US 11,912,801 B2
(Meth)acrylate urethane (urea) phosphonates as adhesion promoters
Ying Lin, Woodbury, MN (US); Sheng Ye, Woodbury, MN (US); Thomas P. Klun, Woodbury, MN (US); Semra Colak Atan, St. Louis Park, MN (US); and Jerald K. Rasmussen, Woodville, WI (US)
Assigned to 3M Innovative Properties Company, St. Paul, MN (US)
Appl. No. 17/271,134
Filed by 3M INNOVATIVE PROPERTIES COMPANY, St. Paul, MN (US)
PCT Filed Aug. 21, 2019, PCT No. PCT/US2019/047374
§ 371(c)(1), (2) Date Feb. 24, 2021,
PCT Pub. No. WO2020/046654, PCT Pub. Date Mar. 5, 2020.
Claims priority of provisional application 62/724,837, filed on Aug. 30, 2018.
Prior Publication US 2021/0253765 A1, Aug. 19, 2021
Int. Cl. C08F 222/10 (2006.01); C08F 2/50 (2006.01); C08K 5/08 (2006.01); C08K 5/5313 (2006.01); C08K 5/5393 (2006.01); C08K 5/5397 (2006.01); C09J 4/00 (2006.01)
CPC C08F 222/1065 (2020.02) [C08F 2/50 (2013.01); C08K 5/08 (2013.01); C08K 5/5313 (2013.01); C08K 5/5393 (2013.01); C08K 5/5397 (2013.01); C09J 4/00 (2013.01)] 14 Claims
 
1. A curable composition comprising:
a multifunctional urethane (meth)acrylate oligomer, wherein the multifunctional urethane (meth)acrylate oligomer is of the general formula:

OG Complex Work Unit Chemistry
wherein
Z is an ethylenically unsaturated, free radical polymerizable group,
RISO is the residue of a polyisocyanate having at least two of its—NCO groups reacted to form a urethane bonding Z to ROH, subscript a is 0 or 1, b is 2-6, and
ROH is the residue of a polyol having at least a+b hydroxyl groups and a number average molecular weight between 90 and 10,000, the residue formed by removal of hydrogen from the hydroxyl groups;
optionally a reactive diluent;
an initiator;
a multifunctional (meth)acrylate crosslinker containing no urethane functional groups; and
an adhesion promoter of the formula:

OG Complex Work Unit Chemistry
wherein
R1 is H or C1-C4 alkyl
R2 and R3 are each independently a (hetero)hydrocarbyl group;
R5 is H or C1-C4 alkyl;
X1 is -O- or -NR4-, where R4 is H or C1-C4 alkyl,
subscript x is 1 or 2; and
subscript y is 1 or 2;
wherein the curable composition comprises 0.1 pbw to about 10 pbw of the multifunctional (meth)acrylate crosslinker based on 100 pbw of the total polymerizable components of the composition.