US 12,466,921 B2
Curable silicone compositions containing additives
Therese Hemery, Wiesbaden (DE); Helene Boudet, Hilden (DE); and Johann Klein, Duesseldorf (DE)
Assigned to Henkel AG & Co. KGaA, Duesseldorf (DE)
Filed by Henkel AG & Co. KGaA, Duesseldorf (DE)
Filed on May 26, 2021, as Appl. No. 17/330,546.
Application 17/330,546 is a continuation of application No. PCT/EP2019/082170, filed on Nov. 22, 2019.
Claims priority of application No. 18209561 (EP), filed on Nov. 30, 2018.
Prior Publication US 2021/0292487 A1, Sep. 23, 2021
Int. Cl. C08L 83/06 (2006.01); C08G 77/14 (2006.01); C08G 77/18 (2006.01); C08G 77/26 (2006.01); C08G 77/388 (2006.01); C08K 5/544 (2006.01); C08K 13/02 (2006.01); C09D 183/08 (2006.01); C09J 183/08 (2006.01)
CPC C08G 77/14 (2013.01) [C08G 77/18 (2013.01); C08G 77/26 (2013.01); C08G 77/388 (2013.01); C08K 5/544 (2013.01); C08K 13/02 (2013.01); C08L 83/06 (2013.01); C09D 183/08 (2013.01); C09J 183/08 (2013.01)] 19 Claims
 
1. 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.