DE1795554A1 - Verfahren zur Herstellung oxydationsbestaendiger,nicht verfaerbender Polyamide - Google Patents
Verfahren zur Herstellung oxydationsbestaendiger,nicht verfaerbender PolyamideInfo
- Publication number
- DE1795554A1 DE1795554A1 DE19631795554 DE1795554A DE1795554A1 DE 1795554 A1 DE1795554 A1 DE 1795554A1 DE 19631795554 DE19631795554 DE 19631795554 DE 1795554 A DE1795554 A DE 1795554A DE 1795554 A1 DE1795554 A1 DE 1795554A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- radical
- phosphonic acid
- methyl
- formula
- 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
- 239000004952 Polyamide Substances 0.000 title claims description 14
- 229920002647 polyamide Polymers 0.000 title claims description 14
- 230000003647 oxidation Effects 0.000 title claims description 8
- 238000007254 oxidation reaction Methods 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- -1 alkylene radical Chemical class 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 150000003008 phosphonic acid esters Chemical class 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 150000003951 lactams Chemical class 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 229920002292 Nylon 6 Polymers 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- YXYYZPDGOACFLV-UHFFFAOYSA-N 1-diethoxyphosphorylpentylbenzene Chemical compound CCCCC(P(=O)(OCC)OCC)C1=CC=CC=C1 YXYYZPDGOACFLV-UHFFFAOYSA-N 0.000 description 1
- PDUVJLSXQXHZIJ-UHFFFAOYSA-N 2,6-ditert-butyl-4-(dihexoxyphosphorylmethyl)phenol Chemical compound C(CCCCC)OP(OCCCCCC)(=O)CC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C PDUVJLSXQXHZIJ-UHFFFAOYSA-N 0.000 description 1
- NDVPMPWUSJFFGS-UHFFFAOYSA-N CCC(C)(C)C1=CC(CP(OC)(OC)=O)=CC(C(C)(C)CC)=C1O Chemical compound CCC(C)(C)C1=CC(CP(OC)(OC)=O)=CC(C(C)(C)CC)=C1O NDVPMPWUSJFFGS-UHFFFAOYSA-N 0.000 description 1
- 241001579678 Panthea coenobita Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- JDQYAPMFWOTTIO-UHFFFAOYSA-N decoxy-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]phosphinic acid Chemical compound CCCCCCCCCCOP(O)(=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 JDQYAPMFWOTTIO-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/42—Polyamides containing atoms other than carbon, hydrogen, oxygen, and nitrogen
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1449062A CH433743A (de) | 1962-12-11 | 1962-12-11 | Verfahren zur Herstellung von Polyamiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1795554A1 true DE1795554A1 (de) | 1972-01-13 |
Family
ID=4401267
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631795554 Pending DE1795554A1 (de) | 1962-12-11 | 1963-12-10 | Verfahren zur Herstellung oxydationsbestaendiger,nicht verfaerbender Polyamide |
| DE19631495945 Pending DE1495945A1 (de) | 1962-12-11 | 1963-12-10 | Verfahren zur Herstellung oxydationsbestaendiger,nicht verfaerbender Polyamide |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631495945 Pending DE1495945A1 (de) | 1962-12-11 | 1963-12-10 | Verfahren zur Herstellung oxydationsbestaendiger,nicht verfaerbender Polyamide |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE641075A (Direct) |
| CH (2) | CH433745A (Direct) |
| DE (2) | DE1795554A1 (Direct) |
| GB (1) | GB992736A (Direct) |
| NL (2) | NL301602A (Direct) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL366777A1 (en) | 2001-06-14 | 2005-02-07 | Basf Corporation | Light-stabilized polymers comprising light-stabilizing moieties, articles therefrom and a method of making the same |
-
0
- NL NL137487D patent/NL137487C/xx active
- NL NL301602D patent/NL301602A/xx unknown
-
1962
- 1962-12-11 CH CH363767A patent/CH433745A/de unknown
- 1962-12-11 CH CH1449062A patent/CH433743A/de unknown
-
1963
- 1963-12-10 DE DE19631795554 patent/DE1795554A1/de active Pending
- 1963-12-10 GB GB4876763A patent/GB992736A/en not_active Expired
- 1963-12-10 BE BE641075A patent/BE641075A/xx unknown
- 1963-12-10 DE DE19631495945 patent/DE1495945A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL137487C (Direct) | |
| NL301602A (Direct) | |
| CH433743A (de) | 1967-04-15 |
| BE641075A (Direct) | 1964-06-10 |
| DE1495945A1 (de) | 1970-02-05 |
| CH433745A (de) | 1967-04-15 |
| GB992736A (en) | 1965-05-19 |
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