[go: up one dir, main page]
More Web Proxy on the site http://driver.im/

US3731411A - Process for producing durable press textiles - Google Patents

Process for producing durable press textiles Download PDF

Info

Publication number
US3731411A
US3731411A US00152428A US3731411DA US3731411A US 3731411 A US3731411 A US 3731411A US 00152428 A US00152428 A US 00152428A US 3731411D A US3731411D A US 3731411DA US 3731411 A US3731411 A US 3731411A
Authority
US
United States
Prior art keywords
percent
fabric
durable press
textile
article
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.)
Expired - Lifetime
Application number
US00152428A
Inventor
R Barber
G Moses
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.)
BI/MS HOLDINGS I Inc A DE CORP
Original Assignee
Burlington Industries Inc
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 Burlington Industries Inc filed Critical Burlington Industries Inc
Application granted granted Critical
Publication of US3731411A publication Critical patent/US3731411A/en
Assigned to BI/MS HOLDINGS I INC., A DE. CORP. reassignment BI/MS HOLDINGS I INC., A DE. CORP. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: BURLINGTON INDUSTRIES, INC.,
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof

Definitions

  • Procedures for preparing such textiles involve applying an aqueous composition containing a durable press reactant to cellulosic fabric, drying, pressing and curing.
  • a durable press garment When a durable press garment is to be made, the dried fabric is usually cut and sewn into the desired form, e.g., pants, and then pressed and cured. Pressing and curing may be carried out simultaneously at relatively high temperatures (see U. S. Pat. No. 2,950,553) although the more widely practiced technique is to press the garment at a somewhat lower temperature (such as 300335F.) using, for example, a hot head press, followed by a separate baking or curing operation in an oven at higher temperatures (e.g., 350375 F.).
  • U. S. Pat. No. 3,341,955 describes the preparation of durable press garments from 100 percent cotton fabrics by padding the fabric with an aqueous durable press reactant finish, drying and curing. Thereafter, when a garment with a permanent crease is to be made, the area where the crease is desired is treated with acid catalyst and pressed at high temperature (350F. or above).
  • the procedures which involve oven baking also have economic disadvantages, not only in the cost and maintenance of the ovens, but in the relatively long time required (-15 minutes) to accomplish the desired cure.
  • the curing time also has an undesirable effect on fabric color, e.g., hue or cast may be changed and/or whites may be caused to yellow.
  • the simultaneous press/cure procedures are generally free from these problems but they suffer from other disadvantages and,
  • the principal object of the present invention is to provide durable press textiles and procedures for making the same whereby the above-noted problems with prior procedures are eliminated or substantially reduced.
  • a further object is to provide cellulosic fabrics which have, in addition to an outstanding durable press, other improved physical and aesthetic properties.
  • Still another object of the invention is to provide a process for obtaining durable press effects on cellulosic textiles using less severe press/cure conditions than previously utilized, with resultant improvement in the overall properties of the product.
  • a more specific object is to provide a durable press finish and process whereby pressing and curing may be effectively carried out simultaneously on the press using lower temperatures and shorter times than normally considered feasible.
  • the objects of the invention are realized by treating the fabric with an aqueous formulation of one or more low temperature crosslinking film-forming acrylic polymers, a durable press thermosetting fiber-reactive resin and a curing or cross-linking agent; drying, pressing and curing, the fabric being formed into a garment or other article (e.g., sheets) before the pressing and curing.
  • an aqueous formulation of one or more low temperature crosslinking film-forming acrylic polymers, a durable press thermosetting fiber-reactive resin and a curing or cross-linking agent drying, pressing and curing, the fabric being formed into a garment or other article (e.g., sheets) before the pressing and curing.
  • a mixture of crosslinking acrylic polymers is used and/or the formulation includes a heat curable or crosslinking elastomer hand builder as described below.
  • an advantage of the invention is that pressing and curing can be carried out simultaneously using relatively moderate times and temperatures with resultant improvement in the properties of the treated fabric.
  • fabric processed according to the invention can be presscured on a hot head press at temperatures not exceeding 345F., typically in the range of 300F. to 345F. and in some instances even lower (280-290F.) using normal pressing times such as 15 seconds (usually 5 seconds steam, 5 seconds vacuum and 5 seconds dry) to give highly durable'creases and wash and wear properties in the pressed fabric.
  • aesthetic properties such as hand, feel and color and physical characteristics, e.g., tensile strength, tear and abrasion resistance, are not undesirably affected.
  • the success of the invention is due, at least in large measure, to the use of the low temperature crosslinking acrylic polymer in combination with the durable press fiber reactant and curing agent. It is not understood how or why the indicated components function to give the stated results but it is apparent, in any event, that this combination must be used to obtain the overall results of the invention. It appears that the indicated components somehow work together in a synergistic fashion to give the results indicated since durable press properties, for example, exceed those which would be expected from the normal additive effect of the individual components.
  • the acrylic polymer used herein may be defined as a copolymer of a lower alkyl ester of acrylic acid or methacrylic acid, or like monoethyleneically unsaturated compound, with another monomer eopolymerizable therewith and additionally including where R is an alkenyl group having 3 to 9 carbon atoms and a terminal group of the formula HzC;C Miami- R is H, CH Ol-l, or Cl-l OR" wherein R is the hydrocarbon residue of a saturated alcohol R"OH having one to eight carbon atoms, R is H, CH OH, or CH OR" R is H, CH OH, or CH OR", and R is H, CH OH, or Cl-l OR", and 2.
  • Such polymers may have molecular weights in the order of 1,000 to I ,O00,000 and are available in latex or emulsion form.
  • a particularly preferred low temperature crosslinking acrylic copolymer for use herein is the product of Example of U.S. Pat. No. 3,446,777 but using butyl acrylate instead of the ethyl acrylate referred to therein (i.e. the copolymer of butyl acrylate and methylolated-4-pentenoguanamine) with the pH modified from 5.4 to 9.0 by addition of ammonia to improve emulsion stability.
  • Similar copolymers of methylolated-4-pentenoguanamine with, for example, ethyl acrylate or other lower alkyl acrylates may also be used.
  • an especially useful embodiment of the invention contemplates using a mixture of the low temperature crosslinking acrylic copolymer of a lower alkyl acrylate and methylolated- 4-pentenoguanamine as described above together with the water insoluble, water-dispersible low temperature self-crosslinking acrylic copolymers of a lower alkyl acrylate (e.g., ethyl or butyl acrylate) and an N- methylolacrylamide as described in U.S. Pat. No. 3,157,562, e.g., the copolymer of 90-99 percent lower alkyl acrylate, l-lO percent N-methylolacrylamide and optionally from 0-3 percent acrylamide.
  • a lower alkyl acrylate e.g., ethyl or butyl acrylate
  • N- methylolacrylamide as described in U.S. Pat. No. 3,157,562
  • a curable elastomer or like hand builder is included in the durable press formulation.
  • the elastomer component if used, is most desirably a heat curable polyester elastomer hand builder although other elastomers may be used.
  • the term elastomer as used herein has the meaning given by The American Society for Testing Materials as described in the Encyclopedia of Chemical Technology, 2nd Edition, Volume 7, page 676.
  • elastomers may be used for present purposes, although they are primarily grouped into several recognized categories. As indicated, the preferred category comprises the polyester elastomers including Paraplex rubbers (see Industrial and Engineering Chemistry, Volume 39, page 1090 (1947), Norepal polyester rubbers derived from ethylene glycol and dimeric soya beam fatty acids, copolymer of terephthalic acid and acyclic dicarboxylic acid and a glycol (see U.S. Pat. Nos.
  • polyesters linked together by diisocyanates for example, polyethylene adipate linked by 1,5-naphthalene diisocyanate (see Polyesters and their Applications," by Bjorksten et al., 1956, page 226). These are related to polyurethane elastomers which are cross-linked by diisocyanates.
  • heat-curable elastomers which may be used herein, in lieu of or in addition to a polyester elastomer, include, for example, acrylic elastomers, olefin polymers and the homopolymers and copolymers of dienes such as butadiene, isoprene and chloroprene.
  • the acrylic elastomers are addition type polymers and copolymers which contain a predominant amount of an acrylic acid ester with an alcohol having two or more carbon atoms such as ethyl acrylate or butyl acrylate.
  • These may be crosslinked through the hydrogen atom adjacent the carboxyl group of the acrylic acid moiety by means of a peroxide or by including a small amount (e.g., about 5 percent) of functional groups such as olefinic groups, halogen, carboxyl and cyano.
  • the olefin elastomers include ethylene-propylene rubber and butyl rubber.
  • Ethylene-propylene rubber typically contains 40-70 percent ethylene, the balance being propylene.
  • Butyl rubber typically comprises 0.5-2.5 percent molar isoprene, balance isobutene.
  • Polyvinyl alcohol, polyvinyl acetate and the like may also be included in the formulation along with conventional types of softeners, surfactants, etc.
  • the durable press reactant component of the present finish any of the conventional durable press, reactant resins may be used.
  • the resin is a water-soluble precondensate of formaldehyde with such amino compounds as urea, thiourea, cyclic ethylene ureas (e.g., dimethylol cyclic ethylene urea or dimethylol dihydroxy cyclic ethylene urea), melamine, ethyl carbamate, urons, triazones and triazines or mixtures thereof. Blocked isocyanates may also be effectively used.
  • Suitable crosslinking or curing catalysts for use herein include, without being limited thereto, magnesium chloride or nitrate or zinc chloride or nitrate; various amine hydrochlorides such as 2-amino-2-methyl-lpropanol hydrochloride, or triethanol-amine hydrochloride; and ammonium salts such as ammonium chloride, tartrate, citrate, formate, oxalate, nitrate or ammonium ethyl phosphate or ammonium dihydrogen phosphate or the like.
  • catalysts may be combined, e.g., zinc nitrate and ammonium chloride may be used together, and/or catalyst modifiers may be included as necessary to achieve desired effects, e.g., to increase or decrease catalyst activity. It is particularly useful to employ citric acid in conjunction with zinc chloride, or other catalyst since the citric acid makes it possible to effectively utilize even lower pressing temperatures, e.g., 280F., as described later herein.
  • additives such as boric acid, the latter being useful to avoid any tendency of the pressed fabric to yellow in the event of an after-curing operation.
  • the finish of the invention will comprise, on a weight basis, from 3-20 percent of the low temperature cross-linking acrylic polymer or mixtures thereof, -15 percent, preferably 5-10 percent heat curable elastomer; 3-25 percent durable press resin; and 0.1-7 percent catalyst, balance water. Additionally, the finish may include from O to 5 percent (usually 0.2-2 percent) surfactant, and from O-lO percent of other conventional durable press components such as extenders, softeners or the like.
  • the finish is applied to the fabric in any convenient fashion, e.g., by dipping or spraying but preferably by padding.
  • the amount of the finish applied can be widely varied and is dependent on such factors as the nature and construction of the fabric, its intended use, etc. Usually, however, wet pickup will fall in the range of 30-75 percent by weight of the fabric.
  • the thus-treated fabric is then dried, usually at l90-220F. for 1-5 minutes, to a moisture content in the order of 5-l 0 percent by weight.
  • the dried fabric is then cut into the desired shape, sewn into a garment or other article and pressed on a hot head press or the equivalent.
  • Typical pressing conditions comprise pressing on the hot head press at 300345F. for up to seconds or so. Curing or baking in an oven is not necessary since, with the finish of the invention, durable press effects are obtained by pressing only. However, if desired, the pressed article may be baked under proper conditions without serious disadvantages. If, as in some cases, it is desired to produce an excellent wash and wear fabric, then fabrics treated with this finish can be precured or cured in the finishing plant at 280-345F. for 30 to 180 seconds.
  • EXAMPLE 1 The following formulation was prepared in warm water (e.g., 8 O-l00F.) by adding the components in the order listed to sufficient water to give the indicated percent concentration.
  • Component (1) N,N-dimethylol dihydroxyethylene urea, 50 percent solution in water;
  • Component (2) a polyester of phthalic anhydride, polyethylene glycol and glycerides of hydrogenated fatty acids (commercially available as Discol 716);
  • Component (3) the product of Example 10 of US. Pat. No. 3,446,777 with the substitution of butyl acrylate for the ethyl acrylate used in Example 10 and with adjustment of the pH of the emulsion to 9 by addition of ammonia to stabilize the emulsion;
  • Component (4) an aqueous emulsion of /25 ethyl acrylate/vinyl acetate copolymer, solids content 40 percent (commercially available as Wicaset P.E.P.);
  • Component (5) crude dimethyldistearylammonium hydrogen sulfate, the stearyl groups being predominant in a mixture of higher alkyl radicals derived from hydrogenated tallow.
  • specimens (A) (D) demonstrated effective durable press and wash/wear properties notwithstanding the fact that the specimens were only pressed on the hot head press to obtain these properties.
  • the laundered specimens were also characterized by outstanding physical and aesthetic properties, e.g., abrasion resistance, tensile and tear strength, hand, feel and the like.
  • Example 1 was repeated except that the formulation was changed to include 20 percent of the glyoxal resin (1), rather than 5 percent; and the polyester resin (2) and acrylic ester emulsion (4) were replaced by 5 percent self-crosslinking acrylic emulsion (6), namely, an aqueous emulsion of a copolymer of butyl acrylate and an N -methylolacrylamide per US. Pat. No. 3,157,562.
  • wash/wear, crease and shrinkage values are satisfactorily within acceptable limits for these properties.
  • Example 2 was repeated except that the amount of zinc chloride catalyst was increased to 6 percent and the amount of selfcrosslinking acrylic emulsion was reduced to 3 percent with the following results indicating acceptable wash/wear, crease and shrinkage properties.
  • polyester resin (7) 0.10 percent alkylaryl polyether alcohol (Triton X- 155) 20.0 percent glyoxal resin 1) 5.00 percent fast curing acylic emulsion (3) 5.00 percent polyester resin (7) I 3.00 quaternary ammonium softener (5) 3.00 percent zinc chloride catalyst solution, 50% in water 3.00 percent ammonium chloride solution, 25% in water 0.5 percent boric acid
  • the polyester resin (7) was Aerotex Resin DHB (American Cyanamid), described as a 57 percent active, self-emulsifying cross-linkable polyester resin in xylene, used for durable hand building.
  • a further embodiment of the invention contemplates the use of catalyst combinations which will permit the application of the desired durable press effects at even lower pressing temperatures than those indicated above. It is possible, for example, by using an aqueous solution comprising zinc chloride and 1-6 percent citric acid as the catalyst to so lower the temperature at which a durable press can be imparted (e.g., 260300 F. for 10-30 seconds) that the durable press can be accomplished at home using a hand steam iron or a hot flat iron.
  • the use of a solution of 1-6 percent citric acid and, for example, zinc chloride or the like in conventional amounts (e.g., from 1 to 6 percent) makes it possible to reduce the effective pressing or curing temperature of the system by from 20-30F.
  • citric acid also tends to reduce the amount of total shrinkage in the processed fabric (i.e., heat shrinkage and washed shrinkage). in other words, the citric acid seems to stabilize the fabric without the need to sanforize.
  • the citric acid and zinc chloride or other catalyst somehow coact to initiate partial reaction with one or more of the resinous components of the finish during the initial drying operation, after application of the finish to bring about the desired results although the actual mechanism is not understood.
  • EXAMPLE 5 A formulation was prepared as in Example 1 using the following components in the indicated amounts:
  • EXAMPLE 7 The following formulations were prepared in warm water by adding the components in the order listed.
  • Formula I Formula ll 0.10% 0.10% alkylaryl polyether alcohol (Triton X- l 55) 0.50% 0.50% nonylphenoxypoly(ethyleneoxy )ethanol (lgepal CO-897) 20.00% 20.00% glyoxal resin (l 7.50% 7.50% fast curing acrylic emulsion (3) 7.50% 7.50% self crosslinking acrylic emulsion 3.00% 3.00% high density polyethylene, 29% aqueous emulsion (Aqualene 6.00% 3.00% zinc chloride solution, 60% in water 300% citric acid solution, 40% in water Two light weight fabrics (50/50 polyester/cotton blend and a white 100 percent cotton) were treated with the above formulas.
  • Triton X- l 55 0.50% 0.50% nonylphenoxypoly(ethyleneoxy )ethanol (lgepal CO-897) 20.00% 20.00% glyoxal resin (l 7.50% 7.50% fast curing acrylic emulsion (3) 7.50% 7.50%
  • a process for providing a durable press on a cellulosic textile garment or other article which comprises applying to cellulosic textile fabric a finish comprising an aqueous mixture of, on a weight basis, 3-25 percent of a thermosetting durable press textile reactant, 3-20 percent of at least one low temperature crosslinking acrylic polymer, and 0.1-7 percent of a crosslinking catalyst, drying, cutting said fabric into pieces and sewing the same together into said garment or article and pressing the resulting article in the desired shape and simultaneously curing the finish so as to obtain said durable press, the pressing and curing being carried out at a temperature not in excess of about 345F.

Landscapes

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

Abstract

Disclosed herein is a process for producing a durable press cellulosic textile fabric comprising to the fabric applying an aqueous mixture of a thermosetting durable press textile reactant, and a crosslinking acrylic polymer, a crosslinking catalyst, making the fabric into a garment or article and subsequently pressing and curing said mixture on the article.

Description

Unite States Patent Barber et a1.
[ 1 May 8, 1973 PROCESS FOR PRODUCING DURABLE PRESS TEXTILES Inventors: Richard P. Barber; Glen R. Moses, both of Mooresville, N.C.
Assignee: Burlington Industries, Inc., Greensboro, N.C.
Filed: June 11, 1971 Appl. No.: 152,428
US. Cl. ..38/144, 8/116.3, 8/115.6,
117/11,117/139.4,117/143 A, 117/161 UT Int. Cl. ..D06m 13/54, D06rn 13/40 Field of Search ..117/139.4, 139.5 A,
117/143 A, 11, 161 UT, 10;8/l15.6, 116.3; 260/851,856;38/144 References Cited UNITED STATES PATENTS 5/1969 Emmons ..117/142 X 2,950,553 8/1960 Hurwitz ..117/143 A 3,220,869 ll/l965 Ruemens et al. ..l17/139.4 X 3,096,524 7/1963 Mizell .,l 17/139.4 X
2,623,031 12/1952 Snyder r ..260/75 P 3,186,954 6/1965 Hushebeck... "1117/1394 X 3,159,562 11/1964 Kine et al. ..161/170 Primary ExaminerWilliam D. Martin Assistant Examiner-Theodore G. Davis Attorney-Cushman, Darby & Cushman [57] ABSTRACT 8 Claims, N0 Drawings =t LE PRESS The preparation of durable press textiles comprising cellulosic fibers, e.g., knitted or woven fabric made up of blends of cotton and polyester, is now well known. Procedures for preparing such textiles involve applying an aqueous composition containing a durable press reactant to cellulosic fabric, drying, pressing and curing. When a durable press garment is to be made, the dried fabric is usually cut and sewn into the desired form, e.g., pants, and then pressed and cured. Pressing and curing may be carried out simultaneously at relatively high temperatures (see U. S. Pat. No. 2,950,553) although the more widely practiced technique is to press the garment at a somewhat lower temperature (such as 300335F.) using, for example, a hot head press, followed by a separate baking or curing operation in an oven at higher temperatures (e.g., 350375 F.).
A number of variations in the above procedures, or alternatives thereto, are also known in the art. For example, U. S. Pat. No. 3,341,955 describes the preparation of durable press garments from 100 percent cotton fabrics by padding the fabric with an aqueous durable press reactant finish, drying and curing. Thereafter, when a garment with a permanent crease is to be made, the area where the crease is desired is treated with acid catalyst and pressed at high temperature (350F. or above).
A further alternative is also described in US. Pat. No. 3,341,955 for use when the fabric comprises a blend of cotton and thermoplastic fibers, such as polyester. In that embodiment, the fabric, after application of the durable press finish, and drying, is formed into a garment and pressed, sufficient heat being applied during pressing to soften and set the thermoplastic component in the desired shape. Temperatures in the order of 350 to 500F., depending on the softening point of the thermoplastic fibers, are utilized for the press-setting operation.
While the above procedures give useful durable press effects, several disadvantages are also presented thereby. For example, oven baking a fabric composed entirely of cotton causes a significant deterioration of the cotton with resultant loss in such physical properties as tensile strength, tear strength and abrasion resistance. Blending of the cotton with polyester or the like brings about some improvement in physical properties but the cellulosic component in such blends is still undesirably degraded. This degradation shows up in a number of ways, eg by reduced abrasion resistance, and is especially noticeable after washing cotton/polyester durable press fabrics, the degraded cotton being washed out, along with hand builders or softeners attached thereto, so that the fabric becomes sleezy or thin.
The procedures which involve oven baking also have economic disadvantages, not only in the cost and maintenance of the ovens, but in the relatively long time required (-15 minutes) to accomplish the desired cure. The curing time also has an undesirable effect on fabric color, e.g., hue or cast may be changed and/or whites may be caused to yellow. The simultaneous press/cure procedures are generally free from these problems but they suffer from other disadvantages and,
in general, do not give as good a durable press effect as the procedures involving oven curing.
The principal object of the present invention is to provide durable press textiles and procedures for making the same whereby the above-noted problems with prior procedures are eliminated or substantially reduced. A further object is to provide cellulosic fabrics which have, in addition to an outstanding durable press, other improved physical and aesthetic properties.
Still another object of the invention is to provide a process for obtaining durable press effects on cellulosic textiles using less severe press/cure conditions than previously utilized, with resultant improvement in the overall properties of the product. A more specific object is to provide a durable press finish and process whereby pressing and curing may be effectively carried out simultaneously on the press using lower temperatures and shorter times than normally considered feasible.
Broadly stated, the objects of the invention are realized by treating the fabric with an aqueous formulation of one or more low temperature crosslinking film-forming acrylic polymers, a durable press thermosetting fiber-reactive resin and a curing or cross-linking agent; drying, pressing and curing, the fabric being formed into a garment or other article (e.g., sheets) before the pressing and curing. Preferably a mixture of crosslinking acrylic polymers is used and/or the formulation includes a heat curable or crosslinking elastomer hand builder as described below.
As noted earlier herein, an advantage of the invention is that pressing and curing can be carried out simultaneously using relatively moderate times and temperatures with resultant improvement in the properties of the treated fabric. For example, fabric processed according to the invention can be presscured on a hot head press at temperatures not exceeding 345F., typically in the range of 300F. to 345F. and in some instances even lower (280-290F.) using normal pressing times such as 15 seconds (usually 5 seconds steam, 5 seconds vacuum and 5 seconds dry) to give highly durable'creases and wash and wear properties in the pressed fabric. Additionally, aesthetic properties such as hand, feel and color and physical characteristics, e.g., tensile strength, tear and abrasion resistance, are not undesirably affected.
The success of the invention is due, at least in large measure, to the use of the low temperature crosslinking acrylic polymer in combination with the durable press fiber reactant and curing agent. It is not understood how or why the indicated components function to give the stated results but it is apparent, in any event, that this combination must be used to obtain the overall results of the invention. It appears that the indicated components somehow work together in a synergistic fashion to give the results indicated since durable press properties, for example, exceed those which would be expected from the normal additive effect of the individual components.
The acrylic polymer used herein may be defined as a copolymer of a lower alkyl ester of acrylic acid or methacrylic acid, or like monoethyleneically unsaturated compound, with another monomer eopolymerizable therewith and additionally including where R is an alkenyl group having 3 to 9 carbon atoms and a terminal group of the formula HzC;C Miami- R is H, CH Ol-l, or Cl-l OR" wherein R is the hydrocarbon residue of a saturated alcohol R"OH having one to eight carbon atoms, R is H, CH OH, or CH OR" R is H, CH OH, or CH OR", and R is H, CH OH, or Cl-l OR", and 2. from 99.5 to 0.5 percent by weight of one or more monomers selected from acrylic acid, methacrylic acid, the nitriles thereof, the esters thereof with a saturated aliphatic alcohol having one to 18 carbon atoms, acrylamide, methacrylamide, the N-methylol derivatives of these amides, itaconic acid, vinyl acetate, vinyl chloride, styrene, and o-, m-, and p-vinyltoluene.
' Copolymers of this type are described in U. S. Pat. No.
i of comonomers (2). Such polymers may have molecular weights in the order of 1,000 to I ,O00,000 and are available in latex or emulsion form. A particularly preferred low temperature crosslinking acrylic copolymer for use herein is the product of Example of U.S. Pat. No. 3,446,777 but using butyl acrylate instead of the ethyl acrylate referred to therein (i.e. the copolymer of butyl acrylate and methylolated-4-pentenoguanamine) with the pH modified from 5.4 to 9.0 by addition of ammonia to improve emulsion stability. Similar copolymers of methylolated-4-pentenoguanamine with, for example, ethyl acrylate or other lower alkyl acrylates, may also be used.
It is particularly advantageous to utilize a mixture of two different low temperature crosslinking acrylic polymers for present purposes and an especially useful embodiment of the invention contemplates using a mixture of the low temperature crosslinking acrylic copolymer of a lower alkyl acrylate and methylolated- 4-pentenoguanamine as described above together with the water insoluble, water-dispersible low temperature self-crosslinking acrylic copolymers of a lower alkyl acrylate (e.g., ethyl or butyl acrylate) and an N- methylolacrylamide as described in U.S. Pat. No. 3,157,562, e.g., the copolymer of 90-99 percent lower alkyl acrylate, l-lO percent N-methylolacrylamide and optionally from 0-3 percent acrylamide.
According to the invention it is also advantageous to include in the durable press formulation a curable elastomer or like hand builder. The elastomer component, if used, is most desirably a heat curable polyester elastomer hand builder although other elastomers may be used. The term elastomer as used herein has the meaning given by The American Society for Testing Materials as described in the Encyclopedia of Chemical Technology, 2nd Edition, Volume 7, page 676. This is a material that is capable of recovery from large deformations quickly and forcibly and can be modified to a state in which it is essentially insoluble (but can swell) in boiling solvents such as benzene, methyl ethyl ketone and the ethanol-toluene azeotrope. A rubber in its modified state, free of diluents, retracts within one minute to less than 1.5 times its original length after being stretched at room temperature (2027before release.
A wide variety of elastomers may be used for present purposes, although they are primarily grouped into several recognized categories. As indicated, the preferred category comprises the polyester elastomers including Paraplex rubbers (see Industrial and Engineering Chemistry, Volume 39, page 1090 (1947), Norepal polyester rubbers derived from ethylene glycol and dimeric soya beam fatty acids, copolymer of terephthalic acid and acyclic dicarboxylic acid and a glycol (see U.S. Pat. Nos. 2,623,033 and 2,623,031), all polyesters linked together by diisocyanates., for example, polyethylene adipate linked by 1,5-naphthalene diisocyanate (see Polyesters and their Applications," by Bjorksten et al., 1956, page 226). These are related to polyurethane elastomers which are cross-linked by diisocyanates.
Other heat-curable elastomers which may be used herein, in lieu of or in addition to a polyester elastomer, include, for example, acrylic elastomers, olefin polymers and the homopolymers and copolymers of dienes such as butadiene, isoprene and chloroprene. The acrylic elastomers are addition type polymers and copolymers which contain a predominant amount of an acrylic acid ester with an alcohol having two or more carbon atoms such as ethyl acrylate or butyl acrylate. These may be crosslinked through the hydrogen atom adjacent the carboxyl group of the acrylic acid moiety by means of a peroxide or by including a small amount (e.g., about 5 percent) of functional groups such as olefinic groups, halogen, carboxyl and cyano.
The olefin elastomers include ethylene-propylene rubber and butyl rubber. Ethylene-propylene rubber typically contains 40-70 percent ethylene, the balance being propylene. Butyl rubber typically comprises 0.5-2.5 percent molar isoprene, balance isobutene. Polyvinyl alcohol, polyvinyl acetate and the like may also be included in the formulation along with conventional types of softeners, surfactants, etc.
As the durable press reactant component of the present finish, any of the conventional durable press, reactant resins may be used. Typically, the resin is a water-soluble precondensate of formaldehyde with such amino compounds as urea, thiourea, cyclic ethylene ureas (e.g., dimethylol cyclic ethylene urea or dimethylol dihydroxy cyclic ethylene urea), melamine, ethyl carbamate, urons, triazones and triazines or mixtures thereof. Blocked isocyanates may also be effectively used.
Suitable crosslinking or curing catalysts for use herein include, without being limited thereto, magnesium chloride or nitrate or zinc chloride or nitrate; various amine hydrochlorides such as 2-amino-2-methyl-lpropanol hydrochloride, or triethanol-amine hydrochloride; and ammonium salts such as ammonium chloride, tartrate, citrate, formate, oxalate, nitrate or ammonium ethyl phosphate or ammonium dihydrogen phosphate or the like. These catalysts may be combined, e.g., zinc nitrate and ammonium chloride may be used together, and/or catalyst modifiers may be included as necessary to achieve desired effects, e.g., to increase or decrease catalyst activity. It is particularly useful to employ citric acid in conjunction with zinc chloride, or other catalyst since the citric acid makes it possible to effectively utilize even lower pressing temperatures, e.g., 280F., as described later herein.
It may also be helpful in some cases to include additives such as boric acid, the latter being useful to avoid any tendency of the pressed fabric to yellow in the event of an after-curing operation.
Typically, the finish of the invention will comprise, on a weight basis, from 3-20 percent of the low temperature cross-linking acrylic polymer or mixtures thereof, -15 percent, preferably 5-10 percent heat curable elastomer; 3-25 percent durable press resin; and 0.1-7 percent catalyst, balance water. Additionally, the finish may include from O to 5 percent (usually 0.2-2 percent) surfactant, and from O-lO percent of other conventional durable press components such as extenders, softeners or the like.
The finish is applied to the fabric in any convenient fashion, e.g., by dipping or spraying but preferably by padding. The amount of the finish applied can be widely varied and is dependent on such factors as the nature and construction of the fabric, its intended use, etc. Usually, however, wet pickup will fall in the range of 30-75 percent by weight of the fabric. The thus-treated fabric is then dried, usually at l90-220F. for 1-5 minutes, to a moisture content in the order of 5-l 0 percent by weight.
The dried fabric is then cut into the desired shape, sewn into a garment or other article and pressed on a hot head press or the equivalent. Typical pressing conditions comprise pressing on the hot head press at 300345F. for up to seconds or so. Curing or baking in an oven is not necessary since, with the finish of the invention, durable press effects are obtained by pressing only. However, if desired, the pressed article may be baked under proper conditions without serious disadvantages. If, as in some cases, it is desired to produce an excellent wash and wear fabric, then fabrics treated with this finish can be precured or cured in the finishing plant at 280-345F. for 30 to 180 seconds.
The invention is illustrated, but not limited, by the following examples wherein percentages are by weight unlessotherwise indicated:
EXAMPLE 1 The following formulation was prepared in warm water (e.g., 8 O-l00F.) by adding the components in the order listed to sufficient water to give the indicated percent concentration.
0.10 percent alkylaryl polyester alcohol (Triton 5.00 percent glyoxal resin l 5.00 percent polyester resin (2) 5.00 percent fast curing acrylic emulsion (3) 3.00 percent acrylic ester emulsion (4) 3.00 percent cationic quaternary ammonium softener (5) 3.00 percent zinc chloride solution, 50% in water The above components l (5) may be more fully defined as follows:
Component (1): N,N-dimethylol dihydroxyethylene urea, 50 percent solution in water;
Component (2): a polyester of phthalic anhydride, polyethylene glycol and glycerides of hydrogenated fatty acids (commercially available as Discol 716);
Component (3): the product of Example 10 of US. Pat. No. 3,446,777 with the substitution of butyl acrylate for the ethyl acrylate used in Example 10 and with adjustment of the pH of the emulsion to 9 by addition of ammonia to stabilize the emulsion;
Component (4): an aqueous emulsion of /25 ethyl acrylate/vinyl acetate copolymer, solids content 40 percent (commercially available as Wicaset P.E.P.);
Component (5): crude dimethyldistearylammonium hydrogen sulfate, the stearyl groups being predominant in a mixture of higher alkyl radicals derived from hydrogenated tallow.
The following fabrics (A) (D) were padded through the above formulation followed by drying for 1% minutes at 300F.
A few days later the above fabrics were pressed on a hot head press for 5 seconds steam, 5 seconds vacuum, 5 seconds dry at 345F. and pounds air (9,000 psi in head). The thus pressed fabrics were then home laundered five times with tumble drying after each laundering. The laundered fabrics were then checked for wash/wear and crease appearance and evaluated using a grade rating of from l-5, values of l-3 being considered unacceptable and 5 representing the optimum. The results obtained are shown below.
Wash/Wear Crease Fabric Appearance Appearance (A) Polyester/cotton (50/50) 3.6 5.0 (B) Polyester/cotton (50/50) 4.0 5.0 (C) Polyester/cotton (50/50) 4.3 5.0 (D) Polyester/rayon (SO/50) 4.6 5.0
As will be evident, specimens (A) (D) demonstrated effective durable press and wash/wear properties notwithstanding the fact that the specimens were only pressed on the hot head press to obtain these properties. The laundered specimens were also characterized by outstanding physical and aesthetic properties, e.g., abrasion resistance, tensile and tear strength, hand, feel and the like.
EXAMPLE 2 Example 1 was repeated except that the formulation was changed to include 20 percent of the glyoxal resin (1), rather than 5 percent; and the polyester resin (2) and acrylic ester emulsion (4) were replaced by 5 percent self-crosslinking acrylic emulsion (6), namely, an aqueous emulsion of a copolymer of butyl acrylate and an N -methylolacrylamide per US. Pat. No. 3,157,562.
Three fabrics (E, F and G) of the same construction as used in Example 1 were processed in similar fashion with the thus modified formulation and evaluated for wash/ wear appearance, crease appearance and total shrinkage with the following results:
Wash/Wear Crease Total Fabric Appearance Appearance Shrinkage (E) Polyester/cotton (SO/50) 4.0 5.0 1.94 X 1.39 (F) Polyester/cotton (50/50) 4.0 5.0 2.67 X 1.19 (G) Polyester/cotton (SO/50) 3.6 5.0 2.58 X 1.11
The indicated wash/wear, crease and shrinkage values are satisfactorily within acceptable limits for these properties.
EXAMPLE 3 Example 2 was repeated except that the amount of zinc chloride catalyst was increased to 6 percent and the amount of selfcrosslinking acrylic emulsion was reduced to 3 percent with the following results indicating acceptable wash/wear, crease and shrinkage properties.
Wash/Wear Crease Total Fabric Appearance Appearance Shrinkage Polyester/cotton (50/50) 4.0 5.0 2.50 X .92 Polyester/cotton (50/50) 4.3 5.0 2.02 X .36 Polyester/cotton EXAMPLE 4 Example 1 was repeated using the following aqueous formulation:
0.10 percent alkylaryl polyether alcohol (Triton X- 155) 20.0 percent glyoxal resin 1) 5.00 percent fast curing acylic emulsion (3) 5.00 percent polyester resin (7) I 3.00 quaternary ammonium softener (5) 3.00 percent zinc chloride catalyst solution, 50% in water 3.00 percent ammonium chloride solution, 25% in water 0.5 percent boric acid The polyester resin (7) was Aerotex Resin DHB (American Cyanamid), described as a 57 percent active, self-emulsifying cross-linkable polyester resin in xylene, used for durable hand building.
The following results were obtained in fabric specimens as indicated:
Tensile Wash/Wear Crease Fabric Strength Appearance Appearance lbs. Polyester/cotton (50/50) 117 X 86 4.3 5.0 Polyester/cotton (50/50) 101 X 73 4.0 5.0 100% cotton 67 X 57 4.0 4.0
A further embodiment of the invention contemplates the use of catalyst combinations which will permit the application of the desired durable press effects at even lower pressing temperatures than those indicated above. It is possible, for example, by using an aqueous solution comprising zinc chloride and 1-6 percent citric acid as the catalyst to so lower the temperature at which a durable press can be imparted (e.g., 260300 F. for 10-30 seconds) that the durable press can be accomplished at home using a hand steam iron or a hot flat iron. In other words, the use of a solution of 1-6 percent citric acid and, for example, zinc chloride or the like in conventional amounts (e.g., from 1 to 6 percent) makes it possible to reduce the effective pressing or curing temperature of the system by from 20-30F. using press times in the order of 10-30 seconds, advantageously 15-20 seconds. The presence of the citric acid also tends to reduce the amount of total shrinkage in the processed fabric (i.e., heat shrinkage and washed shrinkage). in other words, the citric acid seems to stabilize the fabric without the need to sanforize. Apparently the citric acid and zinc chloride or other catalyst somehow coact to initiate partial reaction with one or more of the resinous components of the finish during the initial drying operation, after application of the finish to bring about the desired results although the actual mechanism is not understood.
The advantages of using citric acid in the catalyst system are shown by the following additional examples:
EXAMPLE 5 A formulation was prepared as in Example 1 using the following components in the indicated amounts:
0.10 percent alkylaryl polyester alcohol (Triton X-l55) 0.50 percent nonylphenoxypoly(ethyleneoxy)etha nol (Igepal CO-897) 20.00 percent glyoxal resin l) 7.50 percent fast curing acrylic emulsion (3) 7.50 percent self crosslinking acrylic emulsion (6) 2.00 percent tall oil ester softener 6.00 percent zinc chloride solution, 50 percent in water 6.00 percent citric acid solution, 40 percent in water Polyester/cotton (50/50) fabrics as in Example 1 were padded through the above formulation, dried at 300F. for 1% minutes and subsequently pressed. One set of fabrics was pressed on the hot head press at 325F. for 15 seconds, another set was pressed at 290F. for 15 seconds, with the following crease values and wash/wear results, after five home launderings.
Pressed at 325F. Pressed at 290F.
15 seconds 15 seconds Fabric Weight Wash/Wear Wash/Wear OIs/SqXd. Crease Appearance Crease Appearance EXAMPLE 6 Example 5 was repeated except that the amount of citric acid used was reduced to 4 percent and the.
fabrics tested were as shown below with the following results:
Pressed at 290F. 15 seconds Crease Wash/ Total Fabric Fabric Appear- Wear Shrinkage Weight Blend ance Appea.r (Heat/ ance Wash) "w 6.30 Polyester/rayon 5.0 4.6 1.83 x
6.0 Polyester/cotton The above results show that the exemplified process, using citric acid as a catalyst component, gives outstanding crease and wash/wear properties and dimensional stability using lower than normal pressing temperatures.
EXAMPLE 7 The following formulations were prepared in warm water by adding the components in the order listed.
Formula I Formula ll 0.10% 0.10% alkylaryl polyether alcohol (Triton X- l 55) 0.50% 0.50% nonylphenoxypoly(ethyleneoxy )ethanol (lgepal CO-897) 20.00% 20.00% glyoxal resin (l 7.50% 7.50% fast curing acrylic emulsion (3) 7.50% 7.50% self crosslinking acrylic emulsion 3.00% 3.00% high density polyethylene, 29% aqueous emulsion (Aqualene 6.00% 3.00% zinc chloride solution, 60% in water 300% citric acid solution, 40% in water Two light weight fabrics (50/50 polyester/cotton blend and a white 100 percent cotton) were treated with the above formulas. Wet pickup was 65-75 percent, fabrics dried for 1% minutes at 300F. Pant legs were made and were creased and pressed with a hand steam iron for approximately 30 seconds on each side. The following data show wash/wear and crease appearance after five home launderings and the tensile strength and abrasion properties.
Hand Steam Iron Hand Steam Iron 100% Cotton 50/50 Polyester/Cotton Formula Formula Formula Formula I ll 1 ll Tensile-Warp 54 55 62 6| (Pounds) Filling 50 50 39 46 Crease Appearance 5.0 5.0 5.0 5.0 Wash/Wear Appearance 4.0 4.0 4.0 4.0 Abrasion 429 492 2000+ 2000+ Untreated Tensile-Warp 65 65 65 65 (Pounds) 4 Filling 59 59 38 38 EXAMPLE 8 Approximately 18,000 yards of a /50 polyester/cotton fabric were treated by padding the above formula, tenter drying followed by running the fabric over the palmer unit of a sanforizer.
Several samples were taken throughout the run. Pant legs were made and pressed for 15 seconds at 280F. with 70 pounds of air on pressing head.
The following data is the average of these several sample representing l8,000 yards.
Fabric Weight Tensile Crease Wash/Wear %Shrinkage O1s./Sq.Yd. (Grab Appear- Appear- Stabilization lbs.) ance" ance" 7.42 I74 X 109 5.0 4.3 2.l5 X 0.73
"as measured after 5 home launderings EXAMPLE 9 The following formulation was prepared in warm water by adding the components in the order listed.
0.10 percent alkylaryl polyether alcohol (Triton X- 1 0.50 percent nony1phenoxypoly(ethyleneoxy)etha nol (lgepal CQ-897) 20.00 percent glyoxal resin l 7.50 percent fast curing acrylic emulsion (3) 7.50 percent self crosslinking acrylic emulsion (6) 2.00 percent tall oil ester softener 6.00 percent zinc chloride solution, percent in water citric acid solution, 40 percent in water *varying amounts of citric acid as below The fabric used was a 50/50 polyester/cotton blend. Fabric specimens were pressed at 290F. for 15 seconds. Washed five times.
Crease Wash/Wear Appear- Appear- Experiment Citric Acid ance ance No. l 0.0 5.0 4.0 No. 2 L0 5.0 5.0 No. 3 2.0 5.0 5.0 No. 4 3.0 5 .0 5.0
As can be seen from the above data acceptable crease and wash and wear appearance were obtained with and without the use of citric acid by pressing the treated fabric at 280F. although wash and wear appearance was maximized with the addition of 1 percent or more of citric acid.
It will be appreciated that various modifications may be made in the invention described herein. Hence the scope of the invention is defined in the following claims wherein:
We claim:
1. A process for providing a durable press on a cellulosic textile garment or other article which comprises applying to cellulosic textile fabric a finish comprising an aqueous mixture of, on a weight basis, 3-25 percent of a thermosetting durable press textile reactant, 3-20 percent of at least one low temperature crosslinking acrylic polymer, and 0.1-7 percent of a crosslinking catalyst, drying, cutting said fabric into pieces and sewing the same together into said garment or article and pressing the resulting article in the desired shape and simultaneously curing the finish so as to obtain said durable press, the pressing and curing being carried out at a temperature not in excess of about 345F.
6. The process of claim 2 wherein a mixture of crosslinking acrylic polymers is used comprising the copolymer of a lower alkyl acrylate and methylolated- 4-pentenoguanamine and the copolymer of a lower alkyl acrylate and an N-methylolacrylamide.
7. The process of claim 2 wherein the mixture also includes a film-forming heat curable elastomer.
8. The process of claim 7 wherein the elastomer is a polyester elastomer.

Claims (8)

1. A process for providing a durable press on a cellulosic textile garment or other article which comprises applying to cellulosic textile fabric a finish comprising an aqueous mixture of, on a weight basis, 3-25 percent of a thermosetting durable press textile reactant, 3-20 percent of at least one low temperature crosslinking acrylic polymer, and 0.1-7 percent of a crosslinking catalyst, drying, cutting said fabric into pieces and sewing the same together into said garment or article and pressing the resulting article in the desired shape and simultaneously curing the finish so as to obtain said durable press, the pressing and curing being carried out at a temperature not in excess of about 345*F.
2. The process of claim 1 wherein the cross-linking acrylic polymer comprises the copolymer of a lower alkyl acrylate and methylolated-4-pentenoguanamine.
3. The process of claim 1 wherein the pressed and cured textile article is subsequently further cured.
4. The process of claim 1 wherein the catalyst is a mixture of zinc chloride and citric acid and the textile is pressed at 260*-280*F.
5. A durable press textile article obtained by the process of claim 1.
6. The process of claim 2 wherein a mixture of crosslinking acrylic polymers is used comprising the copolymer of a lower alkyl acrylate and methylolated-4-pentenoguanamine and the copolymer of a lower alkyl acrylate and an N-methylolacrylamide.
7. The process of claim 2 wherein the mixture also includes a film-forming heat curable elastomer.
8. The process of claim 7 wherein the elastomer is a polyester elastomer.
US00152428A 1971-06-11 1971-06-11 Process for producing durable press textiles Expired - Lifetime US3731411A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US15242871A 1971-06-11 1971-06-11

Publications (1)

Publication Number Publication Date
US3731411A true US3731411A (en) 1973-05-08

Family

ID=22542875

Family Applications (1)

Application Number Title Priority Date Filing Date
US00152428A Expired - Lifetime US3731411A (en) 1971-06-11 1971-06-11 Process for producing durable press textiles

Country Status (1)

Country Link
US (1) US3731411A (en)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3962493A (en) * 1972-01-26 1976-06-08 Uniroyal Inc. Method of making an ironer roll cover
US3979532A (en) * 1971-04-30 1976-09-07 Statni Vyzkumny Ustav Kozedelny Process for the manufacture of artificial leather and product made thereby
US4358501A (en) * 1978-08-14 1982-11-09 Ppg Industries, Inc. Storage stable polyolefin compatible size for fiber glass strands
EP0163124A2 (en) * 1984-04-30 1985-12-04 The B.F. GOODRICH Company Improved fabric coating composition with low formaldehyde evolution
EP0651088A1 (en) * 1993-10-22 1995-05-03 Rohm And Haas Company Method for strengthening cellulosic substrates
US5496476A (en) * 1992-12-21 1996-03-05 Ppg Indutstries, Inc. Non-formaldehyde durable press finishing for cellulosic textiles with phosphonoalkylpolycarboxylic acid
US5614591A (en) * 1994-12-15 1997-03-25 The Virkler Company Process and composition for imparting durable press properties to textile fabrics
US5755828A (en) * 1996-12-18 1998-05-26 Weyerhaeuser Company Method and composition for increasing the strength of compositions containing high-bulk fibers
US5998511A (en) * 1994-03-25 1999-12-07 Weyerhaeuser Company Polymeric polycarboxylic acid crosslinked cellulosic fibers
US6022329A (en) * 1993-04-19 2000-02-08 Stryker Corporation Irrigation handpiece with built in pulsing pump
US6184271B1 (en) 1994-03-25 2001-02-06 Weyerhaeuser Company Absorbent composite containing polymaleic acid crosslinked cellulosic fibers
US6375685B2 (en) * 1997-05-13 2002-04-23 The Procter & Gamble Company Textile finishing process
US20020160675A1 (en) * 1999-09-10 2002-10-31 Nano-Tex, Llc Durable finishes for textiles
US6508844B1 (en) * 1997-05-20 2003-01-21 Commonwealth Scientific And Industrial Method for improving the stability of the shape of trousers
US6565612B2 (en) 1998-09-30 2003-05-20 The Procter & Gamble Company Shrink resistant rayon fabrics
US6623445B1 (en) 1993-12-30 2003-09-23 Stryker Corporation Surgical suction irrigator
US6746419B1 (en) 1993-04-19 2004-06-08 Stryker Corporation Irrigation handpiece with built in pulsing pump
US20180313000A1 (en) * 2016-03-24 2018-11-01 Lg Chem, Ltd. Preparation method of superabsorbent polymer fiber

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2623031A (en) * 1950-03-20 1952-12-23 Du Pont Elastic linear copolyesters
US2950553A (en) * 1957-01-16 1960-08-30 Rohm & Haas Method of producing wrinkle resistant garments and other manufactured articles of cotton-containing fabrics
US3096524A (en) * 1961-04-11 1963-07-09 Williamson Dickie Mfg Company Process for improving crease-retention properties of cotton garments
US3159562A (en) * 1961-09-07 1964-12-01 Exxon Research Engineering Co Integrated process for effectively recovering oil from tar sands
US3186954A (en) * 1958-09-24 1965-06-01 Bancroft & Sons Co J Catalyst system for heat curing of fabrics
US3220869A (en) * 1959-03-13 1965-11-30 Basf Ag Process for improving textile fabrics
US3446777A (en) * 1965-05-13 1969-05-27 Rohm & Haas Non-conjugated polymerizable alkenylguanamines,polymers thereof,and methods of making them

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2623031A (en) * 1950-03-20 1952-12-23 Du Pont Elastic linear copolyesters
US2950553A (en) * 1957-01-16 1960-08-30 Rohm & Haas Method of producing wrinkle resistant garments and other manufactured articles of cotton-containing fabrics
US3186954A (en) * 1958-09-24 1965-06-01 Bancroft & Sons Co J Catalyst system for heat curing of fabrics
US3220869A (en) * 1959-03-13 1965-11-30 Basf Ag Process for improving textile fabrics
US3096524A (en) * 1961-04-11 1963-07-09 Williamson Dickie Mfg Company Process for improving crease-retention properties of cotton garments
US3159562A (en) * 1961-09-07 1964-12-01 Exxon Research Engineering Co Integrated process for effectively recovering oil from tar sands
US3446777A (en) * 1965-05-13 1969-05-27 Rohm & Haas Non-conjugated polymerizable alkenylguanamines,polymers thereof,and methods of making them

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3979532A (en) * 1971-04-30 1976-09-07 Statni Vyzkumny Ustav Kozedelny Process for the manufacture of artificial leather and product made thereby
US3962493A (en) * 1972-01-26 1976-06-08 Uniroyal Inc. Method of making an ironer roll cover
US4358501A (en) * 1978-08-14 1982-11-09 Ppg Industries, Inc. Storage stable polyolefin compatible size for fiber glass strands
EP0163124A2 (en) * 1984-04-30 1985-12-04 The B.F. GOODRICH Company Improved fabric coating composition with low formaldehyde evolution
EP0163124A3 (en) * 1984-04-30 1987-05-13 The B.F. Goodrich Company Improved fabric coating composition with low formaldehyde evolution
US5705475A (en) * 1992-12-21 1998-01-06 Ppg Industries, Inc. Non-formaldehyde durable press finishing for cellulosic textiles with phosphonoalkylpolycarboxylic
US5496476A (en) * 1992-12-21 1996-03-05 Ppg Indutstries, Inc. Non-formaldehyde durable press finishing for cellulosic textiles with phosphonoalkylpolycarboxylic acid
US20070149918A1 (en) * 1993-04-19 2007-06-28 Arnett Jeffery D Medical/surgical irrigator with a tip through which irrigation fluid is discharged and a suction is drawn, a variable rate pulse pump for discharging the irrigation fluid and a seperate battery pack for powering the pump
US6746419B1 (en) 1993-04-19 2004-06-08 Stryker Corporation Irrigation handpiece with built in pulsing pump
US20040210186A1 (en) * 1993-04-19 2004-10-21 Stryker Corporation. Irrigation handpiece with built in pulsing pump
US6022329A (en) * 1993-04-19 2000-02-08 Stryker Corporation Irrigation handpiece with built in pulsing pump
US7144383B2 (en) 1993-04-19 2006-12-05 Stryker Corporation Surgical/medical irrigating handpiece with variable speed pump, integrated suction and battery pack
EP0651088A1 (en) * 1993-10-22 1995-05-03 Rohm And Haas Company Method for strengthening cellulosic substrates
US20050075600A1 (en) * 1993-12-30 2005-04-07 Stryker Corporation Surgical suction irrigator
US7297133B2 (en) 1993-12-30 2007-11-20 Stryker Corporation Surgical suction irrigator
US6623445B1 (en) 1993-12-30 2003-09-23 Stryker Corporation Surgical suction irrigator
US6184271B1 (en) 1994-03-25 2001-02-06 Weyerhaeuser Company Absorbent composite containing polymaleic acid crosslinked cellulosic fibers
US5998511A (en) * 1994-03-25 1999-12-07 Weyerhaeuser Company Polymeric polycarboxylic acid crosslinked cellulosic fibers
US6620865B2 (en) 1994-03-25 2003-09-16 Weyerhaeuser Company Polycarboxylic acid crosslinked cellulosic fibers
US5614591A (en) * 1994-12-15 1997-03-25 The Virkler Company Process and composition for imparting durable press properties to textile fabrics
US5755828A (en) * 1996-12-18 1998-05-26 Weyerhaeuser Company Method and composition for increasing the strength of compositions containing high-bulk fibers
US6719809B2 (en) 1997-05-13 2004-04-13 The Procter & Gamble Company Textile finishing process
US6716255B2 (en) 1997-05-13 2004-04-06 The Procter & Gamble Company Textile finishing process
US6827746B2 (en) 1997-05-13 2004-12-07 Strike Investments, Llc Textile finishing process
US6375685B2 (en) * 1997-05-13 2002-04-23 The Procter & Gamble Company Textile finishing process
US6508844B1 (en) * 1997-05-20 2003-01-21 Commonwealth Scientific And Industrial Method for improving the stability of the shape of trousers
US6565612B2 (en) 1998-09-30 2003-05-20 The Procter & Gamble Company Shrink resistant rayon fabrics
US6872424B2 (en) 1999-09-10 2005-03-29 Nano-Tex, Llc Durable finishes for textiles
US20020160675A1 (en) * 1999-09-10 2002-10-31 Nano-Tex, Llc Durable finishes for textiles
US20180313000A1 (en) * 2016-03-24 2018-11-01 Lg Chem, Ltd. Preparation method of superabsorbent polymer fiber
US10760184B2 (en) * 2016-03-24 2020-09-01 Lg Chem, Ltd. Preparation method of superabsorbent polymer fiber

Similar Documents

Publication Publication Date Title
US3731411A (en) Process for producing durable press textiles
US3649165A (en) Soil-release characteristics of textile materials
US3157562A (en) Bonded non-woven fibrous products and methods of making them
US3666400A (en) Sizing of yarns and fibers with combinations of polymers and crosslinking agents
US4090844A (en) Process of producing high performance durable-press cotton
US2690404A (en) Method of making wrinkle resistant fabric and composition therefor
US3220869A (en) Process for improving textile fabrics
US3540835A (en) Carboxylic acid group containing copolymer is applied to textile which has been treated with an aminoplast resin to improve soil release characteristics thereof
US3597145A (en) Treatment of a cellulosic-containing textile with a fluorocarbon,an aminoplast,and a synthetic acid copolymer,and textile obtained therefrom
AU642465B2 (en) Flame retardant composition and method of use
US3096524A (en) Process for improving crease-retention properties of cotton garments
US3811131A (en) Durable press process for treating cellulosic material with methylolamides and acetic acid or formic acid vapors
US3521993A (en) Soil releasing textiles
US3012911A (en) Bonded non-woven fibrous products and methods of producing them
US3598641A (en) Process for improving the oil release and anti-static properties of a textile and the resulting product
USRE28914E (en) Treatment of a cellulosic-containing textile with a fluorocarbon, an aminoplast, and a synthetic acid copolymer, and textile obtained therefrom
US3428480A (en) Flame-retardant cellulosic material,composition and method for making same
US3245831A (en) Process of finishing textiles with mechanically stable latex of emulsified particles of emulsion-polymerized nonoxidized polyethylene
US3837799A (en) Process for creaseproofing cellulosic fiber-containing fabric using formaldehyde vapor and a solid and a solid catalyst
US3632422A (en) Textile fabric having soil release finish and method of making same
US3674548A (en) Process for imparting soil-releasing and anti soil-redeposition properties to textile materials
US3219478A (en) Flameproofing of cellulosic material
US2780608A (en) Protein-containing textiles and stabilization thereof
US3617188A (en) Soil release fabrics and method for producing same
US3526474A (en) Abrasion-resistant durably-pressed cellulosic textiles

Legal Events

Date Code Title Description
AS Assignment

Owner name: BI/MS HOLDINGS I INC., A DE. CORP.

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:BURLINGTON INDUSTRIES, INC.,;REEL/FRAME:004811/0598

Effective date: 19870903