IP Library Granted Patent US 9,309,410
Granted Patent B2
US 9,309,410 · App. 14/011,762 · Granted Apr 12, 2016

Colorant compounds

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Quick Facts
Patent No.
US 9,309,410
App. No.
14/011,762
Granted
Apr 12, 2016
Kind
B2
Abstract

Disclosed is a compound of the formula wherein R a and R b each, independently of the other, are hydrogen, alkyl, aryl, arylalkyl, or alkylaryl, R 1 and R 2 each, independently of the other, are hydrogen, alkyl, aryl, arylalkyl, or alkylaryl, provided that at least one of R 1 and R 2 is other than hydrogen, and R 3 , R 4 , R 5 , R 6 , and R 7 each, independently of the others, are alkyl, aryl, arylalkyl, alkylaryl, or a substituent other than hydrogen, alkyl, aryl, arylalkyl, or alkylaryl, wherein in each case alkyl, aryl, arylalkyl, or alkylaryl may or may not be substituted and may or may not have hetero atoms therein, and wherein two or more of R 3 , R 4 , R 5 , R 6 , and R 7 can be joined together to form a ring.

Claims (87)

1. A compound of the formula

wherein:

(a) Ra and Rb each, independently of the other, are:

(i) hydrogen;

(ii) alkyl, including substituted and unsubstituted alkyl, wherein hetero atoms may optionally be present in alkyl;

(iii) aryl, including substituted and unsubstituted aryl, wherein hetero atoms may optionally be present in aryl;

(iv) arylalkyl; including substituted and unsubstituted arylalkyl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of arylalkyl; or

(v) alkylaryl, including substituted and unsubstituted alkylaryl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of alkylaryl; and

(b) R1 and R2 each, independently of the other, are:

(i) hydrogen, provided that at least one of R1 and R2 is other than hydrogen;

(ii) alkyl, including substituted and unsubstituted alkyl, wherein hetero atoms may optionally be present in alkyl, provided that when R1 and R2 are both alkyl at least one of R1 and R2 has at least about 6 carbons;

(iii) aryl, including substituted and unsubstituted aryl, wherein hetero atoms may optionally be present in aryl;

(iv) arylalkyl, including substituted and unsubstituted arylalkyl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of arylalkyl; or

(v) alkylaryl, including substituted and unsubstituted alkylaryl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of alkylaryl.

2. A compound according to claim 1 of the formula

3. A compound according to claim 1 of the formula

4. A compound according to claim 1 wherein at least one of R 1 and R 2 is of the formula

- n -C n H 2n+1

wherein n is from about 8 to about 100.

5. A compound according to claim 1 wherein at least one of R 1 and R 2 is of the formula

wherein m+p is from about 8 to about 100.

6. A compound according to claim 1 wherein at least one of R 1 and R 2 is of the formula

wherein q+r is from about 8 to about 100.

7. A compound according to claim 1 wherein at least one of R 1 and R 2 is of the formula

wherein s+t is from about 8 to about 100.

8. A compound according to claim 1 wherein at least one of R 1 and R 2 is of the formula

wherein u+v is from about 8 to about 100.

9. A compound according to claim 1 wherein at least one of R 1 and R 2 is of the formula

wherein w+x is from about 8 to about 100.

10. A compound according to claim 1 wherein at least one of R 1 and R 2 is of the formula

wherein y+z is from about 8 to about 100.

11. A compound according to claim 1 wherein at least one of R 1 and R 2 is of the formula

wherein e+f is from about 8 to about 100.

12. A compound according to claim 1 wherein at least one of R 1 and R 2 has at least about 12 carbons.

13. A compound according to claim 1 wherein R 6 and R 7 are joined to form an aromatic ring.

14. A compound of the formula

wherein:

(a) R a and R b each, independently of the other, are:

(i) hydrogen;

(ii) alkyl, including substituted and unsubstituted alkyl, wherein hetero atoms may optionally be present in alkyl, having from about 1 to about 100 carbons;

(iii) aryl, including substituted and unsubstituted aryl, wherein hetero atoms way optionally be present in aryl, having from about 4 to about 24 carbons;

(iv) arylalkyl, including substituted and unsubstituted arylalkyl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of arylalkyl, having from about 5 to about 100 carbons; or

(v) alkylaryl, including substituted and unsubstituted alkylaryl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of alkylaryl, having from about 5 to about 100 carbons;

(b) at least one of R 1 and R 2 is:

(a)

- n -C n H 2n+1

wherein n is from about 8 to about 100;

(b)

wherein m+p is from about 8 to about 100;

(c)

wherein q+r is from about 8 to about 100;

(d)

wherein s+t is from about 8 to about 100;

(e)

wherein u+v is from about 8 to about 100;

(f)

wherein w+x is from about 8 to about 100;

(g)

wherein y+z is from about 8 to about 100;

(h)

wherein e+f is from about 8 to about 100; or

(i) a combination thereof; and

(c) R 3 , R 4 , R 5 , R 6 , and R 7 each, independently of the others, are:

(1) alkyl, including substituted and unsubstituted alkyl, wherein hetero atoms may optionally be present in alkyl, having from about 1 to about 100 carbons;

(2) aryl, including substituted and unsubstituted aryl, wherein hetero atoms may optionally be present in aryl, having from about 4 to about 24 carbons;

(3) arylalkyl, including substituted and unsubstituted arylalkyl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of arylalkyl, having from about 5 to about 100 carbons;

(4) alkylaryl, including substituted and unsubstituted alkylaryl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of alkylaryl, having from about 5 to about 100 carbons;

(5) a substituent other than hydrogen, alkyl, aryl, arylalkyl, or alkylaryl which is halogen, hydroxy, amino, imine, ammonium, pyridine, pyridinium, ether, aldehyde, ketone, ester, amide, carbonyl, thiocarbonyl, sulfate, sulfonate, sulfonic acid, sulfide, sulfoxide, phosphine, phosphonium, phosphate, phosphonate, nitrile, mercapto, nitro, nitroso, sulfone, acyl, acid anhydride, azide, azo, cyanato, isocyanato, thiocyanato, isothiocyanato, carboxylate, carboxylic acid, carbamate, carbamide, silyl, siloxyl, silane, or a combination thereof; or

(6) hydrogen;

wherein two or more of R 3 , R 4 , R 5 , R 6 , and R 7 can be joined together to form a ring and wherein two or three of R 3 , R 4 , R 5 , R 6 , and R 7 are hydrogen.

15. A compound of the formula

wherein:

(a) Ra and Rb each, independently of the other, are:

(i) hydrogen;

(ii) alkyl, including substituted and unsubstituted alkyl, wherein hetero atoms may optionally be present in alkyl, having from about 1 to about 100 carbons;

(iii) aryl, including substituted and unsubstituted aryl, wherein hetero atoms may optionally be present in aryl, having from about 6 to about 12 carbons;

(iv) arylalkyl, including substituted and unsubstituted arylalkyl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of arylalkyl, having, from about 7 to about 100 carbons; or

(v) alkylaryl, including substituted and unsubstituted alkylaryl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of alkylaryl, having from about 7 to about 100 carbons; and

(b) R1 and R2 each, independently of the other, are:

(i) hydrogen, provided that at least one of R1 and R2 is other than hydrogen;

(ii) alkyl: including substituted and unsubstituted alkyl, wherein hetero atoms may optionally be present in alkyl, having from about 1 to about 100 carbons, provided that when R1 and R2 are both alkyl at least one of R1 and R2 has at least about 6 carbons;

(iii) aryl, including substituted and unsubstituted aryl, wherein hetero atoms may optionally be present in aryl, having from about 6 to about 12 carbons;

(iv) arylalkyl, including substituted and unsubstituted arylalkyl, wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of arylalkyl, having from about 7 to about 100 carbons; or

(v) alkylaryl, including substituted and unsubstituted alkylaryl,

wherein hetero atoms may optionally be present in either the aryl or the alkyl portion of alkylaryl, having from about 7 to about 100 carbons.

16. A compound according to claim 15 wherein the compound is of the formula

17. A compound according to claim 15 wherein the compound is of the formula

Assignments (10)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 6, 2025
From: XEROX CORPORATION
To: GENESEE VALLEY INNOVATIONS, LLC
Reel/Frame 073842/0479 →
SECOND LIEN NOTES PATENT SECURITY AGREEMENT Recorded Jul 2, 2025
From: XEROX CORPORATION
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 071785/0550 →
FIRST LIEN NOTES PATENT SECURITY AGREEMENT Recorded Apr 11, 2025
From: XEROX CORPORATION
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 070824/0001 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS RECORDED AT RF 064760/0389 Recorded Feb 13, 2024
From: CITIBANK, N.A., AS COLLATERAL AGENT
To: XEROX CORPORATION
Reel/Frame 068261/0001 →
SECURITY INTEREST Recorded Feb 13, 2024
From: XEROX CORPORATION
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 066741/0001 →
SECURITY INTEREST Recorded Nov 20, 2023
From: XEROX CORPORATION
To: JEFFERIES FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 065628/0019 →
SECURITY INTEREST Recorded Jun 22, 2023
From: XEROX CORPORATION
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 064760/0389 →
RELEASE OF SECURITY INTEREST IN PATENTS AT R/F 062740/0214 Recorded May 18, 2023
From: CITIBANK, N.A., AS AGENT
To: XEROX CORPORATION
Reel/Frame 063694/0122 →
SECURITY INTEREST Recorded Nov 10, 2022
From: XEROX CORPORATION
To: CITIBANK, N.A., AS AGENT
Reel/Frame 062740/0214 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 28, 2013
From: BANNING, JEFFERY H.; WU, BO; STARR, NATHAN G.; DRAPPEL, STEPHAN V.
To: XEROX CORPORATION
Reel/Frame 031095/0457 →