The Federal Circuit Adds Color to Formulation Claims in Olaplex v. L’Oréal

(as published in the May 2021 issue of the American Chemical Society's Northeast Section publication of The Nucleus)

Olaplex v. L’Oréal involves a particular problem that can arise when claiming pharmaceutical and consumer product formulations. In particular, a chemical compound, such as maleic acid as recited in the asserted claims, may be converted to different forms (e.g., salts, such as maleate or hydrogen maleate) once added to a formulation. Claim limitations that aim to specify the amounts or concentrations of such compounds in claimed formulations can be problematic when it is unclear how they are to be calculated.

Background

L’Oréal markets products to protect hair that has been colored or bleached. Olaplex, the owner of U.S. Patent No. 9,668,954 (the ’954 patent), alleged in district court that L’Oréal infringed claims of the ’954 patent through three of L’Oréal’s maleic acid-containing hair treatment systems. Each system consists of three iterative treatments (referred to by the court collectively as the Step 1, Step 2 and Step 3 products). Adopting Olaplex’s claim construction involving how to calculate the recited amount of maleic acid, the district court granted summary judgment finding infringement of the asserted claims, and issued a permanent injunction that blocked L’Oréal from making and/or selling its Step 1, 2 and 3 hair products. L’Oréal appealed. On March 4, 2021, the Federal Circuit affirmed the lower court’s claim construction, but remanded to the district court for trial on the issue of infringement due to remaining questions of material fact under the adopted claim construction. After initially granting L’Oréal’s motion for a stay, the Federal Circuit also vacated the permanent injunction.

Claims on Appeal

The claims on appeal were the “breakage claims” 14-16, 18 and 24-28 of the ’954 patent. In an earlier decision on L’Oréal’s petition for post-grant review of the ’954 patent, the PTAB determined that the originally asserted claims—except for the breakage claims—were unpatentable as obvious. Claim 14, including base claim 1 and intervening claims 12 and 13, is reproduced below:

1. A method for bleaching hair comprising: (a) mixing a bleach powder and a developer to form a bleaching formulation; (b) mixing an active agent formulation comprising an active agent with the bleaching formulation to form a mixture, wherein the active agent is maleic acid; and (c) applying the mixture to the hair; wherein the active agent in the mixture is at a concentration ranging from about 0.1% by weight to about 50% by weight.

12. The method of claim 1, further comprising: (d) applying a second active agent formulation comprising maleic acid, wherein step (d) occurs subsequent to step (c).

13. The method of claim 12, wherein the second active agent formulation further comprises a conditioning agent.

14. The method of claim 13, wherein following step (d) breakage of the hair is decreased by at least 5% compared to hair bleached with the bleaching formulation in the absence of the active agent.

Claim Construction

The claim construction issue in this case represents a challenge in claiming formulations relating to how to go about defining the concentration of an agent that changes form in a mixture. Claim 14 of the ’954 patent is directed to a method of bleaching hair in the presence of a bleaching formulation to which maleic acid is added. As agreed to by both parties, maleic acid is fully neutralized and converted to maleate (a salt) upon addition to the bleaching formulation. Thus, “the mixture” formed in step (b) of claim 1 does not actually contain maleic acid, as recited in the claim, because it is converted to maleate in the basic environment of the bleaching formulation. This fact complicates the meaning of claim 1 in terms of how to understand the recited calculation of the maleic acid concentration.

Claim 1(b) includes the step of adding maleic acid to a bleaching solution to form a mixture, “wherein the [maleic acid] in the mixture is at a concentration ranging from about 0.1% by weight to about 50% by weight.” The problem noted by the court is that multiple constructions are possible.

L’Oréal argued that the claim should be construed as requiring maleic acid to be present in the mixture at the recited concentration, based on the plain language of the claim. By contrast, Olaplex argued that the claim should be construed as being based on the weight of maleic acid added into the active agent formulation, relative to the final weight of the mixture comprising the bleaching formulation. The district court agreed with Olaplex, and the Federal Circuit affirmed the construction. In doing so, the Federal Circuit acknowledged that under L’Oréal’s claim construction, the claim term “maleic acid” would be rendered meaningless and unsatisfied since, as agree to by both parties, “there would be no maleic acid in the final bleaching solution.”

The Federal Circuit relied on Wasica Fin. GmbH v. Cont’l Automotive Systems, Inc., in which the court held that “it is highly disfavored to construe terms in a way that renders them void, meaningless, or superfluous.”

Olaplex’s claim construction was also supported by Example 3 in the specification of the ’954 Patent, which describes the amount of maleic acid as by weight prior to mixing with the bleaching formulation, consistent with claim 1. In addition, the court credited testimony of Olaplex’s expert who explained that a person of ordinary skill in the art would understand that the recited maleic acid concentration refers to the amount of maleic acid in the active agent formulation before it is mixed with the bleaching formulation.

Summary Judgment of Infringement

The decreased breakage aspect of claim 14 depends upon the addition of the requisite amount of maleic acid to the bleaching formulation, as defined in claim 1. L’Oréal argued that summary judgment was not appropriate because there was a question of material fact as to whether its Step 1, 2, and 3 products contained maleic acid in the claimed amount.

With respect to the recited concentration of maleic acid, Olaplex’s expert was able to show by nuclear magnetic resonance (NMR) that L’Oréal’s Step 1 products contain added maleic acid between 10.2 and 10.6% by weight, well within the claimed range. L’Oréal countered that because the NMR testing was not able to distinguish between maleic acid and its salt forms, the testing failed to establish infringement because only maleic acid, if present in the correct amount, would have infringed the claims. Consistent with the affirmed claim construction, the Federal Circuit acknowledged that maleic acid salts (maleate, hydrogen maleate) detected in the mixture can serve as a proxy for determining the concentration of “maleic acid” since the salts were derived directly from the maleic acid that was added to L’Oréal’s products.  Accordingly, the Federal Circuit held that there was no question of material fact as to whether L’Oréal’s Step 1 products contain the claimed amount of maleic acid.

However, the Federal Circuit agreed with L’Oréal’s assertion that there was a question of material fact concerning whether the combination of its Step 1 and Step 2 products would have met the limitations concerning decrease in percent breakage as recited in claim 14. The court pointed to the district court’s lack of analysis in this regard and that it did not provide a basis in fact for the finding that the hair breakage limitations of claim 14 were met. The Federal Circuit also agreed with L’Oréal that questions of material fact existed with regard to other limitations as well, and that the Step 3 products did not infringe because they were “at-home” products outside of the scope of the claimed hair bleaching methods.

Thus, Olaplex has another appointment to return to district court. The Federal Circuit vacated the injunction and remanded for further proceedings.

Takeaways

• For prosecutors drafting formulation claims, it is important to consider what the actual components of your formulation are, keeping in mind that chemical compounds can undergo changes (e.g., acid-base reactions, racemization, hydrolysis, tautomerization) under certain conditions. Although the Federal Circuit’s flexible claim construction in this case is a victory for the patent holder, more precise claim drafting could have avoided this issue. The following are complementary claim approaches that could avoid issues raised in this case:

1. Include claims that specify the actual components of the final formulation (for example, maleate or other salt forms instead of maleic acid in this case);
2. Include claims that focus on the process by which the formulation is prepared (for example, a formulation made by adding maleic acid to a mixture).

• Another way to strengthen a formulation claim is to explain, at least in the specification, how the concentration of a component should be calculated. Is it based on the amount present in the formulation, or based on the amount added?
• This case also serves as a reminder that claim limitations will likely be construed in a way that avoids rendering them meaningless or superfluous.