Poly-carbonyloxyurethanes

Details Poly-carbonyloxyurethanes Poly-carbonyloxyurethanes

1976-02-23

1978-02-14

Thomas, Jr., James O.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

526 19, 526 20, 526 30, 526 52, 560 22, 560 29, 560 30, 560 31, 560 32, 560 33, 560144, 560162, 560164, 560165, 560166, C07C12506

Patent

active

040738000

DESCRIPTION:

BRIEF SUMMARY
This invention relates to nitrogen-containing compounds and more particularly to poly-carbonyloxyurethanes and their salts, and to their use as cross-linking and bonding agents for polymers.
According to the invention there are provided poly-carbonyloxyurethanes of the formula: alkyl, cycloalkyl or aryl carbon atoms, n is an integer of value at least 2, and each R which may be the same or different, is the residue of a monobasic carboxylic acid of formula R--CO--OH.
The invention also provides salts of these poly-carbonyloxyurethanes of the formula:
As linking groups represented by A there may be mentioned alkylene groups such as ethylene, 1,2- and 1,3-propylene, tetramethylene, hexamethylene, octamethylene, decamethylene, and dodecamethylene; cycloalkylene such as 1,4-cyclohexylene; arylene such as m- and p-phenylene; alkarylene groups derived from combinations of the foregoing groups such as methylene-bis-4-phenyl-, 2,2-propylene-bis-4-phenyl-, m- and p-xylylene; groups derived from one or more of the foregoing groups linked by heteroatoms or groups containing heteroatoms, e.g., bis-(alkyleneoxy)-phenylene groups; or radicals derived from polyalkylene oxides such as polyethylene oxides, condensates of alkylene oxides with glycols and other compounds containing two or more hydroxyl groups such as glycerol, 1,4-bis-(.beta.-hydroxyethoxycarbonyl)benzene, mannitol, sorbitol and sucrose; unsaturated polyvalent groupings, e.g., as derived from pentaerythritol dialkyl ether, and polymeric chains to which the oxycarbonyl groups are attached directly or through pendant groups, as for example in addition polymers and copolymers of alkyl esters of acrylic or methacrylic acids in which the oxycarbonyl group is attached to the alkyl radical of the ester group.
The symbol R can represent the residue of any monobasic carboxylic acid, but preferably represents an optionally substituted alkyl or aryl group, e.g., alkyl groups preferably containing from 1 to 4 carbon atoms such as ethyl, n- and iso-propyl, n-butyl, and especially methyl, but also n-octyl, n-decyl, n-dodecyl and n-octadecyl, and substituted derivatives of these such as chloroethyl, trifluoromethyl and perfluorooctyl, and aryl groups such as phenyl and o-, m- and p-tolyl and substituted aryl especially substituted phenyl groups such as nitrophenyl, chloro-, bromo-, iodo and fluoro-phenyl and alkoxyphenyl, e.g., methoxyphenyl.
n is preferably 2 or 3.
The preferred meaning for the radical A when n is 2 is the class consisting of alkylene radicals of formula (CH.sub.2).sub.m where m has a value of 2 to 10, phenylene, xylylene, or polyethyleneoxy radicals of the formula: tri(ethylene)amino and tri(methylenepropane).
The preferred meaning for the radical R is the class consisting of alkyl radicals of 1 to 17 carbon atoms, phenyl, dimethylaminophenyl, nitrophenyl, hydroxyphenyl, chlorophenyl and tolyl.
Thus, as preferred examples of formula (1) there may be mentioned:
As examples of cations represented by B, there may be mentioned alkali metal cations, e.g., sodium and potassium; however these salts tend to decompose at the usual ambient temperatures and it is preferred that B should represent an organic cation, derived from primary, secondary and especially tertiary amines, e.g., thiouronium or diethylammonium, but preferably trialkylammonium salts as derived e.g., from tertiary amines such as triethylamine, dimethylbenzylamine, triethanolamine, pyridine, 1,4-diazabicyclo-2,2,2-octane, or other tertiary amino compounds such as tetraalkylthioureas, tetraalkylthiuram mono- and di-sulphides, and dialkyldithiocarbamates, especially zinc dialkyldithiocarbamate and benzthiazyl derivatives. As a general rule, it is preferred that the cation should be derived from an amino compound of low volatility at ambient temperatures, since these are more stable than either the alkali metal salts or the salts formed by volatile amino compounds. All the salts are thermally unstable, the instability being increased by the presence of electron withdrawing substituents, e.g., halogen

REFERENCES:
nery, J. Chem. Soc. (c), pp. 1860-1864, (1969).
Carpino, J.A.C.S., 81, pp. 955-957.

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