DE1201995B - Verfahren zum Veraethern von hochmolekularen Polyoxymethylenen - Google Patents
Verfahren zum Veraethern von hochmolekularen PolyoxymethylenenInfo
- Publication number
- DE1201995B DE1201995B DEF27116A DEF0027116A DE1201995B DE 1201995 B DE1201995 B DE 1201995B DE F27116 A DEF27116 A DE F27116A DE F0027116 A DEF0027116 A DE F0027116A DE 1201995 B DE1201995 B DE 1201995B
- Authority
- DE
- Germany
- Prior art keywords
- molecular weight
- high molecular
- polyoxymethylenes
- etherifying
- polyoxymethylene
- 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 21
- 229920006324 polyoxymethylene Polymers 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 4
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000006266 etherification reaction Methods 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 230000004580 weight loss Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- CHNLPLHJUPMEOI-UHFFFAOYSA-N oxolane;trifluoroborane Chemical compound FB(F)F.C1CCOC1 CHNLPLHJUPMEOI-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- BDUPRNVPXOHWIL-UHFFFAOYSA-N dimethyl sulfite Chemical compound COS(=O)OC BDUPRNVPXOHWIL-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003336 secondary aromatic amines Chemical class 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 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
- C08G2/30—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)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE583593D BE583593A (enrdf_load_stackoverflow) | 1958-11-25 | ||
NL111847D NL111847C (enrdf_load_stackoverflow) | 1958-11-25 | ||
NL245719D NL245719A (enrdf_load_stackoverflow) | 1958-11-25 | ||
DEF27116A DE1201995B (de) | 1958-11-25 | 1958-11-25 | Verfahren zum Veraethern von hochmolekularen Polyoxymethylenen |
CH7931859A CH431988A (de) | 1958-11-25 | 1959-10-12 | Verfahren zur Herstellung von thermoplastisch verarbeitbaren, hochmolekularen Polyoxymethylenäthern |
FR807530A FR1238071A (fr) | 1958-11-25 | 1959-10-15 | Procédé de préparation de polyoxyméthylènes à poids moléculaire élevé, faconnables à l'état thermoplastique |
GB3991859A GB869323A (en) | 1958-11-25 | 1959-11-24 | Process for the production of high molecular weight, thermoplastically workable polyoxymethylene derivatives |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF27116A DE1201995B (de) | 1958-11-25 | 1958-11-25 | Verfahren zum Veraethern von hochmolekularen Polyoxymethylenen |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1201995B true DE1201995B (de) | 1965-09-30 |
Family
ID=7092298
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEF27116A Pending DE1201995B (de) | 1958-11-25 | 1958-11-25 | Verfahren zum Veraethern von hochmolekularen Polyoxymethylenen |
Country Status (6)
Country | Link |
---|---|
BE (1) | BE583593A (enrdf_load_stackoverflow) |
CH (1) | CH431988A (enrdf_load_stackoverflow) |
DE (1) | DE1201995B (enrdf_load_stackoverflow) |
FR (1) | FR1238071A (enrdf_load_stackoverflow) |
GB (1) | GB869323A (enrdf_load_stackoverflow) |
NL (2) | NL245719A (enrdf_load_stackoverflow) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1230220B (de) | 1959-01-06 | 1966-12-08 | Du Pont | Verfahren zur Herstellung von hochmolekularen Polyoxymethylenaethern |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1006136B (it) * | 1973-12-28 | 1976-09-30 | Sir Soc Italiana Resine Spa | Stabilizzazione di polimeri acetalici |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1091750B (de) | 1958-06-14 | 1960-10-27 | Basf Ag | Verfahren zum Modifizieren der Endgruppen hochpolymerer Formaldehyde |
-
0
- BE BE583593D patent/BE583593A/xx unknown
- NL NL111847D patent/NL111847C/xx active
- NL NL245719D patent/NL245719A/xx unknown
-
1958
- 1958-11-25 DE DEF27116A patent/DE1201995B/de active Pending
-
1959
- 1959-10-12 CH CH7931859A patent/CH431988A/de unknown
- 1959-10-15 FR FR807530A patent/FR1238071A/fr not_active Expired
- 1959-11-24 GB GB3991859A patent/GB869323A/en not_active Expired
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1091750B (de) | 1958-06-14 | 1960-10-27 | Basf Ag | Verfahren zum Modifizieren der Endgruppen hochpolymerer Formaldehyde |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1230220B (de) | 1959-01-06 | 1966-12-08 | Du Pont | Verfahren zur Herstellung von hochmolekularen Polyoxymethylenaethern |
Also Published As
Publication number | Publication date |
---|---|
FR1238071A (fr) | 1960-08-05 |
NL245719A (enrdf_load_stackoverflow) | |
CH431988A (de) | 1967-03-15 |
BE583593A (enrdf_load_stackoverflow) | |
GB869323A (en) | 1961-05-31 |
NL111847C (enrdf_load_stackoverflow) |
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