DE1162081B - Verfahren zur Herstellung von hochmolekularen Polyoxymethylenen - Google Patents
Verfahren zur Herstellung von hochmolekularen PolyoxymethylenenInfo
- Publication number
- DE1162081B DE1162081B DEST18784A DEST018784A DE1162081B DE 1162081 B DE1162081 B DE 1162081B DE ST18784 A DEST18784 A DE ST18784A DE ST018784 A DEST018784 A DE ST018784A DE 1162081 B DE1162081 B DE 1162081B
- Authority
- DE
- Germany
- Prior art keywords
- catalysts
- molecular weight
- high molecular
- polymerization
- 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
- -1 polyoxymethylenes Polymers 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 229920006324 polyoxymethylene Polymers 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 35
- 239000003054 catalyst Substances 0.000 claims description 16
- 238000006116 polymerization reaction Methods 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- FDIOSTIIZGWENY-UHFFFAOYSA-N n-[bis(diethylamino)phosphanyl]-n-ethylethanamine Chemical compound CCN(CC)P(N(CC)CC)N(CC)CC FDIOSTIIZGWENY-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical group [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000003003 phosphines Chemical group 0.000 description 2
- 150000004714 phosphonium salts Chemical class 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical group [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 description 2
- GEQBPMNDDHGGPJ-UHFFFAOYSA-N tri(piperidin-1-yl)phosphane Chemical compound C1CCCCN1P(N1CCCCC1)N1CCCCC1 GEQBPMNDDHGGPJ-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical group S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- KLAXYJXVAGRMEU-UHFFFAOYSA-N N-bis(N-methylanilino)phosphanyl-N-methylaniline Chemical compound CN(C1=CC=CC=C1)P(N(C)C1=CC=CC=C1)N(C)C1=CC=CC=C1 KLAXYJXVAGRMEU-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910001361 White metal Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- XVDBWWRIXBMVJV-UHFFFAOYSA-N n-[bis(dimethylamino)phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(N(C)C)N(C)C XVDBWWRIXBMVJV-UHFFFAOYSA-N 0.000 description 1
- UPPMICTXNFKBNF-UHFFFAOYSA-N n-[diethylamino(ethyl)phosphanyl]-n-ethylethanamine Chemical compound CCN(CC)P(CC)N(CC)CC UPPMICTXNFKBNF-UHFFFAOYSA-N 0.000 description 1
- IOLWHTAVAUCOPP-UHFFFAOYSA-N n-diethylphosphanyl-n-ethylethanamine Chemical compound CCN(CC)P(CC)CC IOLWHTAVAUCOPP-UHFFFAOYSA-N 0.000 description 1
- AEOFYYUGLYQJHY-UHFFFAOYSA-N n-diphenylphosphanyl-n-ethylethanamine Chemical compound C=1C=CC=CC=1P(N(CC)CC)C1=CC=CC=C1 AEOFYYUGLYQJHY-UHFFFAOYSA-N 0.000 description 1
- HMCXUWOCJBEBES-UHFFFAOYSA-N n-ethyl-n-phosphanylethanamine Chemical compound CCN(P)CC HMCXUWOCJBEBES-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000010969 white metal Substances 0.000 description 1
- 239000008096 xylene Substances 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
- C08G2/08—Polymerisation of formaldehyde
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)
- Phenolic Resins Or Amino Resins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL260727 | 1961-02-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1162081B true DE1162081B (de) | 1964-01-30 |
Family
ID=19752850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEST18784A Pending DE1162081B (de) | 1961-02-01 | 1962-01-25 | Verfahren zur Herstellung von hochmolekularen Polyoxymethylenen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3227689A (en, 2012) |
| BE (1) | BE613285A (en, 2012) |
| CH (1) | CH415055A (en, 2012) |
| DE (1) | DE1162081B (en, 2012) |
| GB (1) | GB989429A (en, 2012) |
| NL (2) | NL260727A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1192823B (de) | 1961-05-12 | 1965-05-13 | Dynamit Nobel Ag | Verfahren zur Herstellung von hochmolekularen Polyoxymethylenen |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL302396A (en, 2012) * | 1963-01-29 | |||
| US3395124A (en) * | 1964-11-23 | 1968-07-30 | British Industrial Plastics | Polymerization of trioxan using a carbonium hexafluoroarsenate as a catalyst |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB793673A (en) * | 1955-07-13 | 1958-04-23 | Du Pont | Improvements in or relating to the preparation of high molecular weight addition polymers of formaldehyde |
| DE1037127B (de) * | 1952-08-30 | 1958-08-21 | Du Pont | Katalysatoren zur Polymerisation von Formaldehyd |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1940383A (en) * | 1932-04-14 | 1933-12-19 | Victor Chemical Works | Phosphorus amide-aldehyde resin and method of preparing the same |
| GB478326A (en) * | 1936-07-17 | 1938-01-17 | Henry Dreyfus | Improvements in the manufacture of ketene, acetic anhydride or a homologue thereof |
| US2828286A (en) * | 1952-08-30 | 1958-03-25 | Du Pont | Polymerization of formaldehyde |
| NL196512A (en, 2012) * | 1954-04-16 | |||
| US3017389A (en) * | 1955-03-18 | 1962-01-16 | Du Pont | Process of controlling the molecular weight of linear formaldehyde polymers |
| FR1171437A (fr) * | 1958-01-27 | 1959-01-26 | Eastman Kodak Co | Procédé de fabrication de polyoléfines, produits obtenus et catalyseurs pour la mise en oeuvre de ce procédé |
-
0
- NL NL109463D patent/NL109463C/xx active
- NL NL260727D patent/NL260727A/xx unknown
- BE BE613285D patent/BE613285A/xx unknown
-
1962
- 1962-01-25 DE DEST18784A patent/DE1162081B/de active Pending
- 1962-01-29 US US169595A patent/US3227689A/en not_active Expired - Lifetime
- 1962-01-29 CH CH103762A patent/CH415055A/de unknown
- 1962-02-01 GB GB3976/62A patent/GB989429A/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1037127B (de) * | 1952-08-30 | 1958-08-21 | Du Pont | Katalysatoren zur Polymerisation von Formaldehyd |
| GB793673A (en) * | 1955-07-13 | 1958-04-23 | Du Pont | Improvements in or relating to the preparation of high molecular weight addition polymers of formaldehyde |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1192823B (de) | 1961-05-12 | 1965-05-13 | Dynamit Nobel Ag | Verfahren zur Herstellung von hochmolekularen Polyoxymethylenen |
Also Published As
| Publication number | Publication date |
|---|---|
| CH415055A (de) | 1966-06-15 |
| GB989429A (en) | 1965-04-14 |
| NL109463C (en, 2012) | |
| BE613285A (en, 2012) | |
| NL260727A (en, 2012) | |
| US3227689A (en) | 1966-01-04 |
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