US3154429A - Process for producing an antistatic finish on synthetic fibers - Google Patents

Process for producing an antistatic finish on synthetic fibers Download PDF

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US3154429A
US3154429A US67135A US6713560A US3154429A US 3154429 A US3154429 A US 3154429A US 67135 A US67135 A US 67135A US 6713560 A US6713560 A US 6713560A US 3154429 A US3154429 A US 3154429A
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weight
parts
water
fibers
diglycidyl ether
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US67135A
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Albrecht Valerie
Berger Alfred
Hofmann Walter
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BASF Schweiz AG
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Ciba AG
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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
    • 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
    • D06M13/385—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 epoxy groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/16—Anti-static materials
    • 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
    • D06M13/325—Amines
    • D06M13/332—Di- or polyamines
    • 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
    • D06M15/53—Polyethers
    • 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
    • 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
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/92—Fire or heat protection feature
    • Y10S428/921—Fire or flameproofing
    • 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
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2221—Coating or impregnation is specified as water proof
    • Y10T442/2246—Nitrogen containing
    • 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
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2418—Coating or impregnation increases electrical conductivity or anti-static quality
    • Y10T442/2434—Linear polyether group chain containing

Definitions

  • This invention relates to the treatment of organic, hy-
  • a process for producing a washproof antistatic finish on organic, hydrophobic, synthetic fibrous material which comprises impregnating the said material with an aqueous preparation containing, per 1,000 parts of water,
  • any primary, secondary or tertiary monoor polyamine which is water-soluble to the extent of at least 1.5% by weight may be employed.
  • Examples are ethylene diamine, diethylenetriamine, triethylenetetramine dibutylamine, benzyldimethylamine, triethanolamine, cyclohexylamine, m-phenylenediamine, 2,4,6-tri-(dimethylaminornethyl)phenol and N,N-diethyl- 1,3-diaminopropane.
  • alkylene polyamines include the compounds containing two amino groups which are joined together by an aliphatic bridge composed of m alkylene groups and m-l oxygen atoms, sulfur atoms or NH or N(alkyl) groups, situated between the said alkylene groups (In being an integer). Different alkylene groups and/ or bridging groups situated between them may be present in the molecule of such a polyamine.
  • Preferred alkylenepolyarnines are, therefore, ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylene pentamine, 1,Z-diamino-Z-methylpropane, N,N- dimethyl-l,3-propylenediamine, tetramethyl-diethylenetriamine, pentamethyl-diethylenetriamine, di-(aminoethyl)- ether and di-(aminoethyl)-sulfide.
  • substituted alkylenepolyamines for example those comprising aliphatically saturated or unsaturated, preferably unbranched, hydrocarbon radicals, containing from 12 to 22 carbon atoms, which are attached to a nitrogen atom of the amine, either directly or through bridge members, such as CO-groups, and those cornprising CN-radicals, or, preferably those comprising radicals of the formula n being an integer from 1 to 10 and R a hydrogen atom, an alkyl radical or an acyl radical.
  • substituted alkylenepolyamines for example those comprising aliphatically saturated or unsaturated, preferably unbranched, hydrocarbon radicals, containing from 12 to 22 carbon atoms, which are attached to a nitrogen atom of the amine, either directly or through bridge members, such as CO-groups, and those cornprising CN-radicals, or, preferably those comprising radicals of the formula n being an integer from 1 to 10 and R a hydrogen atom, an alkyl radical or
  • amines obtainable by the addition of acrylonitrile to amines and reduction of the nitrile group 3,l54,429 Patented Oct. 27, 1964 to the amine, and the substitution products thereof, are suitable.
  • Two or more amines of different kinds may be used in the aforesaid preparations.
  • an alkylenepolyamine containing two primary amino groups, such as triethylenetetramine, and an alkylenepolyamine containing at least two tertiary amino groups, such as pentamethyldiethylenetriamine or tetrahydroxyethylenediamine may be employed.
  • the diglycidyl others are derived from polyethyleneglycois of the general formula in which k represents an integer from about 7 to about 35, i.e., polyethyleneglycols having an average molecular weight of 300 to 1,500 preferably those having an average molecular weight of 300 to 1000.
  • diglycidyl ethers of polyethyleneglycols having the defined range of molecular weight is critical. impregnating baths containing only diglycidyl ethers of polyethyleneglycols having a molecular weight of less than 200-300 give dressings on polyester or polyacrylo nitrile fibers which, as compared to dressings obtained from baths containing the defined diglycidyl ethers of higher polyethyleneglycols, are about ten times less antistatic and, moreover, present a yellow appearance. In some cases, preferably when using diglycidylethers of polyethylene glycols having an average molecular Weight of 1000 to 1500, it is advisable to use in addition minor amounts of a diglycidylether of ethylene glycol.
  • the diglycidyl others which are employed in accordance with the invention correspond theoretically to the general formula in which k represents an integer from about 7 to about 35. They are compounds which contain 11 1,2-epoxide groups calculated on the average molecular weight, n being an integer or a fractional number higher than 1.
  • the content of epoxide groups in the diglycidyl ethers is indicated, as usual for epoxy resins, by the number of mols of 1,2-epoxide groups per kg. of epoxide compound (epoxide equivalents/kg).
  • epoxide equivalents/kg epoxide equivalents/kg.
  • products comprising 0.75 to 4.5 epoxide equivalents/kg. can be obtained.
  • diglycidyl ethers comprising 0.95 to 4 epoxide equivalents/kg. are employed.
  • the organic synthetic fibrous material treated by the process of the present invention will usually be hydrophobic in character and examples are semisynthetic fibers such as cellulose ester fibers, for example cellulose dior a triacetate, and fully synthetic fibers such as polyacrylonitrile fibers, polyamide fibers, such as those consisting of e-caprolactarn or of adipic acid and hexamethylene diamine, polyester fibers of the glycol-terephthalic acid type, polyvinyl chloride fibers and polyvinylidene chloride fibers. Fibers consisting of copolymers, and fiber mixtures of different synthetic fibers or of synthetic and natural fibers, may also usefully be 511Djtd to the treatment process of the present invention. There are preferably used polyamide, polyacrylonitrile and polyester fibers.
  • the aqueous preparations may be prepared by combining the necessary constituents in Water.
  • the aqueous preparations contain, per 1,000 parts by weight of water, from 6 to 18 parts by weight of one or more diglycidyl ethers of the type defined above and from 0.4 to 15 parts, preferably from 0.8 to 8 parts by weight of one or more water-soluble amines.
  • the aqueous preparations contain, per 1,000 parts by weight of water, from 6 to 18 parts by weight of one or more diglycidyl ethers of the type defined above and from 0.4 to 15 parts, preferably from 0.8 to 8 parts by weight of one or more water-soluble amines.
  • the quantity of amine to be employed depends, as mentioned, primarily on the number of epoxide groups present. As a rule of thumb, the above-indicated quantity of from 0.4 to 15 parts of amine holds good. If the excess of amine is too great, no wash-proof antistatic finish is obtained.
  • the impregnation of the synthetic fibrous material, e.g., textile fibers, with the aqueous preparations advantageously takes place at room temperature, for example by simply immersing or spraying, preferably on a padding machine.
  • the impregnated fibrous material is passed through squeeze rolls to remove any excess solution and to ensure uniform impregnation.
  • the fibers are dried,
  • the drying may be omitted and the fibrous material exposed directly to relatively high temperatures to harden the diglycidyl ether.
  • the impregnation is hardened at a temperature sufiicient to convert the diglycidyl ether to the water-insoluble state.
  • the higher the hardening temperature the shorter is the time required for the hardening treatment.
  • the hardening may be continued for about 4 hours, at 80 C. for from 1 to 1% hours, at 100 C. for from 20 to 30 minutes, and at 120 for about to minutes.
  • the impregnations may also be cured at room temperatures, i.e., at temperatures from to C., the hardening time being about 24 hours. Temperatures lower than 15 C. are not recommended because the hardening requires too much time. Temperatures between 15 C. and 130 C. have proved particularly satisfactory. The temperature may be even higher, for example 150, but the danger of yellowing of the fibers then arises.
  • the synthetic fibers are padded into the aqueous preparation, squeezed so that from 0.25% to 3%, preferably from 0.5% to 2% and more particularly about 1% of the solids, i.e., diglycidyl ether and amine, are deposited on the fibers, dried and hardened as indicated above.
  • the amount of solids deposited on the fibers is critical. When less than about 0.25 is present there are obtained insufiicint antistatic efiects and when more than about 3% are deposited the fibers may acquire a stiffening touch.
  • the degree of squeezing depends on the fiber material, usually it is squeezed to a weight increase of between and 130% on the weight of the original fabric. As a rule, nylon, polyacrylonitrile and polyester fibers are squeezed to a weight increase of 120%, and 80%.
  • Synthetic fibers treated by the process of the invention possess good antistatic properties, which are substantially maintained even after washing.
  • polyglycidyl ethers A to H mentioned in the examples are the following products:
  • Diglycidyl ether A from ethylene-glycol 4.0
  • Diglycidyl ether B from polyethylene-glycol 300 3.2
  • Diglycidyl ether C from polyethylene-glycol 300 3.5
  • Diglycidyl ether D from polyethylene-glycol 300 3.75
  • Diglycidyl ether E from polyethylene-glycol 400 2.8
  • Diglycidyl ether F from polyethylene-glycol 600 1.45
  • Diglycidyl ether G from polyethylene-glycol 1,000 0.95
  • Diglycidyl ether H from polyethylene-glycol 1,500 0.75
  • Example 1 6.2 parts of diglycidyl ether B and 0.5 part of triethylenetetramine are dissolved in 365 parts of water to form impregnating bath I. The same material, in the same quantities, are dissolved in 800 parts of water to form impregnating bath II.
  • a polyamide woven fabric is padded with impregnating bath I and therefore squeezed to a weight increase of 55% on the weight of the original fabric.
  • the impregnated fabric is dried and the impregnation is hardened at 120 for 10 minutes.
  • a polyacrylonitrile fabric is impregnated on the padding machine with impregnating bath II and squeezed to a weight increase of 120% on the weight of the original fabric and dried and hardened as in the case of the impregnating bath I.
  • the fabrics thus treated possess good antistatic properties, which are wash-resistant.
  • the specific surface resistance amounts to 10 ohms. After washing five times each for hour with 5 g. of soap per liter at 50, the specific surface resistance amounts to 10 ohms.
  • the specific surface resistance is 10 ohms, and after washing five times it is 10 ohms.
  • the specific surface resistance of the untreated fabric amounts to more than 10 ohms.
  • Example 3 6.9 parts of diglycidyl ether F, 2.5 parts of diglycidyl ether A and 0.5 part of triethylenetetramine are dissolved in 540 parts of water to form impregnating bath I and the same materials in the same quantities are dissolved in 1100 parts of water to form impregnating bath II.
  • a polyamide fabric is padded with impregnating bath I, as described in Example 2, squeezed, dried and hardened.
  • a polyacrylonitrile fabric is padded with impregnating bath II and squeezed to weight increase of 120% on the weight of the original fabric.
  • the fabric thus treated is dried, and the impregnation is hardened for minutes at 120.
  • Example 4 A mixture of (a) 0.82 part of the compound of the formula C H NHCH CH CH NH (b) 1.24 parts of diglycidyl ether B,
  • Polyamide fabric is padded with this impregnating bath and squeezed to a weight increase of about 55% based on the original weight of the fabric.
  • the fabric is dried and the impregnation is hardened for 10 minutes at 120.
  • the polyamide fabric thus obtained possesses good antistatic properties which are wash-resistant.
  • Example 5 Polyamide fabrics are separately impregnated in baths, which contain each in 1,000 parts of water, the following (a) 10.1 parts of diglycidyl ether G, 7.2 parts of diglycidyl ether A and 0.96 part of triethylenetetramine, (b) 11.1 parts of diglycidylether H, 6.1 parts of diglycidylether A and 0.83 part of triethylenetetramine.
  • the fabrics are dried and then heated for 5 minutes at 150.
  • Example 6 7.2 parts of diglycidyl ether E and 0.5 part of triethylene-tetramine are dissolved in 500 parts of water. Polyamide fabric is impregnated squeezed to a weight increase of 58% and the weight of the original fabric dried and hardened for 10 minutes at 125.
  • the specific surface resistance of the finished fabric is 10 ohms, and after washing is 10 ohms.
  • Example 7 10.1 parts of diglycidylether C and 2.4 parts of an addition product of 2 mol of ethylene oxide to 1 mol of diethylenetriamine are dissolved in 1,000 parts of water.
  • Polyester fabric is padded in the solution, squeezed to a weight increase of 80% and the Weight of the original fabric dried and hardened for 5 minutes at 150.
  • the specific surface resistance of the finished fabric is 10 ohms, and after washing remains at 10 ohms.
  • the specific surface resistance of the original fabric amounts to 10 ohms.
  • Example 8 28.6 parts of diglycidylether C, 5.15 parts of diethylene-triamine and 20 parts of butanol are boiled under reflux for 1 hour with stirring.
  • a fabric consisting of polyvinylchloride is impregnated with this solution, squeezed to a weight increase of 40% on the weight of the original fabric, dried and thereafter maintained for 20 hours at 40-45 A good wash-resistant antistatic finish is obtained.
  • Example 10 2 parts of diglycidyl ether D and 0.2 part of triethylene tetramine are dissolved in 110 parts of water to form impregnating bath I, the same materials in the same quantities are dissolved in 240 parts of water to form impregnating bath II, and the same materials in the same quantities are dissolved in 160 parts of water to form impregnating bath III.
  • a polyamide fabric is impregnated with impregnating bath 1, squeezed to increase in weight and dried for 15 to 30 minutes.
  • a polyacrylonitrile fabric is impregnated with impregnating bath II, squeezed to 120% increase in weight and dried for 15 to 30' minutes.
  • a polyester fabric is impregnated with impregnating bath III, squeezed to 80% increase in weight and dried for 15 to 30 minutes.
  • the treated fabrics are left at room temperature, i.e., about 20 C. From time to time test samples of these fabrics are each washed with 5 grams of soap in a liter of water for 30 minutes at 50 C., and the specific surface resistance measured.
  • the following table shows that after storage for 24 hours the dressings are fast to washing, i.e., the antistatic eifect is practically the same before and after washing.
  • the fibers are padded and squeezed according to the following data:
  • Samples of the treated fibers are washed 5 times for /2 hour each time with 5 g. of soap per liter at 50 C.
  • the specific surface resistance amounts to the following values.
  • a process for producing a wash-proof antistatic finish on organic hydrophobic synthetic fibers which comprises impregnating said fibers with an aqueous preparation containing, as the only active ingredients, per 1000 parts by weight of water,
  • a process for producing a wash-proof antistatic finish on organic hydrophobic synthetic fibers which comprises impregnating said fibers with an aqueous preparation containing, as the only active ingredients, per 1000 parts by weight of water,
  • a process for producing a wash-proof antistatic finish on organic hydrophobic synthetic fibers selected from the group consisting of polyamides, polyacrylonitriles and polyesters which comprises impregnating said fibers with an aqueous preparation containing, as the only active ingredients, per 1,000 parts by weight of water,
  • a process for producing a wash-proof antistatic finish on hydrophobic synthetic polyester fibers which comprises impregnating said fibers with an aqueous preparation containing as the only active ingredients, per 1,000 parts by weight of water,
  • a process for producing a wash-proof antistatic finish on hydrophobic synthetic polyamide fibers which comprises impregnating said fibers with an aqueous preparation containing, as the only active ingredients, per 1,000 parts by weight of water,
  • a process for producing a wash-proof antistatic finish on hydrophobic polyacrylonitrile fibers which comprises impregnating said fibers with an aqueous preparation containing, as the only active ingredients, per 1,000 parts by weight of water,
  • An organic synthetic hydrophobic textile fiber having applied thereto in an amount of 0.5 to 2 percent calculated on the weight of said fiber the product obtained by reacting exclusively a water-soluble amine, as such with a water-soluble diglycidyl ether of a polyethylene glycol having an average molecular Weight of 300 to 1500, which diglycidylether contains 0.75 to 4.5 epoxide equivalents per kg.

Description

United States Patent T This is a continuation in part of our application Ser. No. 826,146, filed July 10, 1959 (now abandoned).
This invention relates to the treatment of organic, hy-
drophobic, synthetic fibers to impart antistatic properties thereto.
According to the present invention a process for producing a washproof antistatic finish on organic, hydrophobic, synthetic fibrous material which comprises impregnating the said material with an aqueous preparation containing, per 1,000 parts of water,
(a) 3 to 25 parts of a Water-soluble diglycidyl ether of a polyethylene glycol having an average molecular weight of 300 to 1500, which diglycidylether contains 0.75 to 4.5 epoxide equivalents per kg, and
(b) 0.4 to parts of a water-soluble amine,
squeezing the fibrous material to such an extent that from 0.5 to 2 percent by weight of solids, calculated on the weight of the dry fibrous material are deposited, drying the impregnated fibrous material and curing it at a te. perature sufficient to convert the diglycidyl ether to the waterinsoluble state.
As water-soluble amines any primary, secondary or tertiary monoor polyamine, which is water-soluble to the extent of at least 1.5% by weight may be employed. Examples are ethylene diamine, diethylenetriamine, triethylenetetramine dibutylamine, benzyldimethylamine, triethanolamine, cyclohexylamine, m-phenylenediamine, 2,4,6-tri-(dimethylaminornethyl)phenol and N,N-diethyl- 1,3-diaminopropane.
It is particularly preferred to use alkylene polyamines. These include the compounds containing two amino groups which are joined together by an aliphatic bridge composed of m alkylene groups and m-l oxygen atoms, sulfur atoms or NH or N(alkyl) groups, situated between the said alkylene groups (In being an integer). Different alkylene groups and/ or bridging groups situated between them may be present in the molecule of such a polyamine.
Preferred alkylenepolyarnines are, therefore, ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylene pentamine, 1,Z-diamino-Z-methylpropane, N,N- dimethyl-l,3-propylenediamine, tetramethyl-diethylenetriamine, pentamethyl-diethylenetriamine, di-(aminoethyl)- ether and di-(aminoethyl)-sulfide. There may also be employed substituted alkylenepolyamines, for example those comprising aliphatically saturated or unsaturated, preferably unbranched, hydrocarbon radicals, containing from 12 to 22 carbon atoms, which are attached to a nitrogen atom of the amine, either directly or through bridge members, such as CO-groups, and those cornprising CN-radicals, or, preferably those comprising radicals of the formula n being an integer from 1 to 10 and R a hydrogen atom, an alkyl radical or an acyl radical.
In addition, amines obtainable by the addition of acrylonitrile to amines and reduction of the nitrile group 3,l54,429 Patented Oct. 27, 1964 to the amine, and the substitution products thereof, are suitable.
Two or more amines of different kinds may be used in the aforesaid preparations. For example, an alkylenepolyamine containing two primary amino groups, such as triethylenetetramine, and an alkylenepolyamine containing at least two tertiary amino groups, such as pentamethyldiethylenetriamine or tetrahydroxyethylenediamine may be employed.
Good wash resistance is obtained if approximately one active hydrogen atom of an amine is present per epoxide group of the diglycidylether. Thus for example, /6 mol of triethylenetetramine to one epoxide group of the diglycidylether is preferred, because the former contains six active hydrogen atoms. If an amine is employed which possesses no active hydrogen atoms attached to nitrogen, as in the case of the above-mentioned tertiary amines, from 0.5 to 2, preferably 1, tertiary amino groups of the tertiary amine is present per epoxide group.
The diglycidyl others are derived from polyethyleneglycois of the general formula in which k represents an integer from about 7 to about 35, i.e., polyethyleneglycols having an average molecular weight of 300 to 1,500 preferably those having an average molecular weight of 300 to 1000.
The use of diglycidyl ethers of polyethyleneglycols having the defined range of molecular weight is critical. impregnating baths containing only diglycidyl ethers of polyethyleneglycols having a molecular weight of less than 200-300 give dressings on polyester or polyacrylo nitrile fibers which, as compared to dressings obtained from baths containing the defined diglycidyl ethers of higher polyethyleneglycols, are about ten times less antistatic and, moreover, present a yellow appearance. In some cases, preferably when using diglycidylethers of polyethylene glycols having an average molecular Weight of 1000 to 1500, it is advisable to use in addition minor amounts of a diglycidylether of ethylene glycol.
The diglycidyl others which are employed in accordance with the invention correspond theoretically to the general formula in which k represents an integer from about 7 to about 35. They are compounds which contain 11 1,2-epoxide groups calculated on the average molecular weight, n being an integer or a fractional number higher than 1. The products possess from 1.1 to 2 epoxide groups per average molecular weight, and they are preferably obtained by reacting the defined polyethylene glycols with epichlorhydrin in the presence of a Friedel-Crafts catalyst and subsequently dehydrohalogenating the product with alkali.
The content of epoxide groups in the diglycidyl ethers is indicated, as usual for epoxy resins, by the number of mols of 1,2-epoxide groups per kg. of epoxide compound (epoxide equivalents/kg). Depending upon the nature of the polyethylene glycol employed and upon the reaction conditions in the preparation of the diglycidyl ethers, products comprising 0.75 to 4.5 epoxide equivalents/kg. can be obtained. Preferably, diglycidyl ethers comprising 0.95 to 4 epoxide equivalents/kg. are employed.
The organic synthetic fibrous material treated by the process of the present invention will usually be hydrophobic in character and examples are semisynthetic fibers such as cellulose ester fibers, for example cellulose dior a triacetate, and fully synthetic fibers such as polyacrylonitrile fibers, polyamide fibers, such as those consisting of e-caprolactarn or of adipic acid and hexamethylene diamine, polyester fibers of the glycol-terephthalic acid type, polyvinyl chloride fibers and polyvinylidene chloride fibers. Fibers consisting of copolymers, and fiber mixtures of different synthetic fibers or of synthetic and natural fibers, may also usefully be 511Djtd to the treatment process of the present invention. There are preferably used polyamide, polyacrylonitrile and polyester fibers.
The aqueous preparations may be prepared by combining the necessary constituents in Water. Preferably, the aqueous preparations contain, per 1,000 parts by weight of water, from 6 to 18 parts by weight of one or more diglycidyl ethers of the type defined above and from 0.4 to 15 parts, preferably from 0.8 to 8 parts by weight of one or more water-soluble amines. Generally speaking, at most only a minor improvement in antistatic properties, if any, is obtained when using more than 25 parts of diglycidyl ether. When less than three parts of diglycidyl ether are employed, the antistatic effects obtained are generally inadequate. The quantity of amine to be employed depends, as mentioned, primarily on the number of epoxide groups present. As a rule of thumb, the above-indicated quantity of from 0.4 to 15 parts of amine holds good. If the excess of amine is too great, no wash-proof antistatic finish is obtained.
The impregnation of the synthetic fibrous material, e.g., textile fibers, with the aqueous preparations advantageously takes place at room temperature, for example by simply immersing or spraying, preferably on a padding machine. The impregnated fibrous material is passed through squeeze rolls to remove any excess solution and to ensure uniform impregnation. The fibers are dried,
advantageously at moderate temperatures, for example between 30 C. and 50 C. In some cases, the drying may be omitted and the fibrous material exposed directly to relatively high temperatures to harden the diglycidyl ether. The impregnation is hardened at a temperature sufiicient to convert the diglycidyl ether to the water-insoluble state. The higher the hardening temperature, the shorter is the time required for the hardening treatment. Thus, at 40 C. the hardening may be continued for about 4 hours, at 80 C. for from 1 to 1% hours, at 100 C. for from 20 to 30 minutes, and at 120 for about to minutes. The impregnations may also be cured at room temperatures, i.e., at temperatures from to C., the hardening time being about 24 hours. Temperatures lower than 15 C. are not recommended because the hardening requires too much time. Temperatures between 15 C. and 130 C. have proved particularly satisfactory. The temperature may be even higher, for example 150, but the danger of yellowing of the fibers then arises.
The synthetic fibers are padded into the aqueous preparation, squeezed so that from 0.25% to 3%, preferably from 0.5% to 2% and more particularly about 1% of the solids, i.e., diglycidyl ether and amine, are deposited on the fibers, dried and hardened as indicated above. The amount of solids deposited on the fibers is critical. When less than about 0.25 is present there are obtained insufiicint antistatic efiects and when more than about 3% are deposited the fibers may acquire a stiffening touch. The degree of squeezing depends on the fiber material, usually it is squeezed to a weight increase of between and 130% on the weight of the original fabric. As a rule, nylon, polyacrylonitrile and polyester fibers are squeezed to a weight increase of 120%, and 80%.
Synthetic fibers treated by the process of the invention possess good antistatic properties, which are substantially maintained even after washing.
In the following examples, where not otherwise stated, the parts are indicated by weight, the percentages by weight and the temperature in degrees centigrade.
The polyglycidyl ethers A to H mentioned in the examples are the following products:
Epoxide equivalents/ kg. Diglycidyl ether A: from ethylene-glycol 4.0 Diglycidyl ether B: from polyethylene-glycol 300 3.2 Diglycidyl ether C: from polyethylene-glycol 300 3.5 Diglycidyl ether D: from polyethylene-glycol 300 3.75 Diglycidyl ether E: from polyethylene-glycol 400 2.8 Diglycidyl ether F: from polyethylene-glycol 600 1.45 Diglycidyl ether G: from polyethylene-glycol 1,000 0.95 Diglycidyl ether H: from polyethylene-glycol 1,500 0.75
Example 1 6.2 parts of diglycidyl ether B and 0.5 part of triethylenetetramine are dissolved in 365 parts of water to form impregnating bath I. The same material, in the same quantities, are dissolved in 800 parts of water to form impregnating bath II.
A polyamide woven fabric is padded with impregnating bath I and therefore squeezed to a weight increase of 55% on the weight of the original fabric. The impregnated fabric is dried and the impregnation is hardened at 120 for 10 minutes.
A polyacrylonitrile fabric is impregnated on the padding machine with impregnating bath II and squeezed to a weight increase of 120% on the weight of the original fabric and dried and hardened as in the case of the impregnating bath I.
The fabrics thus treated possess good antistatic properties, which are wash-resistant.
The same procedure is followed as above, with the difference that a solution of 5.6 parts of diglycidyl ether C and 0.5 part of triethylene-tetramine, on the one hand in 355 parts of water (impregnating bath 1) and on the other hand in 740 parts of water (impregnating bath II) is used.
On the finished polyamide fabric, the specific surface resistance amounts to 10 ohms. After washing five times each for hour with 5 g. of soap per liter at 50, the specific surface resistance amounts to 10 ohms.
On the finished polyacrylonitrile fabric, the specific surface resistance is 10 ohms, and after washing five times it is 10 ohms.
In both cases, the specific surface resistance of the untreated fabric amounts to more than 10 ohms.
5.6 parts of diglycidyl ether C and 0.5 part of triethylene tetramine are dissolved in 490 parts of water. A polyester fabric of the glycol-terephthalic acid type is impregnated on the padding machine with this bath and squeezed to a weight increase of on the weight of the original fabric and dried and hardened at 125 C. for 10 minutes. On the finished polyester fabric, the specific surface resistance is 10 ohms, and after washing five times it is 10 ohms. The untreated fabric has a resistance of about 10 ohms.
Example 2 4 parts of the compound of the formula:
and 9 parts of diglycidyl ether B are dissolved in 700 parts of water. A polyamide fabric (nylon) is padded with this impregnating bath and squeezed to a weight increase of 55% on the weight of the original fabric. After drying and hardening for 10 minutes at the fabric possesses Wash-resistant antistatic properties.
Example 3 6.9 parts of diglycidyl ether F, 2.5 parts of diglycidyl ether A and 0.5 part of triethylenetetramine are dissolved in 540 parts of water to form impregnating bath I and the same materials in the same quantities are dissolved in 1100 parts of water to form impregnating bath II.
A polyamide fabric is padded with impregnating bath I, as described in Example 2, squeezed, dried and hardened.
A polyacrylonitrile fabric is padded with impregnating bath II and squeezed to weight increase of 120% on the weight of the original fabric. The fabric thus treated is dried, and the impregnation is hardened for minutes at 120.
In both cases, fabrics having good antistatic properties are obtained.
Example 4 A mixture of (a) 0.82 part of the compound of the formula C H NHCH CH CH NH (b) 1.24 parts of diglycidyl ether B,
(c) 0.5 part of diglycidyl ether A, and
(d) 0.05 part of triethylenetetramine is dissolved in 140 parts of water.
Polyamide fabric is padded with this impregnating bath and squeezed to a weight increase of about 55% based on the original weight of the fabric. The fabric is dried and the impregnation is hardened for 10 minutes at 120.
The polyamide fabric thus obtained possesses good antistatic properties which are wash-resistant.
Example 5 Polyamide fabrics are separately impregnated in baths, which contain each in 1,000 parts of water, the following (a) 10.1 parts of diglycidyl ether G, 7.2 parts of diglycidyl ether A and 0.96 part of triethylenetetramine, (b) 11.1 parts of diglycidylether H, 6.1 parts of diglycidylether A and 0.83 part of triethylenetetramine.
In each case after squeezing to a weight reduction of 55% based on the original weight of fabric, the fabrics are dried and then heated for 5 minutes at 150.
Good wash-resistant anti-static finishes are obtained in all two cases.
Example 6 7.2 parts of diglycidyl ether E and 0.5 part of triethylene-tetramine are dissolved in 500 parts of water. Polyamide fabric is impregnated squeezed to a weight increase of 58% and the weight of the original fabric dried and hardened for 10 minutes at 125.
The specific surface resistance of the finished fabric is 10 ohms, and after washing is 10 ohms.
Example 7 10.1 parts of diglycidylether C and 2.4 parts of an addition product of 2 mol of ethylene oxide to 1 mol of diethylenetriamine are dissolved in 1,000 parts of water.
Polyester fabric is padded in the solution, squeezed to a weight increase of 80% and the Weight of the original fabric dried and hardened for 5 minutes at 150.
The specific surface resistance of the finished fabric is 10 ohms, and after washing remains at 10 ohms.
The specific surface resistance of the original fabric amounts to 10 ohms.
Example 8 28.6 parts of diglycidylether C, 5.15 parts of diethylene-triamine and 20 parts of butanol are boiled under reflux for 1 hour with stirring.
After addition of about 50 parts of water to the viscous product, the butanol is removed by distillation with water in vacuo, and the residue is then brought to 67.5 parts with water.
3.3 parts of the highly water-soluble product obtained and 1.4 parts of diglycidyl ether C are dissolved together in 220 parts of water. A cellulose acetate fabric is impregnated in this bath, squeezed to a weight increase of 73% on the weight of the original fabric and hardened for 10 minutes at 120125.
A good wash-resistant antistatic finish is obtained.
G Example 9 1.7 parts of diglycidyl ether C, 0.05 part of triethylenetetramine and 0.35 part of pentamethyldiethylenetriamine are dissolved in 76 parts of water.
A fabric consisting of polyvinylchloride is impregnated with this solution, squeezed to a weight increase of 40% on the weight of the original fabric, dried and thereafter maintained for 20 hours at 40-45 A good wash-resistant antistatic finish is obtained.
Example 10 2 parts of diglycidyl ether D and 0.2 part of triethylene tetramine are dissolved in 110 parts of water to form impregnating bath I, the same materials in the same quantities are dissolved in 240 parts of water to form impregnating bath II, and the same materials in the same quantities are dissolved in 160 parts of water to form impregnating bath III.
A polyamide fabric is impregnated with impregnating bath 1, squeezed to increase in weight and dried for 15 to 30 minutes.
A polyacrylonitrile fabric is impregnated with impregnating bath II, squeezed to 120% increase in weight and dried for 15 to 30' minutes.
A polyester fabric is impregnated with impregnating bath III, squeezed to 80% increase in weight and dried for 15 to 30 minutes.
The treated fabrics are left at room temperature, i.e., about 20 C. From time to time test samples of these fabrics are each washed with 5 grams of soap in a liter of water for 30 minutes at 50 C., and the specific surface resistance measured.
The following table shows that after storage for 24 hours the dressings are fast to washing, i.e., the antistatic eifect is practically the same before and after washing.
Specific surface resistance in ohms Polyamide Polyacrylo- Polyester fabric nitrile fabric fabric Dried, unwashed 10 10 10 Dried, washed immediately 10 10 10 Dried, washed after 8 hours 10 10 10 Dried, washed after 24 hours. 10 10 10 Dried, washed after 6 days 10- 10 10 Untreated 10 10 10 Example 11 This example shows the difference of antistatic effects obtained by treating synthetic fibers with (1) a bath containing a diglycidylether of polyethylene glycol 300 and (2) a bath containing a diglycidylether of ethylene glycol Y only.
The fibers are padded and squeezed according to the following data:
Bath containing in 1,000 parts of Water Pick-up, Fibers Parts of Parts of Parts of percent diglydiglytricidyl cidyl ethylene ether C ether A tramine Poly 1.82 55 2. 1 55 0.83 120 0. 96 120 1. 25 1. 44 80 The fibers are hardened for 10 minutes at -125 C.
Samples of the treated fibers are washed 5 times for /2 hour each time with 5 g. of soap per liter at 50 C.
The specific surface resistance amounts to the following values.
What is claimed is:
1. A process for producing a wash-proof antistatic finish on organic hydrophobic synthetic fibers which comprises impregnating said fibers with an aqueous preparation containing, as the only active ingredients, per 1000 parts by weight of water,
(a) 3 to 25 parts by weight of a water-soluble diglycidyl ether of a polyethylene glycol having an average molecular weight of 300 to 1500, which diglycidyl ether contains 0.75 to 4.5 epoxide equivalents per kg., as such, and
(b) 0.4 to 15 parts by weight of a water-soluble amine, squeezing the fibers to such an extent that from about 0.5 to 2 percent by weight of solids, calculated on the weight of the dry fibrous material, are deposited, drying the impregnated fibers and curing the impregnated material at a temperature suificient to convert the diglycidyl ether to the water-insoluble state.
2. A process for producing a wash-proof antistatic finish on organic hydrophobic synthetic fibers which comprises impregnating said fibers with an aqueous preparation containing, as the only active ingredients, per 1000 parts by weight of water,
(a) 3 to 25 parts by weight of a Water-soluble diglycidyl ether of a polyethylene glycol having an average molecular weight of 300 to 1500, which diglycidyl ether contains 0.75 to 4.5 epoxide equivalents per kg, and
(b) 0.4 to 15 parts by weight of a water-soluble alkylenepolyamine, as such,
squeezing the fibers to such an extent that from about 0.5 to 2 percent by weight of solids, calculated on the weight of the dry fibrous material, are deposited, drying the impregnated fibers and curing the impregnated material at a temperature sufiicient to convert the diglycidylether to the water-insoluble state.
3. A process for producing a wash-proof antistatic finish on organic hydrophobic synthetic fibers selected from the group consisting of polyamides, polyacrylonitriles and polyesters which comprises impregnating said fibers with an aqueous preparation containing, as the only active ingredients, per 1,000 parts by weight of water,
(a) 6 to 18 parts by weight of a water-soluble diglycidyl ether containing 3.2 to 3.75 epoxide equivalents per kg. of a polyethyleneglycol having an average molecular weight of 300, and
(b) 0.8 to 8 parts by weight of triethylenetetramine,
as such,
squeezing the fibers to such an extent that from about 0.5 to 2 percent by weight of solids, calculated on the weight of the dry fibrous material, are deposited, drying the impregnated fibers and curing the impregnated material at a temperature sufficient to convert the diglycidylether to the water-insoluble state.
4. A process for producing a wash-proof antistatic finish on hydrophobic synthetic polyester fibers which comprises impregnating said fibers with an aqueous preparation containing as the only active ingredients, per 1,000 parts by weight of water,
(a) 10 to 13 parts by weight of a water-soluble diglycidyl ether containing 3.2 to 3.75 epoxide equivalents per kg. of a polyethyleneglycol having an average molecular weight of 300, and
(b) 1 to 1.3 part by weight of triethylenetetramine,
as such,
squeezing the fibers to such an extent that from about 0.5 to 2 percent by weight of solids, calculated on the weight of the dry fibrous material, are deposited, drying the impregnated fibers and curing the impregnated material at a temperature sufiicient to convert the diglycidyl ether to the water-insoluble state.
5. A process for producing a wash-proof antistatic finish on hydrophobic synthetic polyamide fibers which comprises impregnating said fibers with an aqueous preparation containing, as the only active ingredients, per 1,000 parts by weight of water,
(a) 15 to 18 parts by weight of a water-soluble diglycidyl ether containing 3.2 to 3.75 epoxide equivalents per kg. of a polyethylene glycol having an average molecular weight of 300, and
(b) 1.5 to 1.8 parts by weight of triethylene tetramine,
a such,
squeezing the fibers to such an extent that from about 0.5 to 2 percent by weight of solids, calculated on the weight of the dry fibrous material, are deposited, drying the impregnated fibers and curing the impregnated material at a temperature sufiicient to convert the diglycidyl ether to the water-insoluble state.
6. A process for producing a wash-proof antistatic finish on hydrophobic polyacrylonitrile fibers which comprises impregnating said fibers with an aqueous preparation containing, as the only active ingredients, per 1,000 parts by weight of water,
(a) 7 to 8.5 parts by weight of a water-soluble diglycidyl ether containing 3.2 to 3.75 epoxide equivalents per kg. of polyethylene glycol having an average molecular weight of 300, and
(b) 0.6 to 0.8 part by weight of triethylene tetrarnine,
as such,
squeezing the fibers to such an extent that from about 0.5 to 2 percent by weight of solids, calculated on the weight of the dry fibrous material, are deposited, drying the impregnated fibers and curing the impregnated material at a temperature sufficient to convert the diglycidyl ether to the water-insoluble state.
7. An organic synthetic hydrophobic textile fiber having applied thereto in an amount of 0.5 to 2 percent calculated on the weight of said fiber the product obtained by reacting exclusively a water-soluble amine, as such with a water-soluble diglycidyl ether of a polyethylene glycol having an average molecular Weight of 300 to 1500, which diglycidylether contains 0.75 to 4.5 epoxide equivalents per kg.
8. An organic synthetic hydrophobic textile fiber having improved antistatic properties coated with the product obtained by reacting exclusively a water-soluble alkylenepolyamine, as such, with a water-soluble diglycidyl ether of a polyethylene glycol having an average molecular weight of 300 to 1500, which diglycidylether contains 0.75 to 4.5 epoxide equivalents per kg., the amount of the coating being from 0.5 to 2 percent calculated on the weight of said fiber.
9. An organic synthetic hydrophobic textile fiber having improved antistatic properties coated with the product obtained by reacting exclusively a Water-soluble alkylenepolyamine, as such, with a water-soluble diglycidylether of a polyethylene glycol having an average molecular weight of 300 to 1500, which diglycidylether contains 0.75 to 4.5 epoxide equivalents per kg., the amount of the coating being from about one percent calculated on the weight of said fiber.
References Cited in the file of this patent UNITED STATES PATENTS Schroeder Sept. 8, 1959

Claims (1)

1. A PROCESS FOR PRODUCING A WASH-PROOF ANTISTATIC FINISH ON ORGANIC HYDROPHOBIC SYNTHETIC FIBERS WHICH COMPRISES IMPREGNATING SAID FIBERS WITH AN AQUEOUS PREPARAION CONTAINING, AS THE ONLY ACTIVE INGREDIENTS, PER 1000 PARTS BY WEIGHT OF WATER, (A) 3 TO 25 PARTS BY WEIGHT OF A WATER-SOLUBLE DIGLYCIDYL ETHER OF A POLYETHYLENE GLYCOL HAVING AVERAGE MOLECULAR WEIGHT OF 300 TO 1500, WHICH DIGLYCIDYL ETHER CONTAINS 0.75 TO 4.5 EPOXIDE EQUIVALENTS PER KG., AS SUCH AND (B) 0.4 TO 15 PARTS BY WEIGHT OF A WATER-SOLUBLE AMINE, SQUEEZING THE FIBERS TO SUCH AN EXTENT THAT FROM ABOUT 0.5 TO 2 PERCENT BY WEIGHT OF SOLIDS, CALCULATED ON THE WEIGHT OF THE DRY FIBROUS MATERIAL, ARE DEPOSITED, DRYING THE IMPREGNATED FIBERS AND CURING THE IMPREGNATED MATERIAL AT A TEMPERATURE SUFFICIENT TO CONVERT THE DIGLYCIDYL ETHER TO THE WATER-INSOLUBLE STATE.
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US3383242A (en) * 1963-01-22 1968-05-14 Glanzstoff Ag Pretreatment of polyethylene terephthalate filaments for subsequent rubber adhesion
US3411945A (en) * 1965-03-15 1968-11-19 American Cyanamid Co Process for providing a durable antistatic finish for synthetic textile materials
US3441435A (en) * 1964-04-08 1969-04-29 Bayer Ag Process and composition for imparting antistatic finish to textile materials
US3503795A (en) * 1967-05-04 1970-03-31 American Cyanamid Co Durable resinous antistatic textile finish
US4151139A (en) * 1971-08-25 1979-04-24 Sandoz Ltd. Water soluble polyglycol diepoxide-polyamine amide reaction products as antistatic agents
US4197389A (en) * 1977-07-18 1980-04-08 Hoechst Aktiengesellschaft Hardening agent for aqueous epoxy resin compositions
US4847360A (en) * 1987-03-02 1989-07-11 The Firestone Tire & Rubber Company Adhesive active finish for reinforcing members and related methods

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US3227456A (en) * 1961-12-15 1966-01-04 Eric O Sonneman Golf ball coated with a surface active chemical agent
IT699942A (en) * 1963-04-11
CH548481A (en) * 1971-12-03 1974-04-30

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US2903381A (en) * 1954-09-03 1959-09-08 Shell Dev Treatment of synthetic textiles with a polyepoxide having a plurality of 1,2 epoxy groups
US2965517A (en) * 1958-01-21 1960-12-20 Ciba Ltd Process for producing antistatic dressings on synthetic fibers

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DE1010736B (en) * 1952-11-19 1957-06-19 Bayer Ag Process for the production of high molecular weight, water-soluble, basic condensation products
US2829071A (en) * 1954-04-26 1958-04-01 Shell Dev Treatment of wool containing textiles
BE538464A (en) * 1954-05-26
DE1006828B (en) * 1954-09-03 1957-04-25 Bataafsche Petroleum Process for increasing the dyeability of textiles made from synthetic fibers and fabrics
US2817602A (en) * 1956-09-18 1957-12-24 Jr Clay E Pardo Shrinkproofing of wool with epoxy resins and polyalkyleneimines

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US2903381A (en) * 1954-09-03 1959-09-08 Shell Dev Treatment of synthetic textiles with a polyepoxide having a plurality of 1,2 epoxy groups
US2965517A (en) * 1958-01-21 1960-12-20 Ciba Ltd Process for producing antistatic dressings on synthetic fibers

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3383242A (en) * 1963-01-22 1968-05-14 Glanzstoff Ag Pretreatment of polyethylene terephthalate filaments for subsequent rubber adhesion
US3441435A (en) * 1964-04-08 1969-04-29 Bayer Ag Process and composition for imparting antistatic finish to textile materials
US3411945A (en) * 1965-03-15 1968-11-19 American Cyanamid Co Process for providing a durable antistatic finish for synthetic textile materials
US3503795A (en) * 1967-05-04 1970-03-31 American Cyanamid Co Durable resinous antistatic textile finish
US4151139A (en) * 1971-08-25 1979-04-24 Sandoz Ltd. Water soluble polyglycol diepoxide-polyamine amide reaction products as antistatic agents
US4197389A (en) * 1977-07-18 1980-04-08 Hoechst Aktiengesellschaft Hardening agent for aqueous epoxy resin compositions
US4847360A (en) * 1987-03-02 1989-07-11 The Firestone Tire & Rubber Company Adhesive active finish for reinforcing members and related methods

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