CA1069247A - PROCEDE POUR L'AMINATION DES POLYAMIDES .alpha.,.beta.-INSATURES - Google Patents
PROCEDE POUR L'AMINATION DES POLYAMIDES .alpha.,.beta.-INSATURESInfo
- Publication number
- CA1069247A CA1069247A CA249,925A CA249925A CA1069247A CA 1069247 A CA1069247 A CA 1069247A CA 249925 A CA249925 A CA 249925A CA 1069247 A CA1069247 A CA 1069247A
- Authority
- CA
- Canada
- Prior art keywords
- reaction
- unsaturated amide
- moles
- beta
- alpha
- 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
- 238000000034 method Methods 0.000 title claims abstract description 44
- 150000001408 amides Chemical class 0.000 title claims abstract description 26
- 229920000642 polymer Polymers 0.000 title claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 54
- 239000003513 alkali Substances 0.000 claims abstract description 33
- 238000006462 rearrangement reaction Methods 0.000 claims abstract description 19
- 238000007167 Hofmann rearrangement reaction Methods 0.000 claims abstract description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 114
- 239000000243 solution Substances 0.000 claims description 30
- 229920002401 polyacrylamide Polymers 0.000 claims description 29
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical group [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 21
- 239000007864 aqueous solution Substances 0.000 claims description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- -1 alkali metal salt Chemical class 0.000 claims description 6
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 claims description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 2
- GEOVEUCEIQCBKH-UHFFFAOYSA-N hypoiodous acid Chemical compound IO GEOVEUCEIQCBKH-UHFFFAOYSA-N 0.000 claims description 2
- 159000000000 sodium salts Chemical group 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 2
- 238000007112 amidation reaction Methods 0.000 claims 2
- 239000010442 halite Substances 0.000 claims 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 238000005576 amination reaction Methods 0.000 description 35
- 239000000203 mixture Substances 0.000 description 29
- 125000003368 amide group Chemical group 0.000 description 23
- 229910019093 NaOCl Inorganic materials 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 125000003277 amino group Chemical group 0.000 description 10
- 239000004202 carbamide Substances 0.000 description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000007086 side reaction Methods 0.000 description 5
- 230000008707 rearrangement Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 241000583281 Sugiura Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- HNPDNOZNULJJDL-UHFFFAOYSA-N ethyl n-ethenylcarbamate Chemical compound CCOC(=O)NC=C HNPDNOZNULJJDL-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000004445 quantitative analysis Methods 0.000 description 2
- 239000003507 refrigerant Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 239000000701 coagulant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- GQOKIYDTHHZSCJ-UHFFFAOYSA-M dimethyl-bis(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C=CC[N+](C)(C)CC=C GQOKIYDTHHZSCJ-UHFFFAOYSA-M 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000009790 rate-determining step (RDS) Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by 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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Treatment Of Sludge (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50044408A JPS51122188A (en) | 1975-04-12 | 1975-04-12 | Method of aminating polyacrylamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1069247A true CA1069247A (fr) | 1980-01-01 |
Family
ID=12690676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA249,925A Expired CA1069247A (fr) | 1975-04-12 | 1976-04-09 | PROCEDE POUR L'AMINATION DES POLYAMIDES .alpha.,.beta.-INSATURES |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS51122188A (fr) |
| CA (1) | CA1069247A (fr) |
| DE (1) | DE2615831C2 (fr) |
| FR (1) | FR2306999A1 (fr) |
| GB (1) | GB1518561A (fr) |
| NL (1) | NL158185B (fr) |
| SE (1) | SE414182B (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2841713C2 (de) | 1978-09-25 | 1986-10-16 | Akzo Gmbh, 5600 Wuppertal | Verfahren zur Herstellung von polyfunktionellen Isocyanaten aus polymeren N-Halogenamiden |
| FR2485545A1 (fr) * | 1980-06-25 | 1981-12-31 | Charbonnages Ste Chimique | Cotelomeres a terminaison sulfonate contenant des motifs acide acrylique et vinylamine, procede pour leur preparation et leur application dans des compositions detergentes |
| US5239014A (en) * | 1988-12-28 | 1993-08-24 | Mitsui Toatsu Chemicals, Inc. | Cationic acrylamide polymers and the applications of these polymers |
| US5292821A (en) * | 1988-12-28 | 1994-03-08 | Mitsui Toatsu Chemicals, Inc. | Catonic acrylamide polymers and the applications of these polymers |
| US6013725A (en) * | 1996-10-31 | 2000-01-11 | Eastman Chemical Company | Low temperature crosslinkable latexes formed by in-situ generation of a crosslinkable functionality |
| FR2880901B1 (fr) * | 2005-01-17 | 2008-06-20 | Snf Sas Soc Par Actions Simpli | Procede de fabrication de papier et carton de grande resistance a sec et papiers et cartons ainsi obtenus |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2729560A (en) * | 1953-06-22 | 1956-01-03 | American Cyanamid Co | Wet strength paper containing aminoaliphatic chain polymer resins |
-
1975
- 1975-04-12 JP JP50044408A patent/JPS51122188A/ja active Granted
-
1976
- 1976-04-06 GB GB1379176A patent/GB1518561A/en not_active Expired
- 1976-04-09 SE SE7604217A patent/SE414182B/xx not_active IP Right Cessation
- 1976-04-09 CA CA249,925A patent/CA1069247A/fr not_active Expired
- 1976-04-10 DE DE19762615831 patent/DE2615831C2/de not_active Expired
- 1976-04-12 NL NL7603872A patent/NL158185B/xx not_active IP Right Cessation
- 1976-04-12 FR FR7610627A patent/FR2306999A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| NL158185B (nl) | 1978-10-16 |
| JPS5223661B2 (fr) | 1977-06-25 |
| AU1274676A (en) | 1977-10-13 |
| FR2306999B1 (fr) | 1979-05-11 |
| JPS51122188A (en) | 1976-10-26 |
| GB1518561A (en) | 1978-07-19 |
| FR2306999A1 (fr) | 1976-11-05 |
| DE2615831A1 (de) | 1976-10-14 |
| SE414182B (sv) | 1980-07-14 |
| SE7604217L (sv) | 1976-10-13 |
| DE2615831C2 (de) | 1982-07-29 |
| NL7603872A (nl) | 1976-10-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |