US3408319A - Tanning compositions comprising aqueous solutions of unsaturated acid-unsaturated sulfated oil copolymers - Google Patents

Tanning compositions comprising aqueous solutions of unsaturated acid-unsaturated sulfated oil copolymers Download PDF

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Publication number
US3408319A
US3408319A US416874A US41687464A US3408319A US 3408319 A US3408319 A US 3408319A US 416874 A US416874 A US 416874A US 41687464 A US41687464 A US 41687464A US 3408319 A US3408319 A US 3408319A
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United States
Prior art keywords
weight
oil
solution
unsaturated
tanning
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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US416874A
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English (en)
Inventor
William J Rau
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rohm and Haas Co
Original Assignee
Rohm and Haas Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Rohm and Haas Co filed Critical Rohm and Haas Co
Priority to US416874A priority Critical patent/US3408319A/en
Priority to DE1494858A priority patent/DE1494858C3/de
Priority to BE672851D priority patent/BE672851A/xx
Priority to FR39837A priority patent/FR1457045A/fr
Priority to NL656515574A priority patent/NL148069B/xx
Priority to ES0320165A priority patent/ES320165A1/es
Priority to FI2915/65A priority patent/FI44484B/fi
Priority to GB51248/65A priority patent/GB1111868A/en
Priority to NO65160776A priority patent/NO122765B/no
Priority to BR175485/65A priority patent/BR6575485D0/pt
Priority to DK629765AA priority patent/DK111969B/da
Priority to IL24749A priority patent/IL24749A/xx
Priority to SE15893/65A priority patent/SE317503B/xx
Application granted granted Critical
Publication of US3408319A publication Critical patent/US3408319A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C14C3/00—Tanning; Compositions for tanning
    • C14C3/02—Chemical tanning
    • C14C3/08—Chemical tanning by organic agents
    • C14C3/22—Chemical tanning by organic agents using polymerisation products
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F28/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur

Definitions

  • the unsaturated acid used is preferably 75 to 100% methacrylic acid and 25 to 0% respectively of acrylic acid, and generally the use of methacrylic acid exclusively is most practical from the standpoint of cost and effectiveness.
  • the amount of sulfonated oil is from to 25% by weight of the acid monomer.
  • the present invention is concerned with the tanning of leather.
  • compositions made up with the tanning agent and a fat-liquoring agent such as an oil have the disadvantage that there is gross separation of the oil from the composition on storage after a few days.
  • tanning compositions can be made by copolymerization of a mixture of (A) methacrylic acid, acrylic acid or mixtures of such acids with (B) a sulfated unsaturated oil.
  • the unsaturated acid used is preferably 75 to 100% methacrylic acid and 25 to 0% respectively of acrylic acid, and generally the use of methacrylic acid exclusively is most practical from the standpoint of cost and etfectiveness.
  • the amount of sulfated oil is from 10 to 25% by weight of the acid monomer. Preferably, the amount of such oil is about to based on the weight of the monomer.
  • the sulfated oil with which the unsaturated acid is polymerized is one in which the extent of sulfation has not been so great as to completely eliminate points of unsaturation in the product.
  • the extent of sulfation may be such as to remove all points except one of unsaturation in the oil.
  • the sulfation may be exerted exclusively On the hydroxyl groups leaving all of the points of unsaturation essentially untouched or the sulfation may convert both the hydroxyl groups and part of the unsaturated groups into sulfates.
  • olive oil which contains as a major constituent a glyceride of oleic acid
  • sulfation may introduce sulfate groups on one or two of the three points of unsaturation in the glyceride molecule leaving one or two of the unsaturated groups essentially untouched or unmodified.
  • olive oil is mentioned there may be used instead any of the other animal and vegeice table oils containing one or more glycerides of unsaturated acids having long chains such as from 12 to 20 carbon atoms. Examples of these oils include:
  • the copolymerization is effected in an aqueous medium in which the sulfated oil is dissolved, for example at a concentration of 5% to 15% by weight.
  • a water-soluble polymerization initiator and, optionally, a water-soluble chain-transfer agent.
  • An aqueous solution of a chain-transfer agent may also be dissolved directly in the monomer and this solution may then be added to the sulfated oil/ catalyst solution in the flask.
  • the sulfated oil/catalyst solution (which may also contain a chain-transfer agent) may be held at room temperature or raised to as high as 97 C.
  • the product of the present invention which is highly effective as a tanning agent for leather and has the advantage of effecting tannage without imparting crackiness to the grain of the leather even without fat-liquoring the leather.
  • the relative proportions of the acid monomer and sulfated oil are and by weight of monomer to 20 to 10% by weight respectively of the oil. In other words, the amount of monomer used is about 4 to 8 times the amount of sulfated oil.
  • the proportion of initiator is from 0.5 to 6% by weight of the monomer. Examples of initiators include hydrogen peroxide, ammonium persulfate, sodium persulfate, and potassium persulfate.
  • the proportion of chain transfer agent depends on the particular agent and its effectiveness in controlling the molecular weight of the copolymer. In general, the amount of chain transfer agent used is correlated with the amount of initiator so as to result in the production of a copolymer which in acid form at approximately 33% concentration in water and at 25 C. will have a viscosity in the range of about 15 to 300 poises. No chain-transfer agent is needed if the proportion of initiator used is high enough to produce a copolymer of low molecular weight in the range specified. It is estimated that the most suitable molecular weight range of the product is from about 5,000 to 50,000 number average.
  • chain-transfer agents examples include hydroxylamine or salts thereof, such as hydroxylamine sulfate, mercaptoethanol, mercaptopropanol, thiodiglycol, thioglycollic acid, ascorbic and isoascorbic acid.
  • the chain-transfer agent may be used in an amount of about 0.2 to 3.5% by weight based on the weight of the monomer.
  • copolymers of the present invention are water-soluble and dilutable. They remain in solution indefinitely without signifiicaut separation of oil content and are capable of tanning skins or hides without imparting crackiness to the grain.
  • the copolymer is dissolved in water at a concentration of about 5 to 40% by weight.
  • the copolymer need not be isolated from the aqueous solution in which it is prepared. Such solutions need only be adjusted to the desired concentration for use in tanning.
  • a salt such as sodium chloride or sodium sulfate, is included in the tanning solution at a concentration of 3 to 8% by weight.
  • the tanning liquor is introduced into a suitable vessel such as the conventional tanning drum and then the skins are introduced into the drum.
  • the weight of skins relative to the weight of liquor is generally determined to provide about 20 to 25% of active tanning agent based on the weight of wet pickled skin and about 5 to 15% of salt, when used, on the weight of skin.
  • the tanning is effected by tumbling the skin within the drum or vessel at room temperature up to but not above 35 C. Most commonly, the temperature may extend between 28 and 32 C. The tumbling in the tanning liquor may be carried out for a number of hours such as from 4 to 24 hours.
  • This tannage may be followed by a mineral tanning, vegetable extract tanning, or synthetic tanning agent.
  • the concentration of the copolymer may be from /2 to 10% by weight in the tanning liquor.
  • the amount of the tanning liquor relative to the partially tanned leather treated therewith is such as to provide about 1% to 5% of the copolymer based on the weight of the wet chrome leather. This means that to provide 3% on the leather there would be used 200% based on the weight of leather of a liquor containing 1 /2% of the copolymer.
  • the tanning composition of the present invention may be employed for the treatment of all types of skins and hides, such as horsehide, cowhide, kidskin, lambskin, goatskin, pigskin and so on.
  • the tanned products are adapted for use in all types of leathers such as shoe, sole and upper, garment, case, upholstery and industrial leathers.
  • aqueous sulfated castor oil (234 g. actual oil) a Solution A is heated in a glass reaction vessel to 90 C.
  • Solutions B and C are added gradually simultaneously over a 50-minute period through suitable devices, such as dropping funnels, to feed the reaction vessel, holding the temperature at 89 to 93 C.
  • the mixture is heated 1 hours longer at 90 C. (:1" C.). It is then cooled, while agitating, to 70-75 C. There is then added 0.1% phenol (based on product) and stirring is continued another minutes at 7075 C.
  • the 33 /a% solids copolymer solution weighs 4268 g. and has a viscosity of 33 poises at C. (Brookfield LVF viscometer, No. 3 spindle at 12 r.p.m.)
  • Acid/sulfated oil copolymer solutions of'approxi mately 30% concentration are obtained by repeating procedure 7 except that the sulfated. codfish oil is replaced by (a) sulfated castor oil (b) sulfated meats-foot oil (0) sulfated sperm oil (d) sulfated soybean oil
  • sulfated castor oil a) sulfated castor oil
  • d sulfated soybean oil
  • Each of the resulting copolymer solutions may be used for tanning, retanning or pretanning as in any of procedures 2, 4, 6, 8 and 10.
  • composition of matter a copolymer of a mix ture of (A) to by weight of an acid selected from the group consisting of acrylic acid, methacrylic acid, and mixtures thereof and (B) 20 to 10% by weight of an unsaturated sulfation product of an oil selected from the group consisting of animal and vegetable oils.
  • composition of matter a copolymer of a mixture of (A) 80 to 90% by weight of an acid selected from the group consisting of acrylic acid, methacrylic acid, and mixtures thereof and (B) 20 to 10% by weight of an unsaturated sulfation product of an oil selected from the group consisting of animal and vegetable oils, a 33% solution in water of said copolymer in acid form at 25 0., having a viscosity of about 15 to 300 poises.
  • composition of matter a copolymer of a mixture of (A) 80 to 90% by weight of methacrylic acid and (B) 20 to 10% by weight of an unsaturated sulfation product of a vegetable oil.
  • composition of matter a copolymer of a mixture of (A) 80 to 90% by weight of methacrylic acid and (B) 20 to 10% by weight of an unsaturated sulfation product of an animal oil.
  • composition of matter a copolymer of a mixture of (A) 80 to 90% by weight of methacrylic acid and (B) 20 to 10% by weight of an unsaturated sulfation product of castor oil.
  • composition of matter a copolymer of a mixture of (A) 80 to 90% by weight of methacrylic acid and (B) 20 to 10% by weight of an unsaturated sulfation product of neats foot oil.
  • composition of matter a copolymer of a mixture of (A) '80 to 90% by weight of methacrylic acid and (B) 20 to 10% by weight of an unsaturated sulfation product of sperm oil.
  • composition of matter a copolymer of a mixture of (A) 80 to 90% by weight of methacrylic acid and (B) 20 to 10% by weight of an unsaturated sulfation product of codfish oil.
  • composition of matter a copolymer of a mixture of (A) 80 to 90% by weight of methacrylic acid and (B) 20 to 10% by weight of an unsaturated sulfation product of soybean oil.
  • composition of matter a copolymer of a mixture of (A) 80 to 90% by weight of a mixture of at least 75% by weight of methacrylic acid and up to 25% by Weight of acrylic acid and (B) 20 to 10% by weight of an unsaturated sulfation product of castor oil.
  • composition of matter a copolymer of a mixture of (A) 80 to 90% by weight of a mixture of at least 7 75% by weight of methacrylic acid and up to 25% by weight of acrylic acid and (B) 20 to 10% by weight of an unsaturated sulfation product of meats-foot oil.
  • composition of matter a copolymer of a mixture of (A) 80 to 90% by weight of a mixture of at least 75 by weight of methacrylic acid and up to 25% by Weight of acrylic acid and (B) 20 to 10% by Weight of an unsaturated sulfation product of sperm oil.
  • composition of matter a copolymer of a mixture of (A) 80 to 90% by weight of a mixture of at least 75 by weight of methacrylic acid and up to 25% by weight of acrylic acid and (B) 20 to 10% by weight of an unsaturated sulfation product of codfish oil.
  • composition of matter a copolymer of a mixture of (A) 80 to 90% by Weight of a mixture of at least 75 by weight of methacrylic acid and up to 25 by weight of acrylic acid and (B) 20 to 10% by weight of an unsaturated sulfation product of soybean oil.
  • a copolymer of a mixture of (A) 80 to 90% by weight of an acid selected from the group consisting of acrylic acid, methacrylic acid, and mixtures thereof and (B) 20 to 10% by weight of an unsaturated sulfation product of an oil selected from the group consisting of animal and vegetable oils serves as a tanning agent therein.
  • an aqueous solution containing 3 to 8% by weight, based on the total solution weight of a salt selected from the group consisting of sodium chloride and sodium sulfate, and 5 to 40% by weight, based on the total solution weight, of a copolymer of a mixture of (A) to by weight of an acid selected from the group consisting of acrylic acid, methacrylic acid, and mixtures thereof and (B) 20 to 10% by weight of an unsaturated sulfation product of an oil selected from the group consisting of animal and vegetable oils, a 33% solution in water of said copolymer in acid form at 25 C., having a viscosity of about 15 to 300 poises.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Treatment And Processing Of Natural Fur Or Leather (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polymerisation Methods In General (AREA)
US416874A 1964-12-08 1964-12-08 Tanning compositions comprising aqueous solutions of unsaturated acid-unsaturated sulfated oil copolymers Expired - Lifetime US3408319A (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
US416874A US3408319A (en) 1964-12-08 1964-12-08 Tanning compositions comprising aqueous solutions of unsaturated acid-unsaturated sulfated oil copolymers
DE1494858A DE1494858C3 (de) 1964-12-08 1965-11-19 Verfahren zur Herstellung von Mischpolymerisaten und deren Verwendung als Gerbmittel
BE672851D BE672851A (da) 1964-12-08 1965-11-25
FR39837A FR1457045A (fr) 1964-12-08 1965-11-25 Compositions pour le tannage du cuir
ES0320165A ES320165A1 (es) 1964-12-08 1965-11-30 Un procedimiento para la preparacion de un polimero acrilico.
NL656515574A NL148069B (nl) 1964-12-08 1965-11-30 Werkwijze ter bereiding van een acrylpolymeer, werkwijze ter bereiding van een looisamenstelling, alsmede daarmee gelooid vel leer.
FI2915/65A FI44484B (da) 1964-12-08 1965-12-02
GB51248/65A GB1111868A (en) 1964-12-08 1965-12-02 Copolymers for tanning leather
NO65160776A NO122765B (da) 1964-12-08 1965-12-04
BR175485/65A BR6575485D0 (pt) 1964-12-08 1965-12-06 Processo para preparacao de um polimero acrilico e composicao de curtimento
DK629765AA DK111969B (da) 1964-12-08 1965-12-07 Garvemiddel.
IL24749A IL24749A (en) 1964-12-08 1965-12-07 Copolymers for tanning leather
SE15893/65A SE317503B (da) 1964-12-08 1965-12-08

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US416874A US3408319A (en) 1964-12-08 1964-12-08 Tanning compositions comprising aqueous solutions of unsaturated acid-unsaturated sulfated oil copolymers

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US3408319A true US3408319A (en) 1968-10-29

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US416874A Expired - Lifetime US3408319A (en) 1964-12-08 1964-12-08 Tanning compositions comprising aqueous solutions of unsaturated acid-unsaturated sulfated oil copolymers

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US (1) US3408319A (da)
BE (1) BE672851A (da)
BR (1) BR6575485D0 (da)
DE (1) DE1494858C3 (da)
DK (1) DK111969B (da)
ES (1) ES320165A1 (da)
FI (1) FI44484B (da)
GB (1) GB1111868A (da)
IL (1) IL24749A (da)
NL (1) NL148069B (da)
NO (1) NO122765B (da)
SE (1) SE317503B (da)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0024886A1 (en) * 1979-08-24 1981-03-11 Rohm And Haas Company Process for tanning leather with acrylic polymer and mineral tanning agent and leather so produced
US4285688A (en) * 1979-03-28 1981-08-25 Leather Life, Inc. Saddle oil
US4334876A (en) * 1979-08-24 1982-06-15 Rohm And Haas Company Process for producing leather
US4345006A (en) * 1980-08-18 1982-08-17 Rohm Gmbh Method of treating leather
US4398911A (en) * 1979-07-26 1983-08-16 Rohm Gmbh Tanning method
US4439201A (en) * 1981-03-06 1984-03-27 Ciba-Geigy Corporation Process for retanning leather with acrylic-based oligomers
US4626559A (en) * 1985-04-22 1986-12-02 Pep Rally Paint, Inc. Non-permanent ornamental paint mixture
US4822373A (en) * 1988-03-11 1989-04-18 Minnesota Mining And Manufacturing Company Process for providing polyamide materials with stain resistance with sulfonated novolak resin and polymethacrylic acd
US4937123A (en) * 1988-03-11 1990-06-26 Minnesota Mining And Manufacturing Company Process for providing polyamide materials with stain resistance
US5074883A (en) * 1989-12-11 1991-12-24 Minnesota Mining And Manufacturing Company Process for providing polyamide materials with stain resistance
US5223340A (en) * 1989-04-20 1993-06-29 Peach State Labs, Inc. Stain resistant polyamide fibers
US5310828A (en) * 1989-04-20 1994-05-10 Peach State Labs, Inc. Superior stain resistant compositions
US5428117A (en) * 1993-10-18 1995-06-27 Interface, Inc. Treatment for imparting stain resistance to polyamide substrates and resulting stain resistant materials
US5620748A (en) * 1992-07-24 1997-04-15 Basf Aktiengesellschaft Use of graft polymers for fatliquoring and filling leather and fur skins
DE19625984A1 (de) * 1996-06-28 1998-01-08 Stockhausen Chem Fab Gmbh Wäßrige Polymerdispersionen, Verfahren zu ihrer Herstellung und ihre Verwendung in der Lederherstellung
US6524492B2 (en) 2000-12-28 2003-02-25 Peach State Labs, Inc. Composition and method for increasing water and oil repellency of textiles and carpet

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3413301A1 (de) * 1984-04-09 1985-10-24 Chemische Fabrik Stockhausen GmbH, 4150 Krefeld Verfahren zum nachgerben von mineralisch oder kombiniert gegerbtem leder mit polymergerbstoffen
DE4440846A1 (de) * 1994-11-15 1996-05-23 Basf Ag Verfahren zur Herstellung von Leder und Pelzfellen unter Verwendung von Polymergerbstoffen

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2205883A (en) * 1938-06-16 1940-06-25 Du Pont Tanning
US2280310A (en) * 1940-10-25 1942-04-21 Socony Vacuum Oil Co Inc Treatment of leather
US2452536A (en) * 1944-07-25 1948-11-02 Du Pont Process for impregnating leather with sulfonated polymeric compositions
US3231420A (en) * 1962-07-06 1966-01-25 Rohm & Haas Process for treating leather and leathers obtained
US3245832A (en) * 1962-11-23 1966-04-12 Armour & Co Impregnation of leather with polymer dispersion by application of pressure
US3291558A (en) * 1961-08-29 1966-12-13 Degussa Treatment of leather

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2205883A (en) * 1938-06-16 1940-06-25 Du Pont Tanning
US2280310A (en) * 1940-10-25 1942-04-21 Socony Vacuum Oil Co Inc Treatment of leather
US2452536A (en) * 1944-07-25 1948-11-02 Du Pont Process for impregnating leather with sulfonated polymeric compositions
US3291558A (en) * 1961-08-29 1966-12-13 Degussa Treatment of leather
US3231420A (en) * 1962-07-06 1966-01-25 Rohm & Haas Process for treating leather and leathers obtained
US3245832A (en) * 1962-11-23 1966-04-12 Armour & Co Impregnation of leather with polymer dispersion by application of pressure

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4285688A (en) * 1979-03-28 1981-08-25 Leather Life, Inc. Saddle oil
US4398911A (en) * 1979-07-26 1983-08-16 Rohm Gmbh Tanning method
US4443221A (en) * 1979-07-26 1984-04-17 Rohm Gmbh Tanning method
EP0024886A1 (en) * 1979-08-24 1981-03-11 Rohm And Haas Company Process for tanning leather with acrylic polymer and mineral tanning agent and leather so produced
JPS5659900A (en) * 1979-08-24 1981-05-23 Rohm & Haas Manufacture of leather
US4314802A (en) * 1979-08-24 1982-02-09 Rohm And Haas Company Process for producing leather
US4334876A (en) * 1979-08-24 1982-06-15 Rohm And Haas Company Process for producing leather
US4345006A (en) * 1980-08-18 1982-08-17 Rohm Gmbh Method of treating leather
US4439201A (en) * 1981-03-06 1984-03-27 Ciba-Geigy Corporation Process for retanning leather with acrylic-based oligomers
US4626559A (en) * 1985-04-22 1986-12-02 Pep Rally Paint, Inc. Non-permanent ornamental paint mixture
US4822373A (en) * 1988-03-11 1989-04-18 Minnesota Mining And Manufacturing Company Process for providing polyamide materials with stain resistance with sulfonated novolak resin and polymethacrylic acd
US4937123A (en) * 1988-03-11 1990-06-26 Minnesota Mining And Manufacturing Company Process for providing polyamide materials with stain resistance
US5223340A (en) * 1989-04-20 1993-06-29 Peach State Labs, Inc. Stain resistant polyamide fibers
US5310828A (en) * 1989-04-20 1994-05-10 Peach State Labs, Inc. Superior stain resistant compositions
US5074883A (en) * 1989-12-11 1991-12-24 Minnesota Mining And Manufacturing Company Process for providing polyamide materials with stain resistance
US5620748A (en) * 1992-07-24 1997-04-15 Basf Aktiengesellschaft Use of graft polymers for fatliquoring and filling leather and fur skins
US5428117A (en) * 1993-10-18 1995-06-27 Interface, Inc. Treatment for imparting stain resistance to polyamide substrates and resulting stain resistant materials
DE19625984A1 (de) * 1996-06-28 1998-01-08 Stockhausen Chem Fab Gmbh Wäßrige Polymerdispersionen, Verfahren zu ihrer Herstellung und ihre Verwendung in der Lederherstellung
DE19625984C2 (de) * 1996-06-28 1999-07-29 Stockhausen Chem Fab Gmbh Wäßrige Polymerdispersionen, Verfahren zu ihrer Herstellung und ihre Verwendung in der Lederherstellung
US6133372A (en) * 1996-06-28 2000-10-17 Stockhausen Gmbh & Co. Kg Aqueous polymer dispersion, process for preparing the same and its use in leather production
US6524492B2 (en) 2000-12-28 2003-02-25 Peach State Labs, Inc. Composition and method for increasing water and oil repellency of textiles and carpet

Also Published As

Publication number Publication date
DK111969B (da) 1968-10-28
NL6515574A (da) 1966-06-09
DE1494858A1 (de) 1969-10-09
SE317503B (da) 1969-11-17
NO122765B (da) 1971-08-09
NL148069B (nl) 1975-12-15
GB1111868A (en) 1968-05-01
IL24749A (en) 1969-05-28
FI44484B (da) 1971-08-02
DE1494858C3 (de) 1974-11-07
BE672851A (da) 1966-05-25
DE1494858B2 (de) 1974-03-28
ES320165A1 (es) 1966-09-01
BR6575485D0 (pt) 1973-05-24

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