US4189548A
Expired / Lapsed
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Epoxy resin composition
Assignee: Mitsui Chemicals Inc
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Filing: 1978-04-25
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Granted: 1980-02-19
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Expires: 1998-04-25
Abstract
Abstract An epoxy resin composition comprising [A] a novel copolymer produced by polymerizing a polymerizable material selected from the group consisting of (a) substituted or unsubstituted dicyclopentadiene; (b) a cationically polymerizable unsaturated hydrocarbon-containing fraction obtained by distilling a cracking or reforming product of a petroleum and having a boiling point in the range of -20 DEG C. to 280 DEG C.; (c) a cationically polymerizable vinyl aromatic hydrocarbon having 8 to 10 carbon atoms; (d) a mixture of two or three of ingredients (a), (b) and (c); and (e) a mixture of any one of ingredients (a) to (d) with a cationically polymerizable unsaturated aliphatic hydrocarbon having 4 to 10 carbon atoms in the presence of a cationic polymerization catalyst with a high-boiling product having a boiling point of at least about 150 DEG C. and an oxygen content of at least 0.5% by weight being introduced into the polymerization system at any stage of the polymerization process or into the resulting polymer, the said high-boiling product being obtained as a by-product in a process comprising oxidizing a benzene or naphthalene ring-substituted with at least one isopropyl group to convert it to the corresponding hydroperoxide and then decomposing it with an acid to produce the corresponding phenol or naphthol; [B] a polyepoxy compound; and [C] a curing agent. This epoxy resin composition is useful for paints, adhesives, road-repairing materials, floor coverings, etc.
Inventors
- 👤 Takeshi Sakashita
- 👤 Ryoichi Miyamoto
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 06:58
CPC Classifications
C; C08; C08F; C08F32/00; C08F32/08; C08F12/00; C08F12/02; C08F12/04; C08F240/00
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
239 words
An epoxy resin composition comprising (A) a novel copolymer produced by polymerizing a polymerizable material selected from the group consisting of (a) substituted or unsubstituted dicyclopentadiene, (b) a cationically polymerizable unsaturated hydrocarbon-containing fraction obtained by distilling a cracking or reforming product of a petroleum and having a boiling point in the range of -20° C. to 280° C., (c) a cationically polymerizable vinyl aromatic hydrocarbon having 8 to 10 carbon atoms, (d) a mixture of two or three of ingredients (a), (b) and (c), and (e) a mixture of any one of ingredients (a) to (d) with a cationically polymerizable unsaturated aliphatic hydrocarbon having 4 to 10 carbon atoms in the presence of a cationic polymerization catalyst with a high-boiling product having a boiling point of at least about 150° C. and an oxygen content of at least 0.5% by weight being introduced into the polymerization system at any stage of the polymerization process or into the resulting polymer, the said high-boiling product being obtained as a residue, comprising a mixture of by-products, in a process comprising oxidizing a benzene or naphthalene ring-substituted with at least one isopropyl group to convert it to the corresponding hydroperoxide, decomposing the hydroperoxide with an acid to produce the corresponding phenol or naphthol, and separating the phenol or naphthol from the resultant reaction mixture to obtain said residue comprising a mixture of said by-products; (B) a polyepoxy compound; and (C) a curing agent.
Claim 2
Dependent Claim
239 words
An epoxy resin composition comprising (A) a novel copolymer produced by polymerizing a polymerizable material selected from the group consisting of (a) substituted or unsubstituted dicyclopentadiene, (b) a cationically polymerizable unsaturated hydrocarbon-containing fraction obtained by distilling a cracking or reforming product of a petroleum and having a boiling point in the range of -20° C. to 280° C., (c) a cationically polymerizable vinyl aromatic hydrocarbon having 8 to 10 carbon atoms, (d) a mixture of two or three of ingredients (a), (b) and (c), and (e) a mixture of any one of ingredients (a) to (d) with a cationically polymerizable unsaturated aliphatic hydrocarbon having 4 to 10 carbon atoms in the presence of a cationic polymerization catalyst with a high-boiling product having a boiling point of at least about 150° C. and an oxygen content of at least 0.5% by weight being introduced into the polymerization system at any stage of the polymerization process or into the resulting polymer, the said high-boiling product being obtained as a residue, comprising a mixture of by-products, in a process comprising oxidizing a benzene or naphthalene ring-substituted with at least one isopropyl group to convert it to the corresponding hydroperoxide, decomposing the hydroperoxide with an acid to produce the corresponding phenol or naphthol, and separating the phenol or naphthol from the resultant reaction mixture to obtain said residue comprising a mixture of said by-products; (B) a polyepoxy compound; and (C) a curing agent.
Claim 3
Dependent Claim
16 words
The composition of claim 1 wherein the substituted or unsubstituted dicyclopentadiene is dicyclopentadiene, methyldicyclopentadiene or dimethyldicyclopentadiene.
Claim 4
Dependent Claim
39 words
The composition of claim 1 wherein the substituted or unsubstituted dicyclopentadiene is crude substituted or unsubstituted dicyclopentadiene having a purity of at least 35% by weight and produced by the thermal dimerization of the corresponding substituted or unsubstituted cyclopentadiene.
Claim 5
Dependent Claim
37 words
The composition of claim 1 wherein the cationically polymerizable unsaturated hydrocarbon-containing fraction is a fraction composed mainly of C 8 -C 12 aromatic unsaturated hydrocarbons having a boiling point in the range of 140° to 280° C.
Claim 6
Dependent Claim
38 words
The composition of claim 1 wherein the cationically polymerizable unsaturated hydrocarbon-containing fraction is a fraction composed mainly of C 4 -C 5 aliphatic unsaturated hydrocarbons having a boiling point in the range of -20° C. to +100° C.
Claim 7
Dependent Claim
69 words
The composition of claim 1 wherein the cationically polymerizable unsaturated hydrocarbon-containing fraction is a mixture consisting of (1) a fraction composed mainly of C 4 -C 5 aliphatic unsaturated hydrocarbons having a boiling point in the range of -20° C. to 100° C. and (2) a fraction composed mainly of C 8 -C 12 aromatic unsaturated hydrocarbons having a boiling point in the range of 140° to 280° C.
Claim 8
Dependent Claim
36 words
The composition of claim 1 wherein the cationically polymerizable vinyl aromatic hydrocarbon is selected from the group consisting of styrene, α- and β-methylstyrenes, o-, m- and p-vinyltoluenes, o-, m- and p-isopropenyl toluenes, and mixtures of these.
Claim 9
Dependent Claim
33 words
The composition of claim 1 wherein the cationically polymerizable unsaturated aliphatic hydrocarbon is selected from the group consisting of butadiene, isoprene, piperylene, isobutylene, 2-butene, 2-methyl-1-butene, 2-methyl-2-butene, 1-pentene, 2-pentene, cyclopentene, and mixtures of these.
Claim 10
Dependent Claim
44 words
The composition of claim 1 wherein the cationically polymerizable unsaturated aliphatic hydrocarbon is mixed with any one of ingredients (a) to (d) in an amount of at most 80% by weight based on the weight of any one of the ingredients (a) to (d).
Claim 11
Dependent Claim
19 words
The composition of claim 1 wherein the high-boiling product has an oxygen content of 1 to 17% by weight.
Claim 12
Dependent Claim
19 words
The composition of claim 1 wherein the high-boiling product has a hydroxyl value of at least 10 mg KOH/g.
Claim 13
Dependent Claim
19 words
The composition of claim 1 wherein the high-boiling product has a hydroxyl value of 20 to 500 mg KOH/g.
Claim 14
Dependent Claim
29 words
The composition of claim 1 wherein the benzene ring-substituted with at least one isopropyl group is cumene, cymene or diisopropylbenzene, and the corresponding phenol is phenol, cresol or dihydroxybenzene.
Claim 15
Dependent Claim
35 words
The composition of claim 1 wherein the amount of the high-boiling product introduced is 5 to 200 parts by weight per 100 parts by weight of all the cationically polymerizable ingredients in the polymerizable material.
Claim 16
Dependent Claim
35 words
The composition of claim 1 wherein the amount of the high-boiling product introduced is 10 to 100 parts by weight per 100 parts by weight of all the cationically polymerizable ingredients in the polymerizable material.
Claim 17
Dependent Claim
21 words
The composition of claim 1 wherein the high-boiling product is introduced into the polymerization system before the initiation of the polymerization.
Claim 18
Dependent Claim
14 words
The composition of claim 1 wherein the cationic polymerization catalyst is a Friedel-Crafts catalyst.
Claim 19
Dependent Claim
20 words
The composition of claim 1 wherein the cationic polymerizable catalyst is boron trifluoride, a boron trifluoride complex, or aluminum trichloride.
Claim 20
Dependent Claim
19 words
The composition of claim 1 wherein the polymerization is carried out at a temperature of 0° to 200° C.
Claim 21
Dependent Claim
25 words
The composition of claim 1 wherein the polymer is liquid at room temperature, or solid with a softening point of not more than 200° C.
Claim 22
Dependent Claim
18 words
The composition of claim 1 wherein the polymer has an oxygen content of 0.5 to 15% by weight.
Claim 23
Dependent Claim
18 words
The composition of claim 1 wherein the polymer has a hydroxyl value of at least 1 mg KOH/g.
Claim 24
Dependent Claim
18 words
The composition of claim 1 wherein the polymer has a hydroxyl value of 1 to 400 mg KOH/g.
Claim 25
Dependent Claim
17 words
The composition of claim 1 wherein the polyepoxy compound has an epoxy equivalent of at most 5,000.
Claim 26
Dependent Claim
17 words
The composition of claim 1 wherein the polyepoxy compound has a molecular weight of 150 to 5,000.
Claim 27
Dependent Claim
25 words
The composition of claim 1 wherein the polyepoxy compound is selected from the group consisting of polyglycidyl ethers of polyphenol compounds and novolac-type polyepoxy compounds.
Claim 28
Dependent Claim
30 words
The composition of claim 1 wherein the amount of the novel polymer [A] is 5 to 1,500 parts by weight per 100 parts by weight of the polyepoxy compound [B].
Claim 29
Dependent Claim
37 words
The composition of claim 1 wherein the curing agent is a polyfunctional compound containing at least two functional groups selected from primary and secondary amino groups, acid anhydride groups, a mercapto group and a phenolic hydroxyl group.
Claim 30
Dependent Claim
38 words
The composition of claim 1 wherein the amount of the curing agent [C] is 0.2 to 200 parts by weight per 100 parts by weight of the sum of the novel polymer [A] and the polyepoxy compound [B].
Claim 31
Dependent Claim
20 words
The composition of claim 1 wherein the high-boiling product contains up to 10% by weight of said phenol or naphthol.
Claim 32
Dependent Claim
20 words
The composition of claim 1 wherein the high-boiling product contains up to 5% by weight of said phenol or naphthol.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-02-18 | 1983-08-20 | 1984-02-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-02-18 | 1987-08-20 | 1988-02-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-02-18 | 1991-08-20 | 1992-02-19 | $7700.00 | Window Closed / Lapsed |