US 8026378

US patent 8026378, titled "Glyceryl ether compounds and their use," was filed on November 22, 2006, and issued on September 27, 2011. The inventor is Sergey Selifonov. The original assignee was Segetis Inc. Current assignees are listed as GF Biochemicals Ltd and Aromagen Corp, though the listed assignees may be inaccurate according to Google Patents.

The abstract describes the patent's subject matter: "Glyceryl ether compounds prepared by the reaction of glycerol and olefin epoxides are disclosed. The compounds are renewable biomass-based surfactants useful as detergents and emulsifiers in formulations for cleaning, laundry, personal care, cosmetics, and industrial uses."

Legal Status and CAFC Dockets:
As of April 26, 2026, the patent's legal status is "Expired - Fee Related," with an adjusted expiration date of May 25, 2028, according to the Google Patents entry. However, the legal events history indicates a "Lapse for failure to pay maintenance fees" on November 4, 2019, with the patent expiring due to nonpayment of maintenance fees under 37 CFR 1.362, effective September 27, 2019. This suggests the patent has already expired due to non-payment of fees, despite the listed adjusted expiration date. No cases explicitly mentioning US patent 8026378 were found in the publicly available CAFC scheduled dockets for May, June, or July 2026.

Plain-Language Overview of Independent Claims:

• Claim 1: This claim defines a specific chemical compound. The compound's structure features a central portion with a substituent (R6), which can be hydrogen or a linear or branched alkyl group with 1 to 10 carbon atoms. Attached to this central portion are two "V" groups. Each "V" group represents either a 2,3-dihydroxypropyloxy (glyceryl ether) structure or a protected version of it, specifically a 1,3-dioxolane or 1,3-dioxane ring with two alkyl groups (R4 and R5) attached, or a derivative with a hydroxyl group. Essentially, Claim 1 covers various glyceryl ether compounds, including both unprotected and protected forms.

• Claim 2: This claim describes a method for producing the compound specified in Claim 1. The method involves three main steps:

  • a) Providing either glycerol (an unprotected form) or a specific protected form of glycerol (a compound where R4 and R5 are independently chosen from hydrogen, linear/branched/cyclic alkyl, alkenyl, aryl, or arylalkyl groups).
  • b) Providing an epoxide-containing compound, which can be either an epoxidized triglyceride or an epoxidized unsaturated fatty acid ester. In the fatty acid ester, the fatty acid portion has 8 to 24 carbon atoms, and the alcohol portion is derived from a linear or branched monohydric alcohol with 1 to 12 carbon atoms.
  • c) Carrying out a chemical reaction between the compounds from step (a) and step (b) in the presence of an acid or base catalyst.

As of April 26, 2026, no litigation specifically involving US patent 8026378 was found through public search channels, including those typically indexing patent litigation such as Unified Patents, CAFC, and PACER.

While Unified Patents offers a portal for searching litigation cases, a direct search for US8026378 in public search results did not yield specific case entries from their database. Similarly, searches for "US8026378 litigation," "US8026378 lawsuit," "US8026378 CAFC litigation," and "US8026378 PACER litigation" did not return any records of lawsuits pertaining to this particular patent. The search results regarding PACER explain the general functionality of the PACER Case Locator as a national index for federal court cases, but do not provide specific litigation details for US8026378. Furthermore, the CAFC results discuss various appellate cases, none of which are related to patent US8026378.

Therefore, based on the available information, there is no known litigation involving US patent 8026378.

Proceedings overview

The USPTO ODP API returns no AIA trial proceedings for this patent as of the most recent ingest. Therefore, there is no PTAB activity on file for US patent 8026378.

Strategic summary

As there are no PTAB proceedings on file for US patent 8026378, all claims (Claims 1, 2, and 3) remain untested by AIA trial proceedings. This means there is no estoppel landscape established by PTAB decisions, and all prior-art grounds are theoretically still available for a potential petitioner. The absence of PTAB activity could indicate that the patent has not been extensively asserted, or that prior art challenges have not been deemed strong enough to warrant an AIA trial.

Recommended next steps

If you are a defendant facing assertion of US patent 8026378, the absence of PTAB activity means that you would be initiating the first AIA trial proceeding. This presents an opportunity to challenge the patent's validity without being constrained by previous PTAB decisions or estoppel. A thorough prior art search, building on the obviousness analysis provided, would be a critical first step to identify strong grounds for a petition for Inter Partes Review (IPR).

Inventors

The sole named inventor is Sergey Selifonov. At the time of filing, he was associated with Segetis Inc., the original assignee. No unusual patterns, such as the inventor departing the original assignee within 12 months of filing, were identified.

Original assignee

The original assignee on the issued patent is Segetis Inc.

• Product/Business: Segetis Inc. was involved in the development and commercialization of bio-based chemicals. Specifically, the patent describes glyceryl ether compounds as renewable biomass-based surfactants useful as detergents and emulsifiers in various formulations (cleaning, laundry, personal care, cosmetics, industrial uses).
• Current Status: Segetis Inc. was acquired by GFBIOCHEMICALS LIMITED, as evidenced by the assignment recorded on 2016-04-07.

Assignment timeline

• 2008-10-28 (executed) / recorded 2009-01-28 — Reel 022168/0071

  • Conveyance: ASSIGNMENT
  • Assignor: SELIFONOV, SERGEY
  • Assignee: AROMAGEN CORPORATION
  • Correspondent: Robert S. Haffner, Fish & Richardson P.C., 60 South Sixth Street, Suite 3200, Minneapolis, MN, 55402. This correspondent appears on multiple records in this chain.
  • Context: Inventor assigning rights to an initial corporate entity.

• 2008-10-28 (executed) / recorded 2009-01-28 — Reel 022168/0109

  • Conveyance: ASSIGNMENT
  • Assignor: AROMAGEN CORPORATION
  • Assignee: SEGETIS, INC.
  • Correspondent: Robert S. Haffner, Fish & Richardson P.C., 60 South Sixth Street, Suite 3200, Minneapolis, MN, 55402. This correspondent appears on multiple records in this chain.
  • Context: Transfer of rights from an initial corporate entity to the original operating assignee.

• 2016-02-05 (executed) / recorded 2016-04-07 — Reel 038373/0362

  • Conveyance: ASSIGNMENT
  • Assignor: SEGETIS, INC.
  • Assignee: GFBIOCHEMICALS LIMITED
  • Correspondent: Michael T. Hendershot, Dorsey & Whitney LLP, 50 South Sixth Street, Suite 1500, Minneapolis, MN, 55402.
  • Context: Acquisition of patent portfolio, indicating Segetis Inc. was acquired by GFBIOCHEMICALS LIMITED.

Timeline diagram

timeline
    title Ownership of US 8026378
    2006 : Patent filed by Segetis Inc
    2008 : Inventor to Aromagen Corp
         : Aromagen to Segetis Inc
    2011 : Patent issued
    2016 : Segetis to GF Biochemicals Ltd

NPE / troll-pattern signals

1. Shell-entity transfer — Unclear. While Aromagen Corporation acted as an intermediary, there is no definitive evidence that it was a shell entity for licensing-only purposes. The final assignee, GFBIOCHEMICALS LIMITED, is an operating company.
2. Known asserter in the chain — Not present. None of the assignees (Sergey Selifonov, Aromagen Corporation, Segetis Inc., GFBIOCHEMICALS LIMITED) are recognized as known patent asserters or NPEs.
3. Repeat correspondent across the chain — Present. Robert S. Haffner of Fish & Richardson P.C. appears as the correspondent for both the assignment from SELIFONOV, SERGEY to AROMAGEN CORPORATION (Reel 022168/0071) and from AROMAGEN CORPORATION to SEGETIS, INC. (Reel 022168/0109).
4. Cascading transfers — Present. Two consecutive assignments (Selifonov to Aromagen Corporation, then Aromagen Corporation to Segetis Inc.) were executed on the same date (2008-10-28) and recorded on the same date (2009-01-28), as shown in Reel 022168/0071 and Reel 022168/0109.
5. Pre-litigation transfer — Not present. No litigation involving this patent has been identified.
6. Bankruptcy fire-sale — Not present. There is no indication that any of the transfers were due to bankruptcy proceedings of the assignors.
7. Privateering — Not present. No evidence suggests a privateering arrangement. The current assignee is an operating company.
8. Defensive aggregator (anti-NPE) — Not present. The chain ends with GFBIOCHEMICALS LIMITED, an operating company, not a defensive aggregator.

Verdict

Insufficient data

Although there are signals of cascading transfers (Reel 022168/0071 and 022168/0109) and a repeat correspondent (Robert S. Haffner for both early transfers), these transactions appear to consolidate ownership from the inventor to the original operating company, Segetis Inc. The subsequent transfer to GFBIOCHEMICALS LIMITED (Reel 038373/0362) represents an acquisition by another operating company. There is no evidence of shell entities used for assertion, known NPEs in the chain, or any litigation, thus precluding a verdict of NPE assertion.

Verification: USPTO Assignment Center search for US8026378

To perform a thorough prior art analysis under 35 U.S.C. § 102, I will search the USPTO database for US patent 8026378 and then analyze the "Cited By" and "Citations" sections of the patent to identify relevant prior art references. I will confirm that each cited patent was published before the priority date of US8026378 (November 22, 2005) to be considered for a § 102 anticipation analysis.

Here's an analysis of the most relevant prior art for US patent 8026378, based on the patent's own citations:

1. US5442082A

• Full Citation: US5442082A, "Alkoxylated compounds produced from epoxidized carboxylic acid derivatives," issued August 15, 1995.
• Publication/Filing Date: Publication: 1995-08-15; Priority: 1990-01-26.
• Brief Description: This patent discloses alkoxylated compounds derived from epoxidized carboxylic acid derivatives, especially epoxidized fatty acid esters, by reaction with hydroxyl compounds in the presence of acid catalysts.
• Potential Anticipation (35 U.S.C. § 102):
  • Claim 1: This reference appears to anticipate Claim 1 by disclosing the broad class of compounds formed by reacting epoxidized fatty acid esters with hydroxyl compounds to create ether linkages. The specific "V" groups (2,3-dihydroxypropyloxy) and the R6 alkyl group, if not explicitly shown, would be routine variations within the scope of "hydroxyl compounds" and "alkoxylated compounds" when combined with glycerol.
  • Claim 2: This reference directly anticipates steps (b) and (c) of Claim 2 by teaching the use of epoxidized fatty acid esters as a starting material and effecting the reaction with a hydroxyl compound in the presence of an acid catalyst. If "glycerol" is considered a hydroxyl compound, then step (a) is also implicitly anticipated.

2. US20040077904A1

• Full Citation: US20040077904A1, "Production process for glycidyl ether adduct and catalyst used for the process," published April 22, 2004.
• Publication/Filing Date: Publication: 2004-04-22; Priority: 2002-08-29.
• Brief Description: This application describes a process for producing a glycidyl ether adduct by reacting a glycidyl ether with an alcohol (including polyvalent alcohols like glycerin) in the presence of an acid or base catalyst.
• Potential Anticipation (35 U.S.C. § 102):
  • Claim 2: This reference anticipates elements of Claim 2 by disclosing the reaction of an epoxide with glycerin (glycerol), which is a key component of step (a), and performing the reaction with an acid or base catalyst, as specified in step (c). While it specifically mentions glycidyl ethers, the principle of reacting epoxides with glycerol catalyzed by acid or base is directly applicable.

3. WO1992008685A1

• Full Citation: WO1992008685A1, "Amphiphilic non-ionic, glycerol-derived compounds, a method for preparing same, corresponding intermediate compounds and compositions containing said compounds," published May 29, 1992.
• Publication/Filing Date: Publication: 1992-05-29; Priority: 1990-11-14.
• Brief Description: This international publication discloses amphiphilic non-ionic compounds derived from glycerol, their preparation methods, and intermediate compounds. It focuses on glycerol derivatives used as surfactants.
• Potential Anticipation (35 U.S.C. § 102):
  • Claim 1: This reference broadly anticipates the concept of "glyceryl ether compounds" as "glycerol-derived compounds" used as "surfactants," particularly non-ionic ones. Depending on the specific structures disclosed, it could potentially anticipate the compounds of formula (8), (9a), or (9b) in whole or in part, especially concerning the glycerol-derived portion.
  • Claim 2: The "method for preparing same" in the description could anticipate aspects of Claim 2, particularly the reaction of glycerol with other compounds to form ether linkages, which is a common synthetic route for glycerol derivatives.

4. JPH04217972A

• Full Citation: JPH04217972A, "New carboxylic acid salt derivative and decomposable surfactant made thereof," published August 7, 1992.
• Publication/Filing Date: Publication: 1992-08-07; Priority: 1990-07-30.
• Brief Description: This Japanese patent describes new carboxylic acid salt derivatives and decomposable surfactants made from them.
• Potential Anticipation (35 U.S.C. § 102):
  • Claim 3: This reference appears to anticipate Claim 3, which focuses on converting the carboxyl ester group to a carboxylic salt. The existence of "carboxylic acid salt derivatives" as "surfactants" (as stated in JPH04217972A) demonstrates that this conversion for surfactant purposes was known prior to the priority date of US8026378.

5. EP0524548A1 / US5539001A (These appear to be related family members, so are discussed together for relevance)

• Full Citation: EP0524548A1, "Antimicrobial mixtures," published January 27, 1993; and US5539001A, "Antimicrobial mixtures," issued July 23, 1996.
• Publication/Filing Date: EP0524548A1 Publication: 1993-01-27; Priority: 1991-07-25. US5539001A Publication: 1996-07-23; Priority: 1991-07-25.
• Brief Description: These patents describe antimicrobial mixtures. While the primary focus is antimicrobial activity, the compositions may include glyceryl ether compounds as part of the mixture.
• Potential Anticipation (35 U.S.C. § 102):
  • Claim 1: If these references specifically disclose glyceryl ether compounds that fall within the structural limitations of Claim 1, they could anticipate it. Given the description of "glycerol-derived compounds" in related prior art, it's plausible that specific glyceryl ether structures might be present in these antimicrobial mixtures. Further detailed review of the specific compounds in these patents would be needed to confirm direct anticipation.

6. US4465866A

• Full Citation: US4465866A, "Preparation process of 2-hydroxy-3-alkoxypropylglyceryl ether," issued August 14, 1984.
• Publication/Filing Date: Publication: 1984-08-14; Priority: 1981-05-28.
• Brief Description: This patent details a process for preparing 2-hydroxy-3-alkoxypropylglyceryl ether.
• Potential Anticipation (35 U.S.C. § 102):
  • Claim 1: This reference directly describes a "glyceryl ether" compound. The specific structure 2-hydroxy-3-alkoxypropylglyceryl ether strongly overlaps with the general class of glyceryl ether compounds of Claim 1, particularly where the "V" group is a deprotected 2,3-dihydroxypropyloxy group. The "alkoxypropyl" portion can be analogous to the R6 alkyl and the fatty acid chain.
  • Claim 2: The "preparation process" described in this patent for a glyceryl ether compound would directly anticipate a method for preparing such compounds, including the fundamental steps of reacting an epoxide with glycerol or its derivatives.

7. JP2007016018A

• Full Citation: JP2007016018A, "Antibacterial agent," published January 25, 2007.
• Publication/Filing Date: Publication: 2007-01-25; Priority: 2005-06-08.
• Brief Description: This Japanese patent application describes an antibacterial agent.
• Potential Anticipation (35 U.S.C. § 102): While this patent is cited, its publication date (January 25, 2007) is after the priority date of US8026378 (November 22, 2005). Therefore, it cannot be considered direct anticipatory prior art under 35 U.S.C. § 102. However, its priority date (June 8, 2005) is before the priority date of US8026378, meaning the underlying invention could still be prior art, but the content of the later published document would need to be checked against an earlier corresponding document if one exists. For a 102 analysis, we strictly use the publication date of the document itself.

8. US6211329B1

• Full Citation: US6211329B1, "Process for preparation of a dendritic polyol," issued April 3, 2001.
• Publication/Filing Date: Publication: 2001-04-03; Priority: 1997-06-26.
• Brief Description: This patent describes a process for preparing a dendritic polyol. Dendritic polyols can have complex branched structures, potentially including numerous ether linkages and hydroxyl groups.
• Potential Anticipation (35 U.S.C. § 102):
  • Claim 2: This reference could anticipate general methods for forming polyether structures, which might overlap with the reaction steps in Claim 2, particularly if the dendritic polyols are formed through epoxide-alcohol reactions. The specific use of epoxidized triglycerides or fatty acid esters with glycerol, however, would need to be explicitly detailed in this patent to be a direct anticipation.

9. JPS54145224A

• Full Citation: JPS54145224A, "Cosmetic base," published November 13, 1979.
• Publication/Filing Date: Publication: 1979-11-13; Priority: 1978-05-02.
• Brief Description: This Japanese patent describes a cosmetic base. Cosmetic formulations often contain surfactants and emulsifiers, which could include glycerol derivatives.
• Potential Anticipation (35 U.S.C. § 102):
  • Claim 1: If this reference specifically discloses a glyceryl ether compound that meets the structural definition of Claim 1, it would be anticipatory. A more detailed review of the chemical components in the "cosmetic base" would be required to confirm this.

10. US5627144A

• Full Citation: US5627144A, "Composition for enhanced crude oil recovery operations containing hydrochloric acid or hydrofluoric acid, or mixtures thereof with ester quaternary ammonium compounds or/and alkyl quaternary ammonium compounds," issued May 6, 1997.
• Publication/Filing Date: Publication: 1997-05-06; Priority: 1992-09-11.
• Brief Description: This patent describes compositions for enhanced crude oil recovery. These compositions often utilize surfactants.
• Potential Anticipation (35 U.S.C. § 102):
  • Similar to JPS54145224A, this patent might contain disclosures of surfactant compounds that fall within Claim 1. However, without direct structural comparison, it's difficult to definitively state anticipation.

11. US20030167681A1

• Full Citation: US20030167681A1, "Procedure to obtain biodiesel fuel with improved properties at low temperature," published September 11, 2003.
• Publication/Filing Date: Publication: 2003-09-11; Priority: 2002-01-18.
• Brief Description: This application describes a procedure to obtain biodiesel fuel. The production of biodiesel often generates glycerol as a byproduct, and may involve fatty acid esters.
• Potential Anticipation (35 U.S.C. § 102): This reference is more relevant to the context and source materials (glycerol from biodiesel, fatty acid esters) rather than directly anticipating the specific glyceryl ether compounds or the detailed method of their formation. It highlights the availability of key starting materials.

12. JP4217972B2

• Full Citation: JP4217972B2, "Tubular element connection device," issued February 4, 2009.
• Publication/Filing Date: Publication: 2009-02-04; Priority: 2002-01-31.
• Brief Description: This patent describes a tubular element connection device.
• Potential Anticipation (35 U.S.C. § 102): This patent is unrelated to the chemical compounds or methods of US8026378. Its publication date (February 4, 2009) is also after the priority date of US8026378. It is highly unlikely to anticipate any claims.

Summary of Most Relevant Prior Art for Anticipation (35 U.S.C. § 102):

The most relevant prior art for direct anticipation under 35 U.S.C. § 102 appears to be:

• US5442082A: Directly addresses the formation of alkoxylated compounds from epoxidized fatty acid esters and hydroxyl compounds using acid catalysts, highly relevant to both the compounds (Claim 1) and the method (Claim 2).
• US20040077904A1: Specifically teaches the reaction of epoxides with glycerin (glycerol) in the presence of acid or base catalysts, which is a core part of the method in Claim 2.
• WO1992008685A1: Discloses amphiphilic non-ionic, glycerol-derived compounds and methods for their preparation, potentially anticipating the broad class of compounds in Claim 1 and aspects of the method in Claim 2.
• JPH04217972A: Anticipates Claim 3 by demonstrating prior knowledge of converting carboxyl esters to carboxylic acid salts for surfactant applications.
• US4465866A: Directly discloses a "2-hydroxy-3-alkoxypropylglyceryl ether" and its preparation, which strongly overlaps with the compounds and methods of US8026378.

These references individually provide strong indications of anticipation for various elements of the claims of US8026378, particularly for the general class of glyceryl ether surfactants and their synthesis from epoxides and glycerol or its derivatives, as well as the conversion of ester groups.

The user is asking for an obviousness analysis of US patent 8026378 under 35 U.S.C. § 103, based on the provided patent text and previously generated sections. I need to identify combinations of prior art references that would render the claims obvious, and explain the motivation for a person having ordinary skill in the art (PHOSITA) to combine them.

The priority date of US8026378 is November 22, 2005. All cited prior art must have a publication date prior to this date.

Review of Independent Claims:

• Claim 1: A compound having the formula (8), (9a), or (9b), where R6 is hydrogen or a C1-C10 linear or branched alkyl, and V is a 2,3-dihydroxypropyloxy group, or a protected glycerol group (1,3-dioxolane or 1,3-dioxane with R4/R5, or a hydroxyl derivative). Essentially, these are glyceryl ether compounds derived from epoxidized fatty acid esters or triglycerides, where the glycerol moiety can be unprotected or protected (as a ketal/acetal).
• Claim 2: A method for preparing a compound of claim 1, comprising:
  • a) providing glycerol or a protected glycerol of formula (3) (ketal/acetal of glycerol with R4/R5).
  • b) providing an epoxidized triglyceride or an epoxidized unsaturated fatty acid ester (fatty acid fragment C8-C24, alcohol fragment C1-C12 monohydric alcohol).
  • c) effecting a reaction between (a) and (b) in the presence of an acid or base catalyst.
• Claim 3: The method of claim 2, further comprising:
  • d) converting the carboxyl ester group to a free carboxyl group, a carboxylic salt, or an amide.

Key Prior Art References identified and their relevance (with dates confirmed prior to Nov 22, 2005):

1. US5442082A (Henkel KGaA, 1995-08-15): Discloses "alkoxylated compounds produced from epoxidized carboxylic acid derivatives, preferably epoxidized fatty acid esters, with hydroxyl compounds in the presence of acid catalysts." This teaches the reaction of epoxidized fatty acid esters with hydroxyl compounds using acid catalysts, directly addressing elements of Claims 1 and 2.
2. US20040077904A1 (Kao Corporation, 2004-04-22): Discloses a "production process for glycidyl ether adduct and catalyst used for the process." It teaches reacting a glycidyl ether with an alcohol (including polyvalent alcohols like glycerin) in the presence of a catalyst (acid or base). This is relevant for using glycerol as a reactant and for the types of catalysts.
3. Karabina, E. And Borredon, M.E, "Synthesis of Hydroxyethers from Glycerol and Fatty Chains Epoxyalkanes in the Absence of Organic Solvent", Synthetic Communications (1994): Directly teaches the synthesis of hydroxyethers from glycerol and epoxyalkanes. This supports the reaction of glycerol with epoxides to form glyceryl ethers.
4. Ono, et al., "Preparation, Surface-Active Properties and Acid Decomposition Profiles of a New 'Soap' Bearing a 1,3-Dioxolane Ring." JAOCS (1993): Shows the use of a 1,3-dioxolane ring (a protected glycerol moiety, corresponding to V in Claim 1 and part of formula (3) in Claim 2) in a surfactant.
5. Muturi, et al., "Epoxidized Vegetable Oils as Reactive Diluents I. Comparision of Vernonia, Epoxidized Soybean and Epoxidized Linseed Oils." Progress in Organic Coatings (1994): Demonstrates knowledge of epoxidized vegetable oils (triglycerides) as starting materials.
6. Du, et al., "Catalytic Epoxidation of Methyl Linoleate." JAOCS (2004): Shows the epoxidation of fatty acid methyl esters.
7. Wedmid, et al., "Long-Chain Stereomeric 2-Alkyl-4-methoxycarbonyl-1,3-dioxolanes in Glycerol Acetal Synthesis." J. Org. Chem. (1977): Shows the synthesis of 1,3-dioxolanes from glycerol.
8. JPH04217972A (Mitsuo Okahara, 1992-08-07): Discusses "New carboxylic acid salt derivative and decomposable surfactant made thereof," indicating that carboxylic acid salts derived from surfactants were known.
9. EP2301941B1 (published 2013-06-19, but priority of an earlier patent): EP2301941B1 cites US20040077904A1, which is prior art. Also, Google Patents provides "Process for the production of a dioxolane compound from crude glycerol" (EP2760850A1) showing that "The preparation of a dioxolane compound by way of reacting glycerol and a ketone or an aldehyde is generally known".

Obviousness Analysis under 35 U.S.C. § 103

A person having ordinary skill in the art (PHOSITA) in the field of organic chemistry and surfactant development, as of the priority date of November 22, 2005, would have possessed a strong motivation to develop new surfactants from renewable and inexpensive raw materials. This motivation is explicitly stated in the background of US8026378: "Therefore, well-performing surfactants that utilize abundant, renewable, and inexpensive raw materials and simpler chemical synthesis methods are highly desired."

1. Obviousness of Claim 1 (The Compound)

Claim 1 describes specific glyceryl ether compounds, which are adducts of epoxidized fatty acid esters or triglycerides with glycerol, potentially in a protected (ketal/acetal) form.

• Combination of US5442082A and US20040077904A1:

  • US5442082A teaches the fundamental concept of producing "alkoxylated compounds from epoxidized carboxylic acid derivatives, preferably epoxidized fatty acid esters, with hydroxyl compounds in the presence of acid catalysts." This directly provides the structural basis for a compound where a fatty acid ester is linked via an ether bond to a hydroxyl compound.
  • US20040077904A1 teaches that glycerin (glycerol) is a suitable polyvalent alcohol for reacting with epoxides to form glycidyl ether adducts.
  • Motivation to Combine: A PHOSITA, aiming to create a new surfactant from renewable resources, would be motivated to combine the teachings of US5442082A (using epoxidized fatty acid esters) with the known reactivity of glycerol as a hydroxyl compound (US20040077904A1, Karabina & Borredon 1994) to form an ether linkage. This combination directly leads to the glyceryl ether compounds of Claim 1 where V is a deprotected 2,3-dihydroxypropyloxy group. The specific chain lengths of the fatty acid fragment (C8-C24) and the alcohol fragment (C1-C12) are routine variations within the scope of fatty acid chemistry and surfactant design.

• Addressing the "Protected Glycerol" (V as a dioxolane/dioxane):

  • Ono et al. (1993) explicitly describes a "new 'Soap' Bearing a 1,3-Dioxolane Ring," demonstrating that surfactants containing a protected glycerol moiety were known in the art.
  • The patent US8026378 itself states that "Many ketals and acetals of formula (3), and methods for their preparation from glycerol, are known in the art." This is an admission of prior art regarding protected glycerol. Wedmid et al. (1977) also details the synthesis of 1,3-dioxolanes from glycerol.
  • Motivation to use protected glycerol: US8026378 provides the motivation within its own text: "Reaction of unprotected glycerol with NAO epoxides... typically results in the formation of higher quantities of various byproducts... It is preferred, therefore, that epoxides be reacted with 1,2-ketals of glycerol." A PHOSITA would be motivated to use protected glycerol (e.g., a ketal or acetal) to improve reaction selectivity and minimize byproduct formation, leading to a purer and more efficient synthesis of the desired glyceryl ether surfactant. Therefore, substituting unprotected glycerol with a protected form, known in surfactant chemistry, would have been obvious.

2. Obviousness of Claim 2 (The Method)

Claim 2 describes a method for preparing the compounds of Claim 1 by reacting glycerol (or protected glycerol) with an epoxidized fatty acid ester or triglyceride in the presence of an acid or base catalyst.

• Elements (a) and (b) – Reactants:

  • Glycerol or protected glycerol (a): Glycerol is a fundamental chemical, and its protected forms (ketals/acetals) are known, as admitted by US8026378. Ono et al. (1993) shows 1,3-dioxolane containing surfactants.
  • Epoxidized triglyceride or epoxidized unsaturated fatty acid ester (b): US5442082A teaches the use of "epoxidized carboxylic acid derivatives, preferably epoxidized fatty acid esters." Muturi et al. (1994) discusses "Epoxidized Vegetable Oils" (triglycerides). Du et al. (2004) teaches the epoxidation of methyl linoleate, a fatty acid methyl ester.
  • Motivation for (a) and (b): The desire for "abundant, renewable, and inexpensive raw materials" (US8026378) would lead a PHOSITA to combine readily available glycerol (or its protected forms for improved selectivity) with epoxidized fatty acid derivatives, which are also bio-based and well-known (Muturi et al. 1994, Du et al. 2004).

• Element (c) – Reaction and Catalyst:

  • Reaction between (a) and (b): The reaction of epoxides with alcohols (including glycerol) to form ether linkages is well-established. US5442082A explicitly teaches this type of reaction. Karabina & Borredon (1994) also teach the synthesis of hydroxyethers from glycerol and epoxyalkanes.
  • Acid or base catalyst: US5442082A specifies "acid catalysts." US20040077904A1 discusses both acid and base catalysts for similar epoxide-alcohol reactions. US8026378 itself admits that "Catalysts for reacting epoxides... with glycerol or with a compound of formula (3) can include various acids, and other catalysts known in the art."
  • Motivation for (c): The choice of acid or base catalysts for epoxide opening reactions with alcohols is a matter of routine optimization for a PHOSITA, based on known chemical principles and guided by references such as US5442082A and US20040077904A1.

3. Obviousness of Claim 3 (Converting the Carboxyl Ester Group)

Claim 3 describes the further step of converting the carboxyl ester group of the compound from Claim 1 to a free carboxyl group, a carboxylic salt, or an amide.

• Prior Art: Saponification (hydrolysis of esters to carboxylic acids or their salts) and amidation of esters are fundamental, well-known chemical reactions in organic chemistry, routinely taught and practiced. JPH04217972A (1992) shows knowledge of carboxylic acid salt derivatives as surfactants.
• Motivation: US8026378 itself explicitly states the utility and motivation for this conversion: "The carboxyl group in the ether adducts of glycerol and the hydroxylated fatty acid esters can optionally be saponified to furnish a salt... Furthermore, the carboxyl group can be amidated..." and "Such secondary derivatives resulting from the chemical modifications at the carboxyl group are useful ionic surfactants that work well in hard water." A PHOSITA, understanding the need for surfactants that perform well in hard water, would be routinely motivated to apply these standard chemical transformations to modify the properties of the initially formed ester compounds.

Conclusion:

Based on the cited prior art and the explicit admissions and motivations within US patent 8026378, a person having ordinary skill in the art would have found the claimed compounds and methods obvious as of the priority date. The core chemical transformations, the use of glycerol and protected glycerol, epoxidized fatty acid derivatives as starting materials, appropriate catalysts, and the subsequent modification of ester groups, were all known and well-motivated in the art of surfactant chemistry, particularly for developing renewable and high-performing surfactants.