US4900671A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Biocatalytic process for preparing phenolic resins using peroxidase or oxidase enzyme
Assignee: WestRock MWV LLC
•
Filing: 1987-07-08
•
Granted: 1990-02-13
•
Expires: 2007-07-08
Abstract
Abstract A process for the preparation of a phenolic resin which comprises reacting a phenol with a peroxidase or an oxidase enzyme and a peroxide in an organic solvent containing medium to generate phenolic radicals which react to form a phenolic resin.
Inventors
- 👤 Alexander R. Pokora
- 👤 William L. Cyrus, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 21:56
CPC Classifications
B; B41; B41M; B41M5/00; B41M5/124; B41M5/132; B41M5/155; C; C08; C08G; C08G61/00; C08G61/02; C08G61/10; Y; Y10; Y10T; Y10T428/00; Y10T428/23; Y10T428/234; Y10T428/31504; Y10T428/31942; Y10T428/31949; Y10T428/31964; Y10T428/31967
Claims Analysis
Total Claims: 43
Claim 1
Independent Claim
77 words
A process for preparing a phenolic dimer or trimer which comprises reacting a phenol at a concentration of at least 1 g/100 ml with a peroxidase or an oxidase enzyme and a peroxide or oxygen in a medium containing an organic solvent and water in a volumetric ratio of 1/10 to 10/1 to produce a dimer or a trimer of said phenol wherein said phenol is dissolved in said organic solvent, and recovering said dimer or trimer.
Claim 2
Dependent Claim
77 words
A process for preparing a phenolic dimer or trimer which comprises reacting a phenol at a concentration of at least 1 g/100 ml with a peroxidase or an oxidase enzyme and a peroxide or oxygen in a medium containing an organic solvent and water in a volumetric ratio of 1/10 to 10/1 to produce a dimer or a trimer of said phenol wherein said phenol is dissolved in said organic solvent, and recovering said dimer or trimer.
Claim 3
Dependent Claim
82 words
A process for preparing a phenolic resin which comprises reacting a phenol at a concentration of at least 1 g/100ml with a peroxidase enzyme in the presence of a peroxide or an oxidase enzyme in the presence of oxygen in a medium containing water and an organic solvent in a volumetric ratio of 1/10 to 10/1, to generate phenolic radicals which react to form a phenolic resin wherein said phenol is dissolved in said organic solvent containing medium, and recovering said resin.
Claim 4
Dependent Claim
82 words
A process for preparing a phenolic resin which comprises reacting a phenol at a concentration of at least 1 g/100ml with a peroxidase enzyme in the presence of a peroxide or an oxidase enzyme in the presence of oxygen in a medium containing water and an organic solvent in a volumetric ratio of 1/10 to 10/1, to generate phenolic radicals which react to form a phenolic resin wherein said phenol is dissolved in said organic solvent containing medium, and recovering said resin.
Claim 5
Dependent Claim
12 words
The process of claim 2 wherein said enzyme is a peroxidase enzyme.
Claim 6
Dependent Claim
18 words
The process of claim 2 wherein said phenolic resin has a molecular weight of approximately 1,000 to 30,000.
Claim 7
Dependent Claim
24 words
The process of claim 3 wherein said enzyme is reacted in an amount of about 10 milligrams to 5 grams per 100 grams phenol.
Claim 8
Dependent Claim
27 words
The process of claim 5 wherein said process further comprises forming a mixture of said phenol and said enzyme, and gradually adding said peroxide to said mixture.
Claim 9
Dependent Claim
27 words
The process of claim 6 wherein said peroxide is added to said mixture as a solution having a concentration of about 0.001 to 1.0 mols per liter.
Claim 10
Dependent Claim
18 words
The process of claim 3 wherein said reaction proceeds at a temperature of about 0° to 4020 C.
Claim 11
Dependent Claim
22 words
The process of claim 3 wherein said reaction is carried out at a pH in the range of about 4 to 12.
Claim 12
Dependent Claim
18 words
The process of claim 3 wherein said phenolic resin has a molecular weight of approximately 1000 to 15,000.
Claim 13
Dependent Claim
14 words
The process of claim 10 wherein said phenolic resin is useful as an adhesive.
Claim 14
Dependent Claim
18 words
The process of claim 3 wherein said phenolic resin has a molecular weight of approximately 500 to 5000.
Claim 15
Dependent Claim
16 words
The process of claim 12 wherein said phenolic resin is useful as a phenolic developer resin.
Claim 16
Dependent Claim
36 words
The process of claim 13 wherein said process further comprises reacting said developer resin with a salt of a metal selected from the group consisting of zinc, copper, cadmium, aluminum, indium, tin, chromium, cobalt and nickel.
Claim 17
Dependent Claim
10 words
The process of claim 14 wherein said metal is zinc.
Claim 18
Dependent Claim
98 words
The process of claim 3 wherein said phenol is represented by the formula I: ##STR4## where Y or Z may be the same or different and are selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an allyl group, a phenylalkyl group, a halogen atom, a --COOR group where R is a hydrogen atom or lower alkyl group, or a --NR 1 R 2 group where R 1 and R 2 are the same or different and represent a hydrogen atom, a lower alkyl group, or a phenylalkyl group.
Claim 19
Dependent Claim
47 words
The process of claim 3 wherein said organic solvent containing medium includes a first aqueous phase and a second water immiscible phase and said process includes the additional steps of recovering said phenolic resin from said water immiscible phase and recovering said enzyme from said aqueous phase.
Claim 20
Dependent Claim
27 words
The process of claim 3 wherein said organic solvent containing medium is an organic aqueous-medium having a water:organic volumetric ratio in the range of 1:2 to 2:1.
Claim 21
Dependent Claim
10 words
The process of claim 3 wherein said phenol is 4,4'-isopropylidenediphenol.
Claim 22
Dependent Claim
16 words
The process of claim 19 wherein said organic solvent containing medium includes methanol and ethyl acetate.
Claim 23
Dependent Claim
11 words
The process of claim 2 wherein said enzyme is horseradish peroxidase.
Claim 24
Dependent Claim
61 words
The process of claim 21 wherein said step of reacting said phenol includes forming a mixture of said phenol and said enzyme, and gradually adding said peroxide to said mixture and said mixture is prepared by dissolving said phenol in an organic solvent, dissolving said enzyme in water, and mixing the solution of said phenol with the solution of said enzyme.
Claim 25
Dependent Claim
24 words
The process of claim 1 wherein said enzyme is reacted in an amount of about 10 milligrams to 5 grams per 100 grams phenol.
Claim 26
Dependent Claim
21 words
The process of claim 1 wherein said phenol is reacted in a concentration of 1 to 100 g per 100 ml.
Claim 27
Dependent Claim
46 words
The process of claim 6 wherein said mixture of said phenol and said enzyme is formed by dissolving said phenol in an organic solvent to prepare a first solution, dissolving said enzyme in water to prepare a second solution, and mixing said first and second solutions.
Claim 28
Dependent Claim
23 words
The process of claim 25 wherein the concentration of said second solution is about 10 to 365 mg of said enzyme per liter.
Claim 29
Dependent Claim
11 words
The process of claim 3 wherein said enzyme is horseradish peroxidase.
Claim 30
Dependent Claim
28 words
The process of claim 25 wherein said peroxide is added to said mixture in an amount of about 0.1 to 2.5 mole per 100 grams of said phenol.
Claim 31
Dependent Claim
11 words
The process of claim 28 wherein said peroxide is hydrogen peroxide.
Claim 32
Dependent Claim
40 words
The process of claim 1 wherein said phenol is selected from the group consisting of phenol, 4-t-butylphenol, 4-n-butylphenol, 4-ethylphenol, cresol, p-phenylphenol p-octylphenol, p-nonylphenol, p-hydroxybenzoic acid, 4-hydroxynaphthoic acid, p,p'-biphenol, 4-aminosalicylic acid, salicylic acid, methyl salicylate, ethyl salicylate, 4-4'-isopropylidenediphenol, and ethyl 4-hydroxybenzoate.
Claim 33
Dependent Claim
38 words
The process of claim 2 wherein said phenol is selected from the group consisting of phenol, 4-t-butylphenol, 4-n-butylphenol, 4-ethylphenol, cresol, p-phenylphenol, p-octylphenol, p-nonylphenol, p-hydroxybenzoic acid, 4-hydroxynaphthoic acid, p,p'-biphenol, 4-aminosalicylic acid, salicylic acid, methosalicylate, ethylsalicylate, 4-4'-isopropylidenediphenol, and ethyl 4-hydroxybenzoate.
Claim 34
Dependent Claim
24 words
The process of claim 1 wherein said organic solvent is selected from the group consisting of ethanol, methanol, dioxane, tetrahydrofuran, dimethyl formamide and acetone.
Claim 35
Dependent Claim
24 words
The process of claim 2 wherein said organic solvent is selected from the group consisting of ethanol, methanol, dioxane, tetrahydrofuran, dimethyl formamide and acetone.
Claim 36
Dependent Claim
25 words
The process of claim 1 wherein said organic solvent is selected from the group consisting of hexane, trichloromethane, methyl ethyl ketone, ethyl acetate and butanol.
Claim 37
Dependent Claim
25 words
The process of claim 2 wherein said organic solvent is selected from the group consisting of hexane, trichloromethane, methyl ethyl ketone, ethyl acetate and butanol.
Claim 38
Dependent Claim
13 words
The process of claim 1, wherein said organic solvent is miscible with water.
Claim 39
Dependent Claim
13 words
The process of claim 1, wherein said organic solvent is immiscible with water.
Claim 40
Dependent Claim
13 words
The process of claim 2, wherein said organic solvent is miscible with water.
Claim 41
Dependent Claim
13 words
The process of claim 2, wherein said organic solvent is immiscible with water.
Claim 42
Dependent Claim
12 words
The process of claim 1, wherein said enzyme is a peroxidase enzyme.
Claim 43
Dependent Claim
11 words
The process of claim 40, wherein said enzyme is horseradish peroxidase.
References Cited (Backward Citations)
US3244550A
Cited
US3244549A
Cited
US4025490A
Cited
US4173684A
Cited
US4165103A
Cited
US4165102A
Cited
DE3430735A1
Cited
US4647952A
Cited
US4765901A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-02-12 | 1993-08-14 | 1994-02-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-02-12 | 1997-08-14 | 1998-02-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-02-12 | 2001-08-14 | 2002-02-13 | $7700.00 | Window Closed / Lapsed |