US3242117A - Composition and process for producing polyester textile materials having water repellent and antistatic properties - Google Patents

Composition and process for producing polyester textile materials having water repellent and antistatic properties Download PDF

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US3242117A
US3242117A US31453963A US3242117A US 3242117 A US3242117 A US 3242117A US 31453963 A US31453963 A US 31453963A US 3242117 A US3242117 A US 3242117A
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water
polyester
repellent
antistatic
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Cohen Sidney
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Millmaster Onyx Corp
Millmaster Onyx Group Inc
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Assigned to BARCLAYS AMERICAN, 1 BUSINESS CREDIT, INC. reassignment BARCLAYS AMERICAN, 1 BUSINESS CREDIT, INC. SECURITY INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MILLMASTER ONYX GROUP, INC., A DE CORP.
Assigned to MILLMASTER ONYX GROUP, INC., A DE CORP. reassignment MILLMASTER ONYX GROUP, INC., A DE CORP. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: KEWANEE INDUSTRIES, INC.
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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
    • D06M15/19—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
    • D06M15/277—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof containing fluorine
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/372—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
    • 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
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
    • 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]
    • Y10T428/3154—Of fluorinated addition polymer from unsaturated monomers
    • Y10T428/31544—Addition polymer is perhalogenated

Definitions

  • Polyester textile fibers and fabrics are synthetic materials having widespread use in the manufacture of consumer garments and industrial fabrics.
  • the physical properties of polyester fibers such as Dacron of E. I. du Pont de Nemours and Company, Fortrel of the Celanese Corporation, Kodel of Eastman Corporation and Vycron of Beaunit Mills, Inc., have many advantages over those of natural or regenerated cellulosic or protein fibers and transmit these advantages to fabrics manufactured from them.
  • polyester fibers and fabrics suffer from a serious disadvantage. Being hydrophobic in nature, that is, having a low tendency to absorb moisture, they have the undesirable property of accumulating electrostatic charges developed by friction during processing of the fabric and during normal industrial or consumer use of the articles manufactured from them.
  • the curing agents which have been successfully used and described in the above-mentioned patents are polyhalides or polyepoxides.
  • An example of a polyhalide catalyst is the polyethylene glycol diiodide (sold by Onyx Chemical Corp.) under the name Aston Catalyst.
  • An example of a satisfactory polyepoxide catalyst is Eponite 100 (sold by Shell Chemical Corp.). It is a di-epoxide having the formula:
  • a second method used to reduce the static accumula tion properties of polyester fabrics is to prepare fabrics from blends of the hydrophobic polyester fiber and hydrophyllic cellulosic fibers such as cotton and rayon.
  • Such blended polyester-cellulosic fabrics containing up to 50% cellulosic fiber content are now sold on the market and are extensively used in the manufacture of textile products such as suits, dresses, shirts, etc.
  • the process of this invention comprises the impregnation of a polyester or polyester-cellulosic blended fabric with an aqueous composition containing the following:
  • the cationic polyethoxy-containing polymeric electrolytes suitable for the practice of this invention are those mentioned above. Their structure may vary over a wide range, but they consist essentially in polymeric materials having a positive charge and containing a plurality of ethoxy and amino groups. They may be represented by the general formula:
  • R is the residue of a primary monoamine after the removal of the primary NH group
  • R is an organic divalent radical
  • n are average numbers between 3 and 40
  • p is an integer greater than '1
  • X is the ester forming residue of an inorganic acid or of an organically substituted sulfuric, phosphoric, and sulfonic acid such as Cl, Br, I, CH SO OSOgH, and the like.
  • the water-repellent silicon resins suitable for the practice of this invention consist of mixtures of poly (dimethyl siloxanes) and poly (methyl hydrogen siloxanes) described in Moil'liet, Water-Proofing and Water Re pellency, Elsevier Publishing Co., New York, pp. 153- (1963).
  • Such water-repellent silicone resins such as Sylmer 1108 (sold by Dow Corning Corp.) are marketed as aqueous emulsions under a variety of trade names.
  • water-repellent emulsions examples include: Repelotex HE a 30% active water-repellent silicone resin emulsion (sold by Onyx Chemical Corp.), Hydro Pruf (sold by Arkansas Co.) and Norane Silicone (sold by Warwick Chemical Division, Sun Chemical Co.).
  • emulsions of water-repellent silicone polymers are used together with an appropriate organometallic catalyst which serves to insolubilize the silicone polymer on heating.
  • Appropriate catalysts include zinc, tin and zirconium salts of organic naphthenic and fatty acids having 8 to 18 carbon atoms and are supplied as emulsions or pastes dispersible in water and compatible with the silicone water-repellent emulsions.
  • Repelofix 7 S asold by Onyx Chemical Corp.
  • Coblefix asold by Arkansas Co.
  • Catalyst 47 sold by Dow Corning Corp.
  • fiuorochemical waterand oil-repellent compounds suitable as a component of the composition of this invention are polymers of perfluoroalkyl acrylates and perfluoroalkyl methacrylates or copolymers of same, marketed under the trade name Scotchguard by Minnesota Mining & Mfg. Co. described in Patent 3,102,103 and also in volume 32, Textile Research Journal, pages 320- 331 (1962).
  • the polyaziridinyl compounds necessary for the practice of this invention are organic compounds containing at least two aziridinyl groups and at least one hydrophyllic group capable of conferring water solubility or emulsifiability in water on the molecule, such hydrophyllic group or groups being non-reactive with the aziridinyl group.
  • suitable polyaziridinyl componnds described in my abandoned application Serial No. 268,590 filed March 28, 1963, are tris-l-aziridinyl phosphine oxide and 1,6-bis-(N-ethylenecarbamido)hexane.
  • compositions for the practice of this invention are as follows, the amounts being expressed as percentages by weight of active material present in the aqueous treating bath:
  • the fabric to be treated is passed through the treating bath containing the above ingredients in a padder or similar textile-impregnation equipment, then heated at elevated temperatures on drying cans or in a curing oven.
  • the time and temperature of heating may be varied over wide limits, a preferred range being 1 to 5 minutes at about 250 F. to about 350 F.
  • Antistatic properties were evaluated by the AATCC Electrical Resistivity Method 841960, page B 103 in the above-mentioned manual. Water repellency was considered satisfactory if the spray rating was a minimum of 90 initially and 70 after 5 launderings or dry cleanings. Antistatic proper ties were considered satisfactory if the electrical resistivity after 5 launderings or dry cleanings, expressed as Log R, at 30% relative humidity and 75 F., was less than 13.0. Oil repellency was evaluated by the method described in Scotchguard Technical Bulletin, Appendix A., Minnesota Mining & Mfg. Co. (1959), and considered satisfactory if ratings were 90 minimum.
  • Example 1 An aqueous bath was prepared containing 27% Aston 123 (sold by Onyx Chemical Corp.) (20% active), 2.8% Chemirad APO (sold by Chemirad Corp.) (an 85% alcoholic solution of tris-l-aziridinyl phosphine oxide), 6%
  • Example 2 The process of Example 1 was repeated, except that the curing agent Chemirad APO was replaced by 2% Eponite (sold by Shell Chemical Corp.) mixed with 0.5% Neutronyx 600 (sold by Onyx Chemical Corp.), a condensation product of nonyl phenol with 9.5 moles of ethylene oxide. This sample was designated Sample B.
  • Example 3 An aqueous treating bath was prepared containing 10% Aston 108 (sold by Onyx Chemical Corp.), 1% Chemirad APO and 8.6% Scotchguard PC 208 (28% active) (sold by Minnesota Mining & Mfg. Co.). A small amount of hydrochloric acid was added to reduce the pH value of the solution to 5.0. White Dacron taffeta (Testfabrics, Inc., Style #709) was treated with this solution in a 3-roll padder with the roll pressure adjusted to allow the goods to pick up approximately 25% of its weight of treating solution. The goods Were then framed and heated for 2 minutes at 220 F. and 5 minutes at 300 F. The sample was designated as Sample C.
  • a process for simultaneously imparting antistatic and water-repellent properties to polyester and blended polyester-cellulosic blended fabrics which comprises the steps of impregnating the fabric with an aqueous antistatic composition containing an antistatic agent comprising a water-soluble cationic polyelectrolyte containing ethoxy and amino groups, having the general formula s t H NCH CHKO CH2CH2)mO R20 (CHzCHzO) nCI-I CIIz:
  • R is the residue of a primary monoamine after removal of the primary NH group
  • R is an organic divalent radical
  • n are average numbers between 3 and 40
  • p is an integer greater than 1
  • a polyaziridinyl curing agent for said antistatic agent and a waterrepellent agent selected from the group consisting of (1) an aqueous emulsion of a water-repellent silicone resin together with an organo-metallic catalyst for said silicone resin and (2) a waterand oil-repellent compound selected from the group consisting of polymers of perfluoroalkyl acrylates, perfluoroalkyl methacrylates and copolymers of same, and then drying the treated fabric at temperatures from about 250 F. to about 350 F. for about 1 to about 5 minutes.
  • the water-repellent agent is a water-and-oil repellent compound selected from the group consisting of polymers of perfiuoroalkyl acrylates, perfiuoroalkyl methacrylates and copolymers of same.
  • the impregnating bath is an aqueous composition containing 1.0% to 5.0% antistatic agent, 0.2% to 2.0% curing agent, and 1.0% to 3.0% Water-and-oil repellent compound selected from the group consisting of polymers of perfluoroalkyl acrylates, perfluoroalkyl methacrylates and copolymers of same.
  • a composition for imparting water-repellent and antistatic properties to polyester and blended polyestercellulosic blended materials consisting of an aqueous mixture of a water-soluble polyelectrolyte containing ethoXy and amino groups having the general formula 9 wherein R is the residue of a primary monoamine after removal of the primary NH group, R is an organic divalent radical, in and n are average numbers between 3 and 40, and p is an integer greater than 1, a polyaziridinyl curing agent, and a water-repellent agent selected from the group consisting of (1) water-repellent silicone resins together with organo-metallic catalysts for said silicone resin and (2) a water-and-oil repellent compound selected from the group consisting of polymers of perfluoroalkyl acrylates, perfluoroalkyl methacrylates and copolymers of same.

Description

United States Patent COMPOSITION AND PROCESS FOR PRODUCING POLYESTER TEXTILE MATERIALS HAVING WATER REPELLENT AND ANTISTATIC PRO ERTHES Sidney Cohen, Jersey City, N.J., assignor, by mesne assignments, to Millmaster Onyx Corporation, New York, N.Y., a corporation of New York No Drawing. Filed Oct. 7, 1963, Ser. No. 314,539
9 Claims. (Cl. 26029.2)
Polyester textile fibers and fabrics are synthetic materials having widespread use in the manufacture of consumer garments and industrial fabrics. The physical properties of polyester fibers, such as Dacron of E. I. du Pont de Nemours and Company, Fortrel of the Celanese Corporation, Kodel of Eastman Corporation and Vycron of Beaunit Mills, Inc., have many advantages over those of natural or regenerated cellulosic or protein fibers and transmit these advantages to fabrics manufactured from them. However, polyester fibers and fabrics suffer from a serious disadvantage. Being hydrophobic in nature, that is, having a low tendency to absorb moisture, they have the undesirable property of accumulating electrostatic charges developed by friction during processing of the fabric and during normal industrial or consumer use of the articles manufactured from them.
Two methods have been used in the art toovercome this inherent propensity for polyester to accumulate electrostatic charges. One is the treatment of the fabrics or fibers with durable antistatic chemical agents such as are described in US. Patents 2,882,185, 2,914,427 and 2,982,751. These are cationic polyelectrolytes containing ethoxy and amino groups. These compounds are water-soluble polymers which are applied to polyester fabrics in aqueous solution together with a curing agent. Upon heating at temperatures above 210 F., the curing agents react with the cationic polymer to produce a cross-linked, insoluble film around the polyester fibers. The treated fabrics then possess low electrical resistance, which results in good antistatic properties, and these properties are durable to repeated laundering and dry cleaning. The curing agents which have been successfully used and described in the above-mentioned patents are polyhalides or polyepoxides. An example of a polyhalide catalyst is the polyethylene glycol diiodide (sold by Onyx Chemical Corp.) under the name Aston Catalyst. An example of a satisfactory polyepoxide catalyst is Eponite 100 (sold by Shell Chemical Corp.). It is a di-epoxide having the formula:
A second method used to reduce the static accumula tion properties of polyester fabrics is to prepare fabrics from blends of the hydrophobic polyester fiber and hydrophyllic cellulosic fibers such as cotton and rayon. Such blended polyester-cellulosic fabrics containing up to 50% cellulosic fiber content are now sold on the market and are extensively used in the manufacture of textile products such as suits, dresses, shirts, etc.
'But though it has been possible to produce polyester or blended polyester-cellulosic fabrics with acceptable antistatic properties as outlined above, it has been very difiicult to produce fabrics that possess both antistatic and water-repellent properties. This is to be expected since achievement of Water repellency requires the modification of the fibers or fiber surfaces to make them extremely hydrophobic and such hydrophobic fibers, having high electrical resistivity, will have poor antistatic properties. Conversely, treatment of the fibers with the durable antistatic agents mentioned above will produce a surface containing ethoxy groups and ionic groups, both of which are hydrophyllic and tend to make such a surface easily wettable by water.
It is therefore an object of this invention to provide a novel process for finishing polyester and polyestercellulosic blended fabrics to impart simultaneous waterrepellent and antistatic properties to them.
It is a further object of this invention to provide a composition and process for finishing polyester and polyester-cellulosic blended fabrics to impart water-repellent and antistatic properties which are durable to repeated launderings and. dry cleanings.
It is a further object of this invention to provide a polyester or polyester-cellulosic blended textile material which exhibits durable water-repellent and antistatic properties without aifecting the physical and aesthetic properties of the fabric such as whiteness, handle and tensile strength.
Other objects and advantages of the invention will become apparent from the following description.
The process of this invention comprises the impregnation of a polyester or polyester-cellulosic blended fabric with an aqueous composition containing the following:
(a) A cationic, polyethoxy-containing polymeric electrolyte (b) A polyaziridinyl curing agent (0) A water-repellent silicone resin or fluorochemical oiland water-repellent compound,
then heating the fabric at temperatures above 220 F.
The cationic polyethoxy-containing polymeric electrolytes suitable for the practice of this invention are those mentioned above. Their structure may vary over a wide range, but they consist essentially in polymeric materials having a positive charge and containing a plurality of ethoxy and amino groups. They may be represented by the general formula:
wherein R is the residue of a primary monoamine after the removal of the primary NH group, R is an organic divalent radical, in and n are average numbers between 3 and 40, p is an integer greater than '1, and wherein X is the ester forming residue of an inorganic acid or of an organically substituted sulfuric, phosphoric, and sulfonic acid such as Cl, Br, I, CH SO OSOgH, and the like. The preparation of these polytertiary amines is fully described in US. Patent 3,070,552, issued December 25, 1962.
The water-repellent silicon resins suitable for the practice of this invention consist of mixtures of poly (dimethyl siloxanes) and poly (methyl hydrogen siloxanes) described in Moil'liet, Water-Proofing and Water Re pellency, Elsevier Publishing Co., New York, pp. 153- (1963). Such water-repellent silicone resins, such as Sylmer 1108 (sold by Dow Corning Corp.) are marketed as aqueous emulsions under a variety of trade names. Examples of such water-repellent emulsions are: Repelotex HE a 30% active water-repellent silicone resin emulsion (sold by Onyx Chemical Corp.), Hydro Pruf (sold by Arkansas Co.) and Norane Silicone (sold by Warwick Chemical Division, Sun Chemical Co.). These emulsions of water-repellent silicone polymers are used together with an appropriate organometallic catalyst which serves to insolubilize the silicone polymer on heating. Appropriate catalysts include zinc, tin and zirconium salts of organic naphthenic and fatty acids having 8 to 18 carbon atoms and are supplied as emulsions or pastes dispersible in water and compatible with the silicone water-repellent emulsions. Examples of such catalysts are: Repelofix 7 S (sold by Onyx Chemical Corp.), Coblefix (sold by Arkansas Co.) and Catalyst 47 (sold by Dow Corning Corp.).
The fiuorochemical waterand oil-repellent compounds suitable as a component of the composition of this invention are polymers of perfluoroalkyl acrylates and perfluoroalkyl methacrylates or copolymers of same, marketed under the trade name Scotchguard by Minnesota Mining & Mfg. Co. described in Patent 3,102,103 and also in volume 32, Textile Research Journal, pages 320- 331 (1962).
The polyaziridinyl compounds necessary for the practice of this invention are organic compounds containing at least two aziridinyl groups and at least one hydrophyllic group capable of conferring water solubility or emulsifiability in water on the molecule, such hydrophyllic group or groups being non-reactive with the aziridinyl group. Examples of suitable polyaziridinyl componnds, described in my abandoned application Serial No. 268,590 filed March 28, 1963, are tris-l-aziridinyl phosphine oxide and 1,6-bis-(N-ethylenecarbamido)hexane.
The quantities of each ingredient used in the treating bath may vary over wide limits, depending upon the particular fabric to be treated and on the degree of antistatic and water-repellent properties required by the end-use of the treated fabric. Preferred ranges of composition for the practice of this invention are as follows, the amounts being expressed as percentages by weight of active material present in the aqueous treating bath:
(a). 1.0 to 5.0% of antistatic agent (b) 0.2 to 2.0% of polyaziridinyl curing agent 1.0 to 3.0% of silicone polymer together with 0.3 to 1.5% of silicone curing catalyst, or 1.0 to 3.0% of fluorochemical compound.
The fabric to be treated is passed through the treating bath containing the above ingredients in a padder or similar textile-impregnation equipment, then heated at elevated temperatures on drying cans or in a curing oven. The time and temperature of heating may be varied over wide limits, a preferred range being 1 to 5 minutes at about 250 F. to about 350 F.
.This invention will be further described by the following examples which are presented as illustrative and are not to be considered as limiting the practice of the invention. In the examples described below, launderings were carried out in a Westinghouse commercial Laundromat using Tide (sold by Procter and Gamble Co.) detergent and the hot (140 F.) setting with a five-pound load, followed by ironing on a flatbed press. Dry cleaning was carried out by tumbling the fabric in Stoddard solvent at room temperature for 1 hour, followed by air drying. Water repellency was evaluated by AATCC Spray Test Method 22-1961, Technical Manual of the American Association of Textile Chemists and Colorists, volume XXXVIII, page B 119. Antistatic properties were evaluated by the AATCC Electrical Resistivity Method 841960, page B 103 in the above-mentioned manual. Water repellency was considered satisfactory if the spray rating was a minimum of 90 initially and 70 after 5 launderings or dry cleanings. Antistatic proper ties were considered satisfactory if the electrical resistivity after 5 launderings or dry cleanings, expressed as Log R, at 30% relative humidity and 75 F., was less than 13.0. Oil repellency Was evaluated by the method described in Scotchguard Technical Bulletin, Appendix A., Minnesota Mining & Mfg. Co. (1959), and considered satisfactory if ratings were 90 minimum.
Example 1 An aqueous bath was prepared containing 27% Aston 123 (sold by Onyx Chemical Corp.) (20% active), 2.8% Chemirad APO (sold by Chemirad Corp.) (an 85% alcoholic solution of tris-l-aziridinyl phosphine oxide), 6%
4- Repelotex HE (sold by Onyx Chemical Corp.) (a 30% active water-repellent silicone emulsion) and 2% Repelofix 7 S (sold by Onyx Chemical Corp.) as curing agent for the silicone emulsion. A white poplin fabric con sisting of 65% Dacron polyester fiber and 35% cotton (Testfabrics, Inc., Style #7402) was passed through this aqueous solution in a 3-roll padder, using a roll pressure which allowed the fabric to pick up approximately 50% of its own weight of treating solution. The fabric was then framed and heated 2 minutes at 220 F., then 5 minutes at 300 F. in an electric circulating-air oven. The sample was designated as Sample A and its properties are tabulated in Table 1.
Example 2 The process of Example 1 was repeated, except that the curing agent Chemirad APO was replaced by 2% Eponite (sold by Shell Chemical Corp.) mixed with 0.5% Neutronyx 600 (sold by Onyx Chemical Corp.), a condensation product of nonyl phenol with 9.5 moles of ethylene oxide. This sample was designated Sample B.
Example 3 An aqueous treating bath was prepared containing 10% Aston 108 (sold by Onyx Chemical Corp.), 1% Chemirad APO and 8.6% Scotchguard PC 208 (28% active) (sold by Minnesota Mining & Mfg. Co.). A small amount of hydrochloric acid was added to reduce the pH value of the solution to 5.0. White Dacron taffeta (Testfabrics, Inc., Style #709) was treated with this solution in a 3-roll padder with the roll pressure adjusted to allow the goods to pick up approximately 25% of its weight of treating solution. The goods Were then framed and heated for 2 minutes at 220 F. and 5 minutes at 300 F. The sample was designated as Sample C.
Example 4 TAB LE I S ample Spray Rating Spray Rating after 5 Launderings.
Spray Rating after 5 Dry Cleanings.
Log R Log B after 5 Launderings.
Log R alter 5 Dry Cleanings Oil Repellency Oil Repellency after 5 Launderings.
Oil Repellency after 5 Dry cleanings. Handle S0ft Slightly Solt Slightly Firm Firm Yellowing None None None Marked.
The data tabulated above clearly demonstrate that the novel compositions of this invention and the finishing process described impart simultaneous durable waterrepellent and antistatic properties to polyester and blended polyester-cellulosic fabrics. Furthermore, the data show that the novel use of polyaziridinyl curing agents in the compositions of this invention permit the achievement of the desirable water-repellent and antistatic properties without impairing the aesthetically important properties of soft handle and whiteness, an achievement which has not been possible with processes heretofore known to the art which utilize polyhalide or polyepoxide curing agents.
I claim:
1. A process for simultaneously imparting antistatic and water-repellent properties to polyester and blended polyester-cellulosic blended fabrics which comprises the steps of impregnating the fabric with an aqueous antistatic composition containing an antistatic agent comprising a water-soluble cationic polyelectrolyte containing ethoxy and amino groups, having the general formula s t H NCH CHKO CH2CH2)mO R20 (CHzCHzO) nCI-I CIIz:|NH
wherein R is the residue of a primary monoamine after removal of the primary NH group, R is an organic divalent radical, in and n are average numbers between 3 and 40, and p is an integer greater than 1, a polyaziridinyl curing agent for said antistatic agent, and a waterrepellent agent selected from the group consisting of (1) an aqueous emulsion of a water-repellent silicone resin together with an organo-metallic catalyst for said silicone resin and (2) a waterand oil-repellent compound selected from the group consisting of polymers of perfluoroalkyl acrylates, perfluoroalkyl methacrylates and copolymers of same, and then drying the treated fabric at temperatures from about 250 F. to about 350 F. for about 1 to about 5 minutes.
2. The process of claim 1 in which the antistatic curing agent is tris-(1-aziridinyl) phosphine oxide.
3. The process of claim 1 in which the curing agent is 1, 6-bis- N-ethylenecarbamido) hexane.
4. The process of claim 2 in which the water-repellent agent is a water-repellent silicone resin.
5. The process of claim 2 in which the water-repellent agent is a water-and-oil repellent compound selected from the group consisting of polymers of perfiuoroalkyl acrylates, perfiuoroalkyl methacrylates and copolymers of same.
6. The process of claim 1 in which the impregnating bath is an aqueous composition containing 1.0% to 5.0%
7. The process of claim 1 in which the impregnating bath is an aqueous composition containing 1.0% to 5.0% antistatic agent, 0.2% to 2.0% curing agent, and 1.0% to 3.0% Water-and-oil repellent compound selected from the group consisting of polymers of perfluoroalkyl acrylates, perfluoroalkyl methacrylates and copolymers of same.
8. A composition for imparting water-repellent and antistatic properties to polyester and blended polyestercellulosic blended materials consisting of an aqueous mixture of a water-soluble polyelectrolyte containing ethoXy and amino groups having the general formula 9 wherein R is the residue of a primary monoamine after removal of the primary NH group, R is an organic divalent radical, in and n are average numbers between 3 and 40, and p is an integer greater than 1, a polyaziridinyl curing agent, and a water-repellent agent selected from the group consisting of (1) water-repellent silicone resins together with organo-metallic catalysts for said silicone resin and (2) a water-and-oil repellent compound selected from the group consisting of polymers of perfluoroalkyl acrylates, perfluoroalkyl methacrylates and copolymers of same.
9. Polyester and blended polyester-cellulosic fabrics treated by the process of claim 1.
References Cited by the Examiner UNITED STATES PATENTS 2,901,444 8/1959 Chance et al 26079 2,982,751 5/1961 Anthes 26029.2 3,070,552 12/1962 Tesoro et a1 2602 3,102,103 8/1963 Ahlbrecht 26029.6
MURRAY TILLMAN, Primary Examiner.
SAMUEL H. BLECH, Examiner.

Claims (1)

1. A PROCESS FOR SIMULTANEOUSLY IMPARTING ANTISTATIC AND WATER-REPELLENT PROPERTIES TO POLYESTER AND BLENDED POLYESTER-CELLULOSIC BLENDED FABRICS WHICH COMPRISES THE STEPS OF IMPREGNATING THE FABRIC WITH AN AQUEOUS ANTISTATIC COMPOSITION CONTAINING AN ANTISTATIC AGENE COMPRISING A WATER-SOLUBLE CATIONIC POLYELECTROLYTE CONTAINING ETHOXY AND AMINO GROUPS, HAVING THE GENERAL FORMULA
US31453963 1963-10-07 1963-10-07 Composition and process for producing polyester textile materials having water repellent and antistatic properties Expired - Lifetime US3242117A (en)

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Cited By (5)

* Cited by examiner, † Cited by third party
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US3442849A (en) * 1965-05-20 1969-05-06 Interpace Corp Epoxy resin composition and process for preparing same
US3503915A (en) * 1966-08-29 1970-03-31 Minnesota Mining & Mfg Fabric treating composition and treated fabric
US3656996A (en) * 1969-04-11 1972-04-18 Agfa Gevaert Nv Antistatic polyester film
JPS5538385B1 (en) * 1971-05-18 1980-10-03
US9534343B2 (en) 2012-10-18 2017-01-03 The Chemours Company Fc, Llc Partially fluorinated copolymer emulsions containing fatty acids and esters

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US2901444A (en) * 1956-06-05 1959-08-25 Leon H Chance Polymers made from 1-aziridinyl phosphine oxides and sulfides and flame resistant organic textiles
US2982751A (en) * 1958-11-17 1961-05-02 Du Pont Process and composition for rendering synthetic hydrophobic material antistatic and the product obtained therefrom
US3070552A (en) * 1957-06-17 1962-12-25 Onyx Oil & Chemical Company Polyamines
US3102103A (en) * 1957-08-09 1963-08-27 Minnesota Mining & Mfg Perfluoroalkyl acrylate polymers and process of producing a latex thereof

Patent Citations (4)

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Publication number Priority date Publication date Assignee Title
US2901444A (en) * 1956-06-05 1959-08-25 Leon H Chance Polymers made from 1-aziridinyl phosphine oxides and sulfides and flame resistant organic textiles
US3070552A (en) * 1957-06-17 1962-12-25 Onyx Oil & Chemical Company Polyamines
US3102103A (en) * 1957-08-09 1963-08-27 Minnesota Mining & Mfg Perfluoroalkyl acrylate polymers and process of producing a latex thereof
US2982751A (en) * 1958-11-17 1961-05-02 Du Pont Process and composition for rendering synthetic hydrophobic material antistatic and the product obtained therefrom

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3442849A (en) * 1965-05-20 1969-05-06 Interpace Corp Epoxy resin composition and process for preparing same
US3503915A (en) * 1966-08-29 1970-03-31 Minnesota Mining & Mfg Fabric treating composition and treated fabric
US3656996A (en) * 1969-04-11 1972-04-18 Agfa Gevaert Nv Antistatic polyester film
JPS5538385B1 (en) * 1971-05-18 1980-10-03
US9534343B2 (en) 2012-10-18 2017-01-03 The Chemours Company Fc, Llc Partially fluorinated copolymer emulsions containing fatty acids and esters

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