DE1253453B - Verfahren zum Stabilisieren von Mischpolymerisaten aus AEthylen, einem alpha-Olefin umindestens einem mehrfach ungesaettigten Kohlenwasserstoff - Google Patents
Verfahren zum Stabilisieren von Mischpolymerisaten aus AEthylen, einem alpha-Olefin umindestens einem mehrfach ungesaettigten KohlenwasserstoffInfo
- Publication number
- DE1253453B DE1253453B DEC37126A DEC0037126A DE1253453B DE 1253453 B DE1253453 B DE 1253453B DE C37126 A DEC37126 A DE C37126A DE C0037126 A DEC0037126 A DE C0037126A DE 1253453 B DE1253453 B DE 1253453B
- Authority
- DE
- Germany
- Prior art keywords
- minutes
- rubber
- stabilizer
- ethylene
- alkyl
- 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
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims description 10
- 239000005977 Ethylene Substances 0.000 title claims description 10
- 229920001577 copolymer Polymers 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 7
- 230000000087 stabilizing effect Effects 0.000 title claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 3
- 229930195733 hydrocarbon Natural products 0.000 title claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 3
- 239000004711 α-olefin Substances 0.000 title description 5
- 229920001971 elastomer Polymers 0.000 claims description 31
- 239000005060 rubber Substances 0.000 claims description 31
- 239000003381 stabilizer Substances 0.000 claims description 30
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 12
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 150000004985 diamines Chemical class 0.000 claims description 9
- 230000006641 stabilisation Effects 0.000 claims description 9
- 238000011105 stabilization Methods 0.000 claims description 9
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000004898 kneading Methods 0.000 claims description 8
- 229920000181 Ethylene propylene rubber Polymers 0.000 claims description 7
- OUBMGJOQLXMSNT-UHFFFAOYSA-N N-isopropyl-N'-phenyl-p-phenylenediamine Chemical compound C1=CC(NC(C)C)=CC=C1NC1=CC=CC=C1 OUBMGJOQLXMSNT-UHFFFAOYSA-N 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 claims description 4
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- -1 2,2-methylene Chemical group 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 8
- 230000001681 protective effect Effects 0.000 description 7
- 238000012545 processing Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 229920005669 high impact polystyrene Polymers 0.000 description 3
- 239000004797 high-impact polystyrene Substances 0.000 description 3
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 230000003712 anti-aging effect Effects 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 2
- 229920005549 butyl rubber Polymers 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 2
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- 230000006855 networking Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 230000035882 stress Effects 0.000 description 2
- 230000008646 thermal stress Effects 0.000 description 2
- WTQBISBWKRKLIJ-YUMQZZPRSA-N (1R,4R)-5-methylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1[C@H]2C(=C)C[C@@H]1C=C2 WTQBISBWKRKLIJ-YUMQZZPRSA-N 0.000 description 1
- ADTDLWOIUYJQNC-GLVZAGOZSA-N (3e,5e)-deca-1,3,5-triene Chemical compound CCCC\C=C\C=C\C=C ADTDLWOIUYJQNC-GLVZAGOZSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- AOCXDTRLJHIFSV-UHFFFAOYSA-N 2-(4-aminobutylamino)ethane-1,1,1,2-tetrol Chemical compound NCCCCNC(O)C(O)(O)O AOCXDTRLJHIFSV-UHFFFAOYSA-N 0.000 description 1
- FKJVYOFPTRGCSP-UHFFFAOYSA-N 2-[3-aminopropyl(2-hydroxyethyl)amino]ethanol Chemical compound NCCCN(CCO)CCO FKJVYOFPTRGCSP-UHFFFAOYSA-N 0.000 description 1
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- KYCGURZGBKFEQB-UHFFFAOYSA-N n',n'-dibutylpropane-1,3-diamine Chemical compound CCCCN(CCCC)CCCN KYCGURZGBKFEQB-UHFFFAOYSA-N 0.000 description 1
- UQUPIHHYKUEXQD-UHFFFAOYSA-N n,n′-dimethyl-1,3-propanediamine Chemical compound CNCCCNC UQUPIHHYKUEXQD-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000010626 work up procedure 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
- C08K5/17—Amines; Quaternary ammonium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC37126A DE1253453B (de) | 1965-10-12 | 1965-10-12 | Verfahren zum Stabilisieren von Mischpolymerisaten aus AEthylen, einem alpha-Olefin umindestens einem mehrfach ungesaettigten Kohlenwasserstoff |
| FR78655A FR1495814A (fr) | 1965-10-12 | 1966-10-04 | Procédé pour stabiliser du caoutchouc non saturé d'éthylène et d'alpha-oléfine |
| NL6614293A NL6614293A (show.php) | 1965-10-12 | 1966-10-11 | |
| US585776A US3436370A (en) | 1964-10-16 | 1966-10-11 | Unsaturated ethylene-propylene rubbers stabilized with n,n-substituted diamines |
| GB45297/66A GB1153733A (en) | 1965-10-12 | 1966-10-11 | Process for Stabilising Unsaturated Ethylene-alpha-Olefine Rubber |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC37126A DE1253453B (de) | 1965-10-12 | 1965-10-12 | Verfahren zum Stabilisieren von Mischpolymerisaten aus AEthylen, einem alpha-Olefin umindestens einem mehrfach ungesaettigten Kohlenwasserstoff |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1253453B true DE1253453B (de) | 1967-11-02 |
Family
ID=7022653
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC37126A Pending DE1253453B (de) | 1964-10-16 | 1965-10-12 | Verfahren zum Stabilisieren von Mischpolymerisaten aus AEthylen, einem alpha-Olefin umindestens einem mehrfach ungesaettigten Kohlenwasserstoff |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE1253453B (show.php) |
| FR (1) | FR1495814A (show.php) |
| GB (1) | GB1153733A (show.php) |
| NL (1) | NL6614293A (show.php) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3106219A1 (de) * | 1980-02-19 | 1982-02-25 | Anic S.P.A., Palermo | "polyolefinzusammensetzungen, die gegenueber uv-bestrahlungen mit offenkettigen, gehinderten aminen stabilisiert sind" |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2891029A (en) * | 1956-03-30 | 1959-06-16 | Myron A Coler | Polymers of vinylidene monomers destaticized with partially hydroxyalkylated alkylene diamines |
| US2891027A (en) * | 1955-12-30 | 1959-06-16 | Myron A Coler | Non-electrostatic molding compositions containing hydroxyalkylated alkylene diamines |
| US2959567A (en) * | 1956-01-26 | 1960-11-08 | Dow Chemical Co | Polyethylene stabilized with tetraalkanol substituted ethylene diamines |
-
1965
- 1965-10-12 DE DEC37126A patent/DE1253453B/de active Pending
-
1966
- 1966-10-04 FR FR78655A patent/FR1495814A/fr not_active Expired
- 1966-10-11 NL NL6614293A patent/NL6614293A/xx unknown
- 1966-10-11 GB GB45297/66A patent/GB1153733A/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2891027A (en) * | 1955-12-30 | 1959-06-16 | Myron A Coler | Non-electrostatic molding compositions containing hydroxyalkylated alkylene diamines |
| US2959567A (en) * | 1956-01-26 | 1960-11-08 | Dow Chemical Co | Polyethylene stabilized with tetraalkanol substituted ethylene diamines |
| US2891029A (en) * | 1956-03-30 | 1959-06-16 | Myron A Coler | Polymers of vinylidene monomers destaticized with partially hydroxyalkylated alkylene diamines |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3106219A1 (de) * | 1980-02-19 | 1982-02-25 | Anic S.P.A., Palermo | "polyolefinzusammensetzungen, die gegenueber uv-bestrahlungen mit offenkettigen, gehinderten aminen stabilisiert sind" |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1153733A (en) | 1969-05-29 |
| NL6614293A (show.php) | 1967-04-13 |
| FR1495814A (fr) | 1967-09-22 |
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