DE1174064B - Stabilisieren von polymeren Acetalen - Google Patents
Stabilisieren von polymeren AcetalenInfo
- Publication number
- DE1174064B DE1174064B DEF37167A DEF0037167A DE1174064B DE 1174064 B DE1174064 B DE 1174064B DE F37167 A DEF37167 A DE F37167A DE F0037167 A DEF0037167 A DE F0037167A DE 1174064 B DE1174064 B DE 1174064B
- Authority
- DE
- Germany
- Prior art keywords
- weight
- phenoxypropionitrile
- parts
- tert
- butyl
- 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
- 150000001241 acetals Chemical class 0.000 title claims description 22
- 230000006641 stabilisation Effects 0.000 title description 3
- 238000011105 stabilization Methods 0.000 title description 3
- 239000003381 stabilizer Substances 0.000 claims description 15
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 230000015556 catabolic process Effects 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 238000006731 degradation reaction Methods 0.000 claims description 5
- 150000002170 ethers Chemical class 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 4
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
- 229920001577 copolymer Polymers 0.000 description 20
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 9
- XBFTTWVZVHRAQW-UHFFFAOYSA-N 2-(2-tert-butyl-4-methylphenoxy)propanenitrile Chemical compound N#CC(C)OC1=CC=C(C)C=C1C(C)(C)C XBFTTWVZVHRAQW-UHFFFAOYSA-N 0.000 description 5
- DQNNXXFOHGSGFX-UHFFFAOYSA-N 2-[4-methyl-2,6-bis(2-phenylethyl)phenoxy]propanenitrile Chemical compound CC1=CC(=C(OC(C#N)C)C(=C1)CCC1=CC=CC=C1)CCC1=CC=CC=C1 DQNNXXFOHGSGFX-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 230000004580 weight loss Effects 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 3
- 229940123208 Biguanide Drugs 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- -1 (2-tert-butyl-4-methyl-phenoxypropionitrile) methane Chemical compound 0.000 description 2
- AUAGGMPIKOZAJZ-UHFFFAOYSA-N 1,3,6-trioxocane Chemical compound C1COCOCCO1 AUAGGMPIKOZAJZ-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- ZELCPEBYDWJHDX-UHFFFAOYSA-N 3-(4-methylphenoxy)propanenitrile Chemical compound CC1=CC=C(OCCC#N)C=C1 ZELCPEBYDWJHDX-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000000137 annealing Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 150000004862 dioxolanes Chemical class 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 238000012690 ionic polymerization Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 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
- C08K5/315—Compounds containing carbon-to-nitrogen triple bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE634203D BE634203A (en, 2012) | 1962-06-27 | ||
| NL294668D NL294668A (en, 2012) | 1962-06-27 | ||
| NL133445D NL133445C (en, 2012) | 1962-06-27 | ||
| DEF37167A DE1174064B (de) | 1962-06-27 | 1962-06-27 | Stabilisieren von polymeren Acetalen |
| CH782463A CH434742A (de) | 1962-06-27 | 1963-06-25 | Verfahren zur Stabilisierung von Mischpolymerisaten |
| US290625A US3300441A (en) | 1962-06-27 | 1963-06-26 | Polyacetals stabilized with phenoxypropionitriles |
| FR939536A FR1361673A (fr) | 1962-06-27 | 1963-06-27 | Procédé de stabilisation de polyacétals |
| GB25637/63A GB1042497A (en) | 1962-06-27 | 1963-06-27 | Stabilised polyacetals and process for making same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF37167A DE1174064B (de) | 1962-06-27 | 1962-06-27 | Stabilisieren von polymeren Acetalen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1174064B true DE1174064B (de) | 1964-07-16 |
Family
ID=7096765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF37167A Pending DE1174064B (de) | 1962-06-27 | 1962-06-27 | Stabilisieren von polymeren Acetalen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3300441A (en, 2012) |
| BE (1) | BE634203A (en, 2012) |
| CH (1) | CH434742A (en, 2012) |
| DE (1) | DE1174064B (en, 2012) |
| FR (1) | FR1361673A (en, 2012) |
| GB (1) | GB1042497A (en, 2012) |
| NL (2) | NL133445C (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1286753B (de) * | 1964-08-06 | 1969-01-09 | Tenneco Chem | Oligomere, stickstoffhaltige Acetale als Stabilisatoren fuer Polymerisate des Formaldehyds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE596389A (en, 2012) * | 1959-10-27 |
-
0
- NL NL294668D patent/NL294668A/xx unknown
- BE BE634203D patent/BE634203A/xx unknown
- NL NL133445D patent/NL133445C/xx active
-
1962
- 1962-06-27 DE DEF37167A patent/DE1174064B/de active Pending
-
1963
- 1963-06-25 CH CH782463A patent/CH434742A/de unknown
- 1963-06-26 US US290625A patent/US3300441A/en not_active Expired - Lifetime
- 1963-06-27 FR FR939536A patent/FR1361673A/fr not_active Expired
- 1963-06-27 GB GB25637/63A patent/GB1042497A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1286753B (de) * | 1964-08-06 | 1969-01-09 | Tenneco Chem | Oligomere, stickstoffhaltige Acetale als Stabilisatoren fuer Polymerisate des Formaldehyds |
Also Published As
| Publication number | Publication date |
|---|---|
| NL294668A (en, 2012) | |
| GB1042497A (en) | 1966-09-14 |
| NL133445C (en, 2012) | |
| US3300441A (en) | 1967-01-24 |
| BE634203A (en, 2012) | |
| FR1361673A (fr) | 1964-05-22 |
| CH434742A (de) | 1967-04-30 |
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