US 2010.0099806A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2010/0099806 A1 Houze et al. (43) Pub. Date: Apr. 22, 2010 (54) PROCESS FOR PRODUCING DIMETHYL (22) Filed: Oct. 22, 2009 CARBONATE CONTAINING COMPOSITIONS Related U.S. Application Data (75) Inventors: Eric C. Houze, Mullica Hill, NJ (US); Laura Ann Lewin, (60) Provisional application No. 61/196,987, filed on Oct. Greenville, NJ (US) 22, 2008. Correspondence Address: Publication Classification E DUPONT DE NEMOURS AND COMPANY (51) Int. C. LEGAL PATENT RECORDS CENTER CSK 5/04 (2006.01) BARLEY MILL PLAZA 25/1122B, 4417 LAN U.S. Cl. ........................................................ 524/28O CASTER PIKE (52) WILMINGTON, DE 19805 (US) (57) ABSTRACT (73) Assignee: E. I. DUPONT DE NEMOURS The present invention is directed to a process for producing AND COMPANY, Wilmington compositions containing dimethylcarbonate alone or in com (DE) bination with other co-solvent and more particularly directed to low VOC coating compositions used in automotive refinish (21) Appl. No.: 12/604,144 applications. US 2010/00998.06 A1 Apr. 22, 2010 PROCESS FOR PRODUCING DIMETHYL toxy ethoxy 222-propanol. 1-methyl naphthalene, 1-nitro CARBONATE CONTAINING COMPOSITIONS propane, 2.4-pentane dione, 2-ethylhexanol, 2-ethylhexyl acetate, 2-methyl-1-butanol, acetic anhydride, butyl acetate, FIELD OF INVENTION di-isoamyl ketone, diacetone alcohol, diethylene glycol monobutyl ether acetate, diethylene glycol, diisobutyl 0001. The present invention is directed to compositions ketone, ethylene glycol monoethyl ether acetate, glycol containing dimethyl carbonate and more particularly directed monopropyl ether acetate benzyl alcohol. 1,2-dichloroet to coating compositions directed to automotive refinish appli hane, 1,3-dioxane, 1,2-dimethoxyethane, 1-butanol. 1-me cations containing low VOCs (volatile organic compounds). thyl-2-pyrrolidinone, 1-propanol, 2-butanol, 2-ethylhexanol, 2-methoxyethanol. 2-propanol, acetone, acetonitrile, ben BACKGROUND OF INVENTION Zene, bis(2-methoxyethyl)ether, butyl cellosolve, carbon tet 0002 Many types of coating compositions, such as those rachloride, chlorobenzene, chlorobenzene, cyclohexane, used in the Industrial OEM (original equipment manufac cyclohexanol, cyclohexanone, dibasic ester, dichlo turer) and automotive refinish market utilize liquid coatings romethane, diethyl ether, diethylene glycol monobutyl ether, that contain organic solvents some of which upon evaporation diisopropyl ether, dimethyl ether, dimethylpropyleneurea, in the atmosphere can, depending upon the content of VOCs, dimethylsulphoxide, ethanol, ethyl acetate, ethyl benzene, be harmful to the environment and health. Generally VOCs ethylene glycol, ethyl amylketone, ethylbenzene, ethyl pro are considered to be those organic chemical compounds that pionate, ethylene glycol diacetate, ethylene glycol monobutyl have high enough vapor pressures under normal conditions to ether, ethylene glycol monoethyl ether, ethylene glycol significantly vaporize and enter the atmosphere, and to be monohexyl ether, ethylene glycol monomethyl ether, ethyl photochemically reactive, leading to the formation of tropho ene glycol monopropyl ether, fluorobenzene, formamide, fur spheric oZone. Thus, the manufacturers of coating composi fural, heptane, hexane, hexylene glycol, hexylene glycol tions endeavor to reduce the content of organic solvents in diacetate, iso-butyl acetate, iso-butyl isobutyrate, isoamyl their compositions. Alternatively, the manufacturers of coat alcohol, isobutanol, isopropanol, isopropyl acetate, 1,3,5-tri ing compositions employ certain solvents, such as acetone, methylbenzene, methane Sulphonic acid, methanol, methyl methyl acetate, Oxsol(R) 100 (1-chloro, 4-trifluoromethylben acetate, methyl celloSolve, methyl cyclohexane, methyl ethyl Zene) and t-butyl acetate, which have been considered exempt ketone, methyl amyl ketone, methyl amyl acetate, methyl VOC solvents by the United States Environmental Protection hexyl ketone, methyl n-propyl ketone, methylene chloride, Agency. However, each of these exempt solvents has signifi n-butyl propionate, n-heptyl acetate, n-hexyl acetate, n-nonyl cant issues in coatings formulations. Acetone and methyl acetate, n-octyl acetate, n-pentyl propionate, primary amyl acetate are extremely volatile, limiting the amount that can be acetate, propylene glycol monoethyl ether acetate, propylene used in a given formula and t-butyl acetate is not accepted as glycol t-butyl ether, propylene glycol isobutyl ether, propy VOC exempt by all Air Quality Management Districts (e.g., lene glycol monobutyl ether, propylene glycol monothyl California does not accept t-butyl acetate as a VOC exempt ether, propylene glycol monopropyl ether, methyl isobutyl Solvent) and is also unstable in Some coatings formulations. ketone, methyl tertbutyl ether, m-xylene, n,n-dimethyl for OxsolR 100 is a very poor coatings solvent due to its high mamide, n,n-dimethylacetamide, N,N-dimethylaniline, specific gravity (1.34) and weak solubility characteristics, so n-butanol, n-propyl acetate, o-Xylene, pentane, petroleum it is very expensive to use. Thus, a need still exists for a ether, propionic acid, p-Xylene, pyridine, sec-butyl alcohol, VOC-exempt solvent more suitable for use in coating com sec-butyl acetate, tert-butyl alcohol, tetrachloroethylene, tet positions, such as industrial and automotive refinish paints rahydrofuran, terpene, toluene, trichloroethylene, triethy that has a lower vapor pressure than acetone and methyl lamine, triethylene glycol monobutyl ether, triethylene gly acetate and is also an effective solvent compatible with vari col, monoethyl ether triethylene glycol, monomethyl ether, ous components, such as binder component, of a typical coat triethylene glycol diacetate, and a combination thereof, and ing composition. 0005 (B) mixing the solvent component with the binder component to form said composition. STATEMENT OF INVENTION DETAILED DESCRIPTIONS 0003. The present invention is directed to a process for producing a composition consisting essentially of a binder 0006. Unless stated otherwise: component and a solvent component, said process compris 0007. These and other features and advantages of the ing the steps of present disclosure will be more readily understood, by those 0004 (A) preparing the solvent component by mixing a of ordinary skill in the art, from a reading of the following solvent dimethyl carbonate with a co-solvent selected from detailed description. It is to be appreciated those certain fea the group consisting of aromatic hydrocarbon (135-146C), tures of the disclosure, which are, for clarity, described above aromatic hydrocarbon (150-190C), aromatic hydrocarbon and below in the context of separate embodiments, may also (182-219C), aliphatic hydrocarbon (100-150C), aliphatic be provided in combination in a single embodiment. Con hydrocarbon (100-163C), aliphatic hydrocarbon (115-149C), versely, various features of the disclosure that are, for brevity, aliphatic hydrocarbon (138-177C), aliphatic hydrocarbon described in the context of a single embodiment, may also be (138-185C), aliphatic hydrocarbon (145-205C), aliphatic provided separately or in any Sub-combination. In addition, hydrocarbon (150-205C), aliphatic hydrocarbon (150-210C), references in the singular may also include the plural (for aliphatic hydrocarbon (155-190C), aliphatic hydrocarbon example, “a” and “an may refer to one, or one or more) (170-210C), aliphatic hydrocarbon (180-210C), aliphatic unless the context specifically states otherwise. hydrocarbon (182-266C), aliphatic hydrocarbon (90-110C), 0008. The use of numerical values in the various ranges mineral spirit, 1,1,1-trichloroethane, 1,1,2-trichloroethane, specified in this application, unless expressly indicated oth 1.2-propylene glycol. 1,3-butanediol. 1,4-butanediol. 1-bu erwise, are stated as approximations as though the minimum US 2010/00998.06 A1 Apr. 22, 2010 and maximum values within the stated ranges were both a coating on the Substrate Surface having the desired coating preceded by the word “about.” In this manner, slight varia properties. Such as high gloss, mar-resistance and resistance tions above and below the stated ranges can be used to achieve to environmental etching. Substantially the same results as values within the ranges. 0013 “One-pack coating composition” means a thermo Also, the disclosure of these ranges is intended as a continu set coating composition comprising a crosslinkable compo ous range including every value between the minimum and nent and a crosslinking component that are stored in the same maximum values. container. However, crosslinkable functionalities on a crosslinkable polymer in the crosslinkable component are 0009. The crosslinkable functionalities are chemically blocked to prevent premature crosslinking, i.e., curing. After reactive functionalities provided on the backbone, atterminal the application of the one-pack coating composition on a end(s) or pendant from the backbone of a polymer chain. Substrate, the layer is typically exposed to elevated tempera When a crosslinkable polymer is mixed with a crosslinking tures to unmask the blocked crosslinkable functionalities. agent, crosslinkable functionalities on the crosslinkable poly Thereupon, the unmasked crosslinkable functionalities on the mer react with the crosslinking functionalities on the crosslinkable polymer in the layer react with the crosslinking crosslinking agent to form a network,