Amino group-containing thiols and method for production thereof

Details Amino group-containing thiols and method for production thereof Amino group-containing thiols and method for production thereof

1998-04-10

2001-02-13

Barts, Samuel (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

C564S501000

Reexamination Certificate

active

06187958

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to novel amino group-containing thiols and also to a method for the production thereof. These novel thiols are compounds which contain a long-chain alkyl or alkenyl group in the molecule thereof and which show a high reactivity.
BACKGROUND OF THE INVENTION
Various thiol type compounds have been disclosed to date. Particularly, thiol compounds containing an amino group have long attracted interest and found utility in a wide range of applications because of their unique qualities. For example, cysteamine, a compound that has the simplest structure of all such amino group-containing thiol compounds, is useful as an intermediate for medicines and as an agent for treating hair and imparting permanent wave thereto. N-alkyl substituted compounds, namely amino group-containing thiols, which incorporate therein an alkyl group, have been found useful in the field of printing (as disclosed in JP-A-06-127,168), as intermediates for medicines (as disclosed in JP-A-48-44,244), in the field of photography (as disclosed in U.S. Pat. No. 3,221,013), and in the field of rubber (as reported in J. Am. Chem. Soc., Vol. 69, page 2672, 1947), for example.
Novel thiols containing an amino group, therefore, have reasons to promise a great usefulness. N-Methyldodecylaminoethane thiol, which is disclosed in DE 631,016 and undecylaminoethane thiol, which is reported in J. Org. Chem., Vol. 27, page 4222, 1962, are, for the time being, the only concrete examples of amino group-containing thiols that incorporate therein a long-chain alkyl or alkenyl group.
SUMMARY OF THE INVENTION
An object of the present invention, therefore, is to provide novel amino group-containing thiol compounds, which incorporate therein a long-chain alkyl or alkenyl group, and which are expected to find utility in various applications, said thiols having furthermore proved themselves useful as intermediates for synthesis.


REFERENCES:
patent: 3387953 (1968-06-01), Bouffard
patent: 3919290 (1975-11-01), Egger et al.
patent: 4808755 (1989-02-01), Wirth et al.
patent: 631 016 (1936-06-01), None
H.R. Snyder et al., “The synthesis of amino mercaptans from oleum sulphides” Journal of the American Chemical Society, vol. 69, No. 11, Nov. 1947, pp. 2672-2674.
R.J. Wineman et al., “Thiomethylation of amines with ethylene sulphide”, Journal of Organic Chemistry, vol. 27, No. 12, Dec. 1962, pp. 4222-4226.
R.T. Wragg, “Metal thiolates as initiators for the polymerisation of aklylene sulphides” Journal of the Chemical Society, Section-C: Organic Chemistry, 1969, pp. 2087-2092.
M.A. Allakhverdiev et al., “Synthesis and properties of alkoxy-substituted 1-aminopropane-2-thiols”, Russian Journal of Applied Chemistry, vol. 67, No. 11, part 2, Nov. 1994, pp. 1641-1644.

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