IP Library Granted Patent US 6,960,248
Granted Patent B2
US 6,960,248 · App. 10/444,410 · Granted Nov 1, 2005

Cyclic bisamides useful in formulating inks for phase-change printing

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Quick Facts
Patent No.
US 6,960,248
App. No.
10/444,410
Granted
Nov 1, 2005
Kind
B2
Abstract

Cyclic bisamides may be used to formulate inks for jet ink printing. The cyclic bisamide may be prepared from a cyclic diamine and acylic monocarboxylic acids. Conversely, the cyclic bisamide may be prepared from a cyclic diacid and acylic monoamines. The performance properties of the product may be enhanced by adding some additional difunctional reactant(s), e.g., diacid or diamine. A blend of bisamides may provide better performance properties than either of the component bisamides alone, where the blend includes at least one cyclic bisamide. The bisamides, in combination with an image-forming material, and optionally in combination with other materials, is taken to a molten form and then applied to a substrate to provide a printed substrate.

Claims (14)

1. A non-aqueous composition comprising an image-forming material and a cyclic bisamide of formula (I)

wherein n is 0 or an integer from 1 to 10, m is 0 or 1 to provide a cyclopenty ring or cyclohexyl ring, respectively, and G is an amide-containing group.

2. The composition of claim 1 having a viscosity at 130° C. of less than 100 cPs.

3. The composition of claim 1 having a melting point of 100-130° C.

4. The composition of claim 1 having an acid number of 0.1-10 and an amine number of 0.1-10.

5. The composition of claim 1 wherein the cyclic bisamide constitutes at least 10 wt % of the composition.

6. The composition of claim 1 wherein the image-forming material is a pigment or a dye.

7. The composition of claim 1 wherein G is —NH—C(O)—R and R is a C1-C75 alkyl group independently selected at each occurrence.

8. The composition of claim 1 wherein the cyclic bisamide is described by formula (IIIa)

9. The composition of claim 8 wherein n is zero at each occurrence, G is —NH—C(O)—R at each occurrence, and R is a C8-C22 alkyl group independently selected at each occurrence.

10. The composition of claim 1 wherein the cyclic bisamide is described by formula (IIa)

11. The composition of claim 10 wherein n is zero at one occurrence, n is 1 at one occurrence, G is —NH—C(O)—R at each occurrence, and R is a C8-C22 alkyl group independently selected at each occurrence.

12. The composition of claim 1 comprising a second bisamide compound, where the second bisamide compound is not described by formula (I).

13. The composition of claim 12 wherein the second bisamide compound comprises a polyether moiety located between two amide groups.

Assignments (20)
CORRECTIVE ASSIGNMENT TO CORRECT THE PATENT NO. 8837224 TO PATENT NO. 7737224 PREVIOUSLY RECORDED AT REEL: 037448 FRAME: 0453. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 11, 2022
From: KRATON POLYMERS U.S. LLC; ARIZONA CHEMICAL COMPANY, LLC
To: BANK OF AMERICA, N.A.
Reel/Frame 060344/0919 →
RELEASE OF SECURITY INTEREST Recorded Mar 15, 2022
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
To: ARIZONA CHEMICAL COMPANY, LLC
Reel/Frame 059366/0727 →
PATENT SECURITY AGREEMENT Recorded Jan 7, 2016
From: ARIZONA CHEMICAL COMPANY, LLC
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
Reel/Frame 037457/0928 →
RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded Jan 6, 2016
From: ANTARES CAPITAL LP, AS SUCCESSOR TO GENERAL ELECTRIC CAPITAL CORPORATION
To: ARIZONA CHEMICAL COMPANY LLC
Reel/Frame 037451/0057 →
RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY COLLATERAL AT REEL/FRAME NO. 33146/0361 Recorded Jan 6, 2016
From: GOLDMAN SACHS BANK USA
To: ARIZONA CHEMICAL COMPANY LLC
Reel/Frame 037451/0169 →
CORRECTIVE ASSIGNMENT TO CORRECT THE PATENT NUMBER 8837224 TO PATENT NUMBER 7737224 PREVIOUSLY RECORDED AT REEL: 037448 FRAME: 0453. ASSIGNOR(S) HEREBY CONFIRMS THE SECURITY INTEREST. Recorded Jan 6, 2016
From: KRATON POLYMERS U.S. LLC; ARIZONA CHEMICAL COMPANY, LLC
To: BANK OF AMERICA, N.A.
Reel/Frame 037448/0453 →
ASSIGNMENT OF INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Oct 9, 2015
From: GENERAL ELECTRIC CAPITAL CORPORATION, AS RETIRING AGENT
To: ANTARES CAPITAL LP, AS SUCCESSOR AGENT
Reel/Frame 036827/0443 →
RELEASE OF SECURITY INTEREST Recorded Jun 12, 2014
From: GENERAL ELECTRIC CAPITAL CORPORATION, AS COLLATERAL AGENT
To: ARIZONA CHEMICAL COMPANY LLC
Reel/Frame 033146/0278 →
SECURITY INTEREST Recorded Jun 12, 2014
From: ARIZONA CHEMICAL COMPANY LLC
To: GENERAL ELECTRIC CAPITAL CORPORATION, AS FIRST LIEN COLLATERAL AGENT
Reel/Frame 033146/0333 →
SECURITY INTEREST Recorded Jun 12, 2014
From: ARIZONA CHEMICAL COMPANY LLC
To: GOLDMAN SACHS BANK USA, AS SECOND LIEN COLLATERAL AGENT
Reel/Frame 033146/0361 →
SECURITY AGREEMENT Recorded Jan 7, 2012
From: ARIZONA CHEMICAL COMPANY, LLC
To: GENERAL ELECTRIC CAPITAL CORPORATION, AS COLLATERAL AGENT
Reel/Frame 027497/0465 →
RELEASE OF SECURITY INTEREST Recorded Jan 6, 2012
From: GENERAL ELECTRIC CAPITAL CORPORATION
To: ARIZONA CHEMICAL COMPANY, LLC
Reel/Frame 027489/0030 →
SECURITY AGREEMENT Recorded Feb 2, 2011
From: ARIZONA CHEMICAL COMPANY, LLC
To: GENERAL ELECTRIC CAPITAL CORPORATION, AS COLLATERAL AGENT
Reel/Frame 025734/0383 →
RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY COLLATERAL (FIRST LIEN) Recorded Jan 31, 2011
From: GOLDMAN SACHS CREDIT PARTNERS, L.P.
To: ARIZONA CHEMICAL COMPANY
Reel/Frame 025719/0265 →
RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY COLLATERAL (SECOND LIEN) Recorded Jan 31, 2011
From: WILMINGTON TRUST FSB (SUCCESSOR TO CAPITALSOURCE FINANCE LLC)
To: ARIZONA CHEMICAL COMPANY
Reel/Frame 025720/0248 →
CHANGE OF NAME Recorded Nov 24, 2010
From: ARIZONA CHEMICAL COMPANY
To: ARIZONA CHEMICAL COMPANY, LLC
Reel/Frame 025406/0597 →
CHANGE OF NAME Recorded Aug 30, 2010
From: CAPITALSOURCE FINANCE LLC
To: WILMINGTON TRUST FSB
Reel/Frame 024944/0501 →
FIRST LIEN PATENT SECURITY AGREEMENT Recorded Mar 20, 2007
From: ARIZONA CHEMICAL COMPANY
To: GOLDMAN SACHS CREDIT PARTNERS, L.P.
Reel/Frame 019035/0392 →
SECOND LIEN PATENT SECURITY AGREEMENT Recorded Mar 20, 2007
From: ARIZONA CHEMICAL COMPANY
To: CAPITAL SOURCE FINANCE, LLC
Reel/Frame 019035/0423 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 22, 2003
From: PAVLIN, MARK S.
To: ARIZONA CHEMICAL COMPANY
Reel/Frame 014123/0174 →