DE1301092B - Verfahren zur Epoxydierung von Copolymerisaten aus 1, 3-Diolefinen - Google Patents
Verfahren zur Epoxydierung von Copolymerisaten aus 1, 3-DiolefinenInfo
- Publication number
- DE1301092B DE1301092B DEC35980A DEC0035980A DE1301092B DE 1301092 B DE1301092 B DE 1301092B DE C35980 A DEC35980 A DE C35980A DE C0035980 A DEC0035980 A DE C0035980A DE 1301092 B DE1301092 B DE 1301092B
- Authority
- DE
- Germany
- Prior art keywords
- acid
- epoxidation
- diolefins
- copolymers
- din
- 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
- 238000006735 epoxidation reaction Methods 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 8
- 229920001577 copolymer Polymers 0.000 title claims description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 12
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 8
- 238000007334 copolymerization reaction Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 2
- 238000012360 testing method Methods 0.000 description 10
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 239000003973 paint Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229910010413 TiO 2 Inorganic materials 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- 235000009161 Espostoa lanata Nutrition 0.000 description 2
- 240000001624 Espostoa lanata Species 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 150000000185 1,3-diols Chemical class 0.000 description 1
- PAOHAQSLJSMLAT-UHFFFAOYSA-N 1-butylperoxybutane Chemical compound CCCCOOCCCC PAOHAQSLJSMLAT-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000002528 anti-freeze Effects 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
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- NWJXSVNLQJZDLV-UHFFFAOYSA-N formic acid;hydrogen peroxide Chemical compound OO.OC=O NWJXSVNLQJZDLV-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000010944 pre-mature reactiony Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 239000008149 soap solution Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 238000005303 weighing Methods 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/027—Polycondensates containing more than one epoxy group per molecule obtained by epoxidation of unsaturated precursor, e.g. polymer or monomer
-
- 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
- C08F8/08—Epoxidation
-
- 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
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
-
- 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
- C08F2810/00—Chemical modification of a polymer
- C08F2810/50—Chemical modification of a polymer wherein the polymer is a copolymer and the modification is taking place only on one or more of the monomers present in minority
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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC35980A DE1301092B (de) | 1965-05-28 | 1965-05-28 | Verfahren zur Epoxydierung von Copolymerisaten aus 1, 3-Diolefinen |
| FR62002A FR1480529A (fr) | 1965-05-28 | 1966-05-18 | Procédé de préparation de résines thermodurcissables par époxydation de copolymères d'oléfines |
| BE681775D BE681775A (enrdf_load_stackoverflow) | 1965-05-28 | 1966-05-27 | |
| GB23888/66A GB1140516A (en) | 1965-05-28 | 1966-05-27 | Process for the production of heat-curable resins |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC35980A DE1301092B (de) | 1965-05-28 | 1965-05-28 | Verfahren zur Epoxydierung von Copolymerisaten aus 1, 3-Diolefinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1301092B true DE1301092B (de) | 1969-08-14 |
Family
ID=7022084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC35980A Pending DE1301092B (de) | 1965-05-28 | 1965-05-28 | Verfahren zur Epoxydierung von Copolymerisaten aus 1, 3-Diolefinen |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE681775A (enrdf_load_stackoverflow) |
| DE (1) | DE1301092B (enrdf_load_stackoverflow) |
| GB (1) | GB1140516A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2766196A1 (fr) * | 1997-07-17 | 1999-01-22 | Goodyear Tire & Rubber | Polymere caoutchouteux, procede de preparation de celui-ci et composition a aspect de cuir en comportant application |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7342075B2 (en) * | 2002-10-31 | 2008-03-11 | Basf Corporation | Carbamate functional addition polymers and method for their preparation |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1111399B (de) * | 1960-04-08 | 1961-07-20 | Phoenix Gummiwerke Ag | Verfahren zur Herstellung von Polyepoxyden aus Polymerisaten oder Mischpolymerisaten von Diolefinen |
-
1965
- 1965-05-28 DE DEC35980A patent/DE1301092B/de active Pending
-
1966
- 1966-05-27 GB GB23888/66A patent/GB1140516A/en not_active Expired
- 1966-05-27 BE BE681775D patent/BE681775A/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1111399B (de) * | 1960-04-08 | 1961-07-20 | Phoenix Gummiwerke Ag | Verfahren zur Herstellung von Polyepoxyden aus Polymerisaten oder Mischpolymerisaten von Diolefinen |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2766196A1 (fr) * | 1997-07-17 | 1999-01-22 | Goodyear Tire & Rubber | Polymere caoutchouteux, procede de preparation de celui-ci et composition a aspect de cuir en comportant application |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1140516A (en) | 1969-01-22 |
| BE681775A (enrdf_load_stackoverflow) | 1966-10-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE906998C (de) | Zu harzartigen Produkten haertbare Massen und Verfahren zu ihrer Herstellung | |
| DE2533846B2 (de) | An der Luft härtbare Masse | |
| DE1720701A1 (de) | Vernetzbare Lackharze | |
| US4146519A (en) | Air-drying acrylate lacquer binders | |
| DE2112718B2 (de) | Durch katalysatorzusatz haertbare ueberzugsmassen | |
| DE1669090A1 (de) | UEberzugsmittel auf der Basis veraetherter N-Methylolamid-Gruppen enthaltender Copolymerisate | |
| DE1920496A1 (de) | Verfahren zur Herstellung wasserloeslicher Kunstharze | |
| DE975684C (de) | Verfahren zur Herstellung von Polymerisationsprodukten | |
| EP0005229B1 (de) | Luftvernetzende, eingebaute Holzschutzwirkstoffe enthaltende, Polyacrylat-Lackbindemittel | |
| DE1301092B (de) | Verfahren zur Epoxydierung von Copolymerisaten aus 1, 3-Diolefinen | |
| DE1495801A1 (de) | Verfahren zur Herstellung von Pfropfpolymerisaten des Vinylchlorids | |
| DE1745460B2 (de) | Neue, haertbare ungesaettigte polyamidharzmassen | |
| DE2306808B2 (de) | Copolymere auf Vinylchloridbasis | |
| EP0312733B1 (de) | Verwendung einer wässrigen Emulsion oxidativ trocknender polyethylenglykolmodifizierter Alkydharze als unter Druck stehende Aerosolanstrichzusammensetzung | |
| DE2427847B2 (de) | Thermoplastische Überzugsmischung | |
| DE1922942B2 (de) | Verwendung eines linearen, wärmehärtbaren Copolymerisate zur Oberflächenvergfitung von Holzwerkstoffplatte!! | |
| DE826504C (de) | Verfahren zur Herstellung endpolymerisationsfaehiger Stoffe, welche unter anderem zur Herstellung elektrischer Isolierungen oder in der Elektrotechnik zu verwendender Gegstaende geeignet sind | |
| DE1520406B2 (de) | Verfahren zur herstellung polymerer acetale | |
| DE2345814A1 (de) | Verfahren zur herstellung von styrolacrylsaeure-copolymerisaten und ihre verwendung | |
| DE952201C (de) | Lacke | |
| AT229457B (de) | Verfahren zur Herstellung von Überzügen aus Polyestern der Terephthalsäure | |
| AT220747B (de) | Verfahren zur Herstellung von äthanollöslichen filmbildenden Mischpolymerisaten | |
| DE679943C (de) | Verfahren zur Herstellung von Polymerisationsprodukten organischer Vinylester | |
| DE1245008B (de) | Einbrennlacke | |
| DE1745950A1 (de) | Modifizierte Epoxyester-Harze fuer Schutzueberzuege |