GB2152947A - Marine coating and certain new terpolymers for use therein - Google Patents

Marine coating and certain new terpolymers for use therein Download PDF

Info

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
Application number
GB08432163A
Other versions
GB2152947B (en
GB8432163D0 (en
Inventor
Cristian Marius Sghibartz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Jotun AS
Original Assignee
Jotun AS
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Jotun AS filed Critical Jotun AS
Publication of GB8432163D0 publication Critical patent/GB8432163D0/en
Publication of GB2152947A publication Critical patent/GB2152947A/en
Application granted granted Critical
Publication of GB2152947B publication Critical patent/GB2152947B/en
Expired legal-status Critical Current

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)

CLAIMS 1. Marine coating comprising a film-forming acrylic polymer, characterised in that the acrylic polymer comprises units of the following monomers: R = H orCH3, R" CH3orC2H5,n = 1 or 2 and R' = C1.4alkyl 2. Marine coating according to claim 1, characterised in that the acrylic polymer comprises units of
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.
GB08432163A 1984-01-02 1984-12-20 Marine coating and certain new terpolymers for use therein Expired GB2152947B (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Patent Citations (2)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Similar Documents

Publication Publication Date Title
GB2152947A (en) Marine coating and certain new terpolymers for use therein
US5302192A (en) Anti-fouling coating compositions
EP1016681A3 (en) Silyl (meth)acrylate copolymers, processes for preparing the same, antifouling paint compositions containing the silyl (meth)acrylate copolymers, antifouling coating films formed from the antifouling paint compositions, antifouling methods using the antifouling paint compositions, and hulls or underwater structures coated with the antifouling coating films
US4485197A (en) Resinous composition and antifouling paint
EP0289481A2 (en) Self-polishing antifouling paints
US5439511A (en) Coating varnish composition and antifouling coating composition
EP0228378B1 (en) Anti-fouling paint
CA2400816A1 (en) Metal-free binders for self-polishing antifouling paints
US4157999A (en) Anti-fouling paint composition
AU2001246479C1 (en) Improved paint compositions
JPS60184513A (en) Production of graft polymer
KR100215527B1 (en) New (meth)acrylic resin compositions for marine antifouling paints and corresponding paint compositions
AU2001246479A1 (en) Improved paint compositions
US4761439A (en) Anti-fouling paint compositions
US6710117B2 (en) Marine paint compositions
JPH04103671A (en) Antifouling paint composition
JPH059415A (en) Antifouling coating composition
JP2651499B2 (en) Resin composition for antifouling paint
JP2614467B2 (en) Resin composition for antifouling paint
KR100357451B1 (en) Process for producing antifouling polymer and antifouling paint composition containing the same
JPH04224876A (en) Resin composition slightly soluble in water and coating material made by using it
JP2614466B2 (en) Resin composition for antifouling paint
RU2069667C1 (en) Copolymers of esters of metacrylic acid as film-forming components for binders and coatings
GB2204046A (en) Self-polishing antifouling paints
GB2214921A (en) Self-polishing antifouling paints

Legal Events

Date Code Title Description
PCNP Patent ceased through non-payment of renewal fee

Effective date: 20021220