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US 12,466,921 B2Granted
Curable silicone compositions containing additives
AssigneeHenkel AG & Co. KGaA
InventorsTherese Hemery, Helene Boudet, Johann Klein
Life of this patent
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Abstract
The invention relates to curable compositions based on polyorganosiloxanes with special silicon-containing terminal groups, an adhesion promoter, a curing catalyst, and an additive having a ketone functional moiety. These compositions have improved mechanical and adhesion properties and excellent storage stability. The invention also relates to the uses thereof.
Claims19
A curable composition comprising (A) at least one polyorganosiloxane containing at least one terminal group of the formula (I):
- -A-Si(R1)m(R2)n(R3)3−(m+n) (I)
- wherein:
- A is a bond, —O— or a linear, branched or cyclic divalent group selected from hydrocarbon residues having 1 to 12 carbon atoms, alkylene, arylene, oxyalkylene, oxyarylene, siloxane-alkylene, siloxane-arylene, ester, amine, glycol, imide, amide, alcohol, carbonate, urethane, urea, sulfide, ether or a derivative or combination thereof;
- each R1 is independently selected from the group consisting of hydrogen, halogen, amino, oximino, a substituted or unsubstituted alkyl, alkenyl, alkenyloxy, alkynyl, alkylnyloxy, cycloaliphatic, cycloaliphatic-O—, aryl, aryloxy, heteroaryl, heteroaryloxy, heteroalicyclic, heteroalicyclicoxy, acyl, acyloxy group or a combination thereof;
- each R2 is independently a group of the general formula (2):
- —O—Y—COOR4 (2)
- wherein
- Y is a substituted or unsubstituted (hetero)aromatic group having 4 to 14 ring atoms, a substituted or unsubstituted saturated or partially unsaturated 4- to 14-membered (hetero)cyclic group or —(C(R5)2)o—;
- R4 is a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloaliphatic, aryl, heteroaryl, and heteroalicyclic group or a combination thereof;
- each R5 is independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloaliphatic or aryl group;
- and
- is an integer from 1 to 10;
- each R3 independently is a group of the general formula (3):
- —O—Y—CONR6R7 (3)
- wherein
- Y is as defined above;
- R6 is selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl, alkenyl, alkynyl cycloaliphatic, aryl, heteroaryl, and heteroalicyclic group or a combination thereof or R7;
- R7 is a group of the general formula (4):
- —R8—SiR9p(OR10)3-p (4)
- wherein
- R8 is an alkylene group, optionally interrupted by a heteroatom;
- each R9 is independently selected from the group consisting of hydrogen, halogen, amino, a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloaliphatic, aryl, heteroaryl, and heteroalicyclic group or a combination thereof;
- each R10 is independently selected from the group consisting of a substituted or unsubstituted alkyl, alkenyl, alkynyl, or acyl group;
- each p independently stands for 0, 1, or 2;
- m is independently 0, 1 or 2;
- and
- n is independently 1, 2, or 3, wherein the sum n+m is a maximum of 3;
- (B) at least one adhesion promoter;
- (C) at least one curing catalyst;
- (D) at least one additive having an aldehyde functional moiety of formula (III)
- R31—C(═O)—R32 (III)
- wherein
- R31 is a substituted or unsubstituted C6-14 aryl;
- and
- R32 is hydrogen,
- wherein the additive of formula (III) comprises up to 24 carbon atoms:
- (E) at least one plasticizer;
- and
- (F) at least one filler,
- wherein the composition exhibits a decreased skin-over time and an increased elongation at break directly after mixing, and after storage for 8 weeks at 40° C. and 80% humidity, relative to an otherwise equivalent composition that does not comprise the at least one additive (D) and wherein the composition is room temperature curable.
37 more elements
Dependencies are inferred from the claim text.