CN1650065A - 涂敷的纤维和织物表面结构 - Google Patents
涂敷的纤维和织物表面结构 Download PDFInfo
- Publication number
- CN1650065A CN1650065A CNA038097621A CN03809762A CN1650065A CN 1650065 A CN1650065 A CN 1650065A CN A038097621 A CNA038097621 A CN A038097621A CN 03809762 A CN03809762 A CN 03809762A CN 1650065 A CN1650065 A CN 1650065A
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- Prior art keywords
- acid
- active principle
- microcapsules
- fiber
- weight
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Abstract
公开一种特别的纤维和织物表面的结构，其特征在于，它们具有(a)微胶囊化的试剂和(b)粘合剂的混合物。
Description
发明领域
本发明属于纺织技术领域，并涉及一种穿着舒适性得到改善的新的涂敷纤维和织物表面结构、其制备方法以及由微胶囊化的有效物质和粘合剂组成的混合物在织物涂敷中的用途。
现有技术
术语“穿着舒适性”概括了使用者提高的要求，不再只满足于直接穿在皮肤上的诸如妇女内衣或连袜裤的衣物不使发痒或皮肤变红，而是完全另一种希望其对皮肤状况起到积极作用。不仅能消除疲劳现象，而且能散发清新的香味或避免皮肤粗糙。
用化妆物质涂敷织物特别是女士连袜裤(这是一个特别吸引人的消费领域)，使化妆品在穿着时转到皮肤上并达到预期效果，在这方面至今不乏努力。显然，该预期作用仅当相应的有效物质转到穿着者皮肤上时才有，也就是说，在或长或短地穿一段时间后，衣服上就没有了有效物质。生产者在选择有效物质时应满足一定要求，在权衡效率、可获得量以及相关成本须找到折衷办法，使该产品的作用是可觉察的，并且顾客能支付其上涨的价格。由于具有所需作用的化妆物质通常情况下是昂贵的，而且涂敷终产品具有外加成本，所以对于生产者来说特别有意义的是，除了涂敷的终产品和穿着者皮肤间的接触外，有效物质不再有其他不希望的损失，因为这使顾客昂贵支付短时间有效的附加的穿着舒适性。洗涤这样涂敷的纤维和织物所造成的有效物质损失是特别不希望出现的。尽管这种损失不能完全避免，但相应产品的生产者显然很关心要以这种方式在纤维上涂敷有效物质使其不再溶解或不再机械解脱。
代替多次进行的浸渍法(其中纤维或织物直接涂敷有效物质)近年来使用微胶囊化的有效物质变得越来越重要。设法使水溶的或可分散于水的有效物质包容在不溶干水的胶囊中，穿着时，通过经膜孔的有控制释放或者通过机械破坏包膜而放出活性物质(prizipien)。与使用未胶囊化的有效物质相比，以这种方式实际上可以显著减少多次洗涤中出现的损失。但所得结果总体上不能长期令人满意，因为胶囊化的有效物质只是松散地位于纤维原纤维间，因此例如由于洗涤过程中的机械作用很容易被洗脱。
所以，本发明的任务在于提供一种没有上述的缺点的，用有效物质涂敷的纤维和织物，也就是说，经多次洗涤还具有有利的性质，洗涤期间没有明显的有效物质损失。
发明描述
本发明的主题是特别的纤维和织物表面结构，其特征在于，该表面结构是用(a)微胶囊化的有效物质和(b)粘合剂组成的混合物涂敷的。
令人惊奇地发现，用微胶囊化的有效物质和粘合剂组成的混合物涂敷纤维和织物，使得微胶囊、因此还有有效物质牢固地粘附到纤维上，因此在洗涤过程中，与微胶囊没有直接粘附到纤维原纤维上的涂敷的终产品相比，更少地快速溶解和洗脱。由此得到涂敷的纤维和织物表面结构，与现有技术的传统产品相比，其额外的护理效果使使用者不仅在长期穿着时并在相同洗涤次数后在长时间段内可感觉到。
市售的皮肤处理剂平均只有2重量％的活性物质，本发明被涂敷的纤维和织物特别的优点还在于，获得的微胶囊的有效物质含量很高，约为20-30重量％。
有效物质
有效物质的选择并非关键性的，只要其在皮肤上能发挥作用。有效物质优选具有保湿性能，是抗蜂窝组织炎和/或自身变褐色的。典型的实例是生育酚、生育酚乙酸酯、生育酚棕榈酸酯、胡萝卜素、咖啡因、抗坏血酸、(脱氧)核糖核酸及其片段产物、β-葡聚糖、视黄醇、红没药醇、尿囊素、植烷三醇、泛酰醇、AHA-酸、氨基酸、神经酰胺、假神经酰胺、脱乙酰壳多糖、二羟基丙酮、醇、角鲨烷、精油(例如霍霍巴油)、植物蛋白质及其水解产物、植物提取物，例如李属提取物、非洲花生(bambamuss)提取物和维生素络合物。特别优选使用的是：
·角鲨烷，
·脱乙酰壳多糖，
·醇，
·视黄醇(维生素A)，
·咖啡因，
·植物蛋白质及其水解产物，
·胡萝卜素，
·霍霍巴油，
因为他们
·有助于皮肤水脂层的平衡，
·防止水损失以及由此形成的皱纹，
·使皮肤新鲜并抗疲劳现象，
·赋予皮肤柔软且有弹性感，
·改善皮肤排泄，养分供给和血液循环，
·抗氧化应力、环境有害物、皮肤老化和自由基的作用，
·补偿因水和阳光引起的脂肪损失，
·改善UV-滤光器的水稳定性，
·保证均匀的褐色色彩，最后还
·具有抗微生物性能。
微胶囊中有效物质的量可以为1-30重量％，优选为5-25重量％，尤其为15-20重量％。
微胶囊
技术人员可以将术语“微胶囊”理解为直径为约0.0001-约5mm的球状聚合体，其含有至少一种固体或液体核，该核至少被一个连续的包膜包围。确切地说，是指有成膜的聚合物所包裹的细微分散的液相或固相，制备时，在乳化和凝聚或界面聚合后聚合物沉积在要包裹的材料上。按照另一方法，将熔融的蜡被吸收在基质(“微海绵”)中，另外有成膜的聚合物将其包裹成微粒。极微小的胶囊(也称为纳米胶囊)被干燥，如粉末一样。除单核微胶囊外，还公开了多核聚合体，也称为微球，其含有分布在连续包膜材料中的二个或多个核。而且，单核或多核的微胶囊可以被另外的第二个、第三个等包膜包围。该包膜可以由天然材料、半合成材料或合成材料构成。天然的包膜材料例如阿拉伯树胶、琼脂、琼脂糖、麦芽糖糊精、藻酸或其盐，例如藻酸钠或藻酸钙、脂肪和脂肪酸、鲸蜡醇、胶原、脱乙酰壳多糖、卵磷脂、明胶、白蛋白、虫胶、诸如淀粉或葡聚糖的多糖、多肽、蛋白质水解物、蔗糖和蜡。半合成的包膜材料是另一种化学改性的纤维素、特别是纤维素酯和纤维素醚，例如乙酸纤维素、乙基纤维素、羟丙基纤维素、羟基丙基甲基纤维素和羧甲基纤维素，以及淀粉衍生物，特别是淀粉醚和淀粉酯。合成的包膜材料例如聚丙烯酸酯、聚酰胺、聚乙烯醇或聚乙烯吡咯烷酮的聚合物。
现有技术中微胶囊的实例是以下的商品(括号里是包膜材料)：HallcrestMicrocapsules(明胶、阿拉伯树胶)、Coletica Thalaspheres(海洋的胶原)、LipotecMillicapseln(藻酸、琼脂)、Induchem Unispheres(乳糖、微晶纤维素、羟基丙基甲基纤维素)；Unicerin C30(乳糖、微晶纤维素、羟基丙基甲基纤维素)、Kobo Glycospheres(改性淀粉、脂肪酸酯、磷脂)、Softspheres(改性琼脂)和KuhsProbiol Nanospheres(磷脂)以及Primaspheres和Primasponges(脱乙酰壳多糖、藻酸盐)和Primasys(磷脂)。
脱乙酰壳多糖微胶囊及其制备方法是专利申请号为[WO01/01926、WO01/01927、WO01/01928、WO01/01929]的先前专利申请的主题。例如可以得到平均直径为0.0001-5mm，优选0.001-0.5mm，特别是0.005-0.1mm的微胶囊，是由包膜和含有有效物质的基质组成的，其中，
(a1)由成胶剂、脱乙酰壳多糖和有效物质配制基质，
(a2)任选地将基质分散在油相中，
(a3)用阴离子聚合物水溶液处理任选分散的基质，并任选地除去油相。或者
(b1)由成胶剂、阴离子聚合物和有效物质配制基质，
(b2)任选地将基质分散在油相中，
(b3)用脱乙酰壳多糖水溶液处理任选分散的基质，并任选地除去油相。
或者
(c1)在乳化剂存在下，用油体将有效物质水性制剂处理成水包油乳液，
(c2)用阴离子聚合物水溶液处理得到的乳液，
(c3)使得到的基质与脱乙酰壳多糖水溶液接触，和
(c4)从水相分离得到的胶囊产物。
成胶剂
就本发明的意义而言，优选考虑这样的物质作为成胶剂，其在40℃温度以上的水溶液中表现出形成凝胶的性质。本文的典型的实例是杂多糖和蛋白质。作为热致胶化的杂多糖优选是琼脂糖，其以从红藻门得到的琼脂形式，以及与低于30重量％的不成胶的琼脂胶一起的形式存在。琼脂糖的主要成分是由D-半乳糖和3，6-脱水-L-半乳糖组成的线性多糖，其交替结合有β-1，3-苷和β-1，4-苷。杂多糖的分子量优选为110000-160000，而且是无色和无味的。作为交替可以是果胶、黄原胶(也叫黄原酸胶)及其混合物。还优选以下类型，其在1重量％水溶液中形成凝胶，不低于80℃时融化，40℃以上时已再次固化。从热致胶化的蛋白质中列举示例性的不同明胶种类。
脱乙酰壳多糖
脱乙酰壳多糖是生物聚合物，属于氢化胶类(Hydro Rolloide)。化学上，它们是不同分子量的部分脱乙酰的壳多糖，其含有以下的理想的单体单元。
与在生物pH值范围内带负电荷的多数氢化胶类不同，脱乙酰壳多糖在该条件下是阳离子生物聚合物。带正电荷的脱乙酰壳多糖可与带相反电荷的表面相互作用，并因此可用于化妆的护发和护肤制剂和药物制品中。脱乙酰壳多糖是由壳多糖制备，优选甲壳动物的残壳，这是可大量得到的廉价原料。在Hackmann等人首次描述的一种工艺中，通常先添加碱使壳多糖脱蛋白，添加无机酸脱矿质，接着添加强碱脱乙酰，其中分子量分布可以很宽。优选使用以下类型，其平均分子量为10000-500000，或800000-1200000道尔顿，和/或Brookfield(布洛克菲尔德)粘度(1重量％，在乙醇酸中)低于5000mPas(毫帕·秒)。脱乙酰度为80-88％，灰分含量低于0.3重量％。由于水溶性更好通常以盐形式使用，优选以甘醇酸盐形式使用脱乙酰壳多糖。
油相
在形成膜前，任选将基质分散在油相中。符合该目的的油例如，基于6-18，优选8-10个碳原子的脂肪醇的格尔伯特(Guerbet)醇，直链C6-C22脂肪酸与直链C6-C22脂肪醇的酯，支链C6-C13羧酸与直链C6-C22脂肪醇的酯，如肉豆蔻酸肉豆蔻酯、棕榈酸肉豆蔻酯、硬脂酸肉豆蔻酯、异硬脂酸肉豆蔻酯、油酸肉豆蔻酯、山嵛酸肉豆蔻酯、瓢儿菜酸肉豆蔻酯、肉豆蔻酸鲸蜡酯、棕榈酸鲸蜡酯、硬脂酸鲸蜡酯、异硬脂酸鲸蜡酯、油酸鲸蜡酯、山嵛酸鲸蜡酯、瓢儿菜酸鲸蜡酯、肉豆蔻酸硬脂基酯、棕榈酸硬脂基酯、硬脂酸硬脂基酯、异硬脂酸硬脂基酯、油酸硬脂基酯、山嵛酸硬脂基酯、瓢儿菜酸硬脂基酯、肉豆蔻酸异硬脂基酯、棕榈酸异硬脂基酯、硬脂酸异硬脂基酯、异硬脂酸异硬脂基酯、油酸异硬脂基酯、山嵛酸异硬脂基酯、油酸异硬脂基酯、肉豆蔻酸油基酯、棕榈酸油基酯、硬脂酸油基酯、异硬脂酸油基酯、油酸油基酯、山嵛酸油基酯、瓢儿菜酸油酯、肉豆蔻酸山嵛酯、棕榈酸山嵛酯、硬脂酸山嵛酯、异硬脂酸山嵛酯、油酸山嵛酯、山嵛酸山嵛酯、瓢儿菜酸山嵛酯、肉豆蔻酸瓢儿菜酯、棕榈酸瓢儿菜酯、硬脂酸瓢儿菜酯、异硬脂酸瓢儿菜酯、油酸瓢儿菜酯、山嵛酸瓢儿菜酯、瓢儿菜酸瓢儿菜酯。此外，可考虑直链C6-C22脂肪酸与支链醇特别是2-乙基己醇的酯，羟基羧酸与直链或支链C6-C22脂肪醇的酯，特别是马来酸二辛酯，直链和/或支链脂肪酸与多元醇(例如丙二醇、二聚二醇或三聚三醇)和/或格尔伯特醇的酯，基于C6-C10脂肪酸的甘油三酸酯，基于C6-C18脂肪酸的液态的甘油单酸酯/二酸酯/三酸酯的混合物，C6-C22脂肪醇和/或格尔伯特醇与芳香羧酸特别是安息香酸的酯，C2-C12二羧酸与直链或支链的1-22个碳原子的醇或者具有2-10个碳原子和2-6个羟基的多元醇的酯，植物油，支链伯醇，取代的环己烷，直链和支链C6-C22脂肪醇羧酸酯，格尔伯特羧酸酯，安息香酸与直链和/或支链C6-C22醇(例如FinsolvTN)的酯，每个烷基具有6-22个碳原子的直链或支链、对称或不对称的二烷基醚，与多元醇的环氧化脂肪酸酯的开环产物，硅油和/或脂肪烃或环烷烃，例如角鲨烷、角鲨烯或二烷基环己烷。
阴离子聚合物
阴离子聚合物的目的是与脱乙酰壳多糖形成膜。优选藻酸盐适合该目的。藻酸是具有以下理想的单体单元的含有羧基的多糖混合物：
藻酸或藻酸盐的平均分子量为150000-250000。这里的藻酸盐是其全部或部分中和的产物，特别是碱金属盐，其中优选藻酸钠(“Algin”)以及铵盐或碱土金属盐。特别优选混合藻酸盐，例如钠/镁或钠/钙藻酸盐。在本发明的一可选实施方案中，阴离子的脱乙酰壳多糖衍生物也是符合目的的，例如羧基化产物，首先是琥珀酰基化产物。也可选择平均分子量为5000-50000道尔顿的聚(甲基)丙烯酸酯和各种羧甲基纤维素。代替阴离子聚合物，还可使用阴离子表面活性剂或低分子量的无机盐，例如焦磷酸盐，以形成包膜。
乳化剂
例如至少选自以下的非离子表面活性剂中之一作为乳化剂：
·2-30摩尔环氧乙烷和/或0-5摩尔环氧丙烷在8-22个碳原子的直链脂肪醇上、在12-22个碳原子的脂肪酸上、在烷基有8-15个碳原子的烷基酚上以及在烷基有8-22个碳原子的烷基胺上的加成产物；
·在烷基(链烯基)和其环氧化类似物有8-22个碳原子的烷基和/或链烯基低聚苷；
·1-15摩尔环氧乙烷在蓖麻油和/或氢化蓖麻油上的加成产物；
·15-60摩尔环氧乙烷在蓖麻油和/或氢化蓖麻油上的加成产物；
·甘油和/或脱水山梨糖醇与12-22个碳原子的不饱和的、直链或饱和的、支链的脂肪酸和/或具有3-18个碳原子的羟基羧酸的偏酯及其与1-30摩尔环氧乙烷的加合物；
·聚丙三醇(平均自缩合度为2-8)、聚乙二醇(分子量为400-5000)、三甲基醇丙烷、季戊四醇、糖醇(例如山梨糖醇)、烷基葡萄糖苷(例如甲基葡萄糖苷、丁基葡萄糖苷、月桂基葡萄糖苷)以及聚葡糖苷(例如纤维素)与饱和和/或不饱和的、直链或支链的12-22个碳原子的脂肪酸和/或具有3-18个碳原子的羟基羧酸的偏酯以及其与1-30摩尔环氧乙烷的加合物；
·由季戊四醇、脂肪酸、柠檬酸和脂肪醇组成的混合酯和/或由具有6-22个碳原子的脂肪酸、甲基葡萄糖和多元醇优选甘油或聚甘油组成的混合酯；
·单、二和三烷基磷酸酯以及单-、二-和/或三-PEG烷基磷酸酯及其盐；
·羊毛蜡醇；
·聚硅氧烷-聚烷基-聚醚共聚物或相应的衍生物；
·嵌段共聚物，例如聚乙二醇-30二聚羟基硬脂酸酯；
·聚合物乳化剂，例如Goodrich的Pemulen类型(TR-1、TR-2)；
·聚亚烷基二醇以及
·甘油羧酸酯。
环氧乙烷加成产物
环氧乙烷和/或环氧丙烷在脂肪醇、脂肪酸、烷基酚上或在蓖麻油上的加成产物都是公知的市售产品。它们是同系物混合物，其平均烷氧基化度相当于环氧乙烷和/或环氧丙烷与其进行加成反应的基质的物质量之比。环氧乙烷在甘油上的加成物的C12/18-脂肪酸单酯和二酯作为化妆品的回脂剂是已知的。
烷基和/或链烯基低聚苷
烷基和/或链烯基低聚苷、其制备和应用在现有技术中是已知的。其制备尤其是通过葡萄糖或低聚糖与8-18个碳原子的伯醇反应而进行。关于苷基，既可以是环糖单元通过苷链连接到脂肪醇的单苷，也可以是低聚度优选在至多8的低聚苷。低聚合度是基于这种工业级产品通常的同系物分布的统计平均值。
偏甘油酯
合适的偏甘油酯的典型实例是羟基硬脂酸单甘油酯、羟基硬脂酸二甘油酯、异硬脂酸单甘油酯、异硬脂酸二甘油酯、油酸单甘油酯、油酸二甘油酯、蓖麻油酸单甘油酯、蓖麻油酸二甘油酯、亚油酸单甘油酯、亚油酸二甘油酯、亚麻酸单甘油酯、亚麻酸二甘油酯、瓢儿菜酸单甘油酯、瓢儿菜酸二甘油酯、酒石酸单甘油酯、酒石酸二甘油酯、柠檬酸单甘油酯、柠檬酸二甘油酯、苹果酸单甘油酯、苹果酸二甘油酯及其工业混合物，其从属地以少量含在制备过程产生的三甘油酯中。1-30摩尔，优选5-10摩尔的环氧乙烷与所述偏甘油酯的加成产物也是合适的。
脱水山梨糖醇酯
作为脱水山梨糖醇酯的是失水山梨糖醇单异硬脂酸酯、失水山梨糖醇倍半异硬脂酸酯、失水山梨糖醇二异硬脂酸酯、失水山梨糖醇三异硬脂酸酯、失水山梨糖醇单油酸酯、失水山梨糖醇倍半油酸酯、失水山梨糖醇二油酸酯、失水山梨糖醇三油酸酯、失水山梨糖醇单瓢儿菜酸酯、失水山梨糖醇倍半瓢儿菜酸酯、失水山梨糖醇二瓢儿菜酸酯、失水山梨糖醇三瓢儿菜酸酯、失水山梨糖醇单蓖麻酸酯、失水山梨糖醇倍半蓖麻酸酯、失水山梨糖醇二蓖麻酸酯、失水山梨糖醇三蓖麻酸酯、失水山梨糖醇单羟基硬脂酸酯、失水山梨糖醇倍半羟基硬脂酸酯、失水山梨糖醇二羟基硬脂酸酯、失水山梨糖醇三羟基硬脂酸酯、失水山梨糖醇单酒石酸酯、失水山梨糖醇倍半酒石酸酯、失水山梨糖醇二酒石酸酯、失水山梨糖醇三酒石酸酯、失水山梨糖醇单柠檬酸酯、失水山梨糖醇倍半柠檬酸酯、失水山梨糖醇二柠檬酸酯、失水山梨糖醇三柠檬酸酯、失水山梨糖醇单马来酸酯、失水山梨糖醇倍半马来酸酯、失水山梨糖醇二马来酸酯、失水山梨糖醇三马来酸酯及其工业混合物。1-30摩尔，优选5-10摩尔的环氧乙烷与所述脱水山梨糖醇酯的加成产物同样是合适的。
聚甘油酯
合适的聚甘油酯的典型实例是聚甘油-2二聚羟基硬脂酸酯(DehymulsPGPH)、聚甘油-3二异硬脂酸酯(LamefornTGI)、聚甘油-4异硬脂酸酯(IsolanGI 34)、聚甘油-3油酸酯、二异硬脂酰基聚甘油-3二异硬脂酸酯(IsolanPDI)、聚甘油-3甲基葡萄糖二硬脂酸酯(Tego Care450)、聚甘油-3蜂蜡(CeraBellina)、聚甘油-4癸酸酯(Polyglycerol Caprate 2010/90)、聚甘油-3鲸蜡基醚(ChimexaneNL)、聚甘油-3二硬脂酸酯(CremophorGS 32)、聚蓖麻醇酸聚甘油酯(AdmulWOL 1403)和二聚异硬脂酸聚甘油酯及其混合物。其他适合的多元醇酯的实例是任选地与1-30摩尔环氧乙烷反应的三甲基醇丙烷或季戊四醇和月桂酸、椰子脂肪酸、牛(talg)脂肪酸、棕榈酸、硬脂酸、油酸、山嵛酸等的单酯、二酯和三酯。
阴离子乳化剂
典型的阴离子乳化剂是具有12-22个碳原子的脂族脂肪酸，例如棕榈酸、硬脂酸或山嵛酸，以及具有12-22个碳原子的二羧酸，例如壬二酸或癸二酸。
两性和阳离子乳化剂
此外，可使用两性离子表面活性剂作乳化剂。作为两性离子表面活性剂是指那些在分子中至少有一个季铵基和至少一个羧酸基和一个磺酸基的表面活性化合物。特别合适的两性离子表面活性剂是所谓的甜菜碱如N-烷基-N，N-二甲基甘氨酸铵，例如椰子烷基二甲基甘氨酸铵、N-酰基氨丙基-N，N-二甲基甘氨酸铵、例如椰子酰基氨丙基二甲基甘氨酸铵、和烷基或酰基有8-18个碳原子的2-烷基-3-羧基甲基-3-羟乙基咪唑啉以及椰子酰基氨乙基羟乙基羧甲基甘氨酸酯。特别优选的是称为CTFA的椰子酰氨丙基甜菜碱(Cocamidopropyl Betaine)的已知脂肪酰胺衍生物。两性表面活性剂也是适用的乳化剂。两性表面活性剂是指那些在分子中除了C8/18-烷基或酰基外还至少含有一个游离的氨基和至少一个-COOH或-SO3H基并能形成内盐的表面活性化合物。合适的两性表面活性剂的实例是N-烷基甘氨酸、N-烷基丙酸、N-烷基氨基奶油酸、N-烷基亚氨基二丙酸、N-羟乙基-N-烷基酰氨基丙基甘氨酸、N-烷基牛磺酸、N-烷基肌氨酸、2-烷基氨基丙酸和烷基氨基醋酸，其中烷基有约8-18个碳原子。特别优选的两性表面活性剂是N-椰子烷基氨基丙酸酯、椰子酰基氨乙基氨基丙酸酯和C12/18-酰基肌氨酸。最后，阳离子表面活性剂也适合作乳化剂，其中特别优选季铵酯(esterquats)类，优选甲基季铵化的二脂肪酸三乙醇胺酯-盐。
微胶囊的制备方法
为制备微胶囊，通常制备1-10重量％，优选2-5重量％的成胶剂(优选琼脂)的水溶液，并在回流下加热。在沸点，优选80-100℃，加入含有0.1-2重量％，优选0.25-0.5重量％脱乙酰壳多糖以及0.1-25重量％，尤其是0.25-10重量％有效物质的第二种水溶液；该混合物作为基质。微胶囊上的有效物质同样可以是胶囊重量的0.1-25重量％。如果需要，这时还可加入水溶性的成分如无机颜料以调节粘度，通常以水或水/醇的分散体形式加入。此外，向基质中加入乳化剂和/或溶剂有利于有效物质的乳化或分散。由成胶剂、脱乙酰壳多糖和有效物质制得基质后，为了在随后胶囊化时能制得尽可能小的微粒，任选地在强剪切下将基质非常精细地分散在油相中。已证明，将基质加热到40-60℃温度，而油相冷却到10-20℃是特别有利的。最后，再次进行原来的胶囊化的必要步骤，即通过基质中的脱乙酰壳多糖与阴离子聚合物接触而形成包膜。在40-100℃，优选50-60℃温度时，用约1-50重量％的水溶液，优选10-15重量％的阴离子聚合物水溶液处理任选分散在油相中的基质是有利的，如果需要，同时或随后除去油相。得到的水溶液制剂的微胶囊含量一般为1-10重量％。很多情况下，如果聚合物溶液含有其他的添加剂如乳化剂或防腐剂是有利的。过滤后得到微胶囊，其平均直径优选约为1mm。为保证尽可能均匀的尺寸分布，筛分胶囊是有利的。所得的微胶囊在制备条件范围内具有任意的形式，不过优选是近似球形的。任选还可使用阴离子聚合物制备基质，并用脱乙酰壳多糖进行胶囊化。
在制备本发明微胶囊的一种可选方法中首先配制水包油乳液，其除了油体、水和有效物质外，含有有效量的乳化剂。在强烈搅拌下该制剂与相应量的阴离子聚合物水溶液混合以制备基质。通过添加脱乙酰壳多糖溶液形成膜。整个过程优选在pH＝3-4的弱酸中进行。如果需要，通过添加无机酸来调节pH。形成膜后，例如通过添加三乙醇胺或其他的碱将pH值升高到5-6。为了增加粘度还加入其他的增稠剂，例如多糖类，尤其是黄原胶、瓜耳胶、琼脂、藻酸酯和纤基乙酸钠、羧甲基纤维素和羟乙基纤维素、脂肪酸的较高分子量的聚乙二醇单酯和二酯、聚丙烯酸酯、聚丙烯酰胺等。最后，例如通过滗析、过滤或离心分离将微胶囊从水相分离。
粘合剂
本发明所用的粘合剂选自以下：
(b1)蜜胺化合物聚合物，
(b2)乙二醛化合物聚合物，
(b3)硅酮化合物聚合物，
(b4)氯甲代氧丙环交联的聚酰氨基胺类，
(b5)聚(甲基)丙烯酸酯，
(b6)聚亚烷基二醇和
(b7)氟烃聚合物。
粘合剂(b1)-(b4)优选适合于制备微胶囊化的有效物质制剂，用该制剂浸渍纤维或织物的表面结构，而粘合剂(b5)-(b7)优选用于那些通过强行涂布而获得的制剂。
蜜胺化合物聚合物
蜜胺(同义词：2，4，6-三氨基-1，3，5-三嗪)通常是由二氰二酰胺的三聚而形成，或按以下反应式，在分裂二氧化碳和氨下由尿素的环化而形成：
本发明的蜜胺低聚物或聚合物是指蜜胺与甲醛、尿素、酚或其混合物的缩合产物。
乙二醛化合物聚合物
乙二醛(同义词：草醛、乙二醛)是在银催化剂存在下，乙二醇与空气进行气相氧化而形成的。本发明的乙二醛是指乙二醛的自缩合产物(“聚乙二醛”)。
硅酮化合物聚合物
合适的硅酮化合物例如二甲基聚硅氧烷、甲基苯基-聚硅氧烷、环硅氧烷以及氨基-、脂肪酸-、醇-、聚醚-、环氧-、氟-、苷-和/或烷基改性的硅酮化合物，其在室温优选以固态或树脂状态存在。此外，Simethicone是合适的，其是由带有平均链长为200-300的二甲基硅氧烷单元的dimethicone和氢化的硅酸盐组成的混合物。
氯甲代氧丙环交联的聚酰氨基胺类
氯甲代氧丙环交联的聚酰氨基胺类也称为“纤维骨(fibrabone)”或“湿强树脂(wet strength resin)”，在纺织和造纸业中是充分公开的。其制备方法优选两种：
i)聚氨基酰胺是(a)首先与5-30摩尔％(基于用于季铵化的氮)的季铵化试剂反应，和(b)接着所得的季铵化聚氨基酰胺与一种其含量相当于未季铵化的氮摩尔量的氯甲代氧丙环进行交联，或者
ii)(a)聚氨基酰胺首先在10-35℃时与5-40摩尔％(基于用于交联的氮)的氯甲代氧丙环反应，和(b)在pH值为8-11，温度为20-45℃时，中间产物与其余量的氯甲代氧丙环交联，使得总的摩尔使用比为90-125摩尔％(基于用于交联的氮)。
聚(甲基)丙烯酸酯
术语“聚(甲基)丙烯酸酯”是指丙烯酸、甲基丙烯酸以及任选的其酯(特别是与诸如甲醇、乙醇、异丙醇、丁醇同分异构体、环己醇等低醇形成的酯)的均聚和共聚产物，是以已知方式例如通过UV射线下的游离基聚合反应而得到的。聚合物的平均分子量一般为10-10000，优选200-5000，尤其是400-2000道尔顿。
聚亚烷基二醇
术语“聚亚烷基二醇”是指环氧乙烷、环氧丙烷以及任选的环氧丁烷的均聚和共聚产物。环氧烷的缩合可以在碱性催化剂存在下以已知方式进行，虽然酸性催化剂是优选的。若使用混合物，例如环氧乙烷和环氧丙烷，则聚合物可以具有嵌段或随机分布。聚合物的平均分子量一般为10-10000，优选200-5000，尤其是400-2000道尔顿。
使用量
微胶囊和粘合剂的使用量比可以为90∶10-10∶90，优选75∶25-25∶75，尤其是60∶40-40∶60重量份。根据制备方法以及微胶囊和粘合剂的使用比例，可以实现不同的粘着类型。使用少量粘合剂(例如微胶囊与粘合剂的重量比大于50∶50)时，在粘合剂层中的微胶囊粘着在原纤维上，导致在穿着时，包膜和皮肤表面直接接触。显然在这粘着类型(“载体(trager)型”)时，由于机械摩擦，可以很快释放有效物质。另一方面，使用大量粘合剂(例如微胶囊与粘合剂的重量比小于50∶50)时，通常这足以使微胶囊不仅粘着在纤维上，而且因而包裹或具有一涂层(“Iglu型”)。以这种方式涂敷微胶囊的纤维在穿着时不直接与皮肤表面结合，使得虽然以较少量放出微胶囊，但经过较长时间还是有效的(参见附图1和2)。通常市售的该制剂是水分散体形式，其固体含量为5-50重量％，优选10-40重量％，尤其是15-30重量％。
工业实用性
由微胶囊化的有效物质和粘合剂组成的制剂用于涂敷纤维和所有种类的织物表面结构，既可以是成品也可以是生产过程中或之后的半成品，目的是以此方式改善皮肤上的穿着舒适性。纤维和织物所形成材料的选择不是最关键性的。所有常用的天然或合成材料及其混合物是合适的，但尤其是棉花、聚酰胺、聚酯、粘胶纤维、聚酰胺/合成弹力纤维、棉花/合成弹力纤维和棉花/聚酯。织物的选择也不是关键性的，显然要涂敷那些与皮肤直接接触的产品，还尤其是内衣、浴衣(bademode)、睡衣、袜子和连袜裤。
使用方法
本发明的另一主题涉及涂敷纤维和织物表面结构的第一种方法，该方法中，用含有微胶囊化的有效物质和粘合剂的水制剂浸渍基质。例如按以下方式进行浸渍，在市售洗衣机中用本发明的制剂处理纤维和织物，或者借助于浸渍浴(Tauchbade)进行使用。
可选的本发明的另一主题涉及涂敷纤维和织物表面结构的第二种方法，该方法中，含有微胶囊化的有效物质和粘合剂的水制剂被强行涂布。其中，将待涂敷的物质通过含有微胶囊化的有效物质和粘合剂的浸渍浴(Tauchbad)，然后在压力下经施压而进行使用。
基于漂浮物或浸渍浴的使用浓度一般为1-90重量％，优选5-60重量％。浸渍情况下，为了使微胶囊化的有效物质在纤维或织物表面结构上达到与强行涂布时同样的负载，一般而言，浸渍比强行涂布需要更高的浓度。
本发明最后的主题涉及含有(a)微胶囊化的有效物质和(b)粘合剂的混合物用于涂敷纤维和织物表面结构的用途。
实施例
制备例H1：在带有搅拌器和回流冷凝器的500ml三颈烧瓶中，在沸点温度将3g琼脂溶解在200ml水中。接着在约30分钟内，在强烈搅拌下，混合物首先与10g甘油和2g滑石在100g水中的均匀分散体进行混合，然后与25g脱乙酰壳多糖(Hydagen DCMF，1重量％在乙醇酸中，Cognis，Düsseldorf/FRG)、5g角鲨烷、0.5g Phenonip(含有苯氧基乙醇和对羟基苯甲酸酯的防腐剂混合物)和0.5g多乙氧基醚-20(Tween 20，ICI)在100g水中的制剂进行混合。所得的基质进行过滤，加热到60℃，滴入0.5重量％的藻酸钠溶液中。筛分后，得到一种水性制剂，含有8重量％的平均直径为1mm的微胶囊。最后，微胶囊(以固体含量计)与聚乙二醇(M＝5000)以40∶60重量比进行混合。
制备例H2：在带有搅拌器和回流冷凝器的500ml三颈烧瓶中，在沸点温度将3g琼脂溶解在200ml水中。接着在约30分钟内，在强烈搅拌下，混合物首先与10g甘油和2g滑石在100g水中的均匀分散体进行混合，然后与25g脱乙酰壳多糖(Hydagen DCMF，1重量％在乙醇酸中，Cognis，Düsseldorf/FRG)、5g生育酚、0.5g Phenonip(含有苯氧基乙醇和对羟基苯甲酸酯的防腐剂混合物)和0.5g多乙氧基醚-20(Tween 20，ICI)在100g水中的制剂进行混合。所得的基质进行过滤，升温到50℃，在强烈搅拌下分散在事先被冷却到15℃的2.5倍体积的石蜡油中。接着用含有1重量％月桂基硫酸钠和0.5重量％藻酸钠的水溶液冲洗分散体，然后多次用的0.5重量％phenonip水溶液冲洗，并除去油相。筛分后，得到一种水制剂，含有8重量％平均直径为1mm的微胶囊。最后，微胶囊(以固体含量计)与聚甲基丙烯酸酯(M＝8000)以50∶50重量比进行混合。
制备例H3：在带有搅拌器和回流冷凝器的500ml三颈烧瓶中，在沸点温度将3g琼脂溶解在200ml水中。接着在约30分钟内，在强烈搅拌下，混合物首先与10g甘油和2g滑石在100g水中的均匀分散体进行混合，然后与25g脱乙酰壳多糖(Hydagen DCMF，1重量％在乙醇酸中，Cognis，Düsseldorf/FRG)、5g咖啡因、0.5g Phenonip(含有苯氧基乙醇和对羟基苯甲酸酯的防腐剂混合物)和0.5g多乙氧基醚-20(Tween 20，ICI)在100g水中的制剂进行混合。所得的基质进行过滤，加热到60℃，滴入15重量％的十二烷基硫酸钠溶液中。筛分后，得到一种水制剂，含有9重量％平均直径为1mm的微胶囊。最后，微胶囊(以固体含量计)与蜜胺-甲醛缩合物(M＝8000)以50∶50重量比进行混合。
制备例H4：在带有搅拌器和回流冷凝器的500ml三颈烧瓶中，在沸点温度将3g琼脂溶解在200ml水中。接着在约30分钟内，在强烈搅拌下，混合物首先与10g甘油和2g滑石在100g水中的均匀分散体进行混合，然后与25g脱乙酰壳多糖(Hydagen DCMF，1重量％在乙醇酸中，Cognis，Düsseldorf/FRG)、5g甲醇、0.5g Phenonip(含有苯氧基乙醇和对羟基苯甲酸酯的防腐剂混合物)和0.5g多乙氧基醚-20(Tween 20，ICI)在100g水中的制剂进行混合。所得的基质进行过滤，加热到60℃，滴入15重量％的焦磷酸钠溶液中。筛分后，得到一种水制剂，含有8重量％平均直径为1mm的微胶囊。最后，微胶囊(以固体含量计)与聚乙二醇(M＝5000)以70∶30重量比进行混合。
制备例H5：在带有搅拌器和回流冷凝器的500ml三颈烧瓶中，在沸点温度将3g琼脂溶解在200ml水中。接着在约30分钟内，在强烈搅拌下，混合物首先与10g甘油和2g滑石在100g水中的均匀分散体进行混合，然后与25g脱乙酰壳多糖(Hydagen DCMF，1重量％在乙醇酸中，Cognis，Düsseldorf/FRG)、5g β-胡萝卜素、0.5g Phenonip(含有苯氧基乙醇和对羟基苯甲酸酯的防腐剂混合物)和0.5g多乙氧基醚-20(Tween 20，ICI)在100g水中的制剂进行混合。所得的基质进行过滤，升温到50℃，在强烈搅拌下分散在事先被冷却到15℃的2.5倍体积的石蜡油中。接着用15重量％焦磷酸钠溶液冲洗分散体，然后多次用的0.5重量％phenonip水溶液冲洗，并除去油相。筛分后，得到一种水制剂，含有1 0重量％微胶囊，其平均直径为1mm。最后，微胶囊(以固体含量计)与聚乙二醇(M＝5000)以70∶30重量比进行混合。
制备例H6：在带有搅拌器和回流冷凝器的500ml三颈烧瓶中，在沸点温度将3g明胶溶解在200ml水中。接着在约30分钟内，在强烈搅拌下，混合物首先与10g甘油和2g滑石在100g水中的均匀分散体进行混合，然后与25g脱乙酰壳多糖(Hydagen DCMF，1重量％在乙醇酸中，Henkel KGaA，Düsseldorf/FRG)、5g大豆蛋白质、0.5g Phenonip在100g水中的制剂进行混合。所得的基质进行过滤，加热到60℃，滴入0.5重量％的Hydagen SCD(琥珀酰化的脱乙酰壳多糖，Cognis)溶液中。筛分后，得到一种水制剂，含有8重量％平均直径为1mm的微胶囊。最后，微胶囊(以固体含量计)与聚乙二醇(M＝5000)以70∶30重量比进行混合。
制备例H7：在带有搅拌器和回流冷凝器的500ml三颈烧瓶中，在沸点温度将3g琼脂溶解在200ml水中。接着在约30分钟内，在强烈搅拌下，混合物首先与10g甘油和2g滑石在100g水中的均匀分散体进行混合，然后与25g脱乙酰壳多糖(Hydagen DCMF，1重量％在乙醇酸中，Cognis，Düsseldorf/FRG)、5g霍霍巴油、0.5g Phenonip(含有苯氧基乙醇和对羟基苯甲酸酯的防腐剂混合物)和0.5g多乙氧基醚-20(Tween 20，ICI)在100g水中的制剂进行混合。所得的基质进行过滤，加热到60℃，滴入0.5重量％的藻酸钠溶液中。接着筛分该制剂以得到同样直径的微胶囊。最后，微胶囊(以固体含量计)与聚乙二醇(M＝5000)以70∶30重量比进行混合。
制备例H8：在搅拌仪器中，将0.5g防腐剂(Phenonip)溶解在50g 2重量％的羟甲基纤维素的水制剂中，调节混合物的pH＝3.5。接着在强烈搅拌下加入由1g生育酚和0.5g失水山梨糖醇单硬脂酸酯+20EO(Eumulgin？SMS 20，Cognis Deutschland GmbH)组成的混合物。然后在进一步搅拌下加入1重量％的脱乙酰壳多糖的乙醇酸(Hydagen CMF Deutschland GmbH)溶液，其加入量使脱乙酰壳多糖的浓度调节为制剂的0.075重量％。接着通过加入三乙胺将pH值升高到5.5，并滗析所形成的微胶囊。最后，微胶囊(以固体含量计)与聚乙二醇(M＝5000)以40∶60重量比进行混合。
制备例H9：在搅拌仪器中，将0.5g防腐剂(Phenonip)溶解在50g 2重量％的聚丙烯酸(Pemulen TR-2)的水制剂中，调节其pH为3。接着在强烈搅拌下加入由1g醇和0.5g失水山梨糖醇单月桂酸酯+15EO(Eumulgin SML 15，Cognis Deutschland GmbH)组成的混合物。然后在进一步搅拌下加入1重量％脱乙酰壳多糖的乙醇酸(Hydagen CMF Deutschland GmbH)溶液，其加入量使脱乙酰壳多糖的浓度调节为制剂的0.01重量％。接着通过加入三乙胺将pH值升高到5.5，并滗析所形成的微胶囊。最后，微胶囊(以固体含量计)与聚乙二醇(M＝5000)以40∶60重量比进行混合。
制备例H10：在搅拌仪器中，将0.5g防腐剂(Phenonip)溶解在50g 2重量％的聚丙烯酸(Pemulen TR-2)的水制剂中，调节其pH为3。接着在强烈搅拌下加入由1g咖啡因和0.5g椰子葡糖苷(Plantacare APG 1200，CognisDeutschland GmbH)组成的混合物。然后在进一步搅拌下加入1重量％脱乙酰壳多糖的乙醇酸(Hydagen CMF Deutschland GmbH)溶液，其加入量使脱乙酰壳多糖的浓度调节为制剂的0.01重量％。接着通过加入三乙胺将pH值升高到5.5，并滗析所形成的微胶囊。最后，微胶囊(以固体含量计)与聚乙二醇(M＝5000)以40∶60重量比进行混合。
应用例1：通过强行涂布，用制备实施例H8的微胶囊制剂涂敷市售的连袜裤，由30个自愿者组成的调查对象测试8-48小时。每8小时后测定有效物质的剩余含量。为了比较，用涂敷有同样的微胶囊但未加入粘合剂的连袜裤重复该试验。结果列于表1中，以平均值表示。
表1
剩余有效物质作为穿着时间的函数
| 穿着时间[d] | 0 | 8 | 16 | 24 | 32 | 40 | 48 |
| 有效物质含量[％-相对值.] | |||||||
| 本发明实施例H8 | 100 | 90 | 82 | 78 | 72 | 62 | 62 |
| 没有粘合剂的对比 | 100 | 80 | 71 | 59 | 40 | 32 | 18 |
可见，用微胶囊和粘合剂组成的混合物涂敷导致有效物质较少迅速释放。
应用例2：通过强行涂布，用制备例H8的微胶囊制剂涂敷市售的连袜裤，(a)在洗衣机中洗涤(30分钟，20℃，1g/L洗涤剂细粉)30次，或者(b)用手洗涤(15分钟，20℃，1g/L洗涤剂细粉)30次。每次洗涤循环后测定有效物质剩余含量。为了比较，用涂敷有同样的微胶囊但未加入粘合剂的连袜裤重复该试验。结果列于表2中。
表2
剩余有效物质作为洗涤循环的函数
| 洗涤循环 | 0 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 15 | 20 | 25 | 30 |
| 洗衣机洗涤时有效物质含量[％-相对值.] | |||||||||||||||
| 本发明实施例H8 | 100 | 70 | 58 | 50 | 42 | 40 | 38 | 37 | 33 | 30 | 28 | 22 | 20 | 18 | 16 |
| 没有粘合剂的对比例 | 100 | 60 | 39 | 21 | 5 | 0 | |||||||||
| 手洗时有效物质含量％-相对值.] | |||||||||||||||
| 本发明实施例H8 | 100 | 90 | 88 | 82 | 78 | 76 | 74 | 72 | 71 | 70 | 69 | 52 | 45 | 42 | 41 |
| 没有粘合剂的对比例 | 100 | 81 | 66 | 51 | 32 | 12 | 3 | 0 | |||||||
可见，用微胶囊和粘合剂组成的混合物涂敷导致不但用洗衣机洗涤时而且用手洗时有效物质较少迅速释放。
应用例3：通过强行涂布，用制备例H10的微胶囊制剂涂敷市售的连袜裤，由10个自愿者组成的调查对象穿着6小时。然后相对于未处理状态，用Corneometer 805PC测定皮肤的水合作用。为了比较，用涂敷有同样的微胶囊但未加入粘合剂的连袜裤重复该试验。结果列于表3。
表3
水合作用的上升
| 被试者 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 平均 |
| 水合作用的上升[％-相对值.] | |||||||||||
| 本发明实施例H10 | 6 | 14 | 4 | 16 | 14 | 7 | 9 | 7 | 9 | 13 | 10 |
| 没有粘合剂的对比例 | 5 | 12 | 7 | 8 | 11 | 11 | 4 | 5 | 7 | 10 | 8 |
可见，按照本发明实施例情况下，得到较高的平均水合作用。
Claims (13)
1.纤维和织物表面结构，其特征在于，该表面结构是用(a)微胶囊化的有效物质和(b)粘合剂组成的混合物涂敷的。
2.根据权利要求1的纤维和织物表面结构，其特征在于，该表面结构是用微胶囊化有效物质涂敷的，该有效物质选自生育酚、生育酚乙酸酯、生育酚棕榈酸酯、胡萝卜素、咖啡因、抗坏血酸、(脱氧)核糖核酸及其片段产物、β-葡聚糖、视黄醇、红没药醇、尿囊素、植烷三醇、泛酰醇、AHA-酸、氨基酸、神经酰胺、假神经酰胺、脱乙酰壳多糖、二羟基丙酮、醇、角鲨烷、精油、植物蛋白质及其水解产物和植物提取物及其混合物。
3.根据权利要求1和/或2的纤维和织物表面结构，其特征在于，微胶囊的有效物质含量为1-30重量％。
4.根据权利要求1-3中至少一项的纤维和织物表面结构，其特征在于，该表面结构是用平均直径为0.0001-5mm、由包膜和含有有效物质的基质组成的微胶囊涂敷的，该微胶囊由以下步骤得到：
(a1)由成胶剂、脱乙酰壳多糖和有效物质配制基质，
(a2)任选地将基质分散在油相中，
(a3)用阴离子聚合物水溶液处理任选分散的基质，并任选地除去油相。
或者
(b1)由成胶剂、阴离子聚合物和有效物质配制基质，
(b2)任选地将基质分散在油相中，
(b3)用脱乙酰壳多糖水溶液处理任选分散的基质，并任选除去油相。
或者
(c1)在乳化剂存在下，用油体将有效物质水制剂处理成水包油乳液，
(c2)用阴离子聚合物水溶液处理得到的乳液，
(c3)使得到的基质与脱乙酰壳多糖水溶液接触，和
(c4)从水相分离得到的胶囊产物。
5.根据权利要求1-4中至少一项的纤维和织物表面结构，其特征在于，该表面结构含有平均直径为0.0001-5mm的微胶囊。
6.根据权利要求1-5中至少一项的纤维和织物表面结构，其特征在于，该表面结构是用粘合剂涂敷的，该粘合剂选自蜜胺化合物聚合物、乙二醛化合物聚合物、硅酮化合物聚合物、氯甲代氧丙环交联的聚酰氨基胺类、聚亚烷基二醇、聚(甲基)丙烯酸酯和氟烃聚合物及其混合物。
7.根据权利要求1-6中至少一项的纤维和织物表面结构，其特征在于，该表面结构是用微胶囊和粘合剂组成的混合物涂敷的，两种组分的重量比为90∶10-10∶90。
8.涂敷纤维和织物表面结构的方法，其中，用含有微胶囊化的有效物质和粘合剂的水制剂浸渍基质。
9.涂敷纤维和织物表面结构的方法，其中，含有微胶囊化的有效物质和粘合剂的水制剂强行涂布。
10.根据权利要求8和/或9的方法，其特征在于，微胶囊化的有效物质和粘合剂能够是以水分散体的形式使用。
11.根据权利要求10的方法，其特征在于，水分散体的固体含量为5-90重量％。
12.根据权利要求10和/或11的方法，其特征在于，在使用中将水分散体稀释到1-60重量％的浓度。
13.一种含有(a)微胶囊化的有效物质和(b)粘合剂的混合物的用途，用于涂敷纤维和织物表面结构。
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-
2002
- 2002-04-30 EP EP02009718A patent/EP1359247B1/de not_active Expired - Lifetime
- 2002-04-30 AT AT02009718T patent/ATE306581T1/de active
- 2002-04-30 DK DK02009718T patent/DK1359247T3/da active
- 2002-04-30 ES ES02009718T patent/ES2249510T3/es not_active Expired - Lifetime
- 2002-04-30 DE DE50204522T patent/DE50204522D1/de not_active Expired - Lifetime
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2003
- 2003-04-22 CN CNB038097621A patent/CN1296552C/zh not_active Expired - Fee Related
- 2003-04-22 JP JP2004501701A patent/JP2005529246A/ja active Pending
- 2003-04-22 KR KR1020047017324A patent/KR101004591B1/ko not_active IP Right Cessation
- 2003-04-22 CA CA2483279A patent/CA2483279C/en not_active Expired - Fee Related
- 2003-04-22 US US10/512,742 patent/US7956025B2/en not_active Expired - Fee Related
- 2003-04-22 WO PCT/EP2003/004142 patent/WO2003093571A1/de active Application Filing
- 2003-04-22 BR BRPI0309628-9B1A patent/BR0309628B1/pt not_active IP Right Cessation
- 2003-04-22 MX MXPA04010582A patent/MXPA04010582A/es active IP Right Grant
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102822413A (zh) * | 2010-03-24 | 2012-12-12 | 利普泰股份公司 | 对多种纤维和/或纺织材料进行处理的方法 |
| CN102822413B (zh) * | 2010-03-24 | 2016-03-09 | 利普泰股份公司 | 对多种纤维和/或纺织材料进行处理的方法 |
| CN106592252A (zh) * | 2016-11-29 | 2017-04-26 | 佛山市南海区佳妍内衣有限公司 | 一种保健纤维面料及其制备方法 |
| CN107237132A (zh) * | 2017-06-04 | 2017-10-10 | 于世金 | 大豆分离蛋白环保浆料的制备方法及其应用 |
| CN108774789A (zh) * | 2018-08-02 | 2018-11-09 | 李萌 | 一种抗菌防敏功能性面料 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2483279A1 (en) | 2003-11-13 |
| CN1296552C (zh) | 2007-01-24 |
| EP1359247B1 (de) | 2005-10-12 |
| KR20040106404A (ko) | 2004-12-17 |
| US20050150056A1 (en) | 2005-07-14 |
| ES2249510T3 (es) | 2006-04-01 |
| KR101004591B1 (ko) | 2010-12-28 |
| CA2483279C (en) | 2011-06-14 |
| EP1359247A1 (de) | 2003-11-05 |
| US7956025B2 (en) | 2011-06-07 |
| BR0309628A (pt) | 2007-03-06 |
| ATE306581T1 (de) | 2005-10-15 |
| MXPA04010582A (es) | 2004-12-13 |
| BR0309628B1 (pt) | 2013-09-10 |
| WO2003093571A1 (de) | 2003-11-13 |
| DK1359247T3 (da) | 2006-02-13 |
| JP2005529246A (ja) | 2005-09-29 |
| HK1076496A1 (en) | 2006-01-20 |
| DE50204522D1 (de) | 2005-11-17 |
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