DE1116401B - Verfahren zur Herstellung von haertbaren Kondensationsprodukten aus Melamin, Formaldehyd und substituierten Harnstoffen - Google Patents
Verfahren zur Herstellung von haertbaren Kondensationsprodukten aus Melamin, Formaldehyd und substituierten HarnstoffenInfo
- Publication number
- DE1116401B DE1116401B DEB57878A DEB0057878A DE1116401B DE 1116401 B DE1116401 B DE 1116401B DE B57878 A DEB57878 A DE B57878A DE B0057878 A DEB0057878 A DE B0057878A DE 1116401 B DE1116401 B DE 1116401B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- butanol
- melamine
- formaldehyde
- temperature
- 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
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title claims description 37
- 235000013877 carbamide Nutrition 0.000 title claims description 21
- 150000003672 ureas Chemical class 0.000 title claims description 20
- 229920000877 Melamine resin Polymers 0.000 title claims description 16
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 title claims description 16
- 239000007859 condensation product Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 60
- 229920005989 resin Polymers 0.000 claims description 19
- 239000011347 resin Substances 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 10
- 239000004202 carbamide Substances 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 8
- 230000007935 neutral effect Effects 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 37
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 21
- GJNDMSSZEBNLPU-UHFFFAOYSA-N octadecylurea Chemical compound CCCCCCCCCCCCCCCCCCNC(N)=O GJNDMSSZEBNLPU-UHFFFAOYSA-N 0.000 description 15
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical group COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 12
- 239000008098 formaldehyde solution Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 8
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- AOZVWUCYHOWWPH-UHFFFAOYSA-N 1,3-dioctadecylurea Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)NCCCCCCCCCCCCCCCCCC AOZVWUCYHOWWPH-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 235000013162 Cocos nucifera Nutrition 0.000 description 3
- 244000060011 Cocos nucifera Species 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 2
- -1 butoxyl groups Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- WRNOAELBRPKVHC-UHFFFAOYSA-N dodecylurea Chemical compound CCCCCCCCCCCCNC(N)=O WRNOAELBRPKVHC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
Classifications
-
- 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
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
- C08G12/34—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds and acyclic or carbocyclic compounds
- C08G12/36—Ureas; Thioureas
- C08G12/38—Ureas; Thioureas and melamines
-
- 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
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/40—Chemically modified polycondensates
- C08G12/42—Chemically modified polycondensates by etherifying
- C08G12/428—Chemically modified polycondensates by etherifying of polycondensates based on heterocyclic and acyclic or carbocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB57878A DE1116401B (de) | 1960-05-17 | 1960-05-17 | Verfahren zur Herstellung von haertbaren Kondensationsprodukten aus Melamin, Formaldehyd und substituierten Harnstoffen |
| CH553461A CH436712A (de) | 1960-05-17 | 1961-05-10 | Verfahren zur Herstellung von härtbaren Kondensationsprodukten |
| NL264810A NL134006C (nl) | 1960-05-17 | 1961-05-16 | Werkwijze voor het bereiden van hardbare condensatieprodukten |
| GB17741/61D GB914927A (en) | 1960-05-17 | 1961-05-16 | Hardenable condensation products and their production |
| FR862075A FR1290556A (fr) | 1960-05-17 | 1961-05-17 | Produits de condensation durcissables et procédé pour leur production |
| BE603923A BE603923A (fr) | 1960-05-17 | 1961-05-17 | Produits de condensation durcissables et procédé pour leur production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB57878A DE1116401B (de) | 1960-05-17 | 1960-05-17 | Verfahren zur Herstellung von haertbaren Kondensationsprodukten aus Melamin, Formaldehyd und substituierten Harnstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1116401B true DE1116401B (de) | 1961-11-02 |
Family
ID=6971865
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB57878A Pending DE1116401B (de) | 1960-05-17 | 1960-05-17 | Verfahren zur Herstellung von haertbaren Kondensationsprodukten aus Melamin, Formaldehyd und substituierten Harnstoffen |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE603923A (nl) |
| CH (1) | CH436712A (nl) |
| DE (1) | DE1116401B (nl) |
| FR (1) | FR1290556A (nl) |
| GB (1) | GB914927A (nl) |
| NL (1) | NL134006C (nl) |
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 (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR1005045B (el) * | 2004-11-15 | 2005-11-16 | Chimar (Hellas) Α.Ε. | Συνθεση θερμοσκληρυνομενων πολυμερων |
| WO2006051339A1 (en) * | 2004-11-15 | 2006-05-18 | Chimar Hellas Sa | Thermosetting polymer compositions |
-
1960
- 1960-05-17 DE DEB57878A patent/DE1116401B/de active Pending
-
1961
- 1961-05-10 CH CH553461A patent/CH436712A/de unknown
- 1961-05-16 GB GB17741/61D patent/GB914927A/en not_active Expired
- 1961-05-16 NL NL264810A patent/NL134006C/nl active
- 1961-05-17 BE BE603923A patent/BE603923A/fr unknown
- 1961-05-17 FR FR862075A patent/FR1290556A/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 |
|---|---|
| NL134006C (nl) | 1972-04-17 |
| FR1290556A (fr) | 1962-04-13 |
| NL264810A (nl) | 1964-06-10 |
| CH436712A (de) | 1967-05-31 |
| GB914927A (en) | 1963-01-09 |
| BE603923A (fr) | 1961-11-17 |
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