Curable composition

• US 4,985,516 A
• Filed: 10/10/1989
• Issued: 01/15/1991
• Est. Priority Date: 10/30/1986
• Status: Expired due to Term

• Current Assignee: Mitsui Chemicals Incorporated (Mitsui Chemicals)
• Original Assignee: Mitsui Petrochemical Industries, Ltd.
• Inventors: Arata, Masami, Yamamoto, Takashi, Sakashita, Takeshi
• Primary Examiner(s): Schofer, Joseph L.
• Assistant Examiner(s): SAROFIM, NABIL F
• Application Number:
  US07/418,975
• Time in Patent Office: 462 Days
• Field of Search: 526/196
• US Class Current: 526/196
• CPC Class Codes: A61K 6/30 Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
• CPC Class Codes: A61K 6/76 comprising silicon-containing compounds
• CPC Class Codes: A61K 6/77 Glass
• CPC Class Codes: C08F 220/12 of monohydric alcohols or phenols
• CPC Class Codes: C08L 33/08 Homopolymers or copolymers of acrylic acid esters
• CPC Class Codes: C08L 33/10 Homopolymers or copolymers of methacrylic acid esters

Abstract

A curable composition effective for use for dental adhesive and exhibiting superior water-resistant bonding performance and high bonding strength onto enamel, dentine and dental alloys without imparting to dental pulp any irritative influence, which composition comprises

(A) a monofunctional monomer based on (meth)acrylate,

(B) a polyfunctional monomer based on (meth)acrylate,

(C) an acidic group-containing monomer based on (meth)acrylate having in the moleucle at least one (meth)acryloyloxyl group and

(D) a trialkylboron or its oxide.

Claims

1. A curable composition consisting essentially of:

(A) a monofunctional monomer based upon (meth)acrylate, in an amount of 5 to 95% by weight;

(B) a polyfunctional monomer based on (meth)acrylate in an amount of 95 to 5% by weight and said (meth)acrylate consists of one or more monomers selected from the group consisting of

(B₁) poly(meth)acrylates of alkane polyols,

(B₂) poly(meth)acrylates of (poly)oxyalkanepolyols.

(B₃) epoxy(meth)acrylates represented by the general formula (1) ##STR43## in which R₁ and R₂ represent each H or CH³ n is zero or a positive integer and R³ denotes a divalent aliphatic, cycloaliphatic or aromatic residue permissible or containing therein an oxygen or sulfur atom,

(B₄) cycloaliphatic or aromatic di(meth)acrylates represented by the general formula (II) ##STR44## in which R¹ and R² stand each for H or CH₃ and R³ denotes a divalent cycloaliphatic or aromatic residue having at least one cyclic group and permissible of containing therein an oxygen or sulfur atom and

(B₅) cycloaliphatic di(meth)acrylates represented by the general formula (III) ##STR45## in which R¹ and R² stand each for H or CH₃ and R³ denotes a divalent cycloaliphatic residue having at least one cyclic group and permissible of containing therein an oxygen or sulfur atom,

(B₆) polyfunctional monomers based on (meth)acrylate represented by the general formula (IV) ##STR46## in which R¹ and R² stand each for H or CH₃, R³ denotes a divalent aromatic residue having at least one aromatic ring and being permissible of containing therein an oxygen or sulfur atom and n and m stand each for a positive integer and

(B₇) polyfunctional monomers based on (meth)acrylate having in the molecule at least one urethane linkage

(C) an acidic group-containing monomer based on (meth)acrylate having in the molecule at least one (meth)acryloyloxyl group in an amount, on the weight basis, of from 1 to 50 parts per 100 parts of the sum of monomer (A)+(B); and

(D) a trialkylboron or its oxide in an amount, on the weight basis, of from 2 to 100 parts of the sum of monomers (A)+(B)+(C);

wherein, when cured, monofunctional layer (A) and polyfunctional monomer (B) compolymerize to produce a rigid, cross-linked, three-dimensional structure.

2. A curable composition according to claim 1, wherein the acidic group-containing monomer (C) based on (meth)acrylate consists of one or more monomers selected from the group consisting of

(C₁) aromatic polycarboxylic acids and anhydrides thereof having in the molecule at least one (meth)acryloyloxyl group and

(C₂) partial esters of phosphoric acid and esters of sulfonic acid each having in the molecule at least one (meth)acryloyloxyl group.

3. A curable composition according to claim 1, wherein the trialkylboron or its oxide (D) consists of one or more compounds selected from the group consisting of

triethylboron, tripropylboron, triisopropylboron, tri-n-butylboron, tri-n-amylboron, triisoamylboron, tri-sec-amylboron and oxidation products of them.

4. A curable composition according to claim 1, wherein the proportion of the components (A), (B), (C) and (D) in the composition is in the range of 5-95% by weight for (A), 95-5% by weight for (B) and 1-50 parts by weight for (C), based on the weight of the sum (A)+(B), and 2-100 parts by weight for (D), based on the weight of the sum (A)+(B)+(C).