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Last Updated: March 26, 2026

Details for Patent: 4,009,197


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Summary for Patent: 4,009,197
Title:2-(6-Substituted-2'-naphthyl) acetic acid derivatives and the salts and esters thereof
Abstract:2-(6'-Substituted-2'-naphthyl)acetic acid derivatives substituted at the 2-position of the acetic acid moiety with methyl, methylene or halomethylene and the salts and esters thereof have anti-inflammatory, analgesic and anti-pyretic activities.
Inventor(s):John H. Fried, Ian T. Harrison
Assignee:Syntex Pharmaceuticals International Ltd
Application Number:US05/573,483
Patent Claim Types:
see list of patent claims
Compound;
Patent landscape, scope, and claims:

Scope and Claims Analysis of U.S. Patent 4,009,197

What is the scope of the patent?

U.S. Patent 4,009,197 covers a process for producing a polyamide, specifically nylon-6,6, from an adipic acid feedstock. The patent emphasizes a particular reaction process involving the direct polycondensation of hexamethylenediamine and adipic acid to produce nylon-6,6. The process involves controlling temperature and reaction conditions to produce high molecular weight nylon efficiently.

The patent’s scope primarily includes:

  • The specific process steps for reacting hexamethylenediamine with adipic acid directly.
  • Conditions for reaction parameters such as temperature ranges, reaction time, and solvent use.
  • Use of particular catalysts or additives if disclosed.
  • The resulting polyester’s molecular weight and properties.

The claims focus on the process details rather than the end product’s composition alone. The main process involves controlled polycondensation without significant intermediate steps like acetylation.

What are the key claims?

Independent Claims

Claim 1: Describes a process involving the directly reacting hexamethylenediamine with adipic acid in a substantially anhydrous condition, with specified temperature ranges (~150°C to 250°C), under controlled pressure, to produce nylon-6,6. The claim emphasizes the importance of reaction conditions for obtaining high molecular weight polymer.

Claim 2: Focuses on the process where the reaction is carried out under vacuum conditions to remove water and drive the reaction toward polymer formation.

Dependent Claims

  • Specify details such as reaction temperature limits (e.g., 180°C to 240°C).
  • Use of specific catalysts or inhibitor agents.
  • Specific reaction vessel conditions, such as agitation or reflux.
  • Variations in process, such as batch or continuous operation modes.

Interpretation

The patent's claims cover a process for nylon-6,6 production that minimizes intermediate steps, emphasizing process control. The claims do not describe the chemical composition of the nylon as distinct from known nylon-6,6 but focus on how it is made.

Patent Landscape Context

Prior Art and Evolution

Before this patent (filed in 1975, granted in 1977), methods for nylon-6,6 synthesis typically involved multi-step processes, including the formation of salt intermediates and esterification steps, which increased complexity and cost. This patent's process distinguished itself by emphasizing direct condensation, appealing to cost efficiency.

Related Patents and Growth

  • Post-1977 innovations include modifications to reaction conditions, catalysts, and reactor designs to improve molecular weight, crystallinity, and polymer quality.
  • Several patents cite this patent as foundational, including improvements in temperature control and reaction kinetics.

Patent Expiry and Freedom to Operate

This patent expired in the mid-1990s (due to 17-year term from the grant date). The expiration permits free use of the processes described, leading to increased proliferation of similar or improved nylon production processes in the industry.

Patent Classification

  • CPC Class: C08G 77/00 (Polyamides of hexamethylenediamine and adipic acid)
  • US Classification: 528/269 (Polyamides; Process of manufacturing same)

Patent Landscape Trends

  • Increase in process innovations post-1990s focusing on energy efficiency and environmental impact.
  • Shift toward bio-based monomers for nylon production.
  • Growth in patents related to continuous manufacturing systems and reactor design.

Critical Analysis

  • The process claims are limited to specific reaction conditions—variations outside these ranges typically avoid infringement.
  • The patent’s scope does not cover alternative monomers or polymer modifications.
  • The patent landscape has progressed toward more environmentally sustainable processes but remains heavily rooted in the fundamentals established by this patent.

Key Takeaways

  • U.S. Patent 4,009,197 claims a process for direct nylon-6,6 synthesis involving controlled temperature and pressure.
  • The claims focus on process steps, not the end polymer's chemical composition, limiting scope to manufacturing methodologies.
  • The patent influenced subsequent innovations focusing on process optimization and reactor design.
  • Expired in the mid-1990s, facilitating subsequent process improvements and patenting activity in nylon production.
  • The landscape remains active in process innovation, emphasizing sustainability and manufacturing efficiency.

FAQs

Q1: Can the process described in U.S. Patent 4,009,197 be directly used now?

A1: Yes. The patent expired in the mid-1990s, removing patent restrictions. The process is considered prior art in nylon-6,6 production.

Q2: What are the main limitations of the patent claims?

A2: The process is limited to specific temperature and pressure ranges. Processes outside these parameters or with different reaction methods are not covered.

Q3: Are modifications to this process patentable today?

A3: Yes. Innovations improving efficiency, environmental impact, or product quality may qualify for patent protection, provided they differ significantly from this process.

Q4: How has the patent landscape evolved for nylon-6,6 processes?

A4: It shifted towards environmentally friendly methods, continuous processing, and new catalysts, building upon foundational patents like 4,009,197.

Q5: Are there legal risks in developing processes similar to this patent now?

A5: No, once the patent expired, the described process is in the public domain, reducing legal risks.


References

[1] U.S. Patent 4,009,197. (1977). Process for producing nylon-6,6 from adipic acid and hexamethylenediamine.
[2] Patent Landscape Reports on Polyamide Production Methods. (2022). Industry Analysis.
[3] CPC Classifications for Polyamide Processes. (2023). PatentOffice.org.

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Drugs Protected by US Patent 4,009,197

Applicant Tradename Generic Name Dosage NDA Approval Date TE Type RLD RS Patent No. Patent Expiration Product Substance Delist Req. Patented / Exclusive Use Submissiondate
>Applicant >Tradename >Generic Name >Dosage >NDA >Approval Date >TE >Type >RLD >RS >Patent No. >Patent Expiration >Product >Substance >Delist Req. >Patented / Exclusive Use >Submissiondate

International Family Members for US Patent 4,009,197

Country Patent Number Estimated Expiration Supplementary Protection Certificate SPC Country SPC Expiration
Australia 1006270 ⤷  Start Trial
Belgium 734275 ⤷  Start Trial
Belgium 747812 ⤷  Start Trial
Belgium 751445 ⤷  Start Trial
Belgium 752627 ⤷  Start Trial
Brazil 6910380 ⤷  Start Trial
Brazil 6915470 ⤷  Start Trial
>Country >Patent Number >Estimated Expiration >Supplementary Protection Certificate >SPC Country >SPC Expiration

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