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
  • D06M13/10—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 oxygen
  • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
  • D06M13/188—Monocarboxylic acids; Anhydrides, halides or salts thereof
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
  • C07F5/06—Aluminium compounds
  • C07F5/069—Aluminium compounds without C-aluminium linkages
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
  • C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
  • C07F9/02—Phosphorus compounds
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
  • C07F9/02—Phosphorus compounds
  • C07F9/06—Phosphorus compounds without P—C bonds
• • 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
  • D06M13/10—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 oxygen
  • D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
• • 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
  • D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
  • D06M13/503—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms without bond between a carbon atom and a metal or a boron, silicon, selenium or tellurium atom
• • 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

Definitions

• the waterproofing effect has been achieved it is not resistant to, or at least has very poor resistance to, drycleaning hence the necessity to subject the cleaned article to a subsequent reproofing.
• This treatment may be effected by means of the ordinary commercial waterproofing substances, such as those based on emulsions of paraffin wax, stearoylaminomethyl-pyridinium chloride, stearylhydroxymethyl-pyridinium chloride or chromium stearato-chloride.
• These products must be applied from an aqueous bath.
• the reason for cleaning with solvents is in fact to avoid all manipulation of the clothes in an aqueous medium, which may be harmful to their appearance and cause felting or shrinking, making them finally unusable. It is therefore of importance to make available to dyers and cleaners waterproofing substances which are soluble in the solvents which they use such as, for example trichloroethylene, perchlorethylene, white spirit, or dry cleaning solvent.
• organic derivatives of the metals of Groups III or IV which may be in the form of salts of aliphatic acids of high molecular weight, in the form of alcoholates of lower aliphatic alcohols, or in the form of products resulting from the action of aliphatic acids of high molecular weight on these alcoholates.
• Waterproofing products obtained-from alcoholates of polyvalent metals and phosphoric esters, in particular, have been described, and intended more especially for the waterproofing of leather.
• waterproofing products having an excellent solubility in all the solvents used for drycleaning and giving an excellent waterproofing effect without 3,454,420 Patented July 8, 1969 alteration of the appearance of the treated articles, can be obtained by reacting an acid halide which contains a hydrocarbon chain with 14 to 22 inclusive carbon atoms with an alcoholate of a metal of Group III or IV of the Periodic Classification at high temperature.
• acid halide which may be used to carry out the invention are the chlorides of aliphatic carboxylic acids in which the hydrocarbon chain contains 14 to 22 carbon atoms, such as the higher fatty acids of natural origin, the acids resulting from the oxidation of parafiins or 0x0 aldehydes, or Koch acids, or the chlorides of alkylsulphonic acids resulting from the sulphochlorination of parafiins and containing 14 to 22 carbon atoms, or the chlorides of phosphoric acid in which one or two acid groups have been esterified by aliphatic alcohols with a hydrocarbon chain containing 14 to 22 carbon atoms, such as the fatty alcohols of natural origin or the 0x0 alcohols, or the chlorocarbonates of these same alcohols.
• metal alcoholates which may be used are the alcoholates of aluminum, zirconium or titanium, in which the alcoholic radicals are those of ethyl, isopropyl, propyl, normal butyl, isobutyl, 2-ethylhexyl, lauryl or 0x0 alcohols.
• a solution of a metal alcoholate in an inert solvent such as for example toluene, is slowly added at low temperature, for example below 50 C., to a solution in the same inert solvent of the acid halide.
• the amount of metal alcoholate added is such that it corresponds to one molecular equivalent per atomic equivalent of halogen present in the acid halide.
• the solvent is driven off by distillation.
• the mass remaining is then heated with agitation at a temperature between C. and 160 C., preferably between C. and C.
• the waterproofing products thus obtained are soluble in trichlorethylene, perchlorethylene, white spirit, and drycleaning solvent. Their solutions in these solvents enable textile materials to be made waterproof or their waterproof properties to be preserved if they already possess them. These solutions may also be used for the waterproofing of other fibrous materials such as leather.
• EXAMPLE 1 151.25 parts of stearoyl chloride and 125 parts by volume of toluene are introduced into an apparatus fitted with a mechanical stirrer, a thermometer, a gauge, and a plunging tube. 102 parts of aluminum isopropylate in solution in 125 parts by volume of toluene are added by means of the gauge in a period of 4 hours. During this addition the temperature of the mass rises from 24 C. to 40 C. When the introduction is completed, the toluene is distilled 3 off under reduced pressure, the temperature of the mass being maintained at 40 C.
• a Dean-Stark separating tube is fitted on the apparatus.
• the exit of the condenser is connected to tubes or flasks plunged into carbon dioxide snow.
• a stream of nitrogen is passed into the mass by means of the plunging tube and the mass is heated to 145- 150 C.
• a colourless liquid distils over and is collected in the Dean-Stark tube and in the tubes or flasks plunged in the carbon dioxide snow. 47 parts of a liquid containing isopropyl chloride, isopropyl ether and isopropanol are obtained. Then the distillation ceases, the heating is interrupted, and the mass is allowed to cool under a stream of nitrogen.
• the residue consists of 206 parts of a very thick brown liquid containing 6.46% of Cl and 6.30% of Al.
• the product thus obtained is excellently soluble in chlorinated solvents and aliphatic hydrocarbons, and its solutions give waerproof properties to fabrics.
• EXAMPLE 2 The operation is as in Example 1, but the 102 parts of aluminium isopropylate are replaced by 170 parts of titanium tetrabutylate. 275 parts of a very thick brown product of resinous consistency, containing 4.72% of Cl and 8.70% of Ti, are obtained. It is excellently soluble in all the solvents customarily used for drycleaning Its solutions give excellent waterproof properties to clothes.
• EXAMPLE 3 399 parts of stearyl dichlorophosphate (dichlorophosphate of technical stearyl alcohol) and 500 parts by volume of toluene are introduced into an apparatus fitted with a mechanical stirrer, a thermometer, a gauge, a plunging tube and a reflux condenser. 408 parts of aluminum isopropylate in solution in 700 parts by volume of toluene are added by means of the gauge in a period of 4 hours. The temperature of the mass rises from 20 C. to 55 C. After this introduction, the toluene is driven off by distilling under reduced pressure, the mass being heated to 40 C.
• a Dean-Stark separating tube is fitted on the apparatus and the outlet of the condenser is connected to bubblers plunged into the carbon dioxide snow.
• a stream of nitrogen is passed into the mass by means of the plunging tube and the temperature is raised to 155 C.
• a colourless liquid begins to distil and is collected in the Dean-Stark tube and in the bubblers. Heating is continued until all distillation ceases. 107 parts of this colourless liquid are thus obtained, which on analysis is found to be composed of isopropyl chloride, isopropyl other and isopropanol.
• EXAMPLE 4 620.5 parts of octadecyl chlorophosphate and 700 parts by volume of toluene are introduced into an apparatus identical with that of Example 3. 204 parts of aluminum isopropylate in solution in 350 parts by volume of toluene are added by means of the gauge in a period of 4 hours. The operation is carried out in the same -way as that of Example 3. 770 parts of a brown, very thick, resinous product are obtained, which is excellently soluble in the solvents used for drycleaning and contains 2.30% of Cl, 4.02% of P and 3.50% of Al.
• EXAMPLE 5 399 parts of stearyl dichlorophosphate and 500 parts by volume of toluene are introduced into an apparatus fitted with a mechanical stirrer, a thermometer, a plung ing tube, and a gauge. A solution of 542 parts of zirconium tetraethylate in 700 parts by volume of toluene 4 is introduced by means of the gauge in ac period of 4 hours. The operation is finished by the method described in Example 3. 830 parts of a dark, resinous, very thick product, soluble in the solvents used for drycleaning and containing 3.73% of P, 4.2% of Cl and 10.80% of Zr, are obtained.
• EXAMPLE 6 A piece of cotton satin weighing 300 g./m. is treated in a bath of perchlorethylene containing 30 g. per litre of the waterproofing product of Example 1. After drying and returning to the usual atmospheric humidity, the fabric possesses excellent waterproof properties characterised by a Schmerber figure equal to 350 and a spraytest equal to 100.
• EXAMPLE 7 A piece of cotton satin weighing 300 g./m. is treated in a bath of white spirit containging 10 g. per litre of the waterproofing product described in Example 4 and 30 g. per litre of parafiin wax having a melting point between 54 C. and 58 C. After draining, drying and taking up the usual atmospheric humidity, the fabric possesses. waterproof properties characterised by a Schmerber figure equal to 365 and a spray test equal to 100.
• EXAMPLE 9 A piece of calico weighing about g./m. is impregnated in a bath of perchlorethylene containing 30 g. per litre of the Waterproofing product described in Example 3. After drying and taking up the usual atmospheric humidity, the calico is excellently waterproof. It possesses a Schmerber figure equal to 203 and a spray test equal to 100.
• said acid halide is a member selected from the group consisting of 5 6
• 117-1355 (-b) a chloride of phosphoric acid in which one or two acid groups have been esterified by an aliphatic alco- 5 hol having a hydrocarbon chain of from 14 to 22 WILLI AM D. M ARTIN, Primary Examiner.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Textile Engineering (AREA)
• Engineering & Computer Science (AREA)
• Biochemistry (AREA)
• Molecular Biology (AREA)
• General Health & Medical Sciences (AREA)
• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Inorganic Chemistry (AREA)
• Detergent Compositions (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

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• 0
  • NL NL130313D patent/NL130313C/xx active
• 1965
  • 1965-01-12 FR FR1570A patent/FR1447178A/fr not_active Expired
  • 1965-12-20 CH CH1752665A patent/CH445485A/fr unknown
  • 1965-12-21 DE DEE30707A patent/DE1291730B/de active Pending
  • 1965-12-27 BE BE674373D patent/BE674373A/xx unknown
  • 1965-12-29 NL NL6517112A patent/NL6517112A/xx unknown
• 1966
  • 1966-01-05 US US3454420D patent/US3454420A/en not_active Expired - Lifetime
  • 1966-01-10 GB GB105366A patent/GB1089576A/en not_active Expired
  • 1966-01-10 SE SE27766A patent/SE313289B/xx unknown
  • 1966-01-11 NO NO161204A patent/NO123523B/no unknown
  • 1966-01-12 DK DK14666A patent/DK111263B/da unknown

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