Prior art

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.