US3937674A
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US
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Preparation of modified petroleum resins
Assignee: Stamicarbon BV
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Filing: 1972-09-19
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Granted: 1976-02-10
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Expires: 1992-09-19
Abstract
Abstract Petroleum resin comprising units of cyclopentadiene, methyl cyclopentadiene or both is reacted at 150°-320°C with an unsaturated fatty acid, such as tall oil fatty acid, in the presence of magnesium oxide or other metal compound for a period of time until a modified resin having a melting point of at least 125°C, preferably 140°-160°C is obtained. The resulting resins are especially useful as binding and thickening agents for printing ink resulting in an ink that dries rapidly and is resistant to rubbing.
Inventors
- 👤 Jan Laarkamp
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 08:08
CPC Classifications
C; C09; C09D; C09D11/00; C09D11/02; C09D11/10; C09D11/106; C09D11/108; C08; C08C; C08C19/00; C08C19/28
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
200 words
In a process for the preparation of a modified petroleum resin comprising mixing and reacting together, at a temperature of about 150° C. to about 320° C: a. a weakly unsaturated petroleum resin, and b. from about 5 to about 50% by weight, calculated on the amount of resin component (a), at least one unsaturated fatty acid having from 12-30 carbon atoms, the improvement comprising using a weakly unsaturated petroleum resin composed essentially of polymerized units of cyclopentadiene, methyl cyclopentadiene or both and obtained by thermal polymerization of essentailly cyclopentadiene, methylcyclopentadiene or dimers thereof, having a melting point between 70° C. and 200° C. and a bromine number, expressed as grams of bromine per 100 grams of resin, of less than 150, and conducting the reacting in the presence of from about 0.05 to about 5% by weight, calculated on the amount of resin component (a), of metal compound soluble in the reaction mixture and substantially free from forming strongly colored products in combination with components (a) and (b), the metal selected from the group consisting of magnesium, aluminum and zinc, and continuing the reaction until a resin product having a melting point of at least 125° C. is obtained.
Claim 2
Dependent Claim
200 words
In a process for the preparation of a modified petroleum resin comprising mixing and reacting together, at a temperature of about 150° C. to about 320° C: a. a weakly unsaturated petroleum resin, and b. from about 5 to about 50% by weight, calculated on the amount of resin component (a), at least one unsaturated fatty acid having from 12-30 carbon atoms, the improvement comprising using a weakly unsaturated petroleum resin composed essentially of polymerized units of cyclopentadiene, methyl cyclopentadiene or both and obtained by thermal polymerization of essentailly cyclopentadiene, methylcyclopentadiene or dimers thereof, having a melting point between 70° C. and 200° C. and a bromine number, expressed as grams of bromine per 100 grams of resin, of less than 150, and conducting the reacting in the presence of from about 0.05 to about 5% by weight, calculated on the amount of resin component (a), of metal compound soluble in the reaction mixture and substantially free from forming strongly colored products in combination with components (a) and (b), the metal selected from the group consisting of magnesium, aluminum and zinc, and continuing the reaction until a resin product having a melting point of at least 125° C. is obtained.
Claim 3
Dependent Claim
19 words
The process according to claim 1 wherein the petroleum resin (a) has a melting point between 140°C and 180°C.
Claim 4
Dependent Claim
18 words
The process according to claim 1 wherein the petroleum resin of (a) has a bromine number of 30-75.
Claim 5
Dependent Claim
22 words
The process according to claim 1 wherein the process is conducted at a temperature of about 240° C to about 275° C.
Claim 6
Dependent Claim
19 words
The process according to claim 1 wherein the amount of fatty acid component (b) is 10-30 % by weight.
Claim 7
Dependent Claim
16 words
The process according to claim 1 wherein the fatty acid component (b) is tall-oil fatty acid.
Claim 8
Dependent Claim
40 words
The process according to claim 1 wherein the fatty acid component (b) is selected from the group consisting of oleic acid, linolenic acid, linoleic acid, palmitoleic acid, elaidic acid, ricinoleic acid, petroselic acid, arachidonic acid, cetoleic acid and mixtures thereof.
Claim 9
Dependent Claim
21 words
The process according to claim 1 wherein the amount of the metal compound is from 0.1 to 1.0 % by weight.
Claim 10
Dependent Claim
11 words
The process according to claim 1 wherein the metal is magnesium.
Claim 11
Dependent Claim
32 words
The process according to claim 1 wherein the metal compound is selected from the group consisting of zinc oxide, zinc oleate, aluminum oleate, aluminum oxide, magnesium oxide, magnesium stearate and magnesium oleate.
Claim 12
Dependent Claim
16 words
The process according to claim 1 wherein the reaction is conducted in the absence of oxygen.
Claim 13
Dependent Claim
23 words
The process according to claim 1 wherein the reaction is continued until a resin product having a melting point of 140°-160°C is obtained.
Claim 14
Dependent Claim
39 words
A process according to claim 1 in which the reaction is carried out in the presence of an olefinically unsaturated aromatic hydrocarbon in a proportion of from 1 to 6 % by weight based on the said petroleum resin.
Claim 15
Dependent Claim
60 words
A process according to claim 1 in which the reaction is carried out in the presence of a mixture of acrylic acid or methacrylic acid and an alkylester of acrylic acid or of methacrylic acid or of a copolymer derived from such monomers, in a proportion of from 1 to 10 % by weight based on the said petroleum resin.
Claim 16
Dependent Claim
45 words
The process according to claim 1 wherein there is further included in the reaction mixture from 5-100 % by weight, calculated on the amount of resin component (a), a phenol-formaldehyde resin having an aldehyde to phenol ratio between 1 : 1 and 2 : 1.
Claim 17
Dependent Claim
18 words
The process according to claim 15 wherein the phenol-formaldehyde resin is formed in situ under the reaction conditions.
Claim 18
Dependent Claim
19 words
The process according to claim 15 wherein the amount of said phenol-formaldehyde resin is from 15-45 % by weight.
Claim 19
Dependent Claim
20 words
The process according to claim 15 wherein the process is conducted at a temperature of about 225°C to about 275°C.
Claim 20
Dependent Claim
38 words
The process according to claim 1 wherein there is further included in the reaction mixture from 1-25 % by weight, calculated on the amount of resin component (a) a substituted or unsubstituted phenol having from 7-16 carbon atoms.
Claim 21
Dependent Claim
18 words
The process according to claim 19 wherein the amount of said phenol is from 4-10 % by weight.
Claim 22
Dependent Claim
20 words
The process according to claim 19 wherein the process is conducted at a temperature of about 225°C to about 275°C.
Claim 23
Dependent Claim
51 words
The process according to claim 1 wherein there is further included in the reaction mixture from 0.5 to 20 % by weight, calculated on the amount of resin component (a), at least one resin acid selected from the group consisting of abietic acid, neo abietic acid laevopimaric acid and mixtures thereof.
Claim 24
Dependent Claim
18 words
The process according to claim 22 wherein the amount of resin acid is from 1.5-5 % by weight.
Claim 25
Dependent Claim
20 words
The process according to claim 22 wherein the process is conducted at a temperature of about 240°C to about 275°C.
Claim 26
Dependent Claim
196 words
In a process for the preparation of a modified petroleum resin comprising mixing and reacting together, at a temperature of about 260°C to about 275°C: a. a weakly unsaturated petroleum resin, and b. from about 5 to about 50% by weight, calculated on the amount of resin component (a), at least one unsaturated fatty acid having from 12-30 carbon atoms; the improvement comprising using a weakly unsaturated petroleum resin composed essentially of polymeric units of cyclopentadiene, methyl cyclopentadiene or both and obtained by thermal polymerization of essentially cyclopentadiene, methyl cyclopentadiene or dimers thereof, having a melting point between 70°C and 120°C and a bromine number, expressed as grams of bromine per 100 grams of resin, of less than 120, and conducting the reaction in the presence of from about 0.05 to about 5% by weight, calculated on the amount of resin component (a), of metal compound soluble in the reaction mixture and substantially free from forming strongly colored products in combination with components (a) and (b), the metal selected from the group consisting of magnesium, aluminum and zinc, and continuing the reaction until a resin product having a melting point of at least 125°C. is obtained.
Claim 27
Dependent Claim
196 words
In a process for the preparation of a modified petroleum resin comprising mixing and reacting together, at a temperature of about 260°C to about 275°C: a. a weakly unsaturated petroleum resin, and b. from about 5 to about 50% by weight, calculated on the amount of resin component (a), at least one unsaturated fatty acid having from 12-30 carbon atoms; the improvement comprising using a weakly unsaturated petroleum resin composed essentially of polymeric units of cyclopentadiene, methyl cyclopentadiene or both and obtained by thermal polymerization of essentially cyclopentadiene, methyl cyclopentadiene or dimers thereof, having a melting point between 70°C and 120°C and a bromine number, expressed as grams of bromine per 100 grams of resin, of less than 120, and conducting the reaction in the presence of from about 0.05 to about 5% by weight, calculated on the amount of resin component (a), of metal compound soluble in the reaction mixture and substantially free from forming strongly colored products in combination with components (a) and (b), the metal selected from the group consisting of magnesium, aluminum and zinc, and continuing the reaction until a resin product having a melting point of at least 125°C. is obtained.
Claim 28
Dependent Claim
223 words
In a process for the preparation of a modified petroleum resin comprising heating at a temperature of about 240°C to about 290°C: a. a weakly unsaturated petroleum resin with b. from about 5 to about 50% by weight, calculated on the amount of resin component (a), at least one unsaturated fatty acid having from 12-30 carbon atoms; the improvement comprising using a weakly unsaturated petroleum resin composed essentially of polymeric units of cyclopentadiene, methyl cyclopentadiene or both and obtained by thermal polymerization of essentially cyclopentadiene, methyl cyclopentadiene or dimers thereof, having a low melting point and a bromine number, expressed as grams of bromine per 100 grams of resin, of less than 120 and heating the resin until a resin product having a higher melting point of 140°-180°C is produced, and thereafter mixing and reacting resin component (a) at a temperature of about 240°C to about 260° and conducting the reaction in the presence of from about 0.05 to about 5% by weight, calculated on the amount of resin component (a), of metal compound soluble in the reaction mixture and substantially free from forming strongly colored products in combination with components (a) and (b), the metal selected from the group consisting of magnesium, aluminum and zinc, and continuing the reaction until a resin product having a melting point of from 140°-160°C is obtained.
Claim 29
Dependent Claim
223 words
In a process for the preparation of a modified petroleum resin comprising heating at a temperature of about 240°C to about 290°C: a. a weakly unsaturated petroleum resin with b. from about 5 to about 50% by weight, calculated on the amount of resin component (a), at least one unsaturated fatty acid having from 12-30 carbon atoms; the improvement comprising using a weakly unsaturated petroleum resin composed essentially of polymeric units of cyclopentadiene, methyl cyclopentadiene or both and obtained by thermal polymerization of essentially cyclopentadiene, methyl cyclopentadiene or dimers thereof, having a low melting point and a bromine number, expressed as grams of bromine per 100 grams of resin, of less than 120 and heating the resin until a resin product having a higher melting point of 140°-180°C is produced, and thereafter mixing and reacting resin component (a) at a temperature of about 240°C to about 260° and conducting the reaction in the presence of from about 0.05 to about 5% by weight, calculated on the amount of resin component (a), of metal compound soluble in the reaction mixture and substantially free from forming strongly colored products in combination with components (a) and (b), the metal selected from the group consisting of magnesium, aluminum and zinc, and continuing the reaction until a resin product having a melting point of from 140°-160°C is obtained.
Claim 30
Dependent Claim
22 words
A modified resin consisting substantially of units derived from cyclopentadiene, methyl cyclopentadiene or their mixture produced by the process of claim 1.
Claim 31
Dependent Claim
23 words
The process according to claim 1 wherein the metal compound is an oxide of said metal or a carboxylic salt of said metal.
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) | 1979-02-09 | 1979-08-11 | 1980-02-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-02-09 | 1983-08-11 | 1984-02-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-02-09 | 1987-08-11 | 1988-02-10 | $7700.00 | Window Closed / Lapsed |