CN1196232A - 假牙粘合剂 - Google Patents
假牙粘合剂 Download PDFInfo
- Publication number
- CN1196232A CN1196232A CN98107052A CN98107052A CN1196232A CN 1196232 A CN1196232 A CN 1196232A CN 98107052 A CN98107052 A CN 98107052A CN 98107052 A CN98107052 A CN 98107052A CN 1196232 A CN1196232 A CN 1196232A
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- Prior art keywords
- copolymer
- monomer
- weight
- binding agent
- acid
- Prior art date
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- 229920001577 copolymer Polymers 0.000 claims abstract description 47
- 239000000178 monomer Substances 0.000 claims abstract description 29
- 230000001070 adhesive effect Effects 0.000 claims abstract description 24
- 239000000853 adhesive Substances 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 11
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- -1 alkyl vinyl ether Chemical compound 0.000 claims description 22
- 239000011230 binding agent Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 17
- 229920000642 polymer Polymers 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000011734 sodium Substances 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 230000007935 neutral effect Effects 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- 239000011575 calcium Substances 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011701 zinc Substances 0.000 claims description 5
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
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- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
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- LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical compound C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-N 0.000 claims description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 238000010526 radical polymerization reaction Methods 0.000 claims description 2
- 239000011833 salt mixture Substances 0.000 claims description 2
- 229910052712 strontium Inorganic materials 0.000 claims description 2
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 claims 1
- 229920002126 Acrylic acid copolymer Polymers 0.000 claims 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 229940072056 alginate Drugs 0.000 claims 1
- 235000010443 alginic acid Nutrition 0.000 claims 1
- 229920000615 alginic acid Polymers 0.000 claims 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 229920003145 methacrylic acid copolymer Polymers 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000003999 initiator Substances 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- 239000003981 vehicle Substances 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 8
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 8
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 8
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 7
- 238000007720 emulsion polymerization reaction Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 150000003863 ammonium salts Chemical class 0.000 description 6
- 229940099259 vaseline Drugs 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
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- 238000005516 engineering process Methods 0.000 description 5
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- 238000006386 neutralization reaction Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 4
- 235000010265 sodium sulphite Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000000084 colloidal system Substances 0.000 description 3
- 238000007046 ethoxylation reaction Methods 0.000 description 3
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- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 3
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- 150000003751 zinc Chemical class 0.000 description 3
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 229920003134 Eudragit® polymer Polymers 0.000 description 2
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- HKFCGZHDMPKLBR-UHFFFAOYSA-N N(=O)OCCCCCCCC.S(=O)(=O)(O)C(C(=O)O)O Chemical compound N(=O)OCCCCCCCC.S(=O)(=O)(O)C(C(=O)O)O HKFCGZHDMPKLBR-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
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- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
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- 235000010323 ascorbic acid Nutrition 0.000 description 2
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- 150000004676 glycans Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- SBGKURINHGJRFN-UHFFFAOYSA-N hydroxymethanesulfinic acid Chemical compound OCS(O)=O SBGKURINHGJRFN-UHFFFAOYSA-N 0.000 description 2
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- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 2
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- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- KWVPFECTOKLOBL-KTKRTIGZSA-N 2-[(z)-octadec-9-enoxy]ethanol Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCO KWVPFECTOKLOBL-KTKRTIGZSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- KBIWNQVZKHSHTI-UHFFFAOYSA-N 4-n,4-n-dimethylbenzene-1,4-diamine;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)C1=CC=C(N)C=C1 KBIWNQVZKHSHTI-UHFFFAOYSA-N 0.000 description 1
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- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
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- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
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Abstract
假牙用的粘合剂,它包含:a)作为活性粘合成分的部分或全部中和共聚物,此共聚物含有占其5—95%重量的通式Ⅰ的一种或多种丙烯酸酯:CH2=CR’-COOR Ⅰ(单体A),式中R’是氢或甲基,R是含1—30个碳原子的烷基,及含占其95—5%重量的甲基丙烯酸和/或丙烯酸(单体B),以及b)假牙粘合剂中常用的媒介物。
Description
本发明涉及假牙用粘合剂,它包含作为活性粘合剂组份的至少部分中和的丙烯酸酯或甲基丙烯酸酯与丙烯酸或甲基丙烯酸的共聚物,以及通常的媒介物。
假牙用粘合剂被用于使假牙配装于或至少帮助配装于软腭组织的粘膜和齿龈槽,形成紧密强固的固定。把粘合剂涂到湿的假牙上,然后把它插入嘴中。唾液使粘合剂层的表面变湿,使它膨胀,而同时增大粘合力。
其基本参数是粘合力和粘合的持久性。在这里关于固定效应的机理是很复杂的,因此,媒介物基剂及制成品的粘度起着重要作用。用作媒介物基物的物质包括矿物油(石蜡油),凡士林(矿脂)及蜡。需要时时用聚乙二醇或甘油将它稀释,而且使它们占制成品的约20-60%。其粘度首先由全部配方来测定;即,在粘合剂中的活性物质和媒介物质的总量。存在大量的不同组合物,每种适应于各种特殊用途。
从众多专利例如EP-A0122481和0265916所知的假牙粘合剂均显示很好的粘合力,它们的活性粘合组合物含有乙烯基甲醚与马来酸的共聚物,此共聚物已被部分中和或全部中和。在说明书中合适的盐是碱金属盐,碱土金属盐或锌盐。
然而制备这些共聚物通常需要有机溶剂,而此有机溶剂又必须以巨大技术花费再除去。不算这一花费,在很多情况下把溶剂除去并不是定量的,因而在一些情况下最终产品中仍含有残余溶剂。这是不希望的。
此外,US-A4542168公开了交联的和部分中和的聚丙烯酸与至少一种亲水聚合物一起用作活性粘合物质。这些假牙用粘合剂的缺点是其粘合力仍不够满意,而且它们同样要在溶剂中制备,而在产品中仍可检测到溶剂。
本发明的目的是提供一种假牙粘合剂,在其中活性物质包含共聚物,而这些共聚物进一步增大粘合剂的粘合力,而且这些共聚物能优选地不用溶剂而制备。
我们已发现,这一目的已用假牙粘合剂达到了,这类粘合剂包含:
a)作为活性粘合作用成分的部份或全部中和共聚物,此共聚物含有占其5-95%重量的通式I的一种或多种丙烯酸酯:
CH2=CR’-COOR I(单体A),式中R’是氢或甲基,R是含1-30个优选1-4个碳原子的烷基,及含占其95-5%重量的甲基丙烯酸和域丙烯酸(单体B),以及
b)假牙粘合剂中常用的媒介物。
优选的活化粘合作用的成份(a)是含20-80%重量丙烯酸乙酯和甲基丙烯酸甲酯,及含80-20%重量甲基丙烯酸或丙烯酸的那些组合物。可提到的具体例子是含约50%重量丙烯酸乙酯和约50%重量丙烯酸的共聚物例如EudragitL(ROhm)或KollicoatMAE30(BASF),或者含约67%重量甲基丙烯酸甲酯及约33%重量甲基丙烯酸的共聚物例如Eudragit((ROHM)。
此共聚物(a)也可含少量(例如最多为共聚物的30%重量)的另一种处于共聚态的单体(C),例如丙烯酰胺,甲基丙烯酰胺,N-乙烯基内酰胺,丙烯酸羟烷基酯,巴豆酸或马来酸。
此共聚物(a)必须至少被部分中和。通常,此共聚物游离羧基的30-95摩尔%,优选30-80摩尔%,特别优选35-75摩尔%已被中和成为碱金属,碱土金属或锌盐。此盐可以是单一盐或混合盐。优选的是钠、钙、锶或锌盐。
此共聚物的分子量通常为30,000-5,000,000,优选为100,000-3,000,000道尔顿,因此,在处于至少被部分中和的盐的状态时,它们在水中是溶解的或至少可溶胀的。通过制备方法和对盐的优化选择,可以控制它们的适用性能,特别是粘度二价盐的比例越高则通常导致增大溶液粘度。
此共聚物以溶液聚合法,或优选以在水中的悬浮聚合法或乳液聚合法这些公知方法来制取。特别优选的是乳液聚合法。
在下面更详细描述的乳液聚合法中,离子的和域非离子乳化剂和/或保护胶体及稳定剂被用作表面活性化合物。
对合适保护胶体的详细描述见Houben-weyl,Methoden der organischenChemie,Volume XIV/1,Makromolekulare Stoffe,Georg ThiemeVerlag,Stuttgart,1961,pp.411-420。合适的乳化剂包括阴离子的、阳离子的或非离子的乳化剂。可采用的伴随表面活性物质优选是排他的乳化剂,它们的分子量-与保护胶体截然不同-通常低于2000克/摩尔。当使用表面活性物质的混合物时,单一组分当然必须彼此相配伍,在拿不准时它可以在少量的初步实验的基础上进行选择。优选使用阴离子和非离子乳化剂作为表面活性物质。常用辅助乳化剂的例子是乙氧基化脂肪醇(EO单元:3-50,烷基:C8-C36),乙氧基化单-、双-和三烷基苯酚(EO单元:3-50,烷基:C4-C9),乙氧基化脱水山梨糖醇酯(EO单元:5-30;饱和及不饱和C12-C30脂肪酸),乙氧基化蓖麻油(EO单元:5-80,氢化的和未氢化的),磺基琥珀酸二烷基酯的碱金属盐,及硫酸烷基酯的碱金属盐和铵盐(烷基:C8-C12),乙氧基化烷醇的碱金属盐和铵盐(EO单元:4-30,烷基:C12-C18),乙氧基化烷基苯酚的碱金属盐和铵盐(EO单元:3-50,烷基:C4-C9),烷基磺酸的碱金属盐和铵盐(烷基:C12-C18),以及烷基芳基磺酸的碱金属盐和铵盐(烷基:C9-C18)。
其他合适乳化剂是通式II的化合物:式中R1和R2是氢或C4-C14烷基,但不能同时是氢,X和Y可以是碱金属离子和/或铵离子。优选的是,R1和R2是氢或含6-18个碳原子的直链的或支化的烷基,特别是含6、12或16个碳子的,而且不能同时是氢。X和Y优选是钠、钾或铵离子,特别优选钠。特别好的化合物II是其中X和Y是钠,R1是含12个碳原子的支链烷基,R2是氢或R1的那些化合物。通常用的技术级混合物含50-90%重量单烷基化产物,其例子是Dowfax2Al(Dow Chemical Company的商品名)。
适用的乳化剂也刊在Houben-Weyl所著PP192-208之中。
乳化剂的商业名称是例如Dowfax2A1,EmulanNP50,DextrolOC50,Emulgator 825,Emulgator 825 S,EmulanNP OG,TexaponNSO,Nekanil904S,LumitenI-RA,Lumiten3065,DiponilFES 77,LutensolAT18,SteinapolVSL,EmulphorNPS 25,CremophorRH 40,Tween80。
表面活性物的用量以被聚合的单体计,通常为0.1-10%重量。
乳液聚合水溶引发剂的例子是过二硫酸的铵盐或碱金属盐(例如过二硫酸钠),过氧化氢或有机过氧化物(如叔丁基过氧化氢)。
那些称作氧化还原(redox)引发剂体系的特别适用。
氧化还原体系由至少一种还原剂(通常是有机的)和一种无机的或有机的氧化剂组成。
氧原剂组分包括例如上述的乳液聚合引发剂。
还原剂组分包括例如亚硫酸的碱金属盐(如亚硫酸钠,亚硫酸氨钠),酸式亚硫酸碱金属盐(如亚硫酸氢钠,脂肪醛或酮的亚硫酸氢盐加成物(如丙酮亚硫酸氢盐),或者还原剂(如羟甲基亚磺酸及其盐,或抗坏血酸)。氧化还原引发引体系可以与可溶金属化合物合用,此金属组份可以以多个价态存在。
常用的氧化还原引发剂休系的例子是抗坏血酸/硫酸亚铁/过二硫酸钠,叔丁基过氧化氢/亚硫酸氢钠,叔丁基过氧化氢/羟甲基亚磺酸钠。个别组份例如还原组份也可以是混合物,例如羟甲基亚磺酸的钠盐和亚硫酸氢钠的混合物。
上述化合物通常以其水溶液形式使用,浓度下限以分散液可接受的水量来决定,而上限则由该化合物在水中的溶解度来决定。通常,此浓度以溶液计为0.1-30%重量,优选为0.5-20%重量特别优选为0.1-10%重量。
引发剂的数量以被聚合的单体计通常为0.1-10%重量,优选为0.5-5%重量。在乳液聚合反应中也可以使两种或多种不同的引发剂。
在聚合过程中可以使用调节剂,其数量例如以100重量份被聚合单体计为0-0.8重量份;这些调节剂降低摩尔量。合适调节剂的例子是具有硫羟基的化合物如叔丁基硫醇,硫代甘醇酸乙基己酯,巯基乙醇,巯丙基三甲氧基硅烷,或叔十二烷基硫醇。调节剂不含任何可聚合烯属不饱和基因。它们造成聚合物链的末端的增长,并因此连到聚合物链的端部。
乳液聚合通常在30-130℃,优选50-90℃下进行。聚合介质可以或者单由水组成,或者由水及与水相混液体(例如甲醇)的混合物组成。优选单独使用水。乳液聚合或者以间歇法进行,或者以进料技术的形式进行(它包括分步法及梯度法)。优选采用进料技术的方式,在其中将部分聚合反应混合物送入反应器中,把这起始部分加热到聚合温度聚合反应开始。然后在多个层上或在浓度梯度下往聚合反应区连续送入剩余的聚合反应混合物,送入时通常采用两个或多个在空间上分开的进料流,进料流中的一个或多个含有纯的单体或乳化状单体,而在进料期间维持着聚合反应。也可以往聚合反应中首先送入晶体聚合物,这是为了例如更好地达到粒径。
在游离基含水乳液聚合反应过程中加入引发剂的方法对所属领域技术熟练人员来说是公知的。它既可以全部加到初始的物料加往聚合反应器中,也可以在游离基聚合过程中连续地使用或分阶段加入,加入速度等于消耗速度。在每种单独情况下,其加入速度,如在该技术领域技术熟练人员所公知的,取决于引发剂体系的化学性质和聚合温度。优选的是在开始加入的物料中加一部分,而余下的部分则加至聚合反应区中,加入速度等于消耗速度。
为了除去残留单体,在真正乳液聚合反应终点之后换句话说在单体已至少95%转化之后加入引发剂也是有用的。
在采用进料技术的情况下,可以通过侧部从上面送入单一组份,或通过反应器层从下部送单一部分。
乳液聚合反应生成聚合物的含水溶液或分散液,其固含量通常为15-75%重量,优选25-60%重量。
然后将所能共聚物全部或部分转化为盐的形式。
这是在聚合反应之后或甚至在聚合过程中通过加入碱性无机盐例如碱金属或碱土金属或锌的氢氧化物,氧化物,磷酸物,碳酸盐,碳酸氢盐,醋酸盐或甲酸盐而做到的。
中和的方法,即把含羧基聚合物转变为其盐的方法是已知的,并在例如US-A5037924实施例了作3描述。一种技术上优越的方法在EP-A0315015中作了描述,此内容在这里被收作参考。
根据优选制法,首先加入聚合物水溶液或分散液,再按所需量和组成一份份地加入粉末状无机盐。如果需要,在随后的干燥操作之前,加入其他添加剂。然后从原理上说,也可以干燥末中和的共聚物,然后加入无机盐。
根据丙烯酸和/或甲基丙烯酸的比例,换句话说根据共聚物中羧基的数目,又根据中和度,获得了聚合物分散液或聚合物水溶液,为制得粘合剂,将此分散液或溶液进行干燥,因而能与媒介物(b)制成最终产品。
干燥采用公知的方法例如用流化床干燥器,或优选采用喷雾干燥法。
发现如DE-A2133709所述,在此干燥过程中调整干燥产品的水份,以使残留水份最高至10%重量,是明智的。也已发现,将干燥共聚物维持在一定粒径上,是明智的,例如小于250μ,优选为5至约200μ;换句话说,过筛和研磨会是必要的。
按通常方式在低于50℃下用机械混合法把此共聚物(a)与媒介物(b)进行混合。在混合期间可以也加入不削弱组合物粘合力的添加剂,例如香料,增稠剂(如二氧化硅粉末),或着色剂。
此媒介物(b)包含通常作为主要成份的矿物油例如液体石蜡,或凡士林和矿脂,含或不含粘度调节剂如聚乙二酸或甘油或低分子量聚乙烯。具有所需粘度的矿物油优选是高度提纯的在38℃时粘度为50-350mpas的白油。低分子量聚乙烯的分子量是例如1000-21000,优选为2000-5000(如凝胶渗透色谱法所测得)。平均分子量为约2000的粉状聚乙烯聚合物是特别优选的。在最终粘合剂组合物中媒介物(b)的比例通常为0.1-60%重量。
从原理上说,如果例如意图是制备粘合剂粉末,则在假牙粘合剂中没有油也可做到。
在干燥之前或之后,往此共聚物(a)或往(a)和媒介物(b)所制成混合物中也可加入别的活性粘合物,或改进假牙粘合剂其他性能的添加剂,例如烷基乙烯基醚马来酸酐共聚物部分盐,羧甲基纤维素钠,聚环氧乙烷,刺梧桐树脂,聚乙二醇,藻酸钠,羟乙基纤维素,聚壳糖,瓜耳胶,Caropol聚合物,聚乙烯醇,聚乙烯吡咯烷酮,乙烯吡咯烷酮与醋酸乙烯酯的共聚物,多糖或化学改性多糖,或者其他的对粘合起活性作用的技术熟练工人公知物质。
如EP-A0073850所述的,此新假牙粘合剂可再涂,以增大粘合持久性,同时阻滞了粘合活化组分的释放。
此新颖假牙粘合剂因其改进的粘合力,很简单的制法及生理可接受性而著名。
从EP-A0403959及DE-A3208791的在肠胃道中具有可控溶解度或溶胀度药片表层材料可知,处于未中和状态及加有碱的某些共聚物(a)是已公知的。
此外,US-A4529748公开了未中和聚[甲基丙烯酸,甲基丙烯酸甲酯1.2]作为在假牙粘合剂中的羧甲基纤维素钠上涂层的应用,它借助于通过涂层的逐渐溶解而以羧甲基纤维素钠的形式释放出新粘合剂,因而增加了粘合的持久性。而根据本发明使用至少部分中和的含羧基共聚物作为活性粘合物质则是未被此专利描述过或建议过的。
实施例
实施例1(共聚物(a)的制备)
由1克月桂基硫酸钠,6.7克常用的工业非离子乳化剂,100克水,1.3克硫代甘醇酸乙基己酯及300克单体的混合物,制备一乳液,在聚合过程中将此液在75-85℃下用进料技术在约2-4小时内加至含有500克水的聚合反应器中。在聚合过程中又将引发剂(溶于100克水中的1克过硫酸钠)同样连续加人。为减少残留单体数量,然后加入氧化还原引发剂(叔丁基过氧化氢/抗坏血酸),并使聚合反应继续进行。
为制备聚合物盐,随后将此批料用水冲释,加入所需数量的氧化物或氢氧化物。
最后将所得的聚合物溶液或聚合物分散液进行喷雾干燥。
用此法制得的共聚物列于下表1中。
表1
实施例 | 单体 | 单体比例 | 盐类 | 中和度 |
a | EA-MAS | 1∶1 | Na | 35% |
b | EA-MAS | 1∶1 | Na/Ca=1/6 | 35% |
c | EA-MAS | 1∶1 | Ca | 40% |
d | EA-MAS | 1∶1 | Na/Zn=1/3 | 40% |
e | EA-MAS | 1∶1 | Zn | 40% |
f | MMA-MAS | 2∶1 | Na | 95% |
g | MMA-MAS | 2∶1 | Na/Ca=1/6 | 85% |
h | MMA-MAS | 2∶1 | Na/Sr=/3 | 85% |
i | tBA-MAS | 1∶1 | K | 60% |
j | MMA-MAS | 1∶1 | Na/Zn=1/4 | 45% |
EA=丙烯酸乙酯
MAS=甲基丙烯酸
MMA=甲基丙烯酸甲酯
tBA=丙烯酸叔丁酯
实施例2(制备假牙粘合剂)
将40份喷雾干燥粉末1a至1j(粒径5-200u,水分3.0%重量)在25℃下与20份液体石蜡(110-230mpas)及40份凡士林(Riedel de Haen生产的凡士林)充分混合。
实施例3(与公知的假牙粘合剂比较其粘合性)
为判断假牙粘合剂的有效性,把0.3克每批待测配制物尽可能均匀地涂于两个聚甲基丙烯酸甲酯模塑物之间,并测量把模塑物分开所需的拉力。
在2分钟内测定的所有1a-1j样品的拉为2700-约3000cN。对任何已知粘合剂膏来说未测到大于2640cN的拉力。
Claims (10)
1.一种假牙用粘合剂,它包含:
a)作为活性粘合成分的部份或全部中和共聚物,此共聚物含有占其5-95%重量的通式I的一种或多种丙烯酸酯:
CH2=CR’-COOR I(单体A),式中R’是氢或甲基,R是含1-30个碳原子的烷基,及含占其95-5%重量的甲基丙烯酸和/或丙烯酸(单体B),以及
b)假牙粘合剂中常用的媒介物。
2.如权利要求1所要求的粘合剂,其中共聚物是水溶的。
3.如权利要求1所要求的粘合剂,其中共聚物以钠、钾、钙、镁、锶或锌的单一盐或混合盐形式存在。
4.如权利要求1所要求的粘合剂,其中30-95%的游离羟基的被中和。
5.如权利要求1所要求的粘合剂,其中单体(a)是丙烯酸或甲基丙烯酸的C1-C4烷基酯。
6.如权利要求1所要求的粘合剂,其中共聚物还包含以共聚物计0-30%重量可游离基聚合的单体(单体C),此单体选自丙烯酰胺,甲基丙烯酰胺,N-乙烯基丁内酰胺,丙烯酸羟烷基酯,巴豆酸及马来酸的一种或几种的。
7.如权利要求1所要求的粘合剂,它除含通常的活性粘合剂组合物(a)外,还含作为活性粘合剂组合物的物质,后者选自烷基乙烯基醚马来酸酐共聚物的部分盐,羧甲基纤维素及其盐类,聚乙烯基吡咯烷酮,或乙烯基吡咯烷酮与乙酸乙烯酯的共聚物类藻酸盐,聚乙二醇,聚乙二醇共聚物类一种或几种的混合物。
8.如权利要求1所要求的粘合剂,它含有一种作为活粘合剂组合物(a)的共聚物,此共聚物是占共聚物20-80%重量丙烯酸乙酯或甲基丙烯酸乙酯,及占共聚物80-20%重量的甲基丙烯酸的或丙烯酸的共聚物。
9.一种由5-95%重量通式I的单体和95-5%重量甲基丙烯酸和丙烯酸(单体B)的共聚物在制备假牙用粘合剂中作为活性粘合剂组合物的用途,
CH2=CR′-COOR I(单体A)式中R′是氢或甲基,R是含1-30个碳原子的烷基;此共聚物的分子量为30,000-5,000,000,而且共聚物的全部或部分游离羧基已被中和。
10.制造如权利要求1所要求的假牙用粘合剂的方法,它包括
(i)将通式I的单体A与选自甲基丙烯酸和丙烯酸的单体B进行共聚,
CH2=CR′-COOR I(单体A)式中R′是氢或甲基,R是含1-30个碳原子的烷基;单体A与单体B的重量比例为95∶5至5∶95;
(ii)将所得共聚物完全或部分中和;
(iii)把已中和的共聚物干燥;
(iv)以公知方法把已干燥的聚合物与媒介物混合,制造假牙粘合剂;以及,如果需要
(v)将所得的混合物转为粉末状。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19704293A DE19704293A1 (de) | 1997-02-05 | 1997-02-05 | Zahnprothesenhaftmittel |
DE19704293.7 | 1997-02-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1196232A true CN1196232A (zh) | 1998-10-21 |
Family
ID=7819356
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN98107052A Pending CN1196232A (zh) | 1997-02-05 | 1998-02-05 | 假牙粘合剂 |
Country Status (5)
Country | Link |
---|---|
US (1) | US6080811A (zh) |
EP (1) | EP0857475A3 (zh) |
JP (1) | JPH10218720A (zh) |
CN (1) | CN1196232A (zh) |
DE (1) | DE19704293A1 (zh) |
Cited By (1)
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CN103153263A (zh) * | 2010-03-10 | 2013-06-12 | 宝洁公司 | 义齿粘合剂组合物 |
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DE10220470A1 (de) | 2002-04-30 | 2003-11-20 | Roehm Gmbh | ph-sensitives Polymer |
US8652446B2 (en) | 2000-03-17 | 2014-02-18 | Lg Household & Healthcare Ltd. | Apparatus and method for whitening teeth |
US7785572B2 (en) | 2000-03-17 | 2010-08-31 | Lg Household And Health Care Ltd. | Method and device for teeth whitening using a dry type adhesive |
BRPI0109371B1 (pt) | 2000-03-17 | 2016-02-16 | Lg Household & Health Care Ltd | emplastros do tipo seco para branqueamento dental |
IT1318618B1 (it) * | 2000-07-10 | 2003-08-27 | A C R Applied Coating Res S A | Microsfere bioadesive a rilascio rapido per la somministrazionesublinguale di principi attivi. |
DE10124028B4 (de) * | 2001-05-16 | 2010-02-18 | 3M Espe Ag | Selbstadhäsive Dentalmaterialien |
US6946142B2 (en) * | 2001-06-23 | 2005-09-20 | Lg Household & Healthcare Ltd. | Multi-layer patches for teeth whitening |
EP2314259B1 (en) | 2003-03-14 | 2015-07-29 | Depuy Spine, Inc. | Hydraulic device for injection of bone cement in percutaneous vertebroplasty |
US8066713B2 (en) | 2003-03-31 | 2011-11-29 | Depuy Spine, Inc. | Remotely-activated vertebroplasty injection device |
JP2004307421A (ja) * | 2003-04-09 | 2004-11-04 | Um Dental Co Ltd | 歯科用接着剤および歯科用充填剤 |
JP2004331558A (ja) * | 2003-05-07 | 2004-11-25 | Um Dental Co Ltd | 歯科用セメント組成物 |
JP4230290B2 (ja) * | 2003-06-16 | 2009-02-25 | サンメディカル株式会社 | 歯科用接着材 |
US8415407B2 (en) | 2004-03-21 | 2013-04-09 | Depuy Spine, Inc. | Methods, materials, and apparatus for treating bone and other tissue |
WO2006011152A2 (en) | 2004-06-17 | 2006-02-02 | Disc-O-Tech Medical Technologies, Ltd. | Methods for treating bone and other tissue |
WO2005030034A2 (en) | 2003-09-26 | 2005-04-07 | Depuy Spine, Inc. | Device for delivering viscous material |
JP2007522911A (ja) * | 2004-02-23 | 2007-08-16 | スミスクライン・ビーチャム・コーポレイション | 義歯接着剤の適用方法 |
US20050192376A1 (en) * | 2004-02-26 | 2005-09-01 | Ha Thinh N. | Denture care method and kit |
DE102005031771B4 (de) * | 2005-07-07 | 2007-07-12 | Queisser Pharma Gmbh & Co. Kg | Haftzubereitung für Kieferprothesen |
US9381024B2 (en) | 2005-07-31 | 2016-07-05 | DePuy Synthes Products, Inc. | Marked tools |
US9918767B2 (en) | 2005-08-01 | 2018-03-20 | DePuy Synthes Products, Inc. | Temperature control system |
US8360629B2 (en) | 2005-11-22 | 2013-01-29 | Depuy Spine, Inc. | Mixing apparatus having central and planetary mixing elements |
AU2007297097A1 (en) | 2006-09-14 | 2008-03-20 | Depuy Spine, Inc. | Bone cement and methods of use thereof |
US8950929B2 (en) | 2006-10-19 | 2015-02-10 | DePuy Synthes Products, LLC | Fluid delivery system |
DE102007033096A1 (de) * | 2007-07-13 | 2009-01-15 | Georg-August-Universität Göttingen Stiftung Öffentlichen Rechts Universitätsmedizin | Polymere Haftschicht, insbesondere Zahnersatzprothesen |
AT515834B1 (de) | 2014-06-04 | 2018-09-15 | Magister Hoeveler & Co Ges M B H | Haftmittel für Zahnprothesen und sein Verfahren zur Herstellung |
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AU640474B2 (en) * | 1990-03-29 | 1993-08-26 | Isp Investments Inc. | Copolymers of maleic anhydride and acrylic acid useful in denture adhesives |
-
1997
- 1997-02-05 DE DE19704293A patent/DE19704293A1/de not_active Withdrawn
-
1998
- 1998-02-02 US US09/017,774 patent/US6080811A/en not_active Expired - Fee Related
- 1998-02-03 EP EP98101802A patent/EP0857475A3/de not_active Withdrawn
- 1998-02-04 JP JP10023378A patent/JPH10218720A/ja not_active Withdrawn
- 1998-02-05 CN CN98107052A patent/CN1196232A/zh active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103153263A (zh) * | 2010-03-10 | 2013-06-12 | 宝洁公司 | 义齿粘合剂组合物 |
Also Published As
Publication number | Publication date |
---|---|
US6080811A (en) | 2000-06-27 |
EP0857475A3 (de) | 2000-03-29 |
JPH10218720A (ja) | 1998-08-18 |
DE19704293A1 (de) | 1998-08-06 |
EP0857475A2 (de) | 1998-08-12 |
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