Polymers

Details Polymers Polymers

2000-06-02

2002-08-27

Acquah, Samuel A. (Department: 1711)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

From ketone or ketene reactant

C528S220000, C528S222000, C528S225000

Reexamination Certificate

active

06441124

ABSTRACT:

A preferred product has the general formula III
where, R
1
may be the same as or different to R
1′
, which may be the same as or different to R
2
, which may be the same as or different to R
2′
and is a hydrogen atom or CH
3
, CH
3
CH
2
, —OCH
3
, —OCH
2
CH
3
, —CH
2
OCH
3
, —CH
2
OCH
2
CH
2
OCH
3
, methoxyethoxyethoxymethyl, aryloxymethyl, phenyl, Cl, Br, CN or NO
2
, —CH
2
COOR or —CH
2
NHCOR′″ (where R′″ is C
1
-C
6
alkyl or a phenyl or biphenyl group), or a C
1
-C
5
alkyl group, or an aryl group e.g. a benzyl group, or an —SO
3
H group or a hydroxyl group or a C
1
-C
5
alkoxy group or an H
2
PO
3
group, and R
1
and R
1′
are different to R
2
and R
2′
and n is an integer ranging from 10 to 100.
POLYMERS
The present invention relates to polymerisation products of anthraquinone (AQ) with diamino anthracenes (DAA) and to their production. In particular, the invention relates to homopolymers or co-polymers of anthraquinone with 9,10 diaminoanthracene. The polymerisation products may be polymers or oligomers (e.g. of 2 to 12 or 15 repeat units) and the processes of the present invention enables homopolymers and co-polymers to be made which differ only in the substituents which are attached to the anthracene backbone. The co-polymers can be expected on reduction to produce materials which are electroconductive and fairly soluble in a range of commercially viable and environmentally friendly organic solvents. They may also be sufficiently transparent to be used in thin film applications where they may be used as transparent coatings, used extensively in displays, e.g. electroluminescent and liquid crystal displays and to some extent in electromagnetic shielding windows. The copolymers disclosed herein can be used in antistatic applications.
Polymers of aniline and applications thereof have been known for many years. Poly (1-aminoanthracene) (P1-AA hereafter) has also been described recently (Takakazu Yamamoto et al.,
Macromolecules
, 1993, 26, pages 6992-6997). These polymers have similar structures to poly(aniline) and are dark coloured, varying from bluish-black, brown to brown-black powders. Yamamoto states P1-AA has conductivity of the order of 1×10
−4
S cm
−1
. P1-AA is stated by Yamamoto to be soluble in organic solvents such as HCOOH, DMF, DMSO and NMP, slightly soluble in CHCl
3
and THF, and insoluble in CH
3
OH, C
2
H
5
OH, CH
3
CN, benzene and toluene. Yamamoto gives no indication of the transparency of P1-AA. The applicants are also aware of two articles namely A. Everaerts et al.,
Polym. Prepr
. (Am. Chem. Soc., Div. Polym. Chem.) 24 (7) pp 1703-16 (1986)(hereafter Everaerts) and P. A. Williams et al,
Macromolecules
26 (21) pp5820-1 (1993) (hereafter Williams)
The present inventors have been seeking to develop a conductive polymer of sufficient transparency to enable it to be used where light transmission as well as conductivity is required, and in addition solubility which would facilitate fabrication into useful structures, such as films, by solvent methods. In contrast to P1-AA we have discovered surprisingly that certain polymerisation products of anthraquinone with 9,10 diaminoanthracene are sufficiently transparent and soluble electroconductive polymers.
These products may exhibit a particular advantage over the transparent Indium Tin Oxide (ITO) films currently employed in transparent coatings. The ITO coatings lose most or all of their electroconductivity if the surface is bent. However, the products according to the present invention can be expected to maintain their electroconductivity even when bent.
In addition the present inventors wished to devise a procedure by which polymers could be provided in which the polymer backbone was constant and maximum flexibility was provided for varying the substitution on the backbone.
According to one aspect of the present invention, there is provided a polymeric or oligomeric product obtainable from the reaction of an anthraquinone with an aromatic diamine, characterised in that the anthraquinone is substituted or is not substituted and in that the diamine is a diamino anthracene which is substituted or is not substituted. These are preferably produced by polycondensation.
The substitution may be such that the product is a homopolymer or homo-oligomer, or the substitution may be such that the product is a co-polymer or a co-oligomer.
The diaminoanthracene is preferably a 9,10-diaminoanthracene, which may be substituted or not.
The DAA may be substituted with a single substituent e.g. a C
1
-C
5
alkyl, an aryl e.g. a benzyl group, an —SO
3
H, or —OH, or C
1
-C
5
alkoxy, or aryloxy, e.g. phenoxy or substituted phenoxy or biphenyloxy group or an H
2
PO
3
group or with more than one substituent.
The invention also extends to products in which the anthraquinone is replaced wholly or in part by one or more substituted anthraquinones. Commercially available substituted anthraquinones include:
1-methylaminoanthraquinone;
2-aminoanthraquinone;
1-aminoanthraquinone;
9,10-Anthraquinone-2-sulphonic acid sodium salt;
9,10-Anthraquinone-1,5-disulphonic acid disodium salt;
1-chloroanthraquinone
2-Methylanthraquinone;
2-Ethylanthraquinone;
9,10-Anthraquinone-2,6-disulphonic acid disodiun salt;
2-(Hydroxymethyl)anthraquinone;
Anthraquinone-2-carboxylic acid, (contains 98% 9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic acid)
1,5 dihydroxyanthraquinone;
1,4 dihydroxyanthraquinone;
1,4-Bis(methylamino)anthraquinone;
Benz[a]anthracene-7,12-dione;
1,4-Diaminoanthraquinone;
1,5-Dichloroanthraquinone;
1,5-Dinitro-9,10-anthraquinone;
2,3,6,7-Tetramethyl-anthraquinone;
1-Hydroxy-4-(paratoluidine)anthraquinone;
1-Alkyloxy-3-methoxymethoxy-anthraquinone;
2,6-Di-tert-butyl-anthraquinone;
1-Amino-2-bromo-4-p-tolylamino-anthraquinone;
1-Hydroxy-2-pent-2-enyl-anthraquinone;
1-Amino-4-hydroxy-anthraquinone;
2-[(2-Amino-ethylamino)-methyl]-anthraquinone, dihydrobromide;
1,4-Dimethyl-anthraquinone;
1,4-Diamino-2,3-bis-phenoxy-anthraquinone;
2,7-Dimethyl-anthraquinone;
1,2-Dimethyl-anthraquinone;
1-Iodo-2-methyl-anthraquinone;
The ratio of anthraquinone to aromatic diamine is in the range preferably of 5:1 to 1:5, eg. in the range 3:1 to 1:3, more preferably in the range 2:1 to 1:2, e.g. 1:1. Preferably the anthraquinone is a C
1
-C
6
alkyl anthraquinone or a C
1
-C
10
alkoxy anthraquinone or a hydroxyanthraquinone, for example the anthraquinone may be 2-ethyl anthraquinone or 2-methyl anthraquinone, or 2,3-dimethyl anthraquinone or 2,6-dioctyloxy anthraquinone or 2,6-dihydroxyanthraquinone.
The diaminoanthrance may be substituted in the same way as the anthraquinone and with the same range of substituents.
Preferred substituted anthraquinones are C
1
-C
6
alkyl anthraquinones e.g. 2-ethyl anthraquinone or 2-methyl anthraquinone, or 2,3-dimethyl anthraquinone or C
1
-C
10
alkoxy anthraquinones e.g. 2,6-dioctyloxy anthraquinone or hydroxyanthraquinones e.g. 2,6-dihydroxyanthraquinone.
More broadly, the substituted anthraquinones may be of general formula (1):
where, R may be the same as or different to R′, and may be a hydrogen atom (when R=R′=H, the compound is anthraquinone), or CH
3
, CH
3
CH
2
—, —OCH
3
, —OCH
2
CH
3
, —CH
2
OCH
3
, —CH
2
OCH
2
CH
2
OCH
3
, methoxyethoxyethoxymethyl, aryloxymethyl, phenyl, Cl, CN or NO
2
, —CH
2
COOR or —CH
2
NHCOR″ (where R″ is C
1
-C
6
alkyl or a phenyl or biphenyl group).
The invention also extends to polymeric products having the general formula
where, R
1
may be the same as or different to R′, which may be the same as or different to R
2
, which may be the same as or different to R
2′
, and each of R
1
,R
1′
,R
2
and R
2′
may be a hydrogen atom or CH
3
, CH
3
CH
2
—, —OCH
3
, —OCH
2
CH
3
, —CH
2
OCH
3
, —CH
2
OCH
2
CH
2
OCH
3
, methoxyethoxyethoxymethyl, aryloxymethyl, phenyl, Cl, CN or NO
2
, —CH
2
COOR or —CH
2
NHCOR′″ (where R′″ is C
1
-C
6
alkyl or a phenyl or biphenyl group), or a C
1
-C
5
alkyl group, or an a

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