US 12,421,421 B2
Composition including a polyorganosiloxane and an amino-functional silane and method of using the same
Audrey A. Eigner, White Bear Lake, MN (US); Jon P. Nietfeld, Woodbury, MN (US); Chad M. Amb, Roberts, WI (US); Steven J. McMan, Stillwater, MN (US); Ara Z. Nercissiantz, Los Angeles, CA (US); Allison E. Strong, Warrenville, IL (US); John A. Luekemeyer, Jurupa Valley, CA (US); and Derrick Tarn, Santa Ana, CA (US)
Assigned to 3M Innovative Properties Company, St. Paul, MN (US)
Appl. No. 17/632,189
Filed by 3M INNOVATIVE PROPERTIES COMPANY, St. Paul, MN (US)
PCT Filed Jul. 30, 2020, PCT No. PCT/IB2020/057227
§ 371(c)(1), (2) Date Feb. 1, 2022,
PCT Pub. No. WO2021/024118, PCT Pub. Date Feb. 11, 2021.
Claims priority of provisional application 63/016,366, filed on Apr. 28, 2020.
Claims priority of provisional application 62/955,913, filed on Dec. 31, 2019.
Claims priority of provisional application 62/882,289, filed on Aug. 2, 2019.
Prior Publication US 2022/0267640 A1, Aug. 25, 2022
Int. Cl. C09D 183/04 (2006.01); C08G 77/18 (2006.01); C08K 5/5415 (2006.01); C08K 5/544 (2006.01); C08K 5/5445 (2006.01)
CPC C09D 183/04 (2013.01) [C08G 77/18 (2013.01); C08K 5/5415 (2013.01); C08K 5/544 (2013.01); C08K 5/5445 (2021.01)] 30 Claims
 
1. A composition comprising:
a first polyorganosiloxane comprising divalent units represented by formula:

OG Complex Work Unit Chemistry
and greater than two —Si(Y)p(R)3-p groups,
wherein the first polyorganosiloxane comprises (m) terminal units represented by formula —Q—Si(Y)p(R)3-p and (n) divalent units represented by formula:

OG Complex Work Unit Chemistry
wherein
each R is independently alkyl, aryl, arylalkylenyl, or heterocycloalkylenyl, wherein alkyl and arylalkylenyl are unsubstituted or substituted with halogen and optionally interrupted by at least one catenated —O—, —S—, —N(R11)—, or combination thereof, wherein aryl, arylalkylenyl, and heterocycloalkyenyl are unsubstituted or substituted by at least one alkyl, alkoxy, halogen, or combination thereof, and wherein R11 is hydrogen, alkyl, aryl, or arylalkylenyl, wherein aryl and arylalkylenyl are unsubstituted or substituted by at least one alkyl, alkoxy, or combination thereof;
each Q is independently a bond, alkylene, arylene, or alkylene that is at least one of interrupted or terminated by aryl, wherein the alkylene, arylene, and alkylene that is at least one of interrupted or terminated by aryl are optionally at least one of interrupted or terminated by at least one ether, thioether, amine, amide, ester, thioester, carbonate, thiocarbonate, carbamate, thiocarbamate, urea, thiourea, or a combination thereof;
each Y is independently a hydrolyzable group;
p is 1, 2, or 3;
(n) is at least 1; and
(m)+(n) is in a range from 3 to 6; and
at least one of
an amino-functional silane represented by formula (R6)2N—[R4—Z]r—R4—[Si(Y)p(R5)3-p] or a cyclic azasilane represented by formula

OG Complex Work Unit Chemistry
wherein
each R4 is independently alkylene, arylene, or alkylene optionally interrupted or terminated by arylene;
R5 is alkyl, aryl, arylalkylenyl, or heterocycloalkylenyl, wherein aryl and arylalkylenyl are unsubstituted or substituted by at least one alkyl, alkoxy, or combination thereof;
each Z is independently —O— or —N(R6)—;
each R6 is independently hydrogen, alkyl, aryl, arylalkylenyl, or —R4—[Si(Y)p(R5)3-p], wherein aryl and arylalkylenyl are unsubstituted or substituted by at least one alkyl, alkoxy, or combination thereof;
R7 is an alkylene having 2 to 5 carbon atoms and is uninterrupted or interrupted by at least one catenated —N(R8)—;
each R8 is independently hydrogen, alkyl, or alkenyl, wherein alkyl and alkenyl are unsubstituted or substituted by —NR1R2, wherein R1 and R2 are independently hydrogen or alkyl;
each Y is independently a hydrolyzable group;
r is 0, 1, 2, or 3; and
p is 1, 2, or 3,
wherein when the composition is applied to a surface of a substrate and at least partially cured to form a coated surface, the coated surface has a receding deionized water contact angle of greater than 80 after 500 scrubs using the Panel Scrub Method.