GB2152947A - Marine coating and certain new terpolymers for use therein - Google Patents
Marine coating and certain new terpolymers for use therein Download PDFInfo
- Publication number
- GB2152947A GB2152947A GB08432163A GB8432163A GB2152947A GB 2152947 A GB2152947 A GB 2152947A GB 08432163 A GB08432163 A GB 08432163A GB 8432163 A GB8432163 A GB 8432163A GB 2152947 A GB2152947 A GB 2152947A
- Authority
- GB
- United Kingdom
- Prior art keywords
- units
- weight
- monomer
- percent
- marine coating
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1656—Antifouling paints; Underwater paints characterised by the film-forming substance
- C09D5/1662—Synthetic film-forming substance
- C09D5/1668—Vinyl-type polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/062—Copolymers with monomers not covered by C09D133/06
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Laminated Bodies (AREA)
Abstract
Marine coating comprising a film-forming acrylic polymer, characterised in that the acrylic polymer comprises units of the following monomers: <IMAGE> is disclosed. Acrylic terpolymers comprising units of the following monomers: <IMAGE> 3. triorganotin methacrylates or acrylates, are also disclosed.
Description
SPECIFICATION
Marine coating and certain new terpolymers for use therein
The present invention relates to new marine coatings and certain new terpolymers which are useful components therein.
There are known marine coatings in which an essential component is a copolymer containing units of alkyl acrylates and methacrylates and units of triorganotin esters of acrylic and methacrylic acid. The alkyl acrylate and methacrylate units impart hardness to the film obtained when the marine coating is applied to a substrate, and the triorganotin ester units impart biocidal as well as self-polishing effect. During use the triorganotin units are split off from the polymer by hydrolysis and/or ion exchange, whereby the film of the marine coating exerts a desired biocidal effect. At the same time the film is degraded, and this results in the self-polishing effect.
Thus, to obtain a satisfactory self-polishing effect, a certain amount of triorganotin units must be present in the copolymer used in the marine coatings since the self-polishing effect is a consequence of the cleavage of said units. On the other hand, it is desired to keep the amount of triorganotin units as low as possible, with due regard to the desired biocidal and self-polishing effect, since the triorganotin monomers are rather expensive and also have a softening effect on the copolymer.
Copolymers of the above type are disclosed i.a. in British Patent No. 1 457 590.
In Norwegian Patent Application 81.3553 it is suggested to replace some or all of the triorganotin ester units by methyl acrylate and/or ethyl acrylate units. The marine coating may contain some additional biocide, particularly if the copolymer does not contain any triorganotin ester units. Said methyl acrylate and ethyl acrylate units will to some extent be hydrolysed in water, and will impart a selfpolishing effect to the final coating. However, due to the low rate of hydrolysis of the resulting copolymer, the selfpolishing effect will not be entirely satisfactory.
According to the present invention there is provided a marine coating which in addition to ordinary paint components such as pigments, dyes, solvents, etc. contain a copolymer units of the following monomers:
F HorCH3,R"=CHsorC2H5,n = 1 or2, and
R' = C1.4 alkyl
The units of monomer no. 1 are readily hydrolysed to form free carboxyl groups, resulting in a polymer which is gradually degraded to provide a self-polishing effect.
Monomer No. 2 is present to impart sufficient hardness to the film.
The copolymer used in the marine coatings of the present invention usually contain from 15 to 80 percent by weight of monomer No. 1 and from 20 to 85 percent by weight of monomer No. 2.
A preferred representative of monomer No. 1 is 2-methoxyethyl acrylate, and a preferred representative of monomer No. 2 is methyl methacrylate.
As pointed out above, a marine coating which comprises a copolymer containing units of the above two monomers No. 1 and No. 2, may also contain biocidal components to obtain the desired biocidal effect, such as cuprous oxide, dithiocarbamates and triorganotin compounds as known in the state of art.
In addition to the two types of monomer disclosed above, the copolymers used in the marine coatings of the present invention may also contain units of triorganotin acrylates and methacrylates. Examples of such triorganotin monomers are tributyltin methacrylate and acrylate, tripropyltin methacrylate and acrylate and triphenyltin methacrylate and acrylate. The triorganotin monomers may constitute up to 60, particularly 1-55, percent by weight of the copolymer (terpolymer). Monomer No. 1 is then normally present in an amount of 1-80 percent by weight, particularly 5-40 percent by weight, and monomer No. 2 is then normally present in an amount of 20-85, particularly 20-70 percent by weight.
Such terpolymers are new and represent a further feature of the invention.
The copolymers containing monomers No. 1 and 2 may be prepared by ordinary polymerisation of the suitable monomers, using suitable initiators and polymerisation conditions. When it is desired to prepare a copolymer (terpolymer) which also contains triorganotin methacrylate or acrylate units, this may be done either by polymerising monomers No. 1 and 2 together with the desired triorganotin methacrylate or acrylate monomer, or monomers No. 1 and 2 may be polymerised with methacrylic or acrylic acid, and the carboxyl groups on the resulting polymer are then esterified with triorganotin groups in a per se known manner.
Example 1
Methyl methacrylate (300 g; 3.00 mole) and 2-methoxyethyl acrylate (200 g; 1.54 mole) were dissolved in xylene 750 g). Azobisisobutyronitrile (4 g; 0.024 mole) was added and the solution heated to 75"C, with stirring and under nitrogen.
The polymerisation was carried out at the above temperature for a period of 5 hours and was monitored by the change in refractive index.
The temperature was raised to 100 C for 30 minutes to destroy any residual activity of the initiator.
The solution obtained was that of a copolymer of methyl methacrylate - 2-methoxyethyl acrylate (60:40 by weight).
Example 2
Tributyltin methacrylate (150 g; 0.40 mole), methyl methacrylate (250 g; 2.50 mole) and 2-methoxyethyl acrylate (100 g; 0.77 mole) were dissolved in xylene (750 g).
Azobisisobutyronitrile (4 g; 0.02 mole) was added and polymerisation was carried out in a similar manner as in example 1.
The solution obtained was that of a terpolymer of tributyltin methacrylate - methyl methacrylate 2-methoxyethyl acrylate (30:50:20 by weight).
Example 3
Tributyltin methacrylate (275 g; 0.73 mole), methyl methacrylate (210 g; 210 mole) and 2-methoxyethyl acrylate (15 g; 0.12 mole) were dissolved in xylene (750 g).
Azobisisobutyronitrile (4 g; 0.02 mole) was added and polymerisation was carried out in a similar manner as in example 1.
The solution obtained was that of a terpolymer of tributyltin methacrylate - methyl methacrylate 2-methoxyethyl acrylate (55:42:3 by weight).
Example 4
409.2 g of the copolymer solution from example 1 was mixed with cuprous oxide (365.4 g), zinc oxide (151.2 g), Aerosil (colloidal silica) (4.0 g), Bentona (thickening agent) (8.0 g), denaturated ethanol (4.8 g) and xylene (57.4 g), and milled overnight to produce a paint with a cuprous oxide - zinc oxide ratio of 70:30 by volume.
Example 5
409.2 g of the terpolymer solution from example 2 was mixed with cuprous oxide (365.4 g), zinc oxide (151.2 g), Aerosilig (4.0 g), Bentone (8.0 g), denaturated ethanol (4.8 g) and xylene (57.4 g) and milled overnight to produce a paint with a cuprous oxide - zinc oxide ratio of 70:30 by volume.
Example 6
As Example 4, with the exception that the polymer of Example 1 was replaced by that of Example 3.
The paints described in Example 4, 5 and 6 were tested for polishing using a rotor apparatus with a peripheral speed of 17 knots (about 31 km/h), in sea water, at an average temperature of 23"C.
A commercially successful selfpolishing paint containing organotin polymer (X) was used as reference.
The test was carried out over a period of 90 days and the thickness of the paint film was determined by electromagnetic induction.
Paint Polishing Rate (m/yeari x 60
Example 4 52
Example 5 72
Example 6 80
Claims (12)
1. 2-methoxyethyl acrylate, and
2. methyl methacrylate.
3. Marine coating according to any of claims 1 and 2, characterised in that the acrylic polymer comprises 15-80 percent by weight of monomer 1 units, and 20-85 percent by weight of monomer 2 units.
4. Marine coating according to any of claims 1-3, characterised in that the acrylic polymer also comprises units of one or more triorganotin metchacrylates or acrylates.
5. Marine coating according to claim 4, characterised in that the acrylic polyer comprises units of tributyltin methacrylate.
6. Marine coating according to any of claims 4 and 5, characterised in that the acrylic polymer comprises up to 60 percent by weight of said triorganotin methacrylate or acrylate units.
7. Acrylicterpolymer characterised in that it comprises units of the following monomers:
R = H or CH3, R" = CH3 or C2H5, n = 1 or 2
R' = C1.4alkyl, and
3. triorganotin methacrylates or acrylates.
8. Acrylic terpolymer according to claim 7, characterised in that it comprises units of:
1. 2-methoxyethyl acrylate
2. methyl methacrylate, and
3. tributyltin methacrylate.
9. Acrylicterpolymer according to any of claims 7 and 8, characterised in that it contains 1-80 percent by weight of monomer 1 units, 20-85 percent by weight of monomer 2 units and up to 60 percent by weight of monomer 3 units.
10. Acrylic terpolymer according to claim 9, characterised in that it contains 5-40 percent by weight of monomer 1 units, 20-70 percent by weight of monomer 2 units and 1-55 percent by weight of monomer 3 units.
11. Marine coating according to claim 1 substantially as herein described with particular reference to the
Examples.
12. Acrylicterpolymer according to claim 7 substantially as herein described with particular reference to the Examples.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NO840005A NO156493C (en) | 1984-01-02 | 1984-01-02 | MARIN PAINTING INCLUDING A MOVIE-forming ACRYLIC POLYMER AND AN ACRYLIC POLYMER FOR USE IN THE PAINTING. |
Publications (3)
Publication Number | Publication Date |
---|---|
GB8432163D0 GB8432163D0 (en) | 1985-01-30 |
GB2152947A true GB2152947A (en) | 1985-08-14 |
GB2152947B GB2152947B (en) | 1987-09-30 |
Family
ID=19887419
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB08432163A Expired GB2152947B (en) | 1984-01-02 | 1984-12-20 | Marine coating and certain new terpolymers for use therein |
Country Status (19)
Country | Link |
---|---|
JP (1) | JPS60158211A (en) |
KR (1) | KR930008744B1 (en) |
AU (1) | AU570530B2 (en) |
BE (1) | BE901426A (en) |
BR (1) | BR8406783A (en) |
CA (1) | CA1260186A (en) |
DE (1) | DE3446971C2 (en) |
DK (1) | DK172317B1 (en) |
ES (1) | ES539165A0 (en) |
FR (1) | FR2557585B1 (en) |
GB (1) | GB2152947B (en) |
GR (1) | GR82615B (en) |
HK (1) | HK94892A (en) |
IT (1) | IT1178318B (en) |
NL (1) | NL192114C (en) |
NO (1) | NO156493C (en) |
PT (1) | PT79776B (en) |
SE (1) | SE465574B (en) |
SG (1) | SG79990G (en) |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1993002146A1 (en) * | 1991-07-19 | 1993-02-04 | J.C. Hempel's Skibsfarve-Fabrik A/S | Paint composition |
US5254632A (en) * | 1991-07-02 | 1993-10-19 | Rohm Gmbh Chemische Fabrik | Method of manufacturing polyalkyl methacrylate macromonomers, and use of same in the manufacture of comb polymers |
US5288828A (en) * | 1993-03-08 | 1994-02-22 | The Sherwin-Williams Company | Dispersant polymers |
EP0841380A1 (en) | 1996-11-07 | 1998-05-13 | Witco GmbH | Method of making polymeric binders and use thereof in antifouling paints |
US5821300A (en) * | 1996-11-07 | 1998-10-13 | Witco Gmbh | Process for preparing polymeric binders and their use for antifouling paint systems |
US7118616B2 (en) | 2001-10-30 | 2006-10-10 | Sigma Coatings B.V. | Paint compositions comprising esters of rosin and process of production thereof |
WO2011092143A1 (en) | 2010-01-26 | 2011-08-04 | Jotun A/S | Antifouling composition |
WO2011151438A2 (en) | 2010-06-04 | 2011-12-08 | Jotun A/S | Antifouling coating |
EP2708594A1 (en) | 2012-09-18 | 2014-03-19 | Jotun A/S | Cleaning process |
EP2725073A1 (en) | 2012-10-23 | 2014-04-30 | Jotun A/S | Antifouling coating composition |
WO2014064048A1 (en) | 2012-10-23 | 2014-05-01 | Jotun A/S | Antifouling coating composition |
WO2014096102A1 (en) | 2012-12-19 | 2014-06-26 | Jotun A/S | Silyl ester copolymer |
EP2902453A1 (en) | 2014-01-31 | 2015-08-05 | Jotun A/S | Antifouling Composition |
EP2902452A1 (en) | 2014-01-31 | 2015-08-05 | Jotun A/S | Antifouling composition |
EP3078715A1 (en) | 2015-04-09 | 2016-10-12 | Jotun A/S | Antifouling composition |
DE102017126335A1 (en) | 2016-11-11 | 2018-05-17 | Jotun A/S | Antifouling composition |
DE102017126336A1 (en) | 2016-11-11 | 2018-05-17 | Jotun A/S | Antifouling composition |
CN109777178A (en) * | 2017-11-15 | 2019-05-21 | 佐敦有限公司 | Antifouling composition |
EP4234643A2 (en) | 2016-11-11 | 2023-08-30 | Jotun A/S | Antifouling composition |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3196361B2 (en) * | 1991-12-25 | 2001-08-06 | 日立化成工業株式会社 | Resin composition for paint and antifouling paint for underwater structures |
FR2729965B1 (en) * | 1995-01-26 | 2000-05-19 | France Etat | SELF-POLISHING ANTI-FOULING PAINTS |
EP1475415A1 (en) | 2003-05-07 | 2004-11-10 | SigmaKalon Services B.V. | Silyl esters, their use in binder systems and paint compositions and a process of production thereof |
FR2930778A1 (en) | 2008-04-30 | 2009-11-06 | Bluestar Silicones France Soc | ARTICLE HAVING ANTIFOULING PROPERTIES AND INTENDED FOR USE IN AQUATIC APPLICATIONS, IN PARTICULAR MARINE |
WO2009156609A2 (en) | 2008-05-29 | 2009-12-30 | Bluestar Silicones France | Article having antifouling properties for aquatic and particularly sea use |
US9744527B2 (en) | 2008-05-29 | 2017-08-29 | Bluestar Silicones France Sas | Article having antifouling properties for aquatic and particularly sea use |
FR2999980A1 (en) | 2012-12-20 | 2014-06-27 | Bluestar Silicones France | ARTICLE HAVING ANTIFOULING PROPERTIES AND INTENDED FOR USE IN AQUATIC APPLICATIONS, IN PARTICULAR MARINE |
KR101779681B1 (en) | 2012-12-20 | 2017-09-18 | 블루스타 실리콘즈 프랑스 에스에이에스 | Article with antifouling properties, intended for aquatic uses and, in particular, for marine uses |
FR3014107A1 (en) | 2013-12-03 | 2015-06-05 | Bluestar Silicones France | ARTICLE HAVING ANTIFOULING PROPERTIES AND INTENDED FOR USE IN AQUATIC APPLICATIONS, IN PARTICULAR MARINE |
CN112771090A (en) * | 2018-09-26 | 2021-05-07 | 三菱化学株式会社 | Copolymer for inhibiting protein adhesion, method for producing copolymer, resin modifier, molding material, composition containing copolymer, coating film, and article |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB988171A (en) * | 1960-04-14 | 1965-04-07 | Vinyl Products Ltd | Improvements in or relating to thermosetting resin compositions |
GB1292953A (en) * | 1968-10-22 | 1972-10-18 | Hydron Ltd | Coating compositions based on acrylate and/or methacrylate copolymers |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1952721A1 (en) * | 1968-10-22 | 1970-09-10 | Hydron Ltd | Coating agent for use on humans or animals |
GB1457590A (en) * | 1974-04-03 | 1976-12-08 | Int Paint Co | Marine paint |
JPS55164261A (en) * | 1979-06-08 | 1980-12-20 | Chugoku Toryo Kk | Antifouling coating material |
DE3170163D1 (en) * | 1980-10-30 | 1985-05-30 | Int Paint Plc | Marine paint |
JPS5776012A (en) * | 1980-10-31 | 1982-05-12 | Mitsubishi Rayon Co Ltd | Preparation of high polymeric acrylic resin containing triorganotin |
JPS58118868A (en) * | 1982-01-07 | 1983-07-15 | Nippon Paint Co Ltd | Resin composition for antifouling paint |
JPS58180565A (en) * | 1982-04-16 | 1983-10-22 | Nippon Oil & Fats Co Ltd | Antifouling coating |
-
1984
- 1984-01-02 NO NO840005A patent/NO156493C/en not_active IP Right Cessation
- 1984-12-19 DK DK610484A patent/DK172317B1/en not_active IP Right Cessation
- 1984-12-20 GB GB08432163A patent/GB2152947B/en not_active Expired
- 1984-12-20 NL NL8403867A patent/NL192114C/en not_active IP Right Cessation
- 1984-12-21 IT IT49342/84A patent/IT1178318B/en active
- 1984-12-21 DE DE3446971A patent/DE3446971C2/en not_active Expired - Fee Related
- 1984-12-26 FR FR8419796A patent/FR2557585B1/en not_active Expired - Fee Related
- 1984-12-27 AU AU37147/84A patent/AU570530B2/en not_active Ceased
- 1984-12-28 CA CA000471098A patent/CA1260186A/en not_active Expired
- 1984-12-28 BE BE0/214280A patent/BE901426A/en not_active IP Right Cessation
- 1984-12-28 PT PT79776A patent/PT79776B/en not_active IP Right Cessation
- 1984-12-28 ES ES539165A patent/ES539165A0/en active Granted
- 1984-12-28 SE SE8406666A patent/SE465574B/en not_active IP Right Cessation
- 1984-12-28 GR GR82615A patent/GR82615B/en unknown
- 1984-12-28 BR BR8406783A patent/BR8406783A/en not_active IP Right Cessation
- 1984-12-28 JP JP59274997A patent/JPS60158211A/en active Pending
- 1984-12-29 KR KR1019840008526A patent/KR930008744B1/en not_active IP Right Cessation
-
1990
- 1990-09-29 SG SG799/90A patent/SG79990G/en unknown
-
1992
- 1992-11-26 HK HK948/92A patent/HK94892A/en not_active IP Right Cessation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB988171A (en) * | 1960-04-14 | 1965-04-07 | Vinyl Products Ltd | Improvements in or relating to thermosetting resin compositions |
GB1292953A (en) * | 1968-10-22 | 1972-10-18 | Hydron Ltd | Coating compositions based on acrylate and/or methacrylate copolymers |
Cited By (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5254632A (en) * | 1991-07-02 | 1993-10-19 | Rohm Gmbh Chemische Fabrik | Method of manufacturing polyalkyl methacrylate macromonomers, and use of same in the manufacture of comb polymers |
WO1993002146A1 (en) * | 1991-07-19 | 1993-02-04 | J.C. Hempel's Skibsfarve-Fabrik A/S | Paint composition |
US5288828A (en) * | 1993-03-08 | 1994-02-22 | The Sherwin-Williams Company | Dispersant polymers |
US5360856A (en) * | 1993-03-08 | 1994-11-01 | The Sherwin-Williams Company | Dispersant polymers |
US5430089A (en) * | 1993-03-08 | 1995-07-04 | The Sherwin-Williams Company | Dispersant polymers |
US5554682A (en) * | 1993-03-08 | 1996-09-10 | The Sherwin-Williams Company | Dispersant polymers |
EP0841380A1 (en) | 1996-11-07 | 1998-05-13 | Witco GmbH | Method of making polymeric binders and use thereof in antifouling paints |
US5821300A (en) * | 1996-11-07 | 1998-10-13 | Witco Gmbh | Process for preparing polymeric binders and their use for antifouling paint systems |
US5891935A (en) * | 1996-11-07 | 1999-04-06 | Witco Gmbh | Process for preparing polymeric binders and their use for antifouling paint systems |
US7118616B2 (en) | 2001-10-30 | 2006-10-10 | Sigma Coatings B.V. | Paint compositions comprising esters of rosin and process of production thereof |
WO2011092143A1 (en) | 2010-01-26 | 2011-08-04 | Jotun A/S | Antifouling composition |
WO2011151438A2 (en) | 2010-06-04 | 2011-12-08 | Jotun A/S | Antifouling coating |
EP2708594A1 (en) | 2012-09-18 | 2014-03-19 | Jotun A/S | Cleaning process |
EP2725073A1 (en) | 2012-10-23 | 2014-04-30 | Jotun A/S | Antifouling coating composition |
WO2014064048A1 (en) | 2012-10-23 | 2014-05-01 | Jotun A/S | Antifouling coating composition |
WO2014096102A1 (en) | 2012-12-19 | 2014-06-26 | Jotun A/S | Silyl ester copolymer |
EP2902453A1 (en) | 2014-01-31 | 2015-08-05 | Jotun A/S | Antifouling Composition |
EP2902452A1 (en) | 2014-01-31 | 2015-08-05 | Jotun A/S | Antifouling composition |
EP3078715A1 (en) | 2015-04-09 | 2016-10-12 | Jotun A/S | Antifouling composition |
DE102017126335A1 (en) | 2016-11-11 | 2018-05-17 | Jotun A/S | Antifouling composition |
DE102017126336A1 (en) | 2016-11-11 | 2018-05-17 | Jotun A/S | Antifouling composition |
EP4234643A2 (en) | 2016-11-11 | 2023-08-30 | Jotun A/S | Antifouling composition |
CN109777178A (en) * | 2017-11-15 | 2019-05-21 | 佐敦有限公司 | Antifouling composition |
CN109777178B (en) * | 2017-11-15 | 2022-02-01 | 佐敦有限公司 | Antifouling composition |
Also Published As
Publication number | Publication date |
---|---|
IT8449342A0 (en) | 1984-12-21 |
NO840005L (en) | 1985-07-03 |
IT1178318B (en) | 1987-09-09 |
SE8406666D0 (en) | 1984-12-28 |
SG79990G (en) | 1990-11-23 |
GR82615B (en) | 1985-05-02 |
DE3446971C2 (en) | 1995-09-28 |
GB2152947B (en) | 1987-09-30 |
NL192114C (en) | 1997-02-04 |
DK610484D0 (en) | 1984-12-19 |
ES8607995A1 (en) | 1986-01-01 |
KR850004976A (en) | 1985-08-19 |
AU3714784A (en) | 1985-07-11 |
DK172317B1 (en) | 1998-03-16 |
PT79776B (en) | 1987-01-05 |
NL192114B (en) | 1996-10-01 |
CA1260186A (en) | 1989-09-26 |
NO156493C (en) | 1987-09-30 |
HK94892A (en) | 1992-12-04 |
NL8403867A (en) | 1985-08-01 |
JPS60158211A (en) | 1985-08-19 |
FR2557585B1 (en) | 1993-10-08 |
GB8432163D0 (en) | 1985-01-30 |
DE3446971A1 (en) | 1985-07-11 |
PT79776A (en) | 1985-01-01 |
BE901426A (en) | 1985-06-28 |
KR930008744B1 (en) | 1993-09-13 |
NO156493B (en) | 1987-06-22 |
SE8406666L (en) | 1985-07-03 |
ES539165A0 (en) | 1986-01-01 |
FR2557585A1 (en) | 1985-07-05 |
SE465574B (en) | 1991-09-30 |
AU570530B2 (en) | 1988-03-17 |
BR8406783A (en) | 1985-10-22 |
DK610484A (en) | 1985-07-03 |
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