US3175987A - Aqueous epoxy resin compsition yielding anti-static soil resistant finish on textiles - Google Patents

Aqueous epoxy resin compsition yielding anti-static soil resistant finish on textiles Download PDF

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Publication number
US3175987A
US3175987A US120906A US12090661A US3175987A US 3175987 A US3175987 A US 3175987A US 120906 A US120906 A US 120906A US 12090661 A US12090661 A US 12090661A US 3175987 A US3175987 A US 3175987A
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US
United States
Prior art keywords
parts
textiles
epoxy resin
polyepoxide
aqueous epoxy
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
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US120906A
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English (en)
Inventor
Pretka John Edward
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EIDP Inc
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EI Du Pont de Nemours and Co
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Publication date
Priority to BE619144D priority Critical patent/BE619144A/xx
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to US120906A priority patent/US3175987A/en
Application granted granted Critical
Publication of US3175987A publication Critical patent/US3175987A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • D06M15/55—Epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S260/00—Chemistry of carbon compounds
    • Y10S260/15—Antistatic agents not otherwise provided for
    • Y10S260/17—High polymeric, resinous, antistatic agents
    • 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S524/00—Synthetic resins or natural rubbers -- part of the class 520 series
    • Y10S524/91—Antistatic compositions
    • Y10S524/911—Composition to apply to a substrate to be destaticized

Definitions

  • composition of matter comprising an aqueous dispersion containing from about 1% to about total solids of which from about 30% to about 65% is a member of the class consisting of sodium polyacrylate, maleic anhydride, phthalic anhydride and pyromellitic anhydride, the remainder of the said solids being a mixture of polyepox-ide and polyamine of the formula wherein -R- is a divalentradical, -X is a member of the class consisting of amino nitrogen and divalent radical terminating inamino nitrogen, m and n are small whole numbers from about 3 to about 40 and p is an integer no greater than about 10.
  • -R-- Since the nature of -R-- is not critical provided it is inert to reaction with amines, it may be any member of the class consisting of while it may contain aza linkages is otherwise hydrocarbon, q being a number from about 6 to about 40.
  • the preparation of these polyamines is discussed in detail in Belgian p-atents'55'4,506, granted January 25, 11957, and 560,446, granted September 14, 1957.
  • the polyethylene glycol dih-alide e.g. chloride, bromide or iodide
  • analogue is condensed (with release of hydrogen halide) with an amine, the nitrogen of which contains at least two active hydrogen.
  • Typical of such amines are methylamine, ethylamine, propylamine, butylamine,
  • Suitable polyepoxides can be prepared by condensing e-pichlorohydrin with a polyol.
  • a typical example is the condensation product (with elimination of HCl) of glycerine and epichlorohydrin. Preparation of these products is described in detail in British patent 780,288, dated July 31, 1957.
  • Such a material with a molecular weight of between about 280 to 360 is available on the open market under the trademark Eponite 100.
  • Epon resins which are diepoxide condensation products ofepichlorohydrin and dimethyl, d-i-para hydroxyphenyl methane and the polyallyl glycidyl ethers).
  • a typical siloxane is 1,3-bis- [-3(2,3 epoxy propoxy)p-ropyl] tetrame-thyldisiloxane sold under the trademark Syl-Kem 90.
  • Reaction of the poly-amine (l) or (II) with the polyepoxide may be conveniently accomplished by heating the shaped structure to which an acidic mixture of the amine and polyepoxide has been applied.
  • the treated fabrics are scoured in a bath containing 0.5% by weight-base on the solution of the sodium salt of an unsaturated long chain alcohol sulfate and 0.5 by weight based on the solution of trisodium hexametaphosphate.
  • the dry cleaning operation involves a 25-minute tumble at room temperature using a solution of the following:
  • the effectiveness of the static treatment on rugs is measured by the Galvonometer Runway Test.
  • Rug samples at 20% relative humidity and F., measuring 2 x 10 feet are used.
  • the subject wearing shoes with clean and dry leather soles and rubber heels, discharges himself completely to ground.
  • he walks a definite number (eighteen) of normal steps on the carpet, and then grasps a probe that connects him through a galvanometer toground.
  • the galvanometer deflection gives a relative comparison of static electricity.
  • a galvanometer of 25 ohms resistance shunted with a 60 ohm resistor static becomes barely evident at 25 deflection units.
  • static tendency is comparable to a cotton rug.
  • EXAMPLE 1 208 parts of the polyethylene glycol polyamine formed by the condensation of methyl amine and polyethylene glycol 600 dichloride as a 20% solids solution in water is stirred into 1540 parts of Water. 24.6 parts of the polyepoxide prepared from glycerin and epichlorohydrin as described in detail in British Patent 780,288, dated July 21, 1957 and identified therein as Polyether A with an epoxy equivalency of 2.13, and having a molecular weight of 324 and 240 parts of a 25% aqueous solution of polyacrylic acid are then added and the mixture dispersed using a Waring Blendor. The pH is adjusted to 6.1 with aqueous solution of sodium hydroxide.
  • a 7.5 x 40" piece of 24 oz./yd. 66 nylon i.e.
  • polyhexamethylene adipamide) rug is dipped into the mixture described above, squeezed between the rollers of a hand wringer and dried at 212 F. for 30 to 45 minutes in a forced airoven. Curing of the amine epoxide resin occurs during the drying stage. The dried rug is observed to have gained 7.4% by weight of antistatic antisoiling finish based on the original weight of the rug. After the rug is scoured for minutes at 120 F. and dried at 212 F., rubber latex is applied to the backing to give 16 oz./yd. solids. The structure is then dried and cured by heating for 30' minutes at 212 F.
  • mixtures are prepared using polybasic organic anhydrides. 208 parts of the same polyethylene glycol polyamine is stirred into 1780 parts of water. 24.6 parts of the same polyepoxide is mixed in and the pH of the solution is then adjusted to 5.5 with 10% acetic acid. 30 parts of anhydride are added and the mixture dispersed using a Waring Blendor. Phthalic anhydride, maleic anhydride and pyromellitic dianhydride are used in the preparation of the mixtures. The mixtures containing the anhydrides are then used to treat 66 nylon rugs as described above and the dried rug samples are observed to have gained 6.07.0% by weight.
  • EXAMPLE 2 15 parts of the polyethylene glycol polyamine solution of Example 1, 1.5 parts of the polyepoxide of Example 1, 18 parts of the polyacrylic acid solution of Example 1 and 65.5 parts of water are placed in a stainless steel container and thoroughly mixed. The pH is adjusted to 7.0 with dilute sodium hydroxide solution. -This mixture is then padded onto a 3' x of 24 oz./yd. 66 nylon rug using a Butterworth padder set for 10 y.p.m. and squeezed between the nip of two rollers set at 25 p.s.i. The rug is dried at 250 F, beck scoured for V minutes at 120 F., rinsed thoroughly, dried at 250 F.
  • Example 1 The treated rug is then used in the Galvanometer Runway Test and found to register 25 deflection units while an untreated 66 nylon rug showed more than 50 deflection units.
  • EXAMPLE 3 50.0 parts of the polyethylene glycol polyamine of Example 1, 5.0 parts of the polyepoxide of Example 1 and 635 parts of Water are mixed thoroughly, the pH ad-,
  • the log R values of the fabrics so treated, PA and N are then measured.
  • the treated fabrics are then subjected to the ry-cleaning procedure and the log R values are again determined. Not only do the treated and cleaned fabrics show retained surface resistance, but also they do not show the discoloration and stiffening of similar samples prepared without the addition of sodium polyacrylate, PA and N
  • the log R values of the treated fabrics and of untreated controls, PA and N are summarized in Table II.
  • the fabric is heated at 285 F. for 5 minutes to dry the fabric and cure the resin, scoured 30 minutes at F., rinsed and dried.
  • the fabric is observed to have gained 3.5% by weight of antistatic antisoiling agent based on the original weight of the fabric.
  • the treated fabric has a log R of 11.4 before dry clearing. After dry cleaning its log R is 11.7 and it shows little or no discoloration.
  • a similarly prepared fabric containing only the amine-epoxide resin has a log R of 10.4 before dry cleaning and, after dry cleaning, has a log R of 13.2 It is highly discolored.
  • the treating mixtures of this invention are prepared by dispersing the, ingredients in water at room temperature with vigorous stirring. Although the concentration may vary, dilute mixtures containing from about 1 to about 10% of ingredients are generally preferred. Any such finishing suspension having a concentration suitable to provide from about a 1 to about a 10% solids pickup based on the dry material is satisfactory.
  • the product can be applied to the fabric by conventional methods such as dipping, padding, spraying, and the like.
  • the proportion of components may vary over a wide range.
  • the proportion of polyamine:polyepoxide is maintained within the limits of :1 to 1:4 With the polyanionic polymer or the polybasic organic anhydride making up from about 30% to about 65% of the total weight of the applied solids.
  • Optimum conditions of drying and curing will depend upon the identity of the reactants and the identity of the textile. Generally, however, a temperature of at least about 240 F. is preferred to accomplish efficient drying of the textile. Usually, temperature adjustment is made to permit drying and curing of fabrics in a 3 to 45 minute interval. A temperature of about 212 F. to 300 F. is recommended for most textile materials.
  • a composition of matter comprising an aqueous dispersion containing from about 1% to about 10% total solids of which from about 30% to about 65 is a member of the class consisting of sodium polyacrylate, maleic anhydride, phthalic anhydride and pyromellitic anhydride, the remainder comprising a mixture in proportions between about 4:1 and 1:10 of a polyepoxide and a polyamine of the formula:
  • --R- is a divalent radical
  • X- is a member of the class consisting of amino nitrogen and divalent radical terminating in amino nitrogen
  • m and n are small whole numbers from about 3 to about and p is an integer no greater than about 10.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US120906A 1961-06-30 1961-06-30 Aqueous epoxy resin compsition yielding anti-static soil resistant finish on textiles Expired - Lifetime US3175987A (en)

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Application Number Priority Date Filing Date Title
BE619144D BE619144A (is") 1961-06-30
US120906A US3175987A (en) 1961-06-30 1961-06-30 Aqueous epoxy resin compsition yielding anti-static soil resistant finish on textiles

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3335105A (en) * 1964-07-06 1967-08-08 Monsanto Co Antistatic composition comprising the reaction product of a polyepoxide, a polyamine, and a nitrogen containing compound
US3441427A (en) * 1966-02-07 1969-04-29 Customark Corp Method of producing opaque shadow mark
US3907737A (en) * 1972-03-04 1975-09-23 Basf Ag Metal coating composition of water insoluble binder and water soluble thickener
FR2325706A1 (fr) * 1975-09-24 1977-04-22 Basf Wyandotte Corp Procede pour ameliorer les proprietes antistatiques d'une matiere polymere
EP0435497A1 (en) * 1989-12-26 1991-07-03 Texaco Chemical Company Trifunctional polyoxyethylene diamine derivatives
EP0301706A3 (en) * 1987-07-27 1991-07-17 Texaco Development Corporation Aromatic amidoamines

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE554506A (is") * 1956-01-25
BE560446A (is") * 1957-06-17 1957-09-14
US2872427A (en) * 1954-10-04 1959-02-03 Shell Dev Polyepoxide emulsions and method of treating textiles therewith
US2872428A (en) * 1955-01-31 1959-02-03 Shell Dev Polyepoxide emulsions and method of treating textiles therewith

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2872427A (en) * 1954-10-04 1959-02-03 Shell Dev Polyepoxide emulsions and method of treating textiles therewith
US2872428A (en) * 1955-01-31 1959-02-03 Shell Dev Polyepoxide emulsions and method of treating textiles therewith
BE554506A (is") * 1956-01-25
BE560446A (is") * 1957-06-17 1957-09-14
US3070552A (en) * 1957-06-17 1962-12-25 Onyx Oil & Chemical Company Polyamines

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3335105A (en) * 1964-07-06 1967-08-08 Monsanto Co Antistatic composition comprising the reaction product of a polyepoxide, a polyamine, and a nitrogen containing compound
US3441427A (en) * 1966-02-07 1969-04-29 Customark Corp Method of producing opaque shadow mark
US3907737A (en) * 1972-03-04 1975-09-23 Basf Ag Metal coating composition of water insoluble binder and water soluble thickener
FR2325706A1 (fr) * 1975-09-24 1977-04-22 Basf Wyandotte Corp Procede pour ameliorer les proprietes antistatiques d'une matiere polymere
EP0301706A3 (en) * 1987-07-27 1991-07-17 Texaco Development Corporation Aromatic amidoamines
EP0435497A1 (en) * 1989-12-26 1991-07-03 Texaco Chemical Company Trifunctional polyoxyethylene diamine derivatives

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Publication number Publication date
BE619144A (is")

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