Maleic anhydride copolymers with methyl vinyl ether

Uses. Union Carbide consumes its vinyl ether production in the manufacture of glutaraldehyde [111-30-8J. BASF and GAF consume most of their production as monomers (see Vinyl polymers). In addition to the homopolymers, the copolymer of methyl vinyl ether with maleic anhydride is of particular interest. 

Because the urea-urease interaction leads to a pH increase, a polymer that increases erosion rate with increasing pH is needed. A useful polymer for this application is a partially esterified copolymer of methyl vinyl ether and maleic anhydride. This copolymer undergoes surface erosion with an erosion rate that is extraordinarily pH-dependent (J). The polymer dissolves by ionization of the carboxylic acid groups as shown below ... 

Figure 2. Hydrocortisone release rate at 35°C from a n-hexyl half-ester of a copolymer of methyl vinyl ether and maleic anhydride at pH 6.25 in the absence and presence of external urea. No external urea IC M external urea s10 M external urea. (Reproduced with permission from Ref. 2. Copyright 1979, American Pharmaceutical Association.)...

Several polymers were found to fit all or most of the above criteria and were used to prepare the carrier films. Many polymers have been used for this purpose, viz., ethyl cellulose, poly(y-benzyl glutamate), poly(vinyl acetate), cellulose acetate phthalate, and the copolymer of methyl vinyl ether with maleic anhydride. In addition to the base polymers, plasticizers were often needed to impart a suitable degree of flexibility. Plasticizers, which are found to be compatible with polymeric materials include, acetylated monoglycerides, esters of phthalic acid such as dibutyl tartarate, etc. An excipient was usually incorporated into the matrix of the carrier films. The excipients used were water-soluble materials, which are capable of creating channels in the polymer matrix and facilitate diffusion of the drug. PEGs of different molecular weights were used for this purpose. 

Satoh A, Kojima K, Koyama T, Ogawa H, Matsumoto I. Immobilization of saccharides and peptides on 96-well microtiter plates coated with methyl vinyl ether-maleic anhydride copolymer. Anal. Biochem. 1998 260 96-102. 

Even though partially esterified copolymers of methyl vinyl ether-maleic anhydride copolymers were orignally designed to dissolve abruptly with an increase in external pH, in a constant pH environment they undergo a controlled dissolution process and are therefore useful materials for the controlled release of therapeutic agents dispersed within them (12),... 

Materials. Two samples of polyacrylic acid, PAA-1 (4) and PAA-2, were obtained as gifts from S. C. Johnson Company. Their degrees of polymerization were 3090 and 4420, respectively, as calculated from the intrinsic viscosities of their sodium salts in 0.102V NaBr at 15°C using the appropriate relation of Takahashi and Nagasawa (5). The samples of the hydrolyzed copolymers of maleic anhydride witn ethylene (HEMA) and with methyl vinyl ether (HVMEMA) have been described previously (4). 

Commercially available water soluble copolymers of maleic anhydride with ethylene and methyl vinyl ether (presumably partially hydrolyzed to vicinal carboxylic acids) and triphenylsulfonium triflate were dissolved in water as a casting solvent. Spin-cast films were baked at 130 °C for 10 s, exposed to 254 nm radiation, and postexposure-baked at 130 °C for 40 s. Development with pure water provided negative tone images, presumably due to acid-catalyzed dehydration between vicinal carboxylic acids to form less polar anhydride, as was demonstrated for polarity reversal (4.3.1). However, a copolymer of maleic acid with methyl vinyl ether failed to provide any negative images,... 

Neutral and acidic polymers such as polyvinyl pyrrolidone, copolymers of polyvinyl pyrrolidone with vinyl acetate, and copolymers of methyl vinyl ether with half esters of maleic anhydride, are all used in hair styling and hair setting products. 

Copolymers maleic anhydride copolymer with ethylene or vinyl methyl ether, acrylic acid copolymers, and methacrylic acid copolymers (Eudragit)... 

Synonyms 2,5-Furandione, polymerwith methoxyethene 2,5-Furandione, polymer with methoxyethylene Methyl vinyl ether/maleic anhydride copolymer Poly (maleic anhydride-methyl vinyl ether) Poly (methyl vinyl ether-alt-maleic anhydride) Poly(methyl vinyl ether/maleic anhydride) Polyvinyl methyl ether-maleic anhydride PVM/MA Definition Copolymer of methyl vinyl ether and maleic anhydride Empirical (C4H2O3 CsHsO),... 

Sodium PVM/MA/decadiene crosspolymer Definition Copolymer of methyl vinyl ether and maleic anhydride crosslinked with 1,9-decadiene Uses Film-former in cosmetics, skin lightening and tanning prods. 

Alkenylsuccinic anhydrides made from several linear alpha olefins are used in paper sizing, detergents, and other uses. Sulfosuccinic acid esters serve as surface active agents. Alkyd resins (qv) are used as surface coatings. Chlorendric anhydride [115-27-5] is used as a flame resistant component (see Flame retardants). Tetrahydrophthalic acid [88-98-2] and hexahydrophthalic anhydride [85-42-7] have specialty resin appHcations. Gas barrier films made by grafting maleic anhydride to polypropylene [25085-53-4] film are used in food packaging (qv). Poly(maleic anhydride) [24937-72-2] is used as a scale preventer and corrosion inhibitor (see Corrosion and corrosion control). Maleic anhydride forms copolymers with ethylene glycol methyl vinyl ethers which are partially esterified for biomedical and pharmaceutical uses (189) (see Pharmaceuticals). 

Figure 9 Relationship between pH of dissolution and size of ester group in half-esters of methyl vinyl ether-maleic anhydride copolymers. (Reproduced with permission from Ref.

PVP forms molecular adducts with many substances. Insoluble complexes are formed when aqueous solutions of PVP are added to tannic acid, poly(acrylic acid) and methyl vinyl ether-maleic anhydride copolymer. Soluble complexes, called iodophors, are formed with iodine the solubility of iodine is increased from 0.034% in water at 25°C to 0.58% by 1% PVP. The resulting iodophor retains the germicidal properties of iodine. It is thought that the iodine is held in a PVP helix in solution. The influence of two samples of PVP on the solubility of testosterone is shown in Fig. 8.21. The PVP correspondingly increases the rate of solution of the steroid from solid dispersions. 

TWO organometallic polymers previously developed, tributyl-tin methaczylate/methyl methacrylate copolymer (TBTM/MeM) and the tributyltin ester of methyl vinyl ether/maleic anhydride (TBT-MVEt-MAn), were selected for use as wood impregnants. Full Cell and Enpty Cell Methods were used to treat wood with TBTCVMeM in "Rule 66" mineral spirits and in combination with P13 creosote. Although the polymers seem to be miscible with the creosote, this combination results in only surface penetration of wood when... 

Figure 4, Rate of polymer dissolution and hydrocortisone release from n-butyl half-ester of methyl vinyl ether-maleic anhydride copolymer containing 10 wt% drug, (Reprinted with permission from Ref. 12. Copyright 1980, John Wiley ...

Attempts have been made over time to improve the physical properties of novolacs. The use of phenol formaldehyde resins prepared in alkaline medium in photoresist compositions is mentioned in a Kalle Co. AG patent. The use of polyvinyl ethers in combination with novolacs to impart stickiness and plasticization action to the latter was patented by Christensen. Steinhoff, Isaacson, and Roelants of the Shipley Company mention the use of vinyl ethers in a patent on roller coating. Lower alkyl polyvinyl ethers, such as methyl, ethyl, butyl, and isobutyl, are added to novolac resins to improve coating flexibility and adhesion to metal surfaces as well as to improve resistance to mildly alkaline solutions. The use of styrene, methyl styrene, and styrene-maleic anhydride copolymers in combination with novolac was mentioned in several patents of both Shipley and Kalle Co. AG. When novolac is copolymerized with maleic anhydride, a resin that is readily soluble in alkaline solutions is obtained. ... 

The concept of hydrophobe modification of water-soluble polymers may have arisen from the hydrophobic half-esters of maleic anhydride-methyl vinyl ether copolymers, which were commercially available products in the 1960s (i). Replacement of the methyl vinyl ether with styrene produced more stable copolymers in general (2), but hydrophobes attached through the ester... 

The MA-VA copolymers of maleic anhydride (MA) with vinyl acetate (VA), (Chitanu et al., 2006) and MA-MMA copolymers with methyl methacrylate (MMA), (Chitanu et aL, 2007) are synthesized by free radical polymerization, purified by extraction and washed with diethyl ether. The composition is estimated by conductometric titration with aqueous O.IN NaOH in 1 1 acetone-water mixture and the molecular weight (Mw) by viscosimetric measurements in acetone at 30 °C. 

The copolymers obtained by radical copolymerization of maleic anhydride (MA) with acrylic or vinyl comonomers, and the maleic add copolymers, generally obtained by the hydrolysis of the maleic anhydride copolymers (Figure 10.1), can be called maleic copolymers. They were intensively studied from a theoretical perspective, but also for their applications [1-3]. Copolymers ofMA with electron-donating comonomers, such as styrene, vinyl acetate, N-vinyl pyrrolidone, and methyl vinyl ether, have an alternant structure [ 1 ], but when MA is copolymerized with electron-acceptor comonomers like methyl methacrylate, acrylonitrile, statistic copolymers are obtained [1,2]. MA units from the copolymers are very reactive active agents with amine or hydroxyl groups... 

Maleic copolymers, especially those with alkyl vinyl ethers, were used in drug formulations where only physical interactions occurred between the polymer matrix and the therapeutic agent. The polymers used in the formulations should be biocompatible, nontoxic, and should not induce allergic or pyrogenic reactions. Poly(maleic anhydride-co-methyl vinyl ether) (MA-MVE) is such a polymer, being approved by the FDA. Commercialized as Gantrez AN, MA-MVE copolymer is used as pharmaceutical excipient due to its bio/mucoadhesion and excellent film-forming properties [137]. 

In fact, the copolymers of methacrylic acid with maleic anhydride (14) and the copolymers of vinyl alcohol with maleic anhydride (127) obtained respectively from optically active (l-methyl-benzyl)-methacrylate or (l-methyl-benzyl)-vinyl-ether and maleic anhydride, were optically active, but their rotatory power was rather small. 

Consider the copolymerization of 1,3-butadiene with the following monomers n-butyl vinyl ether, methyl methacrylate, methyl acrylate, styrene, vinyl acetate, acrylonitrile, maleic anhydride. If the copolymerizations were carried out using cationic initiation, what would be expected qualitatively for the copolymer compositions List the copolymers in order of their increasing butadiene content. Would copolymers be formed from each of the comonomer pairs Explain what would be observed if one used anionic initiation ... 

New macroradicals have been obtained by proper solvent selection for the homopolymerization of styrene, methyl methacrylate, ethyl acrylate, acrylonitrile, and vinyl acetate, and by the copolymerization of maleic anhydride with vinyl acetate, vinyl isobutyl ether, or methyl methacrylate. These macroradicals and those prepared by the addition to them of other monomers were stable provided they were insoluble in the solvent. Since it does not add to maleic anhydride chain ends, acrylonitrile formed a block copolymer with only half of the styrene-maleic anhydride macroradicals. However, this monomer gave excellent yields of block polymer when it was added to a macroradical obtained by the addition of limited quantities of styrene to the original macroradical. Because of poor diffusion, styrene did not add to acrylonitrile macroradicals, but block copolymers formed when an equimolar mixture of styrene and maleic anhydride was added. 

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