Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2001-11-28
2004-12-21
Lambkin, Deborah C. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C549S320000, C549S323000, C528S192000, C528S354000, C528S415000, C252S182330
Reexamination Certificate
active
06833460
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to the preparation of gamma-butyrolactones and their use as cross-linking agents in various processes, including coating applications. Gamma-butyrolactones as cross-linking agents impart favorable properties to coating materials, do not pose serious health risks in commonly used coating processes, and therefore are suitable alternatives for isocyanates in coating compositions and application processes.
TECHNICAL BACKGROUND OF THE INVENTION
Materials commonly used for coatings, particularly those used in the automotive industry, utilize isocyanate compounds in coating formulations due to cross-linking properties of the compounds. Diisocyanate compounds react slowly at room temperature with amines and aliphatic alcohols to make polymers having urethane or urea crosslinks. Isocyanates may also cross-link with amines or alcohols during a baking step of the coating process and result in urethane or urea crosslinked polymers. Both urethanes and ureas are known to impart desirable properties in coating materials. Polymer backbones appended with hydroxyl groups or amine groups harden coating materials such as paint.
Isocyanates are volatile compounds. During the coating or baking step, persons working in the automotive industry, for example, are exposed to the vapors. Concern about the potential toxicity and health related effects associated with isocyanates suggests that alternatives are needed. The present invention discloses alternatives to isocyanates as cross-linking agents.
SUMMARY OF THE INVENTION
Disclosed in this invention is a lactone composition, as represented in structure I, wherein each n is independently 1 to 3; L is either present as a substituent having two functional groups, or is a direct bond forming a spiro-butyrolactone, or is H wherein rings of the structure are not connected, or is a radically polymerizable group wherein the rings of the structure are not connected; Y is either present independently as alkyl, alkenyl, alkynyl, aryl or a direct bond; each X is independently a substituent having a field effect, F, between −0.42 and +1.58
Also disclosed in this invention is a process comprising contacting lactones of structure B with an amine to form a hydroxy amide, wherein each Y is present independently as alkyl, alkenyl, alkynyl, aryl, or a direct bond; each X is independently a substituent having a field effect, F, between −0.42 and +1.58; wherein R is a branched or straight chain alkyl group of C
1
to C
10
, or an aryl group; and wherein each n is independently 1 to 3.
This invention also discloses a process comprising contacting a spiro-bislactone of structure A, wherein each n=1 to 3 independently and R is a branched or straight chain alkyl group of C
1
to C
10
, or an aryl group; with an amine to form a hydroxy amide.
Also disclosed in a process comprising contacting a bicyclo-lactone of structure C wherein R is a branched or straight chain alkyl group of C
1
to C
10
, an aryl group; or C(O)OE wherein E is independently alkyl or aryl, with an amine.
Also disclosed in this invention is a process comprising contacting a polymer comprising at least one polymerized lactone monomer of structure D with an amine to form a hydroxy amide, wherein each Y is present independently as alkyl, alkenyl, alkynyl, aryl, or a direct bond; each X is independently a substituent having a field effect, F, between −0.42 and +1.58; and wherein R
PG
is a radically polymerizable substituent group selected from the group consisting of styrene, acrylate, methacrylate, acrylamide, and methacrylamide; and wherein n is independently 1 to 3.
Still another disclosure of this invention is a process, comprising:
(i) performing the steps of any one of the disclosed processes; and applying a product resulting from step (i) to an object surface.
Also disclosed is an article treated by a process disclosed as described above.
REFERENCES:
patent: 2768148 (1956-10-01), Schildknecht et al.
patent: 3429851 (1969-02-01), Coates et al.
patent: 3678167 (1972-07-01), Ghosh et al.
patent: 4898977 (1990-02-01), Herold et al.
patent: 5010189 (1991-04-01), Herold et al.
patent: 5606078 (1997-02-01), Goschke et al.
patent: 5705658 (1998-01-01), Goschke et al.
patent: 6258895 (2001-07-01), Hocker et al.
patent: 6346599 (2002-02-01), Goldberg et al.
patent: 6423850 (2002-07-01), Anderson
patent: 0174866 (1993-03-01), None
patent: 1140721 (1969-01-01), None
patent: WO 00 78743 (2000-12-01), None
Copy International Search Report (PCT/US 02/41452) dated Oct. 10, 2003.
Rosowsky, Chemical Abstracts, Columbus Ohio, vol. 66, Feb. 13, 1967, No. 7.
Bensel et al.—Preparation of Bi(alpha-methylene-gamma-lactones) Institute for Organic Chemistry, Liebigs Ann Chem., 1977, 1572-1584.
Hayashi et al., Studies on Antitumor Substances XII Synthesis of Bis(2,3-epoxypropyl)amine Derivatives and the Reaction with Some Nucleophiles, Chem. Pharm Bull., 19(10)2003-2008 (1971).
Hansch et al. A Survey of Hammett Substituent Constants and Resonance and Field Parameters, Chem. Rev. 1991, 91, 165-195.
Stock, The Origin of the Inductive Effect,Journal of Chemical Education,49/6, 400-404, 1972.
Hosie et al., Failure of the Antiperiplanar Lone Pair Hypothesis in Glycoside Hydrolysis, Synthesis, Conformation and Hydrolysis of &agr;-D-xylopyranosyl-and &agr;-D-glucopyranosyl-pyridinium salts,J. Chem. Soc. Perkin Trans.,1121-1131, 1983.
H. E. Hogberg et al., Synthesis and gas chromatographic separation of the eight stereoisomers of diprionol and their acetates, components of the sex pheromone of pine sawfiles, Tetrahedron, 1990, 3007-3018, 46 (8).
Effects of Structure on Reactivity, Advanced Organic Chemistry: Reactions Mechanisms and Structures,J. Wiley and Sons, NY,278-286, 1992.
Lehmann, J. et al., 42210, Journal: CHBEAM; Chem. Ber.: GE; 107; 1974.
Ya, Y. et al., 45876; Journal; CHCCAL; Chem. Heterocycl. Compd. (Engl. Trans.); EN; 7; 1971.
Gonzalez, A., 5581994; Journal; SYNCAV; Synth. Commun.; EN; 21; 5; 1991.
Lehmann, J., 5749722; Journal; ARPMAS; Arch. Pharm. (Weinheim Ger.); GE; 317; 5, 1984.
Yamasaki, T. et al., 6066955; Journal; HTCYAM; Hetrocycles; EN; 43; 8; 1996.
C. Melchiorre et al., Molecular requirements at the cholinergic receptors. Importance of ether oxygens in the dioxoiane series, Eur. J. Med. Chem.—Chimica Therapeutics, 1978, 357-361, 13 (4).
E. I. du Pont de Nemours and Company
Lambkin Deborah C.
Sauerbrunn Linda K. H.
LandOfFree
Preparation and use of gamma-butyrolactones as cross-linking... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Preparation and use of gamma-butyrolactones as cross-linking..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Preparation and use of gamma-butyrolactones as cross-linking... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3316768