DE1129689B - Verfahren zum Stabilisieren von makromolekularen Polyacetalen gegen die gleichzeitige Einwirkung von Hitze und Sauerstoff mit stickstoff-haltigen polymeren Verbindungen - Google Patents
Verfahren zum Stabilisieren von makromolekularen Polyacetalen gegen die gleichzeitige Einwirkung von Hitze und Sauerstoff mit stickstoff-haltigen polymeren VerbindungenInfo
- Publication number
- DE1129689B DE1129689B DEF31823A DEF0031823A DE1129689B DE 1129689 B DE1129689 B DE 1129689B DE F31823 A DEF31823 A DE F31823A DE F0031823 A DEF0031823 A DE F0031823A DE 1129689 B DE1129689 B DE 1129689B
- Authority
- DE
- Germany
- Prior art keywords
- weight
- nitrogen
- polyacetals
- oxygen
- heat
- 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 44
- 229920000642 polymer Polymers 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 10
- 230000000087 stabilizing effect Effects 0.000 title claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims description 6
- 239000001301 oxygen Substances 0.000 title claims description 6
- 229910052760 oxygen Inorganic materials 0.000 title claims description 6
- 229930182556 Polyacetal Natural products 0.000 claims description 16
- -1 polyoxymethylenes Polymers 0.000 claims description 7
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 239000004611 light stabiliser Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 29
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 16
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 16
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 16
- 239000003381 stabilizer Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 8
- 239000000155 melt Substances 0.000 description 8
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 239000004952 Polyamide Substances 0.000 description 4
- PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 description 4
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 4
- 229930006739 camphene Natural products 0.000 description 4
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- HKYYJZABVBDWJU-UHFFFAOYSA-N 1-(octadecyltrisulfanyl)octadecane Chemical compound CCCCCCCCCCCCCCCCCCSSSCCCCCCCCCCCCCCCCCC HKYYJZABVBDWJU-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 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
- 238000005259 measurement Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 238000010525 oxidative degradation reaction Methods 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 2
- 229960002447 thiram Drugs 0.000 description 2
- AUAGGMPIKOZAJZ-UHFFFAOYSA-N 1,3,6-trioxocane Chemical compound C1COCOCCO1 AUAGGMPIKOZAJZ-UHFFFAOYSA-N 0.000 description 1
- IHWDIGHWDQPQMQ-UHFFFAOYSA-N 1-octadecylsulfanyloctadecane Chemical compound CCCCCCCCCCCCCCCCCCSCCCCCCCCCCCCCCCCCC IHWDIGHWDQPQMQ-UHFFFAOYSA-N 0.000 description 1
- ZOMWPAHEBIICIQ-UHFFFAOYSA-N 2,4-dimethyl-6-(4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl)phenol Chemical compound CC1=CC(C)=C(O)C(C2C3(C)CCC(C3(C)C)C2)=C1 ZOMWPAHEBIICIQ-UHFFFAOYSA-N 0.000 description 1
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 1
- KUMMBDBTERQYCG-UHFFFAOYSA-N 2,6-bis(hydroxymethyl)-4-methylphenol Chemical compound CC1=CC(CO)=C(O)C(CO)=C1 KUMMBDBTERQYCG-UHFFFAOYSA-N 0.000 description 1
- NFLKRYVCLBAZDZ-UHFFFAOYSA-N 2-(9-methoxynonyl)phenol Chemical compound COCCCCCCCCCC1=C(C=CC=C1)O NFLKRYVCLBAZDZ-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- YDLSUFFXJYEVHW-UHFFFAOYSA-N azonan-2-one Chemical compound O=C1CCCCCCCN1 YDLSUFFXJYEVHW-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000005496 tempering Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000010792 warming 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
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L59/00—Compositions of polyacetals; Compositions of derivatives of polyacetals
- C08L59/02—Polyacetals containing polyoxymethylene sequences only
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L39/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
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)
- Polyethers (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL125931D NL125931C (Sortimente) | 1960-08-03 | ||
| NL267701D NL267701A (Sortimente) | 1960-08-03 | ||
| DEF31823A DE1129689B (de) | 1960-08-03 | 1960-08-03 | Verfahren zum Stabilisieren von makromolekularen Polyacetalen gegen die gleichzeitige Einwirkung von Hitze und Sauerstoff mit stickstoff-haltigen polymeren Verbindungen |
| CH900361A CH405710A (de) | 1960-08-03 | 1961-08-01 | Verfahren zur Stabilisierung von Polyacetalen |
| BE606874A BE606874A (fr) | 1960-08-03 | 1961-08-03 | Procédé de stabilisation de polyacétals. |
| GB2828961A GB989183A (en) | 1960-08-03 | 1961-08-03 | Stabilised polyoxyalkylenes and process for preparing them |
| FR869993A FR1296904A (fr) | 1960-08-03 | 1961-08-03 | Procédé de stabilisation de polyacétals |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF31823A DE1129689B (de) | 1960-08-03 | 1960-08-03 | Verfahren zum Stabilisieren von makromolekularen Polyacetalen gegen die gleichzeitige Einwirkung von Hitze und Sauerstoff mit stickstoff-haltigen polymeren Verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1129689B true DE1129689B (de) | 1962-05-17 |
Family
ID=7094370
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF31823A Pending DE1129689B (de) | 1960-08-03 | 1960-08-03 | Verfahren zum Stabilisieren von makromolekularen Polyacetalen gegen die gleichzeitige Einwirkung von Hitze und Sauerstoff mit stickstoff-haltigen polymeren Verbindungen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE606874A (Sortimente) |
| CH (1) | CH405710A (Sortimente) |
| DE (1) | DE1129689B (Sortimente) |
| GB (1) | GB989183A (Sortimente) |
| NL (2) | NL267701A (Sortimente) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1218152B (de) * | 1962-12-20 | 1966-06-02 | Dynamit Nobel Ag | Stickstoff im Ring enthaltende Verbindungen als Stabilisatoren fuer Polyaether |
-
0
- NL NL125931D patent/NL125931C/xx active
- NL NL267701D patent/NL267701A/xx unknown
-
1960
- 1960-08-03 DE DEF31823A patent/DE1129689B/de active Pending
-
1961
- 1961-08-01 CH CH900361A patent/CH405710A/de unknown
- 1961-08-03 BE BE606874A patent/BE606874A/fr unknown
- 1961-08-03 GB GB2828961A patent/GB989183A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1218152B (de) * | 1962-12-20 | 1966-06-02 | Dynamit Nobel Ag | Stickstoff im Ring enthaltende Verbindungen als Stabilisatoren fuer Polyaether |
Also Published As
| Publication number | Publication date |
|---|---|
| GB989183A (en) | 1965-04-14 |
| NL125931C (Sortimente) | |
| BE606874A (fr) | 1962-02-05 |
| NL267701A (Sortimente) | |
| CH405710A (de) | 1966-01-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1290712B (de) | Gegen den Abbau durch Licht und Waerme stabilisierte Formmassen | |
| DE1117868B (de) | Verfahren zum Stabilisieren von makromolekularen Polyoxymethylenen und dessen Derivaten durch schwefelhaltige Verbindungen | |
| DE19681192B4 (de) | Verfahren zur Herstellung eines stabilisierten Oxymethylen-Copolymeren | |
| DE1129689B (de) | Verfahren zum Stabilisieren von makromolekularen Polyacetalen gegen die gleichzeitige Einwirkung von Hitze und Sauerstoff mit stickstoff-haltigen polymeren Verbindungen | |
| DE2636089A1 (de) | Polymermischungen | |
| DE2331354B2 (de) | Verfahren zur Herstellung von Polypropylen | |
| DE1149896B (de) | Stabilisieren von makromolekularen Polyacetalen | |
| DE1041243B (de) | Verfahren zur Stabilisierung von Polyolefinen gegen termische Oxydation | |
| EP1448691A1 (de) | Verfahren zur herstellung von polykondensaten | |
| DE1911790C3 (de) | Stabilisierte Polyoxymethylenmasse und Verfahren zu ihrer Herstellung | |
| DE1149897B (de) | Stabilisieren von Massen, die makromolekulare Polyacetalen enthalten | |
| AT228500B (de) | Verfahren zur Stabilisierung von Polyacetalen | |
| DE2638855C3 (de) | Verwendung von Quadratsäureamiden als Stabilisierungsmittel für geformte oder nicht geformte Kunststoffe | |
| DE1165263B (de) | Stabilisieren von Polyoxymethylenen | |
| DE1917455C3 (de) | Stabilisierte Formaldehyd-Polymerisat-Formmassen | |
| DE1105161B (de) | Verfahren zum Stabilisieren von makromolekularem Polyformaldehyd | |
| DE1147753B (de) | Gegen Licht stabilisierte Formmassen aus festen Polymeren eines ª‡-Olefins mit wenigstens 3 Kohlenstoffatomen | |
| DE2946954C2 (de) | Verfahren zur Stabilisierung von Hochdruckpolyethylen | |
| DE1265409B (de) | Verfahren zum Stabilisieren von Polyolefinen | |
| DE1768952A1 (de) | Verfahren zur Herstellung von Paraformaldehyd | |
| AT232733B (de) | Verfahren zur Stabilisierung hochmolekularer Polyacetale | |
| DE1154620B (de) | Verfahren zum Vernetzen von Polyaethylenmassen | |
| DE2056263A1 (de) | Stabilisierte Polyoxymethylenform massen und ihre Verwendung zur Herstellung von Formkorpern | |
| DE10247470A1 (de) | Abbaustabiles Polyamid und Verfahren zu dessen Herstellung | |
| DE1234018B (de) | Stabilisierungsmittel fuer Celluloseester |