Thermosetting composition, method of producing fusible thermosetting resin using same, and process for the production of condensed, polynuclear aromatic hydrocarbon resin using same

Claim 2

A thermosetting composition consisting essentially of: (i) a raw material containing one or more condensed polynuclear aromatic compounds having at least three condensed benzene rings, said raw material being selected from the group consisting of phenanthrene, anthracene, pyrene, chrysene, naphthacene, fluoranthene, perylene, picene, benzpyrenes, benzperylenes, and alkyl derivatives and mixtures thereof, and pitches having a softening point of 100°-200° C., an f a value of at least 0.6 and an H a value of at least 20%; (ii) a crosslinking agent containing an aromatic compound having at least two hydroxymethyl or halomethyl groups; and (iii) an acid catalyst; wherein the amounts of said raw material and said crosslinking agent are such as to satisfy the following condition: ##EQU6## where W 1 represents the weight of said raw material, W 2 represents the weight of said crosslinking agent, a represents the molecular weight or average molecular weight of said raw material, b represents the molecular weight or average molecular weight of said crosslinking agent and n is the number of the hydroxymethyl or halomethyl groups of said crosslinking agent.

Claim 3

A thermosetting composition according to claim 1, wherein said raw material is at least one compound selected from the group consisting of phenanthrene, anthracene, pyrene, chrysene, naphthacene, fluoranthene, perylene, picene, benzpyrenes, benzperylenes and alkyl derivatives thereof.

Claim 4

A thermosetting composition according to claim 2, wherein said raw material is a mixture of pyrene and phenanthrene.

Claim 5

A thermosetting composition according to claim 1, wherein said raw material is a pitch having a softening point of 10°-200° C., an f a value of at least 0.6 and an H a value of at least 20%.

Claim 6

A thermosetting composition according to claim 4, wherein said pitch is a coal-derived or petroleum-derived pitch.

Claim 7

A thermosetting composition according to claim 1, wherein said crosslinking agent is a member selected from the group consisting of di(hydroxymethyl)benzenes, di(hydroxymethyl)-naphthalenes, tri(hydroxymethyl) benzenes, tri(hydroxymethyl)-naphthalenes, di(halomethyl)benzenes, di(halomethyl)naphthalenes, tri(halomethyl)benzenes, tri(halomethyl)naphthalenes and alkyl derivatives thereof.

Claim 8

A thermosetting composition according to claim 6, wherein said crosslinking agent is p-di(hydroxymethyl)benzene or a dimethyldi (hydroxymethyl)benzene.

Claim 9

A thermosetting resin composition consisting essentially of a fusible product obtained by a method including the steps of: providing a mixture which comprises (i) a raw material containing one or more condensed polynuclear aromatic compounds having at least three condensed benzene rings, said raw material being selected from the group consisting of phenanthrene, anthracene, pyrene, chrysene, naphthacene, fluoranthene, perylene, picene, benzpyrenes, benzperylenes, and alkyl derivatives and mixtures thereof, and pitches having a softening point of 100°-200° C., an f a value of at least 0.6 and an H a value of at least 20%; (ii) a crosslinking agent containing an aromatic compound having at least two hydroxymethyl or halomethyl groups; and (iii) an acid catalyst; wherein the amounts of said raw material and said crosslinking agent are such as to satisfy the following condition: ##EQU7## where W 1 represents the weight of said raw material, W 2 represents the weight of said crosslinking agent, a represents the molecular weight or average molecular weight of said raw material, b represents the molecular weight or average molecular weight of said crosslinking agent and n is the number of the hydroxymethyl or halomethyl groups of said crosslinking agent, and reacting said mixture at a temperature sufficient to effect the crosslinking of said one or more condensed polynuclear aromatic compounds, thereby to obtain said fusible product.

Claim 10

A thermosetting resin composition consisting essentially of a fusible product obtained by a method including the steps of: providing a mixture which comprises (i) a raw material containing one or more condensed polynuclear aromatic compounds having at least three condensed benzene rings, said raw material being selected from the group consisting of phenanthrene, anthracene, pyrene, chrysene, naphthacene, fluoranthene, perylene, picene, benzpyrenes, benzperylenes, and alkyl derivatives and mixtures thereof, and pitches having a softening point of 100°-200° C., an f a value of at least 0.6 and an H a value of at least 20%; (ii) a crosslinking agent containing an aromatic compound having at least two hydroxymethyl or halomethyl groups; and (iii) an acid catalyst; wherein the amounts of said raw material and said crosslinking agent are such as to satisfy the following condition: ##EQU7## where W 1 represents the weight of said raw material, W 2 represents the weight of said crosslinking agent, a represents the molecular weight or average molecular weight of said raw material, b represents the molecular weight or average molecular weight of said crosslinking agent and n is the number of the hydroxymethyl or halomethyl groups of said crosslinking agent, and reacting said mixture at a temperature sufficient to effect the crosslinking of said one or more condensed polynuclear aromatic compounds, thereby to obtain said fusible product.

Claim 11

A thermosetting resin composition according to claim 8, wherein said raw material is at least one compound selected from the group consisting of phenanthrene, anthracene, pyrene, chrysene, naphthacene, fluoranthene, perylene, picene, benzpyrenes, benzperylenes and alkyl derivatives thereof.

Claim 12

A thermosetting resin composition according to claim 9, wherein said raw material is a mixture of pyrene and phenanthrene.

Claim 13

A thermosetting resin composition according to claim 8, wherein said raw material is a pitch having a softening point of 10°-200° C., an f a value of at least 0.6 and an H a value of at least 20%.

Claim 14

A thermosetting resin composition according to claim 11, wherein said pitch is a coal-derived or petroleum-derived pitch.

Claim 15

A thermosetting resin composition according to claim 8, wherein said crosslinking agent is a member selected from the group consisting of di(hydroxymethyl)benzenes, di(hydroxymethyl)-naphthalenes, tri(hydroxymethyl)benzenes, tri(hydroxymethyl)-naphthalenes, di(halomethyl)benzenes, di(halomethyl)naphthalenes, tri(halomethyl)benzenes, tri(halomethyl)naphthalenes and alkyl derivatives thereof.

Claim 16

A thermosetting resin composition according to claim 13, wherein said crosslinking agent is p-di(hydroxymethyl)benzene or a dimethyldi (hydroxymethyl)benzene.

Claim 19

A method according to claim 15, wherein said raw material is at least one compound selected from the group consisting of phenanthrene, anthracene, pyrene, chrysene, naphthacene, fluoranthene, perylene, picene, benzpyrenes, benzperylenes and alkyl derivatives thereof.

Claim 20

A method according to claim 15, wherein said raw material is a mixture of pyrene and phenanthrene.

Claim 21

A method according to claim 15, wherein said raw material is a pitch having a softening point of 10°-200° C., an f a value of at least 0.6 and an H a value of at least 20%.

Claim 22

A method according to claim 15, wherein said crosslinking agent is a member selected from the group consisting of di(hydroxymethyl)benzenes, di(hydroxymethyl)naphthalenes, tri(hydroxymethyl)benzenes, tri(hydroxymethyl)naphthanes, di(halomethyl)benzenes, di(halomethyl)naphthalenes, tri(halomethyl)benzenes, tri(halomethyl)naphthalanes and alkyl derivatives thereof.

Claim 23

A method according to claim 19, wherein said crosslinking agent is p-di(hydroxymethyl)benzene or a dimethyl-di(hydroxymethyl)benzene.

Claim 24

A method according to claim 18, wherein said pitch is a coal-derived or petroleum-derived pitch.

Claim 25

A method according to claim 15, wherein (W 2 /W 1 )×(a/b) is not smaller than 1.1/n (where W 1 , W 2 , a, b and n have the same meaning as above) and wherein said reaction of said mixture is stopped before completion of the reaction, whereby said thermosetting resin is hardened and becomes infusible upon a further heat treatment.

Claim 26

A method according to claim 15, wherein (W 2 /W 1 )×(a/b) is smaller than 1.0/n (where W 1 , W 2 , a, b and n have the same meaning as above) so that the amount of said crosslinking agent is insufficient to completely harden said mixture, said thermosetting resin capable of being completely hardened when heated together with an additional amount of said crosslinking agent.

Claim 27

A method according to claim 15, wherein the amount of said catalyst contained in said mixture is insufficient to completely effect the crosslinking, said thermosetting resin being capable of being completely hardened and becoming infusible when heated with an additional amount of said catalyst.

Claim 28

A method according to claim 15, wherein said reaction of said mixture is performed at a temperature of 70°-300° C.

Claim 29

A process for the production of a heat-resisting, condensed polynuclear aromatic hydrocarbon resin, consisting essentially of the steps of: providing a mixture containing: (i) a raw material containing one or more condensed polynuclear aromatic compounds having at least three condensed benzene rings, said raw material being selected from the group consisting of phenanthrene, anthracene, pyrene, chrysene, naphthacene, fluoranthene, perylene, picene, benzpyrenes, benzperylenes, and alkyl derivatives and mixtures thereof, and pitches having a softening point of 100°-200° C., an f a value of at least 0.6 and an H a value of at least 20%; (ii) a crosslinking agent containing an aromatic compound having at least two hydroxymethyl or halomethyl groups; and (iii) an acid catalyst; wherein the amounts of said raw material and said crosslinking agent are such as to satisfy the following condition: ##EQU9## where W 1 represents the weight of said raw material, W 2 represents the weight of said crosslinking agent, a represents the molecular weight or average molecular weight of said raw material, b represents the molecular weight or average molecular weight of said crosslinking agent and n is the number of the hydroxymethyl or halomethyl groups of said crosslinking agent, and reacting said mixture to form said heat-resisting, condensed polynuclear aromatic hydrocarbon resin as an infusible product.

Claim 30

A process for the production of a heat-resisting, condensed polynuclear aromatic hydrocarbon resin, consisting essentially of the steps of: providing a mixture containing: (i) a raw material containing one or more condensed polynuclear aromatic compounds having at least three condensed benzene rings, said raw material being selected from the group consisting of phenanthrene, anthracene, pyrene, chrysene, naphthacene, fluoranthene, perylene, picene, benzpyrenes, benzperylenes, and alkyl derivatives and mixtures thereof, and pitches having a softening point of 100°-200° C., an f a value of at least 0.6 and an H a value of at least 20%; (ii) a crosslinking agent containing an aromatic compound having at least two hydroxymethyl or halomethyl groups; and (iii) an acid catalyst; wherein the amounts of said raw material and said crosslinking agent are such as to satisfy the following condition: ##EQU9## where W 1 represents the weight of said raw material, W 2 represents the weight of said crosslinking agent, a represents the molecular weight or average molecular weight of said raw material, b represents the molecular weight or average molecular weight of said crosslinking agent and n is the number of the hydroxymethyl or halomethyl groups of said crosslinking agent, and reacting said mixture to form said heat-resisting, condensed polynuclear aromatic hydrocarbon resin as an infusible product.

Claim 31

A process according to claim 26, wherein said reaction is conducted so that said infusible product is substantially insoluble in organic solvents.

Claim 32

A process according to claim 26, wherein said reaction is performed at a temperature of 70°-350° C.

Claim 33

A process according to claim 28, wherein said reaction step includes the substeps of: (i) heating said mixture at a temperature of 70°-300° C. to obtain a fusible intermediate condensation product which is insoluble in n-hexane but is soluble in quinoline; (ii) heating said intermediate condensation product at a temperature of 100°-200° C. to obtain an infusible resin containing only a small amount of components soluble in quinoline; and (iii) heating said infusible resin at a temperature of 150°-350° C. to obtain said heat-resisting, condensed polynuclear aromatic hydrocarbon resin as an infusible product which is insoluble in quinoline.

Claim 34

A process according to claim 29, wherein said sub-step (ii) is conducted while contacting said intermediate condensation product with an aggregate material.

Claim 35

A process for the production of a heat-resisting, condensed polynuclear aromatic hydrocarbon resin, consisting essentially of the steps of: providing a mixture containing (i) a raw material containing one or more condensed polynuclear aromatic compounds having at least three condensed benzene rings, said raw material being selected from the group consisting of phenanthrene, anthracene, pyrene, chrysene, naphthacene, fluoranthene, perylene, picene, benzpyrenes, benzperylenes, and alkyl derivatives and mixtures thereof, and pitches having a softening point of 100°-200° C., an f a value of at least 0.6 and an H a value of at least 20%; (ii) a crosslinking agent selected from the group consisting of aromatic compounds having two hydroxymethyl groups and aromatic compounds having two halomethyl groups and (iii) an acid catalyst, wherein the amounts of said raw material and said crosslinking agent are such as to satisfy the following condition: ##EQU10## where W 1 represents the weight of said raw material, W 2 ' represents the weight of said crosslinking agent, a represents the molecular weight or average weight of said raw material and b represents the molecular weight of said crosslinking agent; reacting said mixture at a temperature of 70°-300° C. to obtain a fusible product; admixing said fusible product with the crosslinking agent in an amount satisfying the following condition: ##EQU11## where W 1 , W 2 ', a and b have the same meaning as above and W 2 " represents the amount of said crosslinking agent additionally added to said fusible product; and reacting said admixture at a temperature of 70°-350° C. to obtain said heat-resisting, condensed polynuclear aromatic hydrocarbon resin as an infusible product.

Claim 36

A process for the production of a heat-resisting, condensed polynuclear aromatic hydrocarbon resin, consisting essentially of the steps of: providing a mixture containing (i) a raw material containing one or more condensed polynuclear aromatic compounds having at least three condensed benzene rings, said raw material being selected from the group consisting of phenanthrene, anthracene, pyrene, chrysene, naphthacene, fluoranthene, perylene, picene, benzpyrenes, benzperylenes, and alkyl derivatives and mixtures thereof, and pitches having a softening point of 100°-200° C., an f a value of at least 0.6 and an H a value of at least 20%; (ii) a crosslinking agent selected from the group consisting of aromatic compounds having two hydroxymethyl groups and aromatic compounds having two halomethyl groups and (iii) an acid catalyst, wherein the amounts of said raw material and said crosslinking agent are such as to satisfy the following condition: ##EQU10## where W 1 represents the weight of said raw material, W 2 ' represents the weight of said crosslinking agent, a represents the molecular weight or average weight of said raw material and b represents the molecular weight of said crosslinking agent; reacting said mixture at a temperature of 70°-300° C. to obtain a fusible product; admixing said fusible product with the crosslinking agent in an amount satisfying the following condition: ##EQU11## where W 1 , W 2 ', a and b have the same meaning as above and W 2 " represents the amount of said crosslinking agent additionally added to said fusible product; and reacting said admixture at a temperature of 70°-350° C. to obtain said heat-resisting, condensed polynuclear aromatic hydrocarbon resin as an infusible product.

Claim 37

A thermosetting resin composition according to claim 8, further consisting essentially of an aggregate selected from glass fibers, carbon fibers and ceramics.

Claim 38

A method according to claim 15, wherein said reaction is performed at a temperature of 70°-300° C.