Chiral dopant and identification and authentication using polymeric liquid crystal material markings

Patent metadata

Field	Value
Publication number	US-2016264591-A1
Application number	US-201415030668-A
Country	US
Kind code	A1
Filing date	Oct 20, 2014
Priority date	Oct 21, 2013
Publication date	Sep 15, 2016
Grant date	—

Abstract

Disclosed are chiral dopants of general formula (I) below as well as uses thereof involving chiral liquid crystal polymers and markings comprising these polymers: wherein R 1 , R 2 , R 3 , R 4 , A 1 and A 2 , m, n, o and p are as defined in the claims.

First claim

1 . Chiral dopant of general formula (I):

wherein
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 each independently denote C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
A 1 and A 2 each independently denote a group:
(i) —[(CH 2 )y-O]z-C(O)—CH═CH 2 ;
(ii)—C(O)-D 1 -O—[(CH 2 )y-O]z-C(O)—CH═CH 2 ;
(iii) —C(O)-D 2 -O—[(CH 2 )y-O]z-C(O)—CH═CH 2 ;

D 1 denotes a group

D 2 denotes a group

m, n, o, p, q, r, s, and t each independently denote 0, 1 or 2;
y denotes 0, 1, 2, 3, 4, 5 or 6;
z equals 0 if y equals 0 and z equals 1 if y equals 1 to 6.

2 . Chiral dopant according to claim 1 , having general formula (IA):

wherein
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 each independently denote C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
A 1 and A 2 each independently denote a group:
(i) —[(CH 2 )y-O]z-C(O)—CH═CH 2 ;
(ii) —C(O)-D 1 -O—[(CH 2 )y-O]z-C(O)—CH═CH 2 ;
(iii) —C(O)-D 2 -O—[(CH 2 )y-O]z-C(O)—CH═CH 2 ;

D 1 denotes a group

D 2 denotes a group

m, n, o, p, q, r, s, and t each independently denote 0, 1 or 2;
y denotes 0, 1, 2, 3, 4, 5 or 6;
z equals 0 if y equals 0 and z equals 1 if y equals 1 to 6.

3 . Chiral dopant according to claim 1 , having general formula (IB):

wherein
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 each independently denote C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
A 1 and A 2 each independently denote a group:
(i) —[(CH 2 )y-O]z-C(O)—CH═CH 2 ;
(ii) —C(O)-D 1 -O—[(CH 2 )y-O]z-C(O)—CH═CH 2 ;
(i) —C(O)-D 2 -O—[(CH 2 )y-O]z-C(O)—CH═CH 2 ;

D 1 denotes a group

D 2 denotes a group

m, n, o, p, q, r, s, and t each independently denote 0, 1 or 2;
y denotes 0, 1, 2, 3, 4, 5 or 6;
z equals 0 if y equals 0 and z equals 1 if y equals 1 to 6.

4 . Chiral dopant according to claim 1 , having general formula (IC):

wherein
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 each independently denote C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
A 1 and A 2 each independently denote a group:
(i) —[(CH 2 )y-O]z-C(O)—CH═CH 2 ;
(ii) —C(O)-D 1 -O—[(CH 2 )y-O]z-C(O)—CH═CH 2 ;
(iii) —C(O)-D 2 -O—[(CH 2 )y-O]z-C(O)—CH═CH 2 ;

D 1 denotes a group

D 2 denotes a group

m, n, o, p, q, r, s, and t denote each independently 0, 1 or 2;
y denotes 0, 1, 2, 3, 4, 5 or 6;
z equals 0 if y equals 0 and z equals 1 if y equals 1 to 6.

5 . Chiral dopant according to claim 1 , having general formula (ID):

wherein
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 each independently denote C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
A 1 and A 2 each independently denote a group:
(i) —[(CH 2 )y-O]z-C(O)—CH═CH 2 ;
(ii) —C(O)-D 1 -O—[(CH 2 )y-O]z-C(O)—CH═CH 2 ;
(iii) —C(O)-D 2 -O—[(CH 2 )y-O]z-C(O)—CH═CH 2 ;

D 1 denotes a group

D 2 denotes a group

m, n, o, p, q, r, s, and t each independently denote 0, 1 or 2;
y denotes 0, 1, 2, 3, 4, 5 or 6;
z equals 0 if y equals 0 and z equals 1 if y equals 1 to 6.

6 . Chiral dopant according to claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 each independently denote C 1 -C 6 alkyl.

7 . Chiral dopant according to claim 1 , wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 each independently denote C 1 -C 6 alkoxy.

8 . Chiral dopant according to claim 1 , wherein A 1 and A 2 each independently denote —[(CH 2 )y-O]z-C(O)—CH═CH 2 ; R 1 , R 2 , R 3 and R 4 each independently denote C 1 -C 6 alkyl or C 1 -C 6 alkoxy; and m, n, o, and p each independently denote 0, 1, or 2.

9 . Chiral dopant according to claim 1 , wherein A 1 and A 2 each independently denote —C(O)-D 1 -O—[(CH 2 )y-O]z-C(O)—CH═CH 2 and/or —C(O)-D 2 -O—[(CH 2 )y-O]z-C(O)—CH═CH 2 ; and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , each independently denote C 1 -C 6 alkyl or C 1 -C 6 alkoxy.

10 . Chiral dopant according to claim 1 , wherein the alkyl or alkoxy groups of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 each independently comprise 1, 2, 3, 4, 5 or 6 carbon atoms.

11 . Chiral liquid crystal precursor composition comprising at least one or more chiral dopants according to claim 1 .

12 . Chiral liquid crystal precursor composition according to claim 11 , wherein the composition comprises in addition one or more nematic components.

13 . Chiral liquid crystal precursor composition according to claim 11 containing a security materials selected from inorganic luminescent compounds, organic luminescent compounds, IR-absorbers, magnetic materials, forensic markers, and combinations thereof.

14 . Marking for an item or article, wherein said marking comprises chiral polymeric liquid crystal material wherein the polymer of the chiral polymeric liquid crystal material comprises units derived from one or more chiral dopants according to claim 1 .

15 . Item or article carrying at least one marking according to claim 14 .

16 . Use of a marking according to claim 14 for tracking or tracing an item or article.

17 . Intermediate in the liquid crystal state, obtainable by independently applying a liquid crystal precursor composition comprising a chiral dopant according to claim 1 to a substrate by a variable information printing process or a conventional printing process and applying heat to both evaporate the solvent contained in the liquid crystal precursor composition and promote the liquid crystal state.

18 . An ink, coating or flake comprising one or more nematic compounds and one or more chiral dopants according to claim 1 .

Assignees

• Sicpa Holding Sa

Inventors

• Urbaneja Xavier
• Wyss Patrick
• Mayade Sabine
• Jauzein Tristan

Classifications

• C07D493/04 Primary

  Ortho-condensed systems · CPC title

• G07D7/122

  Physics · mapped topic

• C09D11/03

  characterised by features other than the chemical nature of the binder · CPC title

• C09K19/588

  Heterocyclic compounds · CPC title

• C09D11/107

  from unsaturated acids or derivatives thereof · CPC title