DE1105161B - Verfahren zum Stabilisieren von makromolekularem Polyformaldehyd - Google Patents
Verfahren zum Stabilisieren von makromolekularem PolyformaldehydInfo
- Publication number
- DE1105161B DE1105161B DEB55831A DEB0055831A DE1105161B DE 1105161 B DE1105161 B DE 1105161B DE B55831 A DEB55831 A DE B55831A DE B0055831 A DEB0055831 A DE B0055831A DE 1105161 B DE1105161 B DE 1105161B
- Authority
- DE
- Germany
- Prior art keywords
- polyformaldehyde
- macromolecular
- methyl
- phenyl
- stabilized
- 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
- 229920006324 polyoxymethylene Polymers 0.000 title claims description 27
- 238000000034 method Methods 0.000 title claims description 4
- 230000000087 stabilizing effect Effects 0.000 title claims 2
- 239000004952 Polyamide Substances 0.000 claims description 8
- 229920002647 polyamide Polymers 0.000 claims description 8
- -1 nitrogen-containing compounds Hydrazones Chemical class 0.000 claims description 5
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- 230000015556 catabolic process Effects 0.000 claims description 4
- 238000006731 degradation reaction Methods 0.000 claims description 4
- 238000002845 discoloration Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- OLBVUFHMDRJKTK-UHFFFAOYSA-N [N].[O] Chemical compound [N].[O] OLBVUFHMDRJKTK-UHFFFAOYSA-N 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 6
- 150000007857 hydrazones Chemical class 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 2
- SVEMZZKLXDIJGA-UHFFFAOYSA-N 6-tert-butyl-2-[(3-tert-butyl-6-ethyl-2-hydroxyphenyl)methyl]-3-ethylphenol Chemical compound CCC1=CC=C(C(C)(C)C)C(O)=C1CC1=C(CC)C=CC(C(C)(C)C)=C1O SVEMZZKLXDIJGA-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- JGOAZQAXRONCCI-UHFFFAOYSA-N n-(benzylideneamino)aniline Chemical compound C=1C=CC=CC=1NN=CC1=CC=CC=C1 JGOAZQAXRONCCI-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229940081310 piperonal Drugs 0.000 description 1
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Natural products O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
- C08K5/30—Hydrazones; Semicarbazones
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyamides (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE597962D BE597962A (enrdf_load_stackoverflow) | 1959-12-09 | ||
| NL258830D NL258830A (enrdf_load_stackoverflow) | 1959-12-09 | ||
| NL127898D NL127898C (enrdf_load_stackoverflow) | 1959-12-09 | ||
| DEB55831A DE1105161B (de) | 1959-12-09 | 1959-12-09 | Verfahren zum Stabilisieren von makromolekularem Polyformaldehyd |
| GB4189660A GB895115A (en) | 1959-12-09 | 1960-12-06 | Stabilised macromolecular polyformaldehyde and process |
| FR846435A FR1281481A (fr) | 1959-12-09 | 1960-12-09 | Procédé pour la stabilisation de polyformaldéhyde macromoléculaire |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB55831A DE1105161B (de) | 1959-12-09 | 1959-12-09 | Verfahren zum Stabilisieren von makromolekularem Polyformaldehyd |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1105161B true DE1105161B (de) | 1961-04-20 |
Family
ID=6971118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB55831A Pending DE1105161B (de) | 1959-12-09 | 1959-12-09 | Verfahren zum Stabilisieren von makromolekularem Polyformaldehyd |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE597962A (enrdf_load_stackoverflow) |
| DE (1) | DE1105161B (enrdf_load_stackoverflow) |
| GB (1) | GB895115A (enrdf_load_stackoverflow) |
| NL (2) | NL258830A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1143637B (de) * | 1961-03-11 | 1963-02-14 | Hoechst Ag | Schiffsche Basen zum Stabilisieren von Polyacetalen |
| DE1161016B (de) * | 1961-03-14 | 1964-01-09 | Degussa | Verwendung von Stickstoff und Schwefel enthaltenden Verbindungen als Stabilisierungsmittel fuer Polyoxymethylenmassen |
| DE1183677B (de) * | 1961-11-11 | 1964-12-17 | Hoechst Ag | Stabilisieren von Polyacetalen |
| DE1190183B (de) * | 1961-06-28 | 1965-04-01 | Kurashiki Rayon Co | Stabilisatorgemisch fuer hochmolekulare Polyoxymethylene |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1063573A (en) * | 1964-01-23 | 1967-03-30 | Asahi Chemical Ind | Method for the production of trioxane copolymer containing nitrogen |
-
0
- NL NL127898D patent/NL127898C/xx active
- BE BE597962D patent/BE597962A/xx unknown
- NL NL258830D patent/NL258830A/xx unknown
-
1959
- 1959-12-09 DE DEB55831A patent/DE1105161B/de active Pending
-
1960
- 1960-12-06 GB GB4189660A patent/GB895115A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1143637B (de) * | 1961-03-11 | 1963-02-14 | Hoechst Ag | Schiffsche Basen zum Stabilisieren von Polyacetalen |
| DE1161016B (de) * | 1961-03-14 | 1964-01-09 | Degussa | Verwendung von Stickstoff und Schwefel enthaltenden Verbindungen als Stabilisierungsmittel fuer Polyoxymethylenmassen |
| DE1190183B (de) * | 1961-06-28 | 1965-04-01 | Kurashiki Rayon Co | Stabilisatorgemisch fuer hochmolekulare Polyoxymethylene |
| DE1183677B (de) * | 1961-11-11 | 1964-12-17 | Hoechst Ag | Stabilisieren von Polyacetalen |
Also Published As
| Publication number | Publication date |
|---|---|
| GB895115A (en) | 1962-05-02 |
| NL127898C (enrdf_load_stackoverflow) | |
| NL258830A (enrdf_load_stackoverflow) | |
| BE597962A (enrdf_load_stackoverflow) |
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