Classifications

• • C—CHEMISTRY; METALLURGY
  • C14—SKINS; HIDES; PELTS; LEATHER
  • C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
  • C14C9/00—Impregnating leather for preserving, waterproofing, making resistant to heat or similar purposes
• • 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
  • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
  • D06M11/68—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with phosphorus or compounds thereof, e.g. with chlorophosphonic acid or salts thereof
  • D06M11/70—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with phosphorus or compounds thereof, e.g. with chlorophosphonic acid or salts thereof with oxides of phosphorus; with hypophosphorous, phosphorous or phosphoric acids or their salts
  • D06M11/71—Salts of phosphoric acids
• • 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
  • D06M13/02—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with hydrocarbons
• • 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
  • D06M13/244—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 sulfur or phosphorus
  • D06M13/282—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 sulfur or phosphorus with compounds containing phosphorus
  • D06M13/288—Phosphonic or phosphonous acids or derivatives thereof
• • 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
  • D06M13/244—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 sulfur or phosphorus
  • D06M13/282—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 sulfur or phosphorus with compounds containing phosphorus
  • D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
• • 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
• • 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
  • D06M13/51—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond
• • 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
  • D06M19/00—Treatment of feathers
• • 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
  • D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
  • D06M23/10—Processes in which the treating agent is dissolved or dispersed in organic solvents; Processes for the recovery of organic solvents thereof
• • D—TEXTILES; PAPER
  • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
  • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
  • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
  • D21H17/03—Non-macromolecular organic compounds
  • D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
  • D21H17/12—Organo-metallic compounds

Definitions

• This invention relates to a process for waterproofing fibrous materials, and more particularly to a method of imparting Water-repellent properties to fibrous materials with the aid of condensation products formed from metal alcoholates and acid high-molecular organic derivatives of phosphoric acid.
• the waterproofingagent used in accordance with the present invention primarily aluminum alcoholates, such as aluminum isop-ropylate, aluminum. butylate, aluminum octylate, aluminum -dodecylate, or alcoh'olates of other, preferably low-molecular, organic hydroxyl compounds, the alkyl radicals of which mayalso comprise substituents, such as halogen, may be used as starting materials.
• aluminum alcoholates such as aluminum isop-ropylate, aluminum. butylate, aluminum octylate, aluminum -dodecylate, or alcoh'olates of other, preferably low-molecular, organic hydroxyl compounds, the alkyl radicals of which mayalso comprise substituents, such as halogen, may be used as starting materials.
• Phosphoric acid esters of organic hydroxyl compounds suitable for the production of the condensation products used as waterproofing agents in accordance with the presentinvention are primarily the corresponding monoalkyl esters with-alkyl radicals having at least 6 carbon atoms in the alkyl chain, such as phosphoric acid monooctyl ester, phosphoric acid monododecyl ester, phosphoric acid monooleyl ester, as well as phosphoric acid monoalkylphenol esters wherein the alkyl radicals have from 3 to 18 carbon atoms, phosphoric acid mononaphthenyl ester, phosphoric acid monoabietyl ester, and the like.
• the corresponding di-esters, inadmixture with mono esters may be used, as well as. those'esters the alcohol radicals of which carry substituentsor' are'interrupted by oxygen, sulfur or nitrogen atoms or by groups containing oxygen, sulfur and/or nitrogen.
• the acid phosphoric acid esters also other high;- molecular organic derivatives of phosphoric acids maybe used, such as the corresponding acid phosphoric acid alkyl amides, alkyl phosphonic acids, alkyl phosphinic acids, and the like. 1
• condensation products are formed in the presence of inert organic solvents, such as isopropanol, trichloroethylene or toluene, as well as other low-molecular alcohols, aliphatic halogenated hydrocarbons or aromatic hydrocarbons.
• inert organic solvents such as isopropanol, trichloroethylene or toluene
• other low-molecular alcohols such as aliphatic halogenated hydrocarbons or aromatic hydrocarbons.
• condensation products which contain, for example, polyvalent metal monohydroxy alcoholates and phosphoric acid monoalkyl in diiferent molecular proportions;- is accomplished by combining solutions of the starting components in the above solvents and thereafter heating the resulting mixture for a short time, if'necessary, to temperatures between 30 and 50 C.
• the starting components are used in a molar ratio of alcoholate to phosphoric acid ester from 1E0.5 to 1:1.5, but other molar ratios may also be used.
• solutions of the starting materials in the solvents may also be used for direct application to the fibrous material.
• the solvents may also be distilled off and the residue may be dissolved in other suitable media which are customarily used toproduce impregnations on fibrous'materials, such as vegetable, animal or mineral oils, fats or waxes.
• hydrocarboxylic 'acid esters 'compounds with reactive methylene groups, hydroxy-oxo compounds which are capable of being arranged into anacidic form, such as acetylacetone and acetoacetic acid ester, as well as oximes and ⁇ so forth.
• the present invention is particularly well adapted for the production of water-repellent impregnations on textile materials in the form of fibers, flakes, threads, ribbons, woven fabrics, knitted fabrics made of natural or synthetic fiber materials, especially rayon, spun rayon,
• fibers such as polyamide and polyester fibers, V polyacrylicester and polyacrylic-nitrile fibers, polyvinylchloride fibers, alignate fibers,'glass fibers, and the like.
• fibrous-materials such as, paper,*cardboard, cellulose, wood pulp, wood, and the like, may be rendered water-repellent with the aid of the waterproofing agents described herein.
• Non-fibrous materials may also be rendered water-repellent therewith.
• Non-fibrous materials to which the waterproofing agents may advantageously be applied include the surfaces of plastics, painted surfaces, metal surfaces, and so forth.
• ceramic materials and other porous building materials may also be rendered waterproof by impregnation with the condensation products or solutions described above.
• the process according to the present invention may advantageously be practiced by immersing the materials to be waterproofed in solutions which contain about 0.5 to 5.0%, preferably from 2 to 3%, by weight of-the above-described condensation product or mixtures thereof, or by brushing, and especially by spraying, such materials with these solutions.
• solutions which contain about 0.5 to 5.0%, preferably from 2 to 3%, by weight of-the above-described condensation product or mixtures thereof, or by brushing, and especially by spraying, such materials with these solutions.
• various hydrophobic effects may be obtained, such as water-repellent effects, water-resistance or water-impermeability.
• the fibrous materials are preferably subjected to the impregnation in the dry state. After the impregnation with the waterproofing agents, the fibrous material is advantageously heated for a short period of time, if necessary in the presence of moisture, for example with the aid of steam, whereby the waterproofing effects are still further improved.
• the waterproofing agents used in the examples below were produced by first dissolving the metal alcoholates in an organic solvent, such as in trichloroethylene or benzene, and thereafter stirring a solution of the high molecular acid phosphoric acid alkyl ester in an identical or similar solvent into the metal alcoholate solution. After the two solutions were combined, the solution mixture was heated for a short period of time, for example from 3 to 6 minutes. The solution mixture was then ready for use in the impregnation step. It may, however, also be admixed with small amounts of a stabilizing agent. The solution mixture was used in the resulting concentration or in a more diluted state, which was achieved by merely adding more of the respective solvent.
• an organic solvent such as in trichloroethylene or benzene
• Example 1 A ribbon of acetate rayon was immersed into a gasoline solution which contained 50 gm./liter of liquid wax having a melting point of 45 C., 2 gm./liter acetylacetone and 50 gm./liter of a condensation product formed by aluminum isopropylate and acid monophosphoric acid ester mixture of technical-grade fatty alcohols having from 12 to 18 carbon atoms in the molecule.
• the condensation product was a mixture of compounds having the structural formulas CnHaau O wherein n is an integer from 12 to 18, inclusive.
• the acetate rayon ribbon was centrifuged until the 4 increase in weight was about 25%, and then dried at 100 C.
• the dry ribbon exhibited an excellent waterrepellent effect, a soft, pleasant feel and also good antistatic properties.
• Example ll Raincoats made of cotton poplin were immersed for 5 minutes into a stationary carbon tetrachloride solution which contained 10 gm./ liter soft parafiin having a melting point of 38 to 40 C., 10 gm./liter of a condensation product formed from 1 mol aluminum isopropylate and 0.7 mol of an acid monoalkylphosphate mixture, the alkyl radicals of which contained from 16 to 18 carbon atoms, and-l gm./liter acetylacetone.
• the condensation product was a mixture of compounds having the structural formulas and P ⁇ /AI.OC:H1 nHInHO 0 wherein n is an integer from 16 to 18, inclusive.
• the intpregnated raincoats were centrifuged until the weight increase was about and thereafter dried at 60 to 80 C.
• the impregnated, dry coats had a pleasant feel and exhibited good water-repellent properties after ironing or steam-pressing.
• Example III After impregnation, the nettle fabric was centrifuged and dried in the usual manner. The dry fabric exhibited good water-repellent properties.
• Example IV Perlon fabric was immersed into a carbon tetrachloride solution which contained 20 gm./liter of a condensation product produced from 1 mol aluminum isopropylate and 2.5 mols of an acid monoalkylphosphate mixture, the alkyl radicals of which contained from 8 to 18 carbon atoms.
• the condensation product was a mixture of compounds having the structural formulas shown in Examples I and vIIabove, except that n was an integer from 8 to 18, inclusive; After impregnation of the Perlon fabric, it was centrifuged until its weight increase was about 50%, and thereafter dried at 80 C.
• the dry, impregnated fabric had a soft feel, exhibited good water-repellent properties and, in addition, antistatic properties. r
• Example V Wooden objects were brushed with a trichloroethylene solution which contained 20 gm./liter of hard parafiin and 20 gm./liter of the condensation product described in Example I above formed from aluminum isopropylate and an acid phosphoric acid monoalkyl ester mixture. The wooden objects were then air-dried, whereupon they exhibited excellent water-repellent properties.
• the waterproofing impregnation may also be combined with other customary wood impregnations, for example with impregnations against rotting and the like.
• Example VI Paper or cardboard webs were impregnated with a gasoline solution containing 5 gm./liter of the condensation product described in Example I above, either by spraying or by immersion. Thereafter the fibrous material was dried in the customary fashion, whereupon it exhibited excellent water-repellent properties.
• Example VII structural formulas cm aro and O CsH'l OCaH1
• the impregnated felt materials were squeeze-dried and then fully dried by heating.
• the dry, impregnated felt material exhibited excellent Water-repellent properties.
• Example VIII Woolen overcoat cloth was immersed into a trichloroethylene solution which contained gm./liter of the condensation product formed by 1 mol titanium isopropylate and 1.3 mols of the acid monophosphoric acid ester mixture of technical-grade fatty alcohols having from 12 to 18 carbon atoms in the molecule, as well as 10' gm./
• the condensation product was a mixture of compounds having the structural formulas wherein n is an integer from 12 to 18, inclusive. After squeeze-drying and then air-drying the woolen fabric, it
• the process of waterproofing fibrous materials which comprises impregnating said fibrous materials with a condensation product formed by a condensation reaction between (A) alcoholates of polyvalent metals selected from the group consisting of aluminum, magnesium, titanium and zirconium and (B) diacid phosphoric acid mono-esters of high molecular-weight organic hydroxyl compounds containing at least 6 carbon atoms, said alcoholates and said monoesters being present in a molar ratio of from 1:05 to 1:1.5, said condensation product being in solution in an inert organic solvent, and evaporating the solvent.
• A alcoholates of polyvalent metals selected from the group consisting of aluminum, magnesium, titanium and zirconium
• B diacid phosphoric acid mono-esters of high molecular-weight organic hydroxyl compounds containing at least 6 carbon atoms
• the process of waterproofing fibrous materials which comprises impregnating said fibrous materials with a condensation product formed by a condensation reac-v tion between (A) alcoholates of polyvalent metals selected from the group consisting of aluminum, magnesium, titanium and zirconium and (B) diacid phosphoric acid mono-esters of high molecular-weight organic hydroxyl compounds containing at least 6, carbon atoms, said alcoholates and said monoesters being present in a molar ratio of from 1:05 to 1215, said condensation product being in solution in an inert organic solvent, said solution also comprising an organic complex-stabilizing atoms, evaporating the solvent and drying compound, and evaporating the solvent.
• Theprocess of waterproofing fibrous materials which comprises impregnating said fibrous materialswith a solution mixture consisting of a solution of an (A) alcoholate of a polyvalent metal selected from the group consisting of aluminum, magnesium, titanium andzirconium in an inert organic solvent and (B) a solution of diacid phosphoric acid mono-esters of high molecularweight organic hydroxyl compounds containing at least 6 carbon atoms in an inert organic silvent, said alcoholate and said monoesters being present ina molar ratio of from 1:05 to 151.5, and drying the impregnated fibrou material at elevated temperatures.
• A alcoholate of a polyvalent metal selected from the group consisting of aluminum, magnesium, titanium andzirconium in an inert organic solvent
• B a solution of diacid phosphoric acid mono-esters of high molecularweight organic hydroxyl compounds containing at least 6 carbon atoms in an inert organic silvent

Landscapes

• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Inorganic Chemistry (AREA)
• Dispersion Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
• Treatment And Processing Of Natural Fur Or Leather (AREA)

Applications Claiming Priority (2)

Publications (1)

Family

ID=25965145

Family Applications (1)

Country Status (7)

Cited By (5)

Families Citing this family (6)

Citations (3)

Family Cites Families (2)

• 0
  • BE BE555393D patent/BE555393A/xx unknown
  • NL NL106507D patent/NL106507C/xx active
• 1956
  • 1956-05-14 DE DEB40231A patent/DE1061478B/de active Pending
  • 1956-06-15 DE DEB40684A patent/DE1176302B/de active Pending
• 1957
  • 1957-02-15 CH CH356353D patent/CH356353A/de unknown
  • 1957-04-29 FR FR1174389D patent/FR1174389A/fr not_active Expired
  • 1957-06-11 US US664897A patent/US2977249A/en not_active Expired - Lifetime
  • 1957-06-12 GB GB18475/57A patent/GB835797A/en not_active Expired

Patent Citations (3)

Also Published As

Similar Documents