRY WEIGHT OF THE GARMENT.
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Cited By (14)

* Cited by examiner, † Cited by third party
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US3268915A (en) * 1963-04-08 1966-08-30 Koratron Company Inc Process of manufacturing press-free garment with retained creases
US3284391A (en) * 1962-04-02 1966-11-08 Dow Corning Dispersions for treating fabrics
US3288553A (en) * 1964-09-21 1966-11-29 Beacon Mfg Co Process for treating napped fabrics
US3402988A (en) * 1965-04-02 1968-09-24 Agriculture Usa Chemical deactivation of catalyst at both faces of a cellulosic fabric impregnated with a resin-catalyst system to improve abrasion resistance of fabric after curing
US3425856A (en) * 1964-09-15 1969-02-04 Riegel Textile Corp Process for producing permanent creases and other desirable properties in textile fabrics
US3432862A (en) * 1966-03-04 1969-03-18 Harry H Weiler Adjustable size garment
US3440198A (en) * 1966-02-15 1969-04-22 Ironees Co Composition for conferring wrinkle resistant properties to fabric and method for preparng the same
US3530510A (en) * 1968-05-06 1970-09-29 Burlington Industries Inc Durable press process
US3531806A (en) * 1966-06-24 1970-10-06 Metro Atlantic Inc Production of durable shaped fabric articles using two-stage curing
US3731411A (en) * 1971-06-11 1973-05-08 Burlington Industries Inc Process for producing durable press textiles
US3862073A (en) * 1971-07-05 1975-01-21 Heinz Bille Emulsifier compositions for creaseproofing textile materials which contain copolymers of unsaturated carboxylic acids and their esters
US3865621A (en) * 1969-08-15 1975-02-11 Ciba Geigy Ag Treatment of fibrous materials
WO2004048677A1 (en) * 2002-11-26 2004-06-10 Koninklijke Philips Electronics N.V. Compound and method to improve wrinkle resistance in fabrics, and fabric provided with said compound
US20060108560A1 (en) * 2002-08-21 2006-05-25 Mavinkurve Amar A Composition for improving wrinkle resistance in fabrics, wrinkle-reducing active ingredient as used in such a composition, and cartridge containing such composition

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US2383425A (en) * 1942-05-21 1945-08-21 Goodrich Co B F Polymerization of unsaturated organic compounds
US2431001A (en) * 1945-04-27 1947-11-18 Du Pont Coated fabric
US2974432A (en) * 1956-02-20 1961-03-14 Koret Of California Press-free crease retained garments and method of manufacture thereof
US2917412A (en) * 1958-05-12 1959-12-15 Robert M Reinhardt Process for the production of cellulosic textiles with permanent creases and improved soil and abrasion resistance

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3284391A (en) * 1962-04-02 1966-11-08 Dow Corning Dispersions for treating fabrics
US3268915A (en) * 1963-04-08 1966-08-30 Koratron Company Inc Process of manufacturing press-free garment with retained creases
US3425856A (en) * 1964-09-15 1969-02-04 Riegel Textile Corp Process for producing permanent creases and other desirable properties in textile fabrics
US3288553A (en) * 1964-09-21 1966-11-29 Beacon Mfg Co Process for treating napped fabrics
DE1294925B (en) * 1964-09-21 1969-05-14 Beacon Mfg Company Process for finishing textile fabrics with a pile ceiling
US3402988A (en) * 1965-04-02 1968-09-24 Agriculture Usa Chemical deactivation of catalyst at both faces of a cellulosic fabric impregnated with a resin-catalyst system to improve abrasion resistance of fabric after curing
US3440198A (en) * 1966-02-15 1969-04-22 Ironees Co Composition for conferring wrinkle resistant properties to fabric and method for preparng the same
US3432862A (en) * 1966-03-04 1969-03-18 Harry H Weiler Adjustable size garment
US3531806A (en) * 1966-06-24 1970-10-06 Metro Atlantic Inc Production of durable shaped fabric articles using two-stage curing
US3530510A (en) * 1968-05-06 1970-09-29 Burlington Industries Inc Durable press process
US3865621A (en) * 1969-08-15 1975-02-11 Ciba Geigy Ag Treatment of fibrous materials
US3731411A (en) * 1971-06-11 1973-05-08 Burlington Industries Inc Process for producing durable press textiles
US3862073A (en) * 1971-07-05 1975-01-21 Heinz Bille Emulsifier compositions for creaseproofing textile materials which contain copolymers of unsaturated carboxylic acids and their esters
US20060108560A1 (en) * 2002-08-21 2006-05-25 Mavinkurve Amar A Composition for improving wrinkle resistance in fabrics, wrinkle-reducing active ingredient as used in such a composition, and cartridge containing such composition
WO2004048677A1 (en) * 2002-11-26 2004-06-10 Koninklijke Philips Electronics N.V. Compound and method to improve wrinkle resistance in fabrics, and fabric provided with said compound
US20060123555A1 (en) * 2002-11-26 2006-06-15 Koninklijke Philips Electronics N.V. Compound and method to improve wrinkle resistance in fabrics, and fabric provided with said compound
US7815691B2 (en) * 2002-11-26 2010-10-19 Koninklijke Philips Electronics N.V. Compound and method to improve wrinkle resistance in fabrics, and fabric provided with said compound

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