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
  • 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
  • D06M13/46—Compounds containing quaternary nitrogen atoms
  • D06M13/461—Quaternised amin-amides from polyamines or heterocyclic compounds or polyamino-acids
• • 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
• • H—ELECTRICITY
  • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
  • H05F—STATIC ELECTRICITY; NATURALLY-OCCURRING ELECTRICITY
  • H05F1/00—Preventing the formation of electrostatic charges
  • H05F1/02—Preventing the formation of electrostatic charges by surface treatment

Definitions

• R is an alkyl or alkaryl radical containing at least 7 carbon atoms
• X is hydrogen, methyl, or ethyl
• n is an integer from 1 to 10
• R and R are alkyl or hydroxy alkyl radicals of 1-3 carbon atoms
• R is a hydroxyalkyl radical of from 1-4 carbon atoms
• Y is an anion.
• antistatic agents are prepared by condensing an alkyl or aryl polyalkyleneoxy chlorocarbonate with a substituted alkyl diamine with subsequent acidification and alkoxylation to produce the quaternary compound, the chlorocarbonate being prepared by the reaction of the corresponding hydroxy compound with phosgene.
• the present invention relates to new and useful compositions of matter which function as antistatic agents when coated on synthetic and natural fibers, e.g., polyester fibers, acetate rayons, wool, polyolefins and the like, and to the method for their preparation. More particularly, the present invention relates to substituted carbamates exhibiting antistatic properties which are prepared by the condensation of alkyl and aryl polyalkyleneoxy chlorocarbonates with a substituted alkyl diamine followed by acidification and alkoxylation.
• antistatic agents function in two ways, both of which improve the electrical conductivity of the fiber surface.
• Such antistatic agents are either reasonably good conductors of electricity themselves, or they are hygroscopic and help concentrate atmospheric moisture on the fibers.
• antistatic agents fall into one of the following three categories: 1) polyhydroxy and polyethyleneoxy non-ionic compounds; (2) cationic, or neutral nitrogenous compounds with a hydrophobic moiety in their structure; (3) long-chain phosphates, phosphonates, or other oxygenated phosphorus derivatives. Additional types include sulfonated oils and ester emulsions, and other fiber lubricant emulsions which depend on the particular emulsifying agent used for their antistatic effect.
• Hygroscopic salts such as cyclohexylamine lactate
• polyethoxylated fatty acids and alcohols as antistatic agents for polypropylenes as well as fibers, is reported in U.S. 2,525,691.
• a further object of the present invention comprises antistatic agents of enhanced effectiveness, which antistatic agents contain an amide linkage and a polyalkoxylated hydrophobe.
• Yet a further object of the present invention comprises new and useful substituted carbamate antistatic agents derived from the chlorocarbonate of an alkoxylated primary or secondary alcohol or alkylphenol and a substituted alkyl diamine.
• Still a further object of the present invention comprises a process for preparing new and useful antistatic agents which process comprises condensing an alkyl or aryl polyalkylenoxy chlorocarbonate with an alkyl diamine followed by acidification and alkoxylation.
• the new and useful antistatic agents of the present invention correspond to the general formula:
• R is an alkyl or alkaryl radical containing at least 7 carbon atoms
• X is hydrogen, methyl, or ethyl
• n is an integer from 1 to 10;
• R and R are alkyl or hydroxyalkyl radicals of 1-3 carbon atoms
• R is a hydroxyalkyl radical of from 1-4 carbon atoms
• Y is an anion
• Exemplary alkyl or alkaryl radicals for R include: heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, hexadecyl, octadecly, nonadecyl, eicosyl, docosyl, pentacosyl, etc., methylphenyl, ethylphenyl, butylphenyl, hexylphenyl, octylphenyl, nonylphenyl, decylphenyl, dOdecylphenyl, petadecylphenyl, octadecylphenyl, nondecylphenyl, etc.
• Exemplary alkyl and hydroxyalkyl radicals for R and R include: methyl, ethyl, propyl, isopropyl, hydroxymethyl, hydroxyethyl, hydroxypropyl dihydroxypropyl, etc.
• Exemplary hydroxyalkyl radicals for R include; hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, dihydroxypropyl, dihydroxybutyl, etc.
• Exemplary anions for Y include: halides, chloride, bromide, iodide, phosphates, nitrates, sulfates, and the like.
• the new and useful antistatic agents of the present invention are prepared by condensing an alkyl or alkaryl polyalkylenoxy chlorocarbonate with a substituted alkyldiamine followed by acidification and alkoxylation.
• the alkyl or alkaryl polyalkylenoxy chlorocarbonate is prepared by reacting phosgene with a polyalkyleneoxylated aliphatic alcohol or alkylphenol under ambient conditions, in accordance with the following reaction:
• a substantially equivalent amount of the reactants is employed and the reaction is carried out by bubbling phosgene under the surface of the polyalkyleneoxylated aliphatic alcohol or alkylphenol until substantially all of the hydroxyl content of the reactants is converted into the chlorocarbonate as determined by infrared analysis or other suitable means.
• the polyalkyleneoxylated aliphatic alcohol or alkylphenol is prepared by any conventional procedure so as to incorporate 1 to moles of alkylene oxide, e.g., ethylene oxide, propylene oxide, or butylene oxide per mole of aliphatic alcohol or alkylphenol.
• alkyl or alkaryl polyalkyleneoxy chlorocarbonate prepared in Reaction I is further reacted with a substantialy equivalent amount of gamma dialkyl or dialkanol aminopropylamine to produce a substituted amide in accordance with the following reaction:
• the substituted amide produced in Reaction II is quaternized by reaction with an alkylene oxide or hydroxysubstituted alkylene oxide in the presence of an inorganic acid.
• Such a reaction is represented as follows:
• a commercial straight chain aliphatic alcohol admixture comprising approximately 5% C11, C12, C13, C14 and C15 is reacted with an alkylene oxide using an alkaline catalyst at C. and 13O p.s.i.g. until one to ten moles of the oxide is added.
• an alkaline catalyst In place of the alkaline catalyst, acidic catalysts such as BF H PO and the like can be used.
• Secondary alcohols such as Z-decanol, 3-decanol, 4-decanol, 3-dodecanol, -4-tetradecanol, fi-hexadecanol, and the like, or their admixtures as well as alkylphenols such as octylphenol, linear decyl phenol, branched dodecylphenol, etc., can be substituted for the primary aliphatic alcohol.
• alkyl or alkylarylpolyalkyleneoxyalkanol is then reacted with phosgene to form the corresponding alkyl or alkylarylpolyalkyleneoxy chlorocarbonate, and the latter compound converted to its carbamate by reaction with gamma dialkylaminopropylamine.
• This latter derivative is acidified and reacted with an alkylene oxide to form its quaternary ammonium salt.
• the new and useful antistatic agents of the present invention have been found to have unexpectedly advantageous antistatic properties, particularly when applied to synthetic fibers, such as polyesters, acrylics, polyolefins, polyamides, etc. Such antistatic agents have been found to reduce and maintain the electrostatic charges for extended periods of time below a potential of 3 kilovolts.
• EXAMPLE I (a) To a round bottom flask was charged a total of 288 parts by weight of an ethoxylate (av. app. 2.0 moles E0) of a C -C straight chain primary alcohol admixture calculated as a 209 mw. average and having the composition 5% C11, C12, C13, C14 and C15. The ethoxylate was agitated at ambient temperature (2030 C.) while phosgene was bubbled in under the surface over about 1.5 to 2.0 hours. Addition of phosgene was continued until examination of sample on IR showed essentially all absorption due to the hydroxyl group was eliminated. A total of 109 gms. phosgene (1.1 mole) were required.
• the swatches were conditioned at 72 F. and 50% relative humidity for at least 24 hours and the resistivity measured. Results were as follows:
• the products correspond, in general, to the formula -(d)
• the quaternary formed above was applied from MeOH/CCI (520 mls./ 1000 mls.) solvent mixture to Dacron and to cotton swatches at 1.25% application rate according to AATCC Standard Test Method 76-1959.
• the swatcthes were conditioned at 72 F. and 50% relative humidity for at least 24 hours and the resistivity measured. Results were as follows:
• the product was stripped to C. pot temperature under line vacuum and then filtered.
• the weight of the final product was 147 gms.
• the swatches were conditioned at 72 F. and 50% relative humidity for at least 24 hours and the resistivity measured. Results were as follows:
• EXAMPLE IV (a) To a round bottom flask was charged a total of 174 parts by weight of an ethoxylate (1.0 mole E0.) of octyl alcohol. The ethoxylate was agitated at ambient temperature (2030 C.) while phosgene was bubbled in under the surface over about 1.5 to 2.0 hours. Addition of phosgene was continued until examination of sample on IR showed essentially all absorption due to the hydroxyl group was eliminated. A total of 107 gms. phosgene (1.08 mole) were required.
• the product was stripped to 110 C. pot temperature under line vacuum and then filtered.
• the weight of the final product was gms.
• the product corresponded, in general, to the formula
• the swatches were conditioned at 72 F. and 50% relative humidity for at least 24 hours and the resistivity measured.
• Theoretical yield was mixture (520 mls. methanol/ 1000 mls. carbon tetrachloride) was then added by volume, i.e., 99 mls. and 97 mls., respectively, to produce soluble, fluid, clear solutions in each case.
• Preweighed and conditioned swatches (11x12 cms.). were immersed in the appropriate baths for one hour with good agitation. This agitation consisted of light shaking and swirling by hand. The swatches all appeared to wet nicely and uniformly. Removed swatches and allowed to drain back into bottle for about ten seconds, then hung under balance on a hook and adjusted to 100% pickup by lightly blotting with paper towels. All swatches were relatively easy to adjust to 100% pickup.
• R is a hydroxyalkyl radical having from 1 to 4 carbon
• Samples of the product of Example III were submitted Y riltoms; i for resistivity measurements.
• the first sample was ap- IS an q proximately 60% active in the mixture of isopropanol Anantlstatlc compound of the formula and water in which it was prepared while solvents had CH3 the SBCOI'ld sample, and ll.
• R is a radical selected from alkyl and alkyaryl radicals 117 138.8, 139.5; 260-75, 93.7, 94.9
• X is selected from hydrogen, methyl or ethyl
• n is a number from 1 to 10;
• R and R are selected from alkyl and hydroxyl alkyl radicals having from 1 to 3 carbon atoms;

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• Chemical & Material Sciences (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Organic Chemistry (AREA)
• Textile Engineering (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

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Cited By (15)

Citations (4)

• 1967
  • 1967-04-03 US US627859A patent/US3454625A/en not_active Expired - Lifetime
• 1968
  • 1968-03-26 CH CH452368A patent/CH483400A/de not_active IP Right Cessation
  • 1968-03-26 CH CH1232369D patent/CH1232369A4/xx unknown
  • 1968-03-26 CH CH1232369A patent/CH511972A/de not_active IP Right Cessation
  • 1968-03-27 DE DE19681768060 patent/DE1768060A1/de active Pending
  • 1968-03-29 FR FR1561574D patent/FR1561574A/fr not_active Expired
  • 1968-03-29 GB GB05358/68A patent/GB1219931A/en not_active Expired
  • 1968-04-02 BE BE713109D patent/BE713109A/xx unknown

Patent Citations (4)

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