Bulky monomers leading to resins exhibiting low polymerization shrinkage

• US 20050124721A1
• Filed: 09/08/2004
• Published: 06/09/2005
• Est. Priority Date: 12/03/2003
• Status: Abandoned Application

• Current Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: Arthur, Samuel David, Brandenburg, Charles J.
• Application Number:
  US10/936,106
• Publication Number:
  US 20050124721A1
• Time in Patent Office: Days
• US Class Current: 523/115
• CPC Class Codes: C07C 2603/94 containing "free" spiro atoms
• CPC Class Codes: C07C 271/16 to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
• CPC Class Codes: C07C 69/54 Acrylic acid esters; Methacrylic acid esters

Abstract

The invention relates to a dental composite material wherein space-filling compounds are utilized to reduce shrinkage upon polymerization; the invention also relates to a method for producing dental restoration articles with reduced shrinkage; the invention also relates to various dental restorative articles comprising the aforementioned space-filling compounds.

Claims

1. A compound of the formula

10. A dental composite material comprising the compound as in any of claims 1-9.

20. A dental filling comprising the compound as in any of claims 1-9.

21. A dental inlay, onlay, facing, or laminate veneer comprising the compound as in any of claims 1-9.

22. A dental crown, bridge, or orthodontic splint material comprising the compound as in any of claims 1-9.

23. A dental adhesive, cement, sealant, or an adhesive for orthodontic appliances comprising the compound as in any of claims 1-9.

24. An artificial tooth, denture base, or denture reline material comprising the compound as in any of claims 1-9.

25. A method of treating dental tissue with a direct composite, comprising the steps of:

(a) placing a dental composite material comprising the compound as in any of claims 1-9 on a dental tissue;

(b) curing the dental composite material; and

(c) shaping the dental composite material.

2. A compound of the formula

3. A compound of the formula

4. A compound of the formula

5. A compound of the formula

6. A compound of the formula

7. A compound of the formula

8. A compound of the formula

9. A compound of the formula

11. A dental composite material comprising:

(a) at least one (meth)acrylic ester compound,

(b) at least one polymerization initiator compound,

(c) at least one inorganic filler, and

(d) at least one space-filling compound comprising at least one of

(e)

wherein

R₁ and R₂ are independently acryloyl;

methacryloyl;

2-acryloyloxyethyl;

2-methacryloyloxyethyl;

2-acryloyloxypropyl;

2-methacryloyloxypropyl;

2-(carbonylamino)ethyl acrylate;

2-(carbonylamino)ethyl methacrylate;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

or 2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate;

R₃ and R₄ are independently H, CH₃, alkyl, or aralkyl such that the carbon atom attached to the cyclopentane ring is aliphatic with at least one H; and

R₅ and R₆ are independently H, CH₃, alkyl or aralkyl, containing one carbon less than R₃ and R₄ respectively;

provided when R₃ and R₄ are CH₃ and R₅ and R₆ are H that R₁ and R₂ are independently 2-(carbonylamino)ethyl acrylate;

2-(carbonylamino)ethyl methacrylate;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

or 2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate;

wherein

R₇ and R₈ are independently 2-acryloyloxyethyl;

2-methacryloyloxyethyl;

2-acryloyloxypropyl;

2-methacryloyloxypropyl;

3-acryloyloxy-2,2-dimethylpropyl;

3-methacryloyloxy-2,2-dimethylpropyl;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[3-(2,2-dimethylpropoxy)carbonylamino]ethyl acrylate;

2-[3-(2,2-dimethylpropoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

or 2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate;

R₉ and R₁₀ are independently H, CH₃, alkyl, or aralkyl such that the carbon atom attached to the cyclopentane ring is aliphatic with at least one H;

R₁₁ and R₁₂ are independently H, CH₃, alkyl, or aralkyl, containing one carbon less than R₉ and R₁₀ respectively;

wherein

R₁₃ and R₁₄ are independently 2-acryloyloxyethyl;

2-methacryloyloxyethyl;

2-acryloyloxypropyl;

2-methacryloyloxypropyl;

3-acryloyloxy-2,2-dimethylpropyl;

3-methacryloyloxy-2,2-dimethylpropyl;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[3-(2,2-dimethylpropoxy)carbonylamino]ethyl acrylate;

2-[3-(2,2-dimethylpropoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

or 2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate;

R₁₅, R₁₆, and R₁₇ are independently H, CH₃, alkyl, or aralkyl such that the carbon atom attached to the cyclopentane ring is aliphatic with at least one H;

R₁₈ is H, CH₃, alkyl, or aralkyl, containing one carbon less than R₁₅, R₁₆, or R₁₇;

wherein

R₁₉ and R₂₀ are independently acryloyl;

methacryloyl;

2-acryloyloxyethyl;

2-methacryloyloxyethyl;

2-acryloyloxypropyl;

2-methacryloyloxypropyl;

2-(carbonylamino)ethyl acrylate;

2-(carbonylamino)ethyl methacrylate;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

or 2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate;

R₂₁, R₂₂, and R₂₃ are independently H, CH₃, alkyl, or aralkyl;

wherein

R₂₄ and R₂₅ are independently acryloyl;

methacryloyl;

2-acryloyloxyethyl;

2-methacryloyloxyethyl;

2-acryloyloxypropyl;

2-methacryloyloxypropyl;

2-(carbonylamino)ethyl acrylate;

2-(carbonylamino)ethyl methacrylate;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

or 2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate;

R₂₆ and R₂₇ are independently H, CH₃, alkyl, or aralkyl;

provided when R₂₆ and R₂₇ are H that R₂₄ and R₂₅ are independently 2-(carbonylamino)ethyl acrylate;

2-(carbonylamino)ethyl methacrylate;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

or 2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate;

wherein

R₂₈ and R₂₉ are independently acryloyl;

methacryloyl;

2-acryloyloxyethyl;

2-methacryloyloxyethyl;

2-acryloyloxypropyl;

2-methacryloyloxypropyl;

2-(carbonylamino)ethyl acrylate;

2-(carbonylamino)ethyl methacrylate;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

or 2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate;

R₃₀ and R₃₁ are independently H, CH₃, alkyl, or aralkyl;

provided when R₃₀ and R₃₁ are H or CH₃ that R₂₈ and R₂₉ are independently 2-(carbonylamino)ethyl acrylate;

2-(carbonylamino)ethyl methacrylate;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

or 2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate;

2-(carbonylamino)ethyl acrylate;

2-(carbonylamino)ethyl methacrylate;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

or 2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate;

wherein R₃₄ and R₃₅ are independently 2-acryloyloxyethyl;

2-methacryloyloxyethyl;

2-acryloyloxypropyl;

2-methacryloyloxypropyl;

2-(carbonylamino)ethyl acrylate;

2-(carbonylamino)ethyl methacrylate;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

or 2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate; and

wherein R₃₆ and R₃₇ are independently 2-acryloyloxyethyl;

2-methacryloyloxyethyl;

2-acryloyloxypropyl;

2-methacryloyloxypropyl;

3-acryloyloxy-2,2-dimethylpropyl;

3-methacryloyloxy-2,2-dimethylpropyl;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[3-(2,2-dimethylpropoxy)carbonylamino]ethyl acrylate;

2-[3-(2,2-dimethylpropoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

or 2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate.

12. The dental composite material of claim 11, wherein the at least one (meth)acrylic ester compound is present in an amount of from about 1 to about 99 weight percent, the at least one polymerization initiator is present in an amount of from about 0.1 to about 5 weight percent, the at least one inorganic filler is present in an amount of from about 20 to about 90 weight percent, and the at least one space-filling compound is present in an amount of from about 1 to about 100 weight percent.

13. The dental composite material of claim 11 further comprising at least one of a photoinitiating accelerator, an activator, a pigment, a radiopaquing agent, a stabilizer, and an antioxidant.

14. A dental composite material comprising at least one space-filling compound functionally terminated with at least two urethane (meth)acrylate groups.

15. The dental composite material of claim 14, wherein the at least two urethane (meth)acrylate groups independently are selected from 2-(carbonylamino)ethyl acrylate;

2-(carbonylamino)ethyl methacrylate;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[3-(2,2-dimethylpropoxy)carbonylamino]ethyl acrylate; and

2-[3-(2,2-dimethylpropoxy)carbonylamino]ethyl methacrylate.

16. A method for producing a dental restoration article with reduced shrinkage, comprising the steps of:

(a) mixing at least one space-filling compound with at least one of

(i) at least one (meth)acrylic ester compound,

(ii) at least one polymerization initiator, and

(iii) at least one inorganic filler; and

(b) forming and curing the dental restoration article;

wherein the space-filling compound comprises at least one of

wherein

R₁ and R₂ are independently acryloyl;

methacryloyl;

2-acryloyloxyethyl;

2-methacryloyloxyethyl;

2-acryloyloxypropyl;

2-methacryloyloxypropyl;

2-(carbonylamino)ethyl acrylate;

2-(carbonylamino)ethyl methacrylate;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

or 2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate;

R₃ and R₄ are independently H, CH₃, alkyl, or aralkyl such that the carbon atom attached to the cyclopentane ring is aliphatic with at least one H; and

R₅ and R₆ are independently H, CH₃, alkyl or aralkyl, containing one carbon less than R₃ and R₄ respectively;

provided when R₃ and R₄ are CH₃ and R₅ and R₆ are H that R₁ and R₂ are independently 2-(carbonylamino)ethyl acrylate;

2-(carbonylamino)ethyl methacrylate;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

or 2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate;

wherein

R₇ and R₈ are independently 2-acryloyloxyethyl;

2-methacryloyloxyethyl;

2-acryloyloxypropyl;

2-methacryloyloxypropyl;

3-acryloyloxy-2,2-dimethylpropyl;

3-methacryloyloxy-2,2-dimethyl propyl;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[3-(2,2-dimethylpropoxy)carbonylamino]ethyl acrylate;

2-[3-(2,2-dimethylpropoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

or 2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate;

R₉ and R₁₀ are independently H, CH₃, alkyl, or aralkyl such that the carbon atom attached to the cyclopentane ring is aliphatic with at least one H;

R₁₁ and R₁₂ are independently H, CH₃, alkyl, or aralkyl, containing one carbon less than R₉ and R₁₀ respectively;

wherein

R₁₃ and R₁₄ are independently 2-acryloyloxyethyl;

2-methacryloyloxyethyl;

2-acryloyloxypropyl;

2-methacryloyloxypropyl;

3-acryloyloxy-2,2-dimethylpropyl;

3-methacryloyloxy-2,2-dimethylpropyl;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[3-(2,2-dimethylpropoxy)carbonylamino]ethyl acrylate;

2-[3-(2,2-dimethylpropoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acryl ate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

or 2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate;

R₁₅, R₁₆, and R₁₇ are independently H, CH₃, alkyl, or aralkyl such that the carbon atom attached to the cyclopentane ring is aliphatic with at least one H;

R₁₈ is H, CH₃, alkyl, or aralkyl, containing one carbon less than R₁₅, R₁₆, or R₁₇;

wherein

R₁₉ and R₂₀ are independently acryloyl;

methacryloyl;

2-acryloyloxyethyl;

2-methacryloyloxyethyl;

2-acryloyloxypropyl;

2-methacryloyloxypropyl;

2-(carbonylamino)ethyl acrylate;

2-(carbonylamino)ethyl methacrylate;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

or 2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate;

R₂₁, R₂₂, and R₂₃ are independently H, CH₃, alkyl, or aralkyl;

wherein

R₂₄ and R₂₅ are independently acryloyl;

methacryloyl;

2-acryloyloxyethyl;

2-methacryloyloxyethyl;

2-acryloyloxypropyl;

2-methacryloyloxypropyl;

2-(carbonylamino)ethyl acrylate;

2-(carbonylamino)ethyl methacrylate;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

or 2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate;

R₂₆ and R₂₇ are independently H, CH₃, alkyl, or aralkyl;

provided when R₂₆ and R₂₇ are H that R₂₄ and R₂₅ are independently 2-(carbonylamino)ethyl acrylate;

2-(carbonylamino)ethyl methacrylate;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

or 2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate;

wherein

R₂₈ and R₂₉ are independently acryloyl;

methacryloyl;

2-acryloyloxyethyl;

2-methacryloyloxyethyl;

2-acryloyloxypropyl;

2-methacryloyloxypropyl;

2-(carbonylamino)ethyl acrylate;

2-(carbonylamino)ethyl methacrylate;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

or 2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate;

R₃₀ and R₃₁ are independently H, CH₃, alkyl, or aralkyl;

provided when R₃₀ and R₃₁ are H or CH₃ that R₂₈ and R₂₉ are independently 2-(carbonylamino)ethyl acrylate;

2-(carbonylamino)ethyl methacrylate;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

or 2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate;

2-(carbonylamino)ethyl acrylate;

2-(carbonylamino)ethyl methacrylate;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

or 2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate;

wherein R₃₄ and R₃₅ are independently 2-acryloyloxyethyl;

2-methacryloyloxyethyl;

2-acryloyloxypropyl;

2-methacryloyloxypropyl;

2-(carbonylamino)ethyl acrylate;

2-(carbonylamino)ethyl methacrylate;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

or 2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate; and

wherein R₃₆ and R₃₇ are independently 2-acryloyloxyethyl;

2-methacryloyloxyethyl;

2-acryloyloxypropyl;

2-methacryloyloxypropyl;

3-acryloyloxy-2,2-dimethylpropyl;

3-methacryloyloxy-2,2-dimethylpropyl;

2-(2-ethoxycarbonylamino)ethyl acrylate;

2-(2-ethoxycarbonylamino)ethyl methacrylate;

2-[1-(2-propoxy)carbonylamino]ethyl acrylate;

2-[1-(2-propoxy)carbonylamino]ethyl methacrylate;

2-[3-(2,2-dimethylpropoxy)carbonylamino]ethyl acrylate;

2-[3-(2,2-dimethylpropoxy)carbonylamino]ethyl methacrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl acrylate;

2-[2-(2-ethoxy)ethoxycarbonylamino]ethyl methacrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl acrylate;

2-(omega-polyoxyethylenecarbonylamino)ethyl methacrylate;

2-(omega-polyoxypropylenecarbonylamino)ethyl acrylate;

or 2-(omega-polyoxypropylenecarbonylamino)ethyl methacrylate.

17. The method of claim 16, wherein the at least one (meth)acrylic ester compound is present in an amount of from about 1 to about 99 weight percent, the at least one polymerization initiator is present in an amount of from about 0.1 to about 5 weight percent, the at least one inorganic filler is present in an amount of from about 20 to about 90 weight percent, and the at least one space-filling compound is present in an amount of from about 1 to about 100 weight percent.

18. The method of claim 16, wherein the dental restoration article further comprises at least one of a photoinitiating accelerator, an activator, a pigment, a radiopaquing agent, a stabilizer, and an antioxidant.

19. The method of claim 16, wherein the dental restoration article is selected from fillings, artificial teeth, bridges, crowns, inlays, onlays, laminate veneers, facings, pit sealants, fissure sealants, cements, denture base materials, denture reline materials, orthodontic splint materials, and adhesives for orthodontic appliances.