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EP-3861977-B1 - (METH)ACRYLATE, MONOMER COMPOSITION, MOLDED BODY, COMPOSITION FOR DENTAL MATERIAL, AND DENTAL MATERIAL

EP3861977B1EP 3861977 B1EP3861977 B1EP 3861977B1EP-3861977-B1

Inventors

  • KAKINUMA, Naoyuki

Dates

Publication Date
20260506
Application Date
20191211

Claims (8)

  1. A (meth)acrylate being a compound (X) having a structure formed by a reaction of an epoxy compound (A) containing an epoxy group and a tertiary carbon atom or a quaternary carbon atom, a (meth)acrylic acid (B), and an iso(thio)cyanate compound (C) having two or more iso(thio)cyanate groups, wherein the epoxy compound (A) comprises a tert-butyl group, a tert-pentyl group, a tert-hexyl group, a tert-heptyl group, a tert-octyl group, a tert-decyl group or a cumyl group, wherein the epoxy compound (A) comprises a glycidyl ether group that is a functional group containing the epoxy group, wherein the iso(thio)cyanate compound (C) is at least one kind of iso(thio)cyanate compound selected by the group consisting of pentamethylene diisocyanate, m-xylylene diisocyanate, 1,3-tetramethylxylylene diisocyanate, isophorone diisocyanate, bis(isocyanatemethyl)cyclohexane, 2,5-bis(isocyanatemethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatemethyl)bicyclo-[2.2.1]-heptane, tolylene diisocyanate, phenylene diisocyanate, and 4,4'-diphenylmethane diisocyanate, and wherein the (meth)acrylate is represented by the following general formula (1): wherein, in general formula (1), R 1 represents a residue of the epoxy compound (A) from which the glycidyl ether group has been removed; R 2 represents a residue of the iso(thio)cyanate compound (C) from which all iso(thio)cyanate groups have been removed; R 3 represents a hydrogen atom or a methyl group; R 4 represents an oxygen atom or a sulfur atom; n is an integer of 2 or more; and plural instances of R 1 , R 3 and R 4 may be the same or different, respectively.
  2. The (meth)acrylate according to claim 1, wherein the compound (X) is a reaction product of a reactant of the epoxy compound (A) and the (meth)acrylic acid (B), and the iso(thio)cyanate compound (C).
  3. The (meth)acrylate according to claim 1 or claim 2, wherein a molecular weight of the R 1 is from 50 to 300 in general formula (1).
  4. The (meth)acrylate according to any one of claims 1 to 3, wherein R 1 is a group represented by the following formula (2), (3), (4), (5), (6), (7), (8), (9) or (10) in general formula (1): wherein, in formulae (2)-(10), each wavy line represents a binding site.
  5. A monomer composition comprising a (meth)acrylate (D) that is the (meth)acrylate according to any one of claims 1 to 4.
  6. A molded body comprising a cured product of the (meth)acrylate according to any one of claims 1 to 4 or a cured product of the monomer composition according to claim 5.
  7. A composition for a dental material comprising the (meth)acrylate according to any one of claims 1 to 4 or the monomer composition according to claim 5, a polymerization initiator, and a filler.
  8. A dental material comprising a cured product of the composition for a dental material according to claim 7.

Description

Technical Field The present invention relates to a (meth)acrylate, a monomer composition, a molded body, a composition for a dental material, and a dental material. Conventionally, polymerizable monomers represented by (meth)acrylates are widely used in various fields such as paints, printing plates, optical materials, and dental materials by utilizing their properties such as good curability and transparency. In the field of dental materials, polymerizable monomers are widely used in dental restorative materials such as dental composite resins used for repairing dental caries and fractures of natural teeth, various dental adhesives used to bond dental composite resins to teeth, as well as artificial teeth and denture base materials. Dental composite resins are generally composed of a polymerizable monomer, a polymerization initiator and a filler, and from the viewpoint of in-vivo safety, mechanical strength of a cured product, abrasion resistance, aesthetics, radical-polymerizable polyfunctional (meth)acrylates are used. As radical-polymerizable polyfunctional (meth)acrylates, 2,2-bis[4-(3-methacryloyloxy-2-hydroxypropoxy)phenyl]propane (commonly known as Bis-GMA), and 2,2,4-trimethylhexamethylenebis(2-carbamoyloxyethyl)dimethacrylate (commonly known as UDMA) are used. However, regarding dental composite resins, it has been pointed out that there is much room for improvement in reducing polymerization shrinkage during curing. It is desired to reduce polymerization shrinkage since it causes a contraction gap caused by the dental composite resin peeling off from the adhesive surface and causes secondary caries, tooth pulp stimulation, coloring, and restoration material falling. In order to reduce polymerization shrinkage, it is generally proposed to use a ring-opening polymerizable epoxy compound or an oxetane compound with less polymerization shrinkage than an acrylic compound (for example, see Patent Literature 1 and Patent Literature 2). EP 2711381 A1 and US 2010/307378 A1 are also dealing with polymerization shrinkage of acrylic compounds. Further, it is also proposed to increase the filling amount of filler and to reduce polymerization shrinkage (for example, see Patent Literature 3 and Patent Literature 4). [Patent Literature 1] Japanese National-Phase Publication (JP-A) No. 2007-15946[Patent Literature 2] JP-A No. 2005-187385[Patent Literature 3] JP-A No. 2007-526270[Patent Literature 4] JP-A No. 2005-89312 SUMMARY OF INVENTION Technical Problem In Patent Literature 1 and Patent Literature 2, polymerization shrinkage tends to be reduced by using these compounds, but there are many problems such as the need for a dedicated primer since the curing system is different. Further, in Patent Literature 3 and Patent Literature 4, since the shrinkage rate of the monomer used is high, the effect is limited. Further, as the (meth) acrylate used for a dental composite resin or the like, it is desirable that mechanical strength such as breaking strength can be increased when it is made into a cured product. One aspect of the present invention is made in view of the above problem, and an object thereof is to provide a (meth)acrylate capable of manufacturing a cured product with excellent breaking strength, and less polymerization shrinkage during curing, a monomer composition containing thereof, a molded body including a cured product of this monomer composition, a composition for a dental material containing this monomer composition, and a dental material including a cured product of this composition for a dental material. Solution to Problem Examples of the means for solving the above problem are shown below. A (meth)acrylate being a compound (X) having a structure formed by a reaction of an epoxy compound (A) containing an epoxy group and a tertiary carbon atom or a quaternary carbon atom, a (meth)acrylic acid (B), and an iso(thio)cyanate compound (C) having two or more iso(thio)cyanate groups, wherein the epoxy compound (A) comprises a tert-butyl group, a tert-pentyl group, a tert-hexyl group, a tert-heptyl group, a tert-octyl group, a tert-decyl group or a cumyl group,wherein the epoxy compound (A) comprises a glycidyl ether group that is a functional group containing the epoxy group,wherein the iso(thio)cyanate compound (C) is at least one kind of iso(thio)cyanate compound selected by the group consisting of pentamethylene diisocyanate, m-xylylene diisocyanate, 1,3-tetramethylxylylene diisocyanate, isophorone diisocyanate, bis(isocyanatemethyl)cyclohexane, 2,5-bis(isocyanatemethyl)bicyclo-[2.2.1]-heptane, 2,6-bis(isocyanatemethyl)bicyclo-[2.2.1]-heptane, tolylene diisocyanate, phenylene diisocyanate, and 4,4'-diphenylmethane diisocyanate, andwherein the (meth)acrylate is represented by the following general formula (1): Wherein, in general formula (1), R1 represents a residue of the epoxy compound (A) from which the glycidyl ether group has been removed; R2 represents a residue of the iso(thio)cyanate compoun