DE2451720A1 - Phenolsulfonsaeure-harnstoff-formaldehyd-umsetzungsprodukte, verfahren zu deren herstellung und ihre verwendung als gerbend wirkende substanzen - Google Patents
Phenolsulfonsaeure-harnstoff-formaldehyd-umsetzungsprodukte, verfahren zu deren herstellung und ihre verwendung als gerbend wirkende substanzenInfo
- Publication number
- DE2451720A1 DE2451720A1 DE19742451720 DE2451720A DE2451720A1 DE 2451720 A1 DE2451720 A1 DE 2451720A1 DE 19742451720 DE19742451720 DE 19742451720 DE 2451720 A DE2451720 A DE 2451720A DE 2451720 A1 DE2451720 A1 DE 2451720A1
- Authority
- DE
- Germany
- Prior art keywords
- component
- parts
- reaction
- reaction products
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 36
- 229920001807 Urea-formaldehyde Polymers 0.000 title claims description 6
- 239000000126 substance Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 66
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 35
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 32
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 28
- 239000010985 leather Substances 0.000 claims description 23
- 239000007859 condensation product Substances 0.000 claims description 22
- 239000000243 solution Substances 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 21
- 239000004202 carbamide Substances 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 20
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 12
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- 150000003672 ureas Chemical class 0.000 claims description 7
- QUWAJPZDCZDTJS-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfonylphenol Chemical group OC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1O QUWAJPZDCZDTJS-UHFFFAOYSA-N 0.000 claims description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 6
- -1 alkoxy radical Chemical class 0.000 claims description 6
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000007529 inorganic bases Chemical class 0.000 claims description 5
- 229920002866 paraformaldehyde Polymers 0.000 claims description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 claims description 4
- 229950005308 oxymethurea Drugs 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000005224 alkoxybenzenes Chemical class 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- UTBDUGHLQFNGEO-UHFFFAOYSA-N OC1=C(C=CC=C1)S(=O)(=O)O.OC1=C(C=CC=C1)S(=O)(=O)C1=C(C=CC=C1)O Chemical compound OC1=C(C=CC=C1)S(=O)(=O)O.OC1=C(C=CC=C1)S(=O)(=O)C1=C(C=CC=C1)O UTBDUGHLQFNGEO-UHFFFAOYSA-N 0.000 claims description 2
- 238000004061 bleaching Methods 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 239000008098 formaldehyde solution Substances 0.000 claims 2
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims 1
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 1
- 239000012084 conversion product Substances 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 238000009958 sewing Methods 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 125000001174 sulfone group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 229920001864 tannin Polymers 0.000 description 11
- 239000001648 tannin Substances 0.000 description 11
- 235000018553 tannin Nutrition 0.000 description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- 235000011121 sodium hydroxide Nutrition 0.000 description 9
- IULJSGIJJZZUMF-UHFFFAOYSA-N 2-hydroxybenzenesulfonic acid Chemical compound OC1=CC=CC=C1S(O)(=O)=O IULJSGIJJZZUMF-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 238000009833 condensation Methods 0.000 description 7
- 239000006188 syrup Substances 0.000 description 7
- 235000020357 syrup Nutrition 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 5
- 229940044654 phenolsulfonic acid Drugs 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N Lactic Acid Natural products CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000008240 homogeneous mixture Substances 0.000 description 3
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- CZWKJBLJZWMBNI-UHFFFAOYSA-N benzenesulfonoperoxoic acid Chemical compound OOS(=O)(=O)C1=CC=CC=C1 CZWKJBLJZWMBNI-UHFFFAOYSA-N 0.000 description 2
- 244000309466 calf Species 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- ORGWCTHQVYSUNL-UHFFFAOYSA-N 1,3-bis(hydroxymethyl)thiourea Chemical compound OCNC(=S)NCO ORGWCTHQVYSUNL-UHFFFAOYSA-N 0.000 description 1
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 1
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ZMZINYUKVRMNTG-UHFFFAOYSA-N acetic acid;formic acid Chemical compound OC=O.CC(O)=O ZMZINYUKVRMNTG-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 1
- CALBDOUFMLLGQH-UHFFFAOYSA-N hydroxymethylthiourea Chemical compound NC(=S)NCO CALBDOUFMLLGQH-UHFFFAOYSA-N 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 210000002445 nipple Anatomy 0.000 description 1
- 239000011022 opal Substances 0.000 description 1
- 230000010494 opalescence Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000004552 water soluble powder Substances 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
- C14C3/18—Chemical tanning by organic agents using polycondensation products or precursors thereof
- C14C3/20—Chemical tanning by organic agents using polycondensation products or precursors thereof sulfonated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
- C08G14/06—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols and monomers containing hydrogen attached to nitrogen
- C08G14/08—Ureas; Thioureas
Landscapes
- 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)
- Phenolic Resins Or Amino Resins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1571573 | 1973-11-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2451720A1 true DE2451720A1 (de) | 1975-05-15 |
Family
ID=4411334
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742451720 Pending DE2451720A1 (de) | 1973-11-08 | 1974-10-31 | Phenolsulfonsaeure-harnstoff-formaldehyd-umsetzungsprodukte, verfahren zu deren herstellung und ihre verwendung als gerbend wirkende substanzen |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4009996A (https=) |
| JP (1) | JPS5075693A (https=) |
| AR (1) | AR205801A1 (https=) |
| AT (1) | AT333931B (https=) |
| AU (1) | AU7510874A (https=) |
| BE (1) | BE821940A (https=) |
| BR (1) | BR7409361A (https=) |
| DE (1) | DE2451720A1 (https=) |
| FR (1) | FR2250778B1 (https=) |
| GB (1) | GB1465309A (https=) |
| NL (1) | NL7414543A (https=) |
| ZA (1) | ZA747157B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1416058A1 (de) * | 2002-10-28 | 2004-05-06 | Bayer Chemicals AG | Kondensationsprodukte zum Nachgerben von eisengegerbtem Leder |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH603796A5 (https=) * | 1976-04-22 | 1978-08-31 | Ciba Geigy Ag | |
| DE2834121C2 (de) * | 1978-08-03 | 1980-08-21 | Bayer Ag, 5090 Leverkusen | Kondensationsprodukte aus Terphenylsulfonsäuren, Naphthalinsulfonsäuren, Bis-(4-hydroxyphenyl)-sulfon und Formaldehyd |
| DE4014977A1 (de) * | 1990-05-10 | 1991-11-14 | Basf Ag | Kondensationsprodukte aus phenolmonosulfonsaeuren, dihydroxydiphenylsulfonen, harnstoff und formaldehyd |
| CA2034746C (en) * | 1991-01-22 | 1997-11-18 | Edward William Robins | Method of neutralizing hazardous products and composition therefor |
| DE4118007A1 (de) * | 1991-06-01 | 1992-12-03 | Basf Ag | Kondensationsprodukte aus sulfonierten phenolen, harnstoff, weiteren organischen stickstoff-basen und formaldehyd und ihre verwendung als gerbstoffe und als spruehhilfsmittel fuer redispergierbare polymerpulver |
| US5534611A (en) * | 1993-10-29 | 1996-07-09 | Nalco Chemical Company | Sulfonated and carboxylated aminoethylenephosphonic acid and aminobis (methylene) phosphinic acid |
| EP0717114A3 (de) * | 1994-12-15 | 1996-08-21 | Ciba Geigy Ag | Wässrige Zusammensetzung zum Vorgerben von Hautblössen oder Nachgerben von Leder |
| PT2714756T (pt) | 2011-06-02 | 2018-07-16 | Lanxess Deutschland Gmbh | Polímeros de enxerto à base de polissacárido e/ou polipéptido como taninos sintéticos |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2129553A (en) * | 1938-09-06 | Tanning material | ||
| US2127068A (en) * | 1934-05-11 | 1938-08-16 | Geigy Ag J R | Manufacture of tanning agents |
| US2271245A (en) * | 1938-06-09 | 1942-01-27 | Geigy Ag J R | Manufacture of tanning substances |
| GB683084A (en) * | 1949-06-20 | 1952-11-19 | Geigy Ag J R | Manufacture of new condensation products, being more especially improved tanning agents and their application |
| US2716098A (en) * | 1951-02-13 | 1955-08-23 | Geigy Ag J R | Water soluble condensation products with a tanning action |
| US2809088A (en) * | 1952-07-12 | 1957-10-08 | Bayer Ag | Process of retanning leather with a condensation product of sulfones of monohydric phenols, non-aromatic amines and formaldehyde |
| US3010779A (en) * | 1958-03-22 | 1961-11-28 | Bayer Ag | Production of shrunk leather |
| US3475113A (en) * | 1962-09-27 | 1969-10-28 | Diamond Shamrock Corp | Process for treatment of leather with condensates of aminoplast-sulfonated phenolic compounds |
| CA980512A (en) * | 1971-11-26 | 1975-12-30 | Badische Anilin- And Soda-Fabrik Aktiengesellschaft | Tanning agents |
-
1974
- 1974-01-01 AR AR256440A patent/AR205801A1/es active
- 1974-10-31 DE DE19742451720 patent/DE2451720A1/de active Pending
- 1974-11-05 US US05/520,995 patent/US4009996A/en not_active Expired - Lifetime
- 1974-11-06 FR FR7436758A patent/FR2250778B1/fr not_active Expired
- 1974-11-07 ZA ZA00747157A patent/ZA747157B/xx unknown
- 1974-11-07 BE BE150285A patent/BE821940A/xx unknown
- 1974-11-07 GB GB4824074A patent/GB1465309A/en not_active Expired
- 1974-11-07 AT AT892274A patent/AT333931B/de not_active IP Right Cessation
- 1974-11-07 NL NL7414543A patent/NL7414543A/xx unknown
- 1974-11-07 BR BR9361/74A patent/BR7409361A/pt unknown
- 1974-11-07 AU AU75108/74A patent/AU7510874A/en not_active Expired
- 1974-11-08 JP JP49128139A patent/JPS5075693A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1416058A1 (de) * | 2002-10-28 | 2004-05-06 | Bayer Chemicals AG | Kondensationsprodukte zum Nachgerben von eisengegerbtem Leder |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA747157B (en) | 1975-12-31 |
| BR7409361A (pt) | 1976-05-18 |
| GB1465309A (en) | 1977-02-23 |
| AU7510874A (en) | 1976-05-13 |
| FR2250778A1 (https=) | 1975-06-06 |
| US4009996A (en) | 1977-03-01 |
| AT333931B (de) | 1976-12-27 |
| JPS5075693A (https=) | 1975-06-20 |
| ATA892274A (de) | 1976-04-15 |
| USB520995I5 (https=) | 1976-03-23 |
| NL7414543A (nl) | 1975-05-12 |
| BE821940A (fr) | 1975-05-07 |
| AR205801A1 (es) | 1976-06-07 |
| FR2250778B1 (https=) | 1977-03-25 |
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