US4576838A
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Anti-fouling coating composition, process for applying same and coating thereby obtained
Assignee: PHILADELPHIA RESINS Corp A CORP OF DE
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Filing: 1984-08-15
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Granted: 1986-03-18
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Expires: 2004-08-15
Abstract
Abstract The anti-fouling compositions and process described herein are capable of preventing or delaying for prolonged periods the fouling of structures such as boats, ships, piers, etc., having substantial portions thereof submerged in water. Processes are described herein for preparing and applying these compositions as coatings to objects to be submerged in sea water. These compositions comprise a number of components, some of which may be reacted, including: (a) an organotin polymer or copolymer of the monomer having the formula R 3 SnOOCR', wherein R and R' are defined hereinafter; (b) a hydrophilic component having poor water solubility, preferably being water insoluble and having at least two hydroxy groups per molecule, such as caster oil, partially hydrolyzed polyvinyl acetate, partially hydrolyzed copolymers of vinyl chloride and vinyl acetate, polymers of monovinyl ether of alkylene glycols such as ethylene glycol, etc.; (c) a hydrophobic component comprising a compound having 1-3 urethane groups therein and no more than about 20 carbon atoms preferably made by the reaction of an isocyanate compound, such as diisocyanate, with one or more hydroxy-containing solvents, such as ethanol, propanol, ethylene glycol monoethyl ether, etc., or a monoisocyanate with a di- or tri-hydroxy compound such as ethylene glycol, propylene glycol, glycerine, etc., preferably in the presence of low molecular weight ketones, esters and aromatic hydrocarbons, such as methyl ethyl ketone, cyclohexanone, toluene, etc.
Inventors
- 👤 Murray Rosen
- 👤 Thomas Lane
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 15:54
CPC Classifications
C; C09; C09D; C09D5/00; C09D5/16; C09D5/1606; C09D5/1637; C09D5/1643; Y; Y10; Y10S; Y10S428/00; Y10S428/907
Claims Analysis
Total Claims: 33
Claim 1
Independent Claim
242 words
An anti-fouling, film forming composition comprising: (a) a hydrophilic component selected from the group consisting of castor oil, partially dehydrated castor oil having a hydroxyl equivalent weight of 600-800, a partially hydrolyzed polyvinylester having a hydroxyl equivalent weight of 300-600, a partially hydrolyzed copolymer of vinyl chloride and vinyl ester having a hydroxyl equivalent weight of 300-600; and a polymer of a monovinyl or monoalphamethylvinyl or monoalphaethylvinyl ether of an alkylene glycol having 2-6 carbon atoms, said polymer having a hydroxyl equivalent weight of 300-600; (b) a hydrophobic component having no more than 35 carbon atoms therein and having 1-3 urethane groups per molecule; (c) a solvent component having one or more compounds selected from the group consisting of a hydroxyl-containing compound having the formula R"(OH) n' wherein R" represents an aliphatic, arylaliphatic or cycloaliphatic hydrocarbon group having 2-10 carbon atoms and n' is an integer having a value of 1-3, R" may also have 1 carbon atom when n' is 1, a monoether or monoester of an alkylene glycol having no more than 10 carbon atoms, an aromatic hydrocarbon having a kauri butanol value of 73-105, and a ketone having no more than 10 carbon atoms; and (d) an organic tin polymer of a monomer having the formula R 3 SnOOCR' wherein R is a lower alkyl, cycloalkyl or aryl radical and R' is a polymerizable radical selected from the group consisting of vinyl, lower-alkylvinyl, vinyl aryl and lower-alkylvinyl aryl groups:
Claim 2
Dependent Claim
242 words
An anti-fouling, film forming composition comprising: (a) a hydrophilic component selected from the group consisting of castor oil, partially dehydrated castor oil having a hydroxyl equivalent weight of 600-800, a partially hydrolyzed polyvinylester having a hydroxyl equivalent weight of 300-600, a partially hydrolyzed copolymer of vinyl chloride and vinyl ester having a hydroxyl equivalent weight of 300-600; and a polymer of a monovinyl or monoalphamethylvinyl or monoalphaethylvinyl ether of an alkylene glycol having 2-6 carbon atoms, said polymer having a hydroxyl equivalent weight of 300-600; (b) a hydrophobic component having no more than 35 carbon atoms therein and having 1-3 urethane groups per molecule; (c) a solvent component having one or more compounds selected from the group consisting of a hydroxyl-containing compound having the formula R"(OH) n' wherein R" represents an aliphatic, arylaliphatic or cycloaliphatic hydrocarbon group having 2-10 carbon atoms and n' is an integer having a value of 1-3, R" may also have 1 carbon atom when n' is 1, a monoether or monoester of an alkylene glycol having no more than 10 carbon atoms, an aromatic hydrocarbon having a kauri butanol value of 73-105, and a ketone having no more than 10 carbon atoms; and (d) an organic tin polymer of a monomer having the formula R 3 SnOOCR' wherein R is a lower alkyl, cycloalkyl or aryl radical and R' is a polymerizable radical selected from the group consisting of vinyl, lower-alkylvinyl, vinyl aryl and lower-alkylvinyl aryl groups:
Claim 3
Dependent Claim
13 words
The composition of claim 1, in which said hydrophilic component is castor oil.
Claim 4
Dependent Claim
23 words
The composition of claim 1, in which said hydrophilic component is a partially dehydrated castor oil having a hydroxyl equivalent weight of 600-800.
Claim 5
Dependent Claim
22 words
The composition of claim 1, in which said hydrophilic component is a partially hydrolyzed polyvinylester having a hydroxyl equivalent weight of 300-600.
Claim 6
Dependent Claim
15 words
The composition of claim 4, in which said partially hydrolyzed polyvinylester is partially hydrolyzed polyvinylacetate.
Claim 7
Dependent Claim
29 words
The composition of claim 1, in which said hydrophilic component is a partially hydrolyzed copolymer of vinyl chloride and a vinyl ester having a hydroxyl equivalent weight of 300-600.
Claim 8
Dependent Claim
13 words
The composition of claim 6, in which said vinyl ester is vinyl acetate.
Claim 9
Dependent Claim
19 words
The composition of claim 1, in which said hydrophobic component has an average of 2 urethane groups per molecule.
Claim 10
Dependent Claim
35 words
The composition of claim 8, in which said hydrophobic component is the reaction product of a diisocyanate and a monohydric compound selected from the group consisting of monohydric alcohols and a monoalkylether of a glycol.
Claim 11
Dependent Claim
51 words
The composition of claim 9, in which said reaction product is a diisocyanate selected from the group consisting of hexamethylene diisocyanate, tolylene diisocyanate and phenylene diisocyanate and said monohydric compound is selected from the class consisting of ethanol, propanol, butanol, and the monoethyl and monopropyl ethers of ethylene and propylene glycols.
Claim 12
Dependent Claim
25 words
The composition of claim 10, in which said monohydric compound is selected from the group consisting of ethanol and the monoethyl ether of ethylene glycol.
Claim 13
Dependent Claim
33 words
The composition of claim 1, in which said organic tin polymer is derived from a monomer selected from the group consisting of tri-n-butylin p-vinylbenzoate, tri-n-butyltin methacrylate, tri-n-propyltin methacrylate, tri-phenyltin methacrylate and tri-n-propyltin p-vinylbenzoate.
Claim 14
Dependent Claim
42 words
The composition of claim 1, in which on the basis of solids content there is 19-38 percent by weight of the hydrophilic component, 6-12 percent by weight of the hydrophobic component, and 50-75 percent by weight of the said organic tin polymer.
Claim 15
Dependent Claim
35 words
The composition of claim 13, in which there is 18-30 percent by weight of the hydrophilic component, 6-8 percent by weight of the hydrophobic component and 65-75 percent by weight of the said tin polymer.
Claim 16
Dependent Claim
35 words
The composition of claim 13, in which said hydrophobic component is the reaction product of a diisocyanate and a monohydric compound selected from the group consisting of monohydric alcohols and a monoalkylether of a glycol.
Claim 17
Dependent Claim
58 words
The composition of claim 15, in which said reaction product is from a diisocyanate selected from the group consisting of hexamethylene diisocyanate, tolylene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, decylene diisocyanate and phenylene diisocyanate and said monohydric compound is selected from the class consisting of ethanol, propanol, butanol, and the monoethyl and monopropyl ethers of ethylene and propylene glycols.
Claim 18
Dependent Claim
25 words
The composition of claim 16, in which said monohydric compound is selected from the group consisting of ethanol and the monoethyl ether of ethylene glycol.
Claim 19
Dependent Claim
33 words
The composition of claim 17, in which said organic tin polymer is derived from a monomer selected from the group consisting of tri-n-butylin p-vinylbenzoate, tri-n-butyltin methacrylate, tri-n-propyltin methacrylate, tri-phenyltin methacrylate and tri-n-propyltin p-vinylbenzoate.
Claim 20
Dependent Claim
24 words
The component of claims 1, 2, 8, 9, 13 or 18 in which said hydrophobic composition has no more than 20 carbon atoms therein.
Claim 21
Dependent Claim
74 words
The composition of claim 1, in which said hydrophilic component comprises 10.45-16.72 percent by weight of castor oil; said hydrophobic component comprises 3.7-6 percent by weight of the reaction product of toluene diisocyanate and ethyl alcohol; 39.6-49.5 percent by weight of poly(triethyltin)methacrylate and the balance making up 100 percent by weight comprises one or more solvents selected from the group consisting of ethyl alcohol, methylethyl ketone, n-butylmonoether of ethylene glycol, toluene and ethyl acetate.
Claim 22
Dependent Claim
170 words
An anti-fouling coating deposited on a surface of an object to be submerged in sea water comprising 50-75 percent by weight based on said coating of an organic tin polymer of a monomer having the formula R 3 SnOOCR' wherein R is a lower alkyl, cycloalkyl or aryl radical and R' is a polymerizable radical selected from the group consisting of vinyl, lower alkylvinyl, vinylaryl and lower alkylvinylaryl groups; 19-38 percent by weight of a hydrophilic component selected from the group consisting of castor oil, partially dehydrated castor oil having a hydroxyl equivalent weight of 600-800, a partially hydrolyzed polyvinylester having a hydroxyl equivalent weight of 300-600, a partially hydrolyzed copolymer of vinyl chloride and vinyl ester having a hydroxyl equivalent weight of 300-600, and a polymer of a monovinyl, monoalphamethyl or monoalphaethyl ether of an alkylene glycol having 2-6 carbon atoms, said polymer having a hydroxyl equivalent weight of 300-600, and a hydrophobic component having no more than 35 carbon atoms therein and having 1-3 urethane groups per molecule.
Claim 23
Dependent Claim
170 words
An anti-fouling coating deposited on a surface of an object to be submerged in sea water comprising 50-75 percent by weight based on said coating of an organic tin polymer of a monomer having the formula R 3 SnOOCR' wherein R is a lower alkyl, cycloalkyl or aryl radical and R' is a polymerizable radical selected from the group consisting of vinyl, lower alkylvinyl, vinylaryl and lower alkylvinylaryl groups; 19-38 percent by weight of a hydrophilic component selected from the group consisting of castor oil, partially dehydrated castor oil having a hydroxyl equivalent weight of 600-800, a partially hydrolyzed polyvinylester having a hydroxyl equivalent weight of 300-600, a partially hydrolyzed copolymer of vinyl chloride and vinyl ester having a hydroxyl equivalent weight of 300-600, and a polymer of a monovinyl, monoalphamethyl or monoalphaethyl ether of an alkylene glycol having 2-6 carbon atoms, said polymer having a hydroxyl equivalent weight of 300-600, and a hydrophobic component having no more than 35 carbon atoms therein and having 1-3 urethane groups per molecule.
Claim 24
Dependent Claim
94 words
The anti-fouling coating of claim 21, in which said organic tin polymer is derived from a monomer selected from the group consisting of tri-n-butylin p-vinylbenzoate, tri-n-butyltin methacrylate, tri-n-propyltin methacrylate, tri-phenyltin methacrylate and tri-n-propyltin p-vinylbenzoate; said hydrophobic component is castor oil; and said hydrophobic component is the reaction product of a diisocyanate selected from the group consisting of hexamethylene diisocyanate, tolylene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, decylene diisocyanate and phenylene diisocyanate with a monohydric compound selected from the group consisting of ethanol, propanol, butanol and the monoethyl and monopropyl ethers of ethylene and propylene glycols.
Claim 25
Dependent Claim
18 words
The coating of claim 21, in which said hydrophobic component has no more than 20 carbon atoms therein.
Claim 26
Dependent Claim
294 words
The process of protecting a surface of an object from fouling by exposure to sea water comprising the steps of applying to said surface a film-forming composition comprising: (a) 10-22 percent by weight of a hydrophilic component selected from the group consisting of castor oil, partially dehydrated castor oil having a hydroxyl equivalent weight of 600-800, a partially hydrolyzed polyvinylester having a hydroxyl equivalent weight of 300-600, a partially hydrolyzed copolymer of vinyl chloride and vinyl ester having a hydroxyl equivalent weight of 300-600, and a polymer of a monovinyl, monoalphamethylvinyl or monoalphaethylvinyl ether of an alkylene glycol having 2-6 carbon atoms, said polymer having a hydroxyl equivalent weight of 300-600; (b) 2.5-7.5 percent by weight of a hydrophobic component having no more than 35 carbon atoms therein and having 1-3 urethane groups per molecule; (c) 30-50 percent by weight of an organic tin polymer of a monomer having the formula R 3 SnOOCR' wherein R is a lower alkyl, cycloalkyl or aryl radical and R' is a polymerizable radical selected from the group consisting of vinyl, lower alkylvinyl, vinyl aryl and lower alkylvinyl aryl groups; and (d) 20-40 percent by weight of a solvent component having one or more compounds selected from the group consisting of a hydroxyl-containing compound having the formula R"(OH) n' wherein R" represents an aliphatic, arylaliphatic or cycloaliphatic hydrocarbon group having 2-10 carbon atoms and n' is an integer having a value of 1-3, a monoether or monoester of an alkylene glycol having no more than 10 carbon atoms, an aromatic hydrocarbon having a kauri butanol value of 73-105, and a ketone having no more than 10 carbon atoms; and allowing said coating to dry to a hard film before the resultant coated surface is exposed to sea water.
Claim 27
Dependent Claim
294 words
The process of protecting a surface of an object from fouling by exposure to sea water comprising the steps of applying to said surface a film-forming composition comprising: (a) 10-22 percent by weight of a hydrophilic component selected from the group consisting of castor oil, partially dehydrated castor oil having a hydroxyl equivalent weight of 600-800, a partially hydrolyzed polyvinylester having a hydroxyl equivalent weight of 300-600, a partially hydrolyzed copolymer of vinyl chloride and vinyl ester having a hydroxyl equivalent weight of 300-600, and a polymer of a monovinyl, monoalphamethylvinyl or monoalphaethylvinyl ether of an alkylene glycol having 2-6 carbon atoms, said polymer having a hydroxyl equivalent weight of 300-600; (b) 2.5-7.5 percent by weight of a hydrophobic component having no more than 35 carbon atoms therein and having 1-3 urethane groups per molecule; (c) 30-50 percent by weight of an organic tin polymer of a monomer having the formula R 3 SnOOCR' wherein R is a lower alkyl, cycloalkyl or aryl radical and R' is a polymerizable radical selected from the group consisting of vinyl, lower alkylvinyl, vinyl aryl and lower alkylvinyl aryl groups; and (d) 20-40 percent by weight of a solvent component having one or more compounds selected from the group consisting of a hydroxyl-containing compound having the formula R"(OH) n' wherein R" represents an aliphatic, arylaliphatic or cycloaliphatic hydrocarbon group having 2-10 carbon atoms and n' is an integer having a value of 1-3, a monoether or monoester of an alkylene glycol having no more than 10 carbon atoms, an aromatic hydrocarbon having a kauri butanol value of 73-105, and a ketone having no more than 10 carbon atoms; and allowing said coating to dry to a hard film before the resultant coated surface is exposed to sea water.
Claim 28
Dependent Claim
18 words
The process of claim 24, in which said hydrophilic component comprises 10.5-16 percent by weight of said composition.
Claim 29
Dependent Claim
18 words
The process of claim 25, in which said hydrophilic component comprises 3.5-6 percent by weight of said composition.
Claim 30
Dependent Claim
19 words
The process of claim 26, in which said tin polymer component comprises 40-55 percent by weight of said composition.
Claim 31
Dependent Claim
17 words
The process of claim 27, in which said solvent comprises 30-38 percent by weight of said composition.
Claim 32
Dependent Claim
18 words
The process of claim 24, in which said hydrophobic component has no more than 20 carbon atoms therein.
Claim 33
Dependent Claim
18 words
The process of claim 28, in which said hydrophobic component has no more than 20 carbon atoms therein.
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