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US 4,110,355 AGranted
Anthraquinone compounds useful in photographic processes
AssigneePolaroid Corporation
InventorStanley M. Bloom
Life of this patent
Estimating the term…
Abstract
This invention relates to a novel class of compounds which are capable of reacting in such a way as to form a new heterocyclic ring, and as a function of such reaction and ring formation to split off a color-providing material.
Claims11
A compound of the formula ##STR49## wherein:
- A represents the atoms necessary to complete a benzene or naphthalene radical;
- D is an anthraquinone dye moiety;
- Z.sup.1 is hydrogen or a substituent replaceable by an oxidized aromatic amino color developer in elimination-coupling reactions;
- said substituent being selected from the group consisting of chloro, bromo, carboxy, sulfo, hydroxy, alkoxy and hydroxyalkyl;
- Y is the residue of an acid forming an amide with and reducing the basic character of the nitrogen atom to which it is bonded and is selected from the group consisting ##STR50## X.sup.1 is hydroxy or a primary, secondary or tertiary amino of the formula ##STR51## wherein each R.sup.3 is hydrogen, alkyl, phenyl, naphthyl, or each R.sup.3 may be alkylene so that the R.sup.3 's together with the nitrogen atom provide a heterocyclic ring having 5 or 6 carbon atoms or each R.sup.3 may be a lower alkyl having a substituent chosen from the group consisting of a hydroxy substituent, a methoxyethoxy substituent, a polyglycoloxy substituent, a carboxy substituent, an ethoxycarboxy substituent, a benzyl substituent, a phenyl substituent, a sulfo-phenyl substituent, an acetylaminophenyl substituent, a succinylaminophenyl substituent or a furane substituent;
- R is an anchoring substituent rendering the compound non diffusible said substituent containing a higher alkyl radical bonded to a single carbon atom of said aromatic nucleus formed by said A moiety;
- R.sup.1 is hydrogen or alkyl;
- and
- n is 2 or n may be 1 when X.sup.1 is a secondary or tertiary amino comprising an anchoring moiety rendering said compound non diffusible or R.sup.1 is an alkyl radical providing such an anchoring moiety.
6 more elements
A compound of the formula ##STR52## wherein:
- each of A and A.sup.1 represents the atoms necessary to complete a benzene or naphthalene radical;
- D is an anthraquinone dye moiety;
- Y is the residue of an acid forming an amide with and reducing the basic character of the nitrogen atom to which it is bonded and is selected from the group consisting ##STR53## X and X.sup.2 each is the substituent R, hydrogen, hydroxy, a primary, secondary or tertiary amino of the formula ##STR54## wherein each R.sup.3 is hydrogen, alkyl, phenyl, naphthyl, or each R.sup.3 may be alkylene so that the R.sup.3 's together with the nitrogen atom provide a heterocyclic ring having 5 or 6 carbon atoms or each R.sup.3 may be a lower alkyl having a substituent chosen from the group consisting of a hydroxy substituent, a methoxyethoxy substituent, a polyglycoloxy substituent, a carboxy substituent, an ethoxycarboxy substituent, a benzyl substituent, a phenyl substituent, a sulfo-phenyl substituent, an acetylaminophenyl substituent, a succinylaminophenyl substituent or a furane substituent provided that at least one of X and X.sup.2 must be hydroxy or amino;
- R and R.sup.4 each represent an anchoring substituent rendering the compound non diffusible, said substituent containing a higher alkyl radical bonded to a single carbon atom of said aromatic nucleus formed by said A or A.sup.1 moieties respectively;
- R.sup.1 is hydrogen or alky;
- and n and n.sup.1 each is 1 or 2 and each n and n.sup.1 may be 1 when one X or X.sup.2 is the substituent R or a secondary or tertiary amino comprising an anchoring moiety rendering the compound non diffusible or when R.sup.1 is an alkyl substituent providing such an anchoring moiety but when said substituents do not contribute an anchoring moiety, at least one of n and n.sup.1 must be 2.
3 more elements
A compound of the formula:
- ##STR55## wherein:
- each of R and R.sup.4 comprises an amide of at least 13 carbon atoms, said amide being bonded directly to a nuclear carbon atom of the shown benzene moiety or linked thereto through a phenylene or alkylene substituent;
- each of n and n.sup.1 is 1 or 2 provided that at least one of said n and n.sup.1 is 2;
- and
- D is an anthraquinone dye moiety.
2 more elements
A compound of the formula:
- ##STR56## wherein:
- D is an anthraquinone dye moiety;
- Z.sup.1 is hydrogen or a substituent replaceable by oxidized aromatic amino color developer in elimination-coupling reactions, said substituent being chloro, bromo, carboxy, sulfo, hydroxy, alkxoy or hydroxyalkyl;
- R.sup.1 is hydrogen or alkyl;
- X.sup.1 is hydroxy or amino;
- R is an anchoring moiety which renders the compound nondiffusible and comprises a higher alkyl of at least 10 carbon atoms bonded to a nuclear carbon atom of the shown benzene moiety by a linking group which is --CONH--;
- and n is 2.
4 more elements
A compound of the formula:
- ##STR57## wherein:
- D is an anthraquinone dye moiety;
- R.sup.1 is hydrogen;
- one of X.sup.1 or X.sup.2 is hydroxy or amino and the other is hydrogen or the substituent R;
- each R is an anchoring moiety rendering the compound nondiffusible and comprises a higher alkyl of at least 10 carbon atoms bonded to a nuclear carbon atom of the shown benzene moiety by a linking group which is --CONH--;
- and
- one of n and n.sup.1 is 2 and the other is 1 unless X.sup.1 or X.sup.2 is R, in which case both n and n.sup.1 are 1.
4 more elements
The compound:
- ##STR58##
The compound:
- ##STR59##
The compound:
- ##STR60##
Dependencies are inferred from the claim text.