US3922446A - Process of impregnating leather and leather substitute materials - Google Patents
Process of impregnating leather and leather substitute materials Download PDFInfo
- Publication number
- US3922446A US3922446A US295457A US29545772A US3922446A US 3922446 A US3922446 A US 3922446A US 295457 A US295457 A US 295457A US 29545772 A US29545772 A US 29545772A US 3922446 A US3922446 A US 3922446A
- Authority
- US
- United States
- Prior art keywords
- leather
- acid
- group
- salt
- weight
- 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
Links
- 239000010985 leather Substances 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims abstract description 30
- 230000008569 process Effects 0.000 title claims abstract description 27
- 239000002649 leather substitute Substances 0.000 title claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- -1 nitrogen-containing heterocyclic compound Chemical class 0.000 claims abstract description 17
- 238000004078 waterproofing Methods 0.000 claims abstract description 13
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims description 21
- 239000004215 Carbon black (E152) Substances 0.000 claims description 18
- 229930195733 hydrocarbon Natural products 0.000 claims description 18
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 claims description 17
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 claims description 17
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 claims description 17
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 9
- 150000003230 pyrimidines Chemical class 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 5
- 150000002462 imidazolines Chemical class 0.000 claims description 5
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 4
- 229960001124 trientine Drugs 0.000 claims description 4
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 claims description 3
- 229920001281 polyalkylene Polymers 0.000 claims description 3
- 229920000768 polyamine Polymers 0.000 claims description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 38
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 17
- 239000000047 product Substances 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 150000001735 carboxylic acids Chemical class 0.000 description 11
- 239000007859 condensation product Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- 238000005470 impregnation Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 7
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 7
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 7
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 7
- 239000005642 Oleic acid Substances 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 7
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 7
- 125000002947 alkylene group Chemical group 0.000 description 6
- 238000006482 condensation reaction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- MKJHXLKVZNDNDB-UHFFFAOYSA-N 2-phenyloctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(C(O)=O)C1=CC=CC=C1 MKJHXLKVZNDNDB-UHFFFAOYSA-N 0.000 description 5
- 238000005755 formation reaction Methods 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- QPXDCWRAUMXWMG-KTKRTIGZSA-N 2-hydroxy-2-[2-[(z)-octadec-9-enoxy]-2-oxoethyl]butanedioic acid Chemical class CCCCCCCC\C=C/CCCCCCCCOC(=O)CC(O)(C(O)=O)CC(O)=O QPXDCWRAUMXWMG-KTKRTIGZSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000009963 fulling Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical class CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000009988 textile finishing Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
- C07D233/12—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D233/16—Radicals substituted by nitrogen atoms
-
- 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
-
- 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
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/4935—Impregnated naturally solid product [e.g., leather, stone, etc.]
Definitions
- ABSTRACT A process for waterproofing leather or leather substitute articles comprises impregnating the articles with an organic solvent solution of a salt of a nitrogencontaining heterocyclic compound and a carboxylic acid having more than 21 carbon atoms.
- It is another object of the present invention to provide a process for waterproofing leather or leather substitutes which comprises impregnating leather or leather substitutes with an organic solution of a salt of a high-molecular-weight hydrocarbon carboxylic acid having to 30 carbon atoms and a basic nitrogen-containing heterocyclic compound selected from the group consisting of an imidazoline derivative and a pyrimidine derivative of the formula in which R is a higher hydrocarbon radical having 9 to 29 carbon atoms, with the proviso that whenever the carboxylic acid has no more than 21 carbon atoms then R has more than carbon atoms; R is an alkylene having 2 to 3 carbon atoms, m is an integer from 1 to 3 and n is an integer from 2 to 3.
- the present invention is directed to a process for waterproofing leather or leather substitutes which comprises impregnating leather or leather substitutes with an organic solution of a salt of a high-molecular-weight hydrocarbon carboxylic acid having 10 to carbon atoms and a basic nitrogen-containing heterocyclic compound selected from the group consisting of an imidazoline derivative and a pyrimidine derivative of the formula in which R is a higher hydrocarbon radical having 9 to i 29 carbon atoms, with the proviso that whenever the carboxylic acid has no more than 21 carbon atoms then R has more than 20 carbon atoms; R is an alkylene having 2 to 3 carbon atoms, m is an integer from 1 to 3 and n is an integer from 2 to 3.
- either the carboxylic acid has more than 21 carbon atoms or the grouping R,C will have more than 21 carbon atoms, or both the carboxylic acid and the grouping R,C will have more than 21 carbon atoms, according to the invention.
- both the carboxylic acid and the grouping R,C cannot have less than 21 carbon atoms each, in the same compound.
- the production of the imidazoline or pyrimidine derivatives is described in the disclosure of U.S. Pat. No. 3,475,206.
- the starting materials are higher-molecular-weight carboxylic acids, which are condensed with polyalkylene polyamines, such as diethylene triamine, triethylene tetramine, or dipropylene triamine, at an elevated temperature, with the water formed in the reaction being removed by distillation.
- the salt formation occurs in a known manner by neutralization of the condensation product with a carboxylic acid of the desired structure or chain length.
- carboxylic acids with more than 21 carbon atoms are utilized for the condensation and/or the neutralization steps.
- preferred carboxylic acids are those which contain from 22 to 30, preferably from 22 to 26 carbon atoms, for example those which are unsaturated, for example alkenoic acids of 22 to 26 carbon atoms such as erucic acid, hydroxyalkenoic of 22 to 26 carbon atoms, alkadienoic acids of 22 to 26 carbon atoms, and alkatrienoic acids of 22 to 26 carbon atoms, and the mixtures thereof
- Other preferred carboxylic acids contain branch-chained alkyl substituents and these acids have 22 to 26 carbon atoms, or phenyl alkanoic acids of 22 to 26 carbon atoms, such as phenylstearic acid, and the mixtures thereof.
- carboxylic acids are erucic acid and omega-phenylstearic acid.
- carboxylic acids are erucic acid and omega-phenylstearic acid.
- other higher-molecular-weight carboxylic acids in particular unsaturated or branch-chained carboxylic acids, such as resinic acids, montanic acids or the branch-chained carboxylic acids obtained by oxidation of branch-chained paraffins with more than 21 carbon atoms, may be used.
- carboxylic acids used for carrying out the condensation reaction and the salt formation reaction may be identical or different. It is also possible to use naturally occurring fatty acids of the claimed chain lengths, as well as the mixtures thereof, or in combination with other carboxylic acids.
- Suitable impregnating agents are the salt of a higher 'carboxylic acid of more than 21 carbon atoms with the condensation product of said acid and an aliphatic amine of the formula NH [(CH ),,NH- ],,H, in which p 2 to 3 and q 2 to 4, such as the salt of erucic acid with the condensation product from diethylene triamine and erucic acid, the salt of omegaphenylstearic acidwith the condensation product from diethylene triamine and omega-phenylstearic acid, the salt from oleic acid with the condensation product from diethylene triamine and omega-phenylstearic acid, and the salt from erucic acid with the condensation product from triethylene tetramine and oleic acid.
- the salts are readily soluble in organic solvents, for example aliphatic hydrocarbons, aromatic hydrocarbons, chlorinated hydrocarbons, for example chlorinated alkylenes such as trichloroethylene, or alcohols for example lower alkanols such as isopropanol and the mixtures thereof, resulting in solutions of low viscosity.
- organic solvents for example aliphatic hydrocarbons, aromatic hydrocarbons, chlorinated hydrocarbons, for example chlorinated alkylenes such as trichloroethylene, or alcohols for example lower alkanols such as isopropanol and the mixtures thereof, resulting in solutions of low viscosity.
- a further improvement of the impregnation effect can be obtained by combining the products according to the present invention with partially esterified or partially etherified poly-alcohols or partially esterified polycarboxylic acids which contain at least one unsaturated or branch-chained grouping with 8 to 22 carbon atoms.
- Especially preferred compounds of this group are the glycerin and pentaerythrite partial esters of the higher fattyacids of 8 to 22 carbon atoms, in particular oleic acid.
- citric acid mono-oleyl esters are especially preferred.
- the impregnation is carried out either by immersing the leather in the organic solutions containing about 5% to 30% by weight of the products or by applying the solution directly to the leather such as by spreading, brushing or spraying thereon. Even in the presence of relatively low quantities of water, the alcoholic solutions of these salts maintain their low viscosity, such that the desired impregnation effects can be obtained by fulling the alcoholic solutions into the still moist leather in the tanning barrel.
- the products of the invention are noted for possessing a considerable water binding and swelling capacity. This activity is probably based on the formation of viscous or pasty water-in-oil emulsions within the fiber interstices of the leather. Thus whenever the impregnated leather is contacted by a very slight amount of moisture the pores are closed and resistance is offered to the further penetration of water into the leather. Accordingly, the passage of water through the leather is not only greatly retarded, but the absorption of water into the leather is also reduced.
- a special advantage of the present products is their stability within the leather toward repeated wetting. Even after many hours of mechanically stressing the wet leather containing the present impregnating agent, this impregnating agent is not washed out. To enhance the effect of the impregnation agents or to achieve special effects, certain known impregnating agents, greasing agents, silicones or the like can be used as well.
- EXAMPLE 1 In order to provide a basis for determining the waterproofing effect after impregnation of the leather or leather substitute, the following products A, B, and C were prepared:
- Product A 32.9 parts by weight of phenylstearic acid and 9.5 parts by weight of diethylene triamine were heated while stirring. Elimination of water started at 150C; and the temperature was increased to 220C. After the condensation reaction was completed, 32.9 parts by weight of phenylstearic acid were added to neutralize the basic condensation product, to give Product A.
- Product B Phenylstearic acid and diethylene triamine were reacted according to the procedure as described for Product A.
- the reaction product was neutralized with 25.8 parts by weight of oleic acid to given Product B.
- Product C 25.8 parts by weight of oleic acid were heated together with 9.5 parts by weight of diethylene triamine while stirring. The elimination of water started at 140C; and the temperature was slowly increased to 220C. After the condensation reaction was completed,
- the Products A to D were dissolved in the weight ratio 1:4 in an equal parts by volume mixture of trichloroethylene and isopropanol.
- two different bottom leathers I and H
- tanned by a vegetable type synthetic tanning agent were impregnated by immersing these leathers for 15 minutes in said solutions and then drying then in air for about 24 hours. Following this they were dried further by heating for 2 hours to about 50C in the drying cabinet (designation of the impregnated leathers l A, I B. etc., II A, II B, etc.).
- Retanned chrome upper leather was impregnated, as described in Example 2, with solutions of the impregnation agents B and E, and with Product D for comparison.
- the impregnated leathers were tested according to the method common in the U.S.A.., described by Maeser (J. American Leather Chemists Assoc., 42, 390
- a process for waterproofing leather or leather substitutes which comprises impregnating leather or leather substitutes with an organic solution of a salt of a high-molecular-weight hydrocarbon carboxylic acid selected from the group consisting of erucic acid and omega-phenylstearic acid and a basic nitrogen-containing heterocyclic compound selected from the group consisting of an imidazoline derivative and a pyrimidine derivative of the formula in which R is a higher hydrocarbon radical derived from a carboxylic acid selected from the group consisting of erucic acid and omega-phenylstearic acid, R is an alkylene having 2 to 3 carbon atoms, m is an integer from 1 to 3, and n is an integer from 2 to 3.
- organic solution contains from about 5% to 30% by weight of said salt in an organic solvent selected from the group consisting essentially of aliphatic hydrocarbons, aromatic hydrocarbons, chlorinated hydrocarbons, alcohols, and the mixtures thereof.
- R is a higher hydrocarbon radical derived from a carboxylic acid selected from the group consisting of erucic acid and omega-phenylstearic acid
- R is an alkylene having 2 to 3 carbon atoms
- m is an integer from 1 to 3
- n is an integer from 2 to 3
- said nitrogen-containing heterocyclic compound being the condensation product of an aliphatic amine of the formula z"[( z)
- the aliphatic amine is a polyalkylene polyamine selected from the group consisting of diethylene triamine, triethylene tetramine, and dipropylene triamine.
- organic solution contains from about 5% to 30% by weight of said salt in an organic solvent selected from the group consisting essentially of aliphatic hydrocarbons, aromatic hydrocarbons, chlorinated hydrocarbons, alcohols, and
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
- Synthetic Leather, Interior Materials Or Flexible Sheet Materials (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2151409A DE2151409C3 (de) | 1971-10-15 | 1971-10-15 | Verfahren zum Wasserfestmachen von Leder- oder Lederaustauschstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3922446A true US3922446A (en) | 1975-11-25 |
Family
ID=5822443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US295457A Expired - Lifetime US3922446A (en) | 1971-10-15 | 1972-10-06 | Process of impregnating leather and leather substitute materials |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3922446A (enrdf_load_stackoverflow) |
| JP (1) | JPS5532760B2 (enrdf_load_stackoverflow) |
| CH (1) | CH586283A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2151409C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2157454A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1383006A (enrdf_load_stackoverflow) |
| IT (1) | IT968915B (enrdf_load_stackoverflow) |
| NL (1) | NL170309C (enrdf_load_stackoverflow) |
| SE (1) | SE402787B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030149158A1 (en) * | 2001-11-05 | 2003-08-07 | 3M Innovative Properties Company | Water-and oil-repellent, antistatic compositions |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6284402U (enrdf_load_stackoverflow) * | 1985-11-19 | 1987-05-29 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2468163A (en) * | 1948-01-10 | 1949-04-26 | Petrolite Corp | Processes for preventing corrosion and corrosion inhibitors |
| US2872428A (en) * | 1955-01-31 | 1959-02-03 | Shell Dev | Polyepoxide emulsions and method of treating textiles therewith |
| US2887485A (en) * | 1956-01-06 | 1959-05-19 | Rohm & Haas | New cyclic urea derivatives |
| US3278561A (en) * | 1962-06-15 | 1966-10-11 | Monsanto Co | Hydrophobic diglycidylamines |
| US3475206A (en) * | 1965-08-18 | 1969-10-28 | Bohme Fettchemie Gmbh | Waterproofing of leather and synthetic leathers |
-
1971
- 1971-10-15 DE DE2151409A patent/DE2151409C3/de not_active Expired
-
1972
- 1972-09-18 NL NLAANVRAGE7212624,A patent/NL170309C/xx not_active IP Right Cessation
- 1972-09-18 SE SE7212034A patent/SE402787B/xx unknown
- 1972-10-06 US US295457A patent/US3922446A/en not_active Expired - Lifetime
- 1972-10-13 GB GB4724272A patent/GB1383006A/en not_active Expired
- 1972-10-13 FR FR7236274A patent/FR2157454A5/fr not_active Expired
- 1972-10-13 IT IT30428/72A patent/IT968915B/it active
- 1972-10-14 JP JP72102377A patent/JPS5532760B2/ja not_active Expired
- 1972-10-16 CH CH1506672A patent/CH586283A5/xx not_active IP Right Cessation
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2468163A (en) * | 1948-01-10 | 1949-04-26 | Petrolite Corp | Processes for preventing corrosion and corrosion inhibitors |
| US2872428A (en) * | 1955-01-31 | 1959-02-03 | Shell Dev | Polyepoxide emulsions and method of treating textiles therewith |
| US2887485A (en) * | 1956-01-06 | 1959-05-19 | Rohm & Haas | New cyclic urea derivatives |
| US3278561A (en) * | 1962-06-15 | 1966-10-11 | Monsanto Co | Hydrophobic diglycidylamines |
| US3475206A (en) * | 1965-08-18 | 1969-10-28 | Bohme Fettchemie Gmbh | Waterproofing of leather and synthetic leathers |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030149158A1 (en) * | 2001-11-05 | 2003-08-07 | 3M Innovative Properties Company | Water-and oil-repellent, antistatic compositions |
| US6924329B2 (en) | 2001-11-05 | 2005-08-02 | 3M Innovative Properties Company | Water- and oil-repellent, antistatic compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4848601A (enrdf_load_stackoverflow) | 1973-07-10 |
| NL7212624A (enrdf_load_stackoverflow) | 1973-04-17 |
| CH586283A5 (enrdf_load_stackoverflow) | 1977-03-31 |
| JPS5532760B2 (enrdf_load_stackoverflow) | 1980-08-27 |
| FR2157454A5 (enrdf_load_stackoverflow) | 1973-06-01 |
| DE2151409B2 (de) | 1979-09-20 |
| SE402787B (sv) | 1978-07-17 |
| NL170309B (nl) | 1982-05-17 |
| DE2151409C3 (de) | 1980-07-10 |
| IT968915B (it) | 1974-03-20 |
| DE2151409A1 (de) | 1973-04-19 |
| NL170309C (nl) | 1982-10-18 |
| GB1383006A (en) | 1975-02-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3595886A (en) | Novel fluorocarbon derivatives | |
| US5021264A (en) | Aqueous textile treatment agent and crease resist finishing of textile material | |
| US3922446A (en) | Process of impregnating leather and leather substitute materials | |
| US2637661A (en) | Fungicidal composition and process of using same | |
| DE2058317A1 (de) | Harnstoffverbindungen und deren Verwendung als Textilhilfsmittel | |
| US3475206A (en) | Waterproofing of leather and synthetic leathers | |
| US3981913A (en) | Mono-substituted ureas | |
| US3402071A (en) | Process to render leathers and furs water-resistant | |
| EP0140525B2 (en) | Leather treatment | |
| US3276891A (en) | Waterproofing of leather and furs | |
| US2964425A (en) | Waterproofing of leathers | |
| US3965072A (en) | Polyurea-urethane polymers from urea, diamines and aminoalcohols | |
| US3661631A (en) | Method for imparting water- and oil-repellent properties to leather and leather so treated | |
| US3996269A (en) | Polyurethane polymers | |
| US2897201A (en) | Epoxy quaternary ammonium compounds | |
| US3274023A (en) | Scuff resistant leather | |
| US813218A (en) | Process for rendering materials or articles resistant to water and chemicals. | |
| DD230137A3 (de) | Verfahren zur wasserabweisenden ausruestung von ledern aus tierhaeuten | |
| US2590017A (en) | Fluid seal packing | |
| US1737760A (en) | Reduction of the swelling capacity of hydrated cellulose and the resulting product | |
| US3163552A (en) | Process for making fibrous material hydrophobic | |
| US3573095A (en) | Epoxidized perfluoroalkylamide water-and oil-repellency agents | |
| DE1907767C3 (de) | Verfahren zum Imprägnieren von Leder- oder Lederaustauschstoffen | |
| US3510245A (en) | Ph 3.9 to 4.4 impregnation of an acidic vegetable tanned,fat-liquored leather with a dimethylol urea solution | |
| US3035882A (en) | Leather lubrication |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: ROBERTS-GORDON, INC., NEW YORK Free format text: RELEASE BY SECURED PARTY;ASSIGNOR:HELLER FINANCIAL, INC.;REEL/FRAME:007189/0769 Effective date: 19940817 |