DE2331354B2 - Verfahren zur Herstellung von Polypropylen - Google Patents
Verfahren zur Herstellung von PolypropylenInfo
- Publication number
- DE2331354B2 DE2331354B2 DE2331354A DE2331354A DE2331354B2 DE 2331354 B2 DE2331354 B2 DE 2331354B2 DE 2331354 A DE2331354 A DE 2331354A DE 2331354 A DE2331354 A DE 2331354A DE 2331354 B2 DE2331354 B2 DE 2331354B2
- Authority
- DE
- Germany
- Prior art keywords
- tert
- peroxide
- polypropylene
- butyl
- stabilized
- 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.)
- Withdrawn
Links
- -1 polypropylene Polymers 0.000 title claims description 31
- 239000004743 Polypropylene Substances 0.000 title claims description 25
- 229920001155 polypropylene Polymers 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000002978 peroxides Chemical class 0.000 claims description 28
- 230000015556 catabolic process Effects 0.000 claims description 12
- 238000006731 degradation reaction Methods 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 9
- 239000004611 light stabiliser Substances 0.000 claims description 7
- 239000002530 phenolic antioxidant Substances 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
- 239000003963 antioxidant agent Substances 0.000 description 12
- 239000004342 Benzoyl peroxide Substances 0.000 description 9
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 9
- 235000019400 benzoyl peroxide Nutrition 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 8
- 239000003381 stabilizer Substances 0.000 description 8
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 230000003078 antioxidant effect Effects 0.000 description 6
- 230000006698 induction Effects 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical class OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 230000000593 degrading effect Effects 0.000 description 4
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 4
- UBRWPVTUQDJKCC-UHFFFAOYSA-N 1,3-bis(2-tert-butylperoxypropan-2-yl)benzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC(C(C)(C)OOC(C)(C)C)=C1 UBRWPVTUQDJKCC-UHFFFAOYSA-N 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- 239000003490 Thiodipropionic acid Substances 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 235000019303 thiodipropionic acid Nutrition 0.000 description 3
- YKTNISGZEGZHIS-UHFFFAOYSA-N 2-$l^{1}-oxidanyloxy-2-methylpropane Chemical group CC(C)(C)O[O] YKTNISGZEGZHIS-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- XXQBEVHPUKOQEO-UHFFFAOYSA-N potassium superoxide Chemical compound [K+].[K+].[O-][O-] XXQBEVHPUKOQEO-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- ZEBMSMUPGIOANU-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methylphosphonic acid Chemical compound CC(C)(C)C1=CC(CP(O)(O)=O)=CC(C(C)(C)C)=C1O ZEBMSMUPGIOANU-UHFFFAOYSA-N 0.000 description 1
- WWXLTYINQKXZNK-UHFFFAOYSA-N 1-(hydroperoxymethylperoxy)butane Chemical compound CCCCOOCOO WWXLTYINQKXZNK-UHFFFAOYSA-N 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- JJRDRFZYKKFYMO-UHFFFAOYSA-N 2-methyl-2-(2-methylbutan-2-ylperoxy)butane Chemical compound CCC(C)(C)OOC(C)(C)CC JJRDRFZYKKFYMO-UHFFFAOYSA-N 0.000 description 1
- PZBQVZFITSVHAW-UHFFFAOYSA-N 5-chloro-2h-benzotriazole Chemical compound C1=C(Cl)C=CC2=NNN=C21 PZBQVZFITSVHAW-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- LGGDYZQEROEDGP-UHFFFAOYSA-N benzoyl benzenecarboperoxoate;1-dodecylperoxydodecane Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1.CCCCCCCCCCCCOOCCCCCCCCCCCC LGGDYZQEROEDGP-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-N disulfuric acid Chemical compound OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- WNZQDUSMALZDQF-UHFFFAOYSA-N isobenzofuranone Natural products C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 1
- YASWBJXTHOXPGK-UHFFFAOYSA-N n-(4-hydroxyphenyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC1=CC=C(O)C=C1 YASWBJXTHOXPGK-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- YTXCAJNHPVBVDJ-UHFFFAOYSA-N octadecyl propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CC YTXCAJNHPVBVDJ-UHFFFAOYSA-N 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000019394 potassium persulphate Nutrition 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-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
- 239000004711 α-olefin Substances 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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/50—Partial depolymerisation
-
- 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
- C08K5/14—Peroxides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT636872A AT319589B (de) | 1972-07-25 | 1972-07-25 | Verfahren zur Herstellung von Polypropylen |
| FR7326278A FR2193840A1 (en) | 1972-07-25 | 1973-07-18 | Polypropylene with narrow mol wt distribution |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2331354A1 DE2331354A1 (de) | 1974-02-14 |
| DE2331354B2 true DE2331354B2 (de) | 1980-02-07 |
Family
ID=25603032
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2331354A Withdrawn DE2331354B2 (de) | 1972-07-25 | 1973-06-20 | Verfahren zur Herstellung von Polypropylen |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5219595B2 (enrdf_load_html_response) |
| AT (1) | AT319589B (enrdf_load_html_response) |
| BE (1) | BE806669A (enrdf_load_html_response) |
| CS (1) | CS174891B2 (enrdf_load_html_response) |
| DE (1) | DE2331354B2 (enrdf_load_html_response) |
| GB (1) | GB1442681A (enrdf_load_html_response) |
| IE (1) | IE38160B1 (enrdf_load_html_response) |
| NL (1) | NL161468C (enrdf_load_html_response) |
| SE (1) | SE410970B (enrdf_load_html_response) |
| ZA (1) | ZA734828B (enrdf_load_html_response) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3742845A1 (de) * | 1987-12-17 | 1989-07-13 | Lentia Gmbh | Verfahren zur herstellung von faserverstaerkten polypropylenbahnen sowie faserverstaerkte polypropylenbahnen |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56109135U (enrdf_load_html_response) * | 1980-01-25 | 1981-08-24 | ||
| US4451589A (en) * | 1981-06-15 | 1984-05-29 | Kimberly-Clark Corporation | Method of improving processability of polymers and resulting polymer compositions |
| JPS6099108A (ja) * | 1983-11-04 | 1985-06-03 | Tokuyama Soda Co Ltd | ポリプロピレン成形品の製造方法 |
| JP3016880B2 (ja) * | 1991-02-01 | 2000-03-06 | 三菱化学株式会社 | フィルム成形用高結晶性ポリプロピレン |
| AT403581B (de) * | 1993-06-07 | 1998-03-25 | Danubia Petrochem Polymere | Verfahren zur herstellung von neuen polypropylenen durch chemische degradierung |
| US5622772A (en) * | 1994-06-03 | 1997-04-22 | Kimberly-Clark Corporation | Highly crimpable spunbond conjugate fibers and nonwoven webs made therefrom |
| US5808110A (en) * | 1994-07-21 | 1998-09-15 | Akzo Nobel Nv | Cyclic ketone peroxide formulations |
| KR20070046728A (ko) * | 2005-10-31 | 2007-05-03 | 스미또모 가가꾸 가부시끼가이샤 | 과립 물질 |
| EP1987070B1 (en) * | 2006-02-24 | 2019-04-10 | Basf Se | Viscosity breaking process for propylene polymers |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5148196A (ja) * | 1974-10-23 | 1976-04-24 | Hitachi Cable | Keeburutanmatsubu |
-
1972
- 1972-07-25 AT AT636872A patent/AT319589B/de not_active IP Right Cessation
-
1973
- 1973-06-20 DE DE2331354A patent/DE2331354B2/de not_active Withdrawn
- 1973-07-12 GB GB3338473A patent/GB1442681A/en not_active Expired
- 1973-07-16 ZA ZA734828A patent/ZA734828B/xx unknown
- 1973-07-16 IE IE1191/73A patent/IE38160B1/xx unknown
- 1973-07-20 SE SE7310163A patent/SE410970B/xx unknown
- 1973-07-24 CS CS5305A patent/CS174891B2/cs unknown
- 1973-07-25 JP JP48083221A patent/JPS5219595B2/ja not_active Expired
- 1973-07-25 NL NL7310346.A patent/NL161468C/xx not_active IP Right Cessation
- 1973-10-29 BE BE137194A patent/BE806669A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3742845A1 (de) * | 1987-12-17 | 1989-07-13 | Lentia Gmbh | Verfahren zur herstellung von faserverstaerkten polypropylenbahnen sowie faserverstaerkte polypropylenbahnen |
| DE3742845C2 (de) * | 1987-12-17 | 1996-07-11 | Danubia Petrochem Deutschland | Verfahren zur Herstellung von faserverstärkten Polypropylenbahnen sowie faserverstärkte Polypropylenbahnen |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA734828B (en) | 1974-06-26 |
| IE38160B1 (en) | 1978-01-04 |
| BE806669A (fr) | 1974-04-29 |
| JPS5219595B2 (enrdf_load_html_response) | 1977-05-28 |
| SE410970B (sv) | 1979-11-19 |
| AT319589B (de) | 1974-12-27 |
| NL7310346A (enrdf_load_html_response) | 1974-01-29 |
| CS174891B2 (enrdf_load_html_response) | 1977-04-29 |
| NL161468C (nl) | 1980-02-15 |
| NL161468B (nl) | 1979-09-17 |
| IE38160L (en) | 1974-01-25 |
| GB1442681A (en) | 1976-07-14 |
| JPS4959861A (enrdf_load_html_response) | 1974-06-11 |
| DE2331354A1 (de) | 1974-02-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8230 | Patent withdrawn |