Production of novel resins and their uses in printing ink compositions

Claim 2

A composition comprising: (a) a predominant amount of dicyclopentadiene; and lesser amounts of (b) at least one hydrocarbon selected from the group consisting of mono-olefins, diolefins, and polyenes each having more than five carbon atoms, and having no aromatic rings; and (c) at least one member selected from the group consisting of fatty acid-containing materials and rosin acid-containing materials.

Claim 3

The composition of claim 1 comprising: (a) from about forty to about eighty-five percent, by weight, of dicyclopentadiene or a dicyclopentadiene-rich hydrocarbon fraction containing at least about seventy percent, by weight, of dicyclopentadiene or a dicyclopentadiene-rich hydrocarbon fraction containing at least about seventy percent, by weight, dicyclopentadiene and minor amounts of dimethyldicyclopentadiene and codimers of cyclopentadiene and methylcyclopentadiene; (b) from about five to about forty percent, by weight, of at least one hydrocarbon selected from the group consisting of mono-olefins, diolefins, and polyenes each having more than five carbon atoms, and having no aromatic rings; and (c) from about five to about thirty percent, by weight, of at least one member selected from the group consisting of fatty acid-containing materials and rosin acid-containing materials.

Claim 4

The composition of claim 1, wherein said composition is reacted and has a Ring and Ball softening point of from about 100° C. to about 170° C.; Gardner-Holdt solution viscosities at 25° C. (bubble seconds) of from about 0.90 to about 15.0 (60%/Wt. resin in 42 Kauri butanol gravure ink solvent) and from about 8.00 to about 100 (50%/Wt. resin in Magie 470 oil); a definite Stoddard solubility from less than about -60° C. to about 40° C.; and an Acid Number of from about 1.5 to about 10.0.

Claim 5

The composition of claim 1, wherein said composition is reacted and has a Ring and Ball softening point of from about 125° C. to about 150° C.; Gardner-Holdt solution viscosities at 25° C. (bubble seconds) of from about 1.15 to about 8.00 (60%/Wt. resin in 42 Kauri butanol gravure ink solvent) and of from about 10 to about 50 (50%/Wt. resin in Magie 470 oil); a definite Stoddard solubility from about -50° C. to about +20° C.; and an Acid Number of from about 3.0 to about 7.0.

Claim 6

A process for producing the composition of claim 1, in a reacted form comprising reacting: (a) a predominant amount of dicyclopentadiene; and lesser amounts of (b) at least one hydrocarbon selected from the group consisting of mono-olefins, diolefins, and polyenes each having more than 5 carbon atoms, and having no aromatic rings; and (c) at least one member selected from the group consisting of fatty acid-containing materials and rosin acid-containing materials.

Claim 7

A composition comprising: (a) a predominant amount of dicyclopentadiene; and lesser amounts of (b) at least one hydrocarbon selected from the group consisting of mono-olefins, diolefins, and polyenes each having more than 5 carbon atoms, and having no aromatic rings; (c) at least one member selected from the group consisting of fatty acid-containing materials and rosin acid-containing materials; and (d) at least one ethylenically unsaturated lower aliphatic dicarboxylic acid or anhydride.

Claim 8

A composition comprising: (a) a predominant amount of dicyclopentadiene; and lesser amounts of (b) at least one hydrocarbon selected from the group consisting of mono-olefins, diolefins, and polyenes each having more than 5 carbon atoms, and having no aromatic rings; (c) at least one member selected from the group consisting of fatty acid-containing materials and rosin acid-containing materials; and (d) at least one ethylenically unsaturated lower aliphatic dicarboxylic acid or anhydride.

Claim 9

The composition of claim 6 comprising: (a) from about forty to about eighty-five percent, by weight, of dicyclopentadiene or a dicyclopentadiene-rich hydrocarbon fraction containing at least about seventy percent, by weight, dicyclopentadiene and minor amounts of dimethyldicyclopentadiene and codimers of cyclopentadiene and methylcyclopentadiene; (b) from about five to about forty percent, by weight, of at least one hydrocarbon selected from the group consisting of mono-olefins, diolefins, and polyenes each having more than five carbon atoms, and having no aromatic rings; (c) from about five to about thirty percent, by weight, of at least one member selected from the group consisting of fatty acid-containing materials and rosin acid-containing materials; and (d) from about one to about ten percent, by weight, maleic anhydride.

Claim 10

The composition of claim 6, wherein said composition is reacted and has a Ring and Ball softening point of from about 110° C. to 180° C.; Gardner-Holdt solution viscosities at 25° C. (bubble seconds) of from about 10 to about 10,000 (60%/Wt. resin in 33-34 Kauri butanol reference oil-H.D.T.); a Hydrocarbon Dilution Tolerance test value (solubility-Wt %) of from about 25 to about 1000 (60%/Wt. resin in 33-34 Kauri butanol reference oil-H.D.T.); and an Acid Number of from about 10 to about 40.

Claim 11

The composition of claim 6, wherein said composition is reacted and has a Ring and Ball softening point from about 130° C. to about 175° C.; a Gardner-Holdt solution viscosity at 25° C. (bubble seconds) of from about 100 to about 2,000 (60%/Wt. resin in 33-34 Kauri butanol reference oil-H.D.T.); a Hydrocarbon Dilution Tolerance test value (solubility-Wt. %) of from about 50 to about 600 (60%/Wt. resin in 33-34 Kauri butanol reference oil-H.D.T.); and an Acid Number of from about 10 to about 30.

Claim 12

The composition of claim 6, wherein said composition is reacted and has a Ring and Ball softening point of from about 140° C. to about 160° C.; a Gardner-Holdt solution viscosity at 25° C. (bubble seconds) of from about 200 to about 1,200 (60%/Wt. resin in 33-34 Kauri butanol reference oil-H.D.T.); a Hydrocarbon Dilution Tolerance test value (solubility-Wt. %) of from about 125 to about 250 (60%/Wt. resin in 33-34 Kauri butanol reference oil-H.D.T.); and an Acid Number of from about 15 to about 25.

Claim 13

The composition of claims 1 or 6 wherein component (b) is a mono-olefin selected from the group consisting of acyclic mono-olefins (alpha olefins); acyclic mono-olefins (non alpha olefins); simple cyclic mono-olefins; bicyclic mono-olefins; bicyclic mono-olefins (Spiro type); and polycyclic mono-olefins: four types.

Claim 14

The composition of claim 11 wherein component (b) is at least one member selected from the group consisting of 1-tetradecene; 1-hexadecene; 1-octadecene; and 1-eicosene.

Claim 15

The composition of claim 11 wherein component (b) is an acyclic mono-olefin (non-alpha olefin) selected from the group consisting of 2,2,4-trimethyl-2-pentene; 2,3,4-trimethyl 3-hexene; 7-tetradecene; and 5-eicosene.

Claim 16

The composition of claim 11 wherein component (b) is a simple cyclic mono-olefin selected from the group consisting of cyclotetradecene; cyclohexadecene; and cyclooctadecene.

Claim 17

The composition of claims 1 or 6 wherein component (b) is a diolefin selected from the group consisting of acyclic conjugated dienes; acyclic non-conjugated dienes; simple cyclic conjugated diolefins; bicyclic conjugated diolefins; polycyclic conjugated diolefins; simple cyclic non-conjugated diolefins; bicyclic non-conjugated diolefins; and polycyclic non-conjugated diolefins.

Claim 18

The composition of claim 15 wherein component (b) is an acyclic conjugated diene or acyclic non-conjugated diene selected from the group consisting of 1,3-hexadecadiene; 7,11,15-trimethyl-3-methylene-1-hexadecadiene; 4,4,7,7-tetramethyl-1-9 decadiene, and 1,19-eicosadiene.

Claim 19

The composition of claim 15 wherein component (b) is a simple cyclic conjugated or simple cyclic non-conjugated diolefin selected from the group consisting of 1,9-cyclohexadecadiene, and 1,10-cyclooctadecadiene.

Claim 20

The composition of claims 1 or 6 wherein component (b) is a polyene selected from the group consisting of acyclic conjugated polyenes; acyclic non-conjugated polyenes; simple cyclic conjugated polyenes; bicyclic conjugated polyenes, polycyclic conjugated polyenes; simple cyclic non-conjugated polyenes; bicyclic non-conjugated polyenes; and polycyclic non-conjugated polyenes.

Claim 21

The composition of claim 18 wherein component (b) is an acyclic conjugated or acyclic non-conjugated polyene selected from the group consisting of 1,6,10,14-hexadecatetraene and 1,8,11-octadecatriene.

Claim 22

The composition of claim 18 wherein component (b) is a simple cyclic conjugated or simple cyclic non-conjugated polyene selected from the group consisting of 3-methyl-1-(2,5,6 trimethyl-1-cyclohexen-1-yl)-1,3,5-hexatriene; 1,3,10,12-cyclooctadecatetraene; 1,5,9-cyclododecatriene; and 1,5,9,13 cyclohexadecatetraene.

Claim 23

A process for producing the composition of claim 6, in a reacted form, comprising reacting: (a) a predominant amount of dicyclopentadiene; and lesser amounts of (b) at least one hydrocarbon selected from the group consisting of mono-olefins, diolefins and polyenes each having more than five carbon atoms, and having no aromatic rings; (c) at least one member selected from the group consisting of fatty acid-containing materials and rosin acid-containing materials; and (d) at least one ethylenically unsaturated lower aliphatic dicarboxylic acid or anhydride.

Claim 24

A composition comprising a polymerized mixture of: (a) a predominant amount of dicyclopentadiene; and lesser amounts of (b) at least one hydrocarbon selected from the group consisting of mono-olefins, diolefins, and polyenes each having more than five carbon atoms, and having no aromatic rings; and (c) at least one member selected from the group consisting of fatty acid-containing materials and rosin acid-containing materials; wherein said composition has a Ring and Ball softening point of from about 100° C. to about 170° C.; Gardner-Holdt solution viscosities at 25° C. (bubble seconds) of from about 0.50 to about 15.0 (60%/Wt. resin in 42 Kauri butanol gravure ink solvent) and of from about 8.00 to about 100 (50%/Wt. resin in Magie 470 oil); a definite Stoddard solubility from less than about -60° C. to about 40° C.; and an Acid Number of from about 1.5 to about 10.0.

Claim 25

A composition comprising a polymerized mixture of: (a) a predominant amount of dicyclopentadiene; and lesser amounts of (b) at least one hydrocarbon selected from the group consisting of mono-olefins, diolefins, and polyenes each having more than five carbon atoms, and having no aromatic rings; and (c) at least one member selected from the group consisting of fatty acid-containing materials and rosin acid-containing materials; wherein said composition has a Ring and Ball softening point of from about 100° C. to about 170° C.; Gardner-Holdt solution viscosities at 25° C. (bubble seconds) of from about 0.50 to about 15.0 (60%/Wt. resin in 42 Kauri butanol gravure ink solvent) and of from about 8.00 to about 100 (50%/Wt. resin in Magie 470 oil); a definite Stoddard solubility from less than about -60° C. to about 40° C.; and an Acid Number of from about 1.5 to about 10.0.

Claim 26

A process for producing the composition of claim 22 comprising co-polymerizing a reaction mixture comprising: components (a), (b) and (c).

Claim 27

A composition comprising the reaction product of: (a) a predominant amount of dicyclopentadiene and lesser amounts of (b) at least one hydrocarbon selected from the group consisting of mono-olefins, diolefins, and polyenes each having more than five carbon atoms, and having no aromatic rings; (c) at least one member selected from the group consisting of fatty acid-containing materials and rosin acid-containing materials; and (d) at least one ethylenically unsaturated lower aliphatic dicarboxylic acid or anhydride, wherein said composition has a Ring and Ball softening point of from about 110° C. to about 180° C.; a Gardner-Holdt solution viscosity at 25° C. (bubble seconds) of from about 10 to about 10,000 (60%/Wt. resin in 33-34 Kauri butanol reference oil-H.D.T.); a Hydrocarbon Dilution Tolerance test value (Solubility-Wt. %) of from about 25 to about 1000 (60%/Wt. resin in 33-34 Kauri butanol reference oil H.D.T.); and an Acid Number of from about 10 to about 40.

Claim 28

A composition comprising the reaction product of: (a) a predominant amount of dicyclopentadiene and lesser amounts of (b) at least one hydrocarbon selected from the group consisting of mono-olefins, diolefins, and polyenes each having more than five carbon atoms, and having no aromatic rings; (c) at least one member selected from the group consisting of fatty acid-containing materials and rosin acid-containing materials; and (d) at least one ethylenically unsaturated lower aliphatic dicarboxylic acid or anhydride, wherein said composition has a Ring and Ball softening point of from about 110° C. to about 180° C.; a Gardner-Holdt solution viscosity at 25° C. (bubble seconds) of from about 10 to about 10,000 (60%/Wt. resin in 33-34 Kauri butanol reference oil-H.D.T.); a Hydrocarbon Dilution Tolerance test value (Solubility-Wt. %) of from about 25 to about 1000 (60%/Wt. resin in 33-34 Kauri butanol reference oil H.D.T.); and an Acid Number of from about 10 to about 40.

Claim 29

A process for producing the composition of claim 24 comprising reacting components (a), (b), (c) and (d).

Claim 30

The process of claim 25 wherein components (a), (b), (c) and (d) are reacted simultaneously in a one-step reaction process.

Claim 31

The process of claim 25, which process comprises: (1) co-polymerizing a reaction mixture comprising components (a), (b) and (c) to form a base resin, and (2) reacting the base resin with component (d).

Claim 32

The process of claims 23 or 25 wherein the reaction includes one or more aromatic olefinic monomers selected from the group consisting of vinyltoluenes, styrene, alpha-methylstyrene, indene, coumarone, methyl coumarones, dimethylstyrenes and methylindenes.

Claim 33

The composition of claim 2 comprising: (a) from about forty to about eighty-five percent, by weight, of dicyclopentadiene or a dicyclopentadiene-rich hydrocarbon fraction containing at least about forty percent, by weight, dicyclopentadiene and minor amounts of dimethyldicyclopentadiene and codimers of cyclopentadiene and methylcyclopentadiene; (b) from about five to about forty percent, by weight, of at least one hydrocarbon selected from the group consisting of mono-olefins, diolefins, and polyenes each having more than five carbon atoms, and having no aromatic rings; and (c) from about five to about thirty percent, by weight, of at least one member selected from the group consisting of fatty acid-containing materials and rosin acid-containing materials.

Claim 34

The composition of claim 7 comprising: (a) from about forty to about eighty-five percent, by weight, of dicyclopentadiene or a dicyclopentadiene-rich hydrocarbon fraction containing at least about forty percent, by weight, dicyclopentadiene and minor amounts of dimethyldicyclopentadiene and codimers of cyclopentadiene and methylcyclopentadiene; (b) from about five to about forty percent, by weight, of at least one hydrocarbon selected from the group consisting of mono-olefins, diolefins, and polyenes each having more than five carbon atoms, and having no aromatic rings; (c) from about five to about thirty percent, by weight, of at least one member selected from the group consisting of fatty acid-containing materials and rosin acid-containing materials; and (d) from about one to about ten percent, by weight, maleic anhydride.

Claim 35

A process for producing the composition of claim 29, in a reacted form comprising reacting: (a) from about forty to about eighty-five percent, by weight, of dicyclopentadiene or a dicyclopentadiene-rich hydrocarbon fraction containing at least about forty percent, by weight, dicyclopentadiene and minor amounts of dimethyldicyclopentadiene and codimers of cyclopentadiene and methylcyclopentadiene; (b) from about five to about forty percent, by weight, of at least one hydrocarbon selected from the group consisting of mono-olefins, diolefins, and polyenes each having more than five carbon atoms, and having no aromatic rings; and (c) from about five to about thirty percent, by weight, of at least one member selected from the group consisting of fatty acid-containing materials and rosin acid-containing materials.

Claim 36

A process for producing the composition of claim 30, in a reacted form, comprising reacting: (a) from about forty to about eighty-five percent, by weight, of dicyclopentadiene or a dicyclopentadiene-rich hydrocarbon fraction containing at least about forty percent, by weight, dicyclopentadiene and minor amounts of dimethyldicyclopentadiene and codimers and cyclopentadiene and methylcyclopentadiene; (b) from about five to about forty percent, by weight, of at least one hydrocarbon selected from the group consisting of mono-olefins, diolefins, and polyenes each having more than five carbon atoms, and having no aromatic rings; (c) from about five to about thirty percent, by weight, of at least one member selected from the group consisting of fatty acid-containing materials and rosin acid-containing materials; and (d) from about one to about ten percent, by weight, maleic anhydride.

Claim 37

A composition consisting essentially of: (a) a predominant amount of dicyclopentadiene; and lesser amounts of (b) at least one hydrocarbon selected from the group consisting of mono-olefins, diolefins, and polyenes each having more than five carbon atoms, and having no aromatic rings; and (c) at least one member selected from the group consisting of fatty acid-containing materials and rosin acid-containing materials.

Claim 38

A composition consisting essentially of: (a) a predominant amount of dicyclopentadiene; and lesser amounts of (b) at least one hydrocarbon selected from the group consisting of mono-olefins, diolefins, and polyenes each having more than five carbon atoms, and having no aromatic rings; and (c) at least one member selected from the group consisting of fatty acid-containing materials and rosin acid-containing materials.

Claim 39

The composition of claim 33 consisting essentially of: (a) from about forty to about eighty-five percent, by weight, of dicyclopentadiene or a dicyclopentadiene-rich hydrocarbon fraction containing at least about forty percent, by weight, dicyclopentadiene and minor amounts of dimethyldicyclopentadiene and codimers of cyclopentadiene and methylcyclopentadiene; (b) from about five to about forty percent, by weight, of at least one hydrocarbon selected from the group consisting of mono-olefins, diolefins, and polyenes each having more than five carbon atoms, and having no aromatic rings; and (c) from about five to about thirty percent, by weight, of at least one member selected from the group consisting of fatty acid-containing materials and rosin acid-containing materials.

Claim 40

A process for producing the composition of claim 33, in a reacted form, consisting essentially of reacting: (a) a predominant amount of dicyclopentadiene; and lesser amounts of (b) at least one hydrocarbon selected from the group consisting of mono-olefins, diolefins, and polyenes each having more than five carbon atoms, and having no aromatic rings; and (c) at least one member selected from the group consisting of fatty acid-containing materials and rosin acid-containing materials.

Claim 41

A composition consisting essentially of: (a) a predominant amount of dicyclopentadiene; and lesser amounts of (b) at least one hydrocarbon selected from the group consisting of mono-olefins, diolefins, and polyenes each having more than 5 carbon atoms, and having no aromatic rings; (c) at least one member selected from the group consisting of fatty acid-containing materials and rosin acid-containing materials; and (d) at least one ethylenically unsaturated lower aliphatic dicarboxylic acid or anhydride.

Claim 42

A composition consisting essentially of: (a) a predominant amount of dicyclopentadiene; and lesser amounts of (b) at least one hydrocarbon selected from the group consisting of mono-olefins, diolefins, and polyenes each having more than 5 carbon atoms, and having no aromatic rings; (c) at least one member selected from the group consisting of fatty acid-containing materials and rosin acid-containing materials; and (d) at least one ethylenically unsaturated lower aliphatic dicarboxylic acid or anhydride.

Claim 43

The composition of claim 36 consisting essentially of: (a) from about forty to about eighty-five percent, by weight, of dicyclopentadiene or a dicyclopentadiene-rich hydrocarbon fraction containing at least about forty percent, by weight, dicyclopentadiene and minor amounts of dimethyldicyclopentadiene and codimers of cyclopentadiene and methylcyclopentadiene; (b) from about five to about forty percent, by weight, of at least one hydrocarbon selected from the group consisting of mono-olefins, diolefins, and polyenes each having more than five carbon atoms, and having no aromatic rings; (c) from about five to about thirty percent, by weight, of at least one member selected from the group consisting of fatty acid-containing materials and rosin-acid containing materials; and (d) from about one to about ten percent, by weight, maleic anhydride.

Claim 44

A process for producing the composition of claim 36, in a reacted form, consisting essentially of reacting: (a) a predominant amount of dicyclopentadiene; and lesser amounts of (b) at least one hydrocarbon selected from the group consisting of mono-olefins, diolefins, and polyenes each having no more than 5 carbon atoms, and having no aromatic rings; (c) at least one member selected from the group consisting of fatty acid-containing materials and rosin acid-containing materials; and (d) at least one ethylenically unsaturated lower aliphatic dicarboxylic acid or anhydride.

Claim 45

The composition of claim 33 wherein component (b) is a mono-olefin selected from the group consisting of acyclic mono-olefins (alpha olefins); acyclic mono-olefins (non alpha olefins); simple cyclic mono-olefins; bicyclic mono-olefins; bicyclic mono-olefins (Spiro type); and polycyclic mono-olefins: four types.

Claim 46

The composition of claim 36 wherein component (b) is a mono-olefin selected from the group consisting of acyclic mono-olefins (alpha olefins); acyclic mono-olefins (non alpha olefins); simple cyclic mono-olefins; bicyclic mono-olefins (Spiro type); and polycyclic mono-olefins: four types.