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KR-20260066169-A - copolymer of N-vinylpyrrolidone having a functionalized maleic acid moiety

KR20260066169AKR 20260066169 AKR20260066169 AKR 20260066169AKR-20260066169-A

Abstract

The present invention relates to a vinylpyrrolidone copolymer of N- vinylpyrrolidone and a maleic acid comonomer, wherein the vinylpyrrolidone copolymer is functionalized with a benzophenone substituent ( BP ), and the maleic acid content in the vinylpyrrolidone copolymer is less than 1 mol%, preferably 0.1 to 0.95 mol%, more preferably 0.1 to 0.90 mol%, more preferably 0.1 to 0.85 mol%, more preferably 0.2 to 0.88 mol%, more preferably 0.3 to 0.88 mol%, more preferably 0.4 to 0.88 mol%, even more preferably 0.5 to 0.85 mol%, and most preferably 0.5 to 0.875 mol%. The vinylpyrrolidone copolymer of the present invention is particularly suitable for use in coatings of medical devices and/or medical assistive devices. Accordingly, the present invention relates to a medical device having a composition comprising a vinylpyrrolidone copolymer and optionally a crosslinking agent, as well as a coating having a crosslinked vinylpyrrolidone copolymer and optionally a crosslinking agent.

Inventors

  • 호프만 미하엘
  • 호프만 에리카
  • 비머 카타리나
  • 호르바흐 헬무트

Assignees

  • 프로이덴베르크 메디컬 헤모텍 게엠베하

Dates

Publication Date
20260512
Application Date
20240917
Priority Date
20230917

Claims (20)

  1. Vinylpyrrolidone copolymer of the following general chemical formula ( P1 ): In the above formula m = 0.1 - 0.9 mol%; and n = 100 mol% - m ; X 1 and X 2 are independently selected from -O- and -NH-; The p% of R' and R'' are selected independently of each other from -L' - BP' and -L'' - BP'' ; and Up to p% of R' and R'' are independently selected from -( CH₂CH₂O ) q - H, polylactide, polyglycolide, polyacrylate, alkyl, aryl, arylalkyl, alkoxy, aryloxy, alkylhydroxy, arylhydroxy, alkylaryloxy, alkylamino, arylamino, alkylarylamino, silyl groups and organometallic groups; and the remaining residues R ' and R '' are -H; R ''' and R'''' independently represent -H, -CH3 , -CH2CH3 , or -F; L' and L'' are independently combined and selected from -CH 2- ; BP' or BP'' are independent of each other Representing; R B1a - R B4a and R B1b - R B5b are independently -H, -COOH, -CH 3 , -F, -Cl, -Br, -I, -OH, -CN, -N 3 , -OCN, -NCO, -SCN, -NCS, -CHO, -COCN, -NHCONH 2 , -NHC(=NH)NH 2 , -OCONH 2 , -NO 2 , -COCH 3 , -CONH 2 , -SO 3 H, -SO 2 NH 2 , -OCH 3 , -OC 2 H 5 , -OC 3 H 7, -OCF 3 , -OCH(CH 3 ) 2 , -OC(CH 3 ) 3 , -OC 4 H 9 , -O -cyclo -C3H5 , -OCH2 -cyclo -C3H5 , -OC2H4 -cyclo -C3H5 , -OCH 2 CH(CH 3 ) 2 , -OC 2 H 4 OCH 3 , -CH 2 OCH 3 , -CF 3, -C 2 H 5 , -C 3 H 7 , -NH 2 , -NH(CH) 3 , -N(CH 3 ) 2 , or -SOCH 3 ; p is a number from 1 to 50, and q is an integer between 5 and 900.
  2. In Article 1, A vinylpyrrolidone copolymer in which only one of X 1 and X 2 in the above formula is -NH-.
  3. In Paragraph 1 or Paragraph 2, A vinylpyrrolidone copolymer in which R''' and R'''' represent -H in the above formula.
  4. In any one of paragraphs 1 to 3, A vinylpyrrolidone copolymer in which m = 0.1 - 0.85 mol% in the above formula.
  5. In any one of paragraphs 1 to 4, A vinylpyrrolidone copolymer in which m = 0.5 - 0.75 mol% in the above formula.
  6. In any one of paragraphs 1 to 5, A vinylpyrrolidone copolymer in which m = 0.5 - 0.875 mol% or 0.5 - 0.88 mol% in the above formula.
  7. In any one of paragraphs 1 to 6, In the above formula, R' and R'' are independently - L' - BP' , -(CH 2 CH 2 O) q -OH, or A vinylpyrrolidone copolymer in which -H is represented; and at least one of R' and R'' in the above formula is -L' - BP' .
  8. In any one of paragraphs 1 through 7, A vinylpyrrolidone copolymer in which, in the above formula, q is an integer between 5 and 50, preferably q is an integer between 35 and 50.
  9. In any one of paragraphs 1 through 8, In the above formula, R B1a - R B4a and R B1b - R B5b is a vinylpyrrolidone copolymer representing -H.
  10. In any one of paragraphs 1 through 9, A vinylpyrrolidone copolymer in which one of R' and R'' in the above formula represents - L' - BP' , and the other represents -(CH 2 CH 2 O) q -OH, or -H.
  11. In any one of paragraphs 1 through 10, A vinylpyrrolidone copolymer in which one of R' and R'' represents -L' - BP' and the other represents -H in the above formula.
  12. In any one of paragraphs 1 through 11, A vinylpyrrolidone copolymer in which one of R' and R'' in the above formula represents -L' - BP' , and the other represents -( CH2CH2O ) q -OH.
  13. In any one of paragraphs 1 through 12, A vinylpyrrolidone copolymer in which L' and L'' are bonds in the above formula.
  14. In any one of paragraphs 1 through 12, A vinylpyrrolidone copolymer in which L' and L'' in the above formula are -CH2- .
  15. In any one of paragraphs 1 through 14, A vinylpyrrolidone copolymer in which p is 50 in the above formula.
  16. In any one of paragraphs 1 through 14, A vinylpyrrolidone copolymer in which p is 25 in the above formula.
  17. In any one of paragraphs 1 through 15, A vinylpyrrolidone copolymer in which p is 50 in the above formula, and 50% of R ' and R '' in the above formula are -( CH2CH2O ) q -H.
  18. In any one of paragraphs 1 through 15, A vinylpyrrolidone copolymer in which p is 50 in the above formula, and the remaining residues R ' and R '' are -H.
  19. In any one of paragraphs 1 through 16, A vinylpyrrolidone copolymer in which p is 25 in the above formula, and 25% of R ' and R '' in the above formula are - (CH2CH2O ) q -H, and the remaining residues R ' and R '' are -H.
  20. Vinylpyronidone copolymer selected from the group consisting of the following compounds: , and , In the above formula m = 0.1 - 0.9 mol%; n = 100 mol% - m; q is an integer between 35 and 50.

Description

copolymer of N-vinylpyrrolidone having a functionalized maleic acid moiety The present invention relates to a vinylpyrrolidone copolymer of N- vinylpyrrolidone and a maleic acid comonomer, wherein the vinylpyrrolidone copolymer is functionalized with a benzophenone substituent ( BP ), and the maleic acid content in the vinylpyrrolidone copolymer is less than 1 mol%, preferably 0.1 to 0.95 mol%, more preferably 0.1 to 0.90 mol%, more preferably 0.1 to 0.85 mol%, more preferably 0.2 to 0.88 mol%, more preferably 0.3 to 0.88 mol%, more preferably 0.4 to 0.88 mol%, even more preferably 0.5 to 0.85 mol%, and most preferably 0.5 to 0.875 mol%. The vinylpyrrolidone copolymer of the present invention is particularly suitable for use in coatings of medical devices and/or medical assistive devices. Accordingly, the present invention relates to medical devices and medical assistive devices having a cross-linked vinylpyrrolidone copolymer and optionally a coating of at least one crosslinking agent according to the present invention, as well as cosmetics and sanitary products comprising a polymer according to the present invention and optionally at least one crosslinking agent according to the present invention. In general, since medical devices inevitably come into contact with living organisms during use, all medical treatments on the body entail potentially life-threatening situations, and because the body naturally responds to these through its own protective mechanisms, a very high level of safety and security is required. Therefore, medically necessary procedures must be performed in a manner that minimizes traumatic outcomes and reduces them to an unavoidable level. Furthermore, the post-procedure recovery process must be managed to prevent treatment-related complications in the short or long term. Accordingly, medical devices must possess sufficient stability, biocompatibility, blood compatibility, hydrophilicity, flexibility, biodegradability, pressure resistance, tolerance, or suitability to prevent undesirable outcomes such as degenerative inflammatory processes, infection, thrombosis, hemorrhage, tissue proliferation, cell loss, necrosis, scar formation, arthritis, bone proliferation, bone loss, cartilage damage, cartilage loss, and connective tissue damage. A key factor in preventing complications—in addition to using the gentlest possible surgical techniques—is that medical devices must be easy to handle and function optimally without causing unnecessary short-term or long-term damage. For example, the surface of a medical device must not be rough to avoid intentionally rubbing, damaging, or irritating surrounding tissues when in contact with them. Rough surfaces can unintentionally exacerbate inflammatory processes, making the healing process more difficult or even hindering healing itself. Degenerative inflammatory processes, overreactions of tissue, immune, and coagulation systems, infections, thrombosis, bleeding, and tissue proliferation can be caused by the presence of a medical device as a foreign object, and serious damage can result if the device fails to perform its function properly, causing persistent and permanent pain or sequelae (e.g., skeletal areas, bandages, etc.). Therefore, medical devices that fail to perform their proper function and cause persistent and permanent pain or sequelae (e.g., skeletal areas, intervertebral discs, joints, spine, arthritis, osteoproliferation, osteonecrosis, cartilage damage, cartilage loss) must be avoided. Existing technologies have long strived to solve these complex problems by utilizing various materials. The core objective here is to minimize tissue damage or irritation, prevent the inevitable inflammatory process caused by the procedure from worsening, and promote the healing process rather than delaying it, thereby maximizing the original functions of medical or assistive devices. To date, existing medical devices capable of meeting these desirable characteristics are extremely rare. This is particularly evident in the vascular field. In the vascular sector, hydrophilic materials are primarily used for coatings on devices such as stents and catheters. These products are advertised as improving implantation conditions over the long term due to their low-friction, high-adhesion coatings. Despite possessing improved characteristics, these products still fail to fully meet the high standards required for them. However, preventing inflammation and infection is critical not only in the vascular field but also for catheters requiring long-term use, such as those in the urinary tract, or for cases requiring access over short or long periods (including drip infusion, mechanical ventilation via tracheostomy, artificial ostomy, and all types of cannulas). Therefore, the requirements for medical devices or assistive medical devices vary depending on the application area. Therefore, there is still an urgent need for medical devices or medical assistive devices wi