JPS5821607A - Adhesive for dental purpose - Google Patents

Abstract

PURPOSE:An adhesive for dental purpose that is made by using a specific amount of a vinyl compound bearing both lipophilic part of 7 or more carbon atoms and hydrophylic part of PO(OH)2 in one molecule, thus showing high adhesion to any of them, teeth, metal and organic macromolecular substance. CONSTITUTION:In an adhesive for dental purpose, consisting of polymerizable monomers, an adhesive vinyl compound of the formulaI[R1, R2 are H, 1-6C hydrocarbon, COOA (A is hydrocarbon), halogen; R3 is H, hydrocarbon, halogen; R3 is H, hydrocarbon, halogen, CN; m is 1-3; R4 is formula II-VI (Ra, Rb, Rc are m+1 functional organic groups of 4-40C, 5-40C and 8-40C respectively; X, Y are O, S, NRd where Rd is H, alkyl; Z is O, S; k is 0, 1]such as a compound of formula VII is used by more than 0.5, preferably 1.5-50wt% based on the total amount of polymerizable monomers. Preferably, a monomer of formulaI and an acrylate or methacylate monomer are mixed at a weight ratio of 1.5/98.5-50/50.

Description

[Detailed description of the invention] This invention lj! This article is about dental adhesives that adhere to tooth tissue, dental biomaterials, and one-layer organic polymeric materials K11L - What is dental adhesive? Adhesives for fixing inlays, crowns, orthodontics, etc. to tooth tissue or abutment teeth, as well as filler-mixed adhesives for dental Ili and 4DII adhesion. Today, organic polymer materials and metal materials are used in a wide variety of areas in dental preservation, prosthetics, and correction. Pigeon house, tooth structure that is placed in the oral cavity for the purpose of treatment.
Organic polymer, *Quality-Tsuboma.

The bond between chi-machine polymer and gold is essential. For example, it is legal to lock the inlays and crowns into the socket using mechanical fittings such as the undercut method and precision fittings for the inlays and crowns.

Mechanically retaining the 9-tooth array 0JkO metal IIIM appliance, bridge, etc. in the oral cavity is at the Meinichi level of technology. However, tooth substance - organic polymer, tooth substance - metal, organic polymer -
If a strong 111 adhesive that can bond metals easily with mechanical methods is released, it is expected to speed up dental treatment, improve quality, and make a significant contribution to this field. Ru. 4I-@54-111411, JP 1
The adhesive disclosed in No. 154-1!3a8 is 0.
Based on the third objective, it is estimated that organic polymeric materials and metallic materials remain in the tooth structure for a long period of time in the oral cavity under 100% humid conditions and under repeated blowing pressure. There is no adhesive that can hold both together. front,
-PO(OH), a J11 group with a group 2-
Methacryloyl diethyl dihydrogen phosphate is said to have high adhesive strength to metals, and its use as an adhesive agent for metals has also been attempted. However, in our own experiments, the above compound was found to have significantly poor water resistance.
O was not used in the oral cavity. Furthermore, t9, JP-A-1185! Ni-C, which is a metal material disclosed in No. 113089, has excellent binding properties, but
Some materials are not said to have sufficient 111 adhesion to r-alloy (9 $-milG). The present inventors sought an adhesive that could bond and hold both an organic polymer material and a metal material @0 to the tooth structure in the oral cavity, and used various functional vinyl compounds to Tsumugi, who has repeatedly studied the technique of curing and adhesion by heavy curing on the surface layer of polymeric materials, under sI Jun,
Compounds that have strong adhesion to tooth structure, metals (Ni-Cr alloy, Co-Cr alloy, stainless steel, etc.), organic polymer materials (polymethylmethlyl), etc.) have a carbon number. Recognizing that it is found in a group of vinyl compounds that have both a relatively large lipophilic moiety of 7 or more and a strong hydrophilic (Il-like) po(on) group in one molecule, we arrived at the first research. 〇That is, the present invention provides a dental adhesive consisting of a polymerizable monomer, in which a binding vinyl compound represented by the following general formula is used as a polymerizable monomer in a proportion of 0 to the total polymerizable monomer. ．． This is a dental adhesive characterized by the fact that it is more than heavy.

[Edashi, in the above, Rs, Rs, shiR4 and Otori represent the following.

Rx+H, halogen having 1 to 6 carbon atoms (α, Br, Ft
9 is a hydrocarbon which may have I).

-COOm (M is a hydrocarbon group having 1 to 20 carbon atoms, which may have a /10 gen), before halogen Rs: Synonymous with Rt, Rs+H, which may have a halogen having 1 to 6 carbon atoms. Hydrocarbon group, halogen or -CNrm s 1-3
01 to 11 Ra + (COX)I! IRa(Y)k, (Co)
mRb(Y)k.

(ZCO)-Ra(Y)k, (Z)mRb(Y)k 9 represents (Re)m(Y)k 0 However, Ra, Rb,
Re is the member prime number 4~40%S~40%~40(
(m+1) valent organic group. X$P and Y ore 0.8 weight or NRd (RdFiH weight is an alkyl group with 1 to 4 carbon atoms)
El! ! For me, Ot9 is 1tII. ] In this 11fl book, the organic group Akebono is the following (1) and (
11) is used as Akebono.

Inside OH group, Coon group, NHs group and halogen (
It is composed of a hydrocarbon group which may have α, lr, Fll or the like as a substituent, and the hydrocarbon bulk group GDIll is composed of a hydrocarbon group which may have a number (2 to 20) of the above substituents.
Ether i1. by o or 8. Groups bonded by ester, ido, carbonyl mt, or phletane bond. In this case, not only the case where the main chain of the organic group is composed of a bulky hydrocarbon group of type II, but also the case where a part of the hydrocarbon group is included in the side chain are included.

(Example) When CONH%0CONH) is expressed as 3, the following is also exemplified as 01bX. For simplicity, the double bond side is expressed as [Company C] and the phosphoric acid side is expressed as (PO(OR)*).

(”c,,c)-mu-(PO(OH) goose)(c=c)-
M B - (PO (OH) Snow) [C C) - AB M'l - (PO (OR) m) (C-C) - (M B) g - M /
-(AjB #)β(PO(0H)s)(#, β...
...Repeat) (C=C) -A-(PO(OH),)÷mu'[C纏C]-MuBA'B'A'-[PO(0)i),)
N 1# ↑ Muichi' (C=C) -ABA'B'A"- (PO(OH) wet)
B1 r # 1″ (C=C)-mu1mu'lmuichi (PO(OR) snow) +1,
1 MU1 MUNA ONE*f! In the above, the term "hydrocarbon group" is used in a broad sense, including halogenated hydrocarbons, even if the term "hydrocarbon group" is not specifically mentioned.

Among these adhesive vinyl compounds, those having the same group as acrylic monomers and polymers commonly used as dental organic materials are preferred in terms of copolymerizability and adhesiveness with organic materials. General formula [However, R- represents H19 represents CHs, and R'a represents a carbon number of 4 to 40t)2@0 organic group. X%Y and k
A vinyl compound in which *v%-r is the same as OX, Y, and k in formula U(1) is preferably used. Sara K (ml) formula II! Among the compounds 0 shown below, those shown in (-) to (1) 2 below are I[
It is more preferable from the viewpoint of safety, storage stability and adhesive strength as a material for Qin.

H1 (OH [Edit, Rd and Wing'd U H meeting has 1 carbon number
~4 hydrocarbon group SR@h organic group having 8 to 5 carbon atoms].

[Edashi, Rd and 凰 (described in (1) 2 O
A vinyl compound represented by Rd and age].

C) Cll5 Q [Kuueshi, R's is -) Described in 2 (D'Was is the same).

A vinyl compound represented by the following formula:

[However, lif#1jll prime number 1 to aoo21i) Yes 11J1゜ml (1) 2 is the same as k described] CHHO2(CO)k-Rlf [Represents edashi s kao★ or 1] , ll'f represents an organic group having 1 to 300 carbon atoms.

) CHs 0H [Round, R'a is the same as OR'a described in (1) 2] A vinyl compound represented by the formula 041,
The following O are preferably used.

Police the law of nature.

A divinyl compound represented by 0=P-OH OH [R- represents a trivalent organic group having 4 to 4 carbon atoms].

#i1 is exemplified as a compound represented by the above general formula.

CHs O Akira CHs　　　　　　　　0 0H CHs Q OH OH Mouth Is 0 OH8O OH OH OH 1 Gin OH [ OH OH OH ■ OH OH H OH Akira 1 CHI OH □H 1 CHsOH.

CHs　　　　　　　　0 OH ― OH Utts uti υM CHs Q CHs 0m number H fable C=C.

C1h OOCfcH dew) iiCHs Cout00C(-CH2,I,, CHsCbS+cHj
V CH1 CM Snow (Enko Hs CHsOOCCHmCHsCOOCIis口1sOck
hcHsCH婁00C+Ckb);, CHsCH*
5CHa@ υh 01l CHs 0 1i H0 HHO H H 0H ■ H H H R Hs H OH OH 0M Crystal R θ11 In formula (1), when Ra is an organic group with carbon ms of 3 or less, In the case of an organic group with a carbon number of 4 or less, 9 is a liability.In the case of an organic group with a Re of 7 or less, the adhesive strength to both tooth material and metal and its water resistance are low, and Kd is used for the purpose of this invention. I'll come with what I don't have. Also Ra, Rh.

When R@ has 40 or more carbon atoms, the large organic group significantly reduces the chemical properties of the molecule based on phosphoryl residues (po(oH)), resulting in a decrease in !1 adhesion. The group of compounds represented by the formula 1%0 have 4 to 5 carbon atoms, but have excellent adhesion to metals, but denture adhesion exceeds known compounds. However, when the number of carbon atoms is 6 or more, the denture adhesion strength 4 is further improved and the object of the present invention cannot be fully achieved. 0 OrgalL*phoaphorus Compou
nds (G, M, Kosola poff arrival, W
ll@F, 195 G), Organopho
sphorus Monom@rsand Poly
m@rs (Ye, L, G@ft@r, Rr@
gamonPr@ms, 1962) *Modern Organic Synthesis Series S. Organic compounds (edited by the Organic Synthetic Chemistry Association,
Gihodo.

- H-X-Ra -y-HtIjt ReiE Sete HmC
-('-cox-Ha-y-H and 1L1, then more than the same mole of oxychloride VtH-X-Ra-POs''
-・2Nt;"j or H-X-R PO(OR%(R
The adhesive vinyl compound can be obtained by converting the s-legged element (l~lO hydrocarbon group) into a metal and reacting it with m11sc-C-Coα under the conditions of Shime-Tuten-Baumann reaction. In this case, it is also possible to use it alone by applying 1iK.

It is usually used after being diluted with another monomer that can be copolymerized with the adhesive vinyl compound. By selecting other monomers, it is possible to adjust the adhesive property, wettability, curing properties, mechanical properties, etc.Other monomers include adhesive vinyl compounds, etc. Any substance that can be copolymerized with the human body and has no physical properties on the human body, such as styrene, p-chlorostyrene, vinyl acetate, (meth)acrylic acid, N-n-f
) Acrylic acid sg* such as dimethyl (meth)acrylic acid, N-(meth)acrylic acid, etc. can be used, but (meth)acrylate type, which is commonly used in the dental field, can be used. Monomers are used. When it comes to (meth)acrylate monomers, (QIs-
CH-COO￥-Q [However, R- is Kt or CHs,
Q is an organic group having 1 to 50 carbon atoms.

r represents an integer of 1 to 4] (see above for the definition of the organic group). Examples of such monomers include the following percentages.

(1) Practical (meth)acrylate methyl (meth)
Acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate.

1-o-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, decyl (meth)acrylate, 2-uryl (meth)acrylate.

Stearyl (meth)acrylate, 2-bido-mu-diethyl (meth)acrylate (sometimes referred to as HEMA), 2-hydroxypurpyl (meth)acrylate, dimethyla(noethyl(meth)acrylate, dietheryl(meth)atari) rate, 3-ri acl-3-
Dipropyl methacrylate in human W, 2,3-dipropyl (meth)acrylate (H) 2-rich simple (meth)acrylate) number)
0 Ethelene glycol di(meth)atarylate.

Diethylene glycol di(meth)acrylate.

Triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrate, propylene glycol di(meth)acrylate, dibu-gastric bilene glycol di(meth)arylate, trip-p-bylene glycol Propanediol di(meth)acrylate, which is represented by di(meth)acrylate (dro)Q or alkylene (usually having 3 to 8 carbon atoms).

glycerin di(meth)acrylate), 1,8-butanediol di(meth)acrylate, 1,4-butanediol di(meth)acrylate), 1. I-pentanediol di(meth)acrylate.

l,6-hexanediol di(meth)acrylate,
neobentyl glycol di(meth)acrylate), 1.
8-octanediol di(meth)acrylate, 2,3
- Dibuteneobenglycol dimethacrylate (he)Q having a bisphenol derivative residue.

Bisphenol-A di(meth)acrylate, 2.2
-bis[(meth)acryloyloxypolyethoxyphenyl]furopane-0-QC-C=CH*, t = integer from 1 to 9), 2,2'-bis(4-acryloyloxypolyethoxyphenyl) Propane, 2,2'-bis(4-(3-
Among these, those with a QO* prime number of 15 to 30 are preferably used. .

OHOH → Q tl -CH5CHCHsOCCHs0CHsCHCHs-(uethane, 1,4 bis[3
-(meth)acryloyloxy-2-human dipropoxy]butane0)Q is JOCONHTNHCOOJ
Urethane di(meth)acrylate represented by (J is an alkyl group (excessive, *substance 2-1G), 〒 is a carbon@1-sO organic diinocyanate residue) For example, 4$-11i50-687 The products listed in the issue are used. acrylate, tesirameterolmethanetetotsu (meth)acrylate), N, m
-(2,2,4-)dibutyl to dibutyl)bis(!
-(Anocarlxy)propane-1,3-diol cotetramethacrylate These monomers are 11m or range combined to form one adhesive Bier compound KI! I41- be done. Among the above monomers O, preferred are methalyl esters such as methyl methacrylate, ethyl methacrylate), HIMA,
Bis-GMA, bip7x7-lum dimethacrylate, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate.

These include neopentyl glycol dimethacrylate and trimethylolethane methacrylate.

When these monomers are mixed, it is essential that the adhesive vinyl compound be used in an amount of at least 0.08% by weight based on the total polymerizable monomers. If the weight is less than 0.5, the adhesive effect will be low, and it is difficult to fully achieve the object of the present invention. Usually, it is preferably used in a weight range of 1.5 to 50 weight. Related Diene Phosphate.

Bis-8-methacryloyloxyether hydride-attack diene phosphate, etc.) may also be used in combination.

The dental adhesive of the present invention has a bonding surface Klk cloth or is filled with heating*Xm-ultraviolet-, visible light, etc. It is monopolymerized and cured to exhibit adhesive function.

Usually, curing is carried out by adding a sensitizer and irradiation, or by adding a polymerization initiator. In this example, the polymerization initiator and sensitizer are collectively referred to as a curing agent, and %Aho Usable curing agents include organic peroxides, azo compounds, organometallic compounds, redox initiators, ultraviolet and visible light.
Various O substances such as photosensitizers for K, specifically,
Benzoyl peroxide, G-t-butyl peroxide.

Tamenhide tetraperoxide, t-butyl hydroperoxide, mether ether ketone peroxide, azobimain ester peroxide, dibutylborane, aromatic sulfinic acid (double salt).

Water peroxide volume/r base, cumene hydroperokinide/F ring system, benzoyl peroxide/N, N-sial luaniline derivative system, 7 scorvin/CI''+ ring system.

and benzoin ethyl ether. Among these, 0 which is preferably used is benzoyl peroxide, azobisinopropyronitrile, triptylphonate, aromatic sulfinic acid (9 is salt), aromatic sulfin salt/diasilver oquinide/ This is an aromatic tertiary amonyl aromatic tertiary amino acid-based vinyl compound with good adhesion properties, which is diluted with a volatile organic solvent with a peak point of 150°C or less at 76°Torr and applied to the adhesive surface (4). □This pigeon house.

This can be achieved by using the above-mentioned copolymerizable monomer in combination. After coating, the volatile organic solvent is evaporated by blowing air or nitrogen to form a wave film of vinyl compound on the adhesive surface. Suitable organic agents for general use include methanol, ethanol, amethane, methyl ethyl ketone, methyl acetate, ethyl acetate, silyl methane, chloroform, ethyl ether, impropyl ether, and toluene. Self-defense. The ratio of these volatile solvents to all polymerizable monomers is preferably less than or equal to SOO times (weight ratio). At large dilutions exceeding 0300 times the amount, which is 100 times the amount or less, the volatile solvent can be evaporated and the deposited film formed on the adhesive surface is too thin, resulting in a significant decrease in the adhesion strength.

A must-have for this estrus adhesive! Depending on the total amount of polymerizable monomers, in an amount of 10 times or less (weight ratio), a conventional, organic, or inorganic-organic composite filler (usually with an I2 diameter of 100μ or less) is added. 80 weight or more) may be added. Inorganic products include 1 quartz, water insects, feldspar,
Talc, plaster, aluminum construction, no 5i! ! Examples include silica, m-type glass, etc., and it is preferable to use them after treatment with silane. Yijiu.

Polymethyl methacrylate is the most common.

Examples include polyvinyl chloride and polystyrene. -11 Organic composite fibers used include silane-treated inorganic fibers coated with the above-mentioned polymer.

In addition, the Honjitsu aO adhesive contains Hyde 12dF non-(nomether ether A/, 2.6-jet@rt-p?lu?-cresol), a polymerization inhibitor, an antioxidant, or an ultraviolet lI
When supplying the dental bonded steel pipe 1 of the present invention by adding an absorbent, a coloring agent, etc. as necessary, a nine-pack scissor form is required in consideration of storage stability. In redox polymerization initiators, the oxidizing agent and reducing agent must be packaged separately. Examples of this are IIi, two-part packaging of vinyl compound reducing agent (or oxidizing agent) and vinyl compound + saponifying agent (previously reducing agent), or vinyl compound + oxidizing agent (or reducing agent) and volatile organic Molten reductant reducing agent (
or oxidizing agent) in two-part packaging, vinyl compound + oxidizing agent (
An example of this is a two-part coloring system with a 2-split reducing agent (T or oxidizing agent). When using a photosensitizer as a heavy-containing W/a pongee agent, the vinyl compound photosensitizer is exposed to 1 light of Kutani 1iKW? must be true. We met. An initiator that starts polymerization within a short time upon contact with a vinyl compound (for example, Tripterpo 27)
When using a vinyl compound and a heavy metal initiator, the vinyl compound and heavy metal initiator must be packaged separately and must not be separated. Immediately before use, the dentist should equalize the adhesive supplied in separate packages and apply it to the adhesive surface. If the adhesive to be coated contains a volatile organic solvent, spray the film with air to fully evaporate the solvent before adhering. The adhesive of the present invention is suitable for filling and restoring tooth socket fI4 with composite resin.

Tooth group 11! The adhesive applied to the composite resin is obtained by adding the above-mentioned adhesive vinyl compound to the composite resin. W! Inlays are used as dental filling materials with adhesive properties.
Used as a rounding adhesive for attaching an onlay crown* to a cavity or abutment tooth, as an orthodontic adhesive, as an O-glue to hold bridge posts, etc., as a T-9 Fisher seat tent, etc. I can do it ◇ Fuck it O
If you have 1 KM, please refer to the above O for the specific composition of the adhesive! For example, in order to fill with composite resin, in the case of adhesive, #is $111181-118089, 1s.
-11063? According to the composition shown in No. 41, the above-mentioned adhesive vinyl compound was mixed into an adhesive for 2 to 40 minutes*i.
Let me know.

Other synthetic monomers (Big-GM, ■1, Marozo dimata ν-late, etc.) can be diluted with organic solvents (ethanol, etc.) and contain mold temperature curing agents. It's used. When adding an adhesive vinyl compound to a composite resin, add 20 to 40% by weight of a polymerizable monomer such as lie-GM and 80% by weight of a filler according to the composition shown above. ~60wt- Ordinary method O filling #l
) K, the above-mentioned adhesive vinyl compound at a weight of 3 to 1! (
Nine types of monomers are used. The adhesive thus obtained is applied to the tooth using the conventional method (it is impossible to etch the tooth surface with phosphoric acid and then apply the real $10 III adhesive).
The hardened large composite resin strongly adheres to the tooth structure and provides excellent mechanical retention against undercuts. front,
Inlay, onlay.

When attaching tarakun, etc. to a support base, use 80 to 9 parts by weight of methyl methacrylate, and 1 to 9 parts by weight for adhesion. - 2 to 20 parts by weight, polymethyl methacrylate 50 to 150 plates, and a large one is used. By applying adhesive in a large area on one stroke and making it adhere, it is possible to adhere inlays, onlays, and cracks to the tooth structure, something that was impossible with the 1111 adhesive method. and 1-) As described above, the adhesive of the present invention has a non-111 eyebrow shape as an adhesive for sanitation. Furthermore, examples will be given, and a typical adhesive vinyl compound will be used in a round case.
Example 1 - Yuki 7 Using the 11 O brass-adhesive vinylized structure shown in Kame 111, 1 lower l! Therefore, we separated two moat cap chain adhesives and attached them to Ichihara composite resin leprosy dentin KII! with l1lE chain adhesive, and measured the degree of O adhesion. -GMA 40 parts by weight chain-attaching vinyl compound 118
#Benzoyl peroxide 1.5 #
■ 100 parts by weight of ethanol
-Jetanol-P-) Luizine 1.71 Place the denture molar into a prismatic K11 so that the dentin comes out from the adhesive 11.
Prepare the protruding dentine rod and the ivory square rod (1) 40m
Rinse with water si* for 1 minute. Next, wash thoroughly with running water, blow nitrogen out of the bottle, and wrap the side layer with an Al9 Tsuru strip. On the other hand, wipe off the moisture with the Elephant Stick 1i glued to the WHO. Place 0 human teeth, use ivory positive resin [C1earfil FJo (manufactured by Kuraray), 111DL, and glue this paste on the denture and ivory adhesive by sandwiching them between the two sides. Immerse the IIK sample piece in water at 37°C for 30 minutes to bond.
Tensile adhesion with 1y tear test! Ill& was measured (crosshead speed 2/m1n), and the result was shown to be true. One denture was used to evaluate one type of adhesive, and Table 1 shows the average value of gamma 0 @ adhesion force to'f. Perform an adhesion test on trout by replacing the adhesive vinyl compound in Table 2 with the O-chemical compound in the first solution, and show the results in the same table. The test method was the same as in Example 1-*1.

I-1'Yohaku Shimajo 11 ＄1128-84 Decoration 0 Using the adhesive vinyl compound used in Example 0IIIA, a powder-liquid adhesive was prepared according to the following recipe, and an adhesion test to metal was conducted. .

Methyl methacrylate 95゜'benzoyl peroxide 1'V-enclosed polymethyl methacrylate 10G book! Benzene Sulfin Mon N1 3
p-N, N-jetanol-p-toluidine 1
'Dental nickel-rim alloy, Now Chr@s
n (1) (Ni j 11!, ?11. Cr:
6011. Other 13L) - Wa Giken Co., Ltd.) casting chips were polished to give a smooth surface, and the φ1060 silicon
Finished with carbide polished side.

It was washed with sonic waves and then dried. Paste a large cellophane tape with a 5wφ hole on the test surface and make a circle. On the other hand, 7■φX165
m1D8U8◆S04 stainless steel rod φ100G in the same way
After Kenkeiho sonic cleaning, it was dried. ■Package and W-package of equal weight are placed on a gentle plate and 1) Rub for 1G for 40 seconds, apply the resulting 9-Thriller on the adhesive surface, and glue the Ni-Cr alloy and stainless steel rod together in a center to form a circle. After 1 hour of adhesion, immerse in water at 37°C. ! After a period of time, the tensile strength was measured using an instrumental tensile tester (crosshead speed 8 M/ml n), and the results are shown in the first true right column.

Comparative Examples 7 to 12 Examples 8 to 540 adhesive vinylized buildings!
Type 6 0 Bi listed in lIK; instead of nickel
The adhesion test to chromium alloy was conducted using the same method as in Examples 24-46.

The results are shown in the right column of the Table of Contents.

As the 111th! using nine SSO compounds described in .

The sample was immersed in water at 37°C and stored for 10 days, after which the adhesive strength O11 was determined. The results are shown in section S@ and circled.

As is clear from the results shown in the example and comparison flK1
Motoya? 10 Dental adhesives not only strongly adhere to dentin but also show excellent adhesion to metals, with a rating of 90 and <K. (Comparison 1 [).

It is surprising that the adhesive of the present invention exhibits much higher adhesive strength! With Jin.

Patented wheat flour Kuraray Co., Ltd. Representative Patent Attorney Uta Honda

Claims (1)

[Scope of Claims] (1) In a dental adhesive consisting of a polymerizable monomer, an adhesive vinyl compound represented by the following general formula is used as one polymerizable monomer by O3s weight relative to all polymerizable monomers. - A dental adhesive characterized by using the above. Tsukuda [However, in the above formula, Vk "CRx, Rls RL R
4$P and m represent the following: RatH, a hydrocarbon group that may have a halogen with 1 to 6 carbon atoms, COOm (a hydrocarbon group that may have a halogen with a carbon number of 111 to 8G) Or ha■gen. Place S 1 龜凰と-龜- 8s:H, a hydrocarbon group that may have a carbon number of 1 to 6, a halogen te#icN! II! Integer R4 from 1 to 3: (COx')mRa(Y)k, (Co)-R
a(Y)k. (ZCO Police Ra (Y)k, (Z)mRb (Y)
k meeting ft haclla-(Y)ktll! Was. However, Ra, Rh, and Re each have 4 to 4015 to 4 carbon atoms.
0. $~40 (m+1)lj organic group. X and yF
io, 8 or NRd (Rd FiHt is an alkyl group having 1 to 4 carbon atoms), and 2 represents O or 8. k represents Ol or 11] (To)) l*Adhesive vinyl compound has the general formula % formula % [However, R3 represents lIt or CHI, Ra &
! 2I with 4 to 40 carbon atoms! represents an organic group. The dental adhesive according to claim 1, wherein X, Y and k are the same as X1YsI- and k, respectively, according to claim 1. A vinyl compound having the general formula [Yoshitomo, Rd and da are Hl or a vertical hydrogen group having 1 to 4 carbon atoms, and R is a divalent organic group having 2 to 30 carbon atoms] Claim 277 which is
4. Dental adhesive according to item 4. -) Claim 2, wherein the linear adhesive vinyl compound is a vinyl compound having the general formula [R4 and R- are the same as Rd and Rd described in Claim 3]. Dental adhesives listed. (Is) The line-adhesive vinyl compound has the general formula % [rounded out, 'B: sFi R according to claim 2]
's fC same oR- represents a hydrocarbon group having 2 to 30 carbon atoms] Claim - Dental adhesive according to No. 2114 0 (6) # Adhesive vinyl compound is generally Formula [where kti k as described in claim 1]. The dental adhesive according to claim 2, wherein Rf is a vinyl compound represented by a divalent organic group having 1 to 30 carbon atoms. (v) The adhesive vinyl compound is a vinyl compound represented by the general formula % [where kiiOl or l is represented, and R'f represents a monovalent organic group having 1 to 30 carbon atoms] Certain patent claim 2 O*Mum
Adhesive. (IB) The adhesive vinyl compound is a vinyl compound represented by the general formula % [6 represents a trivalent organic group having 4 to 40 carbon atoms].
Dental adhesives as described in section. ψ) @ Adhesive vinyl compound has the general formula % formula % [However, Ra is R'a described in claim 2
The dental adhesive according to claim 2, which is made of a vinyl compound moistened with [same as]]. @ Rd and R'd are both H, and Re is (-C
The dental adhesive according to claim 3, wherein p is an integer of 2 to 20. &, a(sl.,) (b) Both Rd and Rd are KH, and R@ is -csOf
abcsO#(α1-out%OC&-[OdaL-@'
The dental adhesive according to claim 3, which is represented by "ym Q~5,1'=an integer of θ~5". (4aa and ma are both H, and R@ is () , (Meeting I
! The dental adhesive according to Item 3. ) Rd and R'd are both CHs and R. has 2 to 6 carbon atoms.
A dental adhesive according to claim 3, which is represented by a hydrocarbon group. 3) The dental treatment according to claim 3, wherein either Rd and R'j is represented by -CHtC-CHs and the other is represented by H, and R is represented by -CH-. Adhesive 0 (l)
)l [Edit, either i or fsO is cHs and the other is H
[Oq represents a number from 2 to 1101] Claims 3.
l1 arrival hard. - Mackerel is ■, l/・ is the general formula + C output [Edashi, V is an integer from 1 to 20] Dan is a patent represented by a phenyl group - Request 0 III! Item 5: 0* Adhesive for medical use. -Wrinkle polymerizable monomer is g** adhesive starting vinyl compound rJ-
Formula 12 (CTo-CM-000%-Q ((ilL,
It's a 41 Request for permission @II statement o R
Synonymous with 's. QFi is composed of an acrylate monomer having an r@O organic group s r h an integer from 1 to 4 with a carbon number of 1 to SO.Patent Claim 01
111 Item 1 0 Dental adhesive. ? s The dental MI according to claim 1s, wherein the ratio of the adhesive vinyl compound to the acrylate monomer is in the range of 1.5!9a, S to 50150 (weight ratio)
I adhesive. - Hardening agent is 0.0 per wrinkle polymerizable monoplane Zoo weight 11
1 to 30 parts by weight of the dental adhesive according to item 1. - Since the curing agent is an oxidation/reduction type curing agent, and the dental adhesive is packaged separately, the boiling point of the dental adhesive OH760T@rr described in Patent Claim O Section 20 is 150.
01111 ℃ or less
00 times the amount (weight ratio) or less of the dental adhesive ◎-
19. The dental adhesive according to claim 18, wherein the filler is added to the scissors-polymerizable monomer at an OSm of 10 or less (weight ratio).