organic chemicals - C&EN Global Enterprise (ACS Publications)

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organic chemicals

FROM ROHM A N D H A A S COMPANY INDUSTRIAL CHEMICALS DEPARTMENT

ACRYLIC MONOMERS Acrylic Esters 0 Acrylates CH2 = CHC0R

Methacrylates CH2 = C —COR Polymers derived from this series of acrylic and methacrylic esters vary from soft, elastic, film-forming m a t e r i a l s t o h a r d p l a s t i c s . These esters may be polymerized or copolymerized by bulk, suspension, solvent, and emulsion methods. They also copolymerize with many other monomers; an outstanding contribution they make to the resulting copolymer systems is improved resistance to

heat, light, and weathering. Most of these monomers are available in low-inhibitor grades which offer possibilities for product improvement and production savings. Typical uses: plastic sheet and molding powder; latex paints; thermoplastic or thermosetting coatings for automobiles, appliances, and aluminum siding; p r i n t i n g i n k s ; floor p o l i s h e s ; bronze and aluminum paints; adhesives; textile finishes; paper coatings; leather finishes; elastomers. When added to a rubber or P V C c o m p o u n d , b u t y l è n e dimethacrylate or trimethylolpropane trimethacrylate function as plasticizers during processing, and then polymerize during cure t o i m p a r t h a r d n e s s to t h e vulcanizate.

Methyl Acrylate Ethyl Acrylate Butyl Acrylate Isobutyl Acrylate 2-Ethylhexyl Acrylate Methyl Methacrylate Ethyl Methacrylate Butyl Methacrylate Isobutyl Methacrylate Isodecyl Methacrylate Lauryl Methacrylate Tridecyl Methacrylate Stearyl Methacrylate 1,3-Butylene Dimethacrylate Trimethylolpropane Trimethacrylate

Acrylic Acids CH2 = CHCOOH Glacial Acrylic Acid CH3

I CH2 = C - COOH Glacial Methacrylic Acid

Glacial methacrylic acid and glacial acrylic acid can be polymerized to water-soluble polymers. They also copolymerize with many other monomers and provide means for introducing carboxyl groups into copolymers. In copolymers, these acids can: 1) improve adhesion properties, 2) improve

freeze-thaw and mechanical stability of polymer dispersions, 3) provide solubility in alkalies, including ammonia, 4) increase resistance to attack by oils, and 5) provide reactive centers for crosslinking by divalent metal salts, diamines, or epoxides.

Functional Group Methacrylate Monomers CH 3 0 CH2 = C - C0CH2CH2 - OH Hydroxyethyl Methacrylate

CH 3 0

I

II

CH 2 = C — C0C 3 H 6 0H Hydroxypropyl Methacrylate

Hydroxyethyl methacrylate and hydroxypropyl methacrylate permit the introduction of reactive hydroxyl groups into copolymers — and thus offer possibilities for

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organic chemicals

FROM

Functional Group Methacrylate Monomers (continued) CH3 0 D imethylam inoethyl methacrylate and t-butylaminoethyl methacrylate offer means for making copoly­ mers with pendent amino groups. The amino groups can: 1) serve as sites for secondary crosslinking, 2) provide a way to make the co­ polymer acid-soluble, 3) promote adhesion to selected substrates, 4) provide anchoring sites for dyes and pigments. Application possi­ bilities: coatings, cationic pig­ ments and starches, dispersants,

subsequent crosslinking with an OH-reactive difunctional agent such as a diisocyanate, diepoxide, or melamine-formaldehyde resin. Hydroxyl groups also promote adhesion to polar substrates. Typ­ ical uses: thermosetting acrylic coatings for autos and appliances, nonwoven fabric binders, wool stabilizers, laminating resins, syn­ thetic fibers. Now offered in 94% grades—new lower-cost, solventfree, concentrated grades.

CH2 = C - C0CH2CH2N