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JP-7855708-B2 - Stable liquid crosslinking agent composition for heat-curable inks

JP7855708B2JP 7855708 B2JP7855708 B2JP 7855708B2JP-7855708-B2

Inventors

  • ビルストランド，チャールズ，アーサー
  • フォロッソ，アレクサンダー

Assignees

  • アイエヌエックス インターナショナル インク カンパニー

Dates

Publication Date
20260508
Application Date
20220303

Claims (19)

  1. A crosslinking agent compound of formula (I), wherein R1 , R2 , and R3 are each independent C1-10 alkyl groups, (I) Hydroxy-functional polymers and It comprises a non-volatile diluent having a boiling point of 145°C to 200°C, in an amount of 5% to 35% by weight of the ink vehicle composition , An ink vehicle composition that is substantially free of butanol and water .
  2. The ink vehicle composition according to claim 1, wherein R1 , R2 , and R3 are each independent C1-4 alkyl groups.
  3. The ink vehicle composition according to claim 1, wherein the crosslinking agent compound is in an amount of 10 % to 90% by weight of the ink vehicle composition.
  4. The ink vehicle composition according to claim 1, wherein the hydroxy-functional polymer is selected from the group consisting of hydroxy-functional polyester, hydroxy-functional polyacrylic, hydroxy-functional polyurethane, and combinations thereof.
  5. The ink vehicle composition according to claim 1, wherein the hydroxy- functional polymer is present in an amount of 20 % to 80% by weight of the ink vehicle composition.
  6. The ink vehicle composition according to claim 1, wherein the non-volatile diluent is selected from the group consisting of hydrocarbons, glycols, polyalkylene glycols, polyesters, and combinations thereof.
  7. The ink vehicle composition according to claim 1, having a viscosity of 200 to 500 poise.
  8. The ink vehicle composition according to claim 1, wherein the ink vehicle composition is stable at room temperature for 6 to 24 months.
  9. The ink vehicle composition according to claim 1, wherein R1 , R2 , and R3 are each independently methyl or n-butyl, the hydroxy-functional polymer is a hydroxy-functional polyester, and the non-volatile diluent is a polyalkylene glycol .
  10. A method for preparing an ink vehicle composition, A crosslinking agent compound of formula (I), in which R1 , R2 , and R3 are each independent C1-10 alkyl groups, is dissolved and mixed with butanol, a hydroxy-functional polymer, and a non-volatile diluent having a boiling point of 145°C to 200°C to form a mixture. (I) A method comprising the step of evaporating at least 98% of the butanol from the mixture to provide the ink vehicle composition according to claim 1.
  11. The method according to claim 10 , wherein the evaporation comprises heating the mixture at a temperature of 65 °C under a pressure of 20 mmHg (torr) or less.
  12. (a) The ink vehicle composition according to claim 1, (b) A thermosetting heat-curing ink comprising a colorant.
  13. The thermosetting heat-curable ink according to claim 12 , wherein the thermosetting heat-curable ink is stable at room temperature for at least six months.
  14. The thermosetting heat-curable ink according to claim 12 , wherein the ink vehicle composition is in an amount of 30 % to 60% by weight of the thermosetting heat-curable ink.
  15. The thermosetting heat-curable ink according to claim 12 , wherein the coloring agent is in an amount of 10 % to 60 % by weight of the thermosetting heat-curable ink.
  16. The thermosetting heat -curable ink according to claim 12 , further comprising a lubricant, viscosity modifier, tack modifier, flow modifier, surfactant, diluent, or a combination thereof.
  17. A method for printing ink onto a substrate, A step of applying the thermosetting heat-curable ink described in claim 12 to the surface of the substrate, A method comprising the step of curing the applied thermosetting heat-curable ink by heating the applied thermosetting heat-curable ink.
  18. The method according to claim 17 , wherein the surface is a metal surface.
  19. The method according to claim 17 , wherein the base material is a container.

Description

This disclosure relates to a stable composition containing a 1,3,5-triazinecarbamate (TACT) crosslinking agent and a method for preparing the same, for use, for example, in high-speed offset printing of thermosetting inks. TACT compounds are trifunctional melamine-based crosslinking agents possessing reactive carbamate functional groups. TACT crosslinking agents are solid materials requiring dissolution in a solvent. They do not dissolve in polyether glycol-based solvents, and commercially available TACT crosslinking agents are typically supplied as a 50-52% solution in n-butanol. However, due to the boiling point of butanol, TACT butanol solutions cannot achieve suitable printing properties for high-speed offset printing of thermosetting (heat-curable) ink formulations. Furthermore, during storage, evaporation of butanol can cause the solid crosslinking agent to precipitate from the ink, potentially interfering with the printing process. This disclosure provides a liquid crosslinking agent composition comprising a TACT crosslinking agent compound. The liquid crosslinking agent composition is particularly suitable for use in the preparation of curable compositions such as high-solids content coating compositions, overprint varnishes, printable inks, and other related applications. Furthermore, the TACT crosslinking agent process does not release or generate formaldehyde. In the case of heat-curable inks, the TACT crosslinking agent can be mixed with a hydroxy-functional polymer and a non-volatile diluent to form a thermosetting composition, which can be used as an ink vehicle composition for the preparation of printable inks. The crosslinking agent compositions and inks described herein may remain stable for extended periods at room temperature without crosslinking, solid precipitation, or stratification of components. Therefore, this disclosure provides a formaldehyde-free, heat-curable, printable ink that may be useful for printing images on hard surfaces such as metal surfaces of containers. (1. Definition) The terms “comprise(s),” “include(s),” “having,” “has,” “can,” “contain(s),” and their variations as used herein are intended to be open-ended conjunctions, terms, or words that do not preclude the possibility of additional acts or structures. The singular forms “a,” “an,” and “the” include plural references unless explicitly stated otherwise in the context. This disclosure also intends to include other embodiments “comprise,” “consisting of,” and “consisting essentially of” the embodiments or elements presented herein, whether expressly provided or not. The modifier "approximately" used in relation to quantities encompasses the stated value and has a meaning indicated by the context (for example, at least including the degree of error associated with the measurement of a particular quantity). It is desirable to consider the modifier "approximately" as disclosing a range defined by the absolute values of the two endpoints. For example, the expression "approximately 2 to approximately 4" also discloses the range "approximately 2 to approximately 4". The term "approximately" can sometimes refer to plus or minus 10% of the given number. For example, "approximately 10%" may indicate a range of 9% to 11%, and "approximately 1" may mean 0.9 to 1.1. Other meanings of "approximately" may be clear from the context, such as rounding; for example, "approximately 1" may also mean 0.5 to 1.4. In this specification, numerical ranges are explicitly intended to include numbers with similar precision intervening within them. For example, the range 6–9 includes 6, 9, 7, and 8, while the range 6.0–7.0 explicitly includes 6.0, 6.1, 6.2, 6.3, 6.4, 6.5, 6.6, 6.7, 6.8, 6.9, and 7.0. As used herein, the term "alkyl" means a linear or branched saturated hydrocarbon chain containing 1 to 20 carbon atoms. The terms "lower alkyl" or " C1-6 alkyl" mean a linear or branched hydrocarbon chain containing 1 to 6 carbon atoms. Representative examples of alkyls include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, 3-methylhexyl, 2,2-dimethylpentyl, 2,3-dimethylpentyl, n-heptyl, n-octyl, n-nonyl, and n-decyl. In one embodiment, the number of carbon atoms in an alkyl group is indicated by the prefix "C x-y " or "C x - C y- ", where x is the minimum number of carbon atoms in the substituent and y is the maximum number. Therefore, for example, "C 1-4 alkyl" or "C 1 -C 4 -alkyl" refers to an alkyl substituent containing one to four carbon atoms. The term "butanol" refers to n-butanol, which has the formula CH3 ( CH2 ) 3OH . The term "cure" or "curing" refers to the process that results in the curing and/or crosslinking of a hydroxy-functional polymer with other hydroxy-functional polymers, within the same polymer, or in combination thereof. Furthermore, depending on whether the non-volatile diluent has functional groups that can react with the