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US 6,552,102 B2Granted
Pigment flakes
AssigneeMerck Patent GmbH
InventorsEike Poetsch, Gerhard Pfaff, Matthias Kuntz, Stephan Derow, David Coates
Life of this patent
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Abstract
Described are chiral liquid crystalline polymer materials and polymerizable compounds used for preparing them. The polymer materials can serve as a carrier material or are coated onto a carrier material. Also described are methods of making such materials and using them to make pigment flakes used in paints, printing inks, spray paints, cosmetic products, colored plastics, optical elements and security applications.
Claims23
A polymerizable compound of formula I*
- P—(Sp—X)n—CG—R I*
- wherein
- P is a polymerizable group,
- Sp is a spacer group having 1 to 20 C atoms,
- X is —O—, —S—, —CO—, —COO—, —OCO—, —O—COO—, —SO2—O—, —O—SO2— or a single bond,
- n is 0 or 1, and
- R is H or an alkyl radical with 1 to 25 C atoms which is optionally unsubstituted, mono- to perhalo-substituted by halogen or CN, and, optionally, one or more non-adjacent CH2 groups being replaced, in each case independently from one another, by —O—, —S—, —NH—, —N(CH3)—, —CO—, —COO—, —OCO—, —OCO—O—, —S—CO—, —CO—S— or —C≡C— in such a manner that oxygen atoms are not linked directly to one another, or alternatively R is halogen, cyano or has independently one of the meanings given for P—(Sp—X)n—,
- and
- CG is a chromophoric group or a fluorescent chromophoric group of the following formula
- —(A1—Z1)c—Ch—(Z1—A1)d— III
- wherein
- A1 is 1,4-phenylene in which, optionally, one or more CH groups are replaced by N, 1,4-cyclohexylene in which, optionally, one or two non-adjacent CH2 groups are replaced by O and/or S, 1,4-cyclohexenylene or naphthalene-2, 6-diyl, optionally all of these groups being unsubstituted, mono- or polysubstituted with halogen, cyano or nitro groups or alkyl, alkoxy or alkanoyl groups having 1 to 7 C atoms wherein one or more H atoms may be substituted by F or Cl,
- Z1 is —O—, —CO—, —COO—, —OCO—, —SO2—O—, —O—SO2—, —CH2CH2—, —OCH2—, —CH2O—, —CH=CH—, —C≡C—, —CH=CH—COO—, —OCO—CH=CH— or a single bond, c and d are 0, 1 or 2, and
- Ch is a chromophore or fluorescent chromophore, which can optionally be chiral and/or mesogenic, and is denoted by one of the following groups, optionally all of these groups being unsubstituted, mono- or polysubstituted with halogen, cyano or nitro groups or alkyl, alkoxy or alkanoyl groups having 1 to 7 C atoms wherein one or more H atoms are optionally substituted by F or Cl:
- 5-(p-dimethylaminobenzylidene)-rhodanine,
- a thionine-containing group,
- 1,4-diphenyl-1, 3-butadiene,
- 1,6-diphenyl-1,3,5-hexatriene,
- indigotine,
- indigocarmine,
- an oxazole-containing group,
- an azo dye,
- an anthraquinone-containing group,
- a fluorescein-containing group,
- a 2,5-dihydropyrrolo[3,4-c]pyrrole-1, 4-dione-containing group,
- a perylene-containing group,
- a benzimidazole-containing group,
- a benzoxazole-containing group,
- a stilbene-containing group,
- a polyphenylene-containing group,
- a spiro group-containing polyphenylene-containing group, or
- a dye comprising at least one cholesteryl group, provided that:
- when Ch is an azo dye, an anthraquinone-containing group, a perylene-containing group, or a stilbene-containing group, R is P—(Sp—X)n—.
30 more elements
A polymerizable compound of formula I*
- P—(Sp—X)n—CG—R I*
- wherein
- P is an acrylate or methacrylate polymerizable group,
- Sp is a 1 to 12 carbon atoms alkylene spacer group,
- X is —O—, —S—, —CO—, —COO—, —OCO—, —O—COO—, —SO2—O—, —O—SO2— or a single bond,
- n is 0 or 1,
- R is P—(Sp—X)n—,
- and
- CG is a chromophoric group or a fluorescent chromophoric group of the following formula
- —(A1—Z1)c—Ch—(Z1—A1)d— III
- wherein
- A1 is 1,4-phenylene in which, optionally, one or more CH groups are replaced by N, 1,4-cyclohexylene in which, optionally, one or two non-adjacent CH2 groups are replaced by O and/or S, 1,4-cyclohexenylene or naphthalene-2, 6-diyl, optionally all of these groups being unsubstituted, mono- or polysubstituted with halogen, cyano or nitro groups or alkyl, alkoxy or alkanoyl groups having 1 to 7 C atoms
- wherein one or more H atoms may be substituted by F or Cl,
- Z1 is —O—, —CO—, —COO—, —OCO—, —SO2—O—, —O—SO2—, —CH2CH2—, —OCH2—, —CH2O—, —CH=CH—, —C≡C—, —CH=CH—COO—, —OCO—CH=CH— or a single bond, c and d are 0, 1 or 2, and
- Ch is a chromophore or fluorescent chromophore, which can optionally be chiral and/or mesogenic, and is a 2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione-containing group, which is optionally unsubstituted, mono- or polysubstituted with halogen, cyano or nitro groups or alkyl, alkoxy or alkanoyl groups having 1 to 7 C atoms wherein one or more H atoms is optionally substituted by F or Cl.
12 more elements
Dependencies are inferred from the claim text.