Patent US2962922A successfully refreshed from Google Patents.
US4048147A
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Carboxylic acid of cyclopentadiene derivative, salt thereof, or ester thereof and process for producing these compositions
Assignee: JSR Corp
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Filing: 1975-11-26
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Granted: 1977-09-13
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Expires: 1995-11-26
Abstract
Abstract A novel compound represented by the formula, ##STR1## WHEREIN R is a hydrogen or an alkyl group having 1 to 3 carbon atoms, said four R's being the same or different; R 1 is hydrogen, an alkali metal, an ammonium group, a mono-to tetra-hydric aliphatic alcohol moiety having 1 to 12 carbon atoms, or an organic amine residue; n is an integer of 1 to 4; and R 2 , R 3 , R 4 , R 5 and R 6 are independently hydrogen or alkyl groups having 1 to 6 carbon atoms or R 2 and R 3 may form a ring when taken together. Said novel compound has properties similar to those of natural rosin or a disproportionated rosin, and is useful as a vehicle for coating compositions and printing inks, as an emulsifier for emulsion polymerization, and as a sizing agent.
Inventors
- 👤 Masatoshi Arakawa
- 👤 Ryotaro Ohno
- 👤 Katuhiro Ishikawa
- 👤 Noboru Yamahara
- 👤 Hisashi Matsui
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 00:10
CPC Classifications
C; C07; C07C; C07C61/00; C07C61/16; C07C61/39; C07C45/00; C07C45/49; C07C45/50
Claims Analysis
Total Claims: 40
Claim 1
Independent Claim
117 words
A composition represented by the formula, ##STR6## wherein R is hydrogen or an alkyl group having 1 to 3 carbon atoms, said four R groups being the same or different; R 1 is hydrogen, a mono- to tetra-hydric aliphatic alcohol moiety having 1 to 12 carbon atoms, an alkali or alkaline earth metal, an ammonium group, or an organic amine residue; n is an integer of 1 to 4; and R 2 , R 3 , R 4 , R 5 and R 6 , which may be the same or different, are independently hydrogen or alkyl groups having 1 to 6 carbon atoms, or R 2 and R 3 may form a ring when taken together.
Claim 2
Dependent Claim
117 words
A composition represented by the formula, ##STR6## wherein R is hydrogen or an alkyl group having 1 to 3 carbon atoms, said four R groups being the same or different; R 1 is hydrogen, a mono- to tetra-hydric aliphatic alcohol moiety having 1 to 12 carbon atoms, an alkali or alkaline earth metal, an ammonium group, or an organic amine residue; n is an integer of 1 to 4; and R 2 , R 3 , R 4 , R 5 and R 6 , which may be the same or different, are independently hydrogen or alkyl groups having 1 to 6 carbon atoms, or R 2 and R 3 may form a ring when taken together.
Claim 3
Dependent Claim
14 words
The composition according the claim 1, wherein all of said R groups are hydrogen
Claim 4
Dependent Claim
17 words
The composition according to claim 1, wherein R 1 is an alkali metal, and n is 1.
Claim 5
Dependent Claim
13 words
The composition according to claim 3, wherein R 1 is potassium or sodium.
Claim 6
Dependent Claim
18 words
The composition according to claim 1, wherein R 1 is an alkaline earth metal, and n is 2.
Claim 7
Dependent Claim
14 words
The composition according to claim 5, wherein R 1 is calcium, zinc or magnesium.
Claim 8
Dependent Claim
29 words
The composition according to claim 1, wherein R 2 is hydrogen or an alkyl group having 1 to 4 carbon atoms and R 3 to R 6 are hydrogen.
Claim 9
Dependent Claim
24 words
The composition according to claim 1, wherein both R 2 and R 3 are methyl groups and R 4 to R 6 are hydrogen.
Claim 10
Dependent Claim
23 words
The composition according to claim 2, wherein R 2 is hydrogen or a methyl group and R 3 to R 6 are hydrogen.
Claim 11
Dependent Claim
23 words
The composition according to claim 1, wherein R 1 is a mono- to tetra-hydric aliphatic alcohol moiety having 1 to 12 carbon atoms.
Claim 12
Dependent Claim
15 words
The composition according to claim 10, wherein R 1 is a glycerin or pentaerythritol moiety.
Claim 13
Dependent Claim
11 words
The composition according to claim 11, wherein all R's are hydrogen.
Claim 14
Dependent Claim
22 words
The composition according to claim 1, wherein R 1 is an ammonium group or an organic amine residue, and n is 1.
Claim 15
Dependent Claim
70 words
A composition represented by the formula, ##STR7## wherein R is hydrogen or an alkyl group having 1 to 3 carbon atoms, said four R groups being the same or different; R 1 is hydrogen, a mono- to tetra-hydric aliphatic alcohol moiety having 1 to 12 carbon atoms, an alkali or alkaline earth metal, an ammonium group, or an organic amine residue; and n is an integer of 1 to 4.
Claim 16
Dependent Claim
70 words
A composition represented by the formula, ##STR7## wherein R is hydrogen or an alkyl group having 1 to 3 carbon atoms, said four R groups being the same or different; R 1 is hydrogen, a mono- to tetra-hydric aliphatic alcohol moiety having 1 to 12 carbon atoms, an alkali or alkaline earth metal, an ammonium group, or an organic amine residue; and n is an integer of 1 to 4.
Claim 17
Dependent Claim
205 words
A process for producing a composition represented by the formula, ##STR8## wherein R is hydrogen or an alkyl group having 1 to 3 carbon atoms, said four R groups being the same or different; R 1 is hydrogen, a mono- to tetra-hydric aliphatic alcohol moiety having 1 to 12 carbon atoms, an alkali or alkaline earth metal, ammonium group, or an organic amine residue; n is an integer of 1 to 4; and R 2 , R 3 , R 4 , R 5 and R 6 , which may be the same or different, are independently hydrogen or alkyl groups having 1 to 6 carbon atoms or R 2 and R 3 may form a ring when taken together, which comprises reacting a carboxylic ester of a dimer of at least one member selected from the group consisting of cyclopentadiene and mono- to di-alkyl (C 1-3 ) cyclopentadienes with at least one member selected from the group consisting of benzene and benzene derivatives represented by the formula, ##STR9## wherein R 2 , R 3 , R 4 , R 5 and R 6 have the same meanings as defined above, in the presence of a Friedel-Crafts catalyst and, if necessary, hydrolyzing the resulting ester.
Claim 18
Dependent Claim
205 words
A process for producing a composition represented by the formula, ##STR8## wherein R is hydrogen or an alkyl group having 1 to 3 carbon atoms, said four R groups being the same or different; R 1 is hydrogen, a mono- to tetra-hydric aliphatic alcohol moiety having 1 to 12 carbon atoms, an alkali or alkaline earth metal, ammonium group, or an organic amine residue; n is an integer of 1 to 4; and R 2 , R 3 , R 4 , R 5 and R 6 , which may be the same or different, are independently hydrogen or alkyl groups having 1 to 6 carbon atoms or R 2 and R 3 may form a ring when taken together, which comprises reacting a carboxylic ester of a dimer of at least one member selected from the group consisting of cyclopentadiene and mono- to di-alkyl (C 1-3 ) cyclopentadienes with at least one member selected from the group consisting of benzene and benzene derivatives represented by the formula, ##STR9## wherein R 2 , R 3 , R 4 , R 5 and R 6 have the same meanings as defined above, in the presence of a Friedel-Crafts catalyst and, if necessary, hydrolyzing the resulting ester.
Claim 19
Dependent Claim
125 words
A process for producing a composition represented by the formula, ##STR10## wherein n, R, R 1 , R 2 , R 3 , R 5 and R 6 have the same meanings as defined in claim 15, which comprises reacting a nitrile of a dimer of at least one member selected from the group consisting of cyclopentadiene and mono- to di-alkyl (C 1-3 )cyclopentadienes with at least one member selected from the group consisting of benzene and benzene derivatives represented by the formula, ##STR11## wherein R 2 , R 3 , R 4 , R 5 and R 6 have the same meanings as defined in claim 15, in the presence of a Friedel-Crafts catalyst, hydrolyzing the reaction product, and, if necessary, esterifying the hydrolyzate.
Claim 20
Dependent Claim
131 words
A process for producing a composition represented by the formula, ##STR12## wherein n, R, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 have the same meanings as defined in claim 15, which comprises reacting an aldehyde of a dimer of at least one member selected from the group consisting of cyclopentadiene and mono- to di-alkyl (C 1-3 )cyclopentadienes with at least one member selected from the group consisting of benzene and benzene derivatives represented by the formula, ##STR13## wherein R 2 , R 3 , R 4 , R 5 and R 6 have the same meanings as defined in claim 15, in the presence of a Friedel-Crafts catalyst, oxidizing the reaction product, and, if necessary, neutralizing or esterifying the oxidation product.
Claim 21
Dependent Claim
22 words
The process according to claim 15, wherein the Friedel-crafts catalyst is a boron tri-fluoride compound, hydrogen fluoride, aluminum chloride, or sulfuric acid.
Claim 22
Dependent Claim
23 words
The process according to claim 18 wherein the reaction is performed at 0° to 100° C for 1 to 20 hours with stirring.
Claim 23
Dependent Claim
28 words
The process according to claim 15, wherein the hydrolyzation is effected at a temperature of 80° to 200° C in the presence of an acid or a base.
Claim 24
Dependent Claim
27 words
The process according to claim 17, wherein the oxidization is effected with chromic acid, a permanganate or silver oxide at a temperature of 0° to 80° C.
Claim 25
Dependent Claim
26 words
The process according to claim 16, wherein the esterification is effected with a mono- to tetrahydric aliphatic alcohol at a temperature of 50° to 100° C.
Claim 26
Dependent Claim
22 words
The process according to claim 15, wherein the resulting ester is subjected to transesterification at a temperature of 50° to 100° C.
Claim 27
Dependent Claim
23 words
The process according to claim 15, wherein the carboxylic ester is reacted with benzene, toluene, ethylbenzene, cumene, butylbenzene, cymene, xylene, 1,2,4-trimethylbenzene, or tetrahydroanaphthalene.
Claim 28
Dependent Claim
22 words
The process according to claim 16, wherein the nitrile is reacted with benzene, toluene, ethylbenzene, cumene, butylbenzene, cymene, xylene, 1,2,4-trimethylbenzene or tetrahydronaphthalene.
Claim 29
Dependent Claim
22 words
The process according to claim 17, wherein the aldehyde is reacted with benzene, toluene, ethylbenzene, cumene, butylbenzene, cymene, xylene, 1,2,4-trimethylbenzene or tetrahydronaphthalene.
Claim 30
Dependent Claim
99 words
A synthetic emulsifier comprising as the essential active component a composition represented by the formula, ##STR14## wherein R is hydrogen or an alkyl group having 1 to 3 carbon atoms, said four R groups being the same or different; R 1 is an alkali metal, ammonium group, or an organic amine residue; and R 2 , R 3 , R 4 , R 5 and R 6 which may be the same or different, are independently hydrogen or alkyl groups having 1 to 6 carbon atoms, or R 2 and R 3 may form a ring when taken together.
Claim 31
Dependent Claim
99 words
A synthetic emulsifier comprising as the essential active component a composition represented by the formula, ##STR14## wherein R is hydrogen or an alkyl group having 1 to 3 carbon atoms, said four R groups being the same or different; R 1 is an alkali metal, ammonium group, or an organic amine residue; and R 2 , R 3 , R 4 , R 5 and R 6 which may be the same or different, are independently hydrogen or alkyl groups having 1 to 6 carbon atoms, or R 2 and R 3 may form a ring when taken together.
Claim 32
Dependent Claim
14 words
The emulsifier according to claim 27, wherein R 1 is potassium, sodium, or ammonium.
Claim 33
Dependent Claim
28 words
The emulsifier according to claim 27, wherein R 2 is hydrogen, methyl or ethyl, R 3 is hydrogen, or methyl and R 4 to R 6 are hydrogen.
Claim 34
Dependent Claim
12 words
The emulsifier according to claim 29, wherein all R groups are hydrogen.
Claim 35
Dependent Claim
97 words
A sizing agent comprising as the essential active component a composition represented by the formula, ##STR15## wherein R is hydrogen or an alkyl group having 1 to 3 carbon atoms, said four R groups being the same or different; R 1 is an alkali metal or an ammonium group; and R 2 , R 3 , R 4 , R 5 and R 6 , which may be the same or different, are independently hydrogen or alkyl groups having 1 to 6 carbon atoms, or R 2 and R 3 may form a ring when taken together.
Claim 36
Dependent Claim
97 words
A sizing agent comprising as the essential active component a composition represented by the formula, ##STR15## wherein R is hydrogen or an alkyl group having 1 to 3 carbon atoms, said four R groups being the same or different; R 1 is an alkali metal or an ammonium group; and R 2 , R 3 , R 4 , R 5 and R 6 , which may be the same or different, are independently hydrogen or alkyl groups having 1 to 6 carbon atoms, or R 2 and R 3 may form a ring when taken together.
Claim 37
Dependent Claim
41 words
The sizing agent according to claim 31, all R groups are hydrogen; R 2 is an alkyl group having 1 to 6 carbon atoms, R 3 and R 4 are hydrogen or methyl; and R 5 and R 6 are hydrogen.
Claim 38
Dependent Claim
14 words
The sizing agent according to claim 32, wherein R 1 is potassium or sodium.
Claim 39
Dependent Claim
128 words
An adhesive, tackifier, printing ink vehicle, or surface coating vehicle which comprises a composition represented by the formula, ##STR16## wherein R is hydrogen or an alkyl group having 1 to 3 carbon atoms, said four R groups being the same or different; R 1 is hydrogen, an alkali or alkaline earth metal, an ammonium group, a mono- to tetra-hydric aliphatic alcohol moiety having 1 to 12 carbon atoms, or an organic amine residue; n is an integer of 1 to 4; R 2 , R 3 , R 4 , R 5 and R 6 , which may be the same or different, are independently hydrogen or alkyl groups having 1 to 6 carbon atoms, or R 2 and R 3 may form a ring when taken together.
Claim 40
Dependent Claim
128 words
An adhesive, tackifier, printing ink vehicle, or surface coating vehicle which comprises a composition represented by the formula, ##STR16## wherein R is hydrogen or an alkyl group having 1 to 3 carbon atoms, said four R groups being the same or different; R 1 is hydrogen, an alkali or alkaline earth metal, an ammonium group, a mono- to tetra-hydric aliphatic alcohol moiety having 1 to 12 carbon atoms, or an organic amine residue; n is an integer of 1 to 4; R 2 , R 3 , R 4 , R 5 and R 6 , which may be the same or different, are independently hydrogen or alkyl groups having 1 to 6 carbon atoms, or R 2 and R 3 may form a ring when taken together.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-09-12 | 1981-03-14 | 1981-09-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-09-12 | 1985-03-14 | 1985-09-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-09-12 | 1989-03-14 | 1989-09-13 | $7700.00 | Window Closed / Lapsed |