Granted Patent B2

US 12,655,249 · App. 17/998,075 · Granted Jun 16, 2026

Inventors: Li-Sheng Wang (Azusa, CA); Brian Edgecombe (Anaheim, CA); Wenliang Patrick Yang (Ballston Lake, NY); Mei Chia Liao (Pomona, CA)

C08G61/08C08G61/12C08G2150/00C08G2170/00C08G2261/135C08G2261/1426C08G2261/3324C08G2261/418

Abstract

Claims (69)

1 . A composition comprising:

a) at least one norbornene ester, wherein the at least one norbornene ester is of formula (VII) and has the following structure:

b) tricyclopentadiene (TCPD);

c) optionally dicyclopentadiene (DCPD); and

d) at least one olefin metathesis catalyst.

2 . The composition of claim 1 , wherein:

the at least one norbornene ester is present in the composition in an amount of about 50 wt. % to about 60 wt. %, based on the total weight of the composition; and

the TCPD is present in the composition in an amount of about 40 wt. % to about 50 wt. %, based on the total weight of the composition.

3 . The composition of claim 1 , wherein:

the at least one norbornene ester is present in the composition in an amount ranging from about 30-50 wt. %, based on the total weight of the composition;

the TCPD is present in the composition in an amount ranging from about 50-30 wt. %, based on the total weight of the composition; and

the DCPD is present in the composition in an amount ranging from about 20-0.1 wt. %, based on the total weight of the composition.

4 . The composition of claim 1 , wherein the at least one 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, or

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.

5 . The composition of claim 1 , further comprising at least one adhesion promoter composition, at least one additive, at least one curing agent, or any combination thereof.

6 . The composition of claim 5 , where the at least one adhesion promoter composition comprises at least one compound containing at least two isocyanate groups.

7 . The composition of claim 5 , wherein the at least one adhesion promoter composition further comprises at least one compound containing at least one heteroatom-containing functional group and at least one metathesis-active olefin.

8 . The composition of claim 7 , wherein the compound containing a heteroatom-containing functional group and a metathesis-active olefin is reacted with the at least one compound containing at least two isocyanate groups.

9 . The composition of claim 5 , where the at least one adhesion promoter composition comprises at least one organofunctional silane compound.

10 . The composition of claim 5 , wherein the at least one 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, and mixtures thereof.

11 . The composition of claim 10 , wherein the at least one additive is an inorganic filler present in an amount ranging from about 0.01-95 wt. %, based on the total weight of the composition.

12 . The composition of claim 10 , wherein the at least one additive is a coupling agent.

13 . An article of manufacture, comprising the composition of claim 1 .

14 . A method of making a molded article, comprising:

forming a resin composition comprising the composition of claim 1 ,

contacting the resin composition with at least one substrate, and

subjecting the resin composition to conditions effective to promote an olefin metathesis reaction of the at least one norbornene ester, the TCPD, and, if present, the DCPD.

15 . A method for coating at least one substrate, comprising:

optionally applying an adhesion promoter onto at least a portion of a surface of the at least one substrate;

applying onto the at least portion of the surface of the at least one substrate a composition comprising the composition of claim 1 ; and

curing the coating applied to the substrate surface.

16 . An article of manufacture, comprising the at least one coated substrate of claim 15 .

Assignments (1)

Continuity (3)

References Cited (9)