DE2133820B2 - Verfahren zur herstellung von niedermolekularen, veraetherten methylolharnstoffen bzw. -thioharnstoffen - Google Patents
Verfahren zur herstellung von niedermolekularen, veraetherten methylolharnstoffen bzw. -thioharnstoffenInfo
- Publication number
- DE2133820B2 DE2133820B2 DE19712133820 DE2133820A DE2133820B2 DE 2133820 B2 DE2133820 B2 DE 2133820B2 DE 19712133820 DE19712133820 DE 19712133820 DE 2133820 A DE2133820 A DE 2133820A DE 2133820 B2 DE2133820 B2 DE 2133820B2
- Authority
- DE
- Germany
- Prior art keywords
- urea
- thiourea
- formaldehyde
- reaction
- mol
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 50
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 35
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 22
- 239000004202 carbamide Substances 0.000 claims description 16
- VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical compound NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 239000008098 formaldehyde solution Substances 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 235000013877 carbamide Nutrition 0.000 description 12
- 239000000243 solution Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 5
- -1 polymethylene Polymers 0.000 description 5
- 239000000123 paper Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 229920001807 Urea-formaldehyde Polymers 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 229920003180 amino resin Polymers 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000004848 polyfunctional curative Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 150000003585 thioureas Chemical class 0.000 description 2
- PZVRLLPBKIJQBK-UHFFFAOYSA-N COCC(NC(=O)N)NC(=O)N Chemical compound COCC(NC(=O)N)NC(=O)N PZVRLLPBKIJQBK-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004849 alkoxymethyl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011093 chipboard Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- CALBDOUFMLLGQH-UHFFFAOYSA-N hydroxymethylthiourea Chemical compound NC(=S)NCO CALBDOUFMLLGQH-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 150000005217 methyl ethers Chemical class 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 238000009988 textile finishing Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/06—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
- C07C335/08—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety
- C07C273/1863—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety from urea
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712133820 DE2133820B2 (de) | 1971-07-07 | 1971-07-07 | Verfahren zur herstellung von niedermolekularen, veraetherten methylolharnstoffen bzw. -thioharnstoffen |
| NL7208770A NL7208770A (enExample) | 1971-07-07 | 1972-06-26 | |
| CS455872A CS157148B2 (enExample) | 1971-07-07 | 1972-06-27 | |
| US268810A US3859351A (en) | 1971-07-07 | 1972-07-03 | Preparation of low molecular weight etherified methylol ureas and thioureas |
| DD164179A DD99571A5 (enExample) | 1971-07-07 | 1972-07-04 | |
| GB3172072A GB1360897A (en) | 1971-07-07 | 1972-07-06 | Preparation of low molecular weight etherified methylol ureas and thioureas |
| FR7224459A FR2144838B1 (enExample) | 1971-07-07 | 1972-07-06 | |
| AT580272A AT332123B (de) | 1971-07-07 | 1972-07-06 | Verfahren zur herstellung von niedermolekularen, veratherten methylolharnstoffen bzw. -thioharnstoffen |
| ZA724659A ZA724659B (en) | 1971-07-07 | 1972-07-06 | Preparation of low molecular weight etherified methylol ureas and thioureas |
| IT26706/72A IT964538B (it) | 1971-07-07 | 1972-07-06 | Processo per la preparazione di metilol uree o metilol tiouree eterificate a basso peso molecolare |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712133820 DE2133820B2 (de) | 1971-07-07 | 1971-07-07 | Verfahren zur herstellung von niedermolekularen, veraetherten methylolharnstoffen bzw. -thioharnstoffen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2133820A1 DE2133820A1 (de) | 1973-01-25 |
| DE2133820B2 true DE2133820B2 (de) | 1977-09-15 |
Family
ID=5812948
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712133820 Withdrawn DE2133820B2 (de) | 1971-07-07 | 1971-07-07 | Verfahren zur herstellung von niedermolekularen, veraetherten methylolharnstoffen bzw. -thioharnstoffen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3859351A (enExample) |
| AT (1) | AT332123B (enExample) |
| CS (1) | CS157148B2 (enExample) |
| DD (1) | DD99571A5 (enExample) |
| DE (1) | DE2133820B2 (enExample) |
| FR (1) | FR2144838B1 (enExample) |
| GB (1) | GB1360897A (enExample) |
| IT (1) | IT964538B (enExample) |
| NL (1) | NL7208770A (enExample) |
| ZA (1) | ZA724659B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3743539A1 (de) * | 1987-12-22 | 1989-07-06 | Pfersee Chem Fab | Verfahren zur herstellung von veretherten methylolalkylharnstoffen, die daraus hergestellten dispersionen und deren verwendung |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3985802A (en) * | 1965-10-22 | 1976-10-12 | Standard Oil Company (Indiana) | Lubricating oils containing high molecular weight Mannich condensation products |
| JPS52112665A (en) * | 1976-03-17 | 1977-09-21 | Bridgestone Tire Co Ltd | Polyurethane foammmoulding by hot comression |
| DE2757582A1 (de) * | 1977-12-23 | 1979-06-28 | Cassella Ag | Verfahren zur herstellung lagerstabiler waessriger emulsionen von n.alkyl-n'-alkylol-harnstoffen und deren anwendung zum weichmachen von leder und textilmaterial |
| DE3528735A1 (de) * | 1985-08-10 | 1987-02-12 | Sueddeutsche Kalkstickstoff | Schnellhaertendes kondensationsprodukt und verfahren zur herstellung |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1963762A (en) * | 1929-12-06 | 1934-06-19 | Ig Farbenindustrie Ag | Production of artificial masses |
| US2315745A (en) * | 1940-07-23 | 1943-04-06 | Du Pont | Preparation of lower alkyl ethers of methylolurea |
| US2825710A (en) * | 1956-02-20 | 1958-03-04 | Du Pont | Process of preparing a grease-proofing agent |
| US2859206A (en) * | 1956-07-11 | 1958-11-04 | American Cyanamid Co | Thiourea and urea-formaldehyde mixed resins |
-
1971
- 1971-07-07 DE DE19712133820 patent/DE2133820B2/de not_active Withdrawn
-
1972
- 1972-06-26 NL NL7208770A patent/NL7208770A/xx unknown
- 1972-06-27 CS CS455872A patent/CS157148B2/cs unknown
- 1972-07-03 US US268810A patent/US3859351A/en not_active Expired - Lifetime
- 1972-07-04 DD DD164179A patent/DD99571A5/xx unknown
- 1972-07-06 ZA ZA724659A patent/ZA724659B/xx unknown
- 1972-07-06 IT IT26706/72A patent/IT964538B/it active
- 1972-07-06 GB GB3172072A patent/GB1360897A/en not_active Expired
- 1972-07-06 AT AT580272A patent/AT332123B/de not_active IP Right Cessation
- 1972-07-06 FR FR7224459A patent/FR2144838B1/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3743539A1 (de) * | 1987-12-22 | 1989-07-06 | Pfersee Chem Fab | Verfahren zur herstellung von veretherten methylolalkylharnstoffen, die daraus hergestellten dispersionen und deren verwendung |
Also Published As
| Publication number | Publication date |
|---|---|
| DD99571A5 (enExample) | 1973-08-12 |
| NL7208770A (enExample) | 1973-01-09 |
| DE2133820A1 (de) | 1973-01-25 |
| GB1360897A (en) | 1974-07-24 |
| CS157148B2 (enExample) | 1974-08-23 |
| FR2144838A1 (enExample) | 1973-02-16 |
| ATA580272A (de) | 1975-03-15 |
| IT964538B (it) | 1974-01-31 |
| US3859351A (en) | 1975-01-07 |
| FR2144838B1 (enExample) | 1977-07-22 |
| ZA724659B (en) | 1973-04-25 |
| AT332123B (de) | 1976-09-10 |
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| DED0014199MA (enExample) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BHJ | Nonpayment of the annual fee |