EP0025933A1 - Mélange adjuvant et procédé de trempage des peaux et des fourrures - Google Patents
Mélange adjuvant et procédé de trempage des peaux et des fourrures Download PDFInfo
- Publication number
- EP0025933A1 EP0025933A1 EP80105377A EP80105377A EP0025933A1 EP 0025933 A1 EP0025933 A1 EP 0025933A1 EP 80105377 A EP80105377 A EP 80105377A EP 80105377 A EP80105377 A EP 80105377A EP 0025933 A1 EP0025933 A1 EP 0025933A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- hides
- skins
- aid
- surfactant
- liquor
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title claims abstract description 9
- 238000002791 soaking Methods 0.000 title description 2
- 239000004902 Softening Agent Substances 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 150000001768 cations Chemical class 0.000 claims abstract description 3
- 125000000524 functional group Chemical group 0.000 claims abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 239000004094 surface-active agent Substances 0.000 claims description 10
- 230000000844 anti-bacterial effect Effects 0.000 claims description 8
- 239000003899 bactericide agent Substances 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 230000003647 oxidation Effects 0.000 abstract description 4
- 238000007254 oxidation reaction Methods 0.000 abstract description 4
- 208000005374 Poisoning Diseases 0.000 abstract 1
- 231100000572 poisoning Toxicity 0.000 abstract 1
- 230000000607 poisoning effect Effects 0.000 abstract 1
- 230000035943 smell Effects 0.000 abstract 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QPOVMQFRUPYERN-UHFFFAOYSA-N S1(=S)(=O)OC(C(=O)O)O1.[Na] Chemical compound S1(=S)(=O)OC(C(=O)O)O1.[Na] QPOVMQFRUPYERN-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- 230000002110 toxicologic effect Effects 0.000 description 2
- 231100000027 toxicology Toxicity 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- OEZPDHRXGCLGKB-UHFFFAOYSA-N 2-chloropropanamide Chemical compound CC(Cl)C(N)=O OEZPDHRXGCLGKB-UHFFFAOYSA-N 0.000 description 1
- JNAYPRPPXRWGQO-UHFFFAOYSA-N 2-chloropropanenitrile Chemical compound CC(Cl)C#N JNAYPRPPXRWGQO-UHFFFAOYSA-N 0.000 description 1
- GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical compound CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 description 1
- JQDXZJYAUSVHDH-UHFFFAOYSA-N 3-chloropropanamide Chemical compound NC(=O)CCCl JQDXZJYAUSVHDH-UHFFFAOYSA-N 0.000 description 1
- QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical compound OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 description 1
- GNHMRTZZNHZDDM-UHFFFAOYSA-N 3-chloropropionitrile Chemical compound ClCCC#N GNHMRTZZNHZDDM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- RUPBZQFQVRMKDG-UHFFFAOYSA-M Didecyldimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(C)CCCCCCCCCC RUPBZQFQVRMKDG-UHFFFAOYSA-M 0.000 description 1
- 229920005682 EO-PO block copolymer Polymers 0.000 description 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- BNOODXBBXFZASF-UHFFFAOYSA-N [Na].[S] Chemical compound [Na].[S] BNOODXBBXFZASF-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- -1 amine salts Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 1
- 238000004380 ashing Methods 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 229960004670 didecyldimethylammonium chloride Drugs 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
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
- C14C1/00—Chemical treatment prior to tanning
- C14C1/04—Soaking
Definitions
- the skin of the skins has various tasks to perform in the leather production process.
- the skins should be returned to the state they were in after they were removed, i.e. dried or salted skins should have approximately the original water content after the turnout. Salted hides also need to be largely freed of salt.
- the switch has the task of removing dirt such as manure, blood residues, soluble proteins and fats from the hides.
- the switch should also prepare the skin for the subsequent liming. This means that the pH value in the switch should be between 8 and 10 in the entire cross-section of the skin in order to prevent a liming effect caused by an excessive pH jump.
- a certain amount of hair loosening should also be achieved so that it loosens more quickly and completely in the liming.
- the invention was therefore based on the object of developing a softening agent or a method for softening hides which fulfills all of the tasks described above, in particular also a certain loosening of hair, and which does not have the disadvantages mentioned, that is to say no sensitivity to oxidation and no toxicity and no smell.
- the compounds of the formula I are easy to prepare by reacting thiosulfate with a correspondingly reactive organic compound, for example according to or analogously to the following equations:
- the reaction products of sodium thiosulfate with chloroacetic acid and with ethylene oxide are particularly preferred.
- organic compounds are also suitable for reaction with thiosulfate to form a substance of the general formula I, for example propylene oxide, n-butylene oxide-1,2, chloroacetonitrile, 3-chloropropionitrile, 2-chloropropionitrile, 2- Chloroacetamide, 2-chloropropionamide, 3-chloropropionamide, ethyl chloride, n-propyl chloride, isopropyl chloride, n-octyl bromide, benzyl chloride, maleic anhydride, 3-chloropropionic acid, 2-chloropropionic acid, acrylic acid, crotonic acid and ß-chloroethanol.
- propylene oxide n-butylene oxide-1,2, chloroacetonitrile, 3-chloropropionitrile, 2-chloropropionitrile, 2- Chloroacetamide, 2-chloropropionamide, 3-chloropropionamide, ethyl chloride, n
- the radical R in formula I can thus represent an aliphatic or araliphatic radical with up to 8 carbon atoms, and this can be substituted by one or more carboxyl or carboxylate, hydroxyl, nitrile and / or amide groups, M + in formula I represents an equivalent of a cation, for example K + , NH 4 + , 1/2 Mg ++ , 1/2 Ca ++ , preferably Na.
- the softening conditions are the usual, i.e. liquor lengths of 200 to 1,000% water, calculated on the dry weight of the hides and skins, temperatures of 15 to 40, preferably 20 to 35 ° C. and softening times, depending on the type of skin, from 6 to 100, preferably 6 up to 48 hours.
- the softening agent mixture likewise claimed also contains surfactants, bactericides and optionally water.
- Nonionic and cationic surfactants are preferred.
- Typical nonionic surfactants are, for example, the numerous commercially available ethylene oxide and propylene oxide adducts and their mixed (mostly not statistically, but in block form) adducts of mono-, di- and polyfunctional alcohols, amines and polyamines, amino alcohols, carboxylic acids, acid amides, alkylphenols and block copolymers of ethylene oxide and propylene oxide, the propylene oxide being completely or partially replaced by butylene oxide can.
- Common cationic surfactants include fatty amine salts and quaternary ammonium compounds.
- quaternary ammonium salts are preferably used for the bactericides, since these are particularly non-toxic and support the softening effect due to their surfactant character. Examples include: benzyltrimethylammonium chloride; Didecyldimethylammonium chloride; 3,4-dichlorobenzyltrimethylanmonium chloride; also the "Seifen- ⁇ le-Fette-Wwachs" 104 (1978), 433-478 by M.H. Angele called connections.
- the active ingredient of the formula I according to the invention is used in the soft liquor in amounts of 0.01 to 0.4, preferably 0.05 to 0.3%, calculated on the dry weight of the skins.
- the salt weight is to be assumed as 2.5 times the dry weight as usual, in other words: with regard to the salt weight instead of the dry weight, the stated amounts are to be divided by 2.5.
- Two halves of a salted cowhide are agitated for 20 minutes in liming barrels filled with 200% water at a temperature of 28 ° C, then left to rest for 20 minutes and then agitated again for 20 minutes. The water is then drained off. Thereafter, 150% 28 ° C.
- a softening agent (I) which consists of 10 parts of sodium carboxymethylene thiosulfate, 30 parts of a commercially available propylene oxide ethylene oxide Block polymer, which is made from a propylene oxide block with a molecular weight of 1750 by reaction with 150 mol of ethylene oxide, 10 parts of benzyltrimethylammonium chloride and 50 parts of water. 150% 28 ° C. warm water, 0.5% soda and 0.5% of a softening agent (II), which consists of 30 parts of the above-mentioned PO-EO block polymer, 10 parts of benzyltrimethylammonium chloride and There are 60 parts of water.
- a softening agent (II) which consists of 30 parts of the above-mentioned PO-EO block polymer, 10 parts of benzyltrimethylammonium chloride and There are 60 parts of water.
- the two halves A and B of a dried cowhide of 8 parts by weight are treated as follows.
- Half A is agitated in a liming drum in 1000% water at 30 ° C with the addition of 1% soda and 1.5% of the aid designated I in Example 1 for 18 hours.
- Half B is softened with the addition of auxiliary means II in exactly the same way otherwise. After the turnout has ended, the hair in the half labeled A is much easier to remove than in the half B.
- the ashing is carried out as indicated in Example 1.
- Half A is significantly lighter than half B.
- Example 3-5 the procedure is analogous to Example 1, except that sodium carboxymethylene thiosulfate is replaced by other compounds of the formula I in the softening agent. The details are shown in Table 1.
- Example 2 the procedure is analogous to Example 2, except that the composition of the softening agent and the amount used are varied as indicated in Table 2.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19792938078 DE2938078A1 (de) | 1979-09-20 | 1979-09-20 | Hilfsmittel und verfahren zum weichen von haeuten |
DE2938078 | 1979-09-20 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0025933A1 true EP0025933A1 (fr) | 1981-04-01 |
EP0025933B1 EP0025933B1 (fr) | 1983-02-16 |
Family
ID=6081385
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP80105377A Expired EP0025933B1 (fr) | 1979-09-20 | 1980-09-09 | Mélange adjuvant et procédé de trempage des peaux et des fourrures |
Country Status (6)
Country | Link |
---|---|
US (1) | US4322210A (fr) |
EP (1) | EP0025933B1 (fr) |
JP (1) | JPS5653200A (fr) |
AU (1) | AU532669B2 (fr) |
DE (2) | DE2938078A1 (fr) |
ES (1) | ES495201A0 (fr) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20060112494A1 (en) * | 2004-12-01 | 2006-06-01 | David Oppong | Method of protecting an animal skin product from metalloproteinase activity |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2225601A (en) * | 1936-06-26 | 1940-12-17 | Wallerstein Co Inc | Dehairing of skins and hides |
US3567363A (en) * | 1965-09-20 | 1971-03-02 | Gillette Co | Modification of keratin to the s-sulfo form |
YU36755B (en) * | 1971-11-17 | 1984-08-31 | Basf Ag | Process for the elimination of hairs from hides and furs |
SU614142A1 (ru) * | 1976-09-30 | 1978-07-05 | Всесоюзный Научно-Исследовательский Институт Меховой Промышленности | Состав дл обработки кожевой ткани меховых шкур |
-
1979
- 1979-09-20 DE DE19792938078 patent/DE2938078A1/de not_active Withdrawn
-
1980
- 1980-08-08 US US06/176,684 patent/US4322210A/en not_active Expired - Lifetime
- 1980-09-09 DE DE8080105377T patent/DE3062049D1/de not_active Expired
- 1980-09-09 EP EP80105377A patent/EP0025933B1/fr not_active Expired
- 1980-09-19 JP JP12937580A patent/JPS5653200A/ja active Granted
- 1980-09-19 ES ES495201A patent/ES495201A0/es active Granted
- 1980-09-19 AU AU62547/80A patent/AU532669B2/en not_active Ceased
Non-Patent Citations (1)
Title |
---|
Keine Entgegenhaltungen. * |
Also Published As
Publication number | Publication date |
---|---|
DE2938078A1 (de) | 1981-04-09 |
ES8206629A1 (es) | 1982-08-16 |
EP0025933B1 (fr) | 1983-02-16 |
JPS5653200A (en) | 1981-05-12 |
AU532669B2 (en) | 1983-10-06 |
AU6254780A (en) | 1981-04-09 |
JPS6361999B2 (fr) | 1988-11-30 |
US4322210A (en) | 1982-03-30 |
DE3062049D1 (en) | 1983-03-24 |
ES495201A0 (es) | 1982-08-16 |
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Legal Events
Date | Code | Title | Description |
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PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
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AK | Designated contracting states |
Designated state(s): DE FR GB IT |
|
17P | Request for examination filed |
Effective date: 19810404 |
|
RBV | Designated contracting states (corrected) |
Designated state(s): DE FR GB IT |
|
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