	US 12,247,134 B2
	Coating compositions
Brian L. Conley, Longmont, CO (US); Shengxi Li, Arcadia, CA (US); Nathan A. Mason, Inglewood, CA (US); Madhura M. Pade, Pasadena, CA (US); Wenliang P. Yang, Ballston Lake, NY (US); John H. Phillips, Los Angeles, CA (US); Brian Edgecombe, Anaheim, CA (US); Kristina Goulinian, Glendale, CA (US); and Jenny Parchen, Arcadia, CA (US)
Assigned to MATERIA, INC., Pasadenia, CA (US)
Appl. No. 17/311,495
Filed by MATERIA, INC., Pasadena, CA (US)
PCT Filed Dec. 13, 2019, PCT No. PCT/US2019/066239 § 371(c)(1), (2) Date Jun. 7, 2021, PCT Pub. No. WO2020/123946, PCT Pub. Date Jun. 18, 2020.
Claims priority of provisional application 62/845,052, filed on May 8, 2019.
Claims priority of provisional application 62/778,901, filed on Dec. 13, 2018.
Prior Publication US 2022/0127491 A1, Apr. 28, 2022
Int. Cl. C09D 165/00 (2006.01); C08G 61/02 (2006.01); C08K 3/013 (2018.01); C09D 5/08 (2006.01)

CPC C09D 165/00 (2013.01) [C08G 61/02 (2013.01); C08K 3/013 (2018.01); C09D 5/08 (2013.01); C08G 2150/90 (2013.01); C08G 2261/3325 (2013.01); C08G 2261/418 (2013.01)]

24 Claims

1. A coating composition comprising:

5-99.999 wt. %, based on the total weight of the coating composition, of an olefinic resin composition; and

0.001 to 95 wt. %, based on the total weight of the coating composition, of an inorganic filler selected from aluminum powder or alloys thereof, aluminum flakes or alloys thereof, micaceous iron oxide, mica, glass fibers, glass flakes, wollastonite calcium carbonate, silica, talc, and mixtures thereof, wherein the olefinic resin composition comprises:

an olefinic component consisting of:

0-100 wt. %, based on the total weight of the olefinic component, of at least one cyclic olefin selected from the group consisting of Formulae (I), (II), and (III);

optionally, 0-20 wt. %, based on the total weight of the olefinic component, at least one linear olefin of Formula (IV);

wherein the wt. % of the olefins of Formulae (1), (II), (III), and optionally (IV) add to 100 wt. % of the olefinic component, and

at least one metal carbene olefin metathesis catalyst, present in an olefin to catalyst molar ratio of 10,000,000:1 to 1,000:1,

wherein the cyclic olefin of Formulae (I), (II), and (III), and the linear olefin of Formula (IV) have the following structures:

wherein:

R^ais H, optionally substituted linear or branched C_1-24alkyl, optionally substituted linear or branched C_2-24alkenyl, halogen, —C(O)R^f, —CH₂—C(O)R^f, —OR^g, —CH₂—OR^g, —CN, —NO₂, —CF₃, —P(O)(OR^h)₂, —OP(O)(OR^h)₂, —S(O)₂OR^h, —OS(O)₂R^h, optionally substituted heterocycle, —CH₂-(optionally substituted heterocycle), optionally substituted C_3-10cycloalkyl, —CH₂-(optionally substituted C_3-10cycloalkyl), optionally substituted C_5-24aryl, —CH₂-(optionally substituted C_5-24aryl), optionally substituted C_3-12cycloalkenyl, —CH₂-(optionally substituted C_3-12cycloalkenyl), C(R^h)(Rⁱ)COOR^j, —C(R^h)(Rⁱ)C(O)H, —C(R^h)(Rⁱ)C(O)R^k, —C(R^h)(Rⁱ)CR′(OR^m)(ORⁿ), —C(R^h)(Rⁱ)C(O)NR^oR^p, —C(R^h)(Rⁱ)C(O)NR^oORⁿ, or

R^bis H, optionally substituted linear or branched C_1-24alkyl, optionally substituted linear or branched C_2-24alkenyl, halogen, —C(O)R^f, —CH₂—C(O)R^f, —OR^g, —CH₂—OR^g, —CN, —NO₂, —CF₃, —P(O)(OR^h)₂, —OP(O)(OR^h)₂, —Si(OR^k)₃—S(O)₂OR^h, —OS(O)₂R^h, optionally substituted heterocycle, spiro optionally substituted heterocycle, —CH₂-(optionally substituted heterocycle), optionally substituted C_3-10cycloalkyl, —CH₂-(optionally substituted C_3-10cycloalkyl), optionally substituted C_5-24aryl, —CH₂-(optionally substituted C_5-24aryl), optionally substituted C_3-12cycloalkenyl, —CH₂-(optionally substituted C_3-12cycloalkenyl), C(R^h)(Rⁱ)COOR^j, —C(R^h)(Rⁱ)C(O)H, —C(R^h)(Rⁱ)C(O)R^k, —C(R^h)(Rⁱ)CR^l(OR^m)(ORⁿ), —C(R^h)(Rⁱ)C(O)NR^oR^p, —C(R^h)(Rⁱ)C(O)NR^oORⁿ;

R^cis H, optionally substituted linear or branched C_1-24alkyl, optionally substituted linear or branched C_2-24alkenyl, halogen, —C(O)R^f, —CH₂—C(O)R^f, —OR^g, —CH₂—OR^g, CN, NO₂, —CF₃, —P(O)(OR^h)₂, —OP(O)(OR^h)₂, —S(O)₂OR^h, —OS(O)₂R^h, optionally substituted heterocycle, —CH₂-(optionally substituted heterocycle), optionally substituted C_3-10cycloalkyl, —CH₂-(optionally substituted C_3-10cycloalkyl), optionally substituted C_5-24aryl, —CH₂-(optionally substituted C_5-24aryl), optionally substituted C_3-12cycloalkenyl, —CH₂-(optionally substituted C_3-12cycloalkenyl), C(R^h)(Rⁱ) COOR^j, —C(R^h)(Rⁱ)C(O)H, —C(R^h)(Rⁱ)C(O)R^k, —C(R^h)(Rⁱ)CR^l(OR^m)(ORⁿ), —C(R^h)(Rⁱ)C(O)NR^oR^p, —C(R^h)(Rⁱ)C(O)NR^oORⁿ;

R^dis H, optionally substituted linear or branched C_1-24alkyl, optionally substituted linear or branched C_2-24alkenyl, halogen, —C(O)R^f, —CH₂—C(O)R^f, —OR^g, —CH₂—OR^g, CN, NO₂, —CF₃, —P(O)(OR^h)₂, —OP(O)(OR^h)₂, —S(O)₂OR^h, —OS(O)₂R^h, optionally substituted heterocycle, —CH₂-(optionally substituted heterocycle), optionally substituted C_3-10cycloalkyl, —CH₂-(optionally substituted C_3-10cycloalkyl), optionally substituted C_5-24aryl, —CH₂-(optionally substituted C_5-24aryl), optionally substituted C_3-12cycloalkenyl, —CH₂-(optionally substituted C_3-12cycloalkenyl), C(R^h)(Rⁱ) COOR^j, —C(R^h)(Rⁱ)C(O)H, —C(R^h)(Rⁱ)C(O)R^k, —C(R^h)(Rⁱ)CR^l(OR^m)(ORⁿ), —C(R^h)(Rⁱ)C(O)NR^oR^p, —C(R^h)(Rⁱ)C(O)NR^oORⁿ;

each R^sis independently optionally substituted linear or branched C_1-24alkyl, optionally substituted linear or branched C_2-24alkenyl, halogen, —C(O)R^f, —CH₂—C(O)R^f,—OR^g, —CH₂—OR^g, —CN, —NO₂, —CF₃, —P(O)(OR^h)₂,—OP(O)(OR^h)₂, —S(O)₂OR^h, —OS(O)₂R^h, optionally substituted heterocycle, —CH₂-(optionally substituted heterocycle), optionally substituted C_3-10cycloalkyl, —CH₂-(optionally substituted C_3-10cycloalkyl), optionally substituted C_5-24aryl, —CH₂-(optionally substituted C_5-24aryl), optionally substituted C_3-12cycloalkenyl, —CH₂-(optionally substituted C_3-12cycloalkenyl), C(R^h)(Rⁱ)COOR^j, —C(R^h)(Rⁱ)C(O)H, —C(R^h)(Rⁱ)C(O)R^k, —C(R^h)(Rⁱ)CR^l(OR^m)(ORⁿ), —C(R^h)(Rⁱ)C(O)NR^oR^p, —C(R^h)(Rⁱ)C(O)NR^oRⁿ;

t is 0, 1, 2, 3, 4, 5, or 6;

R^fis OH, OR^k, NR^gR^h, optionally substituted linear or branched C_1-24alkyl, optionally substituted C_3-10cycloalkyl, optionally substituted heterocycle, optionally substituted C_5-24aryl, or optionally substituted C_3-12cycloalkenyl;

R^gis H, optionally substituted linear or branched C_1-24alkyl, optionally substituted C_3-10cycloalkyl, optionally substituted heterocycle, optionally substituted C_5-24aryl, optionally substituted linear or branched C_2-24alkenyl, —C(O)-(optionally substituted C_5-24aryl), —C(O)-(optionally substituted linear or branched C_2-24alkenyl), or optionally substituted C_3-12cycloalkenyl;

R^his H, optionally substituted linear or branched C_1-24alkyl, optionally substituted C_3-10cycloalkyl, optionally substituted heterocycle, optionally substituted C_5-24aryl, or optionally substituted C_3-12cycloalkenyl;

Rⁱis H, optionally substituted linear or branched C_1-24alkyl, optionally substituted C_3-10cycloalkyl, optionally substituted heterocycle, optionally substituted C_5-24aryl, or optionally substituted C_3-12cycloalkenyl;

R^jis H, optionally substituted linear or branched C_1-24alkyl, optionally substituted C_3-10cycloalkyl, optionally substituted heterocycle, optionally substituted C_5-24aryl, or optionally substituted C_3-12cycloalkenyl;

R^kis optionally substituted linear or branched C_1-24alkyl, optionally substituted C_3-10cycloalkyl, optionally substituted heterocycle, optionally substituted C_5-24aryl, or optionally substituted C_3-12cycloalkenyl;

R^lis H, optionally substituted linear or branched C_1-24alkyl, optionally substituted C_3-10cycloalkyl, optionally substituted heterocycle, optionally substituted C_5-24aryl, or optionally substituted C_3-12cycloalkenyl;

R^mis H, optionally substituted linear or branched C_1-24alkyl, optionally substituted C_3-10cycloalkyl, optionally substituted heterocycle, optionally substituted C_5-24aryl, or optionally substituted C_3-12cycloalkenyl;

Rⁿis H, optionally substituted linear or branched C_1-24alkyl, optionally substituted C_3-10cycloalkyl, optionally substituted heterocycle, optionally substituted C_5-24aryl, or optionally substituted C_3-12cycloalkenyl;

R^ois H, optionally substituted linear or branched C_1-24alkyl, optionally substituted C_3-10cycloalkyl, optionally substituted heterocycle, optionally substituted C_5-24aryl, or optionally substituted C_3-12cycloalkenyl;

R^pis H, optionally substituted linear or branched C_1-24alkyl, optionally substituted C_3-10cycloalkyl, optionally substituted heterocycle, optionally substituted C_5-24aryl, or optionally substituted C_3-12cycloalkenyl; and

z is 0, 1, 2, or 3.