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
  • D06M13/35—Heterocyclic compounds
  • D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings
  • D06M13/358—Triazines
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
  • C08J5/20—Manufacture of shaped structures of ion-exchange resins
  • C08J5/22—Films, membranes or diaphragms
  • C08J5/2206—Films, membranes or diaphragms based on organic and/or inorganic macromolecular compounds
  • C08J5/2218—Synthetic macromolecular compounds
• • 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
  • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
  • D06M15/423—Amino-aldehyde resins
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S260/00—Chemistry of carbon compounds
  • Y10S260/15—Antistatic agents not otherwise provided for
  • Y10S260/19—Non-high polymeric antistatic agents/n
  • Y10S260/20—Antistatic agent contains pentavalent nitrogen
• • 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
  • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
  • Y10S8/21—Nylon

Definitions

• R represents hydrogen or an alkyl group up to four carbon atoms, preferably -the-methylgroup
• R represents hydrogen or an ROCH2- group
• R and R represent alkyl groups individually or when taken together represent a saturated divalent aliphatic chain which forms a five.- 'to six-sided heterocycle with the nitrogen, as in morpholine, t'hiamorpholine, 3,5-dimethylrnorpholine, pyrrolidine, piperidine, or N- methylpiperazine
• R represents an aliphatic hydrocarbon group, including alkyl, *alkenyl, and ar-allgyl groups
• X represents an anion
• R and together may represent a propio'betaine radical, CH 2C H2 CO:6.
• Thes n w compounds have the property of imparting acharge or conducting layer on fibers, yarns, and fabrics treated therewith and apparently thus dissipate static charges or prevent the accumulationcf static .ch rge .therec
• These compounds might e expected to form insoluble resins- Yet they do not appear to ,do so. Rather theyappearto react with the fibers. At'least resinificationpi the compounds has not been iorced beyondthe water-soluble stage. Yet these novel-compounds-are sufliciently-retained .on yarns and fabrics after these are washed-to continue to-exert anti s tatic action.
• Various aminoacetoguauamiues are .lkJJOWD of the .formula 2,719,156 Patented Sept. 27, 1955 These are conveniently prepared by reacting together in the presence of an alkaline reagent dicyandiamide and a tert-aminoacetonitrile NGHzCN
• alkaline reagent dicyandiamide and a tert-aminoacetonitrile NGHzCN Such compounds are known in which 'R and R are alkyl, ara'lkyl, cycloalkyl, alkenyl, and phenyl.
• the two R groups may be the same or may be diiferent.
• the two R groups may also be part of a saturated divalent chain, such as --CH2CH2CH2CH2.
• aminoacetonitriles are formed in the same way as ,those from other secondary amines, such as dimethylamine, diethylamine, di'butylamjine, dodecylmethylamine, and the like. Secondary amine, formaldehyde, and hydrogen cyanide are brought together in any convenient order and reacted. "The tert-am'inoacetonitrile is collected as. a residue or is puritied'by a conventional step, such as distillation.
• an alkaline catalyst such as sodium or potassium hydroxide, benzyltrimethylammonium or dibenzyldimethylammo- ,nium hydroxide, choline, or a quaternary ammonium alkoxide, .such as choliue methoxide .or benzyltrimethylammonium butox'ide.
• a volatile, inert organic solvent may be used and the reaction accomplished by heating under reflux. The prod ct may be collected as a residue and purified byextraction, charcoaling, crystallizing, or similar conventional step. 7
• the tert-aminoacetoguanamine which is thus formed to reacted with ,an alkylating agent to form a quaternary amm iu al ypical yl ngagent includ methyl iodide, methyl bromide, ethyl bromide, ethyl chloride, methyl sulfate, .butyl bromide, octyl bromide, dodecyl bromide, ,cctadecyl bromide, .allyl chloride, methallyl chloride, crotyl chloride, idodecenyl chloride, benzyl chloride/or bromide, methylbenzyl chloride, butylbenzyl chloride, .octylbenzyl chloride, dodecylbenzyl chloride,
• nion not only h common halide or methyl sulfate ions, but also sulfate, acetate, formate, nitrate, phosphate, and other anions.
• Solvent is usually driven off from the reaction mixture to give a solid, which is essentially the desired quaternary ammonium salt.
• the lauryldimethylguanaminomethylammonium bromide has a phenol coeflicient of 85 against Micrococcus pyogenes, while substitution of the methyldodecylbenzyl group for the lauryl group gives a salt having a coefficient of 125.
• the quaternary salts are reacted with formaldehyde to give N-hydroxymethyl derivatives.
• the formaldehyde may be supplied from the usual aqueous formaldehyde solutions of commerce, from a revertible polymer, or from alcoholic solutions.
• One or both of the NH2 groups of the quaternary compound may be reacted and suflicient formaldehyde is supplied to accomplish the desired degree of methylolation.
• the methylolation reaction is best carried out at a pH between 7 and 10. Temperatures between 40 and 100 C. may be used.
• the reaction products are soluble, particularly in water.
• the solutions can be evaporated to give solid products which have the characterizing group NHCH2OH. From one to two such groups may be introduced. There is some evidence that more than two groups may be introduced on average.
• This group may be converted to an ether group by reacting the methylol derivatives with an alcohol. This is done by heating the methylol compound with an alcohol under acidic conditions, usually at a pH of to 3, most conveniently under reflux conditions with separation of water.
• the resulting ROCHzNI-I- derivative is obtained as a solution, from which it may be obtained as a solid by evaporating the solvent, usually here an excess of the alcohol used, such as methyl, ethyl, or butyl alcohol.
• Example 1 (a) A mixture of 55.4 parts of dimethylaminoacetonitrile, 50.4 parts of dicyandiamide, and 80 parts of isopropanol is stirred and heated under reflux (about 87 0.). Over a 45 minute period there are added to this mixture 32.3 parts of a 47% choline methoxide solution in methanol in 43.7 parts of isopropanol. The resulting mixture is stirred and heated under reflux for five hours. It is then cooled. The guanamine thus formed is filtered off and dried in an amount of 77 parts. It may be purified with charcoal in boiling water and recrystallized therefrom. It then melts at 235 -238 C.
• the compound thus prepared corresponds in composition to dimethylaminoacetoguanamine, which may be represented In the same way diethylaminoacetonitrile can be converted to diethylaminoacetoguanamine. Neither of these tert-aminoacetoguanamines is effective as an anti-static agent; nor are methylol derivatives thereof.
• This salt is sparingly soluble in water and is more soluble in aqueous dilute acid solutions. It is a white solid, melting at 251-253 C.
• a solution is prepared from 8.3 parts of the above benzyl chloride quaternary salt of dimethylaminoacetoguanamine in 12 parts of methanol. Thereto is added a solution of 3.1 parts of methyl hemiformal in 5 parts of methanol which has been adjusted to a pH of 8.5. The resulting mixture is heated under reflux for about an hour, at which time the solution has become homogeneous. It is then cooled and brought to a pH of 3.5 by adding dilute acid. The acid solution is heated under reflux for 20 minutes, is then cooled, is neutralized, and is evaporated to incipient precipitation. The concentrate is diluted with 70 parts of water to give a solution containing 14% of the dimethoxymethylated quaternary salt.
• Example 2 (a) A mixture of 40 parts of dimethylaminoacetoguanamine, 59 parts of dodecenyl chloride and 1000 par-ts of methanol isheated under reflux for five hours. The solution is then concentrated and cooled. There separates a white .so1idin..:an amount .Of .84 parts. It has a melting point of 249 C. and contains by analysis 9.62% of chlorine. It corresponds in composition to the dodecenyl chloride quaternary sallt of dimethylaminoguanamine. The theoreticalhchlorine content of this salt is 9.57%.
• This compound is converted to the methoxymethyl derivative by treating with methanol acidified to a pH of 3.5 and heating with toluen Ihiscompound is also efiective in dissipating electric charges on synthetic yarns and fabrics.
• the alkoxymethyl derivatives are formed by reacting the methylo'l compound as above on the acid side with an alkanol.
• Example 5 There are mixed 16.8 parts of dimethy-laminoacetoguanamine, 36.7 parts of -11-.octa d ecyl .bromidaand 317 parts of methanol. The mixture is heated under During this time the initial slurry becomes homogeneous and then deposits awhite -;S 0l:id. The reaction mixture is cooled .to-give a white, waxy solid, which is filtered off, washed with ether, and dried in a yield .of about 33 parts by weight. It contains by analysis 15.3% of bromineandcorresponds to the octadecyl bromide quaternary ammonium salt, for which the theoretical bromine ,content is 15.9%. The compound melts at 242-244 C.
• Example 6 (1a) A solutionof 2-3.5 parts of dimethylaminoaceto- --,g-uanamin e in 250 parts of water is added to 7.2 parts-of tB-propiolactone.
• Cellophane sheets were treated as above to give films having ion exchange action with a moderate degree of permselectivity.
• Example 7 (a) To a solution of 179 parts of morpholine in 174 parts of water are added 20 parts of concentrated hydrochloric acid, and then at 1520 C. 163 parts of a 37% solution of formaldehyde in water. Following this there is introduced 54 parts of anhydrous hydrogen cyanide at 1520 C. and the mixture stirred for two to three hours at 20 C. The resulting crystalline product is recrystallized from ethanol to yield 63 parts of morpholinoacetonitrile, melting at 59 61.5 C.
• N-cyanomethylpyrrolidine which is obtained as a liquid distilling at 80-83 C./ mm.
• pyrrolidinoacetoguanamine This can be used in exactly the same way as heretofore described to produce methylolated and methoxymethylated quaternary guanamine salts.
• R represents a member of the class consisting of alkyl, alkenyl of at least three carbon atoms, benzyl, and alkyl benzyl groups and jointly with X a propiobetaine radical, and X represents a salt-forming anion.
• a compound of the formula 7 A compound of the formula CH3 CHzCH C H3 N 0 0 C H2 ('1 N N HOCHzNH- C-NHCHzOH References Cited in the file of this patent UNITED STATES PATENTS West Dec. 30, 1947 Thurston Jan. 18, 1949

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• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Cited By (18)

Citations (2)

• 0
  • NL NL90411D patent/NL90411C/xx active
• 1953
  • 1953-12-04 US US396306A patent/US2719156A/en not_active Expired - Lifetime
• 1954
  • 1954-11-17 GB GB33271/54A patent/GB763323A/en not_active Expired
  • 1954-12-01 FR FR1117217D patent/FR1117217A/fr not_active Expired
  • 1954-12-02 DE DER15538A patent/DE1032259B/de active Pending

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