Showing papers on "Glycidyl methacrylate published in 1970"

Betaine copolymers with hydroxyalkylacrylates and hydroxyalkylmethacrylates

Abstract: Copolymers of carboxybetaines or sulfobetaines having the formula WHEREIN R1 is hydrogen or methyl; A is oxygen or -NH-; R2 is ethylene, propylene, 2-hydroxypropylene or 2-acetoxypropylene; R3 and R4 are alkyl; n1 is 1 to 4 and X is SO3 or CO2 ; and about 10 to about 95.0 per cent by weight of hydroxyethylacrylate, hydroxyethylmethacrylate, hydroxypropylacrylate, hydroxypropylmethacrylate, polyethylene glycol acrylate, polyethylene glycol methacrylate, polypropylene glycol acrylate, polypropylene glycol methacrylate, polyglycerolacrylate or polyglycerolmethacrylate are disclosed. These neutral, hydrophilic copolymers are useful as binders. This invention relates to selected copolymers comprising units derived from carboxybetaines or sulfobetaines and units derived from hydroxyalkyl acrylates/methacrylates, polyalkylene glycol acrylates/methacrylates or polyglycerol acrylates/methacrylates. More particularly, this invention relates to neutral, hydrophilic copolymers of monomers consisting essentially of about 5.0 to about 90 percent by weight of a carboxybetaine or sulfobetaine having the formula WHEREIN R1 is hydrogen or methyl; A is oxygen or -NH-; R2 is ethylene, propylene, 2-hydroxypropylene or 2-acetoxyproplene; R3 and R4 are alkyl; n1 is 1 to 4 and X is SO3 or CO2 ; and about 10 to about 95.0 per cent by weight of hydroxyethylacrylate, hydroxyethylmethacrylate, hydroxypropylacrylate, hydroxypropylmethacrylate, or a polyalkylene glycol acrylate/methacrylate or polyglycerol acrylate/methacrylate having the formula WHEREIN R'' is hydrogen or methyl, R'''' is hydrogen, methyl or hydroxyl, n2 is zero where R'''' is hydrogen or methyl and 1 where R'''' is hydroxyl, and n3 is 2 to 4. Various carboxybetaines, sulfobetaines, homopolymers and copolymers thereof have been reported in the literature. Thus, U.S. Pat. Nos. 3,473,998 and 3,478,001 disclose sulfobetaines having the formula I and copolymers thereof with acrylonitrile, while U.S. Pat. No. 3,497,482 describes homopolymers of these sulfobetaines and copolymers with certain ethylenically unsaturated monomers. The carboxybetaines having the formula I, homopolymers thereof and copolymers with various ethylenically unsaturated compounds are reported in U.S. Pat. Nos. 2,777,872; 2,935,493 and 2,958,682. Now it has been found that copolymers of carboxybetaines and sulfobetaines with hydroxyalkylacrylates and hydroxyalkylmethacrylates can be provided according to this invention. These copolymers are particularly valuable as hydrophilic bonding agents for glass, leather, plastics, steel, hides and wood. The carboxybetaine and sulfobetaine monomers I can be conveniently prepared by reacting the appropriate Ndialkylaminoalkylacrylate/methacrylate or Ndialkylaminoalkylacrylamide/methacrylamide with a halomonocarboxylic (or sulfonic) acid salt or an alkyl lactone or sultone Following the procedure described in U.S. Pat. No. 2,744,130. Preparation of the copolymers of this invention is effected by polymerizing the carboxybetaine or sulfobetaine I or mixtures thereof, with hydroxyethylacrylate/methacrylate, hydroxypropylacrylate/methacrylate, polyethylene glycol acrylate/methacrylate, polypropylene glycol acrylate/methacrylate, polyglycerol acrylate/methacrylate, or mixtures thereof, the proportion of monomers being within the aforementioned range. The polymerization can be initiated by ultraviolet irradiation, heat, redox systems, peroxides, 2,2''azobis-isobutyronitrile or other suitable means. Preferably, the polymerization is carried out in aqueous or organic solvent solutions at a temperature of from about room temperature to 100* C. Although any of the copolymers can be conveniently prepared, preferred copolymers are those of carboxybetaine or sulfobetaine I wherein R3 and R4 are alkyl having one to four carbon atoms with hydroxyethylacrylate/methacrylate or hydroxypropylacrylate/methacrylate. While not essential to the preparation of the copolymers of this invention, minor amounts, for example up to 10.0 percent by weight of the total monomer charge, of an appropriate crosslinking agent can be utilized. Thus, ethylene glycol dimethacrylate, polyethylene oxide dimethacrylate, N-methylol acrylamide, glycidyl methacrylate, etc. can be suitably employed as crosslinking agents. The copolymers of this invention are useful as hydrophilic binders for a variety of materials, having advantages for these applications over their respective homopolymers and over various copolymers of betaines with other ethylenically unsaturated monomers. Thus, for example, the adhesion of these copolymers to various substrates is better than that of the corresponding polysulfobetaine and polycarboxybetaine homopolymers. These copolymers have increased breaking strength over homopolymers of hydroxyalkylacrylates, thus rendering them highly attractive for use as binders in applications where strength is important, such as in the production of certain non-wovens.

Thermoset molding powders employing glycidyl methacrylate and aromatic amines

Abstract: NOVEL THERMOSETING RESIN POWDERS WHICH CAN BE MOLDED TO FORM PRODUCTS CHARACTERIZED, IN TENSILE MEASUREMENT, BY HIGH ELONGATION-TO-BREAK, HIGH STRENGTH AND MODULUS AND BY A HIGH GLASS TRANSITION TEMPERATURE ARE PREPARED FROM A MIXTURE OF A PREPOLYMER CONSISTING ESSENTIALLY OF GLYCIDYL METHACRYLATE, METHYL METHACRYLATE, AND METHACRYLONITRILE OR ACRYLONITRILE AND AN AMINE CROSSLINKING AGENT.

Radiation‐initiated graft copolymerization of binary monomer mixtures containing acrylonitrile with cotton cellulose

Abstract: By the use of the cobalt 60 postirradiation grafting technique, purified cotton cellulose fibers were graft-copolymerized with binary mixtures of acrylonitrile and other monomers, including styrene, 1,3-butylene dimethacrylate, vinylpyrrolidone, vinylidene chloride, and methyl, butyl, lauryl, glycidyl, and allyl methacrylates. The irradiated cotton fibers were immersed in solutions of the monomers at 25°C to initiate graft copolymerization. Solvents were water, methanol, dimethyl sulfoxide, and methyl ethyl ketone, alone or in several combinations. The extent of graft copolymerization and the composition of the grafted copolymer depended on the composition of the binary mixtures of monomers and on the solvent or mixtures of solvents used. For example, addition of styrene, 1,3-butylene dimethacrylate, or vinylpyrrolidone to acrylonitrile increased the extent of graft copolymerization to a maximum value; addition of vinylidene chloride or allyl methacrylate to acrylonitrile did not greatly affect the extent of graft copolymerization; and addition of methyl or glycidyl methacrylate to acrylonitrile increased the extent of graft copolymerization without passing through a maximum value. The proportion of acrylonitrile in the grafted copolymer was generally less than that in the binary mixtures. As the reaction time was increased, the extent of graft copolymerization increased to a maximum value; however, the composition of the grafted copolymer did not change significantly. Generally, the addition of water to the solutions increased the extent of graft copolymerization. The mechanisms of these graft copolymerization reactions are discussed.

Photographic silver halide light-sensitive element with gelatin subbing layer

Abstract: A photographic element having a subbing layer comprising at least one member selected from the group consisting of (1) a glycidyl methacrylate homopolymer, (2) a glycidyl acrylate homopolymer, (3) a copolymer of glycidyl methacrylate and a copolymerizable vinyl compound, (4) a copolymer of glycidyl acrylate and a copolymerizable vinyl compound which prevents sticking of the photographic element is disclosed.

Polymerizable intermediates containing olefin anhydride copolymer, unsaturated oxirane, and unsaturated anhydride

Abstract: A new liquid composition comprising a polyanhydride, for example, the copolymer of maleic anhydride and an alpha-olefin, an olefinically unsaturated monooxirane compound such as glycidyl methacrylate, an olefinically unsaturated monoanhydride such as maleic anhydride and an olefin such as styrene. The composition is partially cured through the olefinic groups by ionizing gradiation to an intermediate homogeneous composition which is capable of being molded, particularly when in combination with a substrate such as fiber glass, and is further cured through anhydride and epoxide groups to a solid, infusible resin.

Process for the preparation of glycidyl esters

Abstract: A GLYCIDYL ESTER, SUCH AS GLYCIDYL METHACRYLATE, IS PREPARED BY CONTACTING AN UNSATURATED FATTY ACID, SUCH AS METHACRYLIC ACID, WITH AN ALKALI METAL BASE, SUCH AS NAOH, A SOLUTION OF ANALKALI METAL HYDROXIDE IN A FIRST REACTION ZONE TO FORM AN ALKALI METAL SALT, SUCH AS SODIUM METHAXRYLATE, IN THE PRESENCE OFA SOLVENT WHICH WILL AZEOTROPE WITH WATER AND WHICH IS FREE OF EPOXIDE GROUPS. SUBSTANTIALLY ALL OF THE WATER IS REMOVED FROM THE FIRST REACTION ZONE BY, FOR EXAMPLE, REMOVING A WATERSOLVENT AZEOTROPE. THE ALKALI METAL SALT IS THEN PHYSICALLY SEPARATED FROM THE REMAINING SOLVENT BY FILTRATION OR CENTRIFUGATION. THE ALKALI METAL SALT IS THEN REACTED IN A SECOND REACTION ZONE WITH DRY EPICHLOROHYDRIN UNDER SUBSTANTIALLY ANHYDROUS CONDITIONS TO FORM THE DESIRED GLYCIDYL ESTER.

Preparation of glycidyl esters of unsaturated acids

Abstract: A glycidyl ester, such as glycidyl methacrylate, is prepared by contacting an unsaturated fatty acid, such as methacrylic acid, with an alkali metal base in a first reaction zone to form an alkali metal salt, such as sodium methacrylate, in the presence of a solvent which will azeotrope with water and which is free of epoxide groups. Substantially all of the water is removed from the first reaction zone by, for example, removing a water-solvent azeotrope and, optionally, at least a portion of the solvent is removed. The alkali metal salt admixed with or suspended in at least a portion of the solvent is then contacted with a solid particulate drying agent free of halogen atoms and is thereafter reacted in a second reaction zone in the absence of the drying agent with dry epichlorohydrin under substantially anhydrous conditions to form the desired glycidyl ester. Optionally, the drying agent can remain in the second reaction zone provided said drying agent is such that it either reacts with water to form a hydrate or hydroxide or is a zeolite material having an average pore diameter less than six degrees Angstrom (°A.).