US 11,753,528 B2
Endcapped curable polyorganosiloxanes
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 Nov. 6, 2020, as Appl. No. 17/91,269.
Application 17/091,269 is a continuation of application No. PCT/EP2019/062837, filed on May 17, 2019.
Claims priority of application No. 18173234 (EP), filed on May 18, 2018; application No. 18194659 (EP), filed on Sep. 14, 2018; and application No. 18209573 (EP), filed on Nov. 30, 2018.
Prior Publication US 2021/0054148 A1, Feb. 25, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C08G 77/26 (2006.01); C08K 5/544 (2006.01); C08L 83/04 (2006.01); C09D 183/04 (2006.01); C09J 183/04 (2006.01); C09K 3/10 (2006.01); C08G 77/12 (2006.01); C08G 77/08 (2006.01); C08G 77/16 (2006.01); C08G 77/18 (2006.01); C08G 77/20 (2006.01); C08G 77/24 (2006.01); C08G 77/28 (2006.01); C08K 5/5465 (2006.01); C08K 5/57 (2006.01); C08L 83/06 (2006.01)
CPC C08K 5/544 (2013.01) [C08G 77/08 (2013.01); C08G 77/12 (2013.01); C08G 77/16 (2013.01); C08G 77/18 (2013.01); C08G 77/20 (2013.01); C08G 77/24 (2013.01); C08G 77/26 (2013.01); C08G 77/28 (2013.01); C08K 5/5465 (2013.01); C08K 5/5477 (2021.01); C08K 5/57 (2013.01); C08L 83/04 (2013.01); C08L 83/06 (2013.01); C09D 183/04 (2013.01); C09J 183/04 (2013.01); C09K 3/1018 (2013.01); C08G 2170/00 (2013.01); C08G 2190/00 (2013.01); C08L 2312/08 (2013.01)] 17 Claims
 
1. A 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, alkoxy, alkenyl, alkenyloxy, alkynyl, alkylnyloxy, cycloaliphatic, cycloaliphatic-O—, aryl, aryloxy, heteroaryl, heteroaryloxy, heteroalicyclic, heteroalicyclicoxy, acyl, acyloxy group and 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 and aryl group; and
o 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 and 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 and a combination thereof;
each R10 is independently selected from the group consisting of a substituted or unsubstituted alkyl, alkenyl, alkynyl, and 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;
wherein said polyorganosiloxane is obtained by reacting a polyorganosiloxane (Ia) having at least one reactive group A′ bound to a silicon atom with a compound of formula (Ib)
C—Si(R1)m(R2)n(R3)3−(m+n)  (Ib)
with C being a reactive group that reacts with the at least one reactive group A′ bound to a silicon atom to yield the linking group -A- in the presence of a compound of formula (Ic) as a catalyst
D-R11—SiR12q(OR13)3−q  (Ic)
wherein
R11 is an alkylene group, optionally interrupted by a heteroatom;
each R12 is independently selected from the group consisting of hydrogen, halogen, amino, a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloaliphatic, aryl, heteroaryl, and heteroalicyclic group and a combination thereof;
each R13 is independently selected from the group consisting of a substituted or unsubstituted alkyl, alkenyl, alkynyl, and acyl group;
q independently stands for 0, 1, or 2; and
D is a nitrogen-containing group selected from the group of formula (Id), (Ie) or (If)

OG Complex Work Unit Chemistry
wherein each R14 is independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloaliphatic, aryl, heteroaryl, and heteroalicyclic group and a combination thereof;
each R14a, R14b, R14c, R15 and R16 is independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloaliphatic, aryl, heteroaryl, and heteroalicyclic group and a combination thereof; and
r is 1, 2, 3 or 4.