GB959775A - Copolymers and coating compositions thereof - Google Patents

Copolymers and coating compositions thereof

Info

Publication number
GB959775A
GB959775A GB2655360A GB2655360A GB959775A GB 959775 A GB959775 A GB 959775A GB 2655360 A GB2655360 A GB 2655360A GB 2655360 A GB2655360 A GB 2655360A GB 959775 A GB959775 A GB 959775A
Authority
GB
United Kingdom
Prior art keywords
parts
copolymer
dried
vinyl carbazole
ethyl acrylate
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.)
Expired
Application number
GB2655360A
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.)
Rohm and Haas Co
Original Assignee
Rohm and Haas Co
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 Rohm and Haas Co filed Critical Rohm and Haas Co
Publication of GB959775A publication Critical patent/GB959775A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D133/00Coating 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
    • C09D133/04Homopolymers or copolymers of esters
    • C09D133/06Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09D133/08Homopolymers or copolymers of acrylic acid esters
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00Copolymers 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
    • C08F220/02Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10Esters
    • C08F220/12Esters of monohydric alcohols or phenols
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F26/00Homopolymers and 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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F26/06Homopolymers and 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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
    • C08F26/12N-Vinyl-carbazole

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)

Abstract

A linear addition copolymer contains at least 50% of methyl and/or ethyl acrylate and from 3 to 50% N-vinyl carbazole. The copolymer may also contain one or more of the comonomers, an ester of methacrylic acid and a C1- 18 alkanol, an ester of acrylic acid and a C3- 18 alkanol, acrylonitrile methacrylonitrile, vinyl acetate, styrene, vinyl chloride and vinylidene chloride. The copolymer may also contain 1 to 10% of a copolymerized monomer having a functional group, e.g. a carboxylic acid group in free acid in salt form, an amino group, an amido, including ureido, group, an alcoholic hydroxyl group or an alkoxy methyl group. The functional group may be reactive with a polyisocyanate, polyepoxide or aminoplast condensate. The copolymers may be prepared by bulk, solution or emulsion polymerization using redox catalysts, emulsifying agents and chain regulators. The copolymer may be dispersed in an aqueous medium which may also contain a thermosetting aminoplast or polyepoxide resin-forming condensate and a pigment or dye, e.g. carbon black, iron oxides, chrome yellows, titanium dioxide, lithopone, aluminium bronze, brass, chromium, gold, azo pigments and lakes, phthalocyanine pigments, and vat dyestuffs. The copolymer may be dissolved in such organic solvents as toluene, xylenes, n-butanol, dimethyl-formamide or mixtures thereof. Specifications 518,057 and 579,698 are referred to.ALSO:A pile fabric is back-coated with a composition comprising a copolymer containing at least 50% of methyl and/or ethyl acrylate and from 3 to 50% N-vinyl carbazole (see Division C3) and the coating dried. The preferred copolymers contain also 1-10% of other functional monomers including thermosetting types and generally do not contain more than 25% of the carbazole. The compositions may be applied from aqueous dispersion and may be dried with or without ageing or by heating at 200-750 DEG F. In an example (8) a pile fabric having a cotton base and a pile of viscose rayon and cellulose acetate is back-coated with a paste of 100 parts of a copolymer of 10% N-vinylcarbazole, 87,5% ethyl acrylate and 2,5% itaconic acid with additions dried and cured. This fabric showed slight fraying only after u-v exposure and washing. Specifications 518,057 and 579,698 are referred to.ALSO:Textile substrates, paper, leather or asbestos-cement sheets are treated with a composition comprising a copolymer containing at least 50% of methyl and/or ethyl acrylate and from 3 to 50% N-vinyl carbazole (see Division C3) and then dried. The composition may contain dyes or pigments. Specified colouring materials are azopigments and lakes, phthalocyanine pigments, vat dyestuffs carbon black, iron oxides, chrome yellows, titanium dioxide and lithopone, white powdered or flaked metals such as aluminium, bronze, brass, chromiun and gold may be included. The preferred copolymers contain also 1 to 10% of other functional monomers including thermosetting types and generally do not contain more than 25% of the carbazole. The composition may be applied from aqueous dispersion or from solution in an organic solvent. The applied composition may be dried with or without ageing and heating at 200 to 750 DEG F. In Examples 1 (a) an aqueous dispersion of a copolymer of 10 parts of N-vinyl carbazole 88 parts ethyl acrylate 2 parts itaconic acid to which was later introduced 13 parts methyl methacrylate is sprayed on an automotive upholstery leather as a top coat and dried at 140 DEG F. to a permanent flexible non-yellowing finish (b) a piece of side leather coated with a base coat of a polymer of an acrylic ester as sprayed with a mixture of water ammonium chloride, dimethoxy methylpolymethylolmelamine and the polymeric dispersion of 1(a), dried at 80 DEG F. for 3 hours and smooth-plated at 150 DEG F. for 3 seconds to give a leather which withstands wet cracking, water spotting and has good flexing properties (3)chipboard, kraft paper and wall paper are roller-coated with an aqueous dispersion mixture of 10 parts of a copolymer of 45 parts N-vinyl carbazole, 53 parts ethyl acrylate and 2 parts methacrylamide with 40 parts of the copolymer of 12 parts N-vinyl carbazole, 85.5 parts ethyl acrylate, 1.14 parts methacrylamide and 1.30 parts methylolmethacrylamide and dried at 210 DEG F. (4) A solution of 10 parts of a resin forming dimethoxymethylpolymethylolmelamine condensate, 20 parts of diethylphthalate and 1.7 parts triethylamine are added to an aqueous dispersion of an emulsion copolymer of 45 parts of N-vinylcarbazole, 53 parts ethylacrylate and 2 parts of methacrylamide and the mixture diluted with 100 parts of water and sprayed on to an asbestos-cement-sheet so that 2 to 3 grains of resin solids per square foot are applied. The sheet is then dried at 130 DEG C. for 5 minutes. A second series of asbestos sheets are sprayed with a mixture composed of 40 parts of the polymer dispersion of a copolymer of 12 parts of N-vinyl carbazole 85.5 parts ethylacrylate, 1.14 parts methacrylamide and 1.36 parts methylol methacrylamide in 200 parts water, 10 parts of the polymer dispersion of an emulsion copolymer of 45 parts N-vinyl carbazole, 53 parts, ethylacrylate, 2 parts methacrylamide and 10 parts water. One and a half to two and a half grams of solids per square foot are applied and the sheets dried for 16 hours at 95 DEG C. Sheets so coated can be stacked to a height of 2 to 3 feed without blocking they repel water and show no effervescence or fading after outdoor exposure (5) 11 parts of an aqueous dispersion of a copolymer of 10 parts N-vinyl carbazole, 88 parts ethyl acrylate and 12 parts itaconic acid, 2.5 parts of a copper phthalocyanine flue pigment, 5 parts of a 1% aqueous solution of toctylphenoxy polyethoxy ethonol, 15 parts sodium alginate and water form a dyeing composition through which is padded with one dip and one nip a sample of 80 x 80 cotton percale which is then framed, dried, and heated. It retained its colour on washing (6) an aqueous composition of 10 parts of N-vinyl carbazole, 88 parts ethylacrylate and 2 parts itaconic acid is diluted with 300 parts water and sprayed on a non-woven textile fabric formed of three super-imposed carded webs of cotton fibres and the sprayed fabric dried for 10 minutes at 140 DEG C. A permanent, flexible, non-yellowing product resistant to u-v light and to laundering is produced. (7) Cotton sheeting is passed through a pigment dispersion of an aqueous dispersion of a copolymer of 10.5 parts N-vinyl carbazole 75 parts ethylacrylate 12 parts 2-ethyl hexyl acrylate and 2.5 parts itaconic acid together with copper phthalocyanine pigment and additives, then through the nip of a pair of rollers, supported in a frame and dried, to give a soft flexible washing-and laundering-resistant, cracking resistant and u-v-resistant product. A similar procedure is carried out using a copolymer of 15% N-vinyl carbazole, 5% N-methylol-methacrylamide and 80% methyl acrylate, giving a product of similar properties (9) Example (1) is repeated replacing in (a) 30 parts ethyl by 30 parts methylacrylate and in (b) the melamine condensate by 4 parts of a polyepoxide. Specifications 518,057 and 579,698 are referred to.
GB2655360A 1959-08-03 1960-07-29 Copolymers and coating compositions thereof Expired GB959775A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US83106459A 1959-08-03 1959-08-03

Publications (1)

Publication Number Publication Date
GB959775A true GB959775A (en) 1964-06-03

Family

ID=25258211

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2655360A Expired GB959775A (en) 1959-08-03 1960-07-29 Copolymers and coating compositions thereof

Country Status (1)

Country Link
GB (1) GB959775A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6605318B2 (en) * 2001-09-24 2003-08-12 Rohm And Haas Company Method for providing a polymeric composition
WO2009058513A1 (en) 2007-10-30 2009-05-07 3M Innovative Properties Company High refractive index adhesives
CN105462368A (en) * 2014-09-30 2016-04-06 陶氏环球技术有限责任公司 Aqueous dispersion of composite particles
CN105951443A (en) * 2016-06-01 2016-09-21 欣龙控股(集团)股份有限公司 Washing resistance finishing liquid and method for producing washing resistance wood pulp composite spunlace through same
CN110786214A (en) * 2018-08-03 2020-02-14 中国水稻研究所 Carbon black effervescent granule, preparation method thereof and rice ecological cultivation method
CN111944186A (en) * 2020-08-28 2020-11-17 新乡亿博环保科技有限公司 Durable anti-aging rural septic tank and preparation method thereof
CN114801402A (en) * 2022-02-14 2022-07-29 宁波东方席业有限公司 Weather-proof, moisture-proof and fireproof multifunctional mat and preparation method thereof

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6605318B2 (en) * 2001-09-24 2003-08-12 Rohm And Haas Company Method for providing a polymeric composition
WO2009058513A1 (en) 2007-10-30 2009-05-07 3M Innovative Properties Company High refractive index adhesives
US20100222496A1 (en) * 2007-10-30 2010-09-02 Determan Michael D High refractive index adhesives
JP2011502202A (en) * 2007-10-30 2011-01-20 スリーエム イノベイティブ プロパティズ カンパニー High refractive index adhesive
US8309650B2 (en) 2007-10-30 2012-11-13 3M Innovative Properties Company High refractive index adhesives
KR101545365B1 (en) * 2007-10-30 2015-08-18 쓰리엠 이노베이티브 프로퍼티즈 컴파니 High refractive index adhesives
CN105462368A (en) * 2014-09-30 2016-04-06 陶氏环球技术有限责任公司 Aqueous dispersion of composite particles
CN105462368B (en) * 2014-09-30 2021-04-13 陶氏环球技术有限责任公司 Aqueous dispersion of composite particles
CN105951443A (en) * 2016-06-01 2016-09-21 欣龙控股(集团)股份有限公司 Washing resistance finishing liquid and method for producing washing resistance wood pulp composite spunlace through same
CN110786214A (en) * 2018-08-03 2020-02-14 中国水稻研究所 Carbon black effervescent granule, preparation method thereof and rice ecological cultivation method
CN111944186A (en) * 2020-08-28 2020-11-17 新乡亿博环保科技有限公司 Durable anti-aging rural septic tank and preparation method thereof
CN114801402A (en) * 2022-02-14 2022-07-29 宁波东方席业有限公司 Weather-proof, moisture-proof and fireproof multifunctional mat and preparation method thereof
CN114801402B (en) * 2022-02-14 2024-02-09 宁波东方席业有限公司 Weather-proof, dampproof and fireproof multifunctional mat and preparation method thereof

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