DE2155287A1 - Verfahren zum stabilisieren von polyamiden - Google Patents
Verfahren zum stabilisieren von polyamidenInfo
- Publication number
- DE2155287A1 DE2155287A1 DE19712155287 DE2155287A DE2155287A1 DE 2155287 A1 DE2155287 A1 DE 2155287A1 DE 19712155287 DE19712155287 DE 19712155287 DE 2155287 A DE2155287 A DE 2155287A DE 2155287 A1 DE2155287 A1 DE 2155287A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- polyamide
- phenyl
- substituted
- radical
- 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 26
- 229920002647 polyamide Polymers 0.000 title claims description 26
- 238000000034 method Methods 0.000 title claims description 10
- 230000000087 stabilizing effect Effects 0.000 title claims description 6
- -1 naphthyl radical Chemical group 0.000 claims description 21
- 239000003381 stabilizer Substances 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 6
- 150000005840 aryl radicals Chemical group 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 230000001939 inductive effect Effects 0.000 claims description 4
- 230000001590 oxidative effect Effects 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 230000015556 catabolic process Effects 0.000 claims description 3
- 238000006731 degradation reaction Methods 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 12
- 230000006641 stabilisation Effects 0.000 description 12
- 238000011105 stabilization Methods 0.000 description 12
- 238000002845 discoloration Methods 0.000 description 10
- 229940035422 diphenylamine Drugs 0.000 description 8
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 8
- 229920002292 Nylon 6 Polymers 0.000 description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000010949 copper Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- VVLAIYIMMFWRFW-UHFFFAOYSA-N 2-hydroxyethylazanium;acetate Chemical compound CC(O)=O.NCCO VVLAIYIMMFWRFW-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 229920002302 Nylon 6,6 Polymers 0.000 description 3
- CJOBVZJTOIVNNF-UHFFFAOYSA-N cadmium sulfide Chemical compound [Cd]=S CJOBVZJTOIVNNF-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000004989 p-phenylenediamines Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- FPMMQTRBJAIZIF-UHFFFAOYSA-N 1-N,1-N-diphenyloctane-1,3-diamine Chemical compound NC(CCN(C1=CC=CC=C1)C1=CC=CC=C1)CCCCC FPMMQTRBJAIZIF-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 101100387923 Caenorhabditis elegans dos-1 gene Proteins 0.000 description 2
- KBSDGEWBAHRIBK-UHFFFAOYSA-N acetic acid;2-aminoethanol Chemical compound CC(O)=O.CC(O)=O.NCCO KBSDGEWBAHRIBK-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- YDLSUFFXJYEVHW-UHFFFAOYSA-N azonan-2-one Chemical compound O=C1CCCCCCCN1 YDLSUFFXJYEVHW-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 150000003951 lactams Chemical class 0.000 description 2
- 150000004988 m-phenylenediamines Chemical class 0.000 description 2
- 150000005002 naphthylamines Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- HYKKSTFHWQTJBB-UHFFFAOYSA-N 3-amino-n,n-diphenylbenzamide Chemical compound NC1=CC=CC(C(=O)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HYKKSTFHWQTJBB-UHFFFAOYSA-N 0.000 description 1
- WCHIHLCUOACESF-UHFFFAOYSA-N 3-amino-n,n-diphenylpropanamide Chemical compound C=1C=CC=CC=1N(C(=O)CCN)C1=CC=CC=C1 WCHIHLCUOACESF-UHFFFAOYSA-N 0.000 description 1
- RSPHWOYYWACCJK-UHFFFAOYSA-N 3-n,3-n-diphenylbenzene-1,3-diamine Chemical compound NC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 RSPHWOYYWACCJK-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- ZSJYGRSWBINSII-UHFFFAOYSA-N n',n'-diphenylbutane-1,4-diamine Chemical compound C=1C=CC=CC=1N(CCCCN)C1=CC=CC=C1 ZSJYGRSWBINSII-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- MOMGDEWWZBKDDR-UHFFFAOYSA-M sodium;3,4,5,6-tetrahydro-2h-azepin-7-olate Chemical compound [Na+].O=C1CCCCC[N-]1 MOMGDEWWZBKDDR-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 230000000007 visual effect 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
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)
- Polyamides (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE790974D BE790974A (fr) | 1971-11-06 | Procede de stabilisation des polyamides | |
| DE19712155287 DE2155287A1 (de) | 1971-11-06 | 1971-11-06 | Verfahren zum stabilisieren von polyamiden |
| CH1316172A CH564046A5 (enrdf_load_stackoverflow) | 1971-11-06 | 1972-09-07 | |
| IT5309772A IT966134B (it) | 1971-11-06 | 1972-09-30 | Procedimento per la stabilizzazione di poliammidi |
| FR7238953A FR2158489B1 (enrdf_load_stackoverflow) | 1971-11-06 | 1972-11-03 | |
| GB5073972A GB1401864A (en) | 1971-11-06 | 1972-11-03 | Process for stabilizing polyamides |
| NL7214973A NL7214973A (enrdf_load_stackoverflow) | 1971-11-06 | 1972-11-06 | |
| JP11038272A JPS4858050A (enrdf_load_stackoverflow) | 1971-11-06 | 1972-11-06 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712155287 DE2155287A1 (de) | 1971-11-06 | 1971-11-06 | Verfahren zum stabilisieren von polyamiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2155287A1 true DE2155287A1 (de) | 1973-05-24 |
Family
ID=5824443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712155287 Pending DE2155287A1 (de) | 1971-11-06 | 1971-11-06 | Verfahren zum stabilisieren von polyamiden |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4858050A (enrdf_load_stackoverflow) |
| BE (1) | BE790974A (enrdf_load_stackoverflow) |
| CH (1) | CH564046A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2155287A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2158489B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1401864A (enrdf_load_stackoverflow) |
| IT (1) | IT966134B (enrdf_load_stackoverflow) |
| NL (1) | NL7214973A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5924751A (ja) * | 1982-08-02 | 1984-02-08 | Toray Ind Inc | ポリアミド樹脂組成物 |
| JPS5927948A (ja) * | 1982-08-06 | 1984-02-14 | Toray Ind Inc | 樹脂組成物 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR906892A (fr) * | 1942-12-04 | 1946-02-22 | Ig Farbenindustrie Ag | Procédé pour empêcher des polymères linéaires contenant des groupes amides dans leur chaîne de devenir cassants |
-
0
- BE BE790974D patent/BE790974A/xx unknown
-
1971
- 1971-11-06 DE DE19712155287 patent/DE2155287A1/de active Pending
-
1972
- 1972-09-07 CH CH1316172A patent/CH564046A5/xx not_active IP Right Cessation
- 1972-09-30 IT IT5309772A patent/IT966134B/it active
- 1972-11-03 GB GB5073972A patent/GB1401864A/en not_active Expired
- 1972-11-03 FR FR7238953A patent/FR2158489B1/fr not_active Expired
- 1972-11-06 NL NL7214973A patent/NL7214973A/xx not_active Application Discontinuation
- 1972-11-06 JP JP11038272A patent/JPS4858050A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IT966134B (it) | 1974-02-11 |
| JPS4858050A (enrdf_load_stackoverflow) | 1973-08-15 |
| FR2158489B1 (enrdf_load_stackoverflow) | 1979-03-16 |
| FR2158489A1 (enrdf_load_stackoverflow) | 1973-06-15 |
| BE790974A (fr) | 1973-05-07 |
| NL7214973A (enrdf_load_stackoverflow) | 1973-05-08 |
| GB1401864A (en) | 1975-08-06 |
| CH564046A5 (enrdf_load_stackoverflow) | 1975-07-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |