SE465574B - MARIN FAERG AND ACRYLIC POLYMER BEFORE USING THERE - Google Patents

MARIN FAERG AND ACRYLIC POLYMER BEFORE USING THERE

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Publication number
SE465574B
SE465574B SE8406666A SE8406666A SE465574B SE 465574 B SE465574 B SE 465574B SE 8406666 A SE8406666 A SE 8406666A SE 8406666 A SE8406666 A SE 8406666A SE 465574 B SE465574 B SE 465574B
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Sweden
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units
weight
monomer
acrylic polymer
marine
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SE8406666A
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Swedish (sv)
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SE8406666L (en
SE8406666D0 (en
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C M Sghibartz
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Jotun As
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Publication of SE8406666D0 publication Critical patent/SE8406666D0/en
Publication of SE8406666L publication Critical patent/SE8406666L/en
Publication of SE465574B publication Critical patent/SE465574B/en

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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

Description

15 20 25 30 35 465 574 2 triorganotennesterenheter. Nämnda metylakrylat- och etylakrylatenheter hydrolyseras i viss utsträckning i vatten och ger den färdiga beläggningen en självpole- rande effekt. På grund av den resulterande sampolyme- rens låga hydrolyshastighet är emellertid den själv- polerande effekten inte helt tillfredsställande. 15 20 25 30 35 465 574 2 triorganotene ester units. Said methyl acrylate and ethyl acrylate units are hydrolyzed to a certain extent in water and give the finished coating a self-polishing effect. However, due to the low hydrolysis rate of the resulting copolymer, the self-polishing effect is not entirely satisfactory.

Enligt föreliggande uppfinning åstadkommes en marin färg, som förutom vanliga färgkomponenter, såsom pigment, färgämnen, lösningsmedel osv, innehåller en sampolymer som omfattar enheter av följande monomerer: 1. CH2=?-COO(CH -O-R" R R = H eller CH3, R" = CH3 eller C2H5, n = 2, och 2. CH 2)n 1 eller =?-COOR' CH3 R' = C1_4-alkyl Enheterna av monomer nr 1 hydrolyseras lätt för att 2 ge fria karboxylgrupper, vilket resulterar i en polymer som gradvis nedbrytes så att det uppnås en självpoleran- de effek .According to the present invention there is provided a marine dye which, in addition to common dye components such as pigments, dyes, solvents, etc., contains a copolymer comprising units of the following monomers: 1. CH 2 =? - COO (CH -OR "RR = H or CH "= CH 3 or C 2 H 5, n = 2, and 2. CH 2) n 1 or =? - COOR 'CH 3 R' = C 1-4 alkyl The units of monomer No. 1 are easily hydrolyzed to give 2 free carboxyl groups, resulting in a polymer which is gradually degraded so that a self-polishing effect is achieved.

Monomer nr 2 föreligger för att göra filmen tillräck- ligt hård.Monomer No. 2 is present to make the film hard enough.

Sampolymeren som används i den marina färgen enligt föreliggande uppfinning innehåller vanligtvis från 15 till 80 vikt% av monomer nr 1 och från 20 till 85 vikt% av monomer nr 2.The copolymer used in the marine paint of the present invention usually contains from 15 to 80% by weight of monomer No. 1 and from 20 to 85% by weight of monomer No. 2.

En föredragen representant för monomer nr_l är 2- metoxietylakrylat och en föredragen representant för monomer nr 2 är metylmetakrylat.A preferred representative of monomer No. 1 is 2-methoxyethyl acrylate and a preferred representative of monomer No. 2 is methyl methacrylate.

En marin färg, som omfattar en sampolymer som inne- håller enheter av de ovannämnda två monomererna nr l och nr 2, kan, som påpekats ovan, också innehålla bio- cida komponenter för att uppnå den önskade biocida ef- fekten, såsom koppar(I)oxid, ditiokarbamater och tri- organotennföreningar, som är kända inom tekniken.A marine dye comprising a copolymer containing units of the above-mentioned two monomers No. 1 and No. 2 may, as pointed out above, also contain biocidal components to achieve the desired biocidal effect, such as copper (I oxide, dithiocarbamates and triorganotin compounds known in the art.

Förutom de båda typer av monomerer som angivits ovan, rv 10 15 20 25 30 35 574 465 3 :an sampolymererna som används i de marina färgerna en- ligt uppfinningen också innehålla enheter av triorgano- tennakrylater och -metalkrylater. Exempel på sådana triorganotennmonomerer är tributyltennmetakrylat och -akrylat, tripropyltennmetakrylat och -akrylat och tri- fenyltennmetakrylat och -akrylat. Triorganotennmonome- rerna kan utgöra upp till 60, särskilt 1-55 vikt% av sampolymeren (terpolymer). Monomer nr 1 är då normalt närvarande i en mängd av l-80 vikt%, särskilt 5-40 vikt%, och monomer nr 2 är då normalt närvarande i en mängd av 20-85, särskilt 20-70 vikt%.In addition to the two types of monomers listed above, the copolymers used in the marine paints of the invention also contain units of triorganotin acrylates and metal acrylates. 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, in particular 1-55% by weight of the copolymer (terpolymer). Monomer No. 1 is then normally present in an amount of 1-80% by weight, especially 5-40% by weight, and monomer No. 2 is then normally present in an amount of 20-85, especially 20-70% by weight.

Sådana terpolymerer är nya och representerar ett ytterligare särdrag hos uppfinningen.Such terpolymers are novel and represent a further feature of the invention.

Sampolymererna som innehåller monomererna nr l och 2 kan framställas genom vanlig polymerisation av lämp- liga monomerer under användning av lämpliga initiatorer och polymerisationsbetingelser. När man önskar fram- ställa en sampolymer (terpolymer), som också innehåller triorganotennmetakrylat- eller -akrylatenheter, kan detta genomföras antingen genom att polymerisera mono- mererna nr l och 2 tillsammans med den önskade triorga- notennmetakrylat- eller -akrylatmonomeren, eller så kan monomererna nr 1 och 2 polymeriseras med metakryl- eller akrylsyra, och karboxylgrupperna på den resulte- rande polymeren förestras därefter med triorganotenn- grupper på i och för sig känt sätt.The copolymers containing monomers Nos. 1 and 2 can be prepared by conventional polymerization of suitable monomers using suitable initiators and polymerization conditions. When it is desired to prepare a copolymer (terpolymer) which also contains triorganotin methacrylate or acrylate units, this can be done either by polymerizing monomers Nos. 1 and 2 together with the desired triorganotin methacrylate or acrylate monomer, or the monomers Nos. 1 and 2 are polymerized with methacrylic or acrylic acid, and the carboxyl groups on the resulting polymer are then esterified with triorganotin groups in a manner known per se.

Exempel l Metylmetakrylat (300 g, 3,00 mol) och 2-metoxiety1- akrylat (200 g, 1,54 mol) upplöstes i xylen (750 g).Example 1 Methyl methacrylate (300 g, 3.00 mol) and 2-methoxyethyl) acrylate (200 g, 1.54 mol) were dissolved in xylene (750 g).

Azobisisobutyronitril (4 g, 0,024 mol) tillsattes och lösningen uppvärmdes till 75°C under omröring och under kvävetillsats.Azobisisobutyronitrile (4 g, 0.024 mol) was added and the solution was heated to 75 ° C with stirring and under nitrogen addition.

Polymerisationen genomfördes vid den ovan angivna temperaturen i fem timmar och övervakades genom föränd- ring av brytningsindex.The polymerization was carried out at the above temperature for five hours and monitored by changing the refractive index.

Temperaturen höjdes till l00°C i trettio minuter för att förstöra eventuell återstående katalysatoraktivitet. 10 15 20 25 30 35 465 574 4 Man erhöll en lösning av en sampolymer av metyl- metakrylat-2-metoxietylakrylat (60:40 efter vikt).The temperature was raised to 100 ° C for thirty minutes to destroy any remaining catalyst activity. A solution of a copolymer of methyl methacrylate-2-methoxyethyl acrylate (60:40 by weight) was obtained.

Exempel 2 Tributyltennmetakrylat (150 g, 0,40 mol), metyl- du metakrylat (250 g, 2,50 mol) och 2-metoxietylakrylat (100 g, 0,77 mol) löstes i xylen (750 g). Azobisiso- butyronitril ( 4 g, 0,02 mol) tillsattes och polyneri- sationen företogs på liknande sätt som i exempel l.Example 2 Tributyltin methacrylate (150 g, 0.40 mol), methyl du methacrylate (250 g, 2.50 mol) and 2-methoxyethyl acrylate (100 g, 0.77 mol) were dissolved in xylene (750 g). Azobisisobutyronitrile (4 g, 0.02 mol) was added and the polynerization was carried out in a similar manner to Example 1.

Man erhöll en lösning av en terpolymer av tributyl- tennmetakrylat - metylmetakrylat - 2-metoxietylakrylat (30:50:20 efter vikt).A solution of a terpolymer of tributyltin methacrylate - methyl methacrylate - 2-methoxyethyl acrylate (30:50:20 by weight) was obtained.

Exempel 3 Tributyltennmetakrylat (275 g, 0,73 mol), metyl- metakrylat (210 g, 2,10 mol) och 2-metoxietylakrylat (15 g, 0,12 mol) upplöstes i xylen (750 g). Azobisiso- butyronitril (4 g, 0,02 mol) tillsattes och polymerisa- tionen genomfördes på liknande sätt som i exempel 1.Example 3 Tributyltin methacrylate (275 g, 0.73 mol), methyl methacrylate (210 g, 2.10 mol) and 2-methoxyethyl acrylate (15 g, 0.12 mol) were dissolved in xylene (750 g). Azobisisobutyronitrile (4 g, 0.02 mol) was added and the polymerization was carried out in a similar manner to Example 1.

Man erhöll en lösning av en terpolymer av tributyl- tennmetakrylat - metylmetakrylat - 2-metoxietylakrylat (55:42:3 efter vikt).A solution of a terpolymer of tributyltin methacrylate - methyl methacrylate - 2-methoxyethyl acrylate (55: 42: 3 by weight) was obtained.

Exempel 4 409,2 g av sampolymerlösningen från exempel 1 blan- dades med koppar(I)oxid (365,4 g), zinkoxid (l5l,2 g), Aerosil (kolloidal kiselsyra) (4,0 g), Bentone R'(för- tjockningsmedel) (8,0 g), denaturerad etanol (4,8 g) och xylen (57,4 g) och maldes över natten för att ge en färg med ett förhållande mellan kopper(I)oxid och zinkoxid på 70:30 efter volym.Example 4 409.2 g of the copolymer solution from Example 1 were mixed with copper (I) oxide (365.4 g), zinc oxide (15l, 2 g), Aerosil (colloidal silicic acid) (4.0 g), Bentone R ' (thickener) (8.0 g), denatured ethanol (4.8 g) and xylene (57.4 g) and ground overnight to give a color with a ratio of copper (I) oxide to zinc oxide of 70 : 30 by volume.

Exempel 5 409,2 g av terpolymerlösningen från exempel 2 blan- f dades med koppar(I)oxid (365,4 g), zinkoxid (l5l,2 g), (8,0 g), (4,8 g) och xylen (57,4 g) och maldes Aerosil '(4,0 g), Bentone denaturerad etanol över natten för att ge en färg med ett förhållande mellan koppar(I)oxid och zinkoxid på 70:30 efter volym.Example 5 409.2 g of the terpolymer solution from Example 2 were mixed with copper (I) oxide (365.4 g), zinc oxide (115, 2 g), (8.0 g), (4.8 g) and xylene (57.4 g) and ground Aerosil '(4.0 g), Bentone denatured ethanol overnight to give a color with a ratio of copper (I) oxide to zinc oxide of 70:30 by volume.

Wxempel 6 Som exempel 4 med det undantaget att polymeren från 17,3 10 15 465 574 5 exempel 1 ersatts med den från exempel 3.Example 6 As Example 4 with the exception that the polymer from Example 17.3 was replaced with that from Example 3.

Färgen, som beskrivits i exemplen 4,_5 och 6, under- söktes med hänsyn till polering under användning av en rotorapparat med en periferihastighet på 17 knop (ca 31 km/h) i sjövatten vid en genomsnittstemperatur pà 23°C.The paint described in Examples 4, 5 and 6 was tested for polishing using a rotor apparatus with a peripheral speed of 17 knots (about 31 km / h) in seawater at an average temperature of 23 ° C.

En kommersiellt framgångsrik självpolerande färg innehållande organotennpolymerer (X) användes som refe- rens. Proven utfördes över en period på 90 dagar, och färgens tjocklek bestämdes genom elektromagnetisk in- duktion.A commercially successful self-polishing paint containing organotin polymers (X) was used as a reference. The tests were performed over a period of 90 days, and the thickness of the paint was determined by electromagnetic induction.

Färg poleringshastighet (um/âr) X 60 Exempel 4 52 Exempel 5 72 Exempel 6 _80Color polishing speed (μm / year) X 60 Example 4 52 Example 5 72 Example 6 _80

Claims (3)

465 574 10 15 20 25 30 35 PATENTKRAV l. Marin färg som omfattar en filmbildande akryl- polymer, k ä n n e t e c k n a d därav, att akryl- polymeren innehåller enheter av följande monomerer: l) CH2=ç-COO(CH2)n~0-R" R R = H eller CH3, R" = CH3 eller CZH5, n = l eller 2 och 2) CH2=ç-COOR' CH3 R' = C1_4-alkyl. 2. Marin färg enligt krav l, k ä n n e t e c k - n a d därav, att akrylpolymeren innehåller enheter av l) 2-metoxietylakrylat och 2) metylmetakrylat. 3. Marin färg enligt något av kraven 1 och 2, k ä n n e t e c k n a d därav, att akrylpolymeren inne- håller l5-80 víkt% enheter av monomer l och 20-85 vikt% enheter av monomer 2. 4. Marin färg enligt något av kraven 1-3, k ä n - n e t e c k n a d därav, att akrylpolymeren också inne- håller enheter av ett eller flera triorganotennmetakry- later eller -akrylater. 5. Marin färg enligt krav 4, k ä n n e t e c k - n a d därav, att akrylpolymeren innehåller enheter av tributyltennmetakrylat. 6. Marin färg enligt något av kraven 4 och 5, k ä n n e t e c k n a d därav, att akrylpolymeren inne- håller upp till 60 vikt% av nämnda triorganotennmeta- krylat- eller -akrylatenheter. 7. Akrylterpolymer för användning som komponent i marin färg, k ä n n e t e c k n a d därav, att den innehåller enheter av följande monomerer: 1) CH2=?-COO(CH n-O-R" R 2) 10 15 20 _12: O\ U1 G1 w -Išu 7 H eller CH3, R" = CH3 eller C2 2) CH =C-COOR' I CH3 R' = Cl_4-alkyl, och 3) triorganotennmetakrylater eller -akrylater. 1 eller 2, R = H5, n = 2 8. Akrylterpolymer för användning som komponent i marin färg enligt krav 7, k ä n n e t e c k n a d därav, att den innehåller enheter av:465 574 10 15 20 25 30 35 CLAIMS 1. Marine paint comprising a film-forming acrylic polymer, characterized in that the acrylic polymer contains units of the following monomers: l) CH 2 = ç-COO (CH 2) n ~ 0- R "RR = H or CH 3, R" = CH 3 or C 2 H 5, n = 1 or 2 and 2) CH 2 = α-COOR 'CH 3 R' = C 1-4 alkyl. Marine paint according to claim 1, characterized in that the acrylic polymer contains units of 1) 2-methoxyethyl acrylate and 2) methyl methacrylate. Marine paint according to any one of claims 1 and 2, characterized in that the acrylic polymer contains 15-80% by weight of units of monomer 1 and 20-85% by weight of units of monomer 2. Marine paint according to any one of claims 1-3, characterized in that the acrylic polymer also contains units of one or more triorganotin methacrylates or acrylates. Marine paint according to claim 4, characterized in that the acrylic polymer contains units of tributyltin methacrylate. Marine paint according to any one of claims 4 and 5, characterized in that the acrylic polymer contains up to 60% by weight of said triorganotin metacrylate or acrylate units. 7. Acrylic terpolymer for use as a component in marine color, characterized in that it contains units of the following monomers: 1) CH2 =? - COO (CH nOR "R 2) 10 15 20 _12: O \ U1 G1 w -Išu 7 H or CH 3, R "= CH 3 or C 2 2) CH = C-COOR 'in CH 3 R' = C 1-4 alkyl, and 3) triorganotin methacrylates or acrylates. 1 or 2, R = H5, n = 2 8. Acrylic terpolymer for use as a component in marine color according to claim 7, characterized in that it contains units of: 1. l) 2-metoxietylakrylat1. 1) 2-methoxyethyl acrylate 2. ) metylmetakrylat och2.) methyl methacrylate and 3. ) tributyltennmetakrylat. 9. Akrylterpolymer för användning som komponent färg enligt något av kraven 7 och 8, k ä n - c k n a d därav, att den innehåller l-80 vikt% 20-85 vikt% enheter av monomer i marin n e t e enheter av monomer 1, 2 och upp till 60 vikt% enheter av monomer 3. 10. Akrylterpolymer för användning som komponent i marin färg enligt krav 9, k ä n n e t e c k n a d därav, att den innehåller 5-40 vikt% enheter av monomer 1, 20~70 vikt% enheter av monomer 2 och l-55 vikt% en- heter av monomer 3.3.) tributyltin methacrylate. Acrylic terpolymer for use as a component paint according to any one of claims 7 and 8, characterized in that it contains 1-80% by weight of 20-85% by weight of units of monomer in marine units of monomer 1, 2 and up to 60% by weight of units of monomer 3. Acrylic terpolymer for use as a component in marine color according to claim 9, characterized in that it contains 5-40% by weight of units of monomer 1, 20 ~ 70% by weight of units of monomer 2 and 1-55% by weight of units of monomer 3.
SE8406666A 1984-01-02 1984-12-28 MARIN FAERG AND ACRYLIC POLYMER BEFORE USING THERE SE465574B (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
SE8406666D0 SE8406666D0 (en) 1984-12-28
SE8406666L SE8406666L (en) 1985-07-03
SE465574B true SE465574B (en) 1991-09-30

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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) ES8607995A1 (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)

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KR850004976A (en) 1985-08-19
DE3446971A1 (en) 1985-07-11
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AU3714784A (en) 1985-07-11
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NO156493C (en) 1987-09-30
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SE8406666L (en) 1985-07-03
DK172317B1 (en) 1998-03-16
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FR2557585B1 (en) 1993-10-08
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NO840005L (en) 1985-07-03
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GB2152947A (en) 1985-08-14
PT79776A (en) 1985-01-01
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IT1178318B (en) 1987-09-09
JPS60158211A (en) 1985-08-19
AU570530B2 (en) 1988-03-17
DE3446971C2 (en) 1995-09-28
NL192114C (en) 1997-02-04
HK94892A (en) 1992-12-04
FR2557585A1 (en) 1985-07-05
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