DE1136109B - Verfahren zum Stabilisieren von Polyoxymethylenen - Google Patents
Verfahren zum Stabilisieren von PolyoxymethylenenInfo
- Publication number
- DE1136109B DE1136109B DEF30681A DEF0030681A DE1136109B DE 1136109 B DE1136109 B DE 1136109B DE F30681 A DEF30681 A DE F30681A DE F0030681 A DEF0030681 A DE F0030681A DE 1136109 B DE1136109 B DE 1136109B
- Authority
- DE
- Germany
- Prior art keywords
- polymer
- weight
- ether
- polyoxymethylenes
- parts
- 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 19
- 229920006324 polyoxymethylene Polymers 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 10
- 230000000087 stabilizing effect Effects 0.000 title claims 2
- 229920000642 polymer Polymers 0.000 claims description 42
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 150000002170 ethers Chemical class 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims description 7
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 239000004611 light stabiliser Substances 0.000 claims description 3
- 230000006641 stabilisation Effects 0.000 description 13
- 238000011105 stabilization Methods 0.000 description 13
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Natural products CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 229910015900 BF3 Inorganic materials 0.000 description 6
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 6
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- NHOGGUYTANYCGQ-UHFFFAOYSA-N ethenoxybenzene Chemical compound C=COC1=CC=CC=C1 NHOGGUYTANYCGQ-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 229930188620 butyrolactone Natural products 0.000 description 2
- 239000011951 cationic catalyst Substances 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- RCRRYCRTBURQSZ-UHFFFAOYSA-N 1-ethenoxy-4-methoxybutane Chemical compound COCCCCOC=C RCRRYCRTBURQSZ-UHFFFAOYSA-N 0.000 description 1
- QJJDJWUCRAPCOL-UHFFFAOYSA-N 1-ethenoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOC=C QJJDJWUCRAPCOL-UHFFFAOYSA-N 0.000 description 1
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 1
- UHBAWOXYQROEIH-UHFFFAOYSA-N 3-chloro-4-(2-chlorobut-3-enoxy)but-1-ene Chemical compound C=CC(Cl)COCC(Cl)C=C UHBAWOXYQROEIH-UHFFFAOYSA-N 0.000 description 1
- 101100004287 Caenorhabditis elegans best-6 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000003609 aryl vinyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 238000009739 binding Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- C08G2/30—Chemical modification by after-treatment
- C08G2/34—Chemical modification by after-treatment by etherification
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL261955D NL261955A (en, 2012) | 1960-03-04 | ||
| NL126409D NL126409C (en, 2012) | 1960-03-04 | ||
| DEF30681A DE1136109B (de) | 1960-03-04 | 1960-03-04 | Verfahren zum Stabilisieren von Polyoxymethylenen |
| DEF32822A DE1143025B (de) | 1960-03-04 | 1960-12-22 | Verfahren zum Stabilisieren von Polyoxymethylenen |
| DEF32823A DE1143329B (de) | 1960-03-04 | 1960-12-22 | Verfahren zum Stabilisieren von Polyoxymethylenen |
| US93041A US3244672A (en) | 1960-03-04 | 1961-03-03 | Alpha, beta-unsaturated ether stabilized polyoxymethylenes and a process for preparing the same |
| FR854594A FR1286118A (fr) | 1960-03-04 | 1961-03-04 | Procédé de stabilisation de polyoxyméthylènes |
| GB8172/61A GB976702A (en) | 1960-03-04 | 1961-03-06 | Stabilized polyoxymethylenes and a process for preparing same |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF30681A DE1136109B (de) | 1960-03-04 | 1960-03-04 | Verfahren zum Stabilisieren von Polyoxymethylenen |
| DEF32822A DE1143025B (de) | 1960-03-04 | 1960-12-22 | Verfahren zum Stabilisieren von Polyoxymethylenen |
| DEF32823A DE1143329B (de) | 1960-03-04 | 1960-12-22 | Verfahren zum Stabilisieren von Polyoxymethylenen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1136109B true DE1136109B (de) | 1962-09-06 |
Family
ID=27210165
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF30681A Pending DE1136109B (de) | 1960-03-04 | 1960-03-04 | Verfahren zum Stabilisieren von Polyoxymethylenen |
| DEF32822A Pending DE1143025B (de) | 1960-03-04 | 1960-12-22 | Verfahren zum Stabilisieren von Polyoxymethylenen |
| DEF32823A Pending DE1143329B (de) | 1960-03-04 | 1960-12-22 | Verfahren zum Stabilisieren von Polyoxymethylenen |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF32822A Pending DE1143025B (de) | 1960-03-04 | 1960-12-22 | Verfahren zum Stabilisieren von Polyoxymethylenen |
| DEF32823A Pending DE1143329B (de) | 1960-03-04 | 1960-12-22 | Verfahren zum Stabilisieren von Polyoxymethylenen |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3244672A (en, 2012) |
| DE (3) | DE1136109B (en, 2012) |
| GB (1) | GB976702A (en, 2012) |
| NL (2) | NL126409C (en, 2012) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1180129B (de) | 1961-07-21 | 1964-10-22 | Kurashiki Rayon Co | Verfahren zum Stabilisieren von Poly-oxymethylenen |
| DE1180520B (de) * | 1960-12-02 | 1964-10-29 | Degussa | Verfahren zum Stabilisieren von Polyoxymethylenen |
| DE2501678A1 (de) * | 1974-01-31 | 1975-08-14 | Air Prod & Chem | Pfropf-copolymerisate aus stickstoffhaltigen cyclischen- und estermonomeren mit geschuetzten endgruppen |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4094867A (en) * | 1962-11-06 | 1978-06-13 | Imperial Chemical Industries Limited | Manufacture of polysulphones |
| US3424722A (en) * | 1968-01-02 | 1969-01-28 | Gen Electric | Phenyl-capped polyphenylene ethers |
| IT1027886B (it) * | 1974-12-20 | 1978-12-20 | Sir Soc Italiana Resine Spa | Procedimento per la preparazione di polimeri acetalici eterificati |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2732370A (en) * | 1956-01-24 | Polymers | ||
| US2296249A (en) * | 1940-08-26 | 1942-09-22 | Du Pont | Polymers of formaldehyde |
| US2962476A (en) * | 1956-11-30 | 1960-11-29 | Gen Aniline & Film Corp | Polymerized alkyl vinyl ethers of improved stability |
| US2989508A (en) * | 1957-10-21 | 1961-06-20 | Celanese Corp | Solution polymerization |
| DE1091750B (de) * | 1958-06-14 | 1960-10-27 | Basf Ag | Verfahren zum Modifizieren der Endgruppen hochpolymerer Formaldehyde |
| US3087913A (en) * | 1959-03-11 | 1963-04-30 | Celanese Corp | Copolymers of trioxane and vinyl ethers |
| US3002952A (en) * | 1959-09-22 | 1961-10-03 | Du Pont | Initiators for the polymerization of formaldehyde |
-
0
- NL NL261955D patent/NL261955A/xx unknown
- NL NL126409D patent/NL126409C/xx active
-
1960
- 1960-03-04 DE DEF30681A patent/DE1136109B/de active Pending
- 1960-12-22 DE DEF32822A patent/DE1143025B/de active Pending
- 1960-12-22 DE DEF32823A patent/DE1143329B/de active Pending
-
1961
- 1961-03-03 US US93041A patent/US3244672A/en not_active Expired - Lifetime
- 1961-03-06 GB GB8172/61A patent/GB976702A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1180520B (de) * | 1960-12-02 | 1964-10-29 | Degussa | Verfahren zum Stabilisieren von Polyoxymethylenen |
| DE1180129B (de) | 1961-07-21 | 1964-10-22 | Kurashiki Rayon Co | Verfahren zum Stabilisieren von Poly-oxymethylenen |
| DE2501678A1 (de) * | 1974-01-31 | 1975-08-14 | Air Prod & Chem | Pfropf-copolymerisate aus stickstoffhaltigen cyclischen- und estermonomeren mit geschuetzten endgruppen |
Also Published As
| Publication number | Publication date |
|---|---|
| NL126409C (en, 2012) | |
| GB976702A (en) | 1964-12-02 |
| DE1143329B (de) | 1963-02-07 |
| US3244672A (en) | 1966-04-05 |
| NL261955A (en, 2012) | |
| DE1143025B (de) | 1963-01-31 |
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