DE2042814B2 - Verfahren zum stabilisieren einer loesung von acryl- oder methacrylsaeureamid in wasser oder einem organischen loesungsmittel oder einer kristallsuspension oder von kristallen gegen polymerisation - Google Patents
Verfahren zum stabilisieren einer loesung von acryl- oder methacrylsaeureamid in wasser oder einem organischen loesungsmittel oder einer kristallsuspension oder von kristallen gegen polymerisationInfo
- Publication number
- DE2042814B2 DE2042814B2 DE19702042814 DE2042814A DE2042814B2 DE 2042814 B2 DE2042814 B2 DE 2042814B2 DE 19702042814 DE19702042814 DE 19702042814 DE 2042814 A DE2042814 A DE 2042814A DE 2042814 B2 DE2042814 B2 DE 2042814B2
- Authority
- DE
- Germany
- Prior art keywords
- acid amide
- acrylic
- acrylic acid
- polymerization
- solution
- 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.)
- Granted
Links
- 238000006116 polymerization reaction Methods 0.000 title claims description 33
- 239000013078 crystal Substances 0.000 title claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 10
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 8
- 239000003960 organic solvent Substances 0.000 title claims description 6
- 239000000725 suspension Substances 0.000 title claims description 5
- 230000000087 stabilizing effect Effects 0.000 title claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- QELNRWHKYVMINT-UHFFFAOYSA-N 3,5-dimethyl-4-nitrosobenzoic acid Chemical compound CC1=C(C(=CC(=C1)C(=O)O)C)N=O QELNRWHKYVMINT-UHFFFAOYSA-N 0.000 claims description 3
- FEKDDEQYKDNKJG-UHFFFAOYSA-N 1,3,5-trimethyl-2-nitrosobenzene Chemical compound CC1=CC(C)=C(N=O)C(C)=C1 FEKDDEQYKDNKJG-UHFFFAOYSA-N 0.000 claims description 2
- OFQRRUGDGASXKM-UHFFFAOYSA-N 1,3-dimethyl-2-nitrosobenzene Chemical compound CC1=CC=CC(C)=C1N=O OFQRRUGDGASXKM-UHFFFAOYSA-N 0.000 claims description 2
- HFFOTSRZRNHKSR-UHFFFAOYSA-N 5-ethyl-1,3-dimethyl-2-nitrosobenzene Chemical compound CCC1=CC(C)=C(N=O)C(C)=C1 HFFOTSRZRNHKSR-UHFFFAOYSA-N 0.000 claims description 2
- NTQWADDNQQUGRH-UHFFFAOYSA-N hydrogen sulfate;2-methylprop-2-enoylazanium Chemical compound OS(O)(=O)=O.CC(=C)C(N)=O NTQWADDNQQUGRH-UHFFFAOYSA-N 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 230000006641 stabilisation Effects 0.000 claims description 2
- 238000011105 stabilization Methods 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical class NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 31
- 239000003112 inhibitor Substances 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 238000002845 discoloration Methods 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- NLRKCXQQSUWLCH-UHFFFAOYSA-N nitrosobenzene Chemical compound O=NC1=CC=CC=C1 NLRKCXQQSUWLCH-UHFFFAOYSA-N 0.000 description 8
- 239000003381 stabilizer Substances 0.000 description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 238000006386 neutralization reaction Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 4
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 4
- 235000011130 ammonium sulphate Nutrition 0.000 description 4
- GDEBSAWXIHEMNF-UHFFFAOYSA-O cupferron Chemical compound [NH4+].O=NN([O-])C1=CC=CC=C1 GDEBSAWXIHEMNF-UHFFFAOYSA-O 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 3
- 150000002832 nitroso derivatives Chemical class 0.000 description 3
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- ZMWAXVAETNTVAT-UHFFFAOYSA-N 7-n,8-n,5-triphenylphenazin-5-ium-2,3,7,8-tetramine;chloride Chemical compound [Cl-].C=1C=CC=CC=1NC=1C=C2[N+](C=3C=CC=CC=3)=C3C=C(N)C(N)=CC3=NC2=CC=1NC1=CC=CC=C1 ZMWAXVAETNTVAT-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- DMKMTGULLYISBH-UHFFFAOYSA-L disodium;3-hydroxy-4-nitrosonaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=C(N=O)C2=C1 DMKMTGULLYISBH-UHFFFAOYSA-L 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 150000002505 iron Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- SGLDQLCVBBVVAJ-UHFFFAOYSA-N prop-2-enamide;sulfuric acid Chemical class NC(=O)C=C.OS(O)(=O)=O SGLDQLCVBBVVAJ-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- HQYQXJJGHURQSU-UHFFFAOYSA-N 1-butyl-2-nitrosobenzene Chemical compound CCCCC1=CC=CC=C1N=O HQYQXJJGHURQSU-UHFFFAOYSA-N 0.000 description 1
- NSGVPXKWKUZSAY-UHFFFAOYSA-N 1-nitro-2-nitrosobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1N=O NSGVPXKWKUZSAY-UHFFFAOYSA-N 0.000 description 1
- OZMMZGDWELOFTD-UHFFFAOYSA-N 3-methoxy-2-nitrosophenol Chemical compound COC1=CC=CC(O)=C1N=O OZMMZGDWELOFTD-UHFFFAOYSA-N 0.000 description 1
- CYTWMXYLKADNKE-UHFFFAOYSA-N 4-nitrosobenzoic acid Chemical compound OC(=O)C1=CC=C(N=O)C=C1 CYTWMXYLKADNKE-UHFFFAOYSA-N 0.000 description 1
- MPJKRWIIFZGISL-UHFFFAOYSA-N 5-tert-butyl-1,3-dimethyl-2-nitrosobenzene Chemical compound CC1=C(C(=CC(=C1)C(C)(C)C)C)N=O MPJKRWIIFZGISL-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 241001550224 Apha Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 208000034874 Product colour issue Diseases 0.000 description 1
- -1 Sodium nitrile Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- NLRKCXQQSUWLCH-IDEBNGHGSA-N nitrosobenzene Chemical class O=N[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 NLRKCXQQSUWLCH-IDEBNGHGSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 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
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/52—Amides or imides
- C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F20/56—Acrylamide; Methacrylamide
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6895969 | 1969-08-30 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2042814A1 DE2042814A1 (de) | 1971-04-08 |
| DE2042814B2 true DE2042814B2 (de) | 1973-04-12 |
| DE2042814C3 DE2042814C3 (enExample) | 1973-10-31 |
Family
ID=13388704
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702042814 Granted DE2042814B2 (de) | 1969-08-30 | 1970-08-28 | Verfahren zum stabilisieren einer loesung von acryl- oder methacrylsaeureamid in wasser oder einem organischen loesungsmittel oder einer kristallsuspension oder von kristallen gegen polymerisation |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3699081A (enExample) |
| BE (1) | BE755440A (enExample) |
| DE (1) | DE2042814B2 (enExample) |
| FR (1) | FR2059321A5 (enExample) |
| GB (1) | GB1252392A (enExample) |
| NL (1) | NL140844B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE792339A (fr) * | 1971-12-06 | 1973-03-30 | Mitsui Toatsu Chemicals | Procede de concentration d'une solution aqueuse d'acrylamide |
| US3855075A (en) * | 1972-04-03 | 1974-12-17 | American Cyanamid Co | Method of purification of acrylamide by distillation with a polymer inhibitor |
| JPS6012344B2 (ja) * | 1973-06-05 | 1985-04-01 | 三井東圧化学株式会社 | アクリルアミド水溶液の処理方法 |
| US3887425A (en) * | 1973-10-01 | 1975-06-03 | American Cyanamid Co | Concentrating acrylamide solutions |
| US4163755A (en) * | 1973-10-29 | 1979-08-07 | American Cyanamid Company | Processing of acrylamide solutions; concentration without polymer formation |
| GB0124711D0 (en) * | 2001-10-15 | 2001-12-05 | Randox Lab Ltd | Spin trap for use in biological systems |
| US8569538B2 (en) * | 2006-06-30 | 2013-10-29 | Johnson & Johnson Vision Care, Inc. | Acryloyl materials for molded plastics |
| US8053539B2 (en) * | 2006-06-30 | 2011-11-08 | Johnson & Johnson Vision Care Inc. | Siloxanyl materials for molded plastics |
| US7838698B2 (en) * | 2006-09-29 | 2010-11-23 | Johnson & Johnson Vision Care, Inc. | Hydrolysis-resistant silicone compounds |
| US9056880B2 (en) | 2006-09-29 | 2015-06-16 | Johnson & Johnson Vision Care, Inc. | Process for producing hydrolysis-resistant silicone compounds |
| US20080119627A1 (en) * | 2006-11-22 | 2008-05-22 | Masataka Nakamura | Methods for purifying siloxanyl monomers |
| US8080622B2 (en) | 2007-06-29 | 2011-12-20 | Johnson & Johnson Vision Care, Inc. | Soluble silicone prepolymers |
| US7897654B2 (en) * | 2007-12-27 | 2011-03-01 | Johnson & Johnson Vision Care Inc. | Silicone prepolymer solutions |
| JP5711153B2 (ja) * | 2009-02-18 | 2015-04-30 | ダウ グローバル テクノロジーズ エルエルシー | 重合抑制剤組成物及び蒸留可能なモノマーの重合抑制方法 |
-
1970
- 1970-08-25 US US66864A patent/US3699081A/en not_active Expired - Lifetime
- 1970-08-27 FR FR7031323A patent/FR2059321A5/fr not_active Expired
- 1970-08-28 DE DE19702042814 patent/DE2042814B2/de active Granted
- 1970-08-28 NL NL707012774A patent/NL140844B/xx unknown
- 1970-08-28 BE BE755440D patent/BE755440A/xx unknown
- 1970-09-01 GB GB1252392D patent/GB1252392A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2042814A1 (de) | 1971-04-08 |
| DE2042814C3 (enExample) | 1973-10-31 |
| GB1252392A (enExample) | 1971-11-03 |
| BE755440A (fr) | 1971-02-01 |
| US3699081A (en) | 1972-10-17 |
| FR2059321A5 (enExample) | 1971-05-28 |
| NL140844B (nl) | 1974-01-15 |
| NL7012774A (enExample) | 1971-03-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |