JP6819592B2 - Dental plaque / stain inhibitor and oral composition containing it - Google Patents
Dental plaque / stain inhibitor and oral composition containing it Download PDFInfo
- Publication number
- JP6819592B2 JP6819592B2 JP2017533124A JP2017533124A JP6819592B2 JP 6819592 B2 JP6819592 B2 JP 6819592B2 JP 2017533124 A JP2017533124 A JP 2017533124A JP 2017533124 A JP2017533124 A JP 2017533124A JP 6819592 B2 JP6819592 B2 JP 6819592B2
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- meth
- hydrogen atom
- stain
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- 239000000203 mixture Substances 0.000 title claims description 48
- 239000003112 inhibitor Substances 0.000 title claims description 41
- 208000002064 Dental Plaque Diseases 0.000 title description 65
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 56
- -1 halogen ion Chemical class 0.000 claims description 52
- 229920001577 copolymer Polymers 0.000 claims description 51
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 239000000178 monomer Substances 0.000 claims description 43
- 239000000470 constituent Substances 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 28
- LWLHCZLCSDUDEL-UHFFFAOYSA-O C[N+](C)(C)CC(O)=P(=O)CCOC(=O)C=C Chemical compound C[N+](C)(C)CC(O)=P(=O)CCOC(=O)C=C LWLHCZLCSDUDEL-UHFFFAOYSA-O 0.000 claims description 25
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 18
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
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- LOPVAWVHGAWUPS-UHFFFAOYSA-M [2-hydroxy-3-(2-methylprop-2-enoyloxy)propyl]-trimethylazanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC(O)C[N+](C)(C)C LOPVAWVHGAWUPS-UHFFFAOYSA-M 0.000 claims description 3
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- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- NPKKRSHVJIQBKU-UHFFFAOYSA-N ornogenin Natural products CC(OC(=O)C=Cc1ccccc1)C2(O)CCC3(O)C4(O)CC=C5CC(O)CCC5(C)C4CC(OC(=O)C=Cc6ccccc6)C23C NPKKRSHVJIQBKU-UHFFFAOYSA-N 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000007505 plaque formation Effects 0.000 description 1
- 229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 1
- 229940093158 polyhexanide Drugs 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 229960001621 povidone-iodine Drugs 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- ZUFQODAHGAHPFQ-UHFFFAOYSA-N pyridoxine hydrochloride Chemical compound Cl.CC1=NC=C(CO)C(CO)=C1O ZUFQODAHGAHPFQ-UHFFFAOYSA-N 0.000 description 1
- 235000019171 pyridoxine hydrochloride Nutrition 0.000 description 1
- 239000011764 pyridoxine hydrochloride Substances 0.000 description 1
- 229940048084 pyrophosphate Drugs 0.000 description 1
- 229940005657 pyrophosphoric acid Drugs 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
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- 229940092258 rosemary extract Drugs 0.000 description 1
- 235000020748 rosemary extract Nutrition 0.000 description 1
- 239000010668 rosemary oil Substances 0.000 description 1
- 229940058206 rosemary oil Drugs 0.000 description 1
- 239000001233 rosmarinus officinalis l. extract Substances 0.000 description 1
- 239000010670 sage oil Substances 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- 229940079841 sodium copper chlorophyllin Drugs 0.000 description 1
- 235000013758 sodium copper chlorophyllin Nutrition 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 235000019983 sodium metaphosphate Nutrition 0.000 description 1
- 229960004711 sodium monofluorophosphate Drugs 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 235000019830 sodium polyphosphate Nutrition 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- GEYJUFBPCGDENK-UHFFFAOYSA-M sodium;3,8-dimethyl-5-propan-2-ylazulene-1-sulfonate Chemical compound [Na+].CC(C)C1=CC=C(C)C2=C(S([O-])(=O)=O)C=C(C)C2=C1 GEYJUFBPCGDENK-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000019721 spearmint oil Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- KWXLCDNSEHTOCB-UHFFFAOYSA-J tetrasodium;1,1-diphosphonatoethanol Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P(=O)([O-])C(O)(C)P([O-])([O-])=O KWXLCDNSEHTOCB-UHFFFAOYSA-J 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010678 thyme oil Substances 0.000 description 1
- 229940042585 tocopherol acetate Drugs 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- GYDJEQRTZSCIOI-LJGSYFOKSA-N tranexamic acid Chemical compound NC[C@H]1CC[C@H](C(O)=O)CC1 GYDJEQRTZSCIOI-LJGSYFOKSA-N 0.000 description 1
- 229960000401 tranexamic acid Drugs 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- VXYADVIJALMOEQ-UHFFFAOYSA-K tris(lactato)aluminium Chemical compound CC(O)C(=O)O[Al](OC(=O)C(C)O)OC(=O)C(C)O VXYADVIJALMOEQ-UHFFFAOYSA-K 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229940038773 trisodium citrate Drugs 0.000 description 1
- 229960005066 trisodium edetate Drugs 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229930007845 β-thujaplicin Natural products 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
Description
本発明は、高分子成分を含有するデンタルプラーク・ステイン付着防止剤に関し、より詳しくは共重合体を含有する口腔用組成物に関する。
本出願は、参照によりここに援用されるところの日本出願特願2015-155442号優先権を請求する。The present invention relates to a dental plaque / stain adhesion inhibitor containing a polymer component, and more particularly to an oral composition containing a copolymer.
This application claims the priority of Japanese application Japanese Patent Application No. 2015-155442, which is incorporated herein by reference.
従来から、健康で白い歯は美の象徴とされており、医学分野でも審美歯科領域が発達するなど、美しい歯の維持には大きなニーズがある。美しい歯を維持するには歯科医院の治療を受けることが出来るものの、治療に時間を要することや通院が必要となることから、より簡便な方法として自宅で行いたいというニーズが強い。 Traditionally, healthy and white teeth have been regarded as a symbol of beauty, and there is a great need to maintain beautiful teeth, such as the development of aesthetic dentistry in the medical field. Although it is possible to receive treatment from a dental clinic to maintain beautiful teeth, there is a strong need to do it at home as a simpler method because the treatment takes time and requires an outpatient visit.
このため、健康で白い歯を保ち続けることを目的とした練り歯磨きや液体ハミガキといったオーラルケア剤が数多く開発・販売されている。歯の白さを妨げる原因としては、食品、タバコやコーヒーなどによる汚れ(デンタルプラーク)や色素(ステイン)が歯面に付着・沈着することで発生することによる(非特許文献1)と考えられている。 For this reason, many oral care agents such as toothpaste and liquid toothpaste have been developed and sold for the purpose of maintaining healthy and white teeth. It is considered that the cause of hindering the whiteness of teeth is that stains (dental plaque) and pigments (stains) caused by food, tobacco, coffee, etc. adhere to and deposit on the tooth surface (Non-Patent Document 1). ing.
デンタルプラークの形成は、ペリクルと呼ばれる唾液中に含まれる糖タンパク質が歯面へと付着、さらに歯面に付着したペリクルに細菌が付着することから始まる。付着した細菌は、多糖類を産生し、歯面に堆積することでデンタルプラークとなることが知られている(非特許文献1)。 The formation of dental plaque begins with the attachment of glycoproteins in saliva called pellicle to the tooth surface, and the attachment of bacteria to the pellicle attached to the tooth surface. It is known that the attached bacteria produce polysaccharides and deposit on the tooth surface to form dental plaque (Non-Patent Document 1).
ステインの形成は、一般的には、ペリクルが関与して歯面へコーヒー、お茶やタバコのヤニなどが吸着することが原因である(非特許文献1)と理解されている。しかし、歯のエナメル質に含まれる微量元素が、コーヒーなどの色素と関与して着色する可能性も指摘されており(非特許文献2)、必ずしも歯面への色素の沈着の作用機序については明らかとなっていないのが現状である。 It is generally understood that the formation of stains is caused by the involvement of pellicle and adsorption of coffee, tea, tobacco tar, etc. to the tooth surface (Non-Patent Document 1). However, it has also been pointed out that trace elements contained in tooth enamel may be associated with pigments such as coffee to color them (Non-Patent Document 2), and the mechanism of action of pigment deposition on the tooth surface is not necessarily the same. Is not clear at present.
このため、作用機序が十分に明らかとなっていないものの、デンタルプラークやステインの付着・沈着を防止する方法について多くの研究開発がされている。これまでにピロリン酸塩などを配合することで歯面への汚れの付着を防止する方法(特許文献1)や、N−アシルアミノ酸とピロリン酸とを併用することで歯面への汚れの付着を防止する方法(特許文献2)等が開示されているものの、いずれもその歯面へのデンタルプラーク付着防止効果は、不十分であって満足できるものではなかった。このため歯面へのデンタルプラーク・ステインの付着・沈着を防止、抑制効果を併せ持つオーラルケア剤の開発が切望されていた。 For this reason, although the mechanism of action has not been fully clarified, much research and development has been conducted on methods for preventing the adhesion and deposition of dental plaques and stains. So far, a method of preventing plaque from adhering to the tooth surface by blending pyrophosphate or the like (Patent Document 1), or adhering plaque to the tooth surface by using N-acylamino acid and pyrophosphoric acid in combination. (Patent Document 2) and the like have been disclosed, but the effect of preventing dental plaque from adhering to the tooth surface is insufficient and unsatisfactory. For this reason, there has been an urgent need to develop an oral care agent that has the effect of preventing and suppressing the adhesion and deposition of dental plaque and stain on the tooth surface.
一方、2−メタクリロイルオキシエチルホスホリルコリン(以下、「MPC」という)は、高い生体適合性、抗タンパク質吸着能および高い親水性を有する化合物として知られている(非特許文献3、非特許文献4)。MPCを用いたオーラルケア剤として、口腔内の乾燥防止や刺激緩和に関する方法(特許文献3)、口腔内の微生物付着防止に関する方法(特許文献4)が開示されている。これまでの研究(非特許文献3、非特許文献4)や開発(特許文献4)から、MPCを用いることで口腔内のデンタルプラーク付着を防止することは可能であると考えられていたものの、実証はなされておらず、その方法や効果については知られていない状況であった。また、MPCを用いた口腔内のステインの沈着の防止や抑制に関する方法や効果は全く知られていない状況であった。 On the other hand, 2-methacryloyloxyethyl phosphorylcholine (hereinafter referred to as "MPC") is known as a compound having high biocompatibility, antiprotein adsorption ability and high hydrophilicity (Non-Patent Documents 3 and 4). .. As an oral care agent using MPC, a method for preventing dryness in the oral cavity and alleviating irritation (Patent Document 3) and a method for preventing microbial adhesion in the oral cavity (Patent Document 4) are disclosed. From previous studies (Non-Patent Document 3 and Non-Patent Document 4) and development (Patent Document 4), it was considered possible to prevent dental plaque adhesion in the oral cavity by using MPC. No proof has been made, and the method and effect are unknown. In addition, the method and effect of preventing or suppressing the deposition of stains in the oral cavity using MPC have not been known at all.
これより、従来の技術(特許文献1、特許文献2)では十分なデンタルプラーク・ステインの付着・沈着を防止できないために、歯面へのデンタルプラーク・ステインの付着・沈着を防止または抑制できるデンタルプラーク・ステイン付着防止剤およびこれを含有する口腔用組成物は、いまだ満足のいくものが得られていない状況であった。 As a result, since the conventional techniques (Patent Document 1 and Patent Document 2) cannot sufficiently prevent the adhesion and deposition of dental plaque and stain, the dental can prevent or suppress the adhesion and deposition of dental plaque and stain on the tooth surface. The plaque stain inhibitor and the oral composition containing the plaque stain inhibitor have not yet been obtained in a satisfactory manner.
上記の通り、本発明の課題は、デンタルプラーク・ステインの付着・沈着を防止または抑制できるデンタルプラーク・ステイン付着防止剤およびこれを含有する口腔用組成物を提供することである。 As described above, an object of the present invention is to provide a dental plaque / stain adhesion inhibitor capable of preventing or suppressing the adhesion / deposition of dental plaque / stain, and an oral composition containing the same.
本発明者らは、上記課題を解決するために鋭意検討を行った結果、2−(メタ)アクリロイルオキシエチルホスホリルコリンに基づく構成単位と、これとは異なる特定の構成単位とを特定割合で有する共重合体を、デンタルプラーク・ステイン付着防止剤として用いることで、上記の課題を解決することの知見を見出し、本発明を完成するに至った。 As a result of diligent studies to solve the above problems, the present inventors have a copolymer having a constituent unit based on 2- (meth) acryloyloxyethyl phosphorylcholine and a specific constituent unit different from the constituent unit in a specific ratio. We have found that the above-mentioned problems can be solved by using the polymer as a dental plaque / stain adhesion inhibitor, and have completed the present invention.
すなわち、本発明は以下の通りである。
1.重量平均分子量10,000〜5,000,000であり、
2−(メタ)アクリロイルオキシエチルホスホリルコリンに基づく構成単位(A)10〜90モル%と、
アルキル基含有(メタ)アクリル系単量体に基づく構成単位(B1)、4級アンモニウム基含有(メタ)アクリル系単量体に基づく構成単位(B2)および(メタ)アクリルアミド系単量体に基づく構成単位(B3)からなる群から選ばれる少なくとも1種の構成単位90〜10モル%と
を含有する共重合体を含有するデンタルプラーク・ステイン付着防止剤。
2.構成単位(A)が2−(メタ)アクリロイルオキシエチルホスホリルコリンに基づく構成単位であり、構成単位(B1)がブチルメタクリレートに基づく構成単位である、前項1に記載のデンタルプラーク・ステイン付着防止剤。
3.構成単位(A)が2−(メタ)アクリロイルオキシエチルホスホリルコリンに基づく構成単位であり、構成単位(B1)がステアリルメタクリレートに基づく構成単位である、前項1に記載のデンタルプラーク・ステイン付着防止剤。
4.構成単位(A)が2−(メタ)アクリロイルオキシエチルホスホリルコリンに基づく構成単位であり、構成単位(B2)が2−ヒドロキシ−3−メタクリロイルオキシプロピルトリメチルアンモニウムクロライドに基づく構成単位である、前項1に記載のデンタルプラーク・ステイン付着防止剤。
5.構成単位(A)が2−(メタ)アクリロイルオキシエチルホスホリルコリンに基づく構成単位であり、構成単位(B1)がステアリルメタクリレートに基づく構成単位であり、構成単位(B3)がN,N−ジメチルアミノプロピルアクリルアミドに基づく構成単位である、前項1に記載のデンタルプラーク・ステイン付着防止剤。
6.前記の1〜5に記載のデンタルプラーク・ステイン付着防止剤を0.001〜5.0w/v%と、水3.0〜99.9w/v%とを含有する口腔用組成物。
7.さらに、サッカリン、サッカリンナトリウム、グリセリン、スクラロース、キシリトール、マルチトール、ステビオサイド、アスパルテームからなる群(C)より選ばれる少なくとも1種の成分を含有する前記6に記載の口腔用組成物。
8.以下の工程を含む、デンタルプラーク・ステイン付着防止方法、
重量平均分子量10,000〜5,000,000であり、
2−(メタ)アクリロイルオキシエチルホスホリルコリンに基づく構成単位(A)10〜90モル%と、
アルキル基含有(メタ)アクリル系単量体に基づく構成単位(B1)、4級アンモニウム基含有(メタ)アクリル系単量体に基づく構成単位(B2)および(メタ)アクリルアミド系単量体に基づく構成単位(B3)からなる群から選ばれる少なくとも1種の構成単位90〜10モル%と
を含有する共重合体を含有するデンタルプラーク・ステイン付着防止剤又は該防止剤を含有する口腔用組成物を、ヒトを含む哺乳類の口腔に投与する工程。
9.重量平均分子量10,000〜5,000,000であり、
2−(メタ)アクリロイルオキシエチルホスホリルコリンに基づく構成単位(A)10〜90モル%と、
アルキル基含有(メタ)アクリル系単量体に基づく構成単位(B1)、4級アンモニウム基含有(メタ)アクリル系単量体に基づく構成単位(B2)および(メタ)アクリルアミド系単量体に基づく構成単位(B3)からなる群から選ばれる少なくとも1種の構成単位90〜10モル%と
を含有するデンタルプラーク・ステイン付着防止用共重合体。
10.重量平均分子量10,000〜5,000,000であり、
2−(メタ)アクリロイルオキシエチルホスホリルコリンに基づく構成単位(A)10〜90モル%と、
アルキル基含有(メタ)アクリル系単量体に基づく構成単位(B1)、4級アンモニウム基含有(メタ)アクリル系単量体に基づく構成単位(B2)および(メタ)アクリルアミド系単量体に基づく構成単位(B3)からなる群から選ばれる少なくとも1種の構成単位90〜10モル%と
を含有する共重合体をデンタルプラーク・ステイン付着防止剤の製造としての使用。
1. 1. The weight average molecular weight is 10,000 to 5,000,000.
2- (Meta) acryloyloxyethyl phosphorylcholine-based structural unit (A) 10-90 mol%,
Constituent unit based on alkyl group-containing (meth) acrylic monomer (B1), based on quaternary ammonium group-containing (meth) acrylic monomer-based structural unit (B2) and (meth) acrylamide-based monomer A dental plaque stain inhibitor containing a copolymer containing at least one structural unit 90 to 10 mol% selected from the group consisting of the structural unit (B3).
2. 2. The dental plaque / stain adhesion inhibitor according to item 1 above, wherein the constituent unit (A) is a constituent unit based on 2- (meth) acryloyloxyethyl phosphorylcholine, and the constituent unit (B1) is a constituent unit based on butyl methacrylate.
3. 3. The dental plaque / stain adhesion inhibitor according to item 1 above, wherein the constituent unit (A) is a constituent unit based on 2- (meth) acryloyloxyethyl phosphorylcholine, and the constituent unit (B1) is a constituent unit based on stearyl methacrylate.
4. The structural unit (A) is a structural unit based on 2- (meth) acryloyloxyethyl phosphorylcholine, and the structural unit (B2) is a structural unit based on 2-hydroxy-3-methacryloyloxypropyltrimethylammonium chloride. The dental plaque / stain inhibitor described.
5. The structural unit (A) is a structural unit based on 2- (meth) acryloyloxyethyl phosphorylcholine, the structural unit (B1) is a structural unit based on stearyl methacrylate, and the structural unit (B3) is N, N-dimethylaminopropyl. The dental plaque / stain adhesion inhibitor according to item 1 above, which is a structural unit based on acrylamide.
6. An oral composition containing 0.001 to 5.0 w / v% of the dental plaque / stain adhesion inhibitor according to 1 to 5 and 3.0 to 99.9 w / v% of water.
7. The oral composition according to 6 above, further containing at least one component selected from the group (C) consisting of saccharin, sodium saccharin, glycerin, sucralose, xylitol, maltitol, stebioside, and aspartame.
8. Dental plaque / stain prevention method, including the following steps,
The weight average molecular weight is 10,000 to 5,000,000.
2- (Meta) acryloyloxyethyl phosphorylcholine-based structural unit (A) 10-90 mol%,
Constituent unit based on alkyl group-containing (meth) acrylic monomer (B1), based on quaternary ammonium group-containing (meth) acrylic monomer-based structural unit (B2) and (meth) acrylamide-based monomer A dental plaque stain inhibitor containing a copolymer containing 90 to 10 mol% of at least one structural unit selected from the group consisting of the structural unit (B3), or an oral composition containing the inhibitor. To the oral cavity of mammals including humans.
9. The weight average molecular weight is 10,000 to 5,000,000.
2- (Meta) acryloyloxyethyl phosphorylcholine-based structural unit (A) 10-90 mol%,
Constituent unit based on alkyl group-containing (meth) acrylic monomer (B1), based on quaternary ammonium group-containing (meth) acrylic monomer-based structural unit (B2) and (meth) acrylamide-based monomer A copolymer for preventing adhesion of dental plaque / stain containing at least one structural unit 90 to 10 mol% selected from the group consisting of the structural unit (B3).
10. The weight average molecular weight is 10,000 to 5,000,000.
2- (Meta) acryloyloxyethyl phosphorylcholine-based structural unit (A) 10-90 mol%,
Constituent unit based on alkyl group-containing (meth) acrylic monomer (B1), based on quaternary ammonium group-containing (meth) acrylic monomer (B2) and (meth) acrylamide-based monomer Use of a copolymer containing 90 to 10 mol% of at least one structural unit selected from the group consisting of the structural unit (B3) for producing a dental plaque stain inhibitor.
本発明のデンタルプラーク・ステイン付着防止剤およびこれを含有する口腔用組成物は、歯面へのデンタルプラーク・ステインの付着・沈着を防止または抑制することができるため、歯の美観・健康維持に有用である。 The dental plaque / stain inhibitor of the present invention and the oral composition containing the same can prevent or suppress the adhesion / deposition of dental plaque / stain on the tooth surface, thus maintaining the aesthetics and health of the teeth. It is useful.
以下、本発明をさらに詳細に説明する。
本発明のデンタルプラーク・ステイン付着防止剤は、{2−(メタ)アクリロイルオキシエチルホスホリルコリンに基づく構成単位(A)と、アルキル基含有(メタ)アクリル系単量体に基づく構成単位(B1)、4級アンモニウム基含有(メタ)アクリル系単量体に基づく構成単位(B2)および(メタ)アクリルアミド系単量体に基づく構成単位(B3)からなる群から選ばれる少なくとも1種の構成単位とを含有する共重合体}を含有する。Hereinafter, the present invention will be described in more detail.
The dental plaque stain inhibitor of the present invention comprises {2- (meth) acryloyloxyethyl phosphorylcholine-based structural unit (A) and an alkyl group-containing (meth) acrylic monomer-based structural unit (B1). At least one structural unit selected from the group consisting of a structural unit (B2) based on a quaternary ammonium group-containing (meth) acrylic monomer and a structural unit (B3) based on a (meth) acrylamide-based monomer. Containing copolymer}.
<2−(メタ)アクリロイルオキシエチルホスホリルコリンに基づく構成単位(A)>
2−(メタ)アクリロイルオキシエチルホスホリルコリンに基づく構成単位(A)は、より具体的には下記の式(A)で表され、式(A')で表される単量体の重合によって得られる。<Constituent unit (A) based on 2- (meth) acryloyloxyethyl phosphorylcholine>
The structural unit (A) based on 2- (meth) acryloyloxyethyl phosphorylcholine is more specifically represented by the following formula (A) and is obtained by polymerization of a monomer represented by the formula (A'). ..
本発明に用いる共重合体は、分子鎖中に構成単位(A)を有することによって、デンタルプラークやステインの付着を防止する効果を発現することが出来る。
By having the structural unit (A) in the molecular chain, the copolymer used in the present invention can exhibit the effect of preventing the adhesion of dental plaque and stain.
本発明に用いる共重合体中の構成単位(A)の含有量は、10〜90モル%である。含有量が10モル%未満であるとデンタルプラーク・ステイン付着防止効果が期待出来ず、含有量が90モル%より多いと、MPCセグメントの有する超親水性のために歯面への吸着性に乏しくなり効果が望めなくなる。
2−(メタ)アクリロイルオキシエチルホスホリルコリンの好適な例として、2−メタクリロイルオキシエチルホスホリルコリンが挙げられる。
なお、本発明において「(メタ)アクリル」は、アクリルまたはメタアクリル(メタクリル)を意味し、「(メタ)アクリロイル」は、アクリロイルまたはメタアクリロイル(メタクリロイル)を意味し、「(メタ)アクリレート」は、アクリレートまたはメタアクリレート(メタクリレート)を意味する。The content of the structural unit (A) in the copolymer used in the present invention is 10 to 90 mol%. If the content is less than 10 mol%, the effect of preventing dental plaque / stain adhesion cannot be expected, and if the content is more than 90 mol%, the adsorption to the tooth surface is poor due to the superhydrophilicity of the MPC segment. The effect cannot be expected.
Preferable examples of 2- (meth) acryloyloxyethyl phosphorylcholine include 2-methacryloyloxyethyl phosphorylcholine.
In the present invention, "(meth) acrylic" means acrylic or methacrylic (methacryl), "(meth) acryloyl" means acryloyl or meta-acryloyl (methacryloyl), and "(meth) acrylate" means. , Acryloyl or methacrylate (methacrylate).
<アルキル基含有(メタ)アクリル系単量体に基づく構成単位(B1)>
アルキル基含有(メタ)アクリル系単量体に基づく構成単位(B1)は、より具体的には下記の式(B1)で表され、式(B1')で表される単量体の重合によって得られる。
本発明に用いる共重合体は、分子鎖中に構成単位(B1)を有することによって、共重合体の歯面への吸着性をより高めることが出来る。<Constituent unit based on alkyl group-containing (meth) acrylic monomer (B1)>
The structural unit (B1) based on the alkyl group-containing (meth) acrylic monomer is more specifically represented by the following formula (B1), and is formed by the polymerization of the monomer represented by the formula (B1'). can get.
By having the constituent unit (B1) in the molecular chain, the copolymer used in the present invention can further enhance the adsorptivity of the copolymer to the tooth surface.
式(B1)および式(B1')において、R2は水素原子もしくはメチル基のいずれでも良いが、好ましくはメチル基である。R3は炭素数4〜18の直鎖状または分岐状のアルキル基のいずれでも良い。
具体的には、炭素数4〜18の直鎖状のアルキル基としては、n−ブチル基、n−ペンチル基、n−ヘキシル基、n−ヘプチル基、n−オクチル基、n−ノニル基、n−デシル基、n−ウンデシル基、n−ドデシル基、n−トリデシル基、n−テトラデシル基、n−ペンダデシル基、n−ヘキサデシル基、n−ヘプタデシル基、n−オクタデシル基が挙げられる。炭素数4〜18の分岐状のアルキル基としては、t−ブチル基、イソブチル基、イソペンチル基、t−ペンチル基、ネオペンチル基、イソヘキシル基、イソヘプチル基、イソオクチル基、イソノニル基、イソデシル基、イソウンデシル基、イソドデシル基、イソトリデシル基、イソテトラデシル基、イソペンタデシル基、イソヘキサデシル基、イソヘプタデシル基、イソオクタデシル基が挙げられる。
共重合体の歯面への吸着性の観点から、n−ブチル基、n−ドデシル基、n−オクタデシル基が好ましい。In the formula (B1) and the formula (B1'), R 2 may be either a hydrogen atom or a methyl group, but is preferably a methyl group. R 3 may be either a linear or branched alkyl group having 4 to 18 carbon atoms.
Specifically, as the linear alkyl group having 4 to 18 carbon atoms, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, etc. Examples thereof include n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pendadecyl group, n-hexadecyl group, n-heptadecyl group and n-octadecyl group. The branched alkyl group having 4 to 18 carbon atoms includes a t-butyl group, an isobutyl group, an isopentyl group, a t-pentyl group, a neopentyl group, an isohexyl group, an isoheptyl group, an isooctyl group, an isononyl group, an isodecyl group and an isoundecyl group. , Isododecyl group, isotridecyl group, isotetradecyl group, isopentadecyl group, isohexadecyl group, isoheptadecyl group, isooctadecyl group.
From the viewpoint of the adsorptivity of the copolymer to the tooth surface, an n-butyl group, an n-dodecyl group and an n-octadecyl group are preferable.
構成単位(B1)を満たす構造を有していれば、共重合体の歯面への吸着性を損なうことが無いため、いずれでも用いることができるが、共重合体の歯面への吸着性をより高める観点から、アルキル基含有(メタ)アクリル系単量体の好適な例として、ブチル(メタ)アクリレート、ラウリル(メタ)アクリレート、ステアリル(メタ)アクリレート、2−エチルヘキシル(メタ)アクリレートが挙げられる。 Any structure can be used as long as it has a structure satisfying the structural unit (B1) because it does not impair the adsorptivity of the copolymer to the tooth surface. However, the adsorptivity of the copolymer to the tooth surface Preferable examples of the alkyl group-containing (meth) acrylic monomer from the viewpoint of further enhancing the above are butyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, and 2-ethylhexyl (meth) acrylate. Be done.
<4級アンモニウム基含有(メタ)アクリル系単量体に基づく構成単位(B2)>
4級アンモニウム基含有(メタ)アクリル系単量体に基づく構成単位(B2)は、より具体的には下記の式(B2)で表され、式(B2')で表される単量体の重合によって得られる。
本発明に用いる共重合体は、分子鎖中に構成単位(B2)を有することによって、共重合体の歯面への吸着性をより高めることが出来る。<Constituent unit (B2) based on quaternary ammonium group-containing (meth) acrylic monomer>
The structural unit (B2) based on the quaternary ammonium group-containing (meth) acrylic monomer is more specifically represented by the following formula (B2), and the monomer represented by the formula (B2'). Obtained by polymerization.
By having the constituent unit (B2) in the molecular chain, the copolymer used in the present invention can further enhance the adsorptivity of the copolymer to the tooth surface.
式(B2)および式(B2')において、R4は水素原子もしくはメチル基のいずれでも良いが、好ましくはメチル基である。R5、R6およびR7は、それぞれ独立に、水素原子または炭素数1〜8のアルキル基を示し、アルキル基は直鎖状、分岐状および環状のいずれであっても良い。In the formula (B2) and the formula (B2'), R 4 may be either a hydrogen atom or a methyl group, but is preferably a methyl group. R 5 , R 6 and R 7 each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and the alkyl group may be linear, branched or cyclic.
具体的には、R5、R6およびR7としてメチル基、エチル基、プロピル基、イソプロピル基、n−ブチル基、イソブチル基、sec−ブチル基、tert−ブチル基、n−ペンチル基、イソペンチル基、n−ヘキシル基、イソヘキシル基、n−ヘプチル基、イソヘプチル基、n−オクチル基、イソオクチル基、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などが挙げられる。
R5、R6およびR7として好ましくはメチル基、エチル基、プロピル基、イソプロピル基であり、より好ましくはメチル基である。Specifically, R 5 , R 6 and R 7 include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group and an isopentyl. Examples thereof include a group, an n-hexyl group, an isohexyl group, an n-heptyl group, an isoheptyl group, an n-octyl group, an isooctyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl group.
R 5 , R 6 and R 7 are preferably a methyl group, an ethyl group, a propyl group and an isopropyl group, and more preferably a methyl group.
X−としては、例えば、フッ素イオン、臭素イオン、塩素イオン(クロライドイオン)などのハロゲンイオン、硫酸イオン、メチル硫酸イオンなどの酸残基が挙げられる。好ましくは、ハロゲンイオンである。
共重合体の歯面への吸着性をより高める観点から、4級アンモニウム基含有(メタ)アクリル系単量体の好適な例として、2−ヒドロキシ−3−(メタ)アクリロイルオキシプロピルトリメチルアンモニウムクロライドなどが挙げられる。Examples of X − include halogen ions such as fluorine ion, bromine ion and chlorine ion (chloride ion), and acid residues such as sulfate ion and methyl sulfate ion. It is preferably a halogen ion.
2-Hydroxy-3- (meth) acryloyloxypropyltrimethylammonium chloride is a suitable example of a quaternary ammonium group-containing (meth) acrylic monomer from the viewpoint of further enhancing the adsorptivity of the copolymer to the tooth surface. And so on.
<(メタ)アクリルアミド系単量体に基づく構成単位(B3)>
(メタ)アクリルアミド系単量体に基づく構成単位(B3)は、より具体的には下記の式(B3)で表され、式(B3')で表される単量体の重合によって得られる。
本発明に用いる共重合体は、分子鎖中に構成単位(B3)を有することによって、共重合体を高分子量化し、共重合体の歯面への密着性をより高めることが出来る。<Constituent unit based on (meth) acrylamide-based monomer (B3)>
The structural unit (B3) based on the (meth) acrylamide-based monomer is more specifically represented by the following formula (B3), and is obtained by polymerizing the monomer represented by the formula (B3').
By having the structural unit (B3) in the molecular chain, the copolymer used in the present invention can increase the molecular weight of the copolymer and further enhance the adhesion of the copolymer to the tooth surface.
式(B3)および式(B3')において、R8は水素原子もしくはメチル基のいずれでも良いが、好ましくは水素原子である。R9およびR10は、それぞれ独立に、水素原子または炭素数1〜6のアルキル基を示し、アルキル基は直鎖状、分岐状および環状のいずれであっても良い。具体的には、メチル基、エチル基、プロピル基、イソプロピル基、n−ブチル基、イソブチル基、sec−ブチル基、tert−ブチル基、n−ペンチル基、イソペンチル基、n−ヘキシル基、イソヘキシル基、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基などが挙げられる。
R9およびR10として好ましくは、水素原子、メチル基、エチル基、プロピル基もしくはイソプロピル基であり、より好ましくはメチル基である。
共重合体を高分子量化し、共重合体の歯面への密着性をより高める観点から、(メタ)アクリルアミド系単量体の好適な例として、N,N−ジメチルアミノプロピル(メタ)アクリルアミド等が挙げられる。In formulas (B3) and (B3'), R 8 may be either a hydrogen atom or a methyl group, but is preferably a hydrogen atom. R 9 and R 10 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may be linear, branched or cyclic. Specifically, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, n-hexyl group, isohexyl group. , Cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and the like.
R 9 and R 10 are preferably a hydrogen atom, a methyl group, an ethyl group, a propyl group or an isopropyl group, and more preferably a methyl group.
From the viewpoint of increasing the molecular weight of the copolymer and further enhancing the adhesion of the copolymer to the tooth surface, N, N-dimethylaminopropyl (meth) acrylamide and the like are suitable examples of the (meth) acrylamide-based monomer. Can be mentioned.
本発明に用いる共重合体は、分子鎖中に(B1)、(B2)および(B3)からなる群から選択される少なくとも1つの構成単位を有する。本発明に用いる共重合体は、分子鎖中に(B1)、(B2)および(B3)からなる群から選択されるいずれか1つの構成単位のみを有していてもよく、(B1)、(B2)および(B3)からなる群から選択される2つの構成単位(例えば、(B1)および(B2)の組み合わせ、(B2)および(B3)の組み合わせ、(B3)および(B1)の組み合わせ)を有していてもよく、(B1)、(B2)および(B3)の全ての構成単位を有していても良い。 The copolymer used in the present invention has at least one structural unit selected from the group consisting of (B1), (B2) and (B3) in the molecular chain. The copolymer used in the present invention may have only one structural unit selected from the group consisting of (B1), (B2) and (B3) in the molecular chain, and (B1), Two building blocks selected from the group consisting of (B2) and (B3) (eg, a combination of (B1) and (B2), a combination of (B2) and (B3), a combination of (B3) and (B1). ), And may have all the structural units of (B1), (B2) and (B3).
本発明に用いる共重合体は、分子鎖中に構成単位(B1)〜(B3)を有することによって、共重合体の歯面への吸着性、密着性が高くなる。さらに(B1)〜(B3)だけでなく、構成単位(A)をも同一高分子鎖中に有することによって、本発明に用いる共重合体は、歯面への吸着性を有するデンタルプラーク・ステイン付着防止剤となる。本発明に用いる共重合体中の構成単位(B1)〜(B3)の含有量{(B1)〜(B3)のうち1つの構成単位のみを含有する場合は当該構成単位の含有量、(B1)〜(B3)のうち2つまたは3つの構成単位を含有する場合は、それらの構成単位の含有量の合計}は10〜90モル%であり、好ましくは10〜80モル%であり、より好ましくは10〜70モル%である。含有量が10モル%未満であると共重合体の親水性が高くなり、歯面への吸着性に乏しくなり、デンタルプラーク・ステイン付着防止効果が望めなくなる恐れがあり、含有量が90モル%より多いと水への溶解性が低下し、口腔用組成物を製することが困難となる恐れがある。 By having the structural units (B1) to (B3) in the molecular chain, the copolymer used in the present invention has high adsorptivity and adhesion to the tooth surface of the copolymer. Furthermore, by having not only (B1) to (B3) but also the constituent unit (A) in the same polymer chain, the copolymer used in the present invention is a dental plaque stain having adsorptivity to the tooth surface. It acts as an anti-adhesion agent. Content of structural units (B1) to (B3) in the copolymer used in the present invention {When only one structural unit of (B1) to (B3) is contained, the content of the structural unit, (B1) ) To (B3), when two or three constituent units are contained, the total content of those constituent units} is 10 to 90 mol%, preferably 10 to 80 mol%, and more. It is preferably 10 to 70 mol%. If the content is less than 10 mol%, the hydrophilicity of the copolymer becomes high, the adsorptivity to the tooth surface becomes poor, and the effect of preventing dental plaque / stain adhesion may not be expected, and the content is 90 mol%. If it is more than that, the solubility in water is lowered, and it may be difficult to prepare an oral composition.
本発明に用いる共重合体の分子鎖中に含まれる、構成単位(A)と構成単位(B1)〜(B3)の組み合わせの好適な例は、デンタルプラーク・ステイン付着防止効果と共重合体の歯面への吸着性・密着性の観点から、以下の組み合わせが挙げられる。
2−(メタ)アクリロイルオキシエチルホスホリルコリン(A)およびブチル(メタ)アクリレート(B1);
2−(メタ)アクリロイルオキシエチルホスホリルコリン(A)およびステアリル(メタ)アクリレート(B1);
2−(メタ)アクリロイルオキシエチルホスホリルコリン(A)および2−ヒドロキシ−3−(メタ)アクリロイルオキシプロピルトリメチルアンモニウムクロライド(B2);ならびに、
2−(メタ)アクリロイルオキシエチルホスホリルコリン(A)、N,N−ジメチルアミノプロピル(メタ)アクリルアミド(B3)およびステアリル(メタ)アクリレート(B1)。A preferable example of the combination of the structural unit (A) and the structural units (B1) to (B3) contained in the molecular chain of the copolymer used in the present invention is the dental plaque / stain adhesion preventing effect and the copolymer. From the viewpoint of adsorption and adhesion to the tooth surface, the following combinations can be mentioned.
2- (Meta) acryloyloxyethyl phosphorylcholine (A) and butyl (meth) acrylate (B1);
2- (Meta) acryloyloxyethyl phosphorylcholine (A) and stearyl (meth) acrylate (B1);
2- (Meta) acryloyloxyethyl phosphorylcholine (A) and 2-hydroxy-3- (meth) acryloyloxypropyltrimethylammonium chloride (B2);
2- (Meta) acryloyloxyethyl phosphorylcholine (A), N, N-dimethylaminopropyl (meth) acrylamide (B3) and stearyl (meth) acrylate (B1).
本発明に用いる共重合体は、構成単位(A)および構成単位(B1)〜(B3)以外の構成単位を含んでいても良いが、好ましくは、構成単位(A)および、構成単位(B1)、(B2)並びに(B3)からなる群より選択される1つ、2つまたは3つの構成単位からなる。 The copolymer used in the present invention may contain a structural unit other than the structural unit (A) and the structural units (B1) to (B3), but preferably the structural unit (A) and the structural unit (B1). ), (B2) and (B3) consist of one, two or three structural units selected from the group.
本発明に用いられる共重合体は、特開平11−035605の方法に従って重合を行い得たMPCポリマー(1)、特開2004−196868の方法に従って重合を行い得たMPCポリマー(2)、特開2004−196868の方法に従って重合を行い得たMPCポリマー(3)、特開2004−189678の方法に従って重合を行い得たMPCポリマー(4)および特開2013−018749の方法に従って重合を行い得たMPCポリマー(5)を用いることが出来る。 The copolymer used in the present invention includes an MPC polymer (1) that can be polymerized according to the method of JP-A-11-305605, an MPC polymer (2) that can be polymerized according to the method of JP-A-2004-196868, and JP-A. MPC polymer (3) that could be polymerized according to the method of 2004-196868, MPC polymer (4) that could be polymerized according to the method of JP-A-2004-189678, and MPC that could be polymerized according to the method of JP2013-018479. The polymer (5) can be used.
本発明に用いる共重合体の重量平均分子量は10,000〜5,000,000であり、好ましくは、20,000〜1,000,000である。重量平均分子量が10,000未満であると歯面への吸着性が低下し、デンタルプラーク・ステイン付着防止効果が望めなくなり、重量平均分子量が5,000,000より大きいと粘度が急激に上昇し、口腔用組成物を製することが困難となる恐れがある。 The weight average molecular weight of the copolymer used in the present invention is 10,000 to 5,000,000, preferably 20,000 to 1,000,000. If the weight average molecular weight is less than 10,000, the adsorptivity to the tooth surface is lowered, the effect of preventing dental plaque / stain adhesion cannot be expected, and if the weight average molecular weight is larger than 5,000,000, the viscosity sharply increases. , It may be difficult to produce an oral composition.
本発明のデンタルプラーク・ステイン付着防止剤または該防止剤を含有する口腔用組成物に含有する前記共重合体の配合量は、当該共重合体を防止剤または組成物全体に対して、0.001〜5.0w/v%である。配合量が0.001w/v%未満であると、デンタルプラーク・ステイン付着防止効果が得られない恐れがあり、配合量が5.0w/v%以上であっても、添加量に見合った効果が得られない。
加えて、本発明のデンタルプラーク・ステイン付着防止剤または該防止剤を含有する口腔用組成物の濃度は、より好ましくは、0.01〜5.0 W/V%であり、さらに好ましくは0.05〜5.0 W/V%である。The blending amount of the copolymer contained in the dental plaque / stain adhesion inhibitor or the oral composition containing the inhibitor of the present invention is such that the copolymer is used as an inhibitor or the composition as a whole. It is 001 to 5.0 w / v%. If the blending amount is less than 0.001 w / v%, the effect of preventing dental plaque / stain adhesion may not be obtained, and even if the blending amount is 5.0 w / v% or more, the effect commensurate with the added amount. Cannot be obtained.
In addition, the concentration of the dental plaque stain inhibitor or the oral composition containing the inhibitor of the present invention is more preferably 0.01 to 5.0 W / V%, still more preferably 0. .05-5.0 W / V%.
本発明に用いる(C)群としては、サッカリン、サッカリンナトリウム、グリセリン、スクラロース、キシリトール、マルチトール、ステビオサイド、アスパルテームである。これら(C)群の成分を添加することで歯面へのデンタルプラークやステインがより付着・沈着しにくくなるとともに、さらに、一度歯面へ付着・沈着したデンタルプラークやステインが落ち易くなる。本発明の(C)群の含有量は、通常、0.001〜10.0w/v%であれば良い。よりデンタルプラーク・ステイン付着防止効果を高める観点から、0.002〜10.0w/v%が好ましく、さらに好ましくは、0.003〜8.0w/v%である。 Group (C) used in the present invention includes saccharin, sodium saccharin, glycerin, sucralose, xylitol, maltitol, stebioside, and aspartame. By adding the components of group (C), dental plaque and stain on the tooth surface are less likely to adhere and deposit, and further, dental plaque and stain once adhered and deposited on the tooth surface are easily removed. The content of group (C) of the present invention is usually 0.001 to 10.0 w / v%. From the viewpoint of further enhancing the effect of preventing dental plaque / stain adhesion, 0.002 to 10.0 w / v% is preferable, and 0.003 to 8.0 w / v% is more preferable.
さらに、本発明のデンタルプラーク・ステイン付着防止剤または該防止剤を含有する口腔用組成物は、共重合体や(C)群成分以外にも必要に応じて一般に口腔用組成物に使用できる緩衝剤、湿潤剤、薬剤、界面活性剤、防腐殺菌剤、粘結剤、香料、有機酸、酸化防止剤、安定剤、金属封鎖剤、溶剤等を配合することができる。
緩衝剤としては特に限定されないが、クエン酸、リン酸、リンゴ酸、グルコン酸およびこれらの塩が挙げられ、0.001w/v%〜3.0w/v%で使用されることが望ましい。Further, the dental plaque / stain adhesion inhibitor or the oral composition containing the inhibitor of the present invention is a buffer that can be generally used for an oral composition in addition to the copolymer and the group (C) component, if necessary. Agents, wetting agents, chemicals, surfactants, antiseptic and bactericidal agents, binders, fragrances, organic acids, antioxidants, stabilizers, metal sequestering agents, solvents and the like can be blended.
The buffer is not particularly limited, and examples thereof include citric acid, phosphoric acid, malic acid, gluconic acid and salts thereof, and it is desirable to use them at 0.001 w / v% to 3.0 w / v%.
湿潤剤は、プロピレングリコール、ブチレングリコール、ペンチレングリコール、ジプロピレングリコール、ポリエチレングリコール、マンニトール、エリスリトールなどの多価アルコールが挙げられ、1.0w/v%〜50.0w/v%で使用されることが望ましい。
薬剤としては、特に限定されないが、アズレンスルホン酸ナトリウム、イプシロン−アミノカプロン酸、アラントイン、アラントインクロルヒドロキシアルミニウム、アラントインヒドロキシアルミニウム、エピジヒドロキシコレステリン、ジヒドロコレステロール、塩化ナトリウム、硝酸カリウム、乳酸アルミニウム、塩化亜鉛、グリチルリチン酸およびその塩、β−グリチルリチン酸、イソプロピルメチルフェノール、塩化セチルピリジニウム、塩化デカリウム、塩化ベンザルコニウム、塩化ベンゼトニウム、塩酸アルキルジアミノエチルグリシン、塩酸クロルヘキシジン、グルコン酸クロルヘキシジン、トリクロサン、1、8−シネオール、アスコルビン酸およびその塩、塩酸ピリドキシン、酢酸dl−α−トコフェロール、ニコチン酸dl−α−トコフェロール、ゼオライト、ピロリン酸二水素二ナトリウム、ピロリン酸ナトリウム、リン酸1水素ナトリウム、リン酸三ナトリウム、ポリリン酸ナトリウム、フッ化ナトリウム、モノフルオロリン酸ナトリウム、ポリエチレングリコール、ポリビニルピロリドン、ポビドンヨード、塩化リゾチーム、銅クロロフィリンナトリウム、ヒノキチオール、ポリオキシエチレンラウリルエーテル(8〜10E.O.)、ラウロイルサルコシンナトリウム、トラネキサム酸、サリチル酸メチル、l−メントールなどが挙げられる。Examples of the wetting agent include polyhydric alcohols such as propylene glycol, butylene glycol, pentylene glycol, dipropylene glycol, polyethylene glycol, mannitol and erythritol, and are used at 1.0 w / v% to 50.0 w / v%. Is desirable.
The drug is not particularly limited, but is limited to sodium azulene sulfonate, epsilon-aminocaproic acid, allantin, allantinchlorohydroxyaluminum, allantinhydroxyaluminum, epidihydroxycholesterin, dihydrocholesterol, sodium chloride, potassium nitrate, aluminum lactate, zinc chloride, glycyrrhizin. Acids and salts thereof, β-glycyrrhizinic acid, isopropylmethylphenol, cetylpyridinium chloride, depotassium chloride, benzalconium chloride, benzethonium chloride, alkyldiaminoethylglycine hydrochloride, chlorhexidine hydrochloride, chlorhexidine gluconate, triclosan, 1,8-cineole, Ascorbic acid and its salts, pyridoxin hydrochloride, dl-α-tocopherol acetate, dl-α-tocopherol nicotinate, zeolite, disodium dihydrogen pyrophosphate, sodium pyrophosphate, sodium monohydrogen phosphate, trisodium phosphate, polyphosphate Sodium, sodium fluoride, sodium monofluorophosphate, polyethylene glycol, polyvinylpyrrolidone, povidone iodine, lysozyme chloride, sodium copper chlorophyllin, hinokithiol, polyoxyethylene lauryl ether (8-10EO), sodium lauroyl sarcosin, tranexamic acid, Examples thereof include methyl salicylate and l-menthol.
界面活性剤としては特に限定はされないが、ポリオキシエチレン硬化ヒマシ油、ソルビタン脂肪酸エチレン付加物、ポリグリセリン脂肪酸エステル、アシルアミノ酸塩、脂肪酸アミノプロピルベタイン、脂肪酸アミドベタインなどが挙げられ、特にポリオキシエチレン硬化ヒマシ油、ソルビタン脂肪酸エチレン付加物を0.05w/v%〜2.0w/v%で使用されることが好ましい。 The surfactant is not particularly limited, and examples thereof include polyoxyethylene hydrogenated castor oil, sorbitan fatty acid ethylene adduct, polyglycerin fatty acid ester, acyl amino acid salt, fatty acid aminopropyl betaine, and fatty acid amide betaine, and in particular, polyoxyethylene. Hardened castor oil and sorbitan fatty acid ethylene adduct are preferably used at 0.05 w / v% to 2.0 w / v%.
防腐殺菌剤としては特に限定はされないが、塩酸ポリヘキサニド、ヒノキチオール、安息香酸およびこの塩、パラベン類などが挙げられ、通常配合量は0.01w/v%〜1.0w/v%である。 The antiseptic bactericide is not particularly limited, and examples thereof include polyhexanide hydrochloride, hinokitiol, benzoic acid and salts thereof, parabens, etc., and the usual blending amount is 0.01 w / v% to 1.0 w / v%.
粘結剤としては特に限定はされないが、プルラン、ゼラチン、メチルセルロース、ヒドロキシエチルセルロース、ヒドロキシプロピルセルロース、ヒドロキシプロピルメチルセルロース、カルボキシメチルセルロースなどのセルロース系粘稠化剤、ヒアルロン酸およびその塩、コンドロイチン硫酸およびその塩、アルギン酸およびその塩、ジュランガム、キサンタンガムなどのような多糖類などが挙げられる。 The binder is not particularly limited, but is a cellulosic thickener such as pullulan, gelatin, methyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose, carboxymethyl cellulose, hyaluronic acid and its salt, chondroitin sulfate and its salt. , Alginic acid and its salts, polysaccharides such as pullulan gum, xanthan gum and the like.
香料としては特に限定はされないが、ペパーミント油、スペアミント油、アニス油、ユーカリ油、ウィンターグリーン油、カシア油、クローブ油、タイム油、セージ油、レモン油、オレンジ油、ハッカ油、カルダモン油、コリアンダー油、マンダリン油、ライム油、ラベンダー油、ローズマリー油、ローレル油、カモミル油、キャラウェイ油、マジョラム油、ベイ油、レモングラス油、オリガナム油、パインニードル油、ネロリ油、ローズ油、ジャスミン油、グレープフルーツ油、スウィーティー油、柚油、イリスコンクリート、アブソリュートペパーミント、アブソリュートローズ、オレンジフラワー等の天然香料、およびこれら天然香料の加工処理(前溜部カット、後溜部カット、分留、液液抽出、エッセンス化、粉末香料化等)した香料、および、l−メントール、カルボン、アネトール、シネオール、サリチル酸メチル、シンナミックアルデヒド、オイゲノール、3−l−メントキシプロパン−1、2−ジオール、チモール、リナロール、リナリールアセテート、リモネン、メントン、メンチルアセテート、N−置換−パラメンタン−3−カルボキサミド、ピネン、オクチルアルデヒド、シトラール、プレゴン、カルビールアセテート、アニスアルデヒド、エチルアセテート、エチルブチレート、アリルシクロヘキサンプロピオネート、メチルアンスラニレート、エチルメチルフェニルグリシデート、バニリン、ウンデカラクトン、ヘキサナール、ブタノール、イソアミルアルコール、ヘキセノール、ジメチルサルファイド、シクロテン、フルフラール、トリメチルピラジン、エチルラクテート、エチルチオアセテート等の単品香料、さらに、ストロベリーフレーバー、アップルフレーバー、バナナフレーバー、パイナップルフレーバー、グレープフレーバー、マンゴーフレーバー、バターフレーバー、ミルクフレーバー、フルーツミックスフレーバー、トロピカルフルーツフレーバー等の調合香料などが挙げられ、0.001w/v%〜1.0w/v%で使用されることが望ましい。
有機酸としては特に限定はされないが、リンゴ酸、クエン酸、酒石酸、アスコルビン酸などが挙げられる。
酸化防止剤としては特に限定はされないが、ビタミンE、ビタミンC、茶抽出物、ローズマリー抽出物などが挙げられる。
安定剤としては特に限定はされないが、亜硫酸ナトリウム、ピロ亜硫酸ナトリウム、亜硫酸水素ナトリウム、ブチルヒドロキシトルエン、没食子酸プロピル、ブチルヒドロキシアリール等が挙げられる。The fragrance is not particularly limited, but peppermint oil, spearmint oil, anise oil, eucalyptus oil, winter green oil, cassia oil, clove oil, thyme oil, sage oil, lemon oil, orange oil, peppermint oil, cardamon oil, coriander. Oil, mandarin oil, lime oil, lavender oil, rosemary oil, laurel oil, camomill oil, caraway oil, majorum oil, bay oil, lemongrass oil, origanum oil, pine needle oil, neroli oil, rose oil, jasmine oil , Grapefruit oil, sweetie oil, yuzu oil, iris concrete, absolute peppermint, absolute rose, orange flower and other natural fragrances, and processing of these natural fragrances (front reservoir cut, rear reservoir cut, distilling, liquid extraction) , Essence, powdered fragrance, etc.), and l-menthol, carboxylic, anetol, cineol, methyl salicylate, synamic aldehyde, eugenol, 3-l-mentoxypropan-1,2-diol, timol, linalol , Linaryl Acetate, Limonen, Menton, Menthyl Acetate, N-Substituted Paramentan-3-Carboxamide, Pinen, Octylaldehyde, Citral, Pregon, Calvia Acetate, Anisaldehyde, Ethyl Acetate, Ethyl Butyrate, Allyl Cyclohexane Propionate , Methylanthranilate, ethylmethylphenylglycidate, vanillin, undecalactone, hexanal, butanol, isoamyl alcohol, hexenol, dimethylsulfide, cycloten, furfural, trimethylpyrazine, ethyllactate, ethylthioacetate, etc. Blended flavors such as strawberry flavor, apple flavor, banana flavor, pineapple flavor, grape flavor, mango flavor, butter flavor, milk flavor, fruit mix flavor, tropical fruit flavor, etc., 0.001w / v% to 1.0w It is desirable to use at / v%.
The organic acid is not particularly limited, and examples thereof include malic acid, citric acid, tartaric acid, and ascorbic acid.
The antioxidant is not particularly limited, and examples thereof include vitamin E, vitamin C, tea extract, and rosemary extract.
The stabilizer is not particularly limited, and examples thereof include sodium sulfite, sodium pyrosulfite, sodium hydrogen sulfite, butylhydroxytoluene, propyl gallate, and butyl hydroxyaryl.
金属封鎖剤として特に限定はされないが、1−ヒドロキシエタン−1,1−ジフォスホン酸、1−ヒドロキシエタン−1,1−ジフォスホン酸四ナトリウム塩、エデト酸二ナトリウム、エデト酸三ナトリウム、エデト酸四ナトリウム、クエン酸ナトリウム、ポリリン酸ナトリウム、メタリン酸ナトリウム、グルコン酸、リン酸、クエン酸、アスコルビン酸、コハク酸、エデト酸、エチレンジアミンヒドロキシエチル三酢酸3ナトリウム等を挙げることが出来る。
溶剤として特に限定はされないが、水、エタノールを挙げることができる。The metal sequestering agent is not particularly limited, but 1-hydroxyethane-1,1-diphosphonic acid, 1-hydroxyethane-1,1-diphosphonic acid tetrasodium salt, disodium edetate, trisodium edetate, tetra-edetate Examples thereof include sodium, sodium citrate, sodium polyphosphate, sodium metaphosphate, gluconic acid, phosphoric acid, citric acid, ascorbic acid, succinic acid, edetic acid, and trisodium ethylenediaminehydroxyethyl triacetate.
The solvent is not particularly limited, and examples thereof include water and ethanol.
本発明のデンタルプラーク・ステイン付着防止剤の具体的な製品形態としては、口腔用組成物として使用することが好ましく、次のようなものを例示することが出来る。すなわち、練り歯磨き、液体ハミガキ、洗口液、含そう薬、口腔清涼化剤などが挙げられる。口腔用組成物としては、中でも、練り歯磨き、液体ハミガキ、洗口液、含そう薬とすることが好ましい。
本発明のデンタルプラーク・ステイン付着防止剤は、練り歯磨き、液体ハミガキ、洗口液や含そう薬等として、ヒトの歯へ適用してその効果を発現させることが好ましいが、義歯や歯科材料へも適用することが出来る。As a specific product form of the dental plaque / stain adhesion inhibitor of the present invention, it is preferable to use it as an oral composition, and the following can be exemplified. That is, toothpaste, liquid toothpaste, mouthwash, mouthwash, oral refreshing agent and the like can be mentioned. The oral composition is preferably a toothpaste, a liquid toothpaste, a mouthwash, or a mouthwash.
The dental plaque / stain adhesion inhibitor of the present invention is preferably applied to human teeth as a toothpaste, liquid toothpaste, mouthwash, mouthwash, etc. to exert its effect, but is applied to dentures and dental materials. Can also be applied.
本発明は、以下の工程を含む、デンタルプラーク・ステイン付着防止方法も対象とする。
重量平均分子量10,000〜5,000,000であり、
2−(メタ)アクリロイルオキシエチルホスホリルコリンに基づく構成単位(A)10〜90モル%と、
アルキル基含有(メタ)アクリル系単量体に基づく構成単位(B1)、4級アンモニウム基含有(メタ)アクリル系単量体に基づく構成単位(B2)および(メタ)アクリルアミド系単量体に基づく構成単位(B3)からなる群から選ばれる少なくとも1種の構成単位90〜10モル%と
を含有する共重合体を含有するデンタルプラーク・ステイン付着防止剤又は該防止剤を含有する口腔用組成物を、ヒトを含む哺乳類の口腔に投与する工程。
The weight average molecular weight is 10,000 to 5,000,000.
2- (Meta) acryloyloxyethyl phosphorylcholine-based structural unit (A) 10-90 mol%,
Constituent unit based on alkyl group-containing (meth) acrylic monomer (B1), based on quaternary ammonium group-containing (meth) acrylic monomer-based structural unit (B2) and (meth) acrylamide-based monomer A dental plaque stain inhibitor containing a copolymer containing 90 to 10 mol% of at least one structural unit selected from the group consisting of the structural unit (B3), or an oral composition containing the inhibitor. To the oral cavity of mammals including humans.
本発明のデンタルプラーク・ステイン付着防止方法は、特に限定されないが、例えば、本発明のデンタルプラーク・ステイン付着防止剤を含有する口腔用組成物(液体ハミガキ)1回あたり5〜50 mLを1日あたり1〜10回、1〜8回、1〜6回、1〜4回、1〜3回(好ましくは、朝、昼、晩)、1回あたり5秒以上口に含み含そうすることが可能である。
また、別の態様では、例えば、本発明のデンタルプラーク・ステイン付着防止剤を含有する口腔用組成物(練り歯磨き剤)1回あたり0.01〜2 gを使用して、1日あたり1〜10回、1〜8回、1〜6回、1〜4回、1〜3回(好ましくは、朝、昼、晩)、ブラッシングすることが可能である。
デンタルプラーク・ステイン付着防止方法の対象は、特に限定されないが、ヒトを含む哺乳類を対象とする。なお、前記ヒトを含む哺乳類が、取外し可能な義歯又は歯科材料を装着している場合、取り外した状態の義歯又は歯科材料も対象とすることができる。
例えば、本発明のデンタルプラーク・ステイン付着防止剤を水やエタノール等に溶解した溶液に、義歯又は歯科材料を、1日あたり1〜10回、1〜8回、1〜6回、1〜4回、1〜3回、1回あたり30秒以上浸漬することを例示することができる。The method for preventing dental plaque / stain adhesion of the present invention is not particularly limited, but for example, 5 to 50 mL of an oral composition (liquid toothpaste) containing the dental plaque / stain adhesion inhibitor of the present invention is administered daily. 1 to 10 times, 1 to 8 times, 1 to 6 times, 1 to 4 times, 1 to 3 times (preferably morning, noon, evening), 5 seconds or more per time may be included in the mouth. It is possible.
In another embodiment, for example, 0.01 to 2 g of an oral composition (toothpaste) containing the dental plaque / stain inhibitor of the present invention is used at a time, and 1 to 1 per day. It is possible to brush 10 times, 1 to 8 times, 1 to 6 times, 1 to 4 times, 1 to 3 times (preferably morning, noon, and evening).
The target of the dental plaque / stain prevention method is not particularly limited, but is targeted at mammals including humans. When the mammal including the human is wearing a removable denture or dental material, the removed denture or dental material can also be targeted.
For example, dentures or dental materials are added to a solution of the dental plaque / stain inhibitor of the present invention in water, ethanol, etc. 1 to 10 times, 1 to 8 times, 1 to 6 times, 1 to 4 times a day. It can be exemplified that the immersion is performed 1 to 3 times, each time for 30 seconds or more.
本発明は、重量平均分子量10,000〜5,000,000であり、
2−(メタ)アクリロイルオキシエチルホスホリルコリンに基づく構成単位(A)10〜90モル%と、
アルキル基含有(メタ)アクリル系単量体に基づく構成単位(B1)、4級アンモニウム基含有(メタ)アクリル系単量体に基づく構成単位(B2)および(メタ)アクリルアミド系単量体に基づく構成単位(B3)からなる群から選ばれる少なくとも1種の構成単位90〜10モル%と
を含有するデンタルプラーク・ステイン付着防止用共重合体も対象とする。
2- (Meta) acryloyloxyethyl phosphorylcholine-based structural unit (A) 10-90 mol%,
Constituent unit based on alkyl group-containing (meth) acrylic monomer (B1), based on quaternary ammonium group-containing (meth) acrylic monomer-based structural unit (B2) and (meth) acrylamide-based monomer Also included are dental plaque-stain adhesion-preventing copolymers containing 90-10 mol% of at least one constituent unit selected from the group consisting of the constituent units (B3).
本発明は、重量平均分子量10,000〜5,000,000であり、
2−(メタ)アクリロイルオキシエチルホスホリルコリンに基づく構成単位(A)10〜90モル%と、
アルキル基含有(メタ)アクリル系単量体に基づく構成単位(B1)、4級アンモニウム基含有(メタ)アクリル系単量体に基づく構成単位(B2)および(メタ)アクリルアミド系単量体に基づく構成単位(B3)からなる群から選ばれる少なくとも1種の構成単位90〜10モル%と
を含有する共重合体をデンタルプラーク・ステイン付着防止剤の製造としての使用も対象とする。
2- (Meta) acryloyloxyethyl phosphorylcholine-based structural unit (A) 10-90 mol%,
Constituent unit based on alkyl group-containing (meth) acrylic monomer (B1), based on quaternary ammonium group-containing (meth) acrylic monomer-based structural unit (B2) and (meth) acrylamide-based monomer The use of a copolymer containing 90 to 10 mol% of at least one structural unit selected from the group consisting of the structural unit (B3) for the production of a dental plaque stain inhibitor is also targeted.
以下、本発明について実施例および比較例により、本発明のデンタルプラーク・ステイン付着防止剤、該防止剤を含む口腔用組成物およびデンタルプラーク・ステイン付着防止方法の効果を具体的に説明する。なお、本実施例および比較例に用いた共重合および重合体は、次の通りである。
MPCポリマー(1): 2−メタクリロイルオキシエチルホスホリルコリン・ブチルメタクリレート共重合体〔共重合組成比(モル比)80/20、重量平均分子量:600,000〕であり、特開平11−035605の実施例記載の方法によって重合を行って得られた。
MPCポリマー(2): 2−メタクリロイルオキシエチルホスホリルコリン・ブチルメタクリレート共重合体〔共重合組成比(モル比)30/70、重量平均分子量:142,000〕であり、特開2004−196868の実施例記載の方法によって重合を行って得られた。
MPCポリマー(3): 2−メタクリロイルオキシエチルホスホリルコリン・ステアリルメタクリレート共重合体〔共重合組成(モル比)33/67、重量平均分子量:164,000〕であり、特開2004−196868の実施例記載の方法によって重合を行って得られた。
MPCポリマー(4): 2−メタクリロイルオキシエチルホスホリルコリン・2−ヒドロキシ−3−メタクリロイルオキシプロピルトリメチルアンモニウムクロライド共重合体〔共重合組成(モル比)70/30、重量平均分子量:450,000〕であり、特開2004−189678の実施例記載の方法によって重合を行って得られた。
MPCポリマー(5): 2−メタクリロイルオキシエチルホスホリルコリン・N,N−ジメチルアミノプロピルアクリルアミド・ステアリルメタクリレート共重合体〔共重合組成(モル比)90/2/8、重量平均分子量:820,000〕であり、特開2013−018749の実施例記載の方法によって重合を行って得られた。
ホモポリマー(A): 2−メタクリロイルオキシエチルホスホリルコリンの重合体〔重量平均分子量:200,000〕であり、特開平8−333421の実施例記載の方法によって重合を行って得られた。
ホモポリマー(B1):ブチルメタクリレートの重合体〔重量平均分子量:180,000〕であり、和光純薬工業(株)(製品名:ポリ(メタクリル酸n−ブチル))より購入して試験に用いた。
ホモポリマー(B2): 2−ヒドロキシ−3−メタクリロイルオキシプロピルトリメチルアンモニウムクロライドの重合体〔重量平均分子量:300,000〕であり、特開平8−258403の実施例記載の方法によって重合を行って得られた。
ホモポリマー: N,N−ジメチルアクリルアミドの重合体〔数平均分子量:10,000〕であり、シグマアルドリッチジャパン(製品名:Poly(N,N−dimethylacrylamide)、DDMAT terminated)より購入して試験に用いた。Hereinafter, the effects of the dental plaque / stain adhesion inhibitor, the oral composition containing the inhibitor, and the dental plaque / stain adhesion prevention method of the present invention will be specifically described with reference to Examples and Comparative Examples of the present invention. The copolymers and polymers used in this example and comparative examples are as follows.
MPC polymer (1): 2-methacryloyloxyethyl phosphorylcholine / butyl methacrylate copolymer [copolymerization composition ratio (molar ratio) 80/20, weight average molecular weight: 600,000], which is an example of JP-A-11-305605. It was obtained by carrying out polymerization by the method described.
MPC polymer (2): 2-methacryloyloxyethyl phosphorylcholine / butyl methacrylate copolymer [copolymerization composition ratio (molar ratio) 30/70, weight average molecular weight: 142,000], which is an example of JP-A-2004-196868. It was obtained by carrying out polymerization by the method described.
MPC polymer (3): 2-methacryloyloxyethyl phosphorylcholine / stearyl methacrylate copolymer [copolymerization composition (molar ratio) 33/67, weight average molecular weight: 164,000], which is described in Examples of JP-A-2004-196868. It was obtained by carrying out polymerization by the method of.
MPC polymer (4): 2-methacryloyloxyethyl phosphorylcholine 2-hydroxy-3-methacryloyloxypropyltrimethylammonium chloride copolymer [copolymerization composition (molar ratio) 70/30, weight average molecular weight: 450,000]. , JP-A-2004-189678, obtained by carrying out polymerization by the method described in Examples.
MPC polymer (5): 2-methacryloyloxyethyl phosphorylcholine N, N-dimethylaminopropylacrylamide / stearyl methacrylate copolymer [copolymerization composition (molar ratio) 90/2/8, weight average molecular weight: 820,000] Yes, it was obtained by carrying out polymerization by the method described in Examples of JP2013-018549.
Homopolymer (A): A polymer of 2-methacryloyloxyethyl phosphorylcholine [weight average molecular weight: 200,000], which was obtained by polymerization according to the method described in Examples of JP-A-8-333421.
Homopolymer (B1): A polymer of butyl methacrylate [weight average molecular weight: 180,000], purchased from Wako Pure Chemical Industries, Ltd. (product name: poly (n-butyl methacrylate)) for testing. There was.
Homopolymer (B2): A polymer of 2-hydroxy-3-methacryloyloxypropyltrimethylammonium chloride [weight average molecular weight: 300,000], obtained by polymerizing by the method described in Examples of JP-A-8-258403. Was done.
Homopolymer: A polymer of N, N-dimethylacrylamide [number average molecular weight: 10,000], purchased from Sigma-Aldrich Japan (product name: Poly (N, N-dimerylacrylamide), DDMATterminated) for testing. There was.
[実施例1]
精製水約80gにMPCポリマー(1)0.001gを加え、攪拌した。この後、これに全量100mLとなるように精製水を加えて本発明の口腔用組成物を製造した。
[実施例2〜実施例11]
表1に示す種類および量の成分を使用した以外は、実施例1と同様の手順に従って本発明の口腔用組成物を製造した。
[比較例1〜比較例9および対照]
表2に示す種類および量の成分を使用した以外は、実施例1と同様の手順に従って本発明の口腔用組成物とは異なる口腔用組成物を製造した。[Example 1]
0.001 g of MPC polymer (1) was added to about 80 g of purified water, and the mixture was stirred. Then, purified water was added to the total volume to 100 mL to produce the oral composition of the present invention.
[Examples 2 to 11]
The oral composition of the present invention was produced according to the same procedure as in Example 1 except that the components of the types and amounts shown in Table 1 were used.
[Comparative Examples 1 to 9 and Control]
An oral composition different from the oral composition of the present invention was produced according to the same procedure as in Example 1 except that the components of the types and amounts shown in Table 2 were used.
<タンパク汚れ付着抑制評価>
歯面に付着するデンタルプラークをタンパク汚れと定義して、以下の手順に従ってタンパク汚れ付着抑制評価を行った。
(1)ハイドロキシアパタイト粉50mgと精製水5mLとを混合し、懸濁液を調製した。
(2)この懸濁液75μLを取り出し、エッペンドルフチューブへ入れ、遠心分離操作(3000rpm、5分間)により上澄みを取り除いた。
(3)実施例1を1mL加え、2分間攪拌した。
(4)遠心分離操作(3000rpm、5分間)により上澄みを取り除き、精製水1mLを加え混合した(この操作を「洗浄操作」という)。
(5)再度、洗浄操作を行った。
(6)遠心分離操作(3000rpm、5分間)により上澄みを取り除き、アルブミン溶液(アルブミン濃度:3mg/mL)75μLを加え、90分間静置した。
(7)洗浄操作を2回繰返し、1N塩酸100μLおよび0.1mol/Lリン酸緩衝液、pH8.0 1mLを加えて攪拌した後、この液400μLを取り出しフルオレスカミンのアセトン溶液(フルオレスカミン濃度:0.3mg/mL)150μLと混合した。
(8)(7)の液を96ウェルプレートへ200μL入れ、プレートリーダー(Spectra Max M3、Molecular Devices社製)を用いて蛍光強度(励起波長:360nm、蛍光波長:460nm)を測定し、下記の式(1)を用いてタンパク汚れ付着抑制率(%)を算出した。
なお、タンパク汚れ付着抑制評価実施に際して、実施例1の代わりに精製水を用いた条件で試験を行い、これを対照とした。<Evaluation of protein stain adhesion suppression>
Dental plaque adhering to the tooth surface was defined as protein stain, and protein stain adhesion suppression evaluation was performed according to the following procedure.
(1) 50 mg of hydroxyapatite powder and 5 mL of purified water were mixed to prepare a suspension.
(2) 75 μL of this suspension was taken out, placed in an Eppendorf tube, and the supernatant was removed by centrifugation (3000 rpm, 5 minutes).
(3) 1 mL of Example 1 was added, and the mixture was stirred for 2 minutes.
(4) The supernatant was removed by a centrifugation operation (3000 rpm, 5 minutes), 1 mL of purified water was added and mixed (this operation is referred to as a "washing operation").
(5) The cleaning operation was performed again.
(6) The supernatant was removed by centrifugation (3000 rpm, 5 minutes), 75 μL of an albumin solution (albumin concentration: 3 mg / mL) was added, and the mixture was allowed to stand for 90 minutes.
(7) The washing operation was repeated twice, 100 μL of 1N hydrochloric acid, 0.1 mol / L phosphate buffer, and 1 mL of pH 8.0 were added and stirred, and then 400 μL of this solution was taken out and an acetone solution of fluorescamine (fluorescamine) was taken out. Concentration: 0.3 mg / mL) was mixed with 150 μL.
(8) Add 200 μL of the solution of (7) to a 96-well plate, measure the fluorescence intensity (excitation wavelength: 360 nm, fluorescence wavelength: 460 nm) using a plate reader (Spectra Max M3, manufactured by Molecular Devices), and measure the following. The protein stain adhesion suppression rate (%) was calculated using the formula (1).
In addition, in carrying out the evaluation of protein stain adhesion suppression, a test was conducted under the condition that purified water was used instead of Example 1, and this was used as a control.
{タンパク汚れ付着抑制率(%)}={(対照の蛍光強度)−(実施例1の蛍光強度)}/(対照の蛍光強度)×100・・・式(1) {Protein stain adhesion suppression rate (%)} = {(Control fluorescence intensity)-(Fluorescence intensity of Example 1)} / (Control fluorescence intensity) x 100 ... Equation (1)
実施例2〜実施例11、比較例1〜比較例9および対照についても手順(1)〜(8)によりタンパク汚れ付着抑制率を算出した。タンパク汚れ付着抑制率を表1および表2に示す。 For Examples 2 to 11, Comparative Examples 1 to 9 and the control, the protein stain adhesion suppression rate was calculated by the procedures (1) to (8). The protein stain adhesion suppression rate is shown in Tables 1 and 2.
<コーヒー汚れ付着抑制評価>
歯面に付着するステインを、コーヒー由来のもののみであると定義して、以下の手順に従ってコーヒー汚れ付着抑制評価を行った。
(1)遠心管へハイドロキシアパタイト粉40mgを量り、実施例1を1mL加えて10分間静置した。
(2)さらにコーヒーを1mL加えて10分間静置した。
(3)この後、上澄み液をろ過して取り出し、紫外可視吸光光度計(V−560、日本分光(株)製)を用いて550nmにおける透過率(%T)を測定し、下記の式(2)を用いてコーヒー汚れ付着抑制率(%)を算出した。
なお、コーヒー汚れ付着抑制評価の実施に際して、実施例1の代わりに精製水を用いた条件で試験を行い、これを対照とした。<Evaluation of coffee stain suppression>
The stain adhering to the tooth surface was defined as only coffee-derived stain, and coffee stain adhesion suppression evaluation was performed according to the following procedure.
(1) 40 mg of hydroxyapatite powder was weighed into a centrifuge tube, 1 mL of Example 1 was added, and the mixture was allowed to stand for 10 minutes.
(2) Further, 1 mL of coffee was added and allowed to stand for 10 minutes.
(3) After that, the supernatant is filtered and taken out, and the transmittance (% T) at 550 nm is measured using an ultraviolet-visible spectrophotometer (V-560, manufactured by JASCO Corporation), and the following formula ( The coffee stain adhesion suppression rate (%) was calculated using 2).
In carrying out the coffee stain adhesion suppression evaluation, a test was conducted under the condition that purified water was used instead of Example 1, and this was used as a control.
{コーヒー汚れ付着抑制率(%)}={(実施例1の透過率)−(対照の透過率)}/{(コーヒー1/2希釈液の透過率)−(対照の透過率)}×100・・・式(2) {Coffee stain adhesion suppression rate (%)} = {(Transmittance of Example 1)-(Control transmittance)} / {(Transmittance of coffee 1/2 diluent)-(Control transmittance)} × 100 ... Equation (2)
実施例2〜実施例11、比較例1〜比較例9および対照についても手順(1)〜(3)によりコーヒー汚れ付着抑制率を算出した。コーヒー汚れ付着抑制率を表1および表2に示す。 For Examples 2 to 11, Comparative Examples 1 to 9 and the control, the coffee stain adhesion suppression rate was calculated by the procedures (1) to (3). Tables 1 and 2 show the coffee stain adhesion suppression rate.
実施例1ではタンパク汚れ付着抑制率は10.2%であった。MPCポリマー(1)の配合濃度が上昇するに従って、タンパク汚れ付着抑制率は向上し、実施例7において最も高いタンパク汚れ付着抑制率40.1%を示した。この効果はMPCポリマー(1)だけではなく、MPCポリマー(2)、MPCポリマー(3)、MPCポリマー(4)およびMPCポリマー(5)についてもタンパク汚れ付着抑制効果が見られ、その抑制率は27.3〜28.1%であった。一方、比較例のタンパク汚れ付着抑制率は2.4〜5.8%と著しく低い結果であった。また、比較例7および比較例9については、重合したポリマーが不溶のため試験実施不可能であった(*表中には「−」で記載)。 In Example 1, the protein stain adhesion suppression rate was 10.2%. As the blending concentration of the MPC polymer (1) increased, the protein stain adhesion suppression rate improved, showing the highest protein stain adhesion suppression rate of 40.1% in Example 7. This effect is seen not only in the MPC polymer (1) but also in the MPC polymer (2), the MPC polymer (3), the MPC polymer (4) and the MPC polymer (5), and the suppression rate is high. It was 27.3 to 28.1%. On the other hand, the protein stain adhesion suppression rate of the comparative example was as low as 2.4 to 5.8%. Further, in Comparative Example 7 and Comparative Example 9, the polymer was insoluble and the test could not be carried out (* indicated by "-" in the table).
コーヒー汚れ付着抑制率に関し、実施例1において20.9%であった。コーヒー汚れ付着抑制率についてもタンパク汚れ付着抑制率と同様、MPCポリマー(1)の配合濃度が上昇するに従って、コーヒー汚れ付着抑制率が向上し、実施例7において最も高い抑制率78.9%であった。コーヒー汚れ付着抑制効果についても、タンパク汚れ付着抑制効果と同様に、MPCポリマー(2)、MPCポリマー(3)、MPCポリマー(4)およびMPCポリマー(5)についても見られ、その抑制率は50.7〜53.7%であった。比較例のコーヒー汚れ付着抑制率は、5.3〜10.4%と著しく低い結果であった。コーヒー汚れ付着抑制率は、タンパク汚れ付着抑制率と同様に、比較例7および比較例9について、重合したポリマーが不溶のため試験実施不可能であった(*表中には「−」で記載)。 The coffee stain adhesion suppression rate was 20.9% in Example 1. As for the coffee stain adhesion suppression rate, as with the protein stain adhesion suppression rate, the coffee stain adhesion suppression rate improves as the blending concentration of the MPC polymer (1) increases, and the highest suppression rate of 78.9% in Example 7 is achieved. there were. As for the coffee stain adhesion suppressing effect, the MPC polymer (2), MPC polymer (3), MPC polymer (4) and MPC polymer (5) are also observed in the same manner as the protein stain adhesion suppressing effect, and the suppression rate is 50. It was .7 to 53.7%. The coffee stain adhesion suppression rate of the comparative example was as low as 5.3 to 10.4%. Similar to the protein stain adhesion suppression rate, the coffee stain adhesion suppression rate could not be tested in Comparative Example 7 and Comparative Example 9 because the polymerized polymer was insoluble (* indicated by "-" in the table. ).
[実施例12]
精製水約80gにMPCポリマー(1)0.001gを加え、攪拌した。この後、順次、サッカリンナトリウム0.006g、グリセリン3.0g、ミリスチン酸ポリグリセリル0.25g、ソルビトール液(70%)1.0g、エタノール4.0g、クエン酸0.01g、クエン酸三ナトリウム0.05g、パラオキシ安息香酸エチル0.05gおよび香料0.5gを加え攪拌し、全量100mLとなるように精製水を加えて本発明の口腔用組成物である液体ハミガキを製造した。
[実施例13〜実施例20]
表3に示す種類および量の成分を使用した以外は、実施例12と同様の手順に従って本発明の口腔用組成物である液体ハミガキを製造した。
[比較例10〜比較例18および対照]
表4に示す種類および量の成分を使用した以外は、実施例12と同様の手順に従って、本発明の口腔用組成物とは異なる口腔用組成物である液体ハミガキを製造した。[Example 12]
0.001 g of MPC polymer (1) was added to about 80 g of purified water, and the mixture was stirred. After this, 0.006 g of sodium saccharin, 3.0 g of glycerin, 0.25 g of polyglyceryl myristate, 1.0 g of sorbitol solution (70%), 4.0 g of ethanol, 0.01 g of citric acid, 0.05 g of trisodium citrate. , 0.05 g of ethyl paraoxybenzoate and 0.5 g of fragrance were added and stirred, and purified water was added so as to have a total volume of 100 mL to produce a liquid sardine, which is the oral composition of the present invention.
[Examples 13 to 20]
The liquid toothpaste, which is the oral composition of the present invention, was produced according to the same procedure as in Example 12 except that the components of the types and amounts shown in Table 3 were used.
[Comparative Examples 10 to 18 and Control]
A liquid toothpaste, which is an oral composition different from the oral composition of the present invention, was produced according to the same procedure as in Example 12 except that the components of the types and amounts shown in Table 4 were used.
<使用後の歯面の感触>
得られた液体口腔用組成物(液体ハミガキ)である実施例12について10mLで口腔内を20秒間含そうし、吐き出した直後の歯面を舌で触ったときの感触を下記基準に従って評価した。評価は専門パネラーが行い、その評価結果を表3および表4に示す。
A:歯面がなめらかな感触であり、清掃実効感が高い
B:歯面がややきしむが、清掃実効感はある
C:歯面がなめらかでなく、清掃実効感に乏しい
D:歯面がギシギシする
実施例13〜実施例20、比較例10〜比較例18および対照についても使用後の歯面の感触について評価を行い、その結果を表3および表4に示す。<Feeling of the tooth surface after use>
The obtained liquid oral composition (liquid toothpaste) of Example 12 was soaked in the oral cavity with 10 mL for 20 seconds, and the feel when the tooth surface immediately after exhalation was touched with the tongue was evaluated according to the following criteria. The evaluation is performed by a specialized panelist, and the evaluation results are shown in Tables 3 and 4.
A: The tooth surface feels smooth and the cleaning effect is high. B: The tooth surface is slightly squeaky, but the cleaning effect is good. C: The tooth surface is not smooth and the cleaning effect is poor. D: The tooth surface is squeaky. The feeling of the tooth surface after use was also evaluated for Examples 13 to 20, Comparative Examples 10 to 18, and Control, and the results are shown in Tables 3 and 4.
<タンパク汚れ付着抑制評価(口腔内)>
以下の手順に従ってタンパク汚れ付着抑制評価(口腔内)を行った。
(1)あらかじめデンタルプラークがゼロになるまで歯をブラッシングした。
(2)実施例12の液体ハミガキ10mLを用いて30秒間うがいをし、再度、2分間ブラッシングした。
(3)この後、ブラッシング、洗口液による洗浄を行わずに8時間生活をした。
(4)8時間後に歯に付着した歯垢量を測定した。実施例12の液体ハミガキの歯垢量は3名のパネラーの合計量とし、下記の式(3)を用いてタンパク汚れ付着抑制率(%)を算出した。
なお、デンタルプラークがゼロになるまでの歯のブラッシングを行うのみで、実施例12の液体ハミガキによるブラッシングを行っていない場合の歯垢量を対照とした。 <Evaluation of protein stain adhesion suppression (intraoral)>
The protein stain adhesion suppression evaluation (intraoral) was performed according to the following procedure.
(1) The teeth were brushed in advance until the dental plaque became zero.
(2) Gargle with 10 mL of the liquid toothpaste of Example 12 for 30 seconds, and brushed again for 2 minutes.
(3) After that, I lived for 8 hours without brushing and washing with mouthwash.
(4) The amount of plaque adhering to the teeth was measured after 8 hours. The amount of plaque in the liquid toothpaste of Example 12 was the total amount of the three panelists, and the protein stain adhesion suppression rate (%) was calculated using the following formula (3).
The amount of plaque when brushing the teeth until the dental plaque became zero and not brushing with the liquid toothpaste of Example 12 was used as a control.
{タンパク汚れ付着抑制率(%)}={(対照の歯垢量)−(実施例12の歯垢量)}/(対照の歯垢量)×100・・・式(3) {Protein stain adhesion suppression rate (%)} = {(Control plaque amount)-(Control plaque amount)} / (Control plaque amount) x 100 ... Equation (3)
実施例13〜実施例20、比較例10〜比較例18および対照についても手順(1)〜(4)によりタンパク汚れ付着抑制率を算出した。タンパク汚れ付着抑制率を表3および表4に示す。 For Examples 13 to 20, Comparative Examples 10 to 18, and Control, the protein stain adhesion suppression rate was calculated by the procedures (1) to (4). The protein stain adhesion suppression rates are shown in Tables 3 and 4.
実施例12ではタンパク汚れ付着抑制率は15.1%であり、MPCポリマー(1)の配合濃度が上昇するに従って、タンパク汚れ付着抑制率も向上する傾向を示し、実施例16で最も高い値33.5%となった。このタンパク汚れ付着抑制効果は、MPCポリマー(2)、MPCポリマー(3)、MPCポリマー(4)およびMPCポリマー(5)についても見られ、そのタンパク汚れ付着抑制率は20.0〜28.8%であった。一方、比較例のタンパク汚れ付着抑制率は3.8〜7.7%となった。比較例16および比較例18については、組成物に対して不溶であったため試験実施不可能であった(*表中には「−」で記載)。 In Example 12, the protein stain adhesion suppression rate was 15.1%, and as the blending concentration of the MPC polymer (1) increased, the protein stain adhesion suppression rate tended to increase, which was the highest value 33 in Example 16. It was 5.5%. This protein stain adhesion suppressing effect is also observed in MPC polymer (2), MPC polymer (3), MPC polymer (4) and MPC polymer (5), and the protein stain adhesion suppressing rate is 20.0 to 28.8. %Met. On the other hand, the protein stain adhesion suppression rate of the comparative example was 3.8 to 7.7%. In Comparative Examples 16 and 18, the test could not be carried out because they were insoluble in the composition (* indicated by "-" in the table).
使用後の歯面の感触に関し、実施例では全てA評価となったが、比較例での評価は、比較例10〜比較例15についてC評価であり、比較例17および対照についてはD評価であった。比較例16および比較例18については、組成物に対して不溶であったため試験実施不可能であった(*表中には「−」で記載)。 Regarding the feel of the tooth surface after use, all of the examples were evaluated as A, but the evaluations in Comparative Examples were C in Comparative Examples 10 to 15, and D in Comparative Examples 17 and Control. there were. In Comparative Examples 16 and 18, the test could not be carried out because they were insoluble in the composition (* indicated by "-" in the table).
[実施例21〜実施例25]
液体ハミガキ以外にも、表5に示す練り歯磨き剤を製造し、使用後の歯面の感触およびタンパク汚れ付着抑制率(%)に関する評価を実施した。
その結果、練り歯磨き剤については、液体ハミガキと同様に、使用後の歯面の感触は良好で全てA評価であった。さらに、タンパク汚れ付着抑制率も15.3〜15.5%と良好な結果を示した。[Examples 21 to 25]
In addition to the liquid dentifrice, the toothpaste shown in Table 5 was produced and evaluated for the feel of the tooth surface after use and the protein stain adhesion suppression rate (%).
As a result, with respect to the dentifrice, the feel of the tooth surface after use was good as in the case of liquid dentifrice, and all were evaluated as A. Furthermore, the protein stain adhesion suppression rate was also good, showing a good result of 15.3 to 15.5%.
以上より、本発明のデンタルプラーク・ステイン付着防止剤は食品等に由来する汚れ、色素の歯面への付着・沈着の防止効果を示した。また、これらの効果は液体ハミガキや練り歯磨き剤といった口腔用組成物とした際にも有効で、良好な使用感と歯垢形成抑制を示した。さらに、これらの結果から、本発明のデンタルプラーク・ステイン付着防止剤を使用したデンタルプラーク・ステイン付着防止方法についても、デンタルプラーク・ステインの付着・沈着の防止効果を有することを確認できた。本発明のデンタルプラーク・ステイン付着防止剤、これを含有する口腔用組成物およびデンタルプラーク・ステイン付着防止方法の優れた効果は、本発明に用いる共重合体分子が歯面自体やペリクルへと吸着することで、細菌の生産する成分や、色素の吸着を阻害することで発現されるものと推測される。 From the above, the dental plaque / stain adhesion inhibitor of the present invention has shown the effect of preventing the adhesion / deposition of stains and pigments derived from foods and the like on the tooth surface. In addition, these effects were also effective when used as an oral composition such as a liquid toothpaste or a toothpaste, and showed a good feeling of use and suppression of plaque formation. Furthermore, from these results, it was confirmed that the method for preventing the adhesion of dental plaque / stain using the dental plaque / stain adhesion inhibitor of the present invention also has the effect of preventing the adhesion / deposition of dental plaque / stain. The excellent effect of the dental plaque / stain adhesion inhibitor of the present invention, the oral composition containing the same, and the dental plaque / stain adhesion prevention method is that the copolymer molecule used in the present invention is adsorbed on the tooth surface itself or the pellicle. By doing so, it is presumed that it is expressed by inhibiting the adsorption of components produced by bacteria and pigments.
デンタルプラーク・ステインの付着・沈着を防止または抑制できるデンタルプラーク・ステイン付着防止剤、これを含有する口腔用組成物およびデンタルプラーク・ステイン付着防止方法を提供することができる。 It is possible to provide a dental plaque / stain adhesion inhibitor capable of preventing or suppressing the adhesion / deposition of dental plaque / stain, an oral composition containing the same, and a dental plaque / stain adhesion prevention method.
Claims (5)
2−(メタ)アクリロイルオキシエチルホスホリルコリンに基づく構成単位(A)10〜90モル%と、
アルキル基含有(メタ)アクリル系単量体に基づく構成単位(B1)、4級アンモニウム基含有(メタ)アクリル系単量体に基づく構成単位(B2)および(メタ)アクリルアミド系単量体に基づく構成単位(B3)からなる群から選ばれる少なくとも1種の構成単位90〜10モル%と
からなる共重合体を含有するステイン付着防止剤であって、ここで、該共重合体は、以下のいずれか1から選択されることを特徴とする、ステイン付着防止剤。
(1)2−(メタ)アクリロイルオキシエチルホスホリルコリンに基づく構成単位(A)と4級アンモニウム基含有(メタ)アクリル系単量体に基づく構成単位(B2)からなる共重合体
(2)2−(メタ)アクリロイルオキシエチルホスホリルコリンに基づく構成単位(A)とアルキル基含有(メタ)アクリル系単量体に基づく構成単位(B1)と(メタ)アクリルアミド系単量体に基づく構成単位(B3)からなる共重合体
The weight average molecular weight is 10,000 to 5,000,000.
2- (Meta) acryloyloxyethyl phosphorylcholine-based structural unit (A) 10-90 mol%,
Constituent unit based on alkyl group-containing (meth) acrylic monomer (B1), based on quaternary ammonium group-containing (meth) acrylic monomer (B2) and (meth) acrylamide-based monomer With at least one constituent unit 90-10 mol% selected from the group consisting of the constituent units (B3)
An anti-staining agent containing a copolymer composed of the above, wherein the copolymer is selected from any one of the following.
(1) A copolymer composed of a structural unit (A) based on 2- (meth) acryloyloxyethyl phosphorylcholine and a structural unit (B2) based on a quaternary ammonium group-containing (meth) acrylic monomer.
(2) 2- (Meta) acryloyloxyethyl phosphorylcholine-based structural unit (A) and alkyl group-containing (meth) acrylic monomer-based structural unit (B1) and (meth) acrylamide-based monomer-based configuration Copolymer consisting of unit (B3)
Claim 1 in which the structural unit (A) is a structural unit based on 2- (meth) acryloyloxyethyl phosphorylcholine, and the structural unit (B2) is a structural unit based on 2-hydroxy-3-methacryloyloxypropyltrimethylammonium chloride. Stain adhesion inhibitor according to .
The structural unit (A) is a structural unit based on 2- (meth) acryloyloxyethyl phosphorylcholine, the structural unit (B1) is a structural unit based on stearyl methacrylate, and the structural unit (B3) is N, N-dimethylaminopropyl. The stain adhesion inhibitor according to claim 1, which is a structural unit based on acrylamide.
An oral composition containing 0.001 to 5.0 w / v% of the stain adhesion inhibitor according to any one of claims 1 to 3 and 3.0 to 99.9 w / v% of water.
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Free format text: JAPANESE INTERMEDIATE CODE: R250 |