Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1995-03-27
1996-06-04
O'Sullivan, Peter
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
106 2, 106 1505, 106 1832, 252194, 252380, 252403, 422 1, 424405, 428541, 504158, A01N 3312, C07C21163, C07C20900
Patent
active
055234879
ABSTRACT:
Quaternary ammonium carbonates having the formula ##STR1## wherein R.sup.1 is a C.sub.1 -C.sub.20 alkyl or aryl-substituted alkyl group and R.sup.2 is a C.sub.8 -C.sub.20 alkyl group have been synthesized.
These compounds and compositions further comprising the corresponding quaternary ammonium bicarbonate ##STR2## wherein R.sup.1 is the same or a different C.sub.1 -C.sub.20 alkyl or aryl-substituted alkyl group and R.sup.2 is the same or a different C.sub.8 -C.sub.20 alkyl group and/or the corresponding quaternary ammonium metal carbonate ##STR3## wherein R.sup.1 is the same or a different C.sub.1 -C.sub.20 alkyl or aryl-substituted alkyl group; R.sup.2 is the same or a different C.sub.8 -C.sub.20 alkyl group and M is a non-coupler metal, are prepared by reacting two reactants, a C.sub.1 -C.sub.20 alkyl or aryl-substituted alkyl, C.sub.8 -C.sub.20 alkyl quaternary ammonium chloride and a metal hydroxide, in a solvent comprising a C.sub.1 -C.sub.4 normal alcohol. The amount of metal chloride reactant is that amount sufficient to yield the C.sub.1 -C.sub.20 alkyl or aryl-substituted alkyl, C.sub.8 -C.sub.20 alkyl quaternary ammonium hydroxide, a metal chloride, and optionally unreacted metal hydroxide. The resultant quaternary ammonium hydroxide and any unreacted metal hydroxide are then reacted with carbon dioxide to yield the quaternary ammonium carbonate and optionally metal carbonate.
Also provided is a method for preserving a wood substrate. Accordingly, the substrate is treated with a metal coupler-free wood preservative system comprising a biocidal effective amount of the carbonate quats above, preferably those prepared by the method above, and a solvent.
REFERENCES:
patent: 2994699 (1961-08-01), De Benneville
patent: 3169983 (1965-02-01), Hunter
patent: 3233645 (1965-12-01), Kalberg
patent: 3281458 (1966-10-01), Jordan et al.
patent: 3301815 (1967-01-01), Hunyar et al.
patent: 3646147 (1972-02-01), Dadekian
patent: 4216168 (1980-08-01), Evans et al.
patent: 4585795 (1986-04-01), Linderborg
patent: 4929454 (1990-05-01), Findlay et al.
patent: 5004760 (1991-04-01), Patton et al.
patent: 5334763 (1994-08-01), Washington et al.
Whitten et al., "General Chemistry" Saunders College Publishing, Philadelphia (1981) p. 334.
L. Jin & K. Archer, "Cooper Based Wood Preservatives: Observation on Fixation, Distribution and Performance" preprints for American Wood-Preservers' Association Apr. 1991 meeting.
D. D. Nicholas et al., "Distribution and Permanency of DDAC in Southern Pine Sapwood Treated by the Full-Cell Process", Forest Products Journal 41(1):41-45 (Jan. 1991).
L. Jin & A. F. Preston, "The Interaction of Wood Preservatives With Lignocellulosic Substrates" Holzforschung 45(6):455-459 (1991).
Proc. Amer. Wood-Preservers Assoc. 80:191-209 (1984).
Y. Nakama, F. Harusawa & I. Murotani, "Cloud Point Phenomena In Mixtures of Anionic and Cationic Surfactants in Aqueous Solution" JAOCS 67 (11):717-721, (Nov. 1990).
A. F. Preston et al., "Recent Research On Alkylammonium Compounds In The U.S.", American Wood-Preservers' Association, 83:331-348 (1987).
"Quaternary Ammonium Compounds, Fine & Functional Chemicals" AKZO, pp. 1, 3-20 (1991).
D. D. Miller et al., "Control of Aggregate Structure With Mixed Counterions In An Ionic Double-Chained Surfactant", Langmuir 4:(6):1363-1367 (1988).
Ewa Z. Radlinska et al., "Supra-Self Assembly: Vesicle-Micelle Equilibrium", Colloids and Surfaces 46:213-217 (1990).
J. E. Brady et al., "Counertion Specificity As The Determinant of Surfactant Aggregation" J. Phys. Chem. 90:1853-1859, (1986).
D. D. Miller et al., "Fluorescence Quenching In Double-Chained Surfactants. 1. Theory of Quenching In Micelles and Vesicles", J. Phys. Chem. 93:323-325 (1989).
J. E. Brady et al., "Spontaneous Vesicles", J. American Chemical Society 106:4279-4280 (1984).
A. F. Preston, "Dialkyldimethylammonium Halides As Wood Preservatives", JAOCS 60(3):567-570 (Mar. 1983).
D. D. Nicholas & A. F. Preston, "Interaction of Preservatives With Wood" Chemistry of Solid Wood, pp. 307-320 (1984).
E. W. Anacker and H. M. Ghose, "Counterions and Micelle Size I. Light Scattering by Solutions of Dodecyltrimethylammonium Salts", vol. 67 pp. 1713-1715, (Aug. 1963).
L. Sepulveda et al., "A New and Rapid Method for Preparing Long-Chain Alkytrimethyl-ammonium Salts with A Variety of Counterions", Journal of Colloid and Interface Science 117 (2):460-463 (Jun. 1987).
E. Jugerman et al., Cationic Surfactants, pp. 56-57, Marcel Dekker Inc. (1969).
"Quaternary Ammonium Compounds", K.O. 19:521-531 (1982).
"Quaternary Ammonium Compounds", K.O. 16:859-865 (1968).
Astle, "Industrial Organic Nitrogen Compounds", Reinhold Publ. pp. 64-67 (1961).
"Organic Reactions" 11, Chaptr. 5, Krieger Publ. Co., pp. 376-383 (1960).
Carl Kaiser et al., "Alkenes via Hofmann Elimination: Use of Ion-Exchange Resin For Preparation Of Quaternary Ammonium Hydroxides: Diphenylmethyl Vinyl Ether", Organic Synthesis, Collective vol. VI, pp. 552-554, John Wiley, Inc. (1988).
Y. Talmon et al., "Spontaneous Vesicle Formed From Hydroxide Surfactants: Evidence From Electron Microscopy" Science 221:1047-1048 (Sep. 9, 1983).
Awata et al., "Cathodic Esterification of Carboxylic Acids", Chemistry Letters, pp. 371-374 (1985).
A. W. Ralston et al., "The Solubilities of Long-Chain Dialkyldimethyl-Ammonium Chlorides In Organic Solvents", Contribution from the Research Laboratory of Armour and Company 13:186-190 (1948).
A. W. Ralston et al., "Conductivities of Quaternary Ammonium Chlorides Containing Two Long-Chain Alkyl Groups", Contribution from the Research Laboratory of Armour and Company 70:977-979 (Mar. 1948).
Organic Chemistry 35:3597-3598 (1941).
T. P. Schultz et al., "Role of Stilbenes in the Natural Durability of Wood: Fungicidal Structure--Activity Relationships", PhytoChemistry 29:1501-1507 (1990).
85: 12353x "A Simple Preparation of Anhydrous Tetraalkylammonium Salts" (Chem. Abstract) (1976).
115: 87485b "Wood Preservatives Containing Quaternary Ammonium Salts With Polymers" (Chem. Abstract) (1991).
112: 212470j "Agrochemical Fungicides Containing Quaternary Ammonium Salts" (Chem. Abstract) (1990).
113: 153776j "Microbicidal Thermoplastic Resin Compostions" (Chem. Abstract) (1990).
112: 79768u "Noncorrosive Quaternary Ammonium Compounds As Wood Preservatives" (Chem. Abstract) (1990).
113: 163999y "Capacitor Driving Electrolytes and Their Preparation" (Chem. Abstract) (1990).
112: 54969x "Preparation of Quaternary Ammonium Hydroxides Free of Halogens" (Chem. Abstract) (1990).
110: 212114e "Process For Producing Quaternary Salts" (Chem. Abstract) (1989).
114: 246824j "Preparation of Carbonic Half-Esters of Betaine Structure" (Chem. Abstract) (1989).
98: 20032x "Didecyldimethylammonium Chloride--A Quaternary Ammonium Wood Preservative" (Chem. Abstract) (1993).
91: 1526227b "Efficacy of Acidic and Alkaline Solutions of Alkylammonium Compounds As Wood Preservatives" (Chem. Abstract) (1979).
113: 154360f "Microbicidal Coating Compositions Containing Quaternary Ammonium Salts" (Chem. Abstract) (1990).
109: 124403x "Quaternary Ammonium Salt-Containing Wood Preservatives" (Chem. Abstract) (1988).
103: 109954k "Clear Aqueous Disinfectant Solutions Containing Chlorhexides Lactate or Gluconate and Quaternary Salts" (Chem. Abstract) (1989).
70: 111034d "Quaternary Ammonium Bases Compatible with Scintillation-Counting Liquids" (Chem. Abstract) (1969).
60: 166447d "Nematocodal Quaternary Ammonium Salts" (Chem. Abstract) (1964).
91: 109311g "Composition for Removing Water from Surfaces of Articles" (Chem. Abstract) (1979).
75: 119170u "Corrosion-Resistant Lubricants and Antistatic Agents" (Chem. Abstract) (1971).
66: 66227y "Stabilization of Vinyl Resins with Organic Quaternary Ammonium Nitrates" (Chem. Abstract) (1967).
66: 1953n "N-Alkyl Ammonium Humates" (Chem Abstract) (1967).
97: 91725 "Perfluoroalkyl Alkanols" (Chem Abst.) (1982).
Lonza Inc.
O'Sullivan Peter
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