Classifications

• • C—CHEMISTRY; METALLURGY
  • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
  • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
  • C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
  • C04B41/80—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone of only ceramics
  • C04B41/81—Coating or impregnation
  • C04B41/82—Coating or impregnation with organic materials
• • C—CHEMISTRY; METALLURGY
  • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
  • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
  • C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
  • C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
  • C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
  • C04B41/466—Halogenated compounds, e.g. perfluor-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
  • C07F9/08—Esters of oxyacids of phosphorus
  • C07F9/09—Esters of phosphoric acids
  • C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
  • C11D1/004—Surface-active compounds containing F
  • C11D1/006—Surface-active compounds containing fluorine and phosphorus
• • 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
  • D06M13/244—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
  • D06M13/298—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof containing halogen atoms
• • 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
  • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters 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
  • D21H17/10—Phosphorus-containing compounds
• • 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
  • D21H17/11—Halides

Definitions

• This invention relates to novel processes for rendering solid materials oil-repellent and to the novel materials thus produced.
• solid materials herinabove I mean water-insoluble materials customarily employed in the manufacture of articles of utility, for instance textile fabric, textile yarns, leather, paper, plastic sheeting, wood, ceramic clays, as well as manufactured articles prepared therefrom such as articles of apparel, wall paper, paper bags, cardboard boxes, porous earthenware, etc.
• oil repellency for the purpose of definiteness, I shall refer hereinafter to the quality of repelling, under the standard tests herein discussed, a light mineral oil such as a commercial liquid hydrocarbon or a vegetable oil such as peanut oil.
• the materials treated according to this invention are found to possess repellency to oils, greases and fats generally, regardless of their origin (as for instance, mineral, vegetable or animal kingdom) or their consistency.
• Oil-repellency in articles such as wearing apparel, cardboard boxes, paper bags or wrapping paper is a relatively young and not fully developed art.
• the demand for such articles is perhaps old enough.
• the advantages of having for instance grease-repellent overalls for mechanics, wallpaper that does not stain easily, oil-repellent paper bags for bakery goods, oron the contrary-containers which will keep the contents safe against contamination with greasy soil from the outside, are so obvious as not to require much elaboration. Hitherto, however, the solution to this problem has not been entirely satisfactory from the economical viewpoint.
• Some of the oil-repellency agents hitherto used or suggested are complicated and costly chemicals. Others can be applied only from an organic solvent. Still others are relatively inefiicient and require application of large quantities thereof with respect to the weight of the fiber or solid material being treated therewith.
• water-solubilizing cations in the definition of Z above may be mentioned the alkali-metals (Na, K, Li), ammonium, diethanolammonium, triethanolammonium, morpholinium, and the like.
• the compounds defined have also the quality of versatility, being applicable to a wide variety of textile fibers, including cotton, viscose, cellulose acetate, Wool, silk, nylon, acrylic fiber and polyester fiber. They are also applicable to leather, paper, wood and unglazed earthenware.
• Example 1 100 parts of cotton fabric are dipped into an aqueous bath containing 1000 or more parts of water and 1 part by Weight (i.e. 1%'O.W.F.) of ammonium bis(lH,lH,9H- hexadecafluorononyl) phosphate. After agitating in said bath for 5 minutes or more, the fabric is removed, squeezed and air-dried.
• aqueous bath containing 1000 or more parts of water and 1 part by Weight (i.e. 1%'O.W.F.) of ammonium bis(lH,lH,9H- hexadecafluorononyl) phosphate.
• oil-repellency ratings of 50 were obtained on all fabrics above mentioned.
• the same set of experiments is repeated except for increasing the concentration of the polyfluoroalkyl phosphate to 2% O.W.F., ratings as high as 80 are obtained.
• Example 2 Following the procedure of Example 1, cotton muslin was impregnated with an aqueous bath containing a quantity of ammonium 1H,lH,llH-eicosafluoroundecyl phosphate corresponding in weight to 4% of the weight of the fabric. Upon drying, the fabric was found to have an oil rating of 70 by the standard test above described.
• Example 3 Unsized paper was treated according to the procedure set forth in Example 1, but using as oil-repellency agent an essentially 50:50 mixture (by weight) of monoand 'bis-polyfluoroalkyl phosphates obtained by reacting with phosphorus pentoxide in toluene (according to second part of Example IV of Banning, U.S.P. 2,597,702) upon a mixture of polyfluoroalcohols comprising 50 mole percent 1H,lH,5H-octafluoro-l-pentanol, 33% 'lH,1H,7H-
• dodecafluoro-l-heptanol and 17% lH,1H,9H-hexadeca-V solution of any other convenient concentration.
• preparation of the aqueous solution of the polyfluoroalkyl phosphates may be facilitated by first dissolving the agent in an organic solvent, such as acetone,
• methanol, or ethanol, followed by dilution with water, or a a solution of the free acid phosphate in an organic solvent as aforenoted may be diluted With an aqueous amine or ammonia solution.
• the quantity of the phosphate agent added may vary from 0.05 to 10% O.W.F. The optimum amount will depend upon such factors as the nature of the material being treated, the composition of the phosphate, and the degree of oil-repellency desired.
• the ammonium salts or amine-addition products of the phosphates are more elfective than the free phosphoric acid, and the wF-compounds (Formula -I) are more potent than the UH-compounds (Formula II).
• the bis-fluoroa-lkyl phosphates are enormous more eflective than the mono compounds, and where mixtures are unavoidable, it is preferred to use such mixtures wherein the bis-fiuoroalkyl compounds predominate (i.e. vy has an average value greater than 1.5).
• the wF-cornpounds may be generically referred to as (perfluoroalkyl-methyl) phosphates. It follows from the aforegoing discussion that the most p tent compounds for the purposes of this invention, and therefore the most desirable from the pr-atioal viewpoint, are the bis(perfluoroalkyl-methyl)ammonium phosphates.
• the wF-compounds possess the added advantage that they also impart water-repellence to the treated articles.
• oil-repellent solid articles has been stressed throughout the above discussion as being the primary object of this invention, the process and means herein described, when wF polyfiuoroalkyl phosphates are employed, produce both oil-repe lence and water-repellence on the article treated therewith, be it textile fiber, paper or any other water-insoluble, solid material.
• polyfiuoroalkyl phosphate selected is a mixed product in which the dominant component is a compound whose y-value is 2.
• phosphate selected is a bis(perfiuoroalkyl-methyl)ammonium phosphate.
• phosphate selected is ammonium bis(1H,lH-pentadecafluorooctyl) phosphate.

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• Chemical & Material Sciences (AREA)
• Engineering & Computer Science (AREA)
• Organic Chemistry (AREA)
• Ceramic Engineering (AREA)
• Textile Engineering (AREA)
• Materials Engineering (AREA)
• Life Sciences & Earth Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Structural Engineering (AREA)
• General Health & Medical Sciences (AREA)
• Molecular Biology (AREA)
• Health & Medical Sciences (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Wood Science & Technology (AREA)
• Biochemistry (AREA)
• Paper (AREA)
• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

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Cited By (19)

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• 1960
  • 1960-09-06 US US53885A patent/US3096207A/en not_active Expired - Lifetime
  • 1960-09-06 US US53884A patent/US3112241A/en not_active Expired - Lifetime
• 1961
  • 1961-08-30 FI FI1530/61A patent/FI40279B/fi active
  • 1961-09-05 DE DEP27822A patent/DE1260059B/de active Pending
  • 1961-09-06 FR FR872469A patent/FR1305612A/fr not_active Expired
  • 1961-09-06 GB GB31993/61A patent/GB939902A/en not_active Expired

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