Acetoacetylated Alcohols

A process of manufacturing an acetoacetylated alcohol, the process comprising the step of reacting an alcohol of formula (20)

• in the presence of a catalyst (C1) with diketene, wherein
• R10 is H, OH, C1-C10-alkyl, C1-C10-haloalkyl, C1-C10-alkoxy, C2-C10-alkenyl, C2-C10-alkynyl, C3-C10-cycloalkyl, C3-C10-cycloalkenyl, C3-C10-aryl, C3-C10-aryloxy, or ORA;
• Z is within each unit independently C1-C10-alkylene, C2-C10-alkenylene, C2-C10-alkynylene, C3-C10 bivalent aryl, C(O)—C3-C10-aryl-C(O), C1-C10-alkylene-C3-C10-aryl-C1-C10-alkylene, or C3-C10-aryl-C1-C10-alkylene-C3-C10-aryl, wherein each carbon atom of the aforementioned substituents may independently be unsubstituted or substituted with one or more same of different of RB;
• within each unit independently x and y are either both CH or x is C and y is not present so that the respective unit corresponds to a spiro cyclic moiety of formula (SC)
• m is independently 0, 1, or 2;
• n is independently 0, 1, or 2;
• wherein within one unit when y is not present at least one of m or n is 1;
• p is an integer of 1 to 6;
• RA is a moiety of formula (A-1) or formula (A-2)
• wherein
• RN is independently H, halogen, or C1-C3-alkyl;
• RM is C1-C6-alkyl or C1-C6-haloalkyl;
• RB is halogen, C1-C6-alkyl, or C1-C6-alkoxy;
• t is 0 or an integer of 1 to 10000;
• and
• q is 0 or an integer of 1 to 6.

A composition comprising a compound of formula (10)

• wherein
• R10 is H, OH, C1-C10-alkyl, C1-C10-haloalkyl, C1-C10-alkoxy, C2-C10-alkenyl, C2-C10-alkynyl, C3-C10-cycloalkyl, C3-C10-cycloalkenyl, C3-C10-aryl, C3-C10-aryloxy, or ORA;
• Z is within each unit independently C1-C10-alkylene, C2-C10-alkenylene, C2-C10-alkynylene, C3-C10 bivalent aryl, C(O)—C3-C10-aryl-C(O), C1-C10-alkylene-C3-C10-aryl-C1-C10-alkylene, or C3-C10-aryl-C1-C10-alkylene-C3-C10-aryl, wherein each carbon atom of the aforementioned substituents may independently be unsubstituted or substituted with one or more same of different of RB;
• within each unit independently x and y are either both CH or x is C and y is not present so that the respective unit corresponds to a spiro cyclic moiety of formula (SC)
• m is independently 0, 1, or 2;
• n is independently 0, 1, or 2;
• wherein within one unit when y is not present at least one of m or n is 1;
• p is an integer of 1 to 6;
• RA is a moiety of formula (A-1) or formula (A-2)
• wherein
• RN is independently H, halogen, or C1-C3-alkyl;
• RM is C1-C6-alkyl or C1-C6-haloalkyl;
• R8 is halogen, C1-C6-alkyl, or C1-C6-alkoxy;
• t is O or an integer of 1 to 10000;
• and
• q is O or an integer of 1 to 6,
• and an additive (A) selected from the group consisting of catalyst (C2), reinforcement fibres, a filler, compounds comprising at least one α,β-unsaturated carbonyl group, epoxies, vinyl compounds, oxetanes, amines, isocyanates, and combinations thereof.

A 3D printing resin composition comprising a compound of formula (10a)

• wherein
• R10 is H, OH, C1-C10-alkyl, C1-C10-haloalkyl, C1-C10-alkoxy, C2-C10-alkenyl, C2-C10-alkynyl, C3-C10-cycloalkyl, C3-C10-cycloalkenyl, C3-C10-aryl, C3-C10-aryloxy, or ORA;
• Z is within each unit independently C1-C3-alkylene, wherein each carbon atom of the aforementioned substituents may independently be unsubstituted or substituted with one or more same of different of RB;
• within each unit independently x and y are either both CH or x is C and y is not present so that the respective unit corresponds to a spiro cyclic moiety of formula (SC)
• m is independently 0, 1, or 2;
• n is independently 0, 1, or 2;
• wherein within one unit when y is not present at least one of m or n is 1;
• p is an integer of 1 to 6;
• RA is a moiety of formula (A-1) or formula (A-2)
• wherein
• RN is independently H, halogen, or C1-C3-alkyl;
• RM is C1-C6-alkyl or C1-C6-haloalkyl;
• R8 is halogen, C1-C6-alkyl, or C1-C6-alkoxy;
• t is O or an integer of 1 to 10000;
• and
• q is O or an integer of 1 to 6.