Maleic acid resins

Uses Solvent for vinyl resins, nitrocellulose-alkyd and nitrocellulose-maleic acid resins. 

Considerable interest has been shown in a novel cation exchanger first developed by Schomburg et. al. [43]. The material consists of a silica substrate of very uniform particle size coated with a poly(butadiene-maleic acid) resin which serves as the cation-exchange moiety. This material, which is now conunercially available, gives good separations of both monovalent and divalent metal ions in a single run. Ordinary eluents such as hydrochloric or methanesulfonic acid, or complexing eluents may be used [44,45]. 

Maleic acid resins give a wine red to olive brown color in the Liebermann-Storch-Morawski reaction (see Section 6.1.1). 

N-lsopropyl-N -phenyl-p-phenylenediamine I-Limonene Methylal Salicylic acid Sorbitol 1,3,5-Trihydroxybenzene resin mfg., alkyd Linseed acid resin mfg., artificial Benzyl chloride Maleic acid resin mfg., epoxy ester Linseed acid resin mfg., food-contact 2,6-Xylenol resin mfg., oil-soluble p-t-Amyl phenol... 

An unaccelerated, maleic acid resin for pultrusion, offering a good surface finish with low profile additives. 

A styrene free maleic acid resin for the manufacture of prepregs used for electrical purposes. 

Perfluoroalkoxy (PEA) resin Styrene-maleic acid copolymer (SMC)... 

The most important industrial use of pentaerythritol is in a wide variety of paints, coatings, and varnishes, where the cross-linking capabiUty of the four hydroxy groups is critical. Alkyd resins (qv) are produced by reaction of pentaerythritol with organic acids such as phthaUc acid or maleic acid and natural oil species. 

Other minor raw materials are used for specific needs. Eumaric acid [110-17-8] the geometric isomer of maleic acid, is selected to maximize thermal or corrosion performance and is the sole acid esterified with bisphenol A diol derivatives to obtain optimum polymer performance. CycloaUphatics such as hydrogenated bisphenol A (HBPA) and cyclohexanedimethanol (CHDM) are used in selective formulations for electrical apphcations. TetrahydrophthaUc anhydride [85-43-8] (THPA) can be used to improve resiUence and impart useful air-drying properties to polyester resins intended for coating or lining apphcations. 

Maleic acid and fumaric acid can also be, and are often, incorporated in alkyd resins in the form of the Diels-Alder adduct of rosin. The adducts are tribasic acids which provide pendent carboxyl groups in the resin molecules, which can be saponified to give ionic, and, in turn, water-soluble characteristics to the resin. However, the resultant alkyds often have poorer color retention, toughness, gloss retention, and exterior durabiUty. 

Maleic anhydride, maleic acid, and fumaric acid), foUowed by amine neutraH2ation. Baking primers made with such resins provide the same corrosion... 

Vinyls. Vinyl resins are thermoplastic polymers made principally from vinyl chloride other monomers such as vinyl acetate or maleic anhydride are copolymerized to add solubUity, adhesion, or other desirable properties (see Maleic anhydride, maleic acid, and fumaric acid). Because of the high, from 4,000 to 35,000, molecular weights large proportions of strong solvents are needed to achieve appHcation viscosities. Whereas vinyls are one of the finest high performance systems for steel, many vinyl coatings do not conform to VOC requirements (see Vinyl polymers). 

Most conventional general purpose resins employ either maleic acid (usually as the anhydride) or its fra/jj-isomer fumaric acid (which does not form an anhydride) as the unsaturated acid (Figure 25.3). 

Fumaric acid may be prepared by heating maleic acid, with or without catalysts. It is also obtained as by-product in the manufacture of phthalic anhydride from naphthalene. The acid is a solid melting at 284°C. Fumaric acid is sometimes preferred to maleic anhydride as it is less corrosive, it tends to give lighter coloured products and the resins have slightly greater heat resistance. 

An alternative approach is first to produce a polyester resin containing an excess of maleic acid residues (maleate groups) and then to react this with the hexachlorocyclopentadiene to form the adduct in situ Figure 25.S). 

The basic patent (US Patent 3256219) indicates that the system is viable with conventional resins although special grades have been developed that are said to be particularly suitable. One example in the patent recommends the use of a polyester prepared using a maleic acid, phthalic acid and propylene glycol ratio of 2 1 33 and with an acid value of 40. To 500g of such a resin are added 10g of benzoyl peroxide and 167 g of styrene. Water 600 g is then stirred in at 5-10°C until a white creamy water-in-oil emulsion is obtained. A solution of 0.8 g of dimethyl-p-toluidine in lOOg of styrene is stirred into the emulsion and the resin is cast between plates and cured at 50°C. 

The methylated maleic acid adduct of phthalic anhydride, known as methyl nadic anhydride VI, is somewhat more useful. Heat distortion temperatures as high as 202°C have been quoted whilst cured systems, with bis-phenol epoxides, have very good heat stability as measured by weight loss over a period of time at elevated temperatures. The other advantage of this hardener is that it is a liquid easily incorporated into the resin. About 80 phr are used but curing cycles are rather long. A typical schedule is 16 hours at 120°C and 1 hour at 180°C. 

Oxidation of n-hutane to maleic anhydride is becoming a major source for this important chemical. Maleic anhydride could also be produced by the catalytic oxidation of n-butenes (Chapter 9) and benzene (Chapter 10). The principal use of maleic anhydride is in the synthesis of unsaturated polyester resins. These resins are used to fabricate glass-fiber reinforced materials. Other uses include fumaric acid, alkyd resins, and pesticides. Maleic acid esters are important plasticizers and lubricants. Maleic anhydride could also be a precursor for 1,4-butanediol (Chapter 9). 

The carboxylated polymers [476,499] include acrylic, methacrylic or maleic acid polymers (all obviously anionic in character) applied mainly from aqueous emulsion and particularly in combination with crease-resist or durable press resins. This type of chemistry has already been discussed in section 10.8.2. A particularly common example is the copolymer of acrylic acid with ethyl acrylate (10.247). In general the best balance of properties is obtained with 75-85% ethyl acrylate (y) and 25-15% acrylic acid (x), with an average chain length of about 1300 (x + y) units 65-85% ethyl acrylate with 35-15% methacrylic acid is also suitable. When the content of the acidic comonomer increases above about 30% the durability to washing tends to decrease, whilst longer chains tend to give a stiffer handle [499]. 

A photosensitive composition, consisting of an aromatic azide compound (4,4 -diazidodi-phenyl methane) and a resin matrix (poly (styrene-co-maleic acid half ester)), has been developed and evaluated as a negative deep UV resist for high resolution KrF excimer laser lithography. Solubility of this resist in aqueous alkaline developer decreases upon exposure to KrF excimer laser irradiation. The alkaline developer removes the unexposed areas of this resist. 

The photosensitive azide compound was 4,4 -diazidodiphenyl methane (m.p. 44.0 t). The poly(styrene-co-maleic acid half ester) was used as a resin matrix. 

A negative deep UV resist, consisting of a photosensitive 4,4 -diazidodiphenyl methane and a poly-(styrene-co-maleic acid half ester) resin, has been found to meet the requirements needed for KrF excimer laser lithography. 

Today, glycerol has over 2000 different applications, in cosmetics, pharmaceutics, foods and drinks, tobacco, paper, inks and printing colors, the production of phthalic and maleic alkyd resins and crosslinked polyesters, and as a hydraulic agent. Polyglycerols have a wide range of applications as emulsifiers, and technical esters of glycerol with fatty acids are used as synthetic lubricants [4]. 

Fumaric acid, a metabolite of many fungi, lichens moss and some plants, and mainly used as the diacid component in alkyd resins, is produced commercially to some extent by fermentation of glucose in Rhizopus arrhizus yet productivity improvements appear essential for the product to be an option for replacing its petrochemical production by catalytic isomerization of maleic acid. 

Maleic anhydride (2,5-furandione) is obtained as a by-product in the production of phthalic anhydride and by the vapor phase oxidation of butylene or crotonaldehyde. It is also obtained by the dehydration of maleic acid and by the oxidation of benzene. Maleic anhydride is used for the production of unsaturated polyester resin. This reactant, like most reactants, is fairly toxic and should be treated as such. 

Figure 4.4—The film resins. Example of a resin made of hard nuclei on which has been deposited a copolymer made by the reaction of maleic acid on 1,3-butadiene (reproduced by permission of Dionex).

Acrylic acid [79-10-7] - [AIR POLLUTION] (Vol 1) - [ALDEHYDES] (Vol 1) - [ALLYL ALCOHOL AND MONOALLYL DERIVATIVES] (Vol 2) - [MALEIC ANHYDRIDE, MALEIC ACID AND FUMARIC ACID] (Vol 15) - [POLYESTERS, UNSATURATED] (Vol 19) - [FLOCCULATING AGENTS] (Vol 11) - [CARBOXYLICACIDS - SURVEY] (Vol 5) -from acetylene [ACETYLENE-DERIVED CHEMICALS] (Vol 1) -from acrolein [ACROLEIN AND DERIVATIVES] (Vol 1) -acrylic esters from [ACRYLIC ESTER P OLYMERS - SURVEY] (Vol 1) -from carbon monoxide [CARBON MONOXIDE] (Vol 5) -C-21 dicarboxylic acids from piCARBOXYLIC ACIDS] (Vol 8) -decomposition product [MAT. ETC ANHYDRIDE, MALEIC ACID AND FUMARIC ACID] (Vol 15) -economic data [CARBOXYLIC ACIDS - ECONOMIC ASPECTS] (Vol 5) -ethylene copolymers [IONOMERS] (Vol 14) -in floor polishes [POLISHES] (Vol 19) -in manufacture of ion-exchange resins [ION EXCHANGE] (V ol 14) -in methacrylate copolymers [METHACRYLIC POLYMERS] (Vol 16) -in papermaking [PAPERMAKING ADDITIVES] (Vol 18)... 

Maleic anhydride CAS. 108-3I-6. til, maleic acid [CAS 110-16-7]. (2), and I umarie acid [CAS 110-17-81. i3) are multifunctional chemical intermediates that lind applications in nearly every Held id industrial chemistry. Each molecule contains two acid carbonyl groups and a double bond in the u. position. Maleic anhydride and maleic acid are important raw materials used in the manufacture of phthalic-type alkyd and polyester resins, surface coatings, lubricant additives, plasticizers. copolymers, and agricultural chemicals [see Alkyd Resins Polymers, and Lubricant). Both chemicals derive their common names from naturally occurring malic acid. 

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