Radiation imagery chemistry: process – composition – or product th – Electric or magnetic imagery – e.g. – xerography,... – Post imaging process – finishing – or perfecting composition...
Patent
1997-06-27
1999-07-20
Dote, Janis L.
Radiation imagery chemistry: process, composition, or product th
Electric or magnetic imagery, e.g., xerography,...
Post imaging process, finishing, or perfecting composition...
430110, 430137, 556132, 556148, 562452, 562467, 562473, 562475, 562478, C03G 9097, C03G 1308, C07F 304, C07F 1502
Patent
active
059254874
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a composition comprising a toner resin and an aromatic carbocyclic hydroxy carboxylic acid (hereinafter "AHCA") containing at least one methylene group optionally substituted by hydroxy or optionally substituted amino (hereinafter "AHCAM") including salts and metal complexes thereof and the use of such compounds as negative charge control agents. Some of the compounds are novel.
EP 490370 discloses metal salts and complexes of pamoic acid and their use as negative charge control agents.
EP 490508 discloses compounds having a fused aromatic ring system having hydroxy, carboxy and hydroxyalkyl substituents such as 3hydroxy-4-hydroxymethyl-2-naphthoic acid including salts and metal complexes thereof and their use as corrosion inhibitors. It has now been found that such compounds and derivatives thereof are useful as negative charge control agents (hereinafter "CCA") in electroreprographic imaging processes.
Thus, according to the invention there is provided a toner resin composition comprising a toner resin and an AHCAM including salts and metal complexes thereof with the exception of pamoic acid.
The carboxylic acid group is preferably attached to a carbon atom adjacent to that carrying the hydroxy group in the AHCA.
The AHCA may be a single aromatic ring which is preferably a phenyl ring as in salicylic acid and derivatives thereof or the AHCA may have one or more rings fused to a carbocydic aromatic ring which may contain 5 or 6 atoms and may be saturated or unsaturated and may be carbocyclic or heterocyclic. Preferred examples of such compounds contain two rings, particularly those where the fused ring contains 6 atoms as in naphthalene, tetrahydronaphthalene, quinoline and tetrahydroquinoline. Specific examples of such AHCA's include 2-hydroxy-1-naphthoic, 1-hydroxy-2-naphthoic and 8-hydroxy-1-naphthoic acids and especially 3-hydroxy-2-naphthoic acid.
The AHCAM is obtainable by reacting the AHCA with formaldehyde optionally in the presence of a primary or secondary amine. Under such conditions the methylene group is located in the ortho- and/or para-position to the hydroxy group in the AHCA.
Preferably the AHCAM contains the one methylene group and it is also preferred that such methylene group is in the ortho position relative to the hydroxy group of the AHCAM
According to one aspect of the invention there is provided a composition comprising a toner resin and a AHCAM of formula 1 ##STR1## or a salt or metal complex thereof wherein ##STR2## R is halogen, hydroxy, nitro, carboxy, nitrdle, optionally substituted C.sub.1-18 -hydrocarbyl or two adjacent groups R together with the carbon atoms to which they are attached form an optionally substituted 5- or 6-membered fused ring; substituted C.sub.1-18 -hydrocarbyl or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached form a ring; and with the exception of pamoic acid.
Preferably, R.sup.1 and R.sup.2 are not both hydrogen.
When R, is hydrocarbyl it can be alkyl, alkenyl, alkynyl, aralkyl or aryl.
When R.sup.1 and R.sup.2 is hydrocarbyl it can be alkyl, cycloalkyl, aralkyl or aryl.
When R, R.sup.1, R.sup.2 or R.sup.3 is alkyl, it may be linear, branched or alicyclic and is preferably C.sub.1-12 -alkyl, more preferably C.sub.1-8 -alkyl and especially C.sub.1-6 -alkyl. Examples of such groups include methyl, ethyl, propyl, n-butyl, i-butyl, n-hexyl, i-hexyl, 2-ethylbutyl, 2-ethylhexyl, nonyl, dodecyl, octadecyl and cyclohexyl.
When R is alkenyl it is preferably C.sub.3-6 -alkenyl.
When R, R.sup.1, R.sup.2 or R.sup.3 is aralkyl it is preferably benzyl or 2-phenylethyl.
When R, R.sup.1 or R.sup.2 is aryl it is preferably phenyl.
When R, R.sup.1 or R.sup.2 is substituted hydrocarbyl, or when R.sup.3 is substituted alkyl, the substituent or substituents is preferably at least one of hydroxy, carboxy, halogen or nitrile or the hydrocarbyl groups may contain a divalent atom or group such as ##STR3## The preferred substituent in R,R.sup.1, or R.sup.2 is hydroxy.
When R is substituted hydrocarbyl it can also b
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J. March, Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, McGraw-Hill Book Co, NY (1968), p. 670.
N. Kondekar, et al. "Condensation of 3-Hydroxy-2-Naphthoic acid with formaldehyde", Industrial and Engineering Chemistry: Product Research and Development, 1973, pp. 135-137.
Campbell James Stanley
Fawkes David Melville
Gregory Peter
Dote Janis L.
Zeneca Limited
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