WO2002072673A2 - Coating solutions suitable for improving the adhesion of nylon coatings and processes for the application thereof - Google Patents

Coating solutions suitable for improving the adhesion of nylon coatings and processes for the application thereof Download PDF

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Publication number
WO2002072673A2
WO2002072673A2 PCT/US2002/007877 US0207877W WO02072673A2 WO 2002072673 A2 WO2002072673 A2 WO 2002072673A2 US 0207877 W US0207877 W US 0207877W WO 02072673 A2 WO02072673 A2 WO 02072673A2
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Prior art keywords
formaldehyde
weight percent
nylon
coating solutions
coating
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PCT/US2002/007877
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English (en)
French (fr)
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WO2002072673A3 (en
WO2002072673A8 (en
Inventor
Rolando Umali Pagilagan
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EIDP Inc
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EI Du Pont de Nemours and Co
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Priority to KR10-2003-7011862A priority Critical patent/KR20030084979A/ko
Priority to CA002437759A priority patent/CA2437759A1/en
Priority to EP02725170A priority patent/EP1373371B1/en
Priority to JP2002571573A priority patent/JP4163000B2/ja
Priority to AU2002255753A priority patent/AU2002255753A1/en
Priority to DE60226315T priority patent/DE60226315T2/de
Publication of WO2002072673A2 publication Critical patent/WO2002072673A2/en
Publication of WO2002072673A8 publication Critical patent/WO2002072673A8/en
Publication of WO2002072673A3 publication Critical patent/WO2002072673A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00Processes of treating or compounding macromolecular substances
    • C08J3/02Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/09Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00Processes of treating or compounding macromolecular substances
    • C08J3/02Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/09Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
    • C08J3/091Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
    • C08J3/095Oxygen containing compounds
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04Coating
    • C08J7/0427Coating with only one layer of a composition containing a polymer binder
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C08L77/02Polyamides derived from omega-amino carboxylic acids or from lactams thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C08L77/06Polyamides derived from polyamines and polycarboxylic acids
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D177/00Coating compositions based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Coating compositions based on derivatives of such polymers
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D177/00Coating compositions based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D177/02Polyamides derived from omega-amino carboxylic acids or from lactams thereof
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D177/00Coating compositions based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D177/06Polyamides derived from polyamines and polycarboxylic acids
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423Amino-aldehyde resins
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/59Polyamides; Polyimides
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M23/00Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
    • D06M23/10Processes in which the treating agent is dissolved or dispersed in organic solvents; Processes for the recovery of organic solvents thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2377/00Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2477/00Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/20Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/16Synthetic fibres, other than mineral fibres
    • D06M2101/30Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M2101/32Polyesters
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/16Synthetic fibres, other than mineral fibres
    • D06M2101/30Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M2101/34Polyamides
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/50Modified hand or grip properties; Softening compositions
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/31504Composite [nonstructural laminate]
    • Y10T428/31725Of polyamide
    • Y10T428/31728Next to second layer of polyamide
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/31504Composite [nonstructural laminate]
    • Y10T428/31725Of polyamide
    • Y10T428/31728Next to second layer of polyamide
    • Y10T428/31732At least one layer is nylon type
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/31504Composite [nonstructural laminate]
    • Y10T428/31725Of polyamide
    • Y10T428/31736Next to polyester
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/31504Composite [nonstructural laminate]
    • Y10T428/31725Of polyamide
    • Y10T428/31739Nylon type

Definitions

  • FIELD OF THETNVENTION This invention is directed to improving the adhesion of nylon coatings on substrates of nylon and polyester. More specifically this invention is directed to the use of select formaldehyde resins with high imino content or partially alkylated or non-alkylated derivatives thereof to improve the adhesion of mixed nylon polymers to filaments, films, parts and the like made from nylons and polyesters.
  • Nylon “multi-polymers” are nylons made from a mixture of nylon forming monomers such that the nylon polymer contains a mixture of at least two types of nylon structural units. These types of nylons are sold commercially for a variety of coatings and adhesive applications. Generally these nylons are readily soluble in organic solvents and are generally applied as solutions. See for example brochures entitled “Elvamide® Nylon Multipolymer Resins, Properties and Uses” (September 1977) and “Elvamide® Nylon Multipolymer Resins for Thread Bonding” (October 1977), both published by E.I. DuPont de Nemours and Company, Inc.
  • sewing threads are coated with polymeric materials (and with lubricants added in most cases) to protect them from abrasion during the sewing operation. Furthermore, with twisted multi-filament sewing threads the polymeric coatings (also referred to as thread bonding) also prevent fraying and unraveling
  • Nylon multi-polymers have been used for thread bonding applications for several decades. However, there is increasing demand for improved adhesion of the coating to the thread, as for example in highly demanding modern applications. This is also of paramount importance for applications relying upon tightly woven fabric, for example in luggage and automotive air bags, leather, and the like. In such applications abrasion of the thread is high and the operating needle temperature is much higher compared to more loosely woven fabric applications such as those used in apparel.
  • nylon copolymers, terpolymers, and higher multi-polymers are used for coatings applications. These polymers are usually soluble in organic solvents, especially alcohols.
  • the nylon coating is typically applied by dipping the thread in a solution of the nylon multi-polymer and then subsequently passing the thread through a drying chamber and then to a fusing chamber generally at a temperature above the melting point of the nylon mixed polymer. Melting of the nylon multi-polymer coating on the thread promotes adhesion.
  • Nylon mixed polymers are generally favored for this use because of their toughness, good abrasion resistance, and ready solubility in solvents. For more information on these procedures and the benefits associated with nylon mixed polymers, see the Elvamide® (October 1977) brochure and the "Nylon Plastics Handbook" mentioned above.
  • thermosetting resins such as epoxy, phenol-formaldehyde, and melamine-formaldehyde to cross-link nylon multi-polymers and improve the adhesion of the coating.
  • the nylon multi- polymer reacts with these thermosetting resins to form thermoset-thermoplastic compositions.
  • U.S. 4,992,515 describes the use of Cymel® 1135 available from Cytek Industries, Inc., a fully alkylated melamine-formaldehyde resin, and strong acid catalyst to cross-link nylon 6/66/69, nylon 6/66/610, and nylon 6/66/612 terpolymers.
  • the extent of cross-linking achieved was measured by the insolubility in the original solvent of the coating material after cross-linking.
  • the cross-linked nylon coating becomes insoluble in the solvent.
  • no data was provided as to how much improvement in adhesion and resistance to unraveling were achieved.
  • An object of the instant invention is to develop a processing technique and coating solutions to improve the adhesion of nylon coatings to nylons, polyesters, and mixtures thereof. This development applies not only to threads but in general to any substrates where such adhesion is desirable.
  • a further object of the instant invention is to provide such techniques and solutions that are readily adaptable and useful for a variety of applications including monofilaments, multifilaments, films, tubings, shaped parts and the like.
  • a feature of the present invention is the durability of the adhesive bond itself making it suitable for rigorous applications in which the material is extensively handled and manipulated.
  • An advantage of the present invention is that the procedure may utilize any of a variety of solvents.
  • Coating solutions to promote the adhesion of polyamides to substrates of polyamides, polyesters or mixtures thereof are disclosed herein. These solutions comprise:
  • polyamide having a solubility of at least 0.5 weight percent in select organic solvents and (b) 1 to 100 weight percent based on the weight of the polyamide of high imino, partially alkylated or non-alkylated formaldehyde resins selected from the group consisting of melamine-formaldehyde, glycoluril-formaldehyde, benzoguanamine- formaldehyde, and mixtures thereof.
  • 0-20 weight percent based on the weight of the formaldehyde resin of a catalyst may be added .
  • fully alkylated melamine- formaldehyde, glycoluril-formaldehyde, or benzoguanamine-formaldehyde resins may be added.
  • the resins (b) function as adhesion promoters.
  • the resins (b) are preferably incorporated in the range of 1-40 weight percent (most preferably 1-20 weight percent) based on the weight of the polyamide.
  • Nylons suitable as coating materials for purposes of the instant invention are polyamides derived from a lactam containing 6-12 carbon atoms, polyamides derived from 2-12 carbon diamines and 6-12 carbon diacids , polyamides derived from polypropylene glycol diamine or polyethylene glycol diamine and 6-12 carbon atom diacids and mixed polymers of the aforementioned polyamides with the proviso that these polyamides must have a solubility of at least 0.5 weight percent in alcohols, phenols, cresols, or mixtures of these solvents. .
  • the polyamide suitable as coating material is a multi-polymer such as 6/66 copolymer or 6/66/X where X is a polyamide derived from lactam containing 7-12 carbon atoms or polyamide derived from 2-12 carbon diamines and 6-12 carbon diacids.
  • Suitable solvents of the instant invention are methanol, ethanol, 1 -propanol, 2-propanol, 1 -butanol, furfuryl alcohol, benzyl alcohol, phenols, and m-cresols or combinations of these solvents.
  • the selected solvent or combination of solvents may also contain water. Additionally, chlorinated solvents may be added as diluent.
  • the selection of suitable solvent will also depend on several factors as is appreciated by those of skill in the art, such as geometry of the substrate, thickness of the article, and the like.
  • polyamides suitable as substrates herein for mono-filaments, multi-filaments, films, or tubings are those derived from 4-12 carbon diamines and 6-12 carbon diacids, lactams with 6-12 carbon atoms and mixed polymers of the aforementioned monomers.
  • polyesters suitable for mono-filaments, multi-filaments, films, or tubings are polyethylene terephthalate, polypropylene terephthalate, or polybutyleneterephthalate, and their copolymers. It is recognized by those familiar with the art that adhesion and compatibility between polymers are favorable when the two polymers are of the same class or type ie polar polymers will tend to have better adhesion with other polar polymers. Thus, nylon is inherently more adherent to other nylons than to polyesters.
  • the melamine-formaldehyde resins suitable for these inventions are those that contain imino and hydroxymethyl moieties such as Cymel® 325, 1158, 385, 1172, and 1123. These are commercial grades of materials available from Cytek Industries, Inc.
  • the melamine-formaldehyde resins, with or without the catalyst preferably is added to the nylon multi-polymer solution and applied to the substrate as a single solution. However, with comparable effectiveness, the melamine- formaldehyde resins, with or without the catalyst, can be pre-coated to the substrate.
  • Suitable catalysts are inorganic acids such as phosphoric acid, organic acids such as p-toluenesulfonic acid, acetic acid, oxalic acid, and phthalic acid.
  • nylon polymer Materials other than threads such as mono-filaments, tubings, fabrics, films and other extruded or molded parts, in many cases, also could be coated with nylon polymer to enhance surface properties. These properties include for example abrasion resistance, barrier properties or the modification of the surface of a polymer such as polyester to make the surface more polar for a subsequent operations where the modified surface may be more amenable.
  • a coated article comprising a substrate of polyamides, polyesters, or mixtures thereof is first provided. Then a coating solution is applied thereto to form a precoated substrate.
  • the coating solution comprises at least 0.5 weight percent of high imino, partially alkylated, or non- alkylated formaldehyde resins selected from the group consisting of melamine- formaldehyde, glycoluril-formaledhyde, benzoguanamine-formaldehyde and mixtures thereof.
  • a polyamide with a solubility of at least 0.5 weight percent in select organic solvents is applied to the precoated substrate.
  • the thread coating was conducted in a laboratory coating unit similar to the one described in the DuPont brochure relating to Elvamide® (October 1977) and the "Nylon Plastics Handbook", both referenced earlier.
  • the drying and fusing sections are heated with hot nitrogen passed through electrical tube heaters provided with controllers to allow independent temperature control of the two sections.
  • the thread is passed between cheesecloth saturated with the coating solution by continuously dripping the coating solution onto the cloth from a dropping funnel.
  • the residence time of the thread in the drying section is six seconds and also six seconds in the fusing section.
  • the residence time is controlled by the take up speed of the spool motor. To provide a basis for accurate comparisons, the specified threads were always selected from the same spool.
  • the thread After coating the thread is conditioned in a 50% Relative Humidity (RH) chamber for six days before testing.
  • One end of the thread is attached to a reciprocating arm driven by an electric motor (at a rate of 44 cycles/minute) and the other end to a 230.0 g weight (such that the thread abraids against the nylon 66 mono-filament ).
  • the thread hangs over a nylon 66 mono-filament with a diameter of 0.025-inch to 0.030-inch.
  • There is provided a counter that records the number of cycles. During the test, the appearance of the thread is observed visually through a 50X magnifying lens. The point where the coating has abraded is observed as the number of cycles. Increased number of cycles reflects increased abrasion resistance.
  • the interply adhesion of the samples is compared qualitatively by twisting the coated thread opposite the original twist direction.
  • a qualitative grading system from 0 to 3 was used. Zero is when the plies completely separate from each other; 1 is when the plies separate but some portion of the plies are still attached to each other; 2 is when only a small portion of the plies separate from each other; and 3 is when there is no visible separation of the plies. In close cases, gradations in units of 0.5 were used (for example, "1.5" and "2.5").
  • a 210-denier, 3 -ply nylon thread was coated as described above using 6 seconds residence time in the drying section and 6 seconds in the fusing section.
  • Example 1 A methanol solution containing 11.0 weight percent Elvamide® 8061, 2.0 weight percent Cymel® 1135, and 0.2 weight percent p-toluenesulfonic acid was prepared as in Example 1. This solution was used to coat a 210-denier, 3 -ply nylon thread as in Example 1. This example is in accordance with US Patent No. 4,992,515 using a fully alkylated melamine-formaldehyde cross-linking agent and a strong acid catalyst.
  • Solutions for coating were prepared as in the previous examples using a concentration of 11.0 weight percent Elvamide® 8061 in combination with various Cymel® cross-linking agents. These solutions were used to coat 210-denier, 3 -ply nylon thread as in Example 1.
  • Comparative Examples 5 and 6 illustrate the use of another fully alkylated melamine-formaldehyde resin in accordance with US Patent No. 4,992,515.
  • the abrasion resistance was slightly better than with Elvamide® 8061 alone (Comp. Example 1) and with good interply adhesion.
  • the interply adhesion was poor (Comp. Example 6).
  • a 220-denier, 3 -ply polyethyleneterephthalate thread was pre-coated with a 6.0 weight percent Cymel® 350 and 1.0 weight percent p-toluenesulfonic acid catalyst in methanol usining 6 seconds residence time at 80 C in the drying section and 6 seconds at 170 C in the fusion section.
  • the pre-coated thread is then coated as in Example 1 with an 11.0 weight percent solution of Elvamide ® 8061 in methanol without additional catalyst (Examples 37 & 38) and with an 11.0 weight percent Elvamide® 8061 and 1.0 weight percent p-toluenesulfonic acid solution in methanol (Examples 39 & 40).

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Textile Engineering (AREA)
  • Dispersion Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Paints Or Removers (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Laminated Bodies (AREA)
PCT/US2002/007877 2001-03-14 2002-03-14 Coating solutions suitable for improving the adhesion of nylon coatings and processes for the application thereof Ceased WO2002072673A2 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
KR10-2003-7011862A KR20030084979A (ko) 2001-03-14 2002-03-14 나일론 코팅물의 접착성 개선에 적합한 코팅 용액 및 그의적용 방법
CA002437759A CA2437759A1 (en) 2001-03-14 2002-03-14 Coating solutions suitable for improving the adhesion of nylon coatings and processes for the application thereof
EP02725170A EP1373371B1 (en) 2001-03-14 2002-03-14 Coating solutions suitable for improving the adhesion of nylon coatings and processes for the application thereof
JP2002571573A JP4163000B2 (ja) 2001-03-14 2002-03-14 ナイロンコーティングの接着力の改善に適したコーティング溶液およびその塗布方法
AU2002255753A AU2002255753A1 (en) 2001-03-14 2002-03-14 Coating solutions suitable for improving the adhesion of nylon coatings and processes for the application thereof
DE60226315T DE60226315T2 (de) 2001-03-14 2002-03-14 Beschichtungslösungen geeingnet zur verbesserung der haftung von nylon-beschichtungen und verfahren zur anwendung davon

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US60/275,565 2001-03-14

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WO2010028052A1 (en) * 2008-09-08 2010-03-11 Saint-Gobain Performance Plastics Corporation Sanitary coupling assembly
JP5730110B2 (ja) * 2011-04-13 2015-06-03 小松精練株式会社 繊維布帛の製造方法及び繊維布帛
CN102220065A (zh) * 2011-04-26 2011-10-19 安徽汇联机械工业有限公司 汽车轮毂用闪光白色漆

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US3657380A (en) * 1969-12-09 1972-04-18 Du Pont High temperature resistant coating composition of an aromatic polyamide and an epoxy resin
JPH0337283A (ja) * 1989-07-03 1991-02-18 Hitachi Chem Co Ltd 耐熱性塗料及びこれを用いた被覆銅板
US4992515A (en) * 1990-01-09 1991-02-12 Shakespeare Company Nylon terpolymer crosslinked with melamine formaldehyde for coating sewing threads
US6197462B1 (en) * 1999-11-29 2001-03-06 Xerox Corporation Cross-linked polyamide anticurl back coating for electrostatographic imaging members

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EP1373371B1 (en) 2008-04-30
ATE393793T1 (de) 2008-05-15
US20020198330A1 (en) 2002-12-26
WO2002072673A3 (en) 2003-02-13
US6805969B2 (en) 2004-10-19
DE60226315D1 (de) 2008-06-12
DE60226315T2 (de) 2009-06-25
EP1373371A2 (en) 2004-01-02
CN1496385A (zh) 2004-05-12
JP4163000B2 (ja) 2008-10-08
AU2002255753A1 (en) 2002-09-24
JP2004535518A (ja) 2004-11-25
CA2437759A1 (en) 2002-09-19
WO2002072673A8 (en) 2002-11-28
KR20030084979A (ko) 2003-11-01

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