Methods for synthesis of liquid crystals
AssigneeSouthwest Research Institute
InventorsStephen T. Wellinghoff, Douglas P. Hanson
Life of this patent
Estimating the term…
Abstract
A method for producing platform molecules comprising: forming a mixture comprising first and second phenylene rings comprising halogenated carboxylic groups, and a third phenylene ring comprising a desired substituent and a first functionality at a para-position to a second funcitonality; and exposing the mixture to conditions effective to react the first halogenated carboxylic group with the first functionality to produce a first ester bond, and the second halogenated carboxylic group with the second functionality to produce a second ester bond; producing platform molecules comprising terminal groups comprising the first functional group at a position para to first ester bond and the second functional group at a position para to the second ester bond.
Claims51
A method for producing platform molecules comprising:
- providing a first phenylene ring consisting essentially of a first functional group at a para-position to a first halogenated carboxylic group;
- providing a second phenylene ring consisting essentially of a second functional group at a para-position to a second halogenated carboxylic group;
- providing a third phenylene ring comprising a desired substituent and comprising a first functionality at a para-position to a second functionality;
- and
- forming a mixture comprising said first phenylene rings, said second phenylene rings, and said third phenylene rings;
- exposing said mixture to conditions effective to react said first halogenated carboxylic group with said first functionality to produce a first ester bond, said conditions being effective to react said second halogenated carboxylic group with said second functionality to produce a second ester bond, producing platform molecules comprising terminal groups comprising said first functional group at position para- to said first ester bond and said second functional group at a position para- to said second ester bond, said terminal groups comprising other than polymerizable groups, one or more of said terminal groups being selected from the group consisting of H—(CH2)n—O— groups, Cl(CH2)n—O— groups, Br(CH2)n—O— groups, I(CH2)n—O—, and reactive derivatives thereof, wherein n is from about 2 to about 12 and CH2 independently is selected from the group consisting of CH2 which is unsubstituted and CH2 which is substituted by an element selected from the group consisting of oxygen, sulfur, and an ester group;
- provided that at least 2 carbon atoms separate said oxygen or said ester group;
- and,
- wherein, when both of said terminal groups comprise polymerizable groups, said desired substituent provides sufficient steric hindrance to achieve a nematic state at room temperature while suppressing crystallinity at room temperature.
A method for producing platform molecules comprising:
- reacting 4-nitrobenzoic acid with a 1, n-dihydroxyalkane comprising an alkylene group having from about 2 to about 12 carbon atoms in the presence of an esterification catalyst under esterification conditions effective to produce a hydroxyalkyl ester of 4-nitrobenzoic acid;
- treating the hydroxyalkyl ester of 4-nitrobenzoic acid under cleaving conditions effective to produce 4-(n-hydroxyalkoxy)benzoic acid, comprising a nitrobenzoic carboxyl group wherein n is the number of carbon atoms in said alkylene group;
- converting said nitrobenzoic carboxyl group to a halogenated nitrobenzoic carboxyl group;
- providing said 4-(n-hydroxyalkoxy)benzoic acid, comprising said halogenated nitrobenzoic carboxyl group as one or more of a phenylene ring selected from the group consisting of a first phenylene ring comprising a first halogenated carboxylic group and a second phenylene ring comprising a second halogenated carboxylic group;
- providing a third phenylene ring comprising a desired substituent and comprising a first functionality at a para-position to a second functionality;
- reacting said first halogenated carboxylic group with said first functionality, producing a first ester bond;
- and
- reacting said second halogenated carboxylic group with said second functionality, producing a second ester bond, thereby producing platform molecules comprising a first hydroxyalkoxy group at position para- to said first ester bond and a second hydroxyalkoxy group at a position para- to said second ester bond,
- wherein, when both said first hydroxyalkoxy group and said second hydroxyalkoxy group comprise polymerizable groups, said desired substituent provides sufficient steric hindrance to achieve a nematic state at room temperature while suppressing crystallinity at room temperature.
A method for producing platform molecules comprising:
- providing a first phenylene ring comprising a first functional group at a para-position to a first halogenated carboxylic group;
- providing a second phenylene ring comprising a second functional group at a para-position to a second halogenated carboxylic group;
- providing a third phenylene ring comprising a desired substituent and comprising a first functionality at a para-position to a second functionality;
- and
- reacting said first functionality with said first halogenated carboxylic group, producing a first ester bond between said third phenylene ring and said first phenylene ring;
- and
- reacting said second functionality with said second halogenated carboxylic group, producing a second ester bond, producing platform molecules comprising said first functional group at position para- to said first ester bond and said second functional group at a position para- to said second ester bond;
- and
- forming an elongation mixture comprising one or more additional phenylene rings comprising additional functional groups other than polymerizable groups at para-position(s) to additional carboxylic group(s) selected from the group consisting of carboxyl groups and reactive derivatives of carboxyl groups;
- and
- exposing said elongation mixture to conditions effective to react said additional halogenated carboxylic group(s) with one or more functional group selected from the group consisting of said second functional group and said third functional group to produce elongated platform molecules comprising additional phenylene rings comprising said additional functional group(s) at a position para- to additional ester bond(s), said elongated platform molecules comprising terminal groups other than polymerizable groups, one or more of said terminal groups being selected from the group consisting of H—(CH2)n—O— groups, Cl(CH2)n—O— groups, Br(CH2)n—O— groups, I(CH2)n—O—, and reactive derivatives thereof, wherein n is from about 2 to about 12 and CH2 independently is selected from the group consisting of CH2 which is unsubstituted and CH2 which is substituted by an element selected from the group consisting of oxygen, sulfur, and an ester group;
- provided that at least 2 carbon atoms separate said oxygen or said ester group;
- wherein, when both said first functional group and said second functional group comprise polymerizable groups, said desired substituent provides sufficient steric hindrance for said platform molecules to achieve a nematic state at room temperature while suppressing crystallinity at room temperature.
Dependencies are inferred from the claim text.