In re Smith

481 F.2d 910, 178 U.S.P.Q. (BNA) 620, 1973 CCPA LEXIS 294
CourtCourt of Customs and Patent Appeals
DecidedAugust 2, 1973
DocketPatent Appeal No. 8935
StatusPublished
Cited by43 cases

This text of 481 F.2d 910 (In re Smith) is published on Counsel Stack Legal Research, covering Court of Customs and Patent Appeals primary law. Counsel Stack provides free access to over 12 million legal documents including statutes, case law, regulations, and constitutions.

Bluebook
In re Smith, 481 F.2d 910, 178 U.S.P.Q. (BNA) 620, 1973 CCPA LEXIS 294 (ccpa 1973).

Opinion

LANE, Judge.

This is an appeal from the decision of the Patent Office Board of Appeals sustaining the § 112 rejection of claims 1, 6, 7, 13 and 51 of appellants’ application Serial No. 527,399 filed February 10, 1966, as a continuation-in-part of application Serial No. 290,218 filed June 24, 1963. We reverse.

The Invention

The claims are drawn to polymers which are cationically active at the ends. These polymers have the nonterminating characteristic of so-called “living” polymers. Appellants explain the concept in their brief as follows:

Polycationically active polymers, i. e., polymers, in which both ends of the polymer chain are cationically active, are “living polymers”. That is, they behave as though they were non-terminated and, at each end of the chain, can continue to “grow” or initiate the polymerization of a cationically polymerizable monomer, such as tetrahydrofuran. Thus, for example, if tetrahydrofuran monomer is added to a polycationically active polymer, it will polymerize onto both ends thereof, producing a higher molecular weight polymer which is also cationally [sic] active at each end of the polymer chain and which therefor[e] is polycationically active.

Appellants note that whereas previously discovered “living” polymers have been anionic, the present polymers are cationic. They state that:

Among the more important uses of such polymers is in the preparation of block copolymers and of polymers having various terminating groups such as polymeric polyamines, polymeric polyisocyanates and polymeric polythiols. They are also valuable polymeric alkylating agents.

Claim 1 broadly defines the polymer as cationically active at at least two ends by virtue of defined radicals and as “free of alkylatable groups.” The claim also identifies the “living,” or polycationic, activity of the polymer in terms of the polymer’s capacity to react in specified ways. Claim 1 reads as follows:

1. A polymer which is free of alkylatable groups and which is eationically active at at least two ends, each of which ends having associated therewith only a radical which:
(1) in anionic form is a non-terminating anion when 2 mol percent of a dissolved salt containing said anion is present during the polymerization of 99 mol percent tetrahydrofuran and 1 mol percent ethylene oxide with 2 mol percent of boron trifluoride as polymerization initiator at 20°C. to provide at least about 50 percent conversion of said monomers to polymer, and
(2) is an anion of a protonic acid stronger than 100% sulfuric acid,
said poly-cationic activity being characterized by said polymer’s ability (a) to react with at least a two-fold molar excess of ammonia at a temperature below about 25 °C. to produce a polymeric polyprimary amine or polyamide [912]*912in which the amine or amide groups are in the terminal positions, and (b) to initiate the polymerization of tetrahydrofuran monomer at 25° C.

The other claims on appeal, dependent on claim 1, impose limitations not pertinent to the questions on this appeal.

Referring to the limitation in the claims to the effect that the polymeric moiety be “free of alkylatable groups,” appellants state in their brief:

The absence of alkylatable groups in the polymeric moiety is desirable because the living polymers are themselves effective alkylating agents and thus would tend to interact with any alkylatable group on the polymeric moiety, destroying the desired “living” characteristics.

As will be seen, that limitation is at issue in this appeal. The specification does not expressly disclose that the final polymer be free of alkylatable groups in the polymeric moiety (as opposed to the end units), and claim 1 on appeal is not an original claim.1

The specification discloses several methods of making the polymers:

The substantially linearpoly-cationically active polymers of this invention can be prepared by two general methods. The first method involves direct conversion of monomer [acid polymerizable monomers such as tettrahydrofuran and sym-trioxane] to a di-cationically active polymer, using certain catalysts * * *. In a second method, preformed polymers in the 400 to 100,000 molecular weight range and having certain functional groupings are converted to poly-cationieally active polymers, as hereinafter described.

The “second method” is characterized as an indirect conversion process which can produce “either linear, di-cationically active or branched poly-cationically active polymers, depending upon the state of branching and terminal group functionality of the preformed polymer.”

The indirect method uses a polymer rather than a monomer as a starting material. The specification discloses the following:

Although the direct method of preparation of the di-cationically active polymers of this invention is extremely useful, it is generally limited to certain eationically polymerizable monomers, as explained previously. Considerable versatility is provided by an indirect method of preparing a terminally polycationically active polymer which utilizes as a starting material a preformed polymer (i. e. prepolymer) which has certain functional substituents only in terminal positions and which is otherwise free of alkylatable groupings (e. g. olefin, amine, hydroxyl, thiol, carboxylic acid, etc.). Appropriate prepolymers can be classified in two categories:
I. Polymers containing -OH or -SH (or the alkali metal salts thereof), -COOH or S03H terminal groups can be converted to terminally poly-cationically active polymers by reaction with either a non-terminating catalyst parent acid, or certain derivatives thereof as specified below, wherein the catalyst parent acid is capable of initiating the cationic polymerization of tetrahydrofuran per se.
-x- * -x- * * *
II. Polymers containing acyl (i. e. carbonyl or sulfonyl) halide terminal groups, preferably acyl chloride or acyl bromide end groups, may be converted to polymeric mixed anhydrides by reaction with a non-terminating acid (i. e. catalyst parent acid) capable of initiating the polymerization of tetrahydrofuran, or a salt thereof, preferably a silver salt thereof. Illustrative reactants for the preparation of terminally poly-cationically active polymers form the abovementioned prepolymers include FSOaAg, [913]*913CFSOsSOsH, CFsSOgAg, HC104 and AgC104.

In addition to detailing how to make the claimed polymers directly from certain monomers and indirectly starting with preformed polymers, the specification provides disclosure on how to make the performed polymers and on how to use the claimed polymers. Methods of taking advantage of the polymers’ capacity as an alkylating agent are among the uses disclosed. The specification includes a number of examples which illustrate the methods of making and using particular embodiments of the invention.

The Decision of the Board

The issues before us are best introduced by the following selected portions of the board’s opinion:

Claims 1, * * * 6, 7, 13 and 51 stand rejected as failing to comply with the provisions of 35 U.S.C.

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Bluebook (online)
481 F.2d 910, 178 U.S.P.Q. (BNA) 620, 1973 CCPA LEXIS 294, Counsel Stack Legal Research, https://law.counselstack.com/opinion/in-re-smith-ccpa-1973.