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US-12622847-B2 - Organosilicon compound and dental composition containing same

US12622847B2US 12622847 B2US12622847 B2US 12622847B2US-12622847-B2

Abstract

The present invention provides a dental composition that shows improved adhesive properties to dental restoration materials such as porcelain, as well as tooth structure, and that is suited for reducing property changes during storage. The present invention relates to a dental composition comprising an organosilicon compound (A) represented by the following general formula (1), Z—X m —Y—SiR 1 n R 2 (3-n) (1) wherein Z represents a (meth)acryloyloxy group, a (meth)acrylamide group, a mercapto group, or an epoxy group, X represents a divalent organic group with a ratio C/O of 1 to 3, where C is the total number of carbon atoms, and O is the total number of oxygen atoms, Y represents a divalent hydrocarbon group having 1 to 30 carbon atoms, R 1 represents a group selected from the group consisting of an alkyl group, an aryl group, and an aralkyl group, R 2 represents a hydroxyl group or a hydrolyzable group, m represents an integer of 1 to 8, and n represents 0, 1, or 2, and wherein R 1 , R 2 , and X each may be the same or different when R 1 , R 2 , or X is plural.

Inventors

  • Ryota MURAYAMA
  • Ryo Matsuura
  • Yamato Nojiri

Assignees

  • KURARAY NORITAKE DENTAL INC.

Dates

Publication Date
20260512
Application Date
20211224
Priority Date
20201225

Claims (18)

  1. 1 . A dental composition comprising an organosilicon compound (A) represented by the following general formula (1), Z—X m —Y—SiR 1 n R 2 (3-n) (1) wherein Z represents a (meth)acryloyloxy group, a (meth)acrylamide group, a mercapto group, or an epoxy group, X represents a divalent organic group with a ratio C/O of 1 to 3, where C is the total number of carbon atoms, and O is the total number of oxygen atoms, Y represents a divalent hydrocarbon group having 1 to 30 carbon atoms, R 1 represents a group selected from the group consisting of an alkyl group, an aryl group, and an aralkyl group, R 2 represents a hydroxyl group or a hydrolyzable group, m represents an integer of 1 to 8, and n represents 0, 1, or 2, and wherein R 1 , R 2 , and X each may be the same or different when R 1 , R 2 , or X is plural.
  2. 2 . The dental composition according to claim 1 , wherein the number of carbon atoms in X is 1 to 3.
  3. 3 . The dental composition according to claim 1 , wherein X is a group represented by the following formula (2), (3), or (4), —H 2 O— (2) —CH 2 CH 2 O— (3) —CH 2 CH 2 CH 2 O— (4).
  4. 4 . The dental composition according to claim 1 , wherein m is an integer of 1 to 4.
  5. 5 . The dental composition according to claim 1 , wherein n is 1 or 2.
  6. 6 . The dental composition according to claim 1 , wherein Z is a (meth)acryloyloxy group.
  7. 7 . The dental composition according to claim 1 , wherein R2 is an alkoxy group having 1 to 5 carbon atoms.
  8. 8 . The dental composition according to claim 1 , wherein the content of the organosilicon compound (A) is 0.1 to 50 mass %.
  9. 9 . The dental composition according to claim 1 , which further comprises a monomer (B) having an acidic group.
  10. 10 . The dental composition according to claim 9 , wherein the monomer (B) having an acidic group comprises a monomer having a phosphoric acid group.
  11. 11 . The dental composition according to claim 1 , which further comprises water (C).
  12. 12 . The dental composition according to claim 1 , which further comprises a monomer (D) having no acidic group.
  13. 13 . The dental composition according to claim 12 , wherein the monomer (D) having no acidic group comprises a hydrophilic monomer (D-2) having no acidic group.
  14. 14 . The dental composition according to claim 13 , which comprises 8 to 90 mass % of the hydrophilic monomer (D-2) having no acidic group based on the mass of all monomers contained in the dental composition.
  15. 15 . A dental adhesive comprising the dental composition of claim 1 .
  16. 16 . An organosilicon compound (A) represented by the following general formula (1), Z—X m —Y—SiR 1 n R 2 (3-n) (1) wherein Z represents a (meth)acryloyloxy group, a (meth)acrylamide group, a mercapto group, or an epoxy group, X represents a divalent organic group with a ratio C/O of 1 to 3, where C is the total number of carbon atoms, and O is the total number of oxygen atoms, Y represents a divalent hydrocarbon group having 1 to 30 carbon atoms, R 1 represents a group selected from the group consisting of an alkyl group, an aryl group, and an aralkyl group, R 2 represents a hydroxyl group or a hydrolyzable group, m represents an integer of 1 to 8, and n represents 0, 1, or 2, and wherein R 1 , R 2 , and X each may be the same or different when R 1 , R 2 , or X is plural.
  17. 17 . The organosilicon compound (A) according to claim 16 , wherein the number of carbon atoms in X is 1 to 3.
  18. 18 . The organosilicon compound (A) according to claim 16 , wherein X is a group represented by the following formula (2), (3), or (4), —CH 2 O— (2) —CH 2 CH 2 O— (3) —CH 2 CH 2 CH 2 O— (4).

Description

TECHNICAL FIELD The present invention relates to a novel organosilicon compound, and a dental composition containing same. BACKGROUND ART In response to the recent demand for dental restorations that not only offer functionality but also enhance aesthetics post-restoration, ceramic materials such as composite resins, zirconia, alumina, lithium disilicate glass, and porcelain have come to be used as dental restoration materials for crown restorations, alongside traditional metals. Dental primers and dental adhesives are used to bond such dental restoration materials to an adherend. Examples of dental primers and dental adhesives are disclosed. For example, Patent Literature 1 discloses a specific one-pack type dental primer comprising a silane coupling agent, an acidic group-containing polymerizable monomer, and a volatile organic solvent. Patent Literature 2 discloses a one-pack type adhesive composition that comprises a specific silane coupling agent, an acidic group-containing polymerizable monomer, a primary alcohol, and water, and in which the water content is 0.005 to 0.5 mass %. Over the years, there has been an increase in the versatility of dental compositions, and there is a growing need for a one-pack type dental composition that can be used as a single component on many adherends, including the tooth structure. However, because dental restoration materials such as porcelain greatly differ in material properties from tooth structure, it has been difficult to impart high adhesive properties to both of these materials. In view of such adhesive properties, the compositions described in Patent Literatures 1 and 2 need further improvements. Adding water is one possible method of improving adhesive properties to tooth structure. However, simply adding water results in a serious reduction in the preservation stability of a silane coupling agent, and decreases the adhesive properties to dental restoration materials. As a technique to overcome the foregoing issues, an example of a one-pack type dental composition that can be applied as a single component to a wide range of adherends, including both dental restoration materials and tooth structure, can be found in Patent Literature 3, which discloses a dental composition that comprises a specific silane coupling agent, an acidic group-containing polymerizable monomer, and water, and in which the water content is 1.0 to 50 mass %. CITATION LIST Patent Literature Patent Literature 1: WO2008/053990Patent Literature 2: JP 2008-1624 APatent Literature 3: WO2019/082855 SUMMARY OF INVENTION Technical Problem However, studies by the present inventors revealed that, aside from adhesive properties, the dental composition described in Patent Literature 3 undergoes a viscosity increase or shows a high degree of thixotropy during long storage, though the dental composition exhibits high adhesive properties to dental restoration materials such as porcelain, as well as tooth structure, as stated. Additionally, it was newly found that further improvements are needed in terms of ease of handling because the level of ease of handling immediately after production cannot last over an extended time period of long storage, making it difficult to dispense the dental composition from its container, or apply the dental composition in a layer over a surface of an adherend. That is, there is still room for improvement in terms of property stability during storage. It is accordingly an object of the present invention to provide a dental composition that shows improved adhesive properties to dental restoration materials such as porcelain, as well as tooth structure, and that is suited for reducing property changes during storage. Solution to Problem The present inventors conducted intensive studies to provide a solution to the foregoing issues, and found that a dental composition comprising an organosilicon compound having a specific structure shows improved adhesive properties to dental restoration materials such as porcelain, as well as tooth structure, and is suited for reducing property changes during storage. The present invention was completed after further studies based on this finding. Specifically, the present invention includes the following. [1] A dental composition comprising an organosilicon compound (A) represented by the following general formula (1), Z—Xm—Y—SiR1nR2(3-n)  (1) wherein Z represents a (meth)acryloyloxy group, a (meth)acrylamide group, a mercapto group, or an epoxy group, X represents a divalent organic group with a ratio C/O of 1 to 3, where C is the total number of carbon atoms, and O is the total number of oxygen atoms, Y represents a divalent hydrocarbon group having 1 to 30 carbon atoms, R1 represents a group selected from the group consisting of an alkyl group, an aryl group, and an aralkyl group, R2 represents a hydroxyl group or a hydrolyzable group, m represents an integer of 1 to 8, and n represents 0, 1, or 2, and wherein R1, R2, and X each may