US4070416A
Expired / Lapsed
US
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Novel thermosetting resin and a process for producing same
Assignee: Hitachi Ltd
•
Filing: 1975-08-18
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Granted: 1978-01-24
•
Expires: 1995-08-18
Abstract
Abstract A novel thermosetting resin can be obtained by mixing 1 equivalent or more of a polyfunctional isocyanate per 1 equivalent of a polyfunctional epoxide and then carrying out a polymerization reaction of the mixture in the presence of the catalyst which forms isocyanurate rings and oxazolidone rings so as to enable the mixture to form 2 or more isocyanurate rings directly connected with oxazolidone rings through an isocyanate residues.
Inventors
- 👤 Toshikazu Narahara
- 👤 Katuo Sugawara
- 👤 Yoshiharu Karasawa
- 👤 Hitoshi Yokono
- 👤 Junji Mukai
- 👤 Tadashi Muroi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 17:18
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/77; C08G18/78; C08G18/79; C08G18/791; C08G18/003; C08G59/00; C08G59/18; C08G59/40; C08G59/4007; C08G59/4014; C08G59/4028; C08G69/00; C08G69/02; C08G69/04; C08G69/06; C08G2115/00; C08G2115/02
Claims Analysis
Total Claims: 55
Claim 1
Independent Claim
117 words
A resin composition comprising 1 equivalent of an epoxide having 2 or more of vicinal epoxy groups, 2 equivalents or more of an organic polyisocyanate and 0.01 to 10% by weight of catalyst for forming isocyanurate rings and oxazolidone rings based on the total amount of the epoxide and isocyanate, whereby a thermosetting resin containing as a recurring unit 2 or more isocyanurate rings each being connected through an organic isocyanate residue and an oxazolidone ring connected at one side through an isocyanate residue to an organic isocyanurate and having at the other side an epoxy residue is provided by heating at a temperature higher than 80° C at which isocyanurate rings and oxazolidone rings are formed.
Claim 2
Dependent Claim
117 words
A resin composition comprising 1 equivalent of an epoxide having 2 or more of vicinal epoxy groups, 2 equivalents or more of an organic polyisocyanate and 0.01 to 10% by weight of catalyst for forming isocyanurate rings and oxazolidone rings based on the total amount of the epoxide and isocyanate, whereby a thermosetting resin containing as a recurring unit 2 or more isocyanurate rings each being connected through an organic isocyanate residue and an oxazolidone ring connected at one side through an isocyanate residue to an organic isocyanurate and having at the other side an epoxy residue is provided by heating at a temperature higher than 80° C at which isocyanurate rings and oxazolidone rings are formed.
Claim 3
Dependent Claim
119 words
A resin composition comprising 1 equivalent of an epoxide having 2 or more of vicinal epoxy groups, 2 equivalent or more of an organic diisocyanate and 0.01 to 10% by weight of a catalyst for forming isocyanurate rings and oxazolidone rings based on the total amount of the epoxide and isocyanate, whereby a thermosetting resin containing as a recurring unit 2 or more isocyanurate rings each being connected through an organic isocyanate residue and an oxazolidone ring connected at one side through an organic isocyanate residue to an isocyanurate ring and having at the other side an epoxy residue is provided by heating at a temperature higher than 80° C at which isocyanurate rings and oxazolidone rings are formed.
Claim 4
Dependent Claim
119 words
A resin composition comprising 1 equivalent of an epoxide having 2 or more of vicinal epoxy groups, 2 equivalent or more of an organic diisocyanate and 0.01 to 10% by weight of a catalyst for forming isocyanurate rings and oxazolidone rings based on the total amount of the epoxide and isocyanate, whereby a thermosetting resin containing as a recurring unit 2 or more isocyanurate rings each being connected through an organic isocyanate residue and an oxazolidone ring connected at one side through an organic isocyanate residue to an isocyanurate ring and having at the other side an epoxy residue is provided by heating at a temperature higher than 80° C at which isocyanurate rings and oxazolidone rings are formed.
Claim 5
Dependent Claim
27 words
The resin composition as defined in claim 1, wherein the epoxide is at least one member selected from the group consisting of bifunctional epoxides and trifunctional epoxides.
Claim 6
Dependent Claim
31 words
The resin composition as defined in claim 1, wherein the epoxide is at least one member selects from the group consisting of diglycidylether of bisphenol A and polyglycidylether of phenol-formaldehyde novolac.
Claim 7
Dependent Claim
24 words
The resin composition as defined in claim 1, wherein the polyisocyanate is at least one member selected from the group consisting of organic diisocyanates.
Claim 8
Dependent Claim
30 words
The resin composition as defined in claim 1, wherein the polyisocyanate is at least one member delected from the group consisting of 4,4'-diphenylmethane diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate and naphthalene-1,5-diisocyanate.
Claim 9
Dependent Claim
61 words
The resin composition as defined in claim 1, wherein the catalyst is at least one member selected from the group consisting of tertiary amines, N-substituted morpholine derivatives having an alkyl, an alkaryl, an aralkyl, a cyano-alkylene or a morpholinoalkylene group as a substituent and imidazole derivatives having an alkyl, cyano-alkylene or triazino-alkylene group at any of 1-, 2- or 4-substitution positions.
Claim 10
Dependent Claim
27 words
The resin composition as defined in claim 1, wherein the catalyst is at least one member selected from the group consisting of N-methylmorpholine, 2-phenylimidazole, 1-cyanoethyl-2-phenylimidazole and 2,4-diamino-6-(2'-undecylimidazolyl-1'-)ethyl-s-triazine.
Claim 11
Dependent Claim
24 words
The resin composition as defined in claim 1, wherein 2 to 5 equivalents of the polyisocyanate per 1 equivalent of the epoxide are used.
Claim 12
Dependent Claim
24 words
The resin composition as defined in claim 1, wherein 2 to 3.5 equivalents of the polyisocyanate per 1 equivalent of the epoxide are used.
Claim 13
Dependent Claim
22 words
The resin composition as defined in claim 1, wherein the resin composition is admixed with an organic solvent which dissolves said composition.
Claim 14
Dependent Claim
145 words
A process for producing a thermosetting resin, which comprises heating a resin composition comprising 1 equivalent of an epoxide having 2 or more of vicinal epoxy groups, equivalents or more of an organic polyisocyanate and 0.01 to 10% by weight of a catalyst for forming an isocyanurate ring and oxazolidone ring based on the total amount of the epoxide and organic isocyanate to carry out a trimerization reaction of the isocyanate, and then allowing the trimerized isocyanate to react with the epoxide, whereby a thermosetting resin containing as a recurring unit 2 or more isocyanurate rings each being connected through an isocyanate residue and an oxazolidone ring connected at one side through an isocyanate residue ring and having at the other side an epoxy residue is provided by heating at a temperature greater than 80° C at which isocyanurate rings and oxazolidone rings are formed.
Claim 15
Dependent Claim
145 words
A process for producing a thermosetting resin, which comprises heating a resin composition comprising 1 equivalent of an epoxide having 2 or more of vicinal epoxy groups, equivalents or more of an organic polyisocyanate and 0.01 to 10% by weight of a catalyst for forming an isocyanurate ring and oxazolidone ring based on the total amount of the epoxide and organic isocyanate to carry out a trimerization reaction of the isocyanate, and then allowing the trimerized isocyanate to react with the epoxide, whereby a thermosetting resin containing as a recurring unit 2 or more isocyanurate rings each being connected through an isocyanate residue and an oxazolidone ring connected at one side through an isocyanate residue ring and having at the other side an epoxy residue is provided by heating at a temperature greater than 80° C at which isocyanurate rings and oxazolidone rings are formed.
Claim 16
Dependent Claim
148 words
A process for producing a thermosetting resin which comprises heating a resin composition comprising 1 equivalent of an epoxide having 2 or more of vicinal epoxy groups, 2 equivalents or more of an organic diisocyanate and 0.01 to 10% by weight of a catalyst for forming an isocyanurate ring and oxazolidone ring based on the total amount of the epoxide and isocyanate to carry out a trimerization reaction of the isocyanate, and then allowing the trimerized isocyanate to react with the epoxide, whereby a thermosetting resin containing as a recurring unit 2 or more isocyanurate rings each being connected through an isocyanate residue and an oxazolidone ring connected at one side through an isocyanate residue to an isocyanurate ring and having at the other side an epoxy residue is provided by heating at a temperature higher than 80° C at which isocyanurate rings and oxazolidone rings are formed.
Claim 17
Dependent Claim
148 words
A process for producing a thermosetting resin which comprises heating a resin composition comprising 1 equivalent of an epoxide having 2 or more of vicinal epoxy groups, 2 equivalents or more of an organic diisocyanate and 0.01 to 10% by weight of a catalyst for forming an isocyanurate ring and oxazolidone ring based on the total amount of the epoxide and isocyanate to carry out a trimerization reaction of the isocyanate, and then allowing the trimerized isocyanate to react with the epoxide, whereby a thermosetting resin containing as a recurring unit 2 or more isocyanurate rings each being connected through an isocyanate residue and an oxazolidone ring connected at one side through an isocyanate residue to an isocyanurate ring and having at the other side an epoxy residue is provided by heating at a temperature higher than 80° C at which isocyanurate rings and oxazolidone rings are formed.
Claim 18
Dependent Claim
25 words
The process according to claim 13, wherein the epoxide is at least one member selected from the group consisting of bifunctional epoxides and trifunctional epoxides.
Claim 19
Dependent Claim
29 words
The process according to claim 13, wherein the epoxide is at least one member selected from the group consisting of diglycidylether of bisphenol A and polyglycidylether of phenol-formaldehyde novolac.
Claim 20
Dependent Claim
23 words
The process according to claim 13, wherein the polyisocyanate is at least one member selected from the group consisting of diisocyanates and triisocyanates.
Claim 21
Dependent Claim
28 words
The process according to claim 13, wherein the polyisocyanate is at least one member selected from the group consisting of 4,4'-diphenylmethane diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate and naphthalene-1,5-diisocyanate.
Claim 22
Dependent Claim
59 words
The process according to claim 13, wherein the catalyst is at least one member selected from the group consisting of teriary amines, N-substituted morpholine derivatives having an alkyl, an alkaryl, an aralkyl, a cyano-alkylene, or a morpholino-alkylene group as a substituent and imidazole derivatives having an alkyl, cyano-alkylene or triazino-alkylene group at any of 1-, 2-, or 4-substitution positions.
Claim 23
Dependent Claim
25 words
The process according to claim 13, wherein the catalyst is at least one member selected from the group consisting of N-methylmorpholine, 2-phenylimidazole, 1-cyanoethyl-2-phenylimidazole and 2,4-diamino-6-(2'-undecylimidazolyl-1'-)ethyl-s-triazine.
Claim 24
Dependent Claim
30 words
The process according to claim 13, wherein 2 to 5 equivalents of the polyisocyanate per 1 equivalent of the epoxide having 2 or more of vicinal epoxy groups are used.
Claim 25
Dependent Claim
22 words
The process according to claim 13, wherein 2 to 3.5 equivalents of the polyisocyanate per 1 equivalent of the epoxide are used.
Claim 26
Dependent Claim
17 words
The process according to claim 13, wherein the heating is carried out at 80° to 250° C.
Claim 27
Dependent Claim
104 words
A process for producing a thermosetting resin which comprises (a) heating a resin composition comprising 1 equivalent of an epoxide having two or more vicinal epoxy groups, 2 equivalents or more of an organic polyisocyanate and 0.01 to 10% by weight of a catalyst for forming isocyanurate rings and oxazolidone rings based on the total amount of the epoxide and organic isocyanate at a temperature sufficient to carry out a trimerization reaction of the isocyanate so that isocyanurate bonds are predominantly formed, and (b) subsequently heating said composition at a temperature so that oxazolidone bonds are formed so that said resin is threedimensionally cross-linked.
Claim 28
Dependent Claim
104 words
A process for producing a thermosetting resin which comprises (a) heating a resin composition comprising 1 equivalent of an epoxide having two or more vicinal epoxy groups, 2 equivalents or more of an organic polyisocyanate and 0.01 to 10% by weight of a catalyst for forming isocyanurate rings and oxazolidone rings based on the total amount of the epoxide and organic isocyanate at a temperature sufficient to carry out a trimerization reaction of the isocyanate so that isocyanurate bonds are predominantly formed, and (b) subsequently heating said composition at a temperature so that oxazolidone bonds are formed so that said resin is threedimensionally cross-linked.
Claim 29
Dependent Claim
20 words
The process of claim 23, wherein said resin composition consists essentially of said epoxide, said organic polyisocyanate and said catalyst.
Claim 30
Dependent Claim
18 words
The process of claim 24, wherein said composition consists of said epoxide, said organic polyisocyanate and said catalyst.
Claim 31
Dependent Claim
26 words
The process of claim 24, wherein said composition is heated to a temperature of about 130° C or lower for the formation of said isocyanurate rings.
Claim 32
Dependent Claim
25 words
The process of claim 26, wherein said composition is heated at a temperature of greater than 130° C for the formation of said oxazolidone rings.
Claim 33
Dependent Claim
26 words
The process of claim 23, wherein said composition is heated to a temperature of about 130° C or lower for the formation of said isocyanurate rings.
Claim 34
Dependent Claim
25 words
The process of claim 28, wherein said composition is heated at a temperature of greater than 130° C for the formation of said oxazolidone rings.
Claim 35
Dependent Claim
102 words
A resin produced by the process comprising (a) heating a resin composition comprising 1 equivalent of an epoxide having two or more vicinal epoxy groups, 2 equivalents or more of an organic polyisocyanate and 0.01 to 10% by weight of a catalyst for forming isocyanurate rings and oxazolidone rings based on the total amount of the epoxide and organic polyisocyanate at a temperature sufficient to carry out a trimerization reaction of the isocyanate so that isocyanurate bonds are predominantly formed, and (b) subsequently heating said composition at a temperature so that oxazolidone bonds are formed so that said resin is three-dimensionally cross-linked.
Claim 36
Dependent Claim
102 words
A resin produced by the process comprising (a) heating a resin composition comprising 1 equivalent of an epoxide having two or more vicinal epoxy groups, 2 equivalents or more of an organic polyisocyanate and 0.01 to 10% by weight of a catalyst for forming isocyanurate rings and oxazolidone rings based on the total amount of the epoxide and organic polyisocyanate at a temperature sufficient to carry out a trimerization reaction of the isocyanate so that isocyanurate bonds are predominantly formed, and (b) subsequently heating said composition at a temperature so that oxazolidone bonds are formed so that said resin is three-dimensionally cross-linked.
Claim 37
Dependent Claim
19 words
The resin of claim 30, wherein said composition consists essentially of said epoxide, said organic polyisocyanate and said catalyst.
Claim 38
Dependent Claim
18 words
The resin of claim 31, wherein said composition consists of said epoxide, said organic polyisocyanate and said catalyst.
Claim 39
Dependent Claim
26 words
The resin of claim 30, wherein said composition is heated to a temperature of about 130° C or lower for the formation of said isocyanurate rings.
Claim 40
Dependent Claim
26 words
The resin of claim 33, wherein said composition is thereafter heated at a temperature of greater than 130° C for the formation of said oxazolidone rings.
Claim 41
Dependent Claim
26 words
The resin of claim 31, wherein said composition is heated to a temperature of about 130° C or lower for the formation of said isocyanurate rings.
Claim 42
Dependent Claim
26 words
The resin of claim 35, wherein said composition is thereafter heated at a temperature of greater than 130° C for the formation of said oxazolidone rings.
Claim 43
Dependent Claim
123 words
A resin composition capable of forming a thermoset resin containing as a recurring unit 2 or more isocyanurate rings each being connected through an organic isocyanate residue and an oxazolidone ring connected at one side through an organic isocyanate residue through an isocyanurate ring and having at the other side an epoxy residue by heating at a temperature higher than 80° C at which isocyanurate rings and oxazolidone rings are formed, said resin composition consisting essentially of 1 equivalent of an epoxide having 2 or more vicinal epoxy groups, 2 equivalents or more of an organic polyisocyanate and 0.01 to 10% by weight of a catalyst for forming isocyanurate rings and oxazolidone rings based on the total amount of the epoxide and isocyanate.
Claim 44
Dependent Claim
123 words
A resin composition capable of forming a thermoset resin containing as a recurring unit 2 or more isocyanurate rings each being connected through an organic isocyanate residue and an oxazolidone ring connected at one side through an organic isocyanate residue through an isocyanurate ring and having at the other side an epoxy residue by heating at a temperature higher than 80° C at which isocyanurate rings and oxazolidone rings are formed, said resin composition consisting essentially of 1 equivalent of an epoxide having 2 or more vicinal epoxy groups, 2 equivalents or more of an organic polyisocyanate and 0.01 to 10% by weight of a catalyst for forming isocyanurate rings and oxazolidone rings based on the total amount of the epoxide and isocyanate.
Claim 45
Dependent Claim
11 words
The composition of claim 37, wherein said polyisocyanate is a diisocyanate.
Claim 46
Dependent Claim
24 words
The composition of claim 37, wherein the epoxide is at least one member selected from the group consisting of bifunctional epoxides and trifunctional epoxides.
Claim 47
Dependent Claim
28 words
The composition of claim 37, wherein the epoxide is at least one member selected from the group consisting of diglycidylether is bisphenol A and polyglycidylether of phenolformaldehyde novolac.
Claim 48
Dependent Claim
22 words
The composition of claim 37, wherein the organic polyisocyanate is at least one member selected from the group consisting of organic diisocyanates.
Claim 49
Dependent Claim
29 words
The composition of claim 37, wherein the polyfunctional organic isocyanate is at least one member selected from the group consisting of 4,4'-diphenylmethane diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate and naphthalene-1,5-diisocyanate.
Claim 50
Dependent Claim
58 words
The composition of claim 37, wherein the catalyst is at least one member selected from the group consisting of tertiary amines, N-substituted morpholine derivatives having an alkyl, an alkaryl, an aralkyl, a cyano-alkylene, or a morpholino-alkylene group as a substituent and imidazole derivatives having an alkyl, cyano-alkylene or triazino-alkylene group at any of 1-, 2- or 4-substitution positions.
Claim 51
Dependent Claim
24 words
The composition of claim 37, wherein the catalyst is at least one member selected from the group consisting of N-methylmorpholine, 2-phenylimidazole, 1-cyanoethyl-2-phenylimidazole and 2,4-diamino-6-(2'-undecylimidazolyl-1'-)ethyl-s-triazine.
Claim 52
Dependent Claim
22 words
The composition of claim 37, wherein 2 to 5 equivalents of the organic polyisocyanate per 1 equivalent of the epoxide are used.
Claim 53
Dependent Claim
22 words
The composition of claim 37, wherein 2 to 3.5 equivalents of the organic polyisocyanate per 1 equivalent of the epoxide are used.
Claim 54
Dependent Claim
19 words
The composition of claim 37, wherein the resin composition is admixed with an organic solvent which dissolves said composition.
Claim 55
Dependent Claim
18 words
The composition of claim 37, wherein said composition consists of said epoxide, said organic polyisocyanate and said catalyst.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1981-01-23 | 1981-07-25 | 1982-01-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-01-23 | 1985-07-25 | 1986-01-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-01-23 | 1989-07-25 | 1990-01-24 | $7700.00 | Window Closed / Lapsed |