DE1027401B - Process for the production of polymers or copolymers - Google Patents
Process for the production of polymers or copolymersInfo
- Publication number
- DE1027401B DE1027401B DER18814A DER0018814A DE1027401B DE 1027401 B DE1027401 B DE 1027401B DE R18814 A DER18814 A DE R18814A DE R0018814 A DER0018814 A DE R0018814A DE 1027401 B DE1027401 B DE 1027401B
- Authority
- DE
- Germany
- Prior art keywords
- polymer
- ammonia
- dissolved
- polymerized
- ecm
- 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
- 229920000642 polymer Polymers 0.000 title claims description 17
- 229920001577 copolymer Polymers 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- -1 aliphatic radical Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 3
- 125000002091 cationic group Chemical group 0.000 claims description 3
- 238000004132 cross linking Methods 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 4
- 239000000243 solution Substances 0.000 claims 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 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 claims 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims 1
- 229910015900 BF3 Inorganic materials 0.000 claims 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims 1
- 239000005662 Paraffin oil Substances 0.000 claims 1
- 239000004793 Polystyrene Substances 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims 1
- 229910001628 calcium chloride Inorganic materials 0.000 claims 1
- 239000001110 calcium chloride Substances 0.000 claims 1
- 239000003518 caustics Substances 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- 239000006185 dispersion Substances 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229920002223 polystyrene Polymers 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 7
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 6
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/40—Esters of unsaturated alcohols, e.g. allyl (meth)acrylate
-
- 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
- C08F16/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F16/12—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
-
- 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
- C08F16/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F16/12—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
- C08F16/14—Monomers containing only one unsaturated aliphatic radical
- C08F16/26—Monomers containing oxygen atoms in addition to the ether oxygen
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)
Description
BIBLIOTHEKLIBRARY
DES DEUTSCHENOF THE GERMAN
PATEHTASITESPATEHTASITES
Die Polymerisation von Verbindungen der allgemeinen FormelThe polymerization of compounds of the general formula
R1 R 1
H8C = CH-H 8 C = CH-
.0-R-OCO-C = CH-R2 .0-R-OCO-C = CH-R 2
liei der die Vinyläthergruppe als polymerisations- oder andersartig reaktionsfähige Gruppe erhalten bleibt, ist bisher nicht bekannt und erschien im Hinblick auf die Labilität der Vinoxygruppe nicht durchführbar. Mit dieser Ansicht stimmen die Aussagen von Η. Haas und M. Simon, Journal of Polymer Science, 1955, Bd. XVII, S. 424 überein, daß /S-Vinoxyäthylmethacrylat zwar zweistufig derart polymerisiert werden kann, daß in erster Stufe die Vinyläthergruppe kationisch und das erhaltene Polymerisat in zweiter Stufe radikalisch polymerisiert werden kann, daß jedoch eine anionische Polymerisation der Methacryldoppelbindung unter Erhalt der Vinylgruppe nicht durchführbar sei.liei of the vinyl ether group as polymerization or otherwise reactive group is retained is not previously known and appeared in view of the Vinoxy group lability not feasible. With this view, the statements of Η are correct. Haas and M. Simon, Journal of Polymer Science, 1955, Vol. XVII, p. 424 that / S-vinoxyethyl methacrylate Although it can be polymerized in two stages in such a way that the vinyl ether group in the first stage cationic and the polymer obtained can be polymerized by free radicals in the second stage, but that an anionic polymerization of the methacrylic double bond with retention of the vinyl group does not is feasible.
Entgegen dieser Ansicht lassen sich Verbindungen, die der genannten allgemeinen Formel entsprechen, unter Erhalt der Vinyläthergruppe anionisch polymerisieren. In der genannten Formel bedeuten R einen mindestens 2 C-Atome aufweisenden zweiwertigen aliphatischen, gegebenenfalls Heteroatome enthaltenden Rest, R1 Wasserstoff oder einen Alkylrest und R2 Wasserstoff, einen Alkyl- oder einen Arylrest. Bestimmte Stoffe, insbesondere solche mit einer freien Hydroxylgruppe, z. B. Glykolmonovinyläther, hemmen den Ablauf der anionischen Polymerisation in flüssigem Ammoniak. Für ihre Abwesenheit ist deshalb Sorge zu tragen. — Als einfacher Vertreter der im Sinne des vorliegenden Verfahrens zweistufig polymerisierbaren monomeren Verbindung sei das Vinylglykolmethacrylat genannt. Unter der Einwirkung von metallischem Kalium in flüssigem Ammoniak bei —· 35° C polymerisiert das Monomere zu einem weißen Pulver, das in organischen Lösungsmitteln löslich ist. Löst man das erhaltene Polymethacrylat in Methacrylsäuremethylester und setzt Benzoylperoxyd zu, so erhält man stark vernetzte unlösliche, gegebenenfalls auch unquellbare Mischpolymerisate.Contrary to this view, compounds which correspond to the general formula mentioned can be polymerized anionically with retention of the vinyl ether group. In the formula mentioned, R is a divalent aliphatic radical containing at least 2 carbon atoms, optionally containing heteroatoms, R 1 is hydrogen or an alkyl radical and R 2 is hydrogen, an alkyl or an aryl radical. Certain substances, especially those with a free hydroxyl group, e.g. B. Glykolmonovinyläther, inhibit the progress of the anionic polymerization in liquid ammonia. Care must therefore be taken to ensure that they are absent. - Vinyl glycol methacrylate may be mentioned as a simple representative of the monomeric compound polymerizable in two stages in the context of the present process. Under the action of metallic potassium in liquid ammonia at -35 ° C, the monomer polymerizes to a white powder that is soluble in organic solvents. If the polymethacrylate obtained is dissolved in methyl methacrylate and benzoyl peroxide is added, strongly crosslinked, insoluble, possibly also non-swellable copolymers are obtained.
Die in der anionisch angeregten Polymerisationsstufe erhaltenen löslichen Produkte können wie folgt verwendet werden: Die gleichzeitig ein Polymerisat und eine polymerisierbare Verbindung darstellenden Produkte können unter dem Einfluß radikalischer oder kationischer Beschleuniger polymerisiert bzw. mischpolymerisiert und in wertvolle Endprodukte übergeführt werden. Für die Weiterverarbeitung der erhaltenen Zwischenprodukte sei beispielsweise ihre Mischpolymerisation mit ungesättigten Polyestern und anderen Monomeren zu Polyesterharzen genannt.The soluble products obtained in the anionically excited polymerization stage can be as follows can be used: Those which represent a polymer and a polymerizable compound at the same time Products can be polymerized or copolymerized under the influence of free radical or cationic accelerators and converted into valuable end products. For further processing of the received Intermediate products are, for example, their copolymerization with unsaturated polyesters and other monomers to polyester resins.
Verfahren zum Herstellen von
Polymerisaten bzw. MischpolymerisatenMethod of making
Polymers or copolymers
Anmelder:Applicant:
Röhm & Haas G. m. b. H.,
Darmstadt, Mainzer Str. 42Röhm & Haas G. mb H.,
Darmstadt, Mainzer Str. 42
Herbert Schreiber, Darmstadt,
ist als Erfinder genannt wordenHerbert Schreiber, Darmstadt,
has been named as the inventor
Die dichte Vernetzung solcher Produkte führt zu harten, in Lösungsmitteln unlöslichen und unquellbaren Produkten, die z. B. als Dentalkunststoffe Verwendung finden können. Durch Bemessung des Mengenverhältnisses zwischen eimern die polymerisationsfähige Vinyläthergruppe aufweisenden Polymerisat einerseits und einer weiteren mischpolymerisierbaren Verbindung andererseits lassen sich Produkte erhalten, deren Vernetzungsgrad und damit deren mechanische Festigkeit willkürlich eingestellt werden können. Die zusätzliche Möglichkeit, die monomere, der genannten Formel entsprechende Verbindung mit anderen anionisch polymerisierenden Monomeren zu mischpolymerisieren, eröffnet weitere Möglichkeiten für die Herstellung neuer polymerisations- und reaktionsfähiger Verbindungen.The dense cross-linking of such products leads to hard, solvent-insoluble and non-swellable products Products that z. B. can be used as dental plastics. By dimensioning the Quantity ratio between buckets of the polymerizable Polymer containing vinyl ether groups on the one hand and a further copolymerizable polymer Compound on the other hand, products can be obtained, their degree of crosslinking and thus whose mechanical strength can be adjusted arbitrarily. The additional option of using the monomeric, compound corresponding to the formula mentioned with other anionically polymerizing monomers to copolymerize, opens up further possibilities for the production of new polymerization and reactive compounds.
Es sei darauf hingewiesen, daß der zweite PoIymerisationsschritt nicht nur radikalisch, sondern auch kationisch katalysiert werden kann — eine Möglichkeit, die in besonderen Fällen von Vorteil sein mag.It should be noted that the second polymerization step can be catalyzed not only radically, but also cationically - a possibility which may be advantageous in special cases.
Die nachstehenden Beispiele erschöpfen die gegebenen Möglichkeiten bei weitem nicht. Als erfinderisch wird allgemein ein Verfahren geltend gemacht, bei dem Verbindungen des angegebenen Formeltyps, die also sowohl eine Vinyläthergruppe als auch eine gegebenenfalls substituierte Acrylgruppe enthalten, in erster Stufe unter dem Einfluß anionischer Beschleuniger ohne Veränderung der Vinyläthergruppe polymerisiert und die erhaltenen Produkte, gegebenenfalls durch eine radikalisch oder kationisch ausgelöste Polymerisation bzw. Mischpolymerisation in hochwertige Kunststoffe übergeführt werden.The following examples by no means exhaust the options available. As inventive a procedure is generally asserted in which compounds of the specified formula type, i.e. the contain both a vinyl ether group and an optionally substituted acrylic group, in the first place Stage polymerized under the influence of anionic accelerators without changing the vinyl ether group and the products obtained, optionally by a free-radically or cationically initiated polymerization or mixed polymerisation can be converted into high-quality plastics.
1. In einer gegen Luftfeuchtigkeit abgeschlossenen Apparatur, die mit Rührer, Thermometer, Zuiauf- und Absaugrohr fürAmmoniak ausgestattet ist, wer-1. In an apparatus which is sealed against humidity and which is equipped with a stirrer, thermometer, and a suction tube for ammonia,
709 958/443709 958/443
Claims (2)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DER18814A DE1027401B (en) | 1956-05-02 | 1956-05-02 | Process for the production of polymers or copolymers |
FR1174734D FR1174734A (en) | 1956-05-02 | 1957-04-30 | Process for the preparation of polymeric compounds containing groups suitable for polymerization, and optionally crosslinked plastics |
GB1405657A GB836046A (en) | 1956-05-02 | 1957-05-02 | New polymers |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DER18814A DE1027401B (en) | 1956-05-02 | 1956-05-02 | Process for the production of polymers or copolymers |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1027401B true DE1027401B (en) | 1958-04-03 |
Family
ID=7400292
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DER18814A Pending DE1027401B (en) | 1956-05-02 | 1956-05-02 | Process for the production of polymers or copolymers |
Country Status (3)
Country | Link |
---|---|
DE (1) | DE1027401B (en) |
FR (1) | FR1174734A (en) |
GB (1) | GB836046A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0646580A3 (en) * | 1993-09-16 | 1995-10-11 | Ciba Geigy Ag | Vinylether compounds with additional functional groups differing from vinylether and their use in the formulation of curable compositions. |
US7321051B2 (en) | 2000-10-23 | 2008-01-22 | Nippon Shokubai Co., Ltd. | Composition of vinyl ether group-containing (meth) acrylic ester and production method thereof |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3383374A (en) * | 1960-10-31 | 1968-05-14 | Union Carbide Corp | Ethylenically unsaturated 1-acyloxyaliphatic ethers and polymers thereof |
DE69942866D1 (en) | 1998-06-25 | 2010-11-25 | Hydro Quebec | Polymers of block copolymerizable monomers and their use in the preparation of ionic conductors |
JP3718518B2 (en) | 2003-10-03 | 2005-11-24 | 日東電工株式会社 | Photorefractive index modulation polymer, photorefractive index modulation polymer composition, and refractive index control method |
-
1956
- 1956-05-02 DE DER18814A patent/DE1027401B/en active Pending
-
1957
- 1957-04-30 FR FR1174734D patent/FR1174734A/en not_active Expired
- 1957-05-02 GB GB1405657A patent/GB836046A/en not_active Expired
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0646580A3 (en) * | 1993-09-16 | 1995-10-11 | Ciba Geigy Ag | Vinylether compounds with additional functional groups differing from vinylether and their use in the formulation of curable compositions. |
US5605941A (en) * | 1993-09-16 | 1997-02-25 | Steinmann; Bettina | Vinyl ether compounds having additional functional groups other than vinyl ether groups and the use thereof in the formulation of curable compositions |
US5705316A (en) * | 1993-09-16 | 1998-01-06 | Ciba Specialty Chemicals Corporation | Vinyl ether compounds having additional functional groups other than vinyl ether groups and the use thereof in the formulation of curable compositions |
US5783712A (en) * | 1993-09-16 | 1998-07-21 | Ciba Specialty Chemicals Corporation | Vinyl ether compounds having additional functional groups other than vinyl ether groups and the use thereof in the formulation of curable compositions |
US5783615A (en) * | 1993-09-16 | 1998-07-21 | Ciba Specialty Chemicals Corporation | Vinyl ether compounds having additional functional groups other than vinyl ether groups and the use thereof in the formulation of curable compositions |
US7321051B2 (en) | 2000-10-23 | 2008-01-22 | Nippon Shokubai Co., Ltd. | Composition of vinyl ether group-containing (meth) acrylic ester and production method thereof |
US7368594B2 (en) | 2000-10-23 | 2008-05-06 | Nippon Shokubai Co., Ltd. | Composition of vinyl ether group containing (meth)acrylic acid ester and production method thereof |
Also Published As
Publication number | Publication date |
---|---|
FR1174734A (en) | 1959-03-16 |
GB836046A (en) | 1960-06-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE1768083C3 (en) | Crosslinkable Polymers and Their Use | |
DE1069874B (en) | Process for the production of mixed polymers | |
DE1027401B (en) | Process for the production of polymers or copolymers | |
DE2334826A1 (en) | NEW ACRYLIC ACID ESTERS CONTAINING AN N, N-HETEROCYCLIC RING, METHODS OF MANUFACTURING AND USING THEM | |
DE2431001A1 (en) | SUBSTITUTED ACRYLAMIDOALKANE SULPHONIC ACID ESTERS, PROCESS FOR THEIR PRODUCTION AND THEIR USE FOR THE PRODUCTION OF POLYMERIZED COMPOUNDS | |
DE2217158A1 (en) | Process for the production of a photopolymer | |
DE69022230T2 (en) | METHOD FOR PRODUCING COPOLYMERS OF MALEINANHYDRIDE AND AN ALKYLVINYL ETHER IN A STERICALLY HIDDEN MONO ETHER SOLVENT. | |
DE1032537B (en) | Process for the production of phosphorus-containing polymers | |
DE1221450B (en) | Process for the production of copolymers of acrylic acid esters | |
DE2166449A1 (en) | MIXTURE OF POLYMERIZABLE COMPOUNDS | |
US2694693A (en) | Process for preparing polymers of vinyl hydroquinone employing azo-bis-isobutyronitrile as catalyst | |
DE2437916A1 (en) | 3-Alkylidene hydantoin homopolymer prepn. - in melt or aq. soln. and use as flame-proofing agent in polyacrylonitrile spinning dopes | |
DE2261080A1 (en) | PROCESS FOR THE PREPARATION OF OXAZOLIDINE AND TETRAHYDRO-1,3-OXAZINE MONOMERS | |
DE1211156B (en) | Process for the production of unsaturated sulfonic acid betaines by reacting a tertiary amine with a sultone | |
DE2252908A1 (en) | 1,2,2,2-TETRACHLORAETHYLESTERS OF ACRYLIC ACID AND ITS DERIVATIVES AND THEIR POLYMERS, THEIR PRODUCTION AND USE | |
EP0008403B1 (en) | Polymers containing primary aliphatic carbon amide groups and/or n-methylol derivatives of the carbon amide groups; their preparation and their use | |
DE931130C (en) | Process for the production of plastics | |
DE1495850A1 (en) | Process for the production of maleic anhydride copolymers | |
DE1102405B (en) | Process for the production of largely thermally stable acrylonitrile polymers with improved colorability compared to basic dyes | |
DE1047427B (en) | Process for the production of thermosetting polymers using maleimide derivatives | |
DE1133133B (en) | Process for the production of linear thermoplastic polycondensates from diorganosilanediols and aromatic dioxy compounds | |
DE1720433B1 (en) | PROCESS FOR THE POLYMERIZATION OF VINYL COMPOUNDS | |
DE2229302A1 (en) | LIGHT SENSITIVE DIMENSIONS | |
DE1070828B (en) | Process for the preparation of polymeric quaternary ammonium compounds | |
DE1411607B2 (en) | PACKING MATERIAL |