Patent US4214909A successfully refreshed from Google Patents.
US4214909A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Aquatic antifouling method
Assignee: Kuraray Co Ltd
•
Filing: 1977-12-15
•
Granted: 1980-07-29
•
Expires: 1997-12-15
Abstract
Abstract Method for controlling fouling to structures caused by aquatic fouling organisms such as barnacles, slime, sea moss, algae, etc. which comprises applying to said structures sesquiterpene alcohols such as farnesol, nerolidol, and dehydronerolidol, and the organic carboxylic acid esters thereof.
Inventors
- 👤 Shizuo Mawatari
- 👤 Takashi Nishida
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 04:44
CPC Classifications
A; A01; A01N; A01N49/00; C; C02; C02F; C02F1/00; C02F1/50; C09; C09D; C09D5/00; C09D5/16; C09D5/1606; C09D5/1612; C09D5/1625
Claims Analysis
Total Claims: 40
Claim 1
Independent Claim
169 words
A method for rendering structures exposed to an aqueous environment resistant to fouling by barnacles, algae, bryozoa, slime, hydrozoa, mussels, oysters, and ascidiacea organisms in said environment, comprising contacting said structures with an effective antifouling amount of a sesquiterpene compound of the general formula (I): ##STR8## wherein X 1 , X 2 and X 3 each is a hydrogen atom, or one of X 1 and X 3 is a hydrogen atom with the other and X 2 representing a double bond in the carbon chain of the compound; X 4 , X 5 and X 6 each is a hydrogen atom, or one of X 4 and X 6 is a hydrogen atom with the other and X 5 representing a double bond in the carbon chain of the compound; and Y is a group selected from the group consisting of: ##STR9## wherein Z is a hydrogen atom or ##STR10## where R is a hydrogen atom or a hydrocarbon group which may optionally be substituted; or mixtures thereof.
Claim 2
Independent Claim
169 words
A method for rendering structures exposed to an aqueous environment resistant to fouling by barnacles, algae, bryozoa, slime, hydrozoa, mussels, oysters, and ascidiacea organisms in said environment, comprising contacting said structures with an effective antifouling amount of a sesquiterpene compound of the general formula (I): ##STR8## wherein X 1 , X 2 and X 3 each is a hydrogen atom, or one of X 1 and X 3 is a hydrogen atom with the other and X 2 representing a double bond in the carbon chain of the compound; X 4 , X 5 and X 6 each is a hydrogen atom, or one of X 4 and X 6 is a hydrogen atom with the other and X 5 representing a double bond in the carbon chain of the compound; and Y is a group selected from the group consisting of: ##STR9## wherein Z is a hydrogen atom or ##STR10## where R is a hydrogen atom or a hydrocarbon group which may optionally be substituted; or mixtures thereof.
Claim 3
Dependent Claim
30 words
The method of claim 1, wherein said structures are rendered resistant to fouling by adding an effective antifouling amount of said sesquiterpene compound of formula (I) to said aqueous environment.
Claim 4
Dependent Claim
40 words
The method of claim 2, wherein said sesquiterpene compound of formula (I) is added to said aqueous environment at a rate of about 0.001 to about 50 ppm for a period of about 1 to about 3 hours each day.
Claim 5
Dependent Claim
39 words
The method of claim 2, wherein said sesquiterpene compound of formula (I) is added to said aqueous environment at a rate of about 0.05 to 50 ppm for a period of about 1 to about 3 hours each day.
Claim 6
Dependent Claim
23 words
The method of claim 2, wherein said sesquiterpene compound of formula (I) is prepared as an emulsion and added to said aqueous environment.
Claim 7
Dependent Claim
25 words
The method of claim 1, wherein said sesquiterpene compound is formulated into an antifoulant coating with a suitable film-forming carrier and applied to said structure.
Claim 8
Dependent Claim
28 words
The method of claim 6, wherein said film-forming carrier is selected from the group consisting of oily varnishes, synthetic rubbers, natural resins, and admixtures thereof with a pigment.
Claim 9
Dependent Claim
24 words
The method of claim 6, wherein said sesquiterpene compound of formula (I) comprises about 5 to about 60% by weight of said antifoulant coating.
Claim 10
Dependent Claim
17 words
The method of claim 1, wherein said sesquiterpene compound of formula (I) is compounded into said structures.
Claim 11
Dependent Claim
30 words
The method of claim 9, wherein said sesquiterpene compound is formulated with a compatible carrier selected from the group consisting of synthetic resins and solvents and compounded into said structures.
Claim 12
Dependent Claim
57 words
The method of claim 1, wherein R in the sesquiterpene compound of formula (I) is a hydrocarbon group selected from the group consisting of alkyl groups of 1 to 8 carbon atoms, alkenyl groups of 2 to 8 carbon atoms, aralkyl groups of 7 to 11 carbon atoms, and aryl groups of 6 to 10 carbon atoms.
Claim 13
Dependent Claim
30 words
The method of claim 11, wherein R is a hydrocarbon group substituted with a group selected from the group consisting of halogen, alkyl, hydroxy, alkoxy, nitro, dioxy, and amino groups.
Claim 14
Dependent Claim
38 words
The method of claim 12, wherein R is a hydrocarbon group selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, ethenyl, propenyl, butenyl, benzyl, piperonyl, methylbenzyl, phenyl, hydroxyphenyl, 3,4-methylenedioxyphenyl, chlorophenyl, dichlorophenyl, methylphenyl, methylaminophenyl, methoxyphenyl and nitrophenyl.
Claim 15
Dependent Claim
21 words
The method of claim 1, wherein Y is the sesquiterpene compound of formula (I) is a group of the formula: ##STR11##
Claim 16
Dependent Claim
11 words
The method of claim 14, wherein Z is a hydrogen atom.
Claim 17
Dependent Claim
18 words
The method of claim 14, wherein said sesquiterpene compound is a compound of the general formula (2): ##STR12##
Claim 18
Dependent Claim
14 words
The method of claim 16, wherein said sesquiterpene compound of formula (II) is farnesol.
Claim 19
Dependent Claim
17 words
The method of claim 16, wherein Z in the sesquiterpene compound of general formula (II) is ##STR13##
Claim 20
Dependent Claim
53 words
The method of claim 18, wherein R is selected from the group consisting of alkyl groups of 1 to 8 carbon atoms, alkenyl groups of 2 to 8 carbon atoms, substituted and unsubstituted aralkyl groups of 7 to 11 carbon atoms, and substituted and unsubstituted aryl groups of 6 to 10 carbon atoms.
Claim 21
Dependent Claim
37 words
The method of claim 19, wherein R is selected from the group consisting of lower alkyl groups, lower alkenyl groups, a phenyl group, or a phenyl group substituted by lower alkyl, lower alkoxy, chlorine or dioxy groups.
Claim 22
Dependent Claim
32 words
The method of claim 20, wherein said sesquiterpene compound is selected from the group consisting of farnesyl 3,4-methylenedioxybenzoate, farnesyl acetate, farnesyl trimethylacetate, farnesyl β,β-dimethyl acrylate, farnesyl benzoate, farnesyl 4-methoxybenzoate, and farnesyl 3,4-dichlorobenzoate.
Claim 23
Dependent Claim
22 words
The method of claim 1, wherein Y in the sesquiterpene compound of general formula (I) is a group of the formula: ##STR14##
Claim 24
Dependent Claim
11 words
The method of claim 22, wherein Z is a hydrogen atom.
Claim 25
Dependent Claim
18 words
The method of claim 22, wherein said sesquiterpene compound is a compound of the general formula (III): ##STR15##
Claim 26
Dependent Claim
15 words
The method of claim 24, wherein said sesquiterpene compound of general formula (III) is nerolidol.
Claim 27
Dependent Claim
15 words
The method of claim 24, wherein Z in the compound of formula (III) is ##STR16##
Claim 28
Dependent Claim
53 words
The method of claim 26, wherein R is selected from the group consisting of alkyl groups of 1 to 8 carbon atoms, alkenyl groups of 2 to 8 carbon atoms, substituted and unsubstituted aralkyl groups of 7 to 11 carbon atoms, and substituted and unsubstituted aryl groups of 6 to 10 carbon atoms.
Claim 29
Dependent Claim
37 words
The method of claim 27, wherein R is selected from the group consisting of lower alkyl groups, lower alkenyl groups, a phenyl group, or a phenyl group substituted by lower alkyl, lower alkoxy, chlorine or dioxy groups.
Claim 30
Dependent Claim
12 words
The method of claim 28, wherein said sesquiterpene compound is nerolidyl acetate.
Claim 31
Dependent Claim
14 words
The method of claim 1, wherein Y in the general formula (I) is ##STR17##
Claim 32
Dependent Claim
11 words
The method of claim 30, wherein Z is a hydrogen atom.
Claim 33
Dependent Claim
18 words
The method of claim 30, wherein said sesquiterpene compound is a compound of the general formula (IV): ##STR18##
Claim 34
Dependent Claim
14 words
The method of claim 32, wherein said sesquiterpene compound of formula (IV) is dehydronerolidol.
Claim 35
Dependent Claim
16 words
The method of claim 32, wherein Z in the sesquiterpene compound of formula IV is ##STR19##
Claim 36
Dependent Claim
53 words
The method of claim 34, wherein R is selected from the group consisting of alkyl groups of 1 to 8 carbon atoms, alkenyl groups of 2 to 8 carbon atoms, substituted and unsubstituted aralkyl groups of 7 to 11 carbon atoms, and substituted and unsubstituted aryl groups of 6 to 10 carbon atoms.
Claim 37
Dependent Claim
37 words
The method of claim 35, wherein R is selected from the group consisting of lower alkyl groups, lower alkenyl groups, a phenyl group, or a phenyl group substituted by lower alkyl, lower alkoxy, chlorine or dioxy groups.
Claim 38
Dependent Claim
12 words
The method of claim 36, wherein said sesquiterpene compound is dehydronerolidyl acetate.
Claim 39
Dependent Claim
13 words
The method of claim 1, wherein the sesquiterpene compound (I) is an ester.
Claim 40
Dependent Claim
59 words
The method of claim 1, wherein R is the residue of an acid selected from the group consisting of formic acid, acetic acid, propionic acid, butyric acid, valeric acid, pivalic acid, acrylic acid, methacrylic acid, crotonic acid, senecioic acid (β,β-dimethylacrylic acid),benzoic acid, p-hydroxybenzoic acid, p-chlorobenzoic acid, 3,4-dichlorobenzoic acid, p-methylbenzoic acid, o-methylaminobenzoic acid, p-methoxybenzoic acid, piperonylic acid and p-nitrobenzoic acid.
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) | 1983-07-29 | 1984-01-28 | 1984-07-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-07-29 | 1988-01-28 | 1988-07-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-07-29 | 1992-01-28 | 1992-07-29 | $7700.00 | Window Closed / Lapsed |