GB595211A - Manufacture of condensation products having a tanning action from dihydroxy-diphenyl and dihydroxy-ditolyl sulphones - Google Patents
Manufacture of condensation products having a tanning action from dihydroxy-diphenyl and dihydroxy-ditolyl sulphonesInfo
- Publication number
- GB595211A GB595211A GB10643/45A GB1064345A GB595211A GB 595211 A GB595211 A GB 595211A GB 10643/45 A GB10643/45 A GB 10643/45A GB 1064345 A GB1064345 A GB 1064345A GB 595211 A GB595211 A GB 595211A
- Authority
- GB
- United Kingdom
- Prior art keywords
- mixture
- urea
- acid
- formaldehyde
- sulphone
- 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
Links
- 125000001174 sulfone group Chemical group 0.000 title abstract 8
- 239000007859 condensation product Substances 0.000 title abstract 6
- 239000004305 biphenyl Substances 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 26
- 239000000203 mixture Substances 0.000 abstract 15
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 12
- 239000004202 carbamide Substances 0.000 abstract 12
- 239000002253 acid Substances 0.000 abstract 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 6
- 239000000047 product Substances 0.000 abstract 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 235000019253 formic acid Nutrition 0.000 abstract 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 238000007792 addition Methods 0.000 abstract 2
- 229930003836 cresol Natural products 0.000 abstract 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract 2
- 150000007524 organic acids Chemical class 0.000 abstract 2
- 238000003756 stirring Methods 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 238000010790 dilution Methods 0.000 abstract 1
- 239000012895 dilution Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000007689 inspection Methods 0.000 abstract 1
- 239000000155 melt Substances 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 abstract 1
- 229950005308 oxymethurea Drugs 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Products having tanning properties in acid medium are made by condensing a mixture of 1 mol. of a dihydroxy-diphenyl- or dihydroxy-ditolyl-sulphone and 1-5 mols. of a dihydroxy-diphenyl or dihydroxy-di-tolyl sulphone sulphonic acid in an acid medium with urea and formaldehyde or with an intermediate condensation product of urea and formaldehyde, for example, a condensation product, for instance, dimethylol urea, obtainable by heating a mixture of 1 mol. of urea to 2 mols. of formaldehyde in a neutral or weakly alkaline medium. Preferably, 1/2 -1 molecular proportion of urea, or of the intermediate condensation product of urea and formaldehyde is used for each molecular proportion of the sulphone mixture, such proportions yielding a product soluble in acid medium. The mixture of sulphone and sulphonic acid may be made by partially sulphonating the sulphone or mixture of sulphones. In examples: (1) 4 : 41-dihydroxy-diphenyl sulphone is sulphonated to the extent of 60 per cent with sulphuric acid, the melt then diluted and urea dissolved in it, and formaldehyde added at 45-50 DEG C. and the mixture stirred for 20 hours, the product being then neutralized and made weakly acid with formic acid. A similar product results by partially neutralizing the sulphonation mixture with ammonia and then condensing at 55-60 DEG C. for 20 hours; (2) a sulphonation mixture prepared as in (1) after cooling and dilution is mixed with a condensation product obtained by boiling urea and formaldehyde in weakly alkaline medium for half an hour, and the mixture is then kept at 45-50 DEG C. for 17 hours and neutralized and acidified with an organic acid; (3) a sulphonation mixture prepared as in example (1) is mixed with dimethyl-dihydroxy-diphenyl sulphone (prepared from crude cresol) and urea is added followed by formaldehyde. The mixture is heated at 45-50 DEG C. for 18 hours and then rendered weakly acid with formic acid; (4) the sulphone prepared from crude cresol is partially sulphonated, and a solution of urea in formalin added in two parts, with stirring for 2 hours at 45-50 DEG C. between the two additions followed by further stirring for 18 hours at this temperature. The product is then made acid with an organic acid; (5) a sulphonation mixture prepared as in example (1) has added a mixture of urea and biuret, followed by the slow addition of formaldehyde, and the mixture is heated at 45-50 DEG C. for 18 hours and made weakly acid with formic or acetic acid. The Specification as open to inspection under Sect. 91 describes the products obtained by condensing a mixture of di-hydroxy di-aryl sulphone and di-hydroxy di-aryl sulphone sulphonic acid in an acid medium with urea and formaldehyde or with a condensation product of urea and formaldehyde. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH595211X | 1944-04-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB595211A true GB595211A (en) | 1947-11-28 |
Family
ID=4522390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB10643/45A Expired GB595211A (en) | 1944-04-28 | 1945-04-27 | Manufacture of condensation products having a tanning action from dihydroxy-diphenyl and dihydroxy-ditolyl sulphones |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB595211A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4325890A (en) * | 1979-08-30 | 1982-04-20 | Bayer Aktiengesellschaft | Phenol-formaldehyde condensates, their preparation and their use as dispersing agents, liquefaction agents and tanning agents |
-
1945
- 1945-04-27 GB GB10643/45A patent/GB595211A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4325890A (en) * | 1979-08-30 | 1982-04-20 | Bayer Aktiengesellschaft | Phenol-formaldehyde condensates, their preparation and their use as dispersing agents, liquefaction agents and tanning agents |
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