DE2222025A1 - Verfahren zur herstellung von pulverfoermigem n-alkoxymethyl-polylaurinlactam bzw. polyundecansaeureamid mit mindestens 50 % n-alkoxymethylgruppen - Google Patents
Verfahren zur herstellung von pulverfoermigem n-alkoxymethyl-polylaurinlactam bzw. polyundecansaeureamid mit mindestens 50 % n-alkoxymethylgruppenInfo
- Publication number
- DE2222025A1 DE2222025A1 DE19722222025 DE2222025A DE2222025A1 DE 2222025 A1 DE2222025 A1 DE 2222025A1 DE 19722222025 DE19722222025 DE 19722222025 DE 2222025 A DE2222025 A DE 2222025A DE 2222025 A1 DE2222025 A1 DE 2222025A1
- Authority
- DE
- Germany
- Prior art keywords
- alkoxymethyl
- polylaurolactam
- polyamide
- alcohol
- production
- 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 15
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 150000001408 amides Chemical class 0.000 title claims description 8
- 150000003951 lactams Chemical class 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 66
- 239000004952 Polyamide Substances 0.000 claims description 35
- 229920002647 polyamide Polymers 0.000 claims description 35
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 31
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 20
- 229920000299 Nylon 12 Polymers 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 10
- 230000001476 alcoholic effect Effects 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 5
- 125000005521 carbonamide group Chemical group 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- -1 aliphatic alcohols Chemical class 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 239000008098 formaldehyde solution Substances 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 4
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000002245 particle Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000006467 substitution reaction Methods 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000008187 granular material Substances 0.000 description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- SQYNKIJPMDEDEG-UHFFFAOYSA-N paraldehyde Chemical compound CC1OC(C)OC(C)O1 SQYNKIJPMDEDEG-UHFFFAOYSA-N 0.000 description 3
- 229960003868 paraldehyde Drugs 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- OLBVUFHMDRJKTK-UHFFFAOYSA-N [N].[O] Chemical compound [N].[O] OLBVUFHMDRJKTK-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- RTWLTPNIXGIVRS-UHFFFAOYSA-N azanium;propan-2-one;hydroxide Chemical compound N.O.CC(C)=O RTWLTPNIXGIVRS-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002373 hemiacetals Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- VHWYCFISAQVCCP-UHFFFAOYSA-N methoxymethanol Chemical compound COCO VHWYCFISAQVCCP-UHFFFAOYSA-N 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/48—Polymers modified by chemical after-treatment
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722222025 DE2222025A1 (de) | 1972-05-05 | 1972-05-05 | Verfahren zur herstellung von pulverfoermigem n-alkoxymethyl-polylaurinlactam bzw. polyundecansaeureamid mit mindestens 50 % n-alkoxymethylgruppen |
| FR7315172A FR2183722A1 (en) | 1972-05-05 | 1973-04-26 | N-alkoxymethyl-polylaurolactam or -polyundecanoamide - with high degree of substitution in free running powder form |
| JP5057673A JPS5239637B2 (enrdf_load_html_response) | 1972-05-05 | 1973-05-07 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722222025 DE2222025A1 (de) | 1972-05-05 | 1972-05-05 | Verfahren zur herstellung von pulverfoermigem n-alkoxymethyl-polylaurinlactam bzw. polyundecansaeureamid mit mindestens 50 % n-alkoxymethylgruppen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2222025A1 true DE2222025A1 (de) | 1973-11-15 |
Family
ID=5844127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722222025 Pending DE2222025A1 (de) | 1972-05-05 | 1972-05-05 | Verfahren zur herstellung von pulverfoermigem n-alkoxymethyl-polylaurinlactam bzw. polyundecansaeureamid mit mindestens 50 % n-alkoxymethylgruppen |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5239637B2 (enrdf_load_html_response) |
| DE (1) | DE2222025A1 (enrdf_load_html_response) |
| FR (1) | FR2183722A1 (enrdf_load_html_response) |
-
1972
- 1972-05-05 DE DE19722222025 patent/DE2222025A1/de active Pending
-
1973
- 1973-04-26 FR FR7315172A patent/FR2183722A1/fr active Granted
- 1973-05-07 JP JP5057673A patent/JPS5239637B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2183722A1 (en) | 1973-12-21 |
| FR2183722B1 (enrdf_load_html_response) | 1977-02-04 |
| JPS4961283A (enrdf_load_html_response) | 1974-06-13 |
| JPS5239637B2 (enrdf_load_html_response) | 1977-10-06 |
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