In Re Dirk M. Brouwer and Elizabeth M. Van De Vondervoort

77 F.3d 422, 1996 WL 50185
CourtCourt of Appeals for the Federal Circuit
DecidedFebruary 8, 1996
Docket92-1225
StatusPublished
Cited by1 cases

This text of 77 F.3d 422 (In Re Dirk M. Brouwer and Elizabeth M. Van De Vondervoort) is published on Counsel Stack Legal Research, covering Court of Appeals for the Federal Circuit primary law. Counsel Stack provides free access to over 12 million legal documents including statutes, case law, regulations, and constitutions.

Bluebook
In Re Dirk M. Brouwer and Elizabeth M. Van De Vondervoort, 77 F.3d 422, 1996 WL 50185 (Fed. Cir. 1996).

Opinion

PER CURIAM.

This appeal is from the December 9, 1991, reconsideration decision of the United States Patent and Trademark Office (PTO) Board of Patent Appeals and Interferences (Board), Appeal No. 90-1349. That decision adhered to the Board’s March 18, 1991, decision affirming the examiner’s rejection of claims 8 through 27 of Brouwer and Van De Vonder-voort’s (collectively Brouwer) application serial no. 98,154, a division of application serial no. 831,398, filed February 20, 1986, now U.S. Patent No. 4,728,695 (crosslinked resins containing thermally stable sulfonic acid groups). The real party in interest is Shell Oil Company, the assignee of any patent issuing from the application.

The rejection of the above claims was predicated solely on obviousness, per 35 U.S.C. § 103, in view of the combined teaching of two references. 1 Because, under the legally correct method for determining obviousness, the claimed process was not' prima facie obvious in view of the cited prior art references, we reverse.

The Invention

Brouwer’s application is directed to a process for preparing sulfoalkylated polystyre-nedivinylbenzene resins. Claim 8, the principal claim on appeal, 2 is as follows:

8. A process for the preparation of a catalyst comprising an aryl group having a functional substituent group of general formula
(COOM)b I -(CH2)a-C-[G(H)(Rl)-CH2-S03M]d (I), I He
wherein a is O or 1, b is 1 or 2, d is 1 or 2, e is 01 or 1, b + d + e = 3, R 1 represents H or a Cl to C4 alkyl group and M is a proton or another cation; which process comprises the steps of
a) reacting (1) a crosslinked resin comprising at least one substituted aryl group having a functional substituent group of general formula
Rb 2 I —(CH2)a-C-H (II), I He
*424 wherein a, b, and e have the same meaning as in general formula (I), b + e = 2, R 2 is a - CN or a carboxyester group and if b is 2, each R 2 represents a -CN or a carboxyes-ter group, and
(2) an ester of an alkenesulfonic acid of general formula
C(H) (Rl) = C(H)-SOgR3 (III),
wherein R 1 has the same meaning as in general formula (I), and R 3 is a hydrocar-byl group, under conditions suitable for the formation of an addition product of general formula
Rb 2 I —(CH2)a-C-LC(H) (R1-CH2-SOsR8],i (IV), —a
wherein a, b, d, e and R 1 have the same meaning as in general formula (I), b + d + e = 3, R 2 has the same meaning as in general formula (II) and R 3 has the same meaning as in general formula (III), and then
(b) hydrolyzing the addition product of general formula (IV) to produce a compound having a functional group of general formula (I).

Brouwer’s U.S. Patent No. 4,728,695 covers the sulfoalkylated resins resulting from the process recited in claim 8. In other words, viewed as of the time the claimed process was invented, claim 8 recites a process of reacting a crosslinked resin with an ester of an alkenesulfonic acid to make a new, nonobvious sulfoalkylated resin catalyst. The ’695 patent, like the application at bar, claims priority to the February 1986 parent application.

The Rejection

The examiner rejected claims 8 through 27 in light of the combined teaching of the two references noted above. As Brouwer acknowledges, Distler teaches so-called “Michael addition” reactions 3 in which a vinylsulfonate is reacted with an active methylene group-containing compound. Distler, however, neither discloses nor suggests making a catalyst by reacting an ester of an alkenesulfonic acid with a crosslinked resin; instead, Distler discloses simple, well-defined compounds the derivatives of which would not be expected to exhibit the catalytic activity and thermal stability of the sulfoalkylated resin made according to the process of claim 8. Specifically, the crosslinked resin recited in claim 8, unlike the Distler compound having an active methylene group, has an aryl-pendant -CN or carboxyester functional group. Morrison & Boyd’s Organic Chemistry broadly discloses Michael addition reactions with two simple hydrocarbons; like Distler, it neither discloses nor suggests reacting an ester of an alkenesulfonic acid with a crosslinked resin. The examiner explained his initial rejections thusly:

Process of preparing polymer by using a unsaturated compound with active methylene substrate is well known as shown by Distler or Organic Chem. Applicants’ methylene unit (III) possess[es] the characteristics required to carry out reactions of the Michael-type reactions. In re Durden, [763 F.2d 1406] 226 USPQ 359 [ (Fed.Cir. 1985) ].

Importantly, the examiner discussed no references containing any suggestion or motivation either (a) to use a resin-substituted methylene reactant in the generic addition reaction taught by the cited references, or (b) to obtain the specific sulfoalkylated resin catalyst made according to the process of claim 8. The examiner offered this same explanation, virtually verbatim, in both his final rejection and his answer to Brouwer’s appeal to the Board.

On appeal, the Board affirmed the examiner’s rejection. According to the Board,

The basic difference between the claimed Michael addition reaction and reaction “(n)” disclosed on page 304 of Distler is that the latter’s methylene reactant is not attached to a resin as called for by the claims. Thus, the examiner considers that although Distler does not disclose the *425 claimed methylene reactant attached to a resin, one skilled in the art would have expected that reacting the same with vinyl-sulfonic acid would result in the claimed Michael adduct.... [0]ne desiring to make a sulfoalkylated resin would have found it obvious to do so via a Michael addition reaction such as reaction “(n)” of Distler by selecting a resin substituted methylene reactant.

In other words, the Board concluded that one desiring to make the nonobvious resin resulting from the process recited in claim 8 would know, on the basis of Distler, how to make it.

Free access — add to your briefcase to read the full text and ask questions with AI

Related

Astra Aktiebolag v. Andrx Pharmaceuticals, Inc.
222 F. Supp. 2d 423 (S.D. New York, 2002)

Cite This Page — Counsel Stack

Bluebook (online)
77 F.3d 422, 1996 WL 50185, Counsel Stack Legal Research, https://law.counselstack.com/opinion/in-re-dirk-m-brouwer-and-elizabeth-m-van-de-vondervoort-cafc-1996.