	US 11,708,428 B2
	Photopolymerizable compositions including a polyurethane methacrylate polymer prepared using a polycarbonate diol, articles, and methods
Thomas P. Klun, Lakeland, MN (US); Zeba Parkar, Marietta, GA (US); John M. Riedesel, San Jose, CA (US); Richard J. Pokorny, Maplewood, MN (US); Chad M. Amb, Roberts, WI (US); Benjamin R. Coonce, South St. Paul, MN (US); Robert S. Clough, St. Paul, MN (US); Tianyu Wu, St. Paul, MN (US); Saswata Chakraborty, Cottage Grove, MN (US); Yongshang Lu, Woodbury, MN (US); and Benjamin C. MacMurray, St. Paul, MN (US)
Assigned to 3M Innovative Properties Company, St. Paul, MN (US)
Filed by 3M INNOVATIVE PROPERTIES COMPANY, St. Paul, MN (US)
Filed on Jun. 10, 2021, as Appl. No. 17/344,096.
Application 17/344,096 is a continuation of application No. 17/042,243, granted, now 11,225,535, previously published as PCT/US2019/033241, filed on May 21, 2019.
Claims priority of provisional application 62/769,434, filed on Nov. 19, 2018.
Claims priority of provisional application 62/736,027, filed on Sep. 25, 2018.
Claims priority of provisional application 62/692,466, filed on Jun. 29, 2018.
Prior Publication US 2021/0301042 A1, Sep. 30, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C08F 2/46 (2006.01); C08F 2/50 (2006.01); C08G 61/04 (2006.01); B33Y 10/00 (2015.01); B33Y 30/00 (2015.01); B33Y 70/00 (2020.01); B29C 64/129 (2017.01); C08F 2/44 (2006.01); C08F 220/18 (2006.01); C08F 290/06 (2006.01); C08G 18/44 (2006.01); C08G 18/67 (2006.01); C08K 5/00 (2006.01); C08K 5/3437 (2006.01)

CPC C08F 2/50 (2013.01) [B29C 64/129 (2017.08); B33Y 10/00 (2014.12); B33Y 30/00 (2014.12); B33Y 70/00 (2014.12); C08F 2/44 (2013.01); C08F 220/18 (2013.01); C08F 290/06 (2013.01); C08G 18/44 (2013.01); C08G 18/672 (2013.01); C08K 5/0041 (2013.01); C08K 5/3437 (2013.01)]

22 Claims

1. A photopolymerizable composition comprising:

a) 40-60 parts by weight of a monofunctional (meth)acrylate monomer, per 100 parts of the total photopolymerizable composition, wherein a cured homopolymer of the monofunctional (meth)acrylate monomer has a T_gof 125° C. or greater;

b) a photoinitiator; and

c) a polymerization reaction product of components, the components comprising:

i) a diisocyanate;

ii) a hydroxy functional methacrylate of Formula (I):

HO-Q-(A)_p (I)

wherein Q is a polyvalent organic linking group, A is a methacryl functional group of the formula —OC(═O)C(R₁)═CH₂, wherein R₁is a lower alkyl of 1 to 4 carbon atoms, and wherein p is 1 or 2; and

iii) a polycarbonate diol of Formula (II):

H(O—R₂—O—C(═O))_m—O—R₃—OH (II)

wherein each of R₂in each (O—R₂—O—C(═O)) repeat unit, and R₃are independently an aliphatic, cycloaliphatic, or aliphatic/cycloaliphatic alkylene group and an average number of carbon atoms in a combination of all the R₂and R₃groups is 4 to 10, and m is 2 to 23; and

iv) a catalyst;

wherein the polymerization reaction product comprises a polyurethane methacrylate polymer having a weight average molecular weight (Mw) of 8,000 g/mol or greater and wherein the photopolymerizable composition contains 11% by weight or less of any monofunctional (meth)acrylate monomer having a log P value of less than 3, less than 2, or less than 1, based on the total weight of the photopolymerizable composition.