Hydroxyurethane (meth)acrylate prepolymers for use in 3d printing
AssigneeBASF SE
InventorsAndre FUCHS, Rolf MUELHAUPT, Anne Cathrin ASMACHER, Vitalij SCHIMPF
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Abstract
The present invention relates to prepolymers of formula (I), a process for the production of the prepolymers, photocurable compositions, comprising the prepolymers of formula (I) and their use in a photopolymerization 3D printing process. In contrast to usual urethane (meth)acrylates. The prepolymers of formula (I) can be prepared without using toxic isocyanates and exhibit pending hydroxyl groups along their molecule backbone which allow for the introduction of further side chains or side groups to improve, for example, the interaction with inorganic fillers.
Claims18
A prepolymer of formula
- wherein
- X1 is a linking group, or a group of formula
- X1′ is a linking group;
- X2 is independently in each occurrence a group of formula —CH(CH2OH)—, or —CH(OH)—(CH2)—,
- R1, R2 and R3 are independently of each other H, or a C1-C4-alkyl group;
- n1 is an integer of 1 to 12;
- m is an integer of 1 to 4;
- wherein optionally the hydrogen atom of the hydroxy groups and/or the amino groups of the prepolymer may be replaced by a group of formula
- wherein
- R4, R5 and R6 are independently of each other H, or a C1-C4-alkyl group;
- R7 is a C1-C25alkyl group, a C2-C25alkenyl group, or a phenyl group, which can be substituted by one, or more C1-C8alkyl groups, C1-C8alkoxy groups,
- R14 is a group of formula —SiR15(R16)2,
- R15 is a C1-C8alkoxy group,
- R16 is a C1-C8alkyl group, or a C1-C8alkoxy group,
- n2 is an integer of 1 to 12;
- and
- n3 and n4 are an integer of 1 to 12.
A process for the production of a prepolymer, comprising
- a) reacting a cyclic carbonate of formula
- with a polyamine of formula (H2N)mX1 (III), or reacting a digycidylethercarbonate of formula
- with a polyamine of formula (III) and the obtained reaction product with a cyclic carbonate of formula (II), wherein
- R1, R2 and R3 are independently of each other H, or a C1-C4-alkyl group;
- n1 is an integer of 1 to 12;
- m is an integer of 1 to 4;
- X1 is a linking group,
- X5 is a linking group,
- m5 is an integer of 1 to 12.
Dependencies are inferred from the claim text.