CH433751A - Verfahren zur Herstellung von neuen hochmolekularen Polymeren - Google Patents

Verfahren zur Herstellung von neuen hochmolekularen Polymeren

Info

Publication number: CH433751A
Authority: CH; Switzerland
Prior art keywords: ketene; aldehyde; alkyl; aryl; molecular weight
Prior art date: 1961-04-27

Application number

CH503762A

Other languages

German (de)

English (en)

Inventor

Natta Giulio

Mazzanti Giorgio

Pregaglia Gianfranco

Pozzi Giancarlo

Original Assignee

Montedison Spa

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.)

1961-04-27

Filing date

1962-04-26

Publication date

1967-04-15

1962-04-26 Application filed by Montedison Spa filed Critical Montedison Spa

1967-04-15 Publication of CH433751A publication Critical patent/CH433751A/de

Links

238000000034 method Methods 0.000 title claims description 20
238000004519 manufacturing process Methods 0.000 title claims description 7
229920006158 high molecular weight polymer Polymers 0.000 title description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 34
229920000642 polymer Polymers 0.000 claims description 30
150000001299 aldehydes Chemical class 0.000 claims description 24
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 20
VDOKWPVSGXHSNP-UHFFFAOYSA-N 2-methylprop-1-en-1-one Chemical compound CC(C)=C=O VDOKWPVSGXHSNP-UHFFFAOYSA-N 0.000 claims description 19
239000000178 monomer Substances 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 16
239000003054 catalyst Substances 0.000 claims description 15
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 claims description 13
125000003118 aryl group Chemical group 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 10
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 6
125000000623 heterocyclic group Chemical group 0.000 claims description 6
-1 lithium hydrides Chemical class 0.000 claims description 5
125000003107 substituted aryl group Chemical group 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
150000004678 hydrides Chemical class 0.000 claims description 4
229910052744 lithium Inorganic materials 0.000 claims description 4
AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 claims description 3
229910010084 LiAlH4 Inorganic materials 0.000 claims description 3
150000004703 alkoxides Chemical class 0.000 claims description 3
150000001408 amides Chemical class 0.000 claims description 3
239000012280 lithium aluminium hydride Substances 0.000 claims description 3
ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
125000002877 alkyl aryl group Chemical group 0.000 claims 1
150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
239000012442 inert solvent Substances 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 50
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
238000006243 chemical reaction Methods 0.000 description 15
229920001577 copolymer Polymers 0.000 description 15
239000000047 product Substances 0.000 description 15
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
238000009835 boiling Methods 0.000 description 13
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
238000002441 X-ray diffraction Methods 0.000 description 10
229920000728 polyester Polymers 0.000 description 10
150000002561 ketenes Chemical class 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
238000000605 extraction Methods 0.000 description 8
238000007334 copolymerization reaction Methods 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
229920002521 macromolecule Polymers 0.000 description 5
238000006116 polymerization reaction Methods 0.000 description 5
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
229920005603 alternating copolymer Polymers 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
239000000284 extract Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000012259 ether extract Substances 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
150000002596 lactones Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000012648 alternating copolymerization Methods 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000001816 cooling Methods 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
FONOSWYYBCBQGN-UHFFFAOYSA-N ethylene dione Chemical class O=C=C=O FONOSWYYBCBQGN-UHFFFAOYSA-N 0.000 description 2
238000005194 fractionation Methods 0.000 description 2
239000000155 melt Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
229910010082 LiAlH Inorganic materials 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001339 alkali metal compounds Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000000732 arylene group Chemical group 0.000 description 1
GSCLMSFRWBPUSK-UHFFFAOYSA-N beta-Butyrolactone Chemical compound CC1CC(=O)O1 GSCLMSFRWBPUSK-UHFFFAOYSA-N 0.000 description 1
125000003180 beta-lactone group Chemical group 0.000 description 1
VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 1
RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 1
RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
125000002587 enol group Chemical group 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000002360 explosive Substances 0.000 description 1
239000000835 fiber Substances 0.000 description 1
238000000265 homogenisation Methods 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
LTRVAZKHJRYLRJ-UHFFFAOYSA-N lithium;butan-1-olate Chemical compound [Li+].CCCC[O-] LTRVAZKHJRYLRJ-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
239000000203 mixture Substances 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000001294 propane Substances 0.000 description 1
229960000380 propiolactone Drugs 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000004753 textile Substances 0.000 description 1
238000007669 thermal treatment Methods 0.000 description 1
HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 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
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/06—Catalysts
- 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
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/18—Copolymerisation of aldehydes or ketones
- C08G2/20—Copolymerisation of aldehydes or ketones with other aldehydes or ketones
- 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
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/18—Copolymerisation of aldehydes or ketones
- C08G2/26—Copolymerisation of aldehydes or ketones with compounds containing carbon-to-carbon unsaturation

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)
Phenolic Resins Or Amino Resins (AREA)

CH503762A 1961-04-27 1962-04-26 Verfahren zur Herstellung von neuen hochmolekularen Polymeren CH433751A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT772161		1961-04-27

Publications (1)

Publication Number	Publication Date
CH433751A true CH433751A (de)	1967-04-15

Family

ID=11125282

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH503762A CH433751A (de)	1961-04-27	1962-04-26	Verfahren zur Herstellung von neuen hochmolekularen Polymeren

Country Status (4)

Country	Link
CH (1)	CH433751A (es)
DK (1)	DK106522C (es)
ES (1)	ES276807A1 (es)
GB (1)	GB950508A (es)

1962
- 1962-03-12 GB GB941162A patent/GB950508A/en not_active Expired
- 1962-04-26 DK DK189362A patent/DK106522C/da active
- 1962-04-26 ES ES276807A patent/ES276807A1/es not_active Expired
- 1962-04-26 CH CH503762A patent/CH433751A/de unknown

Also Published As

Publication number	Publication date
ES276807A1 (es)	1962-10-16
GB950508A (en)	1964-02-26
DK106522C (da)	1967-02-13

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