Aziridinosilicones and the use thereof
View Patent ↗Arizidinosilicones of the general formula (1), wherein R1 represents H, C1-C12 alkyl, C2-C12 alkenyl, C2-C12 alkinyl, C7-C15 alkaryl, C7-C15 aralkyl, C3-C12 cycloalkyl and these groups can be substituted with Cl or F partially, completely or in a mixed manner and/or may contain 0 to 5 heteroatoms selected from O, N, S, R2 represents a group of the selection of R1 and/or R4, and R3 represents SiRl3 or SiR12R4, and wherein R4 represents formula (2), and A represents an (n+1) radical saturated, unsaturated or aromatic, linear, branched or cyclic hydrocarbon group that may contain 0 to 5 heteroatoms selected from O, N, S and that includes 1 to 18 carbon atoms, B is selected from O, S, NR1, D is selected from C(O)O, C(O)NR1, C(O), C(O)C(O), C(O)(CH2)m(C(O), C(S)NR1, CH2, E represents a diradical saturated or unsaturated, linear, branched or cyclic hydrocarbon group that may contain 0 to 5 heteroatoms selected from O, N, S and that includes 0 to 18 carbon atoms, a is 0 or 1, f is an integer from 2 to 1000, n, m is an integer from 1 to 10, and x, y, z each represents 0 or an integer, the sum of which should range between 1 and 10000, with the proviso that, if x is larger 0, y or z is smaller or equal x, preferably smaller or equal 0.05 times x, and especially preferred 0.02 times x. The invention also relates to the use of arizidinosilicones.
1. An N-alkylaziridinosilicone of the formula:
wherein:
R1=H, C 1 -C 12 -alkyl, C 2 -C 12 -alkenyl, C 2 -C 12 -alkynyl, C 7 -C 15 -alkaryl, C 7 -C 15 -aralkyl or C 3 -C 12 -cycloalkyl, and these radicals may be substituted partially, fully or in a mixed manner by Cl or F and/or may contain from 0 to 5 heteroatoms from the group consisting of O, N and S;
R2=a radical from the selection of R1 and/or R4; and
R3=SiR1 3 or SiR1 2 R4;
wherein R4=
and
A=an (n+1)-valent saturated, unsaturated or aromatic, linear, branched or cyclic hydrocarbon radical, which may contain from 0 to 5 heteroatoms from the group consisting of O, N and S and comprises from 1 to 18 carbon atoms;
B=selected from the group consisting of O, S and NR1;
D=selected from the group consisting of C(O)O, C(O)NR1, C(O), C(O)C(O), C(O)(CH 2 ) m (C(O), C(S)NR1 and CH 2 ;
E=a divalent saturated or unsaturated, linear, branched or cyclic hydrocarbon radical, which may contain from 0 to 5 heteroatoms from the group consisting of O, N and S and comprises from 0 to 18 carbon atoms;
a=0 or 1;
f=an integer from 2 to 1000;
n and m=an integer from 1 to 10; and
x, y and z are each either 0 or integers whose sum is between 1 and 10,000;
wherein if x is greater than 0, y or z are less than or equal to x.
2. The N-alkylaziridinosilicone of claim 1 , wherein if x is greater than 0, y or z are less than or equal to 0.05 times x.
3. The N-alkylaziridinosilicone of claim 1 , wherein if x is greater than 0, y or z are less than or equal to 0.02 times x.
4. A curable material based on N-alkylaziridinosilicone of claim 1 , which, after mixing of the components, comprises, based on 100 parts by weight:
(A) from 30 to 97 parts by weight of at least one N-alkylaziridino block copolymer having molecular weights in the range from 500 to 50,000 g/mol and aziridino equivalent weights in the range from 250 to 25,000 g/equivalent,
(B) from 1 to 10 parts by weight of starter substances which are suitable for effecting curing of the N-alkylaziridino block copolymers,
(C) from 1 to 35 parts by weight of organic diluents, and
(D) from 1 to 50 parts by weight of modifiers.
5. A two-component dental material comprising the base component of claim 1 and a catalyst component, where the material produced by homogeneous mixing of the catalyst component and the base component has a pot life at room temperature of between about 0.5 and about 10 minutes, and the material cures within a period of from about 1 to about 20 minutes at a temperature in the range from about 23 to about 36° C. to give an elastically deformable material having a Shore A hardness of at least 20.
6. The N-alkylaziridinosilicone of claim 1 , comprising an N-alkyl aziridinosilicone having from 1 to 10 N-alkylaziridino groups per molecule, where the N-alkylaziridinosilicone has a molecular weight in the range from 500 to 50,000 g/mol.
7. The curable material of claim 4 , wherein said organic diluents comprise organopolysiloxanes having polyalkylene oxide blocks that conform to the following formulae:
where:
Q=an α,ω-valent polyether chain of the formula (3):
—[O—C g H 2g ] h — (3);
wherein
R5=OH, OR1, O—C(O)—R1 or O—C(O)—NHR1;
g=from 2 to 20;
h=from 1 to 1000;
p=an integer from 1 to 1000;
q=an integer from 1 to 50; and
r=an integer from 1 to 1000.
8. The curable material of claim 4 , wherein said starter substances comprise trisalkylsulfonium salts.
9. The curable material of claim 4 , wherein said starter substances comprise Brönsted acids.
10. The curable material of claim 9 , wherein the Brönsted acids acidity has been reduced by antiacids.
11. The curable material of claim 4 , wherein starter substances comprise at least one boric acid complex.
12. A process of using the N-alkylaziridinosilicone of claim 1 comprising preparing a curable material.
13. A process of using the N-alkylaziridinosilicone of claim 1 comprising preparing a dental material.
14. A process of using the N-alkylaziridinosilicone of claim 1 comprising bonding, coating, or encapsulating substrates.
15. The process of claim 14 , further comprising using dental impression materials, bite registration materials, modeling materials, temporary filling materials, materials for the production of temporary crowns and bridges, and duplicating materials.
16. A containing at least the N-alkylaziridinosilicone of claim 1 .
17. A containing at least the curable material of claim 4 .
18. A containing at least the dental material of claim 5 .