DE1104695B - Verfahren zum Stabilisieren von Polymeren des Formaldehyds - Google Patents
Verfahren zum Stabilisieren von Polymeren des FormaldehydsInfo
- Publication number
- DE1104695B DE1104695B DEF26948A DEF0026948A DE1104695B DE 1104695 B DE1104695 B DE 1104695B DE F26948 A DEF26948 A DE F26948A DE F0026948 A DEF0026948 A DE F0026948A DE 1104695 B DE1104695 B DE 1104695B
- Authority
- DE
- Germany
- Prior art keywords
- formaldehyde
- acid diamide
- amides
- acid
- polymers
- 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
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title claims description 54
- 229920000642 polymer Polymers 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 8
- 230000000087 stabilizing effect Effects 0.000 title claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 150000001408 amides Chemical class 0.000 claims description 12
- 239000003381 stabilizer Substances 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 claims description 6
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- SNCZNSNPXMPCGN-UHFFFAOYSA-N butanediamide Chemical compound NC(=O)CCC(N)=O SNCZNSNPXMPCGN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
- 229920006324 polyoxymethylene Polymers 0.000 description 12
- -1 nitrogen Stearic hydrazide Chemical compound 0.000 description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002429 hydrazines Chemical class 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BSSNZUFKXJJCBG-OWOJBTEDSA-N (e)-but-2-enediamide Chemical compound NC(=O)\C=C\C(N)=O BSSNZUFKXJJCBG-OWOJBTEDSA-N 0.000 description 1
- ZVMAGJJPTALGQB-UHFFFAOYSA-N 2-[3-(carboxymethoxy)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=CC(OCC(O)=O)=C1 ZVMAGJJPTALGQB-UHFFFAOYSA-N 0.000 description 1
- MPQPXMRGNQJXGO-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxamide Chemical compound NC(=O)CC(O)(C(N)=O)CC(N)=O MPQPXMRGNQJXGO-UHFFFAOYSA-N 0.000 description 1
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 description 1
- GRMNJXQBRPJVQV-UHFFFAOYSA-N Diamide-Tartaric acid Natural products NC(=O)C(O)C(O)C(N)=O GRMNJXQBRPJVQV-UHFFFAOYSA-N 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- FCOLQLZWSWGHRB-UHFFFAOYSA-N butane-1,1,1,2-tetracarboxamide Chemical compound CCC(C(N)=O)C(C(N)=O)(C(N)=O)C(N)=O FCOLQLZWSWGHRB-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- QZUPTXGVPYNUIT-UHFFFAOYSA-N isophthalamide Chemical compound NC(=O)C1=CC=CC(C(N)=O)=C1 QZUPTXGVPYNUIT-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- ZWXJWAPTSTYSAH-UHFFFAOYSA-N n,n'-dimethylpropanediamide Chemical compound CNC(=O)CC(=O)NC ZWXJWAPTSTYSAH-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004580 weight loss Effects 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
-
- 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
- C08K5/20—Carboxylic acid amides
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)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL244788D NL244788A (en, 2012) | 1958-11-03 | ||
| NL128292D NL128292C (en, 2012) | 1958-11-03 | ||
| DEF26948A DE1104695B (de) | 1958-11-03 | 1958-11-03 | Verfahren zum Stabilisieren von Polymeren des Formaldehyds |
| US847871A US3131165A (en) | 1958-11-03 | 1959-10-22 | Amide stabilized formaldehyde polymers and process for preparing same |
| CH8007559A CH389244A (de) | 1958-11-03 | 1959-10-30 | Verfahren zum Stabilisieren von Polymeren des Formaldehyds |
| FR809096A FR1239672A (fr) | 1958-11-03 | 1959-11-02 | Procédé de stabilisation de polymères du formaldéhyde |
| BE584257A BE584257A (fr) | 1958-11-03 | 1959-11-03 | Procédé de stabilisation de polymères du formaldéhyde |
| GB37341/59A GB914708A (en) | 1958-11-03 | 1959-11-03 | The stabilization of polymeric-formaldehydes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF26948A DE1104695B (de) | 1958-11-03 | 1958-11-03 | Verfahren zum Stabilisieren von Polymeren des Formaldehyds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1104695B true DE1104695B (de) | 1961-04-13 |
Family
ID=7092229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF26948A Pending DE1104695B (de) | 1958-11-03 | 1958-11-03 | Verfahren zum Stabilisieren von Polymeren des Formaldehyds |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3131165A (en, 2012) |
| BE (1) | BE584257A (en, 2012) |
| CH (1) | CH389244A (en, 2012) |
| DE (1) | DE1104695B (en, 2012) |
| FR (1) | FR1239672A (en, 2012) |
| GB (1) | GB914708A (en, 2012) |
| NL (2) | NL128292C (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1152256B (de) * | 1960-08-20 | 1963-08-01 | Degussa | Verwendung von Amiden zum Erhoehen der Kerbschlagzaehigkeit in Massen aus hochmolekularen Polyoxymethylenen |
| WO2005059030A1 (de) | 2003-12-18 | 2005-06-30 | Ticona Gmbh | Polyoxymethylen formmassen und deren verwendung |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL260309A (en, 2012) * | 1960-01-21 | |||
| NL127335C (en, 2012) * | 1961-04-13 | |||
| US3382293A (en) * | 1962-02-12 | 1968-05-07 | Celanese Corp | Polyoxymethylene blended with phenolic novolac |
| BE626284A (en, 2012) * | 1962-04-28 | |||
| BE631683A (en, 2012) * | 1962-04-28 | |||
| NL280493A (en, 2012) * | 1962-07-03 | |||
| US3262906A (en) * | 1962-09-20 | 1966-07-26 | Monsanto Co | Stabilization of polyaldehydes with quinoline compounds |
| US3262907A (en) * | 1962-09-20 | 1966-07-26 | Monsanto Co | Stabilization of polyaldehydes with benzothiazole and derivatives thereof |
| US3267068A (en) * | 1962-10-18 | 1966-08-16 | Monsanto Co | Polyaldehyde compositions containing a monoaminonaphthalene and a trialkyl phosphite |
| US3274149A (en) * | 1963-02-13 | 1966-09-20 | Celanese Corp | Oxymethylene polymers stabilized with amino substituted amides |
| DE1301545B (de) * | 1963-06-14 | 1969-08-21 | Toyo Rayon Co Ltd | Verfahren zum Stabilisieren von makromolekularen Polyoxymethylenen |
| NL129037C (en, 2012) * | 1963-07-29 | |||
| US3337505A (en) * | 1963-10-08 | 1967-08-22 | Toho Rayon Kk | Process to improve heat stability of polyoxymethylene |
| GB1063573A (en) * | 1964-01-23 | 1967-03-30 | Asahi Chemical Ind | Method for the production of trioxane copolymer containing nitrogen |
| DE2348808C3 (de) * | 1973-09-28 | 1980-10-09 | Hoechst Ag, 6000 Frankfurt | Formmasse auf Poly(oxymethylen)-Basis |
| US4179370A (en) * | 1974-07-03 | 1979-12-18 | Chemische Fabrik Stockhause & Cie | Flocculating agent comprising water-in-oil emulsion of stabilizer plus NH-active polymer carrying formaldehyde and amine radicals |
| US4113685A (en) * | 1975-01-02 | 1978-09-12 | Chemische Fabrik Stockhausen & Cie | Flocculating agent comprising water-in-oil emulsion of stabilizer plus NH-active polymer carrying formaldehyde and amine radicals |
| US4130604A (en) * | 1976-12-17 | 1978-12-19 | Celanese Corporation | Production of an improved polyoxymethylene molding composition which forms reduced mold deposits upon molding |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB748856A (en) * | 1952-12-23 | 1956-05-09 | Du Pont | Improvements in or relating to formaldehyde polymers and methods of preparing the same |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA573789A (en) * | 1959-04-07 | G. Alsup Richard | Polyoxymethylene compositions stabilized with a synthetic polyamide | |
| US2296249A (en) * | 1940-08-26 | 1942-09-22 | Du Pont | Polymers of formaldehyde |
| US2844561A (en) * | 1953-06-30 | 1958-07-22 | Du Pont | Dispersion polymerization of formaldehyde in the presence of an organic synthetic polymer |
| US2993025A (en) * | 1956-07-26 | 1961-07-18 | Du Pont | Polyoxymethylene compositions stabilized with a synthetic superpolyamide |
| NL219323A (en, 2012) * | 1956-07-26 | |||
| US3001966A (en) * | 1958-08-18 | 1961-09-26 | Du Pont | Thermally-stabilized polyacetaldehyde elastomers, process for their preparation and mixtures of same with polycarbonamides |
-
0
- NL NL244788D patent/NL244788A/xx unknown
- NL NL128292D patent/NL128292C/xx active
-
1958
- 1958-11-03 DE DEF26948A patent/DE1104695B/de active Pending
-
1959
- 1959-10-22 US US847871A patent/US3131165A/en not_active Expired - Lifetime
- 1959-10-30 CH CH8007559A patent/CH389244A/de unknown
- 1959-11-02 FR FR809096A patent/FR1239672A/fr not_active Expired
- 1959-11-03 GB GB37341/59A patent/GB914708A/en not_active Expired
- 1959-11-03 BE BE584257A patent/BE584257A/fr unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB748856A (en) * | 1952-12-23 | 1956-05-09 | Du Pont | Improvements in or relating to formaldehyde polymers and methods of preparing the same |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1152256B (de) * | 1960-08-20 | 1963-08-01 | Degussa | Verwendung von Amiden zum Erhoehen der Kerbschlagzaehigkeit in Massen aus hochmolekularen Polyoxymethylenen |
| WO2005059030A1 (de) | 2003-12-18 | 2005-06-30 | Ticona Gmbh | Polyoxymethylen formmassen und deren verwendung |
Also Published As
| Publication number | Publication date |
|---|---|
| NL128292C (en, 2012) | |
| FR1239672A (fr) | 1960-08-26 |
| CH389244A (de) | 1965-03-15 |
| GB914708A (en) | 1963-01-02 |
| BE584257A (fr) | 1960-05-03 |
| NL244788A (en, 2012) | |
| US3131165A (en) | 1964-04-28 |
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