Analytical aspects and film properties of two-pack acetoacetate functional latexes

Synthesis of a low‐temperature self‐crosslinking polyacrylate binder with a core‐shell structure and its application in textile pigment printing

“…In water‐based systems such as those based on acrylic latex polymers, the AcAc moiety in AAEM can exhibit hydrolytic stability problems, especially at elevated temperatures . Another problem which can affect these systems is precrosslinking . Both these phenomena negatively influence the film properties of the latex.…”

Synthesis of a low‐temperature self‐crosslinking polyacrylate binder with a core‐shell structure and its application in textile pigment printing

“…In water‐based systems such as those based on acrylic latex polymers, the AcAc moiety in AAEM can exhibit hydrolytic stability problems, especially at elevated temperatures . Another problem which can affect these systems is precrosslinking . Both these phenomena negatively influence the film properties of the latex.…”

The stability of enamine crosslinks formed from acetoacetate/amine in synthetic hydrogels

“…In aqueous media, enamine formation is often inefficient and the equilibrium enamine concentration is sensitive to solution conditions [35,38,40,41,49,50]. Nishihata et al described the equilibrium formation of enamine from phenylalanine and ethyl acetoacetate in water in the pH range from 7 to 10 [41].…”

“…In some cases, these polymers have been prepared or employed in aqueous media where hydrolysis might pose a potential problem during extended exposure. Hydrolysis has been recognized as a concern for the acetoacetate-functional methacrylate copolymers used in the latex or coatings industry [35,38,43,44], however, hydrolysis appears to be slower in these systems, probably because of the more hydrophobic nature, and hence low water content, of the emulsion copolymer particles. In contrast, the water-soluble A70 is much more susceptible to hydrolysis.…”

Hard Coatings from Soft Latexes: A Review of Routes to Overcome the Film Formation Dilemma

“…Usually, the diketo functionalities are incorporated into the polymer particles copolymerizing acetoacetoxyethyl methacrylate (AAEMA, Figure 14A1), acetetoacetamido methacrylate (AAMMA, Figure 14A2), or diacetone acrylamide (DAAM Figure 14A3) and they are subsequently crosslinked employing water-soluble polyamines or polyhydrazides (Figure 14B1,C). [171][172][173][174][175][176][177][178] The main drawback of acetoacetoxy chemistry is the water sensitivity of this functionality, which decomposes in humid conditions to form a hydroxyethyl moiety, acetone, and CO 2 (Figure 14B2). [163] This issue can be largely avoided by reversibly protecting the acetoacetoxy groups with ammonium after the synthesis (Figure 14B3).…”

Synthesis of a low‐temperature self‐crosslinking polyacrylate binder with a core‐shell structure and its application in textile pigment printing

“…In water‐based systems such as those based on acrylic latex polymers, the AcAc moiety in AAEM can exhibit hydrolytic stability problems, especially at elevated temperatures . Another problem which can affect these systems is precrosslinking . Both these phenomena negatively influence the film properties of the latex.…”

The stability of enamine crosslinks formed from acetoacetate/amine in synthetic hydrogels

“…In aqueous media, enamine formation is often inefficient and the equilibrium enamine concentration is sensitive to solution conditions [35,38,40,41,49,50]. Nishihata et al described the equilibrium formation of enamine from phenylalanine and ethyl acetoacetate in water in the pH range from 7 to 10 [41].…”

“…In some cases, these polymers have been prepared or employed in aqueous media where hydrolysis might pose a potential problem during extended exposure. Hydrolysis has been recognized as a concern for the acetoacetate-functional methacrylate copolymers used in the latex or coatings industry [35,38,43,44], however, hydrolysis appears to be slower in these systems, probably because of the more hydrophobic nature, and hence low water content, of the emulsion copolymer particles. In contrast, the water-soluble A70 is much more susceptible to hydrolysis.…”

Hard Coatings from Soft Latexes: A Review of Routes to Overcome the Film Formation Dilemma

“…Usually, the diketo functionalities are incorporated into the polymer particles copolymerizing acetoacetoxyethyl methacrylate (AAEMA, Figure 14A1), acetetoacetamido methacrylate (AAMMA, Figure 14A2), or diacetone acrylamide (DAAM Figure 14A3) and they are subsequently crosslinked employing water-soluble polyamines or polyhydrazides (Figure 14B1,C). [171][172][173][174][175][176][177][178] The main drawback of acetoacetoxy chemistry is the water sensitivity of this functionality, which decomposes in humid conditions to form a hydroxyethyl moiety, acetone, and CO 2 (Figure 14B2). [163] This issue can be largely avoided by reversibly protecting the acetoacetoxy groups with ammonium after the synthesis (Figure 14B3).…”

Synthesis of a low‐temperature self‐crosslinking polyacrylate binder with a core‐shell structure and its application in textile pigment printing

“…In water‐based systems such as those based on acrylic latex polymers, the AcAc moiety in AAEM can exhibit hydrolytic stability problems, especially at elevated temperatures . Another problem which can affect these systems is precrosslinking . Both these phenomena negatively influence the film properties of the latex.…”

The stability of enamine crosslinks formed from acetoacetate/amine in synthetic hydrogels

“…In aqueous media, enamine formation is often inefficient and the equilibrium enamine concentration is sensitive to solution conditions [35,38,40,41,49,50]. Nishihata et al described the equilibrium formation of enamine from phenylalanine and ethyl acetoacetate in water in the pH range from 7 to 10 [41].…”

“…In some cases, these polymers have been prepared or employed in aqueous media where hydrolysis might pose a potential problem during extended exposure. Hydrolysis has been recognized as a concern for the acetoacetate-functional methacrylate copolymers used in the latex or coatings industry [35,38,43,44], however, hydrolysis appears to be slower in these systems, probably because of the more hydrophobic nature, and hence low water content, of the emulsion copolymer particles. In contrast, the water-soluble A70 is much more susceptible to hydrolysis.…”

Hard Coatings from Soft Latexes: A Review of Routes to Overcome the Film Formation Dilemma

“…Usually, the diketo functionalities are incorporated into the polymer particles copolymerizing acetoacetoxyethyl methacrylate (AAEMA, Figure 14A1), acetetoacetamido methacrylate (AAMMA, Figure 14A2), or diacetone acrylamide (DAAM Figure 14A3) and they are subsequently crosslinked employing water-soluble polyamines or polyhydrazides (Figure 14B1,C). [171][172][173][174][175][176][177][178] The main drawback of acetoacetoxy chemistry is the water sensitivity of this functionality, which decomposes in humid conditions to form a hydroxyethyl moiety, acetone, and CO 2 (Figure 14B2). [163] This issue can be largely avoided by reversibly protecting the acetoacetoxy groups with ammonium after the synthesis (Figure 14B3).…”