Ashland Oil, Inc. v. Delta Resins & Refractories, Inc.

776 F.2d 281, 227 U.S.P.Q. (BNA) 657, 1985 U.S. App. LEXIS 15309
CourtCourt of Appeals for the Federal Circuit
DecidedOctober 25, 1985
DocketAppeal 84-1779
StatusPublished
Cited by130 cases

This text of 776 F.2d 281 (Ashland Oil, Inc. v. Delta Resins & Refractories, Inc.) 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
Ashland Oil, Inc. v. Delta Resins & Refractories, Inc., 776 F.2d 281, 227 U.S.P.Q. (BNA) 657, 1985 U.S. App. LEXIS 15309 (Fed. Cir. 1985).

Opinion

KASHIWA, Circuit Judge.

Ashland Oil, Inc. (Ashland) appeals from the judgment of the United States District Court for the Eastern District of Michigan, Southern Division, 587 F.Supp. 1406 (1984), holding claims 1, 2, 7 and 10 of U.S. Patent No. 3,485,797 (the ’797 patent), claims 14 and 19 of U.S. Patent No. 3,409,579 (the ’579 patent), and claim 17 of U.S. Patent No. 3,676,392 (the ’392 patent) invalid under 35 U.S.C. § 103. We reverse and remand.

Background

Ashland is the assignee of the three patents involved in this case, which were issued to Dr. Janis Robins. These patents are directed to certain chemical products and processes finding ultimate use in the *284 foundry industry. One method of forming metal castings in the foundry industry involves compacting sand around a pattern to form a sand mold, removing the pattern, and then pouring molten metal into the sand mold. This process often involves the use of internal sand cores around which the molten metal flows to produce various internal configurations.

A chemical binder, for example a phenolic urethane formed by reacting a phenol-formaldehyde resin with a hardener component, such as a polyisocyanate, and a curing agent, such as a tertiary amine, is mixed with the sand, causing the sand-binder mixture to harden at a predetermined rate. After the sand mold mixture has hardened, the mixture retains its shape during the pouring of the molten metal. After the metal solidifies the binder must break down to permit the sand to be readily dislodged from the casting.

. An optimized sand-binder mixture should have a slow or negligible curing period after the initial mixing of the binder with the sand, i.e., the work time, followed by a period of rapid curing. During the work time, the sand-binder mixture remains flowable, due to negligible curing or hardening, to allow easy forming of the mixture to conform to the pattern. Rapid curing after the mold has been formed allows the sand-binder mixture to rapidly reach its hardened state, thus permitting initiation of molten metal pouring.

Ashland sued Delta Resins & Refractories, Inc. (Delta) 1 for infringement of claims 1, 2, 7 and 10 of the '797 patent, claims 14 and 19 of the ’579 patent and claim 17 of the ’392 patent. Claims 1, 2, and 7 of the ’797 patent are directed to a process for producing a phenol-formaldeyhde resin which may be used in producing a chemical binder useful in the formation sand molds. Claim 10 of the ’797 patent is directed to one of the resin products derived from this process.

Claim 1 of the ’797 patent is a broad process claim 2 directed to reacting a phenol and aldehyde in the presence of a catalyst and reads as follows:

*285 1. A process for the preparation of phenol aldehyde reaction products which comprises

reacting a phenol having the general formula

T wherein X, Y, and Z are hydrogen, hydrocarbon radicals, oxyhydrocarbon radicals or halogen, with' an aldehyde having the general formula R’CHO wherein

R1 is hydrogen or a hydrocarbon radical of 1-8 carbon atoms at a mole ratio of aldehyde to phenol of greater than 1,

in the liquid phase under substantially anhydrous conditions with the removal of water above 100° C and

at temperatures below about 130° C in the presence of catalytic concentrations of a soluble divalent metal salt dissolved in the reaction medium.

Claim 10 of the ’797 patent is directed to a phenol-formaldehyde resin (Pep resin) 3 and reads as follows:

10. The phenol formaldehyde resin having the general

radical or halogen, meta to the hydroxyl group of the phenol; m and n are numbers the sum of which is at least two and the ratio of m-to-n is greater than one; and A is a hydrogen or a methylol group, the molar ratio of said methylol group to hydrogen being at least one. 4

*286 Claim 14 of the ’579 patent 5 is a dependent claim 6 directed to a foundry mix which contains sand as the major constituent and up to 10% by weight, based upon the weight of the sand, of a binder composition. The binder composition comprises in admixture the Pep resin as described in claim 10 of the ’797 patent, a hardener component comprising a liquid polyisocyanate containing at least two isocyanate groups, and a curing agent comprising a tertiary amine.

Claim 19 of the ’579 patent is a dependent claim 7 which reads as follows:

19. The process of preparing shaped foundry products which comprises:

(a) forming a foundry mix by uniformly distributing on a foundry aggregate containing sand as the major constituent a binding amount of up to 10% based on the weight of the aggregate of a binder composition obtained by combining [a phenolic resin having the general formula

wherein R is hydrogen or a phenolic substituent meta to the hydroxyl group of the phenol, m and n are numbers the sum of which is at least 2, and the ratio of m-to-n is at least 1, and X is a hydrogen or a methylol group, the molar ratio of said methylol group-to-hydrogen being at least 1] and hardener component of claim 1, said polyisocyanate being employed in a concentration of 10 to 5007» by weight of the phenolic resin;

(b) shaping the foundry mix in a mold; and

(c) contacting the shaped foundry mix with a tertiary amine until the binder is cured.

(bracketed material added, see supra note 7).

Claim 17 of the ’392 patent 8 is a dependent claim 9 which reads as follows:

*287 17. A foundry mix containing sand as the major constituent, and a binding amount of up to 10 percent based on the weight of sand of the resin composition [ , said resin composition comprising in admixture,

a benzylic ether resin which has the general

the hydroxyl group of the phenol, m and n are numbers the sum of which is at least 2, X is an end-group from the group consisting of hydrogen and methylol, and wherein m is at least 1 and the sum of m and the number of methylol end-groups is at least two,

a hardener component comprising a liquid

polyisocyanate containing at least two isocyanate groups and present in an amount equal to 10 to 500 weight percent based on the weight of the resin, and

a curing catalyst having a pK^, value in the

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Bluebook (online)
776 F.2d 281, 227 U.S.P.Q. (BNA) 657, 1985 U.S. App. LEXIS 15309, Counsel Stack Legal Research, https://law.counselstack.com/opinion/ashland-oil-inc-v-delta-resins-refractories-inc-cafc-1985.