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( 12 ) United States Patent US010259953B2 (12 ) United States Patent ( 10 ) Patent No. : US 10 , 259 ,953 B2 Wu et al. (45 ) Date of Patent: Apr. 16 , 2019 ( 54 ) ADHESION PROMOTED AND INK (58 ) Field of Classification Search COMPOSITION None See application file for complete search history . (71 ) Applicant: BORICA CO ., LTD ., Taipei ( TW ) (72 ) Inventors : Cheng - En Wu , Taipei (TW ) ; (56 ) References Cited Chun -Han Shih , Taipei ( TW ) ; U . S . PATENT DOCUMENTS Shu -Han Lee , Taipei ( TW ) ; Fu -Ming 4 , 931, 094 A 6 / 1990 Barfurth et al. Tsuo , Taipei ( TW ) 5 ,021 , 596 A * 6 / 1991 Barfurth .. .. CO7F 7 /003 106 / 31. 69 ( 73 ) Assignee : BORICA CO ., LTD ., Taipei ( TW ) 5 , 897 ,694 A * 4 / 1999 Woolf .. .. .. .. CO9D 11 / 36 106 /31 . 27 ( * ) Notice : Subject to any disclaimer , the term of this 7 ,619 , 021 B2 11/ 2009 Duncan patent is extended or adjusted under 35 8 , 722 , 811 B2 5 /2014 Duncan et al . U . S . C . 154 (b ) by 0 days . 9 ,034 , 958 B2 5 / 2015 Mielke et al. 9 , 139 ,716 B2 9 /2015 Crandon et al. ( 21 ) Appl. No .: 15 /673 ,409 9 ,279 ,034 B2 3 / 2016 Mielke et al . (22 ) Filed : Aug . 9 , 2017 OTHER PUBLICATIONS Hagedorn Nitrocellulose Product Information . ( Year: 2018 ). * (65 ) Prior Publication Data Lindsley and Frank , Industrial and Engineering Chemistry , 45( 11) , US 2018 / 0094147 A1 Apr. 5 , 2018 1953, 2491- 2497 . ( Year : 1953 ). * Related U . S . Application Data * cited by examiner (60 ) Provisional application No. 62/ 401 , 905, filed on Sep . 30 , 2016 . Primary Examiner — Vu A Nguyen (74 ) Attorney, Agent, or Firm — CKC & Partners Co ., (51 ) Int. Cl. LLC CO9D 11 /03 (2014 .01 ) C08K 5 / 00 ( 2006 .01 ) (57 ) ABSTRACT C09D 11 /033 ( 2014 .01 ) C09D 11 /037 ( 2014 .01 ) An ink composition and an adhesion promoter are provided . CO9D 11 /08 ( 2006 .01 ) The adhesion promoter is suitable for production while CO9D 11 / 102 ( 2014 .01 ) remaining the stronger adhesion . The adhesion promoter is C08G 85 /00 (2006 . 01 ) formed by the reaction of at least one alpha hydroxy acid and C09D 11 / 10 ( 2014 .01 at least one alpha hydroxy acid ester with the metal alkoxide . C09D 11/ 14 ( 2006 . 01) More specifically , by combining the renewable and green CO9D 11 / 104 ( 2014 .01 ) alpha hydroxy acid and safer plasticizing alpha hydroxy acid C08K 5 / 11 ( 2006 .01 ) ester as reagent to react with the metal alkoxide, the eco C08K 5 / 101 ( 2006 .01 ) friendly and non - toxic adhesion promoter with superior (52 ) U . S . CI. adhesion for use in ink composition can be obtained . The ink CPC .. CO9D 11 / 03 ( 2013 . 01) ; C08G 85 / 004 composition includes the adhesion promoter, a pigment, a ( 2013 .01 ) ; C09D 11/ 033 ( 2013 . 01 ) ; C09D polymeric binder, and a solvent for the polymeric binder. 11/ 037 ( 2013 .01 ) ; C09D 11 /08 ( 2013 .01 ) ; The ink composition is odorless and colorless , and shows C09D 11 / 10 ( 2013 . 01 ) ; C09D 11 / 102 good wet crinkle resistance . Especially , the ink composition (2013 . 01 ) ; C09D 11 / 104 ( 2013 . 01 ) ; CO9D is suitable for printing on the food package . 11/ 14 ( 2013 .01 ) ; C08K 5 / 0091 ( 2013 .01 ) ; C08K 5 / 101 ( 2013 .01 ) ; C08K 5 / 11 (2013 . 01 ) 12 Claims, No Drawings US 10 , 259 ,953 B2 ADHESION PROMOTED AND INK In some embodiments , the tartaric acid ester has a formula COMPOSITION of C2H (OH ) 2 (COOR . ) ( COOR10 ) , R , and R10 are indepen dently H atom or C2 to C alkyl group , and one of R , and R10 CROSS - REFERENCE TO RELATED is an alkyl group . APPLICATION 5 In some embodiments , the citric acid ester has a formula of C2H4OH ( COOR11) (COOR12 ) (COOR13 ) , R11 , R12 and This application claims priority to U . S . Provisional Appli - R13 are independently H atom or C2 to Co alkyl group , and cation Ser. No. 62/ 401 , 905, filed Sep . 30 , 2016 , which is one of R11 , R12 and R13 is an alkyl group . In some embodiments , the mixture further comprises herein incorporated by reference. 10 water. BACKGROUND In some embodiments , the mixture has a carboxylic acid number of from about 50 mg KOH / g to about 400 mg Field of Invention KOH / g . In some embodiments , a ratio of a totalmole of the at least 15 one alpha hydroxy acid and the at least one alpha hydroxy The present invention relates to an ink composition and an acid ester to a mole of the metal alkoxide is 0 . 2 to 4 : 1 . adhesion promoter. More particularly , the present invention The present disclosure provides an ink composition . The relates to an ink composition and an adhesion promoter for ink composition includes a pigment , a polymeric binder , a use in ink composition , wherein the adhesion promoter solvent for the polymeric binder , and an adhesion promoter includes a reaction product of a metal alkoxide and a mixtureture 20 incincluding a reaction product of a metal alkoxide and a of at least one alpha hydroxy acid and at least one alpha mixture of at least one alpha hydroxy acid and at least one hydroxy acid ester . alpha hydroxy acid ester . The metal alkoxide has a formula of M (OR ) (OR ) ( ORB) (OR4 ) , wherein M is titanium , zirco Description of Related Art nium , or aluminum , and R1 , R2, Rz, and R4 are indepen 25 dently C , to C , alkyl group . The alpha hydroxy acid is Adhesion promoters have long been used in inks to selected from the group consisting of glycolic acid , lactic promote adhesion properties to enable the inks to adhere to acid , malic acid , tartaric acid , and citric acid . The alpha a variety of substrates and thus meet requirements of cus hydroxy acid ester is selected from the group consisting of tomers and end - users . glycolic acid ester, lactic acid ester , malic acid ester , tartaric However , in some printing ink formulation processes , 30 acid ester, and citric acid ester . adhesion promoters such as titanium acetylacetonates tend In some embodiments , the adhesion promoter is present at to impart undesirable by - products to the ink . These by - a concentration of from 1 % to 20 % by weight , based on the products may have undesired yellow color and odor and thus total weight of the ink composition . adversely influence the resulting inks . Moreover , the toxic In some embodiments , the polymeric binder has at least acetylacetone derivative ingredient is not suitable for being 35 one functional group selected from the group consisting of printed on food package due to potential migration problem . hydroxyl group ( OH ) , amino group ( NH2) , carboxyl Based on above, it is required adhesion promoters with group ( COOH ), cyanate group ( NCO ) , and ester group . superior adhesion and safety to satisfy the current industrial These and other features , aspects , and advantages of the needs. present invention will become better understood with refer 40 ence to the following description and appended claims. SUMMARY It is to be understood that both the foregoing general description and the following detailed description are by The present disclosure provides an adhesion promoter . examples , and are intended to provide further explanation of The adhesion promoter includes a reaction product of a the invention as claimed . metal alkoxide and a mixture of at least one alpha hydroxy 45 acid and at least one alpha hydroxy acid ester . More spe DETAILED DESCRIPTION cifically , by combining the renewable and green alpha hydroxy acid and safer plasticizing alpha hydroxy acid ester The use of examples anywhere in this specification as reagent to react with the metal alkoxide , the eco - friendly including examples of any terms discussed herein is illus and non -toxic adhesion promoter with superior adhesion for 50 trative only , and in no way limits the scope and meaning of use in ink composition can be obtained . The metal alkoxide the invention or of any exemplified term . Likewise , the has a formula of M (OR ) (OR ) (OR3 ) ( OR4) , wherein M is invention is not limited to various embodiments given in this titanium , zirconium , or aluminum , and R , R2, Rz , and R . specification . are independently C , to C , alkyl group . The alpha hydroxy Unless otherwise defined , all terms ( including technical acid is selected from the group consisting of glycolic acid , 55 and scientific terms) used herein have the same meaning as lactic acid , malic acid , tartaric acid , and citric acid . The commonly understood by one of ordinary skill in the art to alpha hydroxy acid ester is selected from the group consist - which this invention belongs. It will be further understood ing of glycolic acid ester, lactic acid ester, malic acid ester, that terms, such as those defined in commonly used diction tartaric acid ester, and citric acid ester . aries , should be interpreted as having a meaning that is In some embodiments , the glycolic acid ester has a 60 consistent with their meaning in the context of the relevant formula of CH2OH (COOR3 ) , and R , is C , to Coalkyl group . art and the present disclosure, and will not be interpreted in In some embodiments , the lactic acid ester has a formula an idealized or overly formal sense unless expressly so of C2H4OH (COOR . ) , and R . is C2 to C , alkyl group . defined herein . In some embodiments , the malic acid ester has a formula The terminology used herein is for the purpose of describ ofC2H2OH (COOR , ) (COOR ) , R , and Rg are independently 65 ing particular embodiments only and is not intended to be H atom or C , to Coalkyl group , and one of R , and Rg is an limiting of the invention . As used herein , the singular forms alkyl group . “ a , " " an ” and “ the ” are intended to include the plural forms US 10 , 259 , 953 B2 as well , unless the context clearly indicates otherwise .
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