DE1145793B - Verfahren zur Herstellung von Copolymerisaten des Trioxans - Google Patents
Verfahren zur Herstellung von Copolymerisaten des TrioxansInfo
- Publication number
- DE1145793B DE1145793B DEF32536A DEF0032536A DE1145793B DE 1145793 B DE1145793 B DE 1145793B DE F32536 A DEF32536 A DE F32536A DE F0032536 A DEF0032536 A DE F0032536A DE 1145793 B DE1145793 B DE 1145793B
- Authority
- DE
- Germany
- Prior art keywords
- weight
- parts
- acrylonitrile
- trioxane
- polymerization
- 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
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 title claims description 27
- 229920001577 copolymer Polymers 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title description 3
- 229920000642 polymer Polymers 0.000 claims description 22
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 21
- 238000006116 polymerization reaction Methods 0.000 claims description 21
- 239000003054 catalyst Substances 0.000 claims description 11
- -1 tetrafluoroborate Chemical compound 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 8
- 230000004580 weight loss Effects 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 6
- 229910015900 BF3 Inorganic materials 0.000 claims description 3
- 239000011951 cationic catalyst Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 15
- 239000000047 product Substances 0.000 claims 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 3
- 239000000243 solution Substances 0.000 claims 3
- 238000010626 work up procedure Methods 0.000 claims 3
- ICMFHHGKLRTCBM-UHFFFAOYSA-N 4-nitrobenzenediazonium Chemical compound [O-][N+](=O)C1=CC=C([N+]#N)C=C1 ICMFHHGKLRTCBM-UHFFFAOYSA-N 0.000 claims 2
- 229930188620 butyrolactone Natural products 0.000 claims 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims 2
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 claims 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 claims 1
- 150000008360 acrylonitriles Chemical class 0.000 claims 1
- 235000019445 benzyl alcohol Nutrition 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 239000012265 solid product Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 229920001519 homopolymer Polymers 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 239000002841 Lewis acid Substances 0.000 description 5
- 150000007517 lewis acids Chemical class 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 125000001976 hemiacetal group Chemical group 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920006324 polyoxymethylene Polymers 0.000 description 3
- 238000007669 thermal treatment Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- UDFDQZHQZUACRP-UHFFFAOYSA-N tripropyloxidanium Chemical compound CCC[O+](CCC)CCC UDFDQZHQZUACRP-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- DWCSXQCXXITVKE-UHFFFAOYSA-N triethyloxidanium Chemical compound CC[O+](CC)CC DWCSXQCXXITVKE-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
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/06—Catalysts
-
- 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
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
-
- 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
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/18—Copolymerisation of aldehydes or ketones
- C08G2/26—Copolymerisation of aldehydes or ketones with compounds containing carbon-to-carbon unsaturation
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Catalysts (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE610223D BE610223A (en, 2012) | 1960-11-12 | ||
| NL271115D NL271115A (en, 2012) | 1960-11-12 | ||
| DEF32536A DE1145793B (de) | 1960-11-12 | 1960-11-12 | Verfahren zur Herstellung von Copolymerisaten des Trioxans |
| US151374A US3364180A (en) | 1960-11-12 | 1961-11-09 | Process for preparing copolymers of cyclic acetals and acrylonitrile |
| CH1305061A CH413369A (de) | 1960-11-12 | 1961-11-10 | Verfahren zur Mischpolymerisation cyclischer Acetale mit Acrylnitril |
| GB40603/61A GB1001341A (en) | 1960-11-12 | 1961-11-13 | Copolymers of trioxane and process for their manufacture |
| FR878674A FR1306809A (fr) | 1960-11-12 | 1961-11-13 | Procédé de copolymérisation d'acétals cycliques avec l'acrylonitrile |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF32536A DE1145793B (de) | 1960-11-12 | 1960-11-12 | Verfahren zur Herstellung von Copolymerisaten des Trioxans |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1145793B true DE1145793B (de) | 1963-03-21 |
Family
ID=7094675
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF32536A Pending DE1145793B (de) | 1960-11-12 | 1960-11-12 | Verfahren zur Herstellung von Copolymerisaten des Trioxans |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3364180A (en, 2012) |
| BE (1) | BE610223A (en, 2012) |
| CH (1) | CH413369A (en, 2012) |
| DE (1) | DE1145793B (en, 2012) |
| GB (1) | GB1001341A (en, 2012) |
| NL (1) | NL271115A (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5162278A (en) * | 1988-07-15 | 1992-11-10 | Fina Technology, Inc. | Non-bridged syndiospecific metallocene catalysts and polymerization process |
| US5155080A (en) * | 1988-07-15 | 1992-10-13 | Fina Technology, Inc. | Process and catalyst for producing syndiotactic polyolefins |
| US6503863B2 (en) | 1999-06-07 | 2003-01-07 | Exxonmobil Chemical Patents, Inc. | Heat treating a molecular sieve and catalyst |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1226988A (fr) * | 1958-06-20 | 1960-08-18 | Celanese Corp | Fabrication de polyoxyméthylène par polymérisation de trioxane |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2946760A (en) * | 1956-05-23 | 1960-07-26 | Chemstrand Corp | Stabilized acrylonitrile polymer composition and method of making same |
| US3069402A (en) * | 1957-10-17 | 1962-12-18 | Celanese Corp | Polyacrylonitrile and method of preparation |
| NL130561C (en, 2012) * | 1958-12-23 | |||
| US3087913A (en) * | 1959-03-11 | 1963-04-30 | Celanese Corp | Copolymers of trioxane and vinyl ethers |
| NL285319A (en, 2012) * | 1960-06-13 |
-
0
- BE BE610223D patent/BE610223A/xx unknown
- NL NL271115D patent/NL271115A/xx unknown
-
1960
- 1960-11-12 DE DEF32536A patent/DE1145793B/de active Pending
-
1961
- 1961-11-09 US US151374A patent/US3364180A/en not_active Expired - Lifetime
- 1961-11-10 CH CH1305061A patent/CH413369A/de unknown
- 1961-11-13 GB GB40603/61A patent/GB1001341A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1226988A (fr) * | 1958-06-20 | 1960-08-18 | Celanese Corp | Fabrication de polyoxyméthylène par polymérisation de trioxane |
Also Published As
| Publication number | Publication date |
|---|---|
| US3364180A (en) | 1968-01-16 |
| NL271115A (en, 2012) | |
| BE610223A (en, 2012) | |
| GB1001341A (en) | 1965-08-18 |
| CH413369A (de) | 1966-05-15 |
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