DE3247277C2 - Verfahren zur Herstellung von Block-Copolymeren auf der Basis von Pivalolacton - Google Patents

Verfahren zur Herstellung von Block-Copolymeren auf der Basis von Pivalolacton

Info

Publication number: DE3247277C2
Authority: DE; Germany
Prior art keywords: block; temperature; methylstyrene; diene; pivalolactone
Prior art date: 1981-12-22
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

DE3247277A

Other languages

German (de)

English (en)

Other versions

DE3247277A1 (de

Inventor

Mario San Donato Milanese Mailand/Milano Bruzzone

Luciano Gargani

Arnaldo Roggero

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.)

ENOXY CHIMICA SpA SASSARI IT

Original Assignee

ENOXY CHIMICA SpA SASSARI IT

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.)

1981-12-22

Filing date

1982-12-21

Publication date

1986-09-04

1982-12-21 Application filed by ENOXY CHIMICA SpA SASSARI IT filed Critical ENOXY CHIMICA SpA SASSARI IT

1983-06-30 Publication of DE3247277A1 publication Critical patent/DE3247277A1/de

1986-09-04 Application granted granted Critical

1986-09-04 Publication of DE3247277C2 publication Critical patent/DE3247277C2/de

Status Expired legal-status Critical Current

Links

ULKFLOVGORAZDI-UHFFFAOYSA-N 3,3-dimethyloxetan-2-one Chemical compound CC1(C)COC1=O ULKFLOVGORAZDI-UHFFFAOYSA-N 0.000 title claims abstract description 21
229920001400 block copolymer Polymers 0.000 title claims abstract description 5
238000000034 method Methods 0.000 title claims description 9
230000008569 process Effects 0.000 title claims description 5
238000004519 manufacturing process Methods 0.000 title description 5
150000001993 dienes Chemical class 0.000 claims abstract description 15
238000006116 polymerization reaction Methods 0.000 claims description 14
230000007704 transition Effects 0.000 claims description 12
230000015572 biosynthetic process Effects 0.000 claims description 3
JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 2
125000002897 diene group Chemical group 0.000 claims description 2
230000000379 polymerizing effect Effects 0.000 claims 2
229920000642 polymer Polymers 0.000 abstract description 26
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 abstract description 10
XIRPMPKSZHNMST-UHFFFAOYSA-N 1-ethenyl-2-phenylbenzene Chemical group C=CC1=CC=CC=C1C1=CC=CC=C1 XIRPMPKSZHNMST-UHFFFAOYSA-N 0.000 abstract 1
KLFWUSCMFSYYOJ-UHFFFAOYSA-N 1-phenyl-2-prop-1-en-2-ylbenzene Chemical group CC(=C)C1=CC=CC=C1C1=CC=CC=C1 KLFWUSCMFSYYOJ-UHFFFAOYSA-N 0.000 abstract 1
LCJNYCWJKAWZKZ-UHFFFAOYSA-N 1-prop-1-en-2-ylnaphthalene Chemical compound C1=CC=C2C(C(=C)C)=CC=CC2=C1 LCJNYCWJKAWZKZ-UHFFFAOYSA-N 0.000 abstract 1
IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 abstract 1
KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 19
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 10
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
125000001931 aliphatic group Chemical group 0.000 description 6
239000002904 solvent Substances 0.000 description 6
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 4
-1 cycloaliphatic Chemical group 0.000 description 4
238000010790 dilution Methods 0.000 description 4
239000012895 dilution Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000000178 monomer Substances 0.000 description 3
229920002857 polybutadiene Polymers 0.000 description 3
229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 3
PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
239000005062 Polybutadiene Substances 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000012190 activator Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000001816 cooling Methods 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
238000010586 diagram Methods 0.000 description 2
238000004455 differential thermal analysis Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
239000003999 initiator Substances 0.000 description 2
238000005259 measurement Methods 0.000 description 2
239000012454 non-polar solvent Substances 0.000 description 2
PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
BOGRNZQRTNVZCZ-AATRIKPKSA-N (3e)-3-methylpenta-1,3-diene Chemical compound C\C=C(/C)C=C BOGRNZQRTNVZCZ-AATRIKPKSA-N 0.000 description 1
AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 1
BOGRNZQRTNVZCZ-UHFFFAOYSA-N 1,2-dimethyl-butadiene Natural products CC=C(C)C=C BOGRNZQRTNVZCZ-UHFFFAOYSA-N 0.000 description 1
KUFLEYZWYCAZCC-UHFFFAOYSA-N 2-methylhexa-1,3-diene Chemical compound CCC=CC(C)=C KUFLEYZWYCAZCC-UHFFFAOYSA-N 0.000 description 1
UGWOAPBVIGCNOV-UHFFFAOYSA-N 5-ethenyldec-5-ene Chemical compound CCCCC=C(C=C)CCCC UGWOAPBVIGCNOV-UHFFFAOYSA-N 0.000 description 1
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
FACXGONDLDSNOE-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 FACXGONDLDSNOE-UHFFFAOYSA-N 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
230000021523 carboxylation Effects 0.000 description 1
238000006473 carboxylation reaction Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
230000003750 conditioning effect Effects 0.000 description 1
238000009826 distribution Methods 0.000 description 1
238000012676 equilibrium polymerization Methods 0.000 description 1
BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
238000007306 functionalization reaction Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000006872 improvement Effects 0.000 description 1
230000003993 interaction Effects 0.000 description 1
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000006082 mold release agent Substances 0.000 description 1
238000000465 moulding Methods 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001195 polyisoprene Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000003825 pressing Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
ONQCKWIDZTZEJA-UHFFFAOYSA-N sodium;pentane Chemical compound [Na+].CCCC[CH2-] ONQCKWIDZTZEJA-UHFFFAOYSA-N 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000005207 tetraalkylammonium group Chemical group 0.000 description 1
150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
238000002076 thermal analysis method Methods 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000002699 waste material Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- 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
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/10—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated with vinyl-aromatic monomers

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Compositions Of Macromolecular Compounds (AREA)
Polymerization Catalysts (AREA)
Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)

DE3247277A 1981-12-22 1982-12-21 Verfahren zur Herstellung von Block-Copolymeren auf der Basis von Pivalolacton Expired DE3247277C2 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT25754/81A IT1196420B (it)	1981-12-22	1981-12-22	Copolimeri a blocchi a base di pivalolattone e processo per la loro preparazione

Publications (2)

Publication Number	Publication Date
DE3247277A1 DE3247277A1 (de)	1983-06-30
DE3247277C2 true DE3247277C2 (de)	1986-09-04

Family

ID=11217638

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE3247277A Expired DE3247277C2 (de)	1981-12-22	1982-12-21	Verfahren zur Herstellung von Block-Copolymeren auf der Basis von Pivalolacton

Country Status (13)

Country	Link
JP (1)	JPS58111816A (fr)
KR (1)	KR840002858A (fr)
AU (1)	AU9167182A (fr)
BE (1)	BE895447A (fr)
BR (1)	BR8207524A (fr)
CA (1)	CA1203336A (fr)
DE (1)	DE3247277C2 (fr)
ES (1)	ES8402599A1 (fr)
FR (1)	FR2522668B1 (fr)
GB (1)	GB2112002B (fr)
IT (1)	IT1196420B (fr)
NL (1)	NL8204908A (fr)
ZA (1)	ZA829300B (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1194408B (it) *	1983-09-28	1988-09-22	Anic Spa	Processo per la sintesi di copolimeri a blocchi a base di pivalolattone
GB8333697D0 (en) *	1983-12-17	1984-01-25	Exxon Research Engineering Co	Hydrocarbon resins
US4674030A (en) *	1984-01-24	1987-06-16	Bijur Lubricating Corp.	Lubricating system control circuit
JP2617908B2 (ja) *	1984-09-27	1997-06-11	松下電器産業株式会社	投写光学装置
JPH0627895B2 (ja) *	1984-12-20	1994-04-13	松下電器産業株式会社	投写レンズ
JPH0627896B2 (ja) *	1985-02-06	1994-04-13	松下電器産業株式会社	投写レンズ
JPH065322B2 (ja) *	1988-03-23	1994-01-19	呉羽化学工業株式会社	光学材料の製造方法
US5015695A (en) *	1989-05-09	1991-05-14	Shell Oil Company	Functionalized elastomeric polymer production
US4978719A (en) *	1989-05-09	1990-12-18	Shell Oil Company	Functionalized elastomeric polymers
JP2999250B2 (ja) *	1990-11-30	2000-01-17	呉羽化学工業株式会社	新規なグラフト共重合体

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3557252A (en) *	1969-01-17	1971-01-19	Phillips Petroleum Co	Poly(vinyl halide) compositions
US3557255A (en) *	1969-03-21	1971-01-19	Du Pont	Pivalolactone-diene block copolymers and their preparation
US4034021A (en) *	1973-11-06	1977-07-05	E. I. Du Pont De Nemours And Company	Copolymers of pivalolactone and isoprene or butadiene

1981
- 1981-12-22 IT IT25754/81A patent/IT1196420B/it active
1982
- 1982-12-17 ZA ZA829300A patent/ZA829300B/xx unknown
- 1982-12-20 NL NL8204908A patent/NL8204908A/nl not_active Application Discontinuation
- 1982-12-20 AU AU91671/82A patent/AU9167182A/en not_active Abandoned
- 1982-12-20 GB GB08236144A patent/GB2112002B/en not_active Expired
- 1982-12-21 BR BR8207524A patent/BR8207524A/pt unknown
- 1982-12-21 CA CA000418175A patent/CA1203336A/fr not_active Expired
- 1982-12-21 FR FR8221465A patent/FR2522668B1/fr not_active Expired
- 1982-12-21 DE DE3247277A patent/DE3247277C2/de not_active Expired
- 1982-12-22 JP JP57225778A patent/JPS58111816A/ja active Pending
- 1982-12-22 ES ES518856A patent/ES8402599A1/es not_active Expired
- 1982-12-22 BE BE0/209790A patent/BE895447A/fr not_active IP Right Cessation
- 1982-12-24 KR KR1019820005810A patent/KR840002858A/ko not_active Ceased

Also Published As

Publication number	Publication date
ES518856A0 (es)	1984-02-01
DE3247277A1 (de)	1983-06-30
GB2112002A (en)	1983-07-13
FR2522668B1 (fr)	1986-11-21
IT1196420B (it)	1988-11-16
BR8207524A (pt)	1983-10-25
GB2112002B (en)	1986-03-05
NL8204908A (nl)	1983-07-18
KR840002858A (ko)	1984-07-21
AU9167182A (en)	1983-06-30
IT8125754A0 (it)	1981-12-22
BE895447A (fr)	1983-06-22
JPS58111816A (ja)	1983-07-04
ZA829300B (en)	1983-11-30
ES8402599A1 (es)	1984-02-01
CA1203336A (fr)	1986-04-15
FR2522668A1 (fr)	1983-09-09

Legal Events

Date	Code	Title
1983-06-30	OP8	Request for examination as to paragraph 44 patent law
1986-09-04	D2	Grant after examination
1987-03-05	8364	No opposition during term of opposition
1987-12-17	8339	Ceased/non-payment of the annual fee

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DE69121376T2 (de)	1996-12-19	Styrolbutadienblockcopolymerisate mit Endblöcken von kontinuierlich sich ändernder Zusammensetzung
DE69312737T2 (de)	1997-12-04	Verfahren zur herstellung von polydimethylblockcopolymeren
DE3247277C2 (de)	1986-09-04	Verfahren zur Herstellung von Block-Copolymeren auf der Basis von Pivalolacton
DE1745225B2 (de)	1977-08-18	Verfahren zur herstellung von block- copolymerisaten
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DE1645332B2 (de)	1978-07-06	Verfahren zur Herstellung von polymeren Massen durch Kuppeln
EP0904307B1 (fr)	2000-06-28	Procede de fabrication de copolymeres sequences ab hydrophobes-hydrophiles
DE69121769T2 (de)	1997-02-20	Verfahren zur Herstellung von transparentem schlagfestem Styrolharz
DE69706759T2 (de)	2002-07-04	Verfahren zur Herstellung von ABS Harzen
DE1745261A1 (de)	1971-09-02	Verfahren zur Herstellung von Blockcopolymeren
DE3444028C2 (fr)	1987-06-11
EP0020924B1 (fr)	1982-05-12	Procédé d'isomérisation de doubles liaisons isolées en doubles liaisons conjuguées dans des homo- et/ou copolymères de 1,3-diènes
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