CA1192349A - Polybutylene - Google Patents

Polybutylene

Info

Publication number: CA1192349A
Authority: CA; Canada
Prior art keywords: polybutylene; elastomeric; isotactic; butene; polymers
Prior art date: 1982-04-19
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.): Expired

Application number

CA000422652A

Other languages

English (en)

Inventor

Thair L. Higgins

Georges B. Klingensmith

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Shell USA Inc

Original Assignee

Shell Oil Co

Priority date (The priority date 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 date listed.)

1982-04-19

Filing date

1983-03-01

Publication date

1985-08-20

1983-03-01 Application filed by Shell Oil Co filed Critical Shell Oil Co

1985-08-20 Application granted granted Critical

1985-08-20 Publication of CA1192349A publication Critical patent/CA1192349A/fr

Status Expired legal-status Critical Current

Links

-1 Polybutylene Polymers 0.000 title claims abstract description 106
229920001748 polybutylene Polymers 0.000 title abstract description 91
229920000642 polymer Polymers 0.000 claims abstract description 60
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 51
239000012967 coordination catalyst Substances 0.000 claims description 9
239000010936 titanium Substances 0.000 claims description 9
238000010992 reflux Methods 0.000 claims description 5
229910052719 titanium Inorganic materials 0.000 claims description 3
238000006116 polymerization reaction Methods 0.000 abstract description 23
229920000915 polyvinyl chloride Polymers 0.000 abstract description 16
239000004800 polyvinyl chloride Substances 0.000 abstract description 15
229920001971 elastomer Polymers 0.000 abstract description 11
229920002725 thermoplastic elastomer Polymers 0.000 abstract description 7
239000004014 plasticizer Substances 0.000 abstract description 6
229920002554 vinyl polymer Polymers 0.000 abstract description 5
239000000945 filler Substances 0.000 abstract description 4
239000004606 Fillers/Extenders Substances 0.000 abstract description 3
239000005060 rubber Substances 0.000 abstract description 2
239000003054 catalyst Substances 0.000 description 48
239000000047 product Substances 0.000 description 37
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 33
238000000034 method Methods 0.000 description 23
239000000306 component Substances 0.000 description 18
238000004519 manufacturing process Methods 0.000 description 17
239000000203 mixture Substances 0.000 description 16
229920000098 polyolefin Polymers 0.000 description 13
230000035882 stress Effects 0.000 description 11
239000000806 elastomer Substances 0.000 description 9
239000007787 solid Substances 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 8
238000000605 extraction Methods 0.000 description 8
239000000126 substance Substances 0.000 description 8
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 8
229920001169 thermoplastic Polymers 0.000 description 8
239000004416 thermosoftening plastic Substances 0.000 description 8
239000004743 Polypropylene Substances 0.000 description 7
229920001155 polypropylene Polymers 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 6
239000013078 crystal Substances 0.000 description 6
239000012632 extractable Substances 0.000 description 6
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 5
229910010061 TiC13 Inorganic materials 0.000 description 5
229910052782 aluminium Inorganic materials 0.000 description 5
229920001400 block copolymer Polymers 0.000 description 5
238000013016 damping Methods 0.000 description 5
230000000694 effects Effects 0.000 description 5
230000000704 physical effect Effects 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
238000002441 X-ray diffraction Methods 0.000 description 4
238000009835 boiling Methods 0.000 description 4
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
229920001577 copolymer Polymers 0.000 description 4
230000007547 defect Effects 0.000 description 4
MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000000178 monomer Substances 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
244000043261 Hevea brasiliensis Species 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
229920012485 Plasticized Polyvinyl chloride Polymers 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
238000000748 compression moulding Methods 0.000 description 3
230000000875 corresponding effect Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001640 fractional crystallisation Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
229920001519 homopolymer Polymers 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
229920001580 isotactic polymer Polymers 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229920003052 natural elastomer Polymers 0.000 description 3
229920001194 natural rubber Polymers 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000002002 slurry Substances 0.000 description 3
238000000638 solvent extraction Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
229910052723 transition metal Inorganic materials 0.000 description 3
150000003624 transition metals Chemical class 0.000 description 3
VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
239000004711 α-olefin Substances 0.000 description 3
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
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 2
239000004215 Carbon black (E152) Substances 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
FHUODBDRWMIBQP-UHFFFAOYSA-N Ethyl p-anisate Chemical compound CCOC(=O)C1=CC=C(OC)C=C1 FHUODBDRWMIBQP-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
229910010062 TiCl3 Inorganic materials 0.000 description 2
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
238000006653 Ziegler-Natta catalysis Methods 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
230000008859 change Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003426 co-catalyst Substances 0.000 description 2
239000002131 composite material Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
230000006835 compression Effects 0.000 description 2
238000007906 compression Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000005336 cracking Methods 0.000 description 2
150000001993 dienes Chemical class 0.000 description 2
238000009826 distribution Methods 0.000 description 2
230000009977 dual effect Effects 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
230000036541 health Effects 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
229910001629 magnesium chloride Inorganic materials 0.000 description 2
239000000463 material Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000002674 ointment Substances 0.000 description 2
150000002902 organometallic compounds Chemical class 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
239000004033 plastic Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
230000008569 process Effects 0.000 description 2
210000002966 serum Anatomy 0.000 description 2
HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000011950 stereoregulating catalyst Substances 0.000 description 2
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 2
230000009466 transformation Effects 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
229920002943 EPDM rubber Polymers 0.000 description 1
102100039578 ETS translocation variant 4 Human genes 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
101000813747 Homo sapiens ETS translocation variant 4 Proteins 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
DTAFLBZLAZYRDX-UHFFFAOYSA-N OOOOOO Chemical compound OOOOOO DTAFLBZLAZYRDX-UHFFFAOYSA-N 0.000 description 1
239000008037 PVC plasticizer Substances 0.000 description 1
239000005062 Polybutadiene Substances 0.000 description 1
238000000944 Soxhlet extraction Methods 0.000 description 1
239000004433 Thermoplastic polyurethane Substances 0.000 description 1
229910010066 TiC14 Inorganic materials 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
229910021552 Vanadium(IV) chloride Inorganic materials 0.000 description 1
206010047289 Ventricular extrasystoles Diseases 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
230000009102 absorption Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000009471 action Effects 0.000 description 1
230000032683 aging Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000000498 ball milling Methods 0.000 description 1
BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000001186 cumulative effect Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000007872 degassing Methods 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 1
229920001198 elastomeric copolymer Polymers 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
230000006353 environmental stress Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
235000012438 extruded product Nutrition 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
239000000835 fiber Substances 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
238000010528 free radical solution polymerization reaction Methods 0.000 description 1
238000005227 gel permeation chromatography Methods 0.000 description 1
229920001903 high density polyethylene Polymers 0.000 description 1
239000004700 high-density polyethylene Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000002706 hydrostatic effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000003993 interaction Effects 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000003801 milling Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
239000012184 mineral wax Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
239000008188 pellet Substances 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920002857 polybutadiene Polymers 0.000 description 1
229920001083 polybutene Polymers 0.000 description 1
238000012545 processing Methods 0.000 description 1
238000011027 product recovery Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
230000035939 shock Effects 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000003203 stereoselective catalyst Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
238000012360 testing method Methods 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
229920002803 thermoplastic polyurethane Polymers 0.000 description 1
229920005992 thermoplastic resin Polymers 0.000 description 1
JTJFQBNJBPPZRI-UHFFFAOYSA-J vanadium tetrachloride Chemical compound Cl[V](Cl)(Cl)Cl JTJFQBNJBPPZRI-UHFFFAOYSA-J 0.000 description 1

Landscapes

Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA000422652A 1982-04-19 1983-03-01 Polybutylene Expired CA1192349A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US36938882A	1982-04-19	1982-04-19
US369,388		1982-04-19

Publications (1)

Publication Number	Publication Date
CA1192349A true CA1192349A (fr)	1985-08-20

Family

ID=23455277

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000422652A Expired CA1192349A (fr)	1982-04-19	1983-03-01	Polybutylene

Country Status (1)

Country	Link
CA (1)	CA1192349A (fr)

1983
- 1983-03-01 CA CA000422652A patent/CA1192349A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2002-08-21	MKEC	Expiry (correction)
2003-03-01	MKEX	Expiry

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