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(12) United States Patent (10) Patent No.: US 7.442,731 B2 Tittmann (45) Date of Patent: Oct

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(12) United States Patent (10) Patent No.: US 7.442,731 B2 Tittmann (45) Date of Patent: Oct USOO7442731B2 (12) United States Patent (10) Patent No.: US 7.442,731 B2 Tittmann (45) Date of Patent: Oct. 28, 2008 (54) OPAQUE, COLOUR-PIGMENTED COATING (56) References Cited (75) Inventor: Rolf Tittmann, Kandern (DE) U.S. PATENT DOCUMENTS 4.415,685 A 1 1/1983 Iqbal et al. .................... 524.92 (73) Assignee: Ciba Specialty Chemicals Corp., 5,200,528 A 4/1993 Wooden et al. ....... ... 548/453 Tarrytown, NY (US) 5,476,949 A 12/1995 Wallguist et al. ...... ... 548/453 5.492.564 A 2f1996 Wooden et al. ....... ... 106,493 (*) Notice: Subject to any disclaimer, the term of this 5,618,343 A 4/1997 Hendi et al. ...... ... 106,498 patent is extended or adjusted under 35 5,821,373 A 10/1998 Hao et al. ................... 548/453 U.S.C. 154(b) by 578 days. 5.997,627 A 12/1999 Balbler ........................ 106,493 (21) Appl. No.: 10/529,408 FOREIGN PATENT DOCUMENTS (22) PCT Filed: Sep. 30, 2003 EP O43O875 6, 1991 (86). PCT No.: PCT/EPO3/10835 EP O719842 T 1996 EP O842989 5, 1998 S371 (c)(1), (2), (4) Date: Mar. 29, 2005 Primary Examiner Kriellion A Sanders (74) Attorney, Agent, or Firm Joseph Suhadolnik (87) PCT Pub. No.: WO2004/031280 (57) ABSTRACT PCT Pub. Date: Apr. 15, 2004 (65) Prior Publication Data The invention relates to a coating having a thickness of from 5 to 25 um, comprising a high-molecular-weight organic US 2006/OO41037A1 Feb. 23, 2006 material and from 5 to 9 g/m colored pigments, wherein, based on the total amount of colored pigments, (a) from 30 to (30) Foreign Application Priority Data 90% by weight of 3,6-di(4'-biphenyl)-2,5-dihydro-pyrrolo3. Oct. 7, 2002 (CH) ..................................... 1668/02 4-c-pyrrole-1,4-dione having a specific Surface area of from 20 to 50 m/g and (b) from 10 to 70% by weight of a further (51) Int. Cl. organic colored pigment, selected from the series consisting CSK 5/34 (2006.01) of quinacridone, diketo-pyrrolo3.4-c-pyrrole, dioxazine, (52) U.S. Cl. ........................... 524/88: 524/99: 428/.457; indanthrone, perylene, phthalocyanine and 3-amino-1H 428/704 isoindol-1-one-oximatometal complex pigments and solid (58) Field of Classification Search ................... 524/88, Solutions and mixtures thereof, are present. 524/99: 428/457, 704 See application file for complete search history. 20 Claims, No Drawings US 7,442,731 B2 1. 2 OPAQUE, COLOUR-PIGMENTED COATING The further quinacridone, diketo-pyrrolo3.4-c-pyrrole, dioxazine, indanthrone, perylene, phthalocyanine and Coloured finishes, especially red finishes, for example in 3-amino-1H-isoindol-1-one-oximato-metal complex pig the automobile industry, are applied in layers having a dry ments (b) are, for example, Pigment Blue 15:1, Pigment Blue film thickness of from 35 to 40 um. Although thinner layers 15:2, Pigment Blue 15:3, Pigment Blue 15:4, Pigment Blue would in principle be desirable for economic reasons, this is 15:6, Pigment Blue 16, Pigment Blue 60, Pigment Blue 64, not possible since thin layers having at the same time tincto Pigment Green 7, Pigment Green 36, Pigment Green 37, rially strong, attractive coloristic properties, adequate cover Pigment Red 122, Pigment Red 123, Pigment Red 149, Pig ing power and good Surface-coating characteristics cannot be ment Red 178, Pigment Red 179, Pigment Red 190, Pigment Successfully produced. If, for example, attempts are made to 10 Red 202, Pigment Red 224, Pigment Red 254, Pigment Red reduce the layer thickness while using the same amount of 255, Pigment Red 257, Pigment Red 270, Pigment Red 272, pigment per unit of area, these fail because of the rheology of Pigment Violet 19, Pigment Violet 23, Pigment Violet 29 or the Surface coating, which results in unsatisfactory gloss. Pigment Violet 37, preferably quinacridone, diketo-pyrrolo The object of the invention was to provide a coloured finish 3,4-c-pyrrole, dioxazine, indanthrone or perylene pig that can be used in thin layers and that satisfies high require 15 ments, especially Pigment Violet 19, Pigment Red 202 or ments. Surprisingly, this has successfully been achieved by Pigment Red 254. These further organic coloured pigments the use of a combination of various pigments in a narrow, low are preferably those having a specific surface area of from 10 concentration range. to 40 m/g, in the case of quinacridone or diketo-pyrrolo[3. U.S. Pat. No. 5,476,949 discloses finely dispersed diketo 4-c-pyrrole pigments especially from 10 to 25 m/g and, in pyrrolopyrrole pigments, among them 3,6-di(4'-biphenyl)-2, the case of dioxazine, indanthrone or perylene pigments, 5-dihydro-pyrrolo3.4-c-pyrrole-1,4-dione having a colour especially from 20 to 40 m/g. saturation C* of 15.8 in 1% concentration in a 1 mm thick Component (b) of the coloured pigment may, where appro PVC injection moulding. The Stokes equivalent diameter Ds priate, consist of a mixture or a solid solution of several (for is <0.21 Jum, and the D value is 0.11 Lum. That pigment has example from 2 to 5) coloured pigments (b). In the coloured outstanding transparency. 25 pigment mixture, in addition to the two components (a) and U.S. Pat. No. 5.492,564 discloses 3,6-di(4'-biphenyl)-2,5- (b), any desired further coloured pigments may also be dihydro-pyrrolo3.4-c-pyrrole-1,4-dione having a high cov present as additional components, preferably inorganic pig ering power and an extraordinarily high colour Saturation C* ments, such as, for example, yellow or red iron oxides, of 245 in 1% concentration in a 1 mm thick PVC injection molybdate orange or lead chromates, especially Pigment Red moulding produced according to DIN 53775/Part 2. Accord 30 101. If there are doubts as to whether a substance is a coloured ing to Examples 4 and 5, that colour Saturation is also pigment, a 35 um thick film is produced on a roll mill from obtained in an acrylic varnish comprising 16.4% by weight 0.5% by weight of that substance, 0.5% by weight oftitanium pigment. Other coloured pigments are not mentioned, how oxide white (Pigment White 6) and 99% by weight of stabi ever, and nor is the layer thickness. lised soft PVC, and the reflecting colour of the film is mea State of the art in high-quality red finishes are those based 35 Sured. Under d/8 geometry with the specular component on opaque Colour Index Pigment Red 254 (Irgazinr DPP included, Des light and a measuring angle of 10, coloured Red BO or BOX, Ciba Spezialitätenchemie AG), in combi pigments have a colour saturation C* of at least 5 in the CIE nation with high-transparency pigments such as, for example, 1976 L*C*h colour co-ordinate system. Pigment Red 177 (Cromophtal(R) Red A2B, Ciba Spezialitä It is also possible to use, in addition, other colour-influenc tenchemie AG). The properties of such finishes leave some 40 ing constituents, such as white pigments, black pigments or thing to be desired, however, when they are applied in layers effect pigments. Those pigments must not, however, be having a dry film thickness of approximately 30 um or less. included in the amount of the coloured pigment, even if they The invention relates to a coating having a thickness of are used in the form of a mixture with a coloured pigment. from 5 to 25 um, comprising a high-molecular-weight The high-molecular-weight organic material may be of 45 natural or synthetic origin and usually has a molecular weight organic material and from 5 to 9 g/m coloured pigments, in the range from 10 to 10 g/mol. It may, for example, be a wherein, based on the total amount of coloured pigments, natural resin or a drying oil, rubber or casein, or a modified (a) from 30 to 90% by weight of 3,6-di(4'-biphenyl)-2,5- natural Substance. Such as chlorinated rubber, an oil-modified dihydro-pyrrolo3.4-c-pyrrole-1,4-dione having a spe alkyd resin, viscose, a cellulose ether or ester, such as cellu cific surface area of from 20 to 50 m/g and 50 lose acetate, cellulose propionate, cellulose acetobuty-rate or (b) from 10 to 70% by weight of a further organic coloured nitrocellulose, but especially a totally synthetic organic poly pigment, selected from the series consisting of quinac mer (a thermo-setting plastic or a thermoplastic), as is ridone, diketo-pyrrolo3.4-c-pyrrole, dioxazine, indan obtained by polymerisation, polycondensation or polyaddi throne, perylene, phthalocyanine and 3-amino-1H tion, for example a polyolefin, Such as polyethylene, polypro isoindol-1-one-oximato-metal complex pigments and 55 pylene or polyisobutylene, a Substituted polyolefin, Such as a Solid solutions and mixtures thereof, are present. polymerisation product of vinyl chloride, vinyl acetate, Sty The coating preferably contains in total from 6 to 8 g/m rene, acrylonitrile, an acrylic and/or methacrylic acid ester or coloured pigments. It is also preferred for the thickness of the butadiene, and also a copolymerisation product of the said coating to be approximately from 15 to 25um. monomers, especially ABS or EVA. 3,6-DiG4'-biphenyl)-2,5-dihydro-pyrrolo3.4-c-pyrrole 60 From the series of the polyaddition resins and polyconden 1,4-dione, known as Pigment Red 264, preferably constitutes sation resins there may be mentioned condensation products from 40 to 80% by weight of the coloured pigment mixture.
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