DE1169662B - Verfahren zum Stabilisieren von Niederdruck-Polyolefinen - Google Patents
Verfahren zum Stabilisieren von Niederdruck-PolyolefinenInfo
- Publication number
- DE1169662B DE1169662B DE1960P0024593 DEP0024593A DE1169662B DE 1169662 B DE1169662 B DE 1169662B DE 1960P0024593 DE1960P0024593 DE 1960P0024593 DE P0024593 A DEP0024593 A DE P0024593A DE 1169662 B DE1169662 B DE 1169662B
- Authority
- DE
- Germany
- Prior art keywords
- phosphite
- polyolefins
- phenolic
- tert
- bis
- 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
- 229920000098 polyolefin Polymers 0.000 title claims description 19
- 230000000087 stabilizing effect Effects 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 6
- 239000002530 phenolic antioxidant Substances 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 11
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 8
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 8
- 239000003381 stabilizer Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- -1 aralkyl radicals Chemical class 0.000 description 11
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical group CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 11
- 239000004698 Polyethylene Substances 0.000 description 8
- 239000003963 antioxidant agent Substances 0.000 description 8
- 150000002989 phenols Chemical class 0.000 description 8
- 229920000573 polyethylene Polymers 0.000 description 8
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 7
- 238000002845 discoloration Methods 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- HLKGSHWMTRQWIU-UHFFFAOYSA-N 4-(octadecylamino)phenol Chemical compound CCCCCCCCCCCCCCCCCCNC1=CC=C(O)C=C1 HLKGSHWMTRQWIU-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- QOQNJVLFFRMJTQ-UHFFFAOYSA-N trioctyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OCCCCCCCC QOQNJVLFFRMJTQ-UHFFFAOYSA-N 0.000 description 3
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 2
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 238000005098 hot rolling Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
- TVWVEVIMXUMGBE-UHFFFAOYSA-N 2-[(2-hydroxy-4-propan-2-ylphenyl)methyl]-5-propan-2-ylphenol Chemical compound OC1=CC(C(C)C)=CC=C1CC1=CC=C(C(C)C)C=C1O TVWVEVIMXUMGBE-UHFFFAOYSA-N 0.000 description 1
- UFCRKZJPBDDMSF-UHFFFAOYSA-N 4-(dodecylamino)phenol Chemical compound CCCCCCCCCCCCNC1=CC=C(O)C=C1 UFCRKZJPBDDMSF-UHFFFAOYSA-N 0.000 description 1
- DSBSGBZWKFJXGS-UHFFFAOYSA-N CC(C)(C)C(C=C1)=CC=C1C1=CC=CC(P(O)(O)O)=C1C1=CC=C(C(C)(C)C)C=C1 Chemical compound CC(C)(C)C(C=C1)=CC=C1C1=CC=CC(P(O)(O)O)=C1C1=CC=C(C(C)(C)C)C=C1 DSBSGBZWKFJXGS-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- NNBZCPXTIHJBJL-UHFFFAOYSA-N trans-decahydronaphthalene Natural products C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 1
- FICPQAZLPKLOLH-UHFFFAOYSA-N tricyclohexyl phosphite Chemical compound C1CCCCC1OP(OC1CCCCC1)OC1CCCCC1 FICPQAZLPKLOLH-UHFFFAOYSA-N 0.000 description 1
- DSKYTPNZLCVELA-UHFFFAOYSA-N trihexyl phosphite Chemical compound CCCCCCOP(OCCCCCC)OCCCCCC DSKYTPNZLCVELA-UHFFFAOYSA-N 0.000 description 1
- QUTZUATVZPXUJR-UHFFFAOYSA-N trinonyl phosphite Chemical compound CCCCCCCCCOP(OCCCCCCCCC)OCCCCCCCCC QUTZUATVZPXUJR-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- ILLOBGFGKYTZRO-UHFFFAOYSA-N tris(2-ethylhexyl) phosphite Chemical compound CCCCC(CC)COP(OCC(CC)CCCC)OCC(CC)CCCC ILLOBGFGKYTZRO-UHFFFAOYSA-N 0.000 description 1
- VAURMQDVZLSKAA-UHFFFAOYSA-N tris(4-propan-2-ylphenyl) phosphite Chemical compound C1=CC(C(C)C)=CC=C1OP(OC=1C=CC(=CC=1)C(C)C)OC1=CC=C(C(C)C)C=C1 VAURMQDVZLSKAA-UHFFFAOYSA-N 0.000 description 1
- SAAMKFBWYWFBNY-UHFFFAOYSA-N tris(4-tert-butylphenyl) phosphite Chemical compound C1=CC(C(C)(C)C)=CC=C1OP(OC=1C=CC(=CC=1)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1 SAAMKFBWYWFBNY-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04L—TRANSMISSION OF DIGITAL INFORMATION, e.g. TELEGRAPHIC COMMUNICATION
- H04L17/00—Apparatus or local circuits for transmitting or receiving codes wherein each character is represented by the same number of equal-length code elements, e.g. Baudot code
- H04L17/16—Apparatus or circuits at the receiving end
- H04L17/24—Apparatus or circuits at the receiving end using mechanical translation and type-head printing, e.g. type-wheel, type-cylinder
-
- 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
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/375—Thiols containing six-membered aromatic rings
-
- 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
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Computer Networks & Wireless Communication (AREA)
- Signal Processing (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Mechanical Operated Clutches (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB208356A GB803557A (en) | 1956-01-20 | 1956-01-20 | Improvements in or relating to polymeric materials comprising low pressure polyolefines |
| GB1307456 | 1956-12-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1169662B true DE1169662B (de) | 1964-05-06 |
Family
ID=26237233
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1065170D Pending DE1065170B (de) | 1956-01-20 | Verfahren zur Stabilisierung von Polyolefinen oder Mischpolymerisaten aus niedermolekularen Olefinen | |
| DE1960P0024593 Pending DE1169662B (de) | 1956-01-20 | 1960-03-11 | Verfahren zum Stabilisieren von Niederdruck-Polyolefinen |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1065170D Pending DE1065170B (de) | 1956-01-20 | Verfahren zur Stabilisierung von Polyolefinen oder Mischpolymerisaten aus niedermolekularen Olefinen |
Country Status (7)
| Country | Link |
|---|---|
| BE (2) | BE554304A (enrdf_load_stackoverflow) |
| CH (2) | CH271256A (enrdf_load_stackoverflow) |
| DE (2) | DE1169662B (enrdf_load_stackoverflow) |
| FR (1) | FR1164850A (enrdf_load_stackoverflow) |
| GB (3) | GB803557A (enrdf_load_stackoverflow) |
| IT (1) | IT567433A (enrdf_load_stackoverflow) |
| NL (3) | NL91891C (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2606358A1 (de) * | 1975-02-20 | 1976-09-02 | Ciba Geigy Ag | Stabilisatorensysteme aus triarylphosphiten und phenolen |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT583225A (enrdf_load_stackoverflow) * | 1955-06-06 | |||
| NL249322A (enrdf_load_stackoverflow) * | 1956-01-20 | |||
| NL109902C (enrdf_load_stackoverflow) * | 1958-08-11 | |||
| GB888673A (en) * | 1959-10-28 | 1962-01-31 | Sun Oil Co | Improvements in or relating to the stabilization of polyolefins |
| DE1183504B (de) * | 1960-04-11 | 1964-12-17 | Ethyl Corp | Verwendung von synergistisch wirkenden Gemischen aus Phosphitestern und Methylenbisphenolen zum Stabilisieren von Motorentreibstoffen, Schmiermitteln und hoehermolekularen oder polymeren Kohlenwasserstoffen gegen Autoxydation in der Waerme |
| BE604245A (enrdf_load_stackoverflow) * | 1960-05-27 | |||
| DE1220602B (de) * | 1960-08-04 | 1966-07-07 | Bergwerksgesellschaft Hibernia | Verfahren zum Stabilisieren von Polyolefinen |
| NL268592A (enrdf_load_stackoverflow) | 1960-08-27 | |||
| DE1149525B (de) | 1960-09-30 | 1963-05-30 | Basf Ag | Stabilisierte Formmassen auf Basis hochmolekularer Polyolefine |
| DE1184750B (de) * | 1960-11-18 | 1965-01-07 | Standard Oil Co | Stabilisierung von niederen Alkanoldiestern der Terephthalsaeure |
| NL274762A (enrdf_load_stackoverflow) * | 1961-02-15 | |||
| DE1237312B (de) * | 1961-06-27 | 1967-03-23 | Pure Chem Ltd | Formmassen aus Polymerisaten von Olefinen |
| US3349058A (en) * | 1963-03-18 | 1967-10-24 | Phillips Petroleum Co | Organic phosphites for prevention of void formation in polymer olefin structures |
| US3244662A (en) * | 1963-09-10 | 1966-04-05 | Nat Polychemicals Inc | Polymers stabilized by a combination of organic phosphites and organic borates |
| DE1224925B (de) * | 1964-10-03 | 1966-09-15 | Hoechst Ag | Verfahren zum Stabilisieren von fluessigen AEthylenpolymerisaten |
| NL129756C (enrdf_load_stackoverflow) * | 1965-04-21 | 1900-01-01 | ||
| GB1136578A (en) * | 1965-10-22 | 1968-12-11 | Nat Polychemicals Inc | Phosphite-borate stabilizers for rubber polymerizates |
| JPS5110864B2 (enrdf_load_stackoverflow) * | 1972-12-01 | 1976-04-07 | ||
| DE2448416A1 (de) * | 1973-10-11 | 1975-08-28 | Raychem Corp | Polymermassen |
| JPS5473842A (en) * | 1977-11-25 | 1979-06-13 | Mitsubishi Petrochem Co Ltd | Polyolefin resin composition |
| CA1118140A (en) * | 1979-01-11 | 1982-02-09 | William E. Horn, Jr. | Stabilized olefin polymers |
| IT1202611B (it) * | 1987-03-03 | 1989-02-09 | Enichem Sintesi | Composizione solida stabilizzante per polimeri sintetici |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE554304A (enrdf_load_stackoverflow) * | 1956-01-20 |
-
0
- NL NL249322D patent/NL249322A/xx unknown
- DE DENDAT1065170D patent/DE1065170B/de active Pending
- IT IT567433D patent/IT567433A/it unknown
- BE BE588566D patent/BE588566A/xx unknown
- BE BE554304D patent/BE554304A/xx unknown
- NL NL105466D patent/NL105466C/xx active
- NL NL91891D patent/NL91891C/xx active
-
1947
- 1947-04-02 CH CH271256D patent/CH271256A/fr unknown
-
1956
- 1956-01-20 GB GB208356A patent/GB803557A/en not_active Expired
-
1957
- 1957-01-18 FR FR1164850D patent/FR1164850A/fr not_active Expired
- 1957-01-18 CH CH4175257A patent/CH362847A/de unknown
-
1959
- 1959-03-13 GB GB878559A patent/GB846684A/en not_active Expired
- 1959-10-13 GB GB3466659A patent/GB866883A/en not_active Expired
-
1960
- 1960-03-11 DE DE1960P0024593 patent/DE1169662B/de active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE554304A (enrdf_load_stackoverflow) * | 1956-01-20 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2606358A1 (de) * | 1975-02-20 | 1976-09-02 | Ciba Geigy Ag | Stabilisatorensysteme aus triarylphosphiten und phenolen |
| US4290941A (en) | 1975-02-20 | 1981-09-22 | Ciba-Geigy Corporation | Stabilization systems from triarylphosphites and phenols |
| DE2606358C3 (de) * | 1975-02-20 | 1986-12-04 | Ciba-Geigy Ag, Basel | Verwendung von stabilisatorensystemen aus triarylphosphiten und phenolen |
Also Published As
| Publication number | Publication date |
|---|---|
| GB866883A (en) | 1961-05-03 |
| GB846684A (en) | 1960-08-31 |
| BE554304A (enrdf_load_stackoverflow) | |
| GB803557A (en) | 1958-10-29 |
| DE1065170B (de) | 1959-09-10 |
| NL91891C (enrdf_load_stackoverflow) | |
| BE588566A (enrdf_load_stackoverflow) | |
| FR1164850A (fr) | 1958-10-14 |
| NL249322A (enrdf_load_stackoverflow) | |
| IT567433A (enrdf_load_stackoverflow) | |
| NL105466C (enrdf_load_stackoverflow) | |
| CH362847A (de) | 1962-06-30 |
| CH271256A (fr) | 1950-10-15 |
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