IP Library › Granted Patent US 12,247,134

Granted Patent B2

US 12,247,134 · App. 17/311,495 · Granted Mar 11, 2025

Coating compositions

Inventors: Brian L. Conley (Longmont, CO); Shengxi Li (Arcadia, CA); Nathan A. Mason (Inglewood, CA); Madhura M. Pade (Pasadena, CA); Wenliang P. Yang (Ballston Lake, NY); John H. Phillips (Los Angeles, CA); Brian Edgecombe (Anaheim, CA); Kristina Goulinian (Glendale, CA); Jenny Parchen (Arcadia, CA)

Assignee: MATERIA, INC.

C09D165/00 C08G61/02 C08K3/013 C09D5/08 C08G2150/90 C08G2261/3325 C08G2261/418

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Quick Facts

Patent No.: US 12,247,134
App. No.: 17/311,495
Granted: Mar 11, 2025
Kind: B2

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Abstract

This invention relates to compositions suitable for use as coatings. More particularly, this invention relates to compositions suitable for use as industrial coatings such as anti-corrosion coatings, protective coatings and adhesive coatings. This invention relates to compositions and methods for coating substrates. More particularly, the invention relates to coating compositions and methods for coating substrates, where the coating compositions comprise polymerized olefins and cyclic olefins, via different chemical transformations. The invention also relates to methods of applying the coatings to the substrates.

Claims (213)

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 a is H, optionally substituted linear or branched C 1-24 alkyl, optionally substituted linear or branched C 2-24 alkenyl, halogen, —C(O)R f , —CH 2 —C(O)R f , —OR g , —CH 2 —OR g , —CN, —NO 2 , —CF 3 , —P(O)(OR h ) 2 , —OP(O)(OR h ) 2 , —S(O) 2 OR h , —OS(O) 2 R h , optionally substituted heterocycle, —CH 2 -(optionally substituted heterocycle), optionally substituted C 3-10 cycloalkyl, —CH 2 -(optionally substituted C 3-10 cycloalkyl), optionally substituted C 5-24 aryl, —CH 2 -(optionally substituted C 5-24 aryl), optionally substituted C 3-12 cycloalkenyl, —CH 2 -(optionally substituted C 3-12 cycloalkenyl), C(R h )(R i )COOR j , —C(R h )(R i )C(O)H, —C(R h )(R i )C(O)R k , —C(R h )(R i )CR′(OR m )(OR n ), —C(R h )(R i )C(O)NR o R p , —C(R h )(R i )C(O)NR o OR n , or

R b is H, optionally substituted linear or branched C 1-24 alkyl, optionally substituted linear or branched C 2-24 alkenyl, halogen, —C(O)R f , —CH 2 —C(O)R f , —OR g , —CH 2 —OR g , —CN, —NO 2 , —CF 3 , —P(O)(OR h ) 2 , —OP(O)(OR h ) 2 , —Si(OR k ) 3 —S(O) 2 OR h , —OS(O) 2 R h , optionally substituted heterocycle, spiro optionally substituted heterocycle, —CH 2 -(optionally substituted heterocycle), optionally substituted C 3-10 cycloalkyl, —CH 2 -(optionally substituted C 3-10 cycloalkyl), optionally substituted C 5-24 aryl, —CH 2 -(optionally substituted C 5-24 aryl), optionally substituted C 3-12 cycloalkenyl, —CH 2 -(optionally substituted C 3-12 cycloalkenyl), C(R h )(R i )COOR j , —C(R h )(R i )C(O)H, —C(R h )(R i )C(O)R k , —C(R h )(R i )CR l (OR m )(OR n ), —C(R h )(R i )C(O)NR o R p , —C(R h )(R i )C(O)NR o OR n ;

R c is H, optionally substituted linear or branched C 1-24 alkyl, optionally substituted linear or branched C 2-24 alkenyl, halogen, —C(O)R f , —CH 2 —C(O)R f , —OR g , —CH 2 —OR g , CN, NO 2 , —CF 3 , —P(O)(OR h ) 2 , —OP(O)(OR h ) 2 , —S(O) 2 OR h , —OS(O) 2 R h , optionally substituted heterocycle, —CH 2 -(optionally substituted heterocycle), optionally substituted C 3-10 cycloalkyl, —CH 2 -(optionally substituted C 3-10 cycloalkyl), optionally substituted C 5-24 aryl, —CH 2 -(optionally substituted C 5-24 aryl), optionally substituted C 3-12 cycloalkenyl, —CH 2 -(optionally substituted C 3-12 cycloalkenyl), C(R h )(R i ) COOR j , —C(R h )(R i )C(O)H, —C(R h )(R i )C(O)R k , —C(R h )(R i )CR l (OR m )(OR n ), —C(R h )(R i )C(O)NR o R p , —C(R h )(R i )C(O)NR o OR n ;

R d is H, optionally substituted linear or branched C 1-24 alkyl, optionally substituted linear or branched C 2-24 alkenyl, halogen, —C(O)R f , —CH 2 —C(O)R f , —OR g , —CH 2 —OR g , CN, NO 2 , —CF 3 , —P(O)(OR h ) 2 , —OP(O)(OR h ) 2 , —S(O) 2 OR h , —OS(O) 2 R h , optionally substituted heterocycle, —CH 2 -(optionally substituted heterocycle), optionally substituted C 3-10 cycloalkyl, —CH 2 -(optionally substituted C 3-10 cycloalkyl), optionally substituted C 5-24 aryl, —CH 2 -(optionally substituted C 5-24 aryl), optionally substituted C 3-12 cycloalkenyl, —CH 2 -(optionally substituted C 3-12 cycloalkenyl), C(R h )(R i ) COOR j , —C(R h )(R i )C(O)H, —C(R h )(R i )C(O)R k , —C(R h )(R i )CR l (OR m )(OR n ), —C(R h )(R i )C(O)NR o R p , —C(R h )(R i )C(O)NR o OR n ;

each R s is independently optionally substituted linear or branched C 1-24 alkyl, optionally substituted linear or branched C 2-24 alkenyl, halogen, —C(O)R f , —CH 2 —C(O)R f ,—OR g , —CH 2 —OR g , —CN, —NO 2 , —CF 3 , —P(O)(OR h ) 2 ,—OP(O)(OR h ) 2 , —S(O) 2 OR h , —OS(O) 2 R h , optionally substituted heterocycle, —CH 2 -(optionally substituted heterocycle), optionally substituted C 3-10 cycloalkyl, —CH 2 -(optionally substituted C 3-10 cycloalkyl), optionally substituted C 5-24 aryl, —CH 2 -(optionally substituted C 5-24 aryl), optionally substituted C 3-12 cycloalkenyl, —CH 2 -(optionally substituted C 3-12 cycloalkenyl), C(R h )(R i )COOR j , —C(R h )(R i )C(O)H, —C(R h )(R i )C(O)R k , —C(R h )(R i )CR l (OR m )(OR n ), —C(R h )(R i )C(O)NR o R p , —C(R h )(R i )C(O)NR o R n ;

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

R f is OH, OR k , NR g R h , optionally substituted linear or branched C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 cycloalkenyl;

R g is H, optionally substituted linear or branched C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, optionally substituted linear or branched C 2-24 alkenyl, —C(O)-(optionally substituted C 5-24 aryl), —C(O)-(optionally substituted linear or branched C 2-24 alkenyl), or optionally substituted C 3-12 cycloalkenyl;

R h is H, optionally substituted linear or branched C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 cycloalkenyl;

R i is H, optionally substituted linear or branched C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 cycloalkenyl;

R j is H, optionally substituted linear or branched C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 cycloalkenyl;

R k is optionally substituted linear or branched C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 cycloalkenyl;

R l is H, optionally substituted linear or branched C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 cycloalkenyl;

R m is H, optionally substituted linear or branched C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 cycloalkenyl;

R n is H, optionally substituted linear or branched C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 cycloalkenyl;

R o is H, optionally substituted linear or branched C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 cycloalkenyl;

R p is H, optionally substituted linear or branched C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-12 cycloalkenyl; and

z is 0, 1, 2, or 3.

2. The coating composition of claim 1 , wherein:

R a is H, optionally substituted linear or branched C 1-12 alkyl, optionally substituted linear or branched C 2-6 alkenyl, halogen, —C(O)R f , —OR g , —CN, —NO 2 , —CF 3 , —P(O)(OR h ) 2 , —OP(O)(OR h ) 2 , —S(O) 2 OR h , —OS(O) 2 R h , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 6-10 aryl, optionally substituted C 3-12 cycloalkenyl, or

R b is H, optionally substituted linear or branched C 1-12 alkyl, optionally substituted linear or branched C 2-6 alkenyl, halogen, —C(O)R f , —OR g , —CN, —NO 2 , —CF 3 , —P(O)(OR h ) 2 , —OP(O)(OR h ) 2 , —S(O) 2 OR h , —OS(O) 2 R h , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 6-10 aryl, optionally substituted C 3-12 cycloalkenyl;

R c is H, optionally substituted linear or branched C 1-12 alkyl, optionally substituted linear or branched C 2-6 alkenyl, halogen, —C(O)R f , —OR g , —CN, —NO 2 , —CF 3 , —P(O)(OR h ) 2 , —OP(O)(OR h ) 2 , —S(O) 2 OR h , —OS(O) 2 R h , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 6-10 aryl, optionally substituted C 3-12 cycloalkenyl;

R d is H, optionally substituted linear or branched C 1-12 alkyl, optionally substituted linear or branched C 2-6 alkenyl, halogen, —C(O)R f , —OR g , —CN, —NO 2 , —CF 3 , —P(O)(OR h ) 2 , —OP(O)(OR h ) 2 , —S(O) 2 OR h , —OS(O) 2 R h , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 6-10 aryl, optionally substituted C 3-12 cycloalkenyl;

t is 0;

R f is OH, OR k , NR g R h , optionally substituted C 1-12 alkyl, optionally substituted C 3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 cycloalkenyl;

R g is H, optionally substituted C 1-12 alkyl, optionally substituted C 3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 cycloalkenyl;

R h is H, optionally substituted C 1-12 alkyl, optionally substituted C 3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 cycloalkenyl;

z is 2;

R i is H, optionally substituted C 1-12 alkyl, optionally substituted C 3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 cycloalkenyl;

R j is H, optionally substituted C 1-12 alkyl, optionally substituted C 3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 cycloalkenyl;

R k is optionally substituted C 1-12 alkyl, optionally substituted C 3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 cycloalkenyl;

R l is H, optionally substituted C 1-12 alkyl, optionally substituted C 3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 cycloalkenyl;

R m is H, optionally substituted C 1-12 alkyl, optionally substituted C 3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 cycloalkenyl;

R n is H, optionally substituted C 1-12 alkyl, optionally substituted C 3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 cycloalkenyl;

R o is H, optionally substituted C 1-12 alkyl, optionally substituted C 3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 cycloalkenyl; and

R p is H, optionally substituted C 1-12 alkyl, optionally substituted C 3-8 cycloalkyl, optionally substituted heterocycle, optionally substituted C 6-10 aryl, or optionally substituted C 3-12 cycloalkenyl.

3. The coating composition of claim 1 , wherein

the cyclic olefin of formula (I) is ENB-DDA, HNB-DDA, or a mixture thereof;

the cyclic olefin of formula (II) is HENB, NBCbSi, ONB, NB-methanol, NB-dimethanol, NB-epoxide, NB-triethoxysilane, NB-Fluorocarbon (1), NB-fluorocarbon (2), NB-fluorocarbon (3), or a mixture thereof

and

the cyclic olefin of formula (III) is tricyclopentadiene (TCPD), dicyclopentadiene (DCPD), or a mixture thereof.

4. The coating composition of claim 1 , wherein the at least one metal carbene olefin metathesis catalyst has the structure of Formula (1):

wherein:

M is ruthenium;

L 1 , L 2 , and L 3 are independently neutral electron donor ligands;

n is 0 or 1;

m is 0, 1, or 2;

k is 0 or 1;

X 1 and X 2 are independently anionic ligands; and

R 1 and R 2 are independently hydrogen, optionally substituted hydrocarbyl, optionally substituted heteroatom-containing hydrocarbyl; or R 1 and R 2 are linked together to form one or more cyclic groups.

5. The coating composition of claim 1 , wherein the at least one metal carbene olefin metathesis catalyst has the structure of Formula (2):

wherein:

M is ruthenium;

L 1 is a neutral electron donor ligand;

X 1 and X 2 are independently anionic ligands;

W is O, halogen, NR 33 or S;

R 19 is H, optionally substituted C 1-24 alkyl, —C(R 34 )(R 35 ) COOR 36 , —C(R 34 )(R 35 )C(O)H, —C(R 34 )(R 35 )C(O)R 37 , —C(R 34 )(R 35 )CR 38 (OR 39 )(OR 40 ), —C(R 34 )(R 35 )C(O)NR 41 R 42 , —C(R 34 )(R 35 )C(O)NR 41 OR 40 , —C(O)R 25 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl, optionally substituted C 3-8 cycloalkenyl, or when W is NR 33 , then R 19 together with R 33 can form an optionally substituted heterocyclic ring or when W is halogen then R 19 is nil;

R 20 is H, optionally substituted C 1-24 alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) x R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl, optionally substituted C 3-8 cycloalkenyl or together with R 21 can form a polycyclic ring;

R 21 is H, optionally substituted C 1-24 alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) x R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl, optionally substituted C 3-8 cycloalkenyl or together with R 20 or together with R 22 can form a polycyclic ring;

R 22 is H, optionally substituted C 1-24 alkyl, halogen, —C(O)R 25 ,—OR 26 , CN, —NR 27 R 28 , NO 2 ,—CF 3 ,—S(O) x R 29 ,—P(O)(OH) 2 ,—OP(O)(OH) 2 ,—SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl, optionally substituted C 3-8 cycloalkenyl or together with R 21 or together with R 23 can form a polycyclic ring;

R 23 is H, optionally substituted C 1-24 alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) x R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl, optionally substituted C 3-8 cycloalkenyl or together with R 22 can form a polycyclic ring;

R 24 is H, optionally substituted C 1-24 alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) x R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl or optionally substituted C 3-8 cycloalkenyl;

R 25 is OH, OR 30 , NR 27 R 28 , optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl or optionally substituted C 3-8 cycloalkenyl;

R 26 is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl or optionally substituted C 3-8 cycloalkenyl;

R 27 is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl or optionally substituted C 3-8 cycloalkenyl;

R 28 is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl or optionally substituted C 3-8 cycloalkenyl;

R 29 is H, optionally substituted C 1-24 alkyl, OR 26 , —NR 27 R 28 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl or optionally substituted C 3-8 cycloalkenyl;

R 30 is optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl or optionally substituted C 3-8 cycloalkenyl;

R 31 is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl or optionally substituted C 3-8 cycloalkenyl;

R 33 is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl or optionally substituted C 3-8 cycloalkenyl;

R 34 is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl or optionally substituted C 3-8 cycloalkenyl;

R 35 is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl or optionally substituted C 3-8 cycloalkenyl;

R 36 is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl or optionally substituted C 3-8 cycloalkenyl;

R 37 is optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl or optionally substituted C 3-8 cycloalkenyl;

R 38 is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl or optionally substituted C 3-8 cycloalkenyl;

R 39 is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl or optionally substituted C 3-8 cycloalkenyl;

R 40 is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl or optionally substituted C 3-8 cycloalkenyl;

R 41 is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl or optionally substituted C 3-8 cycloalkenyl;

R 42 is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl or optionally substituted C 3-8 cycloalkenyl; and

x is 1 or 2.

6. The coating composition of claim 1 , wherein the coating composition comprises at least one cyclic olefin represented selected from the group consisting of both Formulae (I) and (II), both Formulae (I) and (III), and both Formulae (II) and (III).

7. The coating composition of claim 1 , wherein the coating composition further comprises a coating additive is selected from the group consisting of a gel modifier, a hardness modulator, an impact modifier, an antioxidant, an antiozonant, a filler, a binder, a thixotrope, a rheology modifier, a dispersant, a wetting agent, a plasticizer, a pigment, a flame retardant, a dye, fibers, a reinforcement material, a coupling agent, a UV absorber, a UV light stabilizer, a film former, a lubricant, an adhesion promoter and mixtures thereof.

8. The coating composition of claim 1 , wherein the inorganic filler is selected from aluminum powder or alloys thereof, aluminum flakes or alloys thereof, micaceous iron oxide, mica, and mixtures thereof.

9. The coating composition of claim 4 , wherein:

L 1 is

R 1 is H, optionally substituted C 1-24 alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) x R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl, optionally substituted C 3-8 cycloalkenyl, or together with R 2 can form a spiro compound, or together with R 3 or together with R 4 can form a polycyclic ring;

R 2 is H, optionally substituted C 1-24 alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , —NO 2 , —CF 3 , —S(O) x R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl, optionally substituted C 3-8 cycloalkenyl or together with R 1 can form a spiro compound, or together with R 3 or together with R 4 can form a polycyclic ring;

R 3 is H, optionally substituted C 1-24 alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) x R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl, optionally substituted C 3-8 cycloalkenyl, or together with R 2 or together with R 1 can form a polycyclic ring, or together with R 4 can form a spiro compound;

R 4 is H, optionally substituted C 1-24 alkyl, halogen, —C(O)R 25 , —OR 26 , —CN, —NR 27 R 28 , —NO 2 , —CF 3 , —S(O) x R 29 ,—P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl, optionally substituted C 3-8 cycloalkenyl, or together with R 3 can form a spiro compound, or together with R 2 or together with R 1 can form a polycyclic ring;

R 5 is H, optionally substituted C 1-24 alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , —NO 2 , —CF 3 , —S(O) x R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl, optionally substituted C 3-8 cycloalkenyl, or together with R 6 can form an optionally substituted polycyclic ring;

R 6 is H, optionally substituted C 1-24 alkyl, halogen, —C(O)R 25 , —OR 26 , —CN, —NR 27 R 28 , —NO 2 , —CF 3 , —S(O) x R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl, optionally substituted C 3-8 cycloalkenyl, or together with R 5 or together with R 7 can form an optionally substituted polycyclic ring;

R 7 is H, optionally substituted C 1-24 alkyl, halogen, —C(O)R 25 , —OR 26 , —CN, —NR 27 R 28 , —NO 2 , —CF 3 , —S(O) x R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl optionally substituted C 3-8 cycloalkenyl, or together with R 6 or together with R 8 can form an optionally substituted polycyclic ring;

R 8 is H, optionally substituted C 1-24 alkyl, halogen, —C(O)R 25 , —OR 26 , —CN, —NR 27 R 28 , —NO 2 , —CF 3 , —S(O) x R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl, optionally substituted C 3-8 cycloalkenyl, or together with R 7 or together with R 9 can form an optionally substituted polycyclic ring;

R 9 is H, optionally substituted C 1-24 alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 ,—CF 3 , —S(O) x R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl, optionally substituted C 3-8 cycloalkenyl, or together with R 8 can form an optionally substituted polycyclic ring;

R 10 is H, optionally substituted C 1-24 alkyl, halogen, —C(O)R 25 , —OR 26 , —CN, —NR 27 R 28 , —NO 2 , —CF 3 , —S(O) x R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl, optionally substituted C 3-8 cycloalkenyl, or together with R 11 can form an optionally substituted polycyclic ring;

R 11 is H, optionally substituted C 1-24 alkyl, halogen, —C(O)R 25 , —OR 26 , —CN, —NR 27 R 28 , —NO 2 , —CF 3 , —S(O) x R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl, optionally substituted C 3-8 cycloalkenyl, or together with R 10 or together with R 12 can form an optionally substituted polycyclic ring;

R 12 is H, optionally substituted C 1-24 alkyl, halogen, —C(O)R 25 , —OR 26 , —CN, —NR 27 R 28 , —NO 2 , —CF 3 , —S(O) x R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl, optionally substituted C 3-8 cycloalkenyl, or together with R 11 or together with R 13 can form an optionally substituted polycyclic ring;

R 13 is H, optionally substituted C 1-24 alkyl, halogen, —C(O)R 25 , —OR 26 , —CN, —NR 27 R 28 , —NO 2 , —CF 3 , —S(O) x R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl, optionally substituted C 3-8 cycloalkenyl, or together with R 14 or together with R 12 can form an optionally substituted polycyclic ring;

R 14 is H, optionally substituted C 1-24 alkyl, halogen, —C(O)R 25 , —OR 26 , —CN, —NR 27 R 28 , —NO 2 , —CF 3 , —S(O) x R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl, optionally substituted C 3-8 cycloalkenyl, or together with R 13 can form a polycyclic ring;

R 25 is —OH, —OR 30 , —NR 27 R 28 , optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 cycloalkenyl;

R 26 is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 cycloalkenyl;

R 27 is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 cycloalkenyl;

R 28 is H, optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 cycloalkenyl;

R 29 is H, optionally substituted C 1-24 alkyl, —OR 26 , —NR 27 R 28 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 cycloalkenyl;

R 30 is optionally substituted C 1-24 alkyl, optionally substituted C 3-10 cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24 aryl, or optionally substituted C 3-8 cycloalkenyl;

x is 1 or 2.

10. The coating composition of claim 1 , wherein the inorganic filler is selected from aluminum powder or alloys thereof, aluminum flakes or alloys thereof, micaceous iron oxide, and mixtures thereof.

11. An article of manufacture comprising a substrate coated with a cured coating composition wherein the coating composition is a coating composition of claim 1 .

12. A method for coating a substrate material, comprising: optionally applying an adhesion promoter onto the substrate surface; applying onto the substrate surface a coating composition comprising the coating composition of claim 1 ; and curing the coating applied on the substrate surface.

13. The method of claim 12 , wherein:

t is 0;

z is 2;

14. The method of claim 12 wherein

the cyclic olefin of formula (I) is ENB-DDA, HNB-DDA, or a mixture thereof

the cyclic olefin of formula (II) is HENB, NBCbSi, ONB, NB-methanol, NB-dimethanol, NB-epoxide, NB-triethoxysilane, NB-Fluorocarbon (1), NB-fluorocarbon (2), NB-fluorocarbon (3), or a mixture thereof

and

the cyclic olefin of formula (III) is tricyclopentadiene (TCPD), dicyclopentadiene (DCPD), or a mixture thereof.

15. The method of claim 12 , wherein the at least one metal carbene olefin metathesis catalyst has the structure of Formula (1):

wherein:

M is ruthenium;

L 1 , L 2 , and L 3 are independently neutral electron donor ligands;

n is 0 or 1;

m is 0, 1, or 2;

k is 0 or 1;

X 1 and X 2 are independently anionic ligands; and

R 1 and R 2 are independently hydrogen, unsubstituted hydrocarbyl, substituted hydrocarbyl, unsubstituted heteroatom-containing hydrocarbyl, or substituted heteroatom-containing hydrocarbyl; or R 1 and R 2 are linked together to form one or more cyclic groups.

16. The method of claim 15 , wherein:

L 1 is

R 4 is H, optionally substituted C 1-24 alkyl, halogen, —C(O)R 25 , —OR 26 , —CN, —NR 27 R 28 , —NO 2 , —CF 3 , —S(O) x R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl, optionally substituted C 3-8 cycloalkenyl, or together with R 3 can form a spiro compound, or together with R 2 or together with R 1 can form a polycyclic ring;

R 9 is H, optionally substituted C 1-24 alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) x R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl, optionally substituted C 3-8 cycloalkenyl, or together with R 8 can form an optionally substituted polycyclic ring;

R 12 is H, optionally substituted C 1-24 alkyl, halogen, —C(O)R 25 , —OR 26 , —CN, —NR 27 R 28 , —NO 2 , —CF 3 , —S(O) x R 29 , —P(O)(OH) 2 , —OP (O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl, optionally substituted C 3-8 cycloalkenyl, or together with R 11 or together with R 13 can form an optionally substituted polycyclic ring;

x is 1 or 2.

17. The method of claim 15 , wherein: L 2 is PR H1 R H2 R H3 wherein: R H1 , R H2 , and R H3 are each independently optionally substituted C 6 -C 10 aryl, optionally substituted C 1 -C 10 alkyl, or optionally substituted C 3 -C 10 cycloalkyl.

18. The method of claim 15 , wherein: R 1 is hydrogen and R 2 is phenyl; or R 1 is hydrogen and R 2 is 3-methyl-1-propenyl; or R 1 and R 2 are linked together to form 3-phenylindenylid-1-ene.

19. The method of claim 12 , wherein the at least one metal carbene olefin metathesis catalyst has the structure of Formula (2):

wherein:

M is ruthenium;

L 1 is a neutral electron donor ligand;

X 1 and X 2 are independently anionic ligands;

W is O, halogen, NR 33 or S;

R 19 is H, optionally substituted C 1-24 alkyl, —C(R 34 )(R 35 ) COOR 36 , —C(R 34 )(R 35 )C(O)H, —C(R 34 )(R 35 )C(O)R 37 , —C(R 34 )(R 35 )CR 38 (OR 39 )(OR 40 ), —C(R 34 ) (R 35 )C(O)NR 41 R 42 , —C(R 34 )(R 35 )C(O)NR 41 OR 40 , —C(O)R 25 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl, optionally substituted C 3-8 cycloalkenyl, or when W is NR 33 , then R 19 together with R 33 can form an optionally substituted heterocyclic ring or when W is halogen then R 19 is nil;

R 22 is H, optionally substituted C 1-24 alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) x R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-10 cycloalkyl, optionally substituted C 5-24 aryl, optionally substituted C 3-8 cycloalkenyl or together with R 21 or together with R 23 can form a polycyclic ring;

x is 1 or 2.

20. The method of claim 12 , wherein the coating composition comprises at least one cyclic olefin represented selected from the group consisting of both Formulae (I) and (II), both Formulae (I) and (III), and both Formulae (II) and (III).

21. The method of claim 12 , wherein the coating composition further comprises a coating additive selected from the group consisting of a gel modifier, a hardness modulator, an impact modifier, an antioxidant, an antiozonant, a filler, a binder, a thixotrope, a rheology modifier, a dispersant, a wetting agent, a plasticizer, a pigment, a flame retardant, a dye, fibers, a reinforcement material, a coupling agent, a UV absorber, a UV light stabilizer, a film former, a lubricant, an adhesion promoter and mixtures thereof.

22. The method of claim 12 , wherein the inorganic filler is selected from aluminum powder or alloys thereof, aluminum flakes or alloys thereof, micaceous iron oxide, mica, and mixtures thereof.

23. An article of manufacture produced by the method of claim 12 .

24. The method of claim 12 , wherein the coating applied on the substrate surface is cured at room temperature.

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 15, 2025

From: MATERIA, INC.

To: EXXONMOBIL PRODUCT SOLUTIONS COMPANY

Reel/Frame 073085/0216 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 8, 2023

From: CONLEY, BRIAN L.; LI, SHENGXI; PADE, MADHURA M.; MASON, NATHAN A.; YANG, WENLIANG P.; PHILLIPS, JOHN H.; EDGECOMBE, BRIAN; GOULINIAN, KRISTINA; PARCHEN, JENNY

To: MATERIA, INC.

Reel/Frame 064521/0044 →

Continuity (3)

Provisional Application 62845052 · May 8, 2019

Provisional Application 62778901 · Dec 13, 2018

Related Publication 20220127491A1 · Apr 28, 2022

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