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United States Patent (19) (11) Patent Number: 5,145,997 Schwartz Et Al

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United States Patent (19) (11) Patent Number: 5,145,997 Schwartz Et Al USOO5145997A United States Patent (19) (11) Patent Number: 5,145,997 Schwartz et al. (45) Date of Patent: Sep. 8, 1992 54 POLY (ALKYLENE OXIDE) SUBSTITUTED (57) ABSTRACT ACETOACETANILDES Poly (alkylene oxide) substituted acetoacetanilides of the formula: 75 Inventors: Russell J. Schwartz, Cincinnati; Anthony C. Zwirgzdas, Butler; Terence R. Chamberlain, Cincinnati, R all of Ohio O O (73) Assignee: Sun Chemical Corporation, Fort Lee, NH-C-CH2-c-CH3 N.J. - X-B d (21) Appl. No.: 654,163 wherein B comprises a divalent bridging moiety se 22 Filed: Feb. 12, 1991 lected from the group consisting of C1-C6 alkylene, -NHSO2-, -O-, -CO-, -COO-, and -N- 51) Int. Cl. ................... CO7C 235/84; CO7C 311/37 CHO-; X comprises a poly (alkylene oxide) having a number average molecular weight of about 200 to 52 U.S. C. .................................... 564/158; 534/561; 10,000; R comprises 0 to 4 moieties independently se 560/20, 560/21; 560/142; 564/82; 564/86; lected from the group consisting of C1-C4 alkyl, C1-C4 564/153; 564/200 alkoxy and halogen; and d is an integer of 1 to 3. The 58 Field of Search ................... 564/153, 58, 82, 86, poly (alkylene oxide) substituted acetoacetanilides are 564/200,534/561; 560/21, 22, 142 prepared by reacting a poly (alkylene oxide) mono (56) References Cited amine, diamine or triamine with isatoic anhydride fol lowed by acetoacetylation of the resultant aminobenza U.S. PATENT DOCUMENTS mide. The substituted acetoacetanilides are useful for 3,984,460 10/1976 Spivack . preparing improved diarylide pigment compositions 4,118,382 10/1978 J?ger et al. .......................... 260/154 which in turn are useful for preparing storage stable printing inks (especially of the publication gravure Primary Examiner-Richard L. Raymond type). Assistant Examiner-P. O'Sullivan Attorney, Agent, or Firm-Jack Matalon 8 Claims, No Drawings 5,145,997 1 2 POLY (ALKYLENE OXIDE) SUBSTITUTED -continued ACETOACETANLEDES fH, FIELD OF THE INVENTION 5 CH3-O-CH-CH to-CH-CH-NH; + This invention relates to novel poly (alkylene oxide) substituted acetoacetanilides and to processes for pre poly (alkylene oxide) monoamine paring such acetoacetanilides. These acetoacetanilides have been found to be useful for preparing improved diarylide pigment compositions which in turn are useful 10 for preparing storage stable printing inks (especially of the publication gravure type). DESCRIPTION OF THE INVENTION The present invention is directed to poly (alkylene 15 isatoic anhydride oxide) substituted acetoacetanilides having the general formula: Hs CH3-O-CH-CH p-CH-CH-NH-c - CO2 R 20 O O HN NH-C-CH-C-CH3 substituted monoaminobenzamide ("K") XH-B d 25 Step B wherein B comprises a divalent bridging moiety se lected from the group consisting of C1-C6 alkylene, -- -NHSO2-, -O-, -COO-, and -NHCO-; X K+...H2C=C-O ii-> comprises a poly (alkylene oxide) having a number 30 average molecular weight of about 200 to 10,000; R diketene comprises Oto 4 moieties independently selected from the group consisting of C1-C4 alkyl, C1-C4 alkoxy and halogen; and d is an integer of 1 to 3. Preferably, the Hs poly (alkylene oxide) has a number average molecular 35 CH3-O-CH2-CH-O-CH2-CH-NH-C weight of 1,000 to 3,000, R is equal to 0 moieties, d is an integer of 1, and B is -CONH-. It is particularly preferred that the poly (alkylene CH3-C-CH2-C-N oxide) be an ethylene oxide/propylene oxide copoly O O H. mer, especially those copolymers embraced by the for mula: poly (alkylene oxide) substituted acetoacetanilide ("L') Acetoacetylation (Step B) may also be performed H. using t-butylacetoacetate instead of diketene, as indi CH3 O-CH2-CH O-CH2-CH 45 cated below. Although the use of t-butylacetoacetate as the acetoacetylation agent leads to the production of wherein Q is H or CH3 and w is an integer of about 4 to t-butanol as a by-product, it is nevertheless preferred for 200, preferably 20 to 65. manufacturing purposes since diketene is considered The novel poly (alkylene oxide) substituted hazardous to transport and handle. acetoacetanilides of the present invention can be readily SO prepared by the steps of CH3 O O Step A: reacting a poly (alkylene oxide) monoamine, poly (alkylene oxide) diamine or poly (alkylene K. -- CH-i-o--CH.--CH, - G oxide) triamine with a reactant comprisingisatoic ss th anhydride (at a temperature of 20' to 130 C) so as to obtain the respective mono, bis, or tris amino CH3 benzamide-terminated poly (alkylene oxide); and L - ch,--oh Step B: acetoacetylating the substituted aminobenza mide obtained in Step A with an acetoacetylation th. agent comprising diketene or t-butylacetoacetate The poly (alkylene oxide) amines employed in Step A so as to produce the poly (alkylene oxide) substi are well known and are commercially available, e.g. as tuted acetoacetanilide. Jeffamines (R), manufactured by Texaco Chemical Com The process for preparing the poly (alkylene oxide) pany. These amines contain a polyether backbone that is substituted acetoacetanilide may be illustrated as fol- 65 based either on propylene oxide ethylene oxide or lows: mixed propylene oxide and ethylene oxide. The poly (alkylene oxide) monoamines are prepared by reaction Step A of a monohydric alcohol, followed by conversion of the 5,145,997 3 4. resulting terminal hydroxyl group to an amine. The poly (alkylene oxide) diamines are commercially avail able as several types, e.g. diamine-terminated polypro SH: Y Y SH: pylene glycols, polyether diamines based on a predomi nantly polyethylene oxide backbone as well as urea o= (=o condensates of such polyether diamines. Useful poly (alkylene oxide) triamines are those prepared by reac o= EO tion of propylene oxide with a triol, followed by amina H-N N-H tion of the terminal hydroxyl groups. For the purposes of the present invention, the poly (alkylene oxide) 10 monoamines are preferred. Further details of the prepa ration of poly (alkylene oxide) amines and their proper ties may be found in the Technical Service Bulletin Rn Rp published by the Texaco Chemical Company, entitled "The Jeffamine (R) Polyoxyalkyleneamines". 15 wherein R and R' are independently selected from the The poly (alkylene oxide) substituted acetoaceta group consisting of C1-C4 alkyl, C1-C4 alkoxy and halo nildes are useful for preparing diarylide pigments which gen; n and p are independently integers of 0 to 5; and Y exhibit excellent storage stability in aromatic solvent is Cl, CH3 or OCH3. For the purposes of the present based printing inks, e.g. publication gravure inks. The invention, the preferred pigments to be improved using diarylide pigment may be of any of the know types 20 the present poly (alkylene oxide) substituted derived from the well known reactions involving (1) acetoacetanilides are Pigment Yellow 12, Pigment Yel tetrazotizing 3,3'-dichlorobenzidine or dianisidine with low 13, Pigment Yellow 14, Pigment Yellow 17, Pig nitrous acid (which in turn is typically generated by the ment Yellow 83, Pigment 114, Pigment Yellow 126, combination of sodium nitrite and hydrochloric acid) Pigment Yellow 127, Pigment Yellow 176, and Pigment and (2) the coupling of the resultant tetrazonium salt 25 Orange 16. The following reactions are illustrative of with an acetoacetanilide. A typical diarylide pigment the manner in which the poly (alkylene oxide) substi will have the following structure. tuted acetoacetanilide corresponding to compound "L' may be employed to prepare an improved version of Pigment Yellow 12: Cl C s(O) (O) NH2 + 2(NaNO2) + 4HCl - G C C C- "(O) (O) Cl + 2NaCl + 4H2O C C O O I NH-C-CH2-C-CH3+ L +Cl- NEN HCl re H. O. H. O. I N-c-f-c-ch, N I N C 5,145,997 -continued Pigment Yellow 12 N N N-C-C-C-CH3 H. O. H. O. Plus Compound "M" plus Compound "N” shown hereinbelow: tuted acetoacetanilides of the present invention exhibit H. O. H. O. Compound "M" outstanding storage stability, showing no discernible changes in color shade, strength or rheology, even after N-c-f-c-ch, prolonged storage at elevated temperatures (over 3 N days at 50 C.). Furthermore, the elimination of mal odorous amines from the formulations provides an in N proved manufacturing environment for both the pig ment and ink producer. C The following nonlimiting examples serve to illus trate the poly (alkylene oxide) substituted acetoacetani lides and their method of preparation as well as their use in preparing improved diarylide pigments and storage stable publication gravure inks prepared from such improved diarylide pigments. Unless otherwise indi cated, all parts and percentage are by weight. Cl EXAMPLE I N Agent A: A mixture of 16.5 parts ofisatoic anhydride H. O. N. O. (96% pure) and 220 parts of a primary amine-terminated poly (ethylene oxide/propylene oxide) copolymer hav N-C-CH-C-CH3 ing a number average molecular weight of approxi C-N-CH-CH-O mately 2,000 (sold and Jeffamine (R) M 2070 by Texaco Chemical Corp.) was stirred and heated gradually to O H CH3 g-a-la.Q 80 C. until evolution of CO2 ceased. The infrared spec trum indicated that the isatoic anhydride had com Compound "N" pletely reacted as evidenced by the disappearance of the Hs | characteristic anhydride absorptions at 1748 cm-land C-N-CH-CH-O CH-CH-O CH3 1787 cm and the appearance of an amide absorption at approximately 1640 cm-1. Thereafter, 8.4 parts of diketene were added and stirring continued at 80 C. for Hi O N O about 1 hour until all the diketene had reacted as evi denced by the disappearance of its characteristic infra N red absorptions at 1891 cm31 and 1860 cm3 1.
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