US3650666A - Tanning and fat liquoring method - Google Patents
Tanning and fat liquoring method Download PDFInfo
- Publication number
- US3650666A US3650666A US730660A US3650666DA US3650666A US 3650666 A US3650666 A US 3650666A US 730660 A US730660 A US 730660A US 3650666D A US3650666D A US 3650666DA US 3650666 A US3650666 A US 3650666A
- Authority
- US
- United States
- Prior art keywords
- tanning
- fat
- liquoring
- long
- compound
- 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
- 238000000034 method Methods 0.000 title claims abstract description 54
- 239000003795 chemical substances by application Substances 0.000 claims description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- -1 phenolic carboxylic acids Chemical class 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 17
- 244000226021 Anacardium occidentale Species 0.000 claims description 15
- 235000020226 cashew nut Nutrition 0.000 claims description 15
- 239000007788 liquid Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- KVVSCMOUFCNCGX-UHFFFAOYSA-N cardol Chemical compound CCCCCCCCCCCCCCCC1=CC(O)=CC(O)=C1 KVVSCMOUFCNCGX-UHFFFAOYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
- DXRKLUVKXMAMOV-UHFFFAOYSA-N 3-heptadecylcatechol Chemical compound CCCCCCCCCCCCCCCCCC1=CC=CC(O)=C1O DXRKLUVKXMAMOV-UHFFFAOYSA-N 0.000 claims description 6
- RMTXUPIIESNLPW-UHFFFAOYSA-N 1,2-dihydroxy-3-(pentadeca-8,11-dienyl)benzene Natural products CCCC=CCC=CCCCCCCCC1=CC=CC(O)=C1O RMTXUPIIESNLPW-UHFFFAOYSA-N 0.000 claims description 5
- QARRXYBJLBIVAK-UEMSJJPVSA-N 3-[(8e,11e)-pentadeca-8,11-dienyl]benzene-1,2-diol;3-[(8e,11e)-pentadeca-8,11,14-trienyl]benzene-1,2-diol;3-[(8e,11e,13e)-pentadeca-8,11,13-trienyl]benzene-1,2-diol;3-[(e)-pentadec-8-enyl]benzene-1,2-diol;3-pentadecylbenzene-1,2-diol Chemical compound CCCCCCCCCCCCCCCC1=CC=CC(O)=C1O.CCCCCC\C=C\CCCCCCCC1=CC=CC(O)=C1O.CCC\C=C\C\C=C\CCCCCCCC1=CC=CC(O)=C1O.C\C=C\C=C\C\C=C\CCCCCCCC1=CC=CC(O)=C1O.OC1=CC=CC(CCCCCCC\C=C\C\C=C\CC=C)=C1O QARRXYBJLBIVAK-UEMSJJPVSA-N 0.000 claims description 5
- IYROWZYPEIMDDN-UHFFFAOYSA-N 3-n-pentadec-8,11,13-trienyl catechol Natural products CC=CC=CCC=CCCCCCCCC1=CC=CC(O)=C1O IYROWZYPEIMDDN-UHFFFAOYSA-N 0.000 claims description 5
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims description 5
- KAOMOVYHGLSFHQ-UTOQUPLUSA-N anacardic acid Chemical compound CCC\C=C/C\C=C/CCCCCCCC1=CC=CC(O)=C1C(O)=O KAOMOVYHGLSFHQ-UTOQUPLUSA-N 0.000 claims description 5
- 235000014398 anacardic acid Nutrition 0.000 claims description 5
- ADFWQBGTDJIESE-UHFFFAOYSA-N anacardic acid 15:0 Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1C(O)=O ADFWQBGTDJIESE-UHFFFAOYSA-N 0.000 claims description 5
- UFMJCOLGRWKUKO-UHFFFAOYSA-N cardol diene Natural products CCCC=CCC=CCCCCCCCC1=CC(O)=CC(O)=C1 UFMJCOLGRWKUKO-UHFFFAOYSA-N 0.000 claims description 5
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 claims description 5
- DQTMTQZSOJMZSF-UHFFFAOYSA-N urushiol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1O DQTMTQZSOJMZSF-UHFFFAOYSA-N 0.000 claims description 5
- JOLVYUIAMRUBRK-UHFFFAOYSA-N 11',12',14',15'-Tetradehydro(Z,Z-)-3-(8-Pentadecenyl)phenol Natural products OC1=CC=CC(CCCCCCCC=CCC=CCC=C)=C1 JOLVYUIAMRUBRK-UHFFFAOYSA-N 0.000 claims description 4
- YLKVIMNNMLKUGJ-UHFFFAOYSA-N 3-Delta8-pentadecenylphenol Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1 YLKVIMNNMLKUGJ-UHFFFAOYSA-N 0.000 claims description 4
- JOLVYUIAMRUBRK-UTOQUPLUSA-N Cardanol Chemical compound OC1=CC=CC(CCCCCCC\C=C/C\C=C/CC=C)=C1 JOLVYUIAMRUBRK-UTOQUPLUSA-N 0.000 claims description 4
- FAYVLNWNMNHXGA-UHFFFAOYSA-N Cardanoldiene Natural products CCCC=CCC=CCCCCCCCC1=CC=CC(O)=C1 FAYVLNWNMNHXGA-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- PTFIPECGHSYQNR-UHFFFAOYSA-N cardanol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 abstract description 5
- 241001465754 Metazoa Species 0.000 abstract description 3
- 238000012545 processing Methods 0.000 abstract description 2
- 239000010985 leather Substances 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 235000013824 polyphenols Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000010697 neat foot oil Substances 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 235000018553 tannin Nutrition 0.000 description 2
- 239000001648 tannin Substances 0.000 description 2
- 229920001864 tannin Polymers 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 101100264195 Caenorhabditis elegans app-1 gene Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010016322 Feeling abnormal Diseases 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- 235000019687 Lamb Nutrition 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229940037003 alum Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000001183 hydrocarbyl group Chemical class 0.000 description 1
- UODXCYZDMHPIJE-UHFFFAOYSA-N menthanol Chemical compound CC1CCC(C(C)(C)O)CC1 UODXCYZDMHPIJE-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 125000001874 trioxidanyl group Chemical group [*]OOO[H] 0.000 description 1
- 235000013311 vegetables Nutrition 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
- C14C3/00—Tanning; Compositions for tanning
- C14C3/02—Chemical tanning
- C14C3/08—Chemical tanning by organic agents
- C14C3/14—Fat tanning; Oil tanning
Definitions
- a phenolic compound having a long-chain alkyl radical or a long-chain alkenyl radical is used as a tanning and fat-liquoring agent in addition to ordinary tanning agents in tanning of hides and skins.
- This invention relates generally to the art of processing animal hides and skins and more particularly to a new and improved method and fat liquoring agents for tanning hides and skins.
- fat-liquoring and stuffing agents (hereinafter referred to as fat-liquoring agents) used heretofore have invariably been of the fatty oil type or of the type containing synthetic, hydrocarbon chain derivatives, whereby these fat-liquoring agents have had a tendency to be readily desorbed from the hides and skins. Consequently, tanned leathers thus produced have often had the disadvantageous tendency of hardening during use and readily developing cracks.
- an object of the invention is to provide a group of new fat-liquoring agents to be .used with ordinary tanning agents to produce leather, which fat-liquoring agents have substantial tanning effect in addition to their excellent fat-liquoring effects, and which, as fat-liquoring agents, are not readily desorbed from the finished leather.
- a tannable fat-liquoring agent containing as its principal component a phenolic compound having a longchain alkyl radical or a long-chain alkenyl radical attached thereto.
- a method for tanning hides and skins with the ordinary tanning agents which method is characterized by the-use of, in addition to the ordinary tanning agents, a tannable fat-liquoring agent as designated above and as described more fully hereinafter.
- a feature of the method of the invention lies in the use of compounds such as monovalent or bivalent long-chain alkylor long-chain alkenylphenols and long-chain alkylor longchain alkenyl-phenol having a carboxyl group as tannable fat-liquoring agents as described more fully hereinafter, These compounds can be represented by the following general formula.
- R represents a long-chain alkyl radical or a long-chain alkenyl radical.
- Examples of compounds corresponding to the above represented compound form are octylphenol and nonylphenol among those produced synthetically and cashew nut shell liquids, urushiol, and laccol among those obtained naturally.
- cashew nut shell liquids there is the class obtained by cold pressing or by solvent extraction and the class obtained by heat elution.
- the former class contains anacardic acid as the principal component and also approximately 10 percent of cardol, which is a bivalent phenol-derivative.
- the fat-liquoring agent used in the process according to the invention is invariably a phenolic compound having a long-chain alkyl radical or alkenyl radical.
- the phenolic radical OH is linked with the active group (with) in the proteins which are constituents of a hide or skin to accomplish tanning, and, at the same time, the long-chain alkyl or alkenyl radical functions as a fat-liquoring agent to cause softening of the hide or skin.
- a COOH radical when a COOH radical is present, it forms a strong complex compound with the chromium in chrome leather and remains for a long time in the leather without separating therefrom.
- the fat-liquoring agent used in the process of the invention differing from those used heretofore, exhibits not only a fat-liquoring effect but also a tanning effect with respect to hides and skins. Therefore, it may be more appropriate to call this agent as a tannable fat-liquoring agent.” Practical use of such tannable fat-liquoring agents has been made possible for the first time by the present invention.
- a tannable fat-liquoring agent according to the invention is capable of effectively accomplishing both tanning and fat-liquoring as described above, it can be used in a step of a fat-luquoring process stop subsequent to an ordinary tanning, or it may be mixed with an ordinary tanning agent and used in one process step to accomplish simultaneously both tanning and fat-liquoring.
- the use of this tannable fat-liquoring agent in a separate fat-liquoring step and its mixed use as a tanning agent are herein referred to generically by the term joint use.
- a phenolic carboxylic acid having a long-chain alkyl radical or a long-chain alkenyl radical as, for example, a cashew nut shell liquid (cold pressed) which has not yet been decarboxylated and contains anacardic acid as the main constituent, can be rendered soluble in water by converting it to a basic salt of sodium, potassium, organic amines, and ammonia.
- a length greater than that corresponding to C is preferably for the alkyl or alkenyl radical which is a side chain of the phenolic compound.
- the use ofthe tannable fat-liquoring agent of the invention as a fat-liquoring agent in a tanning process produces results which have been found to be superior to those attainable through the use of conventional fat-liquoring agents. More specifically, improvements in swelling or plumpness and hand feeling, increase in smoothness of the grain side (or hair side), prevention of poor hide, increase in the fullness of belly, and other desirable results are attained, and, moreover, washable leathers oflow trichlene extraction quantity can be produced.
- a fat-liquoring composition material suitable for use according to the invention was prepared by adding 250 grammes (g.) of methanol to g. of nonylphenol and 300 g. ofa decarboxylated cashew nut shell liquid, adding by dropping 350 g. of a lO-percent aqueous solution of sodium hydroxide to the resulting process batch as the batch was maintained at a temperature of degrees C. and agitated, and continuing the agitation at the same temperature for 30 minutes after completion ofthe dropping.
- a fat-liquoring composition suitable for use according to the invention was prepared by adding 200 g. of methanol to 300 g. of a cashew nut shell liquid which had not been decarboxylated, 30 g. of a decarboxylated cashew nut shell liquid, and 50 g. of urushiol, dropping 75 g. of triethanolamine and 40 g. of a lO-percent aqueous solution of sodium hydroxide into the resulting process batch as it was maintained at a temperature of 60 degrees C. and agitated, and maintaining the resulting batch at the same temperature for seven hours after completion of the dropping step.
- fur pelts which had been subjected respectively to formalin tanning and alum tanning were coated on their flesh sides, after surplus water had been drained off, with a fatliquoring agent consisting of a mixture of 100 parts of the afore-described fat-liquoring composition and 5O parts of octylphenol and were dumped for 24 hours with their flesh sides in mutual contact. Thereafter, the pelts were air dried and seasoned and staked by conventional methods whereupon a fur of excellent soft feeling was obtained.
- a fat-liquoring composition for use according to the invention was prepared by adding five g. of Noigen EA-15l (a nonionic surface active agent manufactured by Daiichi Kohgyoh Seiyaku K.K., Japan) at room temperature to 500 g. of an undecarboxylated cashew nut shell liquid and thoroughly mixing the resulting mixture.
- Noigen EA-15l a nonionic surface active agent manufactured by Daiichi Kohgyoh Seiyaku K.K., Japan
- the conventional method comprised chrome tanning the hide by an ordinary procedure and then treating the hide with sulphonated neats foot oil as a fat-liquoring agent.
- a method of tanning hides and skins to prepare a leather material which comprises employing in the tanning process, and in addition to the ordinary tanning agents, a fat-Iiquoring step utilizing a compound of the formula R (C 0.0H)m
- R is a long-chain-alkyl radical or a long-chain alkenyl radical, is l or 2 and m is 0 or 1.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3728567 | 1967-06-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3650666A true US3650666A (en) | 1972-03-21 |
Family
ID=12493417
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US730660A Expired - Lifetime US3650666A (en) | 1967-06-13 | 1968-05-20 | Tanning and fat liquoring method |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3650666A (enExample) |
| FR (1) | FR1577502A (enExample) |
| GB (1) | GB1225805A (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3953163A (en) * | 1974-03-08 | 1976-04-27 | Sandoz Ltd. | Improvements in or relating to organic compounds |
| US4074968A (en) * | 1976-04-15 | 1978-02-21 | Diamond Shamrock Corporation | Retanning and fatliquoring agent |
| CN104726623A (zh) * | 2013-12-24 | 2015-06-24 | 佛山市顺德区龙亭新材料有限公司 | 一种具有除甲醛功能的加脂剂及其制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2205950A (en) * | 1935-09-25 | 1940-06-25 | Nat Aniline & Chem Co Inc | Emulsions, suspensions, and like dispersions |
| CA464443A (en) * | 1950-04-18 | H. Stumpf Jacob | Fatliquoring alum-containing leather | |
| US3102772A (en) * | 1956-03-30 | 1963-09-03 | Du Pont | Process of after-tanning with chromium werner type complex |
-
1968
- 1968-05-20 US US730660A patent/US3650666A/en not_active Expired - Lifetime
- 1968-06-11 FR FR1577502D patent/FR1577502A/fr not_active Expired
- 1968-06-11 GB GB1225805D patent/GB1225805A/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA464443A (en) * | 1950-04-18 | H. Stumpf Jacob | Fatliquoring alum-containing leather | |
| US2205950A (en) * | 1935-09-25 | 1940-06-25 | Nat Aniline & Chem Co Inc | Emulsions, suspensions, and like dispersions |
| US3102772A (en) * | 1956-03-30 | 1963-09-03 | Du Pont | Process of after-tanning with chromium werner type complex |
Non-Patent Citations (1)
| Title |
|---|
| Merck Index, 7th Edition, 1960, p. 77 (Anacardic Acid) and page 1085 (Urushiol). * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3953163A (en) * | 1974-03-08 | 1976-04-27 | Sandoz Ltd. | Improvements in or relating to organic compounds |
| US4074968A (en) * | 1976-04-15 | 1978-02-21 | Diamond Shamrock Corporation | Retanning and fatliquoring agent |
| CN104726623A (zh) * | 2013-12-24 | 2015-06-24 | 佛山市顺德区龙亭新材料有限公司 | 一种具有除甲醛功能的加脂剂及其制备方法 |
| CN104726623B (zh) * | 2013-12-24 | 2017-01-04 | 佛山市顺德区龙亭新材料有限公司 | 一种具有除甲醛功能的加脂剂及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1577502A (enExample) | 1969-08-08 |
| GB1225805A (enExample) | 1971-03-24 |
| DE1769587A1 (de) | 1970-12-03 |
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