Sulfur-containing oligomer and dendrimer of acrylate and preparation methods thereof
Sulfur-containing oligomer and dendrimer of acrylate and preparation methods thereof are provided. The sulfur-containing oligomer and dendrimer of acrylate are prepared by reacting monomers A and B in Michael addition reaction.
1. A sulfur-containing acrylate oligomer having a chemical structure of B 1 -A 2 -B 1 , wherein A 2 and B 1 respectively have chemical structures below:
and wherein R 1 , R 4 , R 5 and R 6 are respectively an alkyl group with 1-6 carbons, and R 2 and R 3 are respectively an aromatic or a cycloalkyl group.
2. The sulfur-containing acrylate oligomer of claim 1 , wherein the R 2 and the R 3 respectively have a chemical structure of
3. The sulfur-containing acrylate oligomer of claim 1 , wherein the R 1 and R 4 are respectively a straight chain alkyl group having 1-4 carbons.
4. The sulfur-containing acrylate oligomer of claim 1 , wherein the R 5 and R 6 are respectively a straight chain alkyl group having 2, 4, or 6 carbons.
5. The sulfur-containing acrylate oligomer of claim 1 , wherein A 2 is
6. The sulfur-containing acrylate oligomer of claim 1 , wherein B 1 is
7. A modified sulfur-containing acrylate oligomer having a chemical structure of B 1 ′-A 2 -B 1 ′, B 1 ′-A 2 -B 1 ″ or B 1 ″-A 2 -B 1 ″, wherein A 2 , B 1 ′ and B 1 ″ respectively have the chemical structures below:
and wherein R 1 , R 4 , R 5 and R 6 are respectively an alkyl group with 1-6 carbons, R 2 and R 3 are respectively an aromatic or a cycloalkyl group, and R 7 is an aromatic group or a heterocyclic group having at least a double bond.
8. A method of preparing a sulfur-containing acrylate oligomer, the method comprising:
dropwise adding a monomer A into an aprotic solvent containing a monomer B to perform Michael addition to obtain a sulfur-containing acrylate oligomer, wherein the molar ratio of A to B is 1:2, and A and B respectively have chemical structures below:
wherein the sulfur-containing acrylate oligomer having a chemical structure of B 1 -A 2 -B 1 , wherein A 2 and B 1 respectively have chemical structures below, and R 1 , R 4 , R 5 and R 6 are respectively an alkyl group with 1-6 carbons, and R 2 and R 3 are respectively an aromatic or a cycloalkyl group.
9. The method of claim 8 , further comprising adding a catalyst to the aprotic solvent to catalyze the Michael addition.
10. A method of preparing a modified sulfur-containing acrylate oligomer, the method comprising:
dropwise adding a monomer A into an aprotic solvent containing a monomer B to perform Michael addition to obtain a sulfur-containing acrylate oligomer, wherein the molar ratio of A to B is 1:2, and A and B respectively have chemical structures below:
wherein the sulfur-containing acrylate oligomer having a chemical structure of B 1 -A 2 -B 1 , wherein A 2 and B 1 respectively have chemical structures below, and R 1 , R 4 , R 5 and R 6 are respectively an alkyl group with 1-6 carbons, and R 2 and R 3 are respectively an aromatic or a cycloalkyl group; and
adding a thiol-containing modifier (R 7 SH) to perform Michael addition with the sulfur-containing acrylate oligomer to obtain a modified sulfur-containing acrylate oligomer having a chemical structure of B 1 ′-A 2 -B 1 ′, B 1 ′-A 2 -B 1 ′, or B 1 ″-A 2 -B 1 ″, wherein B 1 ′ and B 1 ″ respectively have the chemical structures below, and R 7 is an aromatic group or a heterocyclic group having at least a double bond.
11. A sulfur-containing acrylate dendrimer having a chemical structure of
wherein B 1 and B 2 are randomly distributed on terminals of the sulfur-containing acrylate dendrimer, and the chemical structures of A 2 , B 1 , B 2 and B 3 are shown below:
and wherein R 1 , R 4 , R 5 and R 6 are respectively an alkyl group with 1-6 carbons, and R 2 and R 3 are respectively an aromatic or a cycloalkyl group.
12. The sulfur-containing acrylate dendrimer of claim 11 , wherein the R 2 and the R 3 respectively have a chemical structure of
13. The sulfur-containing acrylate dendrimer of claim 11 , wherein the R 1 and R 4 are respectively a straight chain alkyl group having 1-4 carbons.
14. The sulfur-containing acrylate dendrimer of claim 11 , wherein the R 5 and R 6 are respectively a straight chain alkyl group having 2, 4, or 6 carbons.
15. The sulfur-containing acrylate dendrimer of claim 11 , wherein A 2 is
16. The sulfur-containing acrylate dendrimer of claim 11 , wherein B 1 , B 2 and B 3 are
respectively.
17. A modified sulfur-containing acrylate dendrimer having a chemical structure of
wherein A 2 , B 1 ′, B 1 ″, B 2 ′ and B 3 respectively have chemical structures below:
and wherein R 1 , R 4 , R 5 and R 6 are respectively an alkyl group with 1-6 carbons, R 2 and R 3 are respectively an aromatic or a cycloalkyl group, and R 7 is an aromatic group or a heterocyclic group having at least a double bond.
18. A method of preparing a sulfur-containing acrylate dendrimer, the method comprising:
reacting a monomer A and a monomer B in an aprotic solvent to obtain a sulfur-containing acrylate dendrimer having a chemical structure of
wherein B 1 and B 2 are randomly distributed on terminals of the sulfur-containing acrylate dendrimer, wherein the molar ratio of monomer A to monomer B is 1:0.25-4, but not 1:2 when the monomer A is added to the aprotic solvent containing the monomer B, and the monomer A, monomer B, A 2 , B 1 , B 2 and B 3 respectively have chemical structures below:
wherein R 1 , R 4 , R 5 and R 6 are respectively an alkyl group with 1-6 carbons, and R 2 and R 3 are respectively an aromatic or a cycloalkyl group.
19. The method of claim 18 , further comprising adding a catalyst to the aprotic solvent to catalyze the reaction.
20. A method of preparing a modified sulfur-containing acrylate dendrimer, the method comprising:
reacting a monomer A and a monomer B in an aprotic solvent to obtain a sulfur-containing acrylate dendrimer having a chemical structure of
wherein B 1 and B 2 are randomly distributed on terminals of the sulfur-containing acrylate dendrimer, wherein the molar ratio of monomer A to monomer B is 1:0.25-4, but not 1:2 when the monomer A is added to the aprotic solvent containing the monomer B, and the monomer A, monomer B, A 2 , B 1 , B 2 and B 3 respectively have chemical structures below:
wherein R 1 , R 4 , R 5 and R 6 are respectively an alkyl group with 1-6 carbons, and R 2 and R 3 are respectively an aromatic or a cycloalkyl group; and
adding a thiol-containing modifier (R 7 SH) to perform Michael addition with the sulfur-containing acrylate dendrimer to obtain a modified sulfur-containing acrylate dendrimer having a chemical structure of
wherein B 1 ′, B 1 ″, and B 2 ′ respectively have chemical structures below:
and wherein R 7 is an aromatic group or a heterocyclic group having at least a double bond.