Cholesteric flakes
AssigneeMerck Patent GmbH
InventorsDavid Coates, Mark Goulding, Alison May
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Abstract
The invention relates to cholesteric polymer flakes obtainable from a chiral polymerizable mesogenic material, to methods of manufacturing such cholesteric flakes, to the use of certain chiral and achiral polymerizable compounds with one or more terminal polymerizable groups for the manufacturing of such flakes and to the use of such cholesteric flakes as effect pigments in spraying or printing inks or paints or colored plastics for different applications, especially for automotive use, cosmetic products and security applications.
Claims39
A flake product of a cholesteric crosslinked polymer, prepared by a process comprising:
- (a) coating a chiral polymerizable mesogenic material onto a substrate which is then optionally covered by a second substrate,
- (b) aligning the coating material into a planar orientation,
- (c) curing the aligned coating material into a crosslinked polymer film,
- (d) removing the crosslinked polymer film from the substrate, and
- (e) grinding it, optionally while cooling,
- wherein the chiral polymerizable mesogenic material comprises at least two different polymerizable mesogenic compounds each having at least one terminal polymerizable group that is linked, optionally via a spacer group, to a mesogenic core wherein the polymerizable group is selected from the following formulae:
- CH2═CW—COO— I1
- WCH═CH—O— I2
- CH2═CH—Ph—(O)n—I3
- in which W denotes H, CH3 or Cl and n is 0 or 1.
A flake product of a cholesteric crosslinked polymer, prepared by a process comprising:
- (a) coating a chiral polymerizable mesogenic material onto a substrate which is then optionally covered by a second substrate,
- (b) aligning the coating material into a planar orientation,
- (c) curing the aligned coating material into a crosslinked polymer film,
- (d) removing the crosslinked polymer film from the substrate, and
- (e) grinding it, optionally while cooling,
- wherein the chiral polymerizable mesogenic material comprises at least one achiral polymerizable mesogenic compound and at least one chiral polymerizable mesogenic compound wherein at least one of these compounds exhibits two or more polymerizable groups.
A flake product of a cholesteric crosslinked polymer, prepared by a process comprising:
- (a) coating a chiral polymerizable mesogenic material onto a substrate which is then optionally covered by a second substrate,
- (b) aligning the coating material into a planar orientation,
- (c) curing the aligned coating material into a crosslinked polymer film,
- (d) removing the crosslinked polymer film from the substrate, and
- (e) grinding it, optionally while cooling,
- wherein at least one polymerizable mesogenic compound is a fumarate.
A flake product of a cholesteric crosslinked polymer, prepared by a process comprising:
- (a) coating a chiral polymerizable mesogenic material onto a substrate which is then optionally covered by a second substrate,
- (b) aligning the coating material into a planar orientation,
- (c) curing the aligned coating material into a crosslinked polymer film,
- (d) removing the crosslinked polymer film from the substrate, and
- (e) grinding it, optionally while cooling,
- wherein the chiral polymerizable mesogenic material comprises a non mesogenic compound with one or more polymerizable groups.
A flake product of a cholesteric crosslinked polymer containing a polymerized mesogenic compound of the formula II:
- P—(Sp)n—MG—R II
- wherein
- P is a polymerizable group selected from formulae I1 to I4,
- Sp is a spacer group having I to 20 C atoms,
- R is H, halogen or cyano or a chiral or achiral organic group that may be linear or branched or, in compounds exhibiting more that one polymerizable group, has the meaning given for P—(Sp)n—,
- n is 0 or 1, and
- MG is a mesogenic or mesogenity supporting group of formula III
- —(A1—Z1)m—A2—Z2—A3— III
- wherein
- A1, A2 and A3 are independently from each other 1,4-phenylene in which, one or more CH groups are optionally replaced by N, 1,4-cyclohexylene in which, one or two non-adjacent CH2 groups are optionally replaced by O and/or S, 1,4-cyclohexenylene or naphthalene-2,6-diyl, all of which are 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,
- Z1 and Z2 are each independently —COO—, —OCO—, —CH2CH2—, —OCH2—, —CH2O—, —CH═CH—, —C≡C—, —CH═CH—COO—, —OCO—CH═CH— or a single bond and m is 0, 1 or 2.
A method for preparing a flake product of a cholesteric crosslinked polymer which comprises:
- (a) coating a chiral polymerizable mesogenic material onto a substrate which is then optionally covered by a second substrate,
- (b) aligning the coating material into a planar orientation,
- (c) curing the aligned coating material into a crosslinked polymer film,
- (d) removing the crosslinked polymer film from the substrate, and
- (e) grinding it, optionally while cooling,
- wherein the chiral polymerizable mesogenic material comprises at least two different polymerizable mesogenic compounds each having at least one terminal polymerizable group that is linked, optionally via a spacer group, to a mesogenic core wherein the polymerizable group is selected from the following formulae:
- CH2═CW—COO— I1
- WCH═CH—O— I2
- CH2═CH—Ph—(O)n—I3
- in which W denotes H, CH, or Cl and n is 0 or 1.
Dependencies are inferred from the claim text.