Application of Johnson

Citation558 F.2d 1008
Decision Date16 June 1977
Docket NumberPatent Appeal No. 76-643.
PartiesApplication of Robert N. JOHNSON and Alford G. Farnham.
CourtUnited States Court of Customs and Patent Appeals

Robert C. Brown, New York City, Aldo J. Cozzi, Union City, N. J., attorneys of record, for appellants; James C. Arvantes, Arlington, Va., of counsel.

Joseph F. Nakamura, Washington, D. C., for the Commissioner of Patents; Henry W. Tarring, II, Washington, D. C., of counsel.

Before MARKEY, Chief Judge, and RICH, BALDWIN, LANE and MILLER, Judges.

MARKEY, Chief Judge.

This appeal is from the decision of the Patent and Trademark Office (PTO) Board of Appeals affirming the rejection under 35 U.S.C. §§ 102 or 103 (the rejection also raises a written description issue under 35 U.S.C. § 112, first paragraph) of claims 1-9, 64, and 68-70 and the rejection under 35 U.S.C. § 112, first paragraph (enablement) and second paragraph (indefiniteness), of claims 64 and 68-72 in appellants' application No. 230,091 filed February 28, 1972 (the 1972 application) for "Polyarylene Polyethers."1 The 1972 application is a continuation-in-part of three earlier applications, the earliest being application No. 295,519 filed July 16, 1963 (the 1963 application). We reverse.

The Invention

The invention is in the field of polymer chemistry and more specifically relates to linear thermoplastic polyarylene polyether polymers composed of recurring units having the general formula ——O-E-O-E'—— where O represents an oxygen atom,2 E represents the residuum of a dihydric phenol3 compound, and E' represents the residuum of a benzenoid compound having one or more inert electron withdrawing groups4 in the ortho5 or para6 positions to the valence bonds and where both E and E' are bonded to the ether oxygens through aromatic carbon atoms.

Appellants describe a method of synthesizing these polymers by reacting a double alkali metal salt of a dihydric phenol with a dihalobenzenoid compound in the presence of certain solvents under substantially anhydrous reaction conditions.

The 1972 application includes the following disclosure with respect to the electron withdrawing group found in E' and in the E' precursor compound, that is, in the compound which is the predecessor of E' in the above general formula (we have designated paragraphs A and B and have added emphasis thereto):

Any electron withdrawing group can be employed as the activator group in these compounds. It should be, of course, inert to the reaction, but otherwise its structure is not critical. Preferred are the strong activating groups such as the sulfone group

O | | (-S-) bonding two halogen substituted | | O

benzenoid nuclei as in the 4,4'-dichlorodiphenyl sulfone and 4,4'-difluorodiphenyl sulfone, although such other strong withdrawing groups hereinafter mentioned can also be used with equal ease.
The more powerful of the electron withdrawing groups give the fastest reactions and hence are preferred. It is further preferred that the ring contain no electron supplying groups on the same benzenoid nucleus as the halogen; however, the presence of other groups on the nucleus or in the residuum of the compound can be tolerated. Preferably, all of the substituents on the benzenoid nucleus are either hydrogen (zero electron withdrawing), or other groups having a positive sigma * value, as set forth in J.F. Bunnett in Chem.Rev. 49 273 (1951) and Quart.Rev., 12, 1 (1958). See also Taft, Steric Effects in Organic Chemistry, John Wiley & Sons (1956), chapter 13; Chem. Rev., 53, 222; JACS, 74, 3120; and JACS, 75, 4231.7
The electron withdrawing group of the dihalobenzenoid compound can function either through the resonance of the aromatic ring, as indicated by those groups having a high sigma * value, i.e., above about + 0.7 or by induction as in perfluoro compounds and like electron sinks.
A
Preferably the activating group should have a high sigma * value, preferably above 1.0, although sufficient activity to promote the reaction is evidenced in those groups having a sigma value above 0.7, although the reaction rate with such a low powered electron withdrawing group may be somewhat low.
The activating group can be basically either of two types:
(a) monovalent groups that activate one or more halogens on the same ring as a nitro group, phenylsulfone, or alkylsulfone, cyano, trifluoromethyl, nitroso, and hetero nitrogen as in pyridine.
(b) divalent group sic which can activate displacement of halogens on two different

O || rings, such as the sulfone group -S-; the || O O || carbonyl group -C-; the vinyl group H O | || -C= C-; the sulfoxide group -S-; the | H azo-group -N = N-; the saturated fluorocarbon groups -CF2CF2 -; organic phosphine O || oxides -P-; where R is a hydrocarbon || R group, and the ethylidene group X -C- X || -C- where X can be hydrogen or halogen or which can activate halogens on the same ring such as with difluorobenzoquinone, 1,4- or 1,5- or 1,8-difluoroanthraquinone.

B
Those skilled in the art will understand that a plurality of electron withdrawing groups may be employed if desired, including electron withdrawing groups having a sigma * value below about + 0.7 provided the cumulative sigma * influence on each of the reactive halogen groups of the halobenzenoid compound is at least about + 0.7.
The Disclosure and Prosecution History of the 1963 Application

To understand the written description issue in this appeal, it is necessary to summarize the disclosure and prosecution history of the 1963 application. The 1963 application described (and claimed) in haec verba a genus of polymers as defined by the above general formula. That application stated:

The high molecular weight polyarylene polyethers of the present invention are the linear thermoplastic reaction products of an alkali metal double salt of a dihydric phenol and a dihalobenzenoid compound. Characteristically, this polymer has a basic structure composed of recurring units having the formula

-O-E-O-E'-

wherein E is the residuum of the dihydric phenol and E' is the residuum of the benzenoid compound, both of which are valently bonded to the ether oxygen through aromatic carbon atoms, as hereinafter more fully discussed. Polymers of this type exhibit excellent strength and toughness properties as well as outstanding thermal, oxidative and chemical stability.

The 1963 application then discussed the identity of E and the E' precursor compound, that is, the compound which is the predecessor of E in the general formula. It stated:

The residuum E of the dihydric phenol of these alkali metal salts is not narrowly critical. It can be, for instance, a mononuclear phenylene group as results from hydroquinone and resorcinol, or it may be a di- or polynuclear residuum. Likewise it is possible that the residuum be substituted with other inert nuclear substituents such as halogen, alkyl, alkoxy and like inert substituents.
* * * * * *
Such dinuclear phenols can be characterized as having the structure:

(Y)r (Y1)z | | HO(Ar - R - Ar)OH

wherein Ar is an aromatic group and preferably is a phenylene group, Y and Y1 can be the same or different inert substituent groups as alkyl groups having from 1 to 4 carbon atoms, halogen atoms, i. e. fluorine, chlorine, bromine or iodine, or alkoxy radicals having from 1 to 4 carbon atoms, r and z are integers having a value from 0 to 4, inclusive, and R is representative of a bond between aromatic carbon atoms as in dihydroxydiphenyl, or is a divalent radical, including for

O || example, inorganic radicals as - C -, - O - -S-, -S-S-, -SO2-, and divalent

organic hydrocarbon radicals such as alkylene, alkylidene, cycloaliphatic, or the halogen, alkyl, aryl or like substituted alkylene, alkylidene and cycloaliphatic radicals as well as alkalicyclic, alkarylene and aromatic radicals and a ring fused to both Ar groups.

The application then mentioned by name some fifty specific dihydric dinuclear phenol (bisphenol) compounds which could be the E precursor compound. The application further stated:

A preferred form of the polyarylene polyethers of this invention are those prepared using the dihydric polynuclear phenols of the following four types, including the derivatives thereof which are substituted with inert substituent groups
in which the R group represents hydrogen, lower alkyl, lower aryl and the halogen substituted groups thereof, which can be the same or different.

Turning to the identity of the E' precursor compound, the application stated:

Any dihalobenzenoid compound or mixture of dihalobenzenoid compounds can be employed in this invention which compound or compounds has the two halogens bonded to benzene rings having an electron withdrawing group in at least one of the positions ortho and para to the halogen group. The dihalobenzenoid compound can be either mononuclear where the halogens are attached to the same benzenoid ring or polynuclear where they are attached to different benzenoid rings, as long as there is the activating electron withdrawing group in the ortho or para position of that benzenoid nucleus.

The 1963 application also included a discussion of the electron withdrawing group that was substantially the same as the paragraphs quoted above from the 1972 application.

The 1963 application contained twenty-six "examples" disclosing in detail the physical and chemical characteristics of fifteen species of polyarylene polyethers. One of the species was the polymer composed of these recurring structural units (which we designate as species 1):8

Another species disclosed was the polymer composed of these recurring structural units (which we designate as species 2):9

Appellants' 1963 application became involved in a three-party interference10 which resulted in an award of priority adverse to appellants from which they did not appeal.11 The sole count of the interference recited species 1.

After their involvement in the interference ended, appellants filed the 1972 application, and they...

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