Hedman v. Commissioner of Patents

253 F. Supp. 515, 148 U.S.P.Q. (BNA) 582, 1966 U.S. Dist. LEXIS 10301
CourtDistrict Court, District of Columbia
DecidedMarch 2, 1966
DocketCiv. A. No. 728-64
StatusPublished
Cited by3 cases

This text of 253 F. Supp. 515 (Hedman v. Commissioner of Patents) is published on Counsel Stack Legal Research, covering District Court, District of Columbia primary law. Counsel Stack provides free access to over 12 million legal documents including statutes, case law, regulations, and constitutions.

Bluebook
Hedman v. Commissioner of Patents, 253 F. Supp. 515, 148 U.S.P.Q. (BNA) 582, 1966 U.S. Dist. LEXIS 10301 (D.D.C. 1966).

Opinion

JACKSON, District Judge.

This is a civil action under 35 U.S.C. § 145 in which plaintiffs seek an adjudication that they are entitled to receive a patent for the invention specified in Claims 1-20, inclusive, of application Serial No. 796,771 entitled “Alfin Catalyst Copolymerization”, filed March 3, 1959, by plaintiffs Edward A. Hedman and Bruce W. Hubbard, Jr., and assigned to co-plaintiff The Richardson Company. The application in suit is a continuation-in-part of application Serial No. 727,057, filed April 8, 1958, now abandoned.

Plaintiffs’ invention is directed to Alfin catalyzed copolymerization of either butadiene-1,3 or isoprene with butene-2, which reaction produces relatively high molecular weight copolymers.

Claims 1 and 10 are illustrative of the invention and read as follows:

1. The copolymerization product of a conjugated unsaturated diolefin selected from the class consisting of butadiene-1,3 and isoprene with butene-2 having a minimum dilute solution viscosity of between about 3-6.
10. The method of making a high molecular weight polymer which comprises reacting a conjugated unsaturated diolefin selected from the class consisting of butadiene-1,3 and isoprene with butene-2 in the presence of an Alfin catalyst selected from the class consisting of: (1) a mixture of an alkali metal alkenyl, alkoxide and halide, and (2) a mixture of an alkali metal benzyl, alkoxide and halide.

The three references relied upon by the Patent Office tribunals in rejecting plaintiffs’ claimed subject matter as obvious and unpatentable over the prior art under 35 U.S.C. § 103 are as follows:

Goodrich-Gulf (Belgium) 543,292 June 2, 1956

Rokityanskii, I. V., Polymerization of Mixtures of 1,3-Butadiene with 2-Butene and with Pentane by Sodium. In Nat.Petroleum News. Vol. 37, pages R133-R136.

Morton, A. A., The Alfin Catalysts. In J.A.C.S. Yol. 69, pages 950-961. April 1947.

[517]*517A fourth reference was introduced in evidence at the trial, but defendant’s brief states that Carlson et al. U. S. Patent No. 3,135,725 “is in no way relied upon to reject plaintiffs’ claims.”

All of Claims 1-20 have been rejected by the Patent Office tribunals as unpatentable over Morton in view of Rokityanskii. However only product Claims 1- 9, but not process Claims 10-20, have been rejected by the Patent Office as unpatentable over the Goodrich-Gulf Belgian patent.

Goodrich-Gulf broadly discloses inter alia the copolymerization of conjugated polyolefins with aliphatic monoolefins, and in particular this Belgian patent states that “the conjugated diolefin hydrocarbon may be a 1,3-butadiene hydrocarbon such as 1,3-butadiene (which is the simplest conjugated diolefin) or a methyl-substituted 1,3-butadiene, i. e., isoprene or piperylene.”

The reference also broadly discloses that “the other hydrocarbon” which is copolymerized with the conjugated poly-olefin “may be an aliphatic monoolefin such as ethylene, propylene, 1-butene, 2- butene, * *

With regard to the high molecular weight polymers obtained by Goodrich-Gulf, this Belgian patent states that “polymer products obtained by this method are generally resinous or rubbery materials ordinarily of substantially linear structure and of high molecular weight, i. e., a molecular weight usually higher than 5,000, normally higher than 10,000, and even occasionally rising to a value of 1,000,000 or more.” Plaintiffs’ isoprene/butene-2 copolymers have an average viscosity molecular weight of approximately 750,000.

Among the 132 specific examples of Goodrich-Gulf, examples 90 and 91 are particularly pertinent, since these two examples both show the copolymerization of isoprene with 2-methyl-2-butene. The copolymer products formed are said to be “rubbery, vulcanizable and adhesive materials.” Since 2-methyl-2-butene is a next adjacent higher homologue of 2-butene it is reasonable to conclude that 2-butene should also be copolymerizable with isoprene and also with plaintiffs’ other claimed conjugated diolefin, 1,3-butadiene, in light of the teachings' of the Goodrich-Gulf reference relating to Ziegler catalyzed copolymerization.

Heterogeneous catalysis such as that of the Ziegler systems of Goodrich-Gulf and the Alfin systems of Morton is known to be a surface phenomenon. Thus, while it might be difficult to make a prediction in light of examples 90 and 91 of Goodrich-Gulf as to whether higher homologues such as 2-ethyl-2-butene and 2-n-propyl-2-butene would be copolymerizable with either isoprene or butadiene, it is reasonable to predict that 2-butene itself, which is a next adjacent lower homologue of 2-methyl-2-butene and therefore has a smaller monomeric molecular configuration, should be copolymerizable with both isoprene and 1,3-butadiene, at least in the presence of the Ziegler catalysts of Goodrich-Gulf.

Although the Goodrich-Gulf Ziegler catalysts and the Morton Alfin catalysts are both heterogeneous coordinated anionic organometallic systems, it would be difficult for an ordinarily skilled chemist to make a reasonable prediction in light of Goodrich-Gulf as to whether butene-2 would be copolymerizable with isoprene or butadiene in the presence of an Alfin catalyst system. The Ziegler catalysts are mixtures of organometallic compounds, at least one of which must be a heavy metal compound. The Alfin catalysts on the other hand are mixtures of organoalkali metal, usually organosodium, compounds with at least one inorganic alkali metal compound, usually sodium chloride. Since sodium and potassium are alkali metals, not heavy metals, it would be quite difficult to extend the Goodrich-Gulf disclosures relating to Ziegler catalysts to the Alfin catalysts of Morton which are used by plaintiffs. However, the Court notes that plaintiffs’ copolymer product Claims 1-9 presently contain no catalyst limitations. In the total absence of such catalyst limitations, product Claims 1-9 cover the Ziegler catalyzed copolymers of [518]*518Goodrich-Gulf just as much as these product claims cover the Alfin catalyzed copolymers of Morton. Therefore, the Court agrees with defendant and the Patent Office tribunals that the claimed subject matter of plaintiffs’ Claims 1-9, namely, a high molecular weight copolymerization product of either 1,8-buta-diene or isoprene with butene-2, would have been obvious at the time plaintiffs' invention was made to an ordinarily skilled chemist in view of the specific disclosures and suggestions of the Goodrich-GuIf Belgium patent.

Before proceeding to the second ground of rejection, two other things might be mentioned. First, the Court notes without comment that generic product Claim 1 as originally filed specified that “the copolymerization product” was that formed “in the presence of an Alfin catalyst,” which catalyst limitation was subsequently cancelled from the product claims, but not the process of manufacture claims, by plaintiffs’ first prosecution amendment. Second, with regard to the time plaintiffs’ invention was made, an attempt was made at the trial to establish a date of invention by alleged actual reduction to practice in December, 1956.

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Bluebook (online)
253 F. Supp. 515, 148 U.S.P.Q. (BNA) 582, 1966 U.S. Dist. LEXIS 10301, Counsel Stack Legal Research, https://law.counselstack.com/opinion/hedman-v-commissioner-of-patents-dcd-1966.