CN110382568B - 烯丙基封端的聚异丁烯的硼氢化/氧化 - Google Patents

烯丙基封端的聚异丁烯的硼氢化/氧化 Download PDF

Info

Publication number
CN110382568B
CN110382568B CN201880015307.5A CN201880015307A CN110382568B CN 110382568 B CN110382568 B CN 110382568B CN 201880015307 A CN201880015307 A CN 201880015307A CN 110382568 B CN110382568 B CN 110382568B
Authority
CN
China
Prior art keywords
polyisobutylene
acid
borohydride
diallylpolyisobutylene
alkali metal
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN201880015307.5A
Other languages
English (en)
Other versions
CN110382568A (zh
Inventor
约瑟夫·T·小德兰尼
安德鲁·J·罗
帕特里克·威洛比
尼拉杰·古隆
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cardiac Pacemakers Inc
Original Assignee
Cardiac Pacemakers Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cardiac Pacemakers Inc filed Critical Cardiac Pacemakers Inc
Publication of CN110382568A publication Critical patent/CN110382568A/zh
Application granted granted Critical
Publication of CN110382568B publication Critical patent/CN110382568B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/06—Oxidation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F110/00—Homopolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F110/04—Monomers containing three or four carbon atoms
    • C08F110/08—Butenes
    • C08F110/10—Isobutene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/02—Alkylation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/26—Removing halogen atoms or halogen-containing groups from the molecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/42—Introducing metal atoms or metal-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2810/00—Chemical modification of a polymer
    • C08F2810/30—Chemical modification of a polymer leading to the formation or introduction of aliphatic or alicyclic unsaturated groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2810/00—Chemical modification of a polymer
    • C08F2810/40—Chemical modification of a polymer taking place solely at one end or both ends of the polymer backbone, i.e. not in the side or lateral chains

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

一种由二烯丙基聚异丁烯制备聚异丁烯二醇的方法。所述方法包括：将二烯丙基聚异丁烯硼氢化以产生聚异丁烯二烷基硼烷，和将聚异丁烯二烷基硼烷氧化以形成聚异丁烯二醇。将二烯丙基聚异丁烯硼氢化通过将二烯丙基聚异丁烯与硼烷配位溶剂、硼氢化物的碱金属盐和酸原位结合来进行。在将酸与二烯丙基聚异丁烯结合之前将硼氢化物的碱金属盐与二烯丙基聚异丁烯结合。

Description

烯丙基封端的聚异丁烯的硼氢化/氧化
相关申请的交叉引用
本申请要求于2017年3月7日提交的临时申请No.62/468,316的优先权，其通过引用整体并入本文。
技术领域
本发明涉及制备聚异丁烯二醇的方法。更具体地，本发明涉及由二烯丙基聚异丁烯制备聚异丁烯二醇的方法。
背景技术
基于双官能遥爪软段的热塑性弹性体具有格外理想的特性。可用于这种热塑性弹性体中的双官能遥爪软段的实例包括基于聚异丁烯的软段。存在仅由聚异丁烯和聚异丁烯基材料提供的许多独特且理想的物理和机械特性，包括热稳定性、生物相容性和不透气性，等等。这些特性可以在共聚策略中用其它材料调节以及进一步改性，例如合成基于聚异丁烯(PIB)软段的聚氨酯。通过碳正离子聚合制备基于聚异丁烯的软段的方法采用双官能引发剂分子开始并产生聚异丁烯二醇。
用于所述制备聚异丁烯二醇的方法中的材料中的一些昂贵、有害且难以处理。需要更安全且更低成本的材料。
发明内容
实施例1是一种由二烯丙基聚异丁烯制备聚异丁烯二醇的方法。所述方法包括：将二烯丙基聚异丁烯硼氢化以产生聚异丁烯二烷基硼烷，和将聚异丁烯二烷基硼烷氧化以形成聚异丁烯二醇。将二烯丙基聚异丁烯硼氢化通过将二烯丙基聚异丁烯与硼烷配位溶剂、硼氢化物的碱金属盐和酸原位结合来进行。在将酸与二烯丙基聚异丁烯结合之前将硼氢化物的碱金属盐与二烯丙基聚异丁烯结合。
实施例2是如实施例1所述的方法，其中所述硼氢化物的碱金属盐包括硼氢化钠、硼氢化钾和硼氢化锂中的至少一种。
实施例3是如实施例1或2所述的方法，其中所述酸是强无机酸，所述强无机酸包括硫酸、氢氯酸、氢碘酸和氢溴酸中的至少一种。
实施例4是如实施例1或2所述的方法，其中所述酸包括强路易斯酸、卤化物或其组合；所述强路易斯酸包括三氯化硼、三氯化铝和三氟化铝中的至少一种；并且所述卤化物包括碘和溴中的至少一种。
实施例5是如实施例1-4中任一项所述的方法，其中所述硼烷配位溶剂包括四氢呋喃、二乙醚、二甲氧基乙烷、二甘醇二甲醚、三甘醇二甲醚和四甘醇二甲醚中的至少一种。
实施例6是如实施例1-5中任一项所述的方法，其中所述将聚异丁烯二烷基硼烷氧化以形成聚异丁烯二醇包括将碱和氧化剂与聚异丁烯二烷基硼烷结合。
实施例7是如实施例6所述的方法，其中所述氧化剂是过氧化氢、过乙酸、高锰酸钾和过氧化苯甲酰中的至少一种。
实施例8是如实施例6或7所述的方法，其中所述碱包括氢氧化钠和氢氧化钾中的至少一种。
实施例9是一种制备聚异丁烯二醇的方法，所述方法包括：提供聚异丁烯二氯化物，使聚异丁烯二氯化物与烯丙基三甲基硅烷反应以产生二烯丙基聚异丁烯，将二烯丙基聚异丁烯硼氢化以产生聚异丁烯二烷基硼烷，和将碱和氧化剂与聚异丁烯二烷基硼烷结合以形成聚异丁烯二醇。将二烯丙基聚异丁烯硼氢化通过将二烯丙基聚异丁烯与硼烷配位溶剂、硼氢化物的碱金属盐和酸原位结合来进行。在将酸与二烯丙基聚异丁烯结合之前将硼氢化物的碱金属盐与二烯丙基聚异丁烯结合。
实施例10是如实施例9所述的方法，其中所述硼氢化物的碱金属盐包括硼氢化钠、硼氢化钾和硼氢化锂中的至少一种。
实施例11是如实施例9或10所述的方法，其中所述酸是强无机酸，所述强无机酸包括硫酸、氢氯酸、氢碘酸和氢溴酸中的至少一种。
实施例12是如实施例9或10所述的方法，其中所述酸包括强路易斯酸、卤化物或其组合；所述强路易斯酸包括三氯化硼、三氯化铝和三氟化铝中的至少一种；并且所述卤化物包括碘和溴中的至少一种。
实施例13是如实施例9-12中任一项所述的方法，其中所述硼烷配位溶剂包括四氢呋喃、二乙醚、二甲氧基乙烷、二甘醇二甲醚、三甘醇二甲醚和四甘醇二甲醚中的至少一种。
实施例14是如实施例9-13中任一项所述的方法，其中所述氧化剂是过氧化氢、过乙酸、高锰酸钾和过氧化苯甲酰中的至少一种。
实施例15是如实施例9-14中任一项所述的方法，其中所述碱包括氢氧化钠和氢氧化钾中的至少一种。
实施例16是一种制备聚异丁烯二醇的方法，所述方法包括：提供二烯丙基聚异丁烯，将二烯丙基聚异丁烯硼氢化以产生聚异丁烯二烷基硼烷，和将聚异丁烯二烷基硼烷氧化以形成聚异丁烯二醇。将二烯丙基聚异丁烯硼氢化通过将二烯丙基聚异丁烯与硼烷配位溶剂、硼氢化物的碱金属盐和酸原位结合来进行。在将酸与二烯丙基聚异丁烯结合之前将硼氢化物的碱金属盐与二烯丙基聚异丁烯结合。
实施例17是如实施例16所述的方法，其中所述硼氢化物的碱金属盐包括硼氢化钠、硼氢化钾和硼氢化锂中的至少一种。
实施例18是如实施例16或17所述的方法，其中所述酸是强无机酸，所述强无机酸包括硫酸、氢氯酸、氢碘酸和氢溴酸中的至少一种。
实施例19是如实施例16或17所述的方法，其中所述酸包括强路易斯酸、卤化物或其组合；所述强路易斯酸包括三氯化硼、三氯化铝和三氟化铝中的至少一种；并且所述卤化物包括碘和溴中的至少一种。
实施例20是如实施例16-19中任一项所述的方法，其中所述硼烷配位溶剂包括四氢呋喃、二乙醚、二甲氧基乙烷、二甘醇二甲醚、三甘醇二甲醚和四甘醇二甲醚中的至少一种。
实施例21是如实施例16-20中任一项所述的方法，其中所述提供二烯丙基聚异丁烯包括：提供聚异丁烯二氯化物，和使聚异丁烯二氯化物与烯丙基三甲基硅烷反应以产生二烯丙基聚异丁烯。
实施例22是如实施例16所述的方法，其中所述将聚异丁烯二烷基硼烷氧化以形成聚异丁烯二醇包括将碱和氧化剂与聚异丁烯二烷基硼烷结合。
实施例23是如实施例22所述的方法，其中所述氧化剂是过氧化氢、过乙酸、高锰酸钾和过氧化苯甲酰中的至少一种。
实施例24是如实施例22或23所述的方法，其中所述碱包括氢氧化钠和氢氧化钾中的至少一种。
实施例25是一种制备聚异丁烯二醇的方法，所述方法包括：提供聚异丁烯二氯化物，使聚异丁烯二氯化物与烯丙基三甲基硅烷反应以产生二烯丙基聚异丁烯，将二烯丙基聚异丁烯硼氢化以产生聚异丁烯二烷基硼烷，和将碱和氧化剂与聚异丁烯二烷基硼烷结合以形成聚异丁烯二醇。将二烯丙基聚异丁烯硼氢化通过将二烯丙基聚异丁烯与硼烷配位溶剂、硼氢化物的碱金属盐和酸原位结合来进行。在将酸与二烯丙基聚异丁烯结合之前将硼氢化物的碱金属盐与二烯丙基聚异丁烯结合。
实施例26是如实施例25所述的方法，其中所述硼氢化物的碱金属盐包括硼氢化钠、硼氢化钾和硼氢化锂中的至少一种。
实施例27是如实施例25或26所述的方法，其中所述酸是强无机酸，所述强无机酸包括硫酸、氢氯酸、氢碘酸和氢溴酸中的至少一种。
实施例28是如实施例25或26所述的方法，其中所述酸包括强路易斯酸、卤化物或其组合；所述强路易斯酸包括三氯化硼、三氯化铝和三氟化铝中的至少一种；并且所述卤化物包括碘和溴中的至少一种。
实施例29是如实施例25-28中任一项所述的方法，其中所述硼烷配位溶剂包括四氢呋喃、二乙醚、二甲氧基乙烷、二甘醇二甲醚、三甘醇二甲醚和四甘醇二甲醚中的至少一种。
实施例30是如实施例25-29中任一项所述的方法，其中所述氧化剂是过氧化氢、过乙酸、高锰酸钾和过氧化苯甲酰中的至少一种。
实施例31是如实施例25-30中任一项所述的方法，其中所述碱包括氢氧化钠和氢氧化钾中的至少一种。
实施例32是一种制备聚异丁烯二醇的方法，所述方法包括：提供聚异丁烯二氯化物，使聚异丁烯二氯化物与烯丙基三甲基硅烷反应以产生二烯丙基聚异丁烯，将二烯丙基聚异丁烯硼氢化以产生聚异丁烯二烷基硼烷，和将过氧化氢以及氢氧化钠和氢氧化钾中的至少一种与聚异丁烯二烷基硼烷结合以形成聚异丁烯二醇。将二烯丙基聚异丁烯硼氢化通过将二烯丙基聚异丁烯与四氢呋喃、硼氢化物的碱金属盐和酸原位结合来进行。在将酸与二烯丙基聚异丁烯结合之前将硼氢化物的碱金属盐与二烯丙基聚异丁烯结合。
实施例33是如实施例32所述的方法，其中所述酸是强无机酸，所述强无机酸包括硫酸、氢氯酸、氢碘酸和氢溴酸中的至少一种。
实施例34是如实施例32所述的方法，其中所述酸包括强路易斯酸、卤化物或其组合；所述强路易斯酸包括三氯化硼、三氯化铝和三氟化铝中的至少一种；并且所述卤化物包括碘和溴中的至少一种。
实施例35是如实施例32-34中任一项所述的方法，其中所述硼氢化物的碱金属盐包括硼氢化钠、硼氢化钾和硼氢化锂中的至少一种。
尽管公开了多个实施方案，但是通过以下详细描述，本发明的其他实施方案对于本领域技术人员将变得明显，以下详细描述示出并描述了本发明的说明性实施方案。因此，附图和详细描述应被认为是说明性的而非限制性的。
附图说明
图1示出了根据本公开内容的实施方案的聚异丁烯二氯化物的形成。
图2示出了根据本公开内容的实施方案的由图1的聚异丁烯二氯化物形成二烯丙基聚异丁烯。
图3示出了根据本公开内容的实施方案的由图2的二烯丙基聚异丁烯形成聚异丁烯二烷基硼烷。
图4示出了根据本公开内容的实施方案的由图3的聚异丁烯二烷基硼烷形成聚异丁烯二醇。
尽管本发明可以进行各种修改和替换形式，但是在附图中通过实例的方式示出了具体实施方案，并且在下面详细描述。然而，其目的不是将本发明限制于所描述的具体实施方案。相反，本发明旨在覆盖落入由所附权利要求限定的本发明的范围内的所有修改方案、等同方案和替代方案。
具体实施方式
在本公开内容的实施方案中，制备聚异丁烯二醇可能需要将二烯丙基聚异丁烯硼氢化然后进行氧化步骤。本领域中通常用于提供用于硼氢化的硼烷的试剂是9-硼双环(3.3.1)壬烷(9-BBN)。然而，9-BBN是难以处理和储存的昂贵材料。另外，9-BBN是可燃的。
本公开内容的实施方案可以使用在硼烷配位溶剂中与酸结合的硼氢化物的碱金属盐以提供用于硼氢化的硼烷源。在本公开内容的实施方案中，将硼氢化物的碱金属盐和酸与二烯丙基聚异丁烯原位结合并彼此独立地添加至二烯丙基聚异丁烯。即，硼氢化物的碱金属盐和酸在添加至二烯丙基聚异丁烯之前不相互结合。以此方式，硼烷仅在含有二烯丙基聚异丁烯的反应容器中形成，这使得硼烷在其与二烯丙基聚异丁烯反应之前向水分的暴露最小化。这是有益的，因为硼烷易于与水分反应形成硼酸，最终必须以额外的成本将硼酸从聚异丁烯二醇中除去。此外，任何与水分反应的硼烷都不能用于硼氢化，因此需要额外的材料来生成硼烷并与二烯丙基聚异丁烯反应，这增加了硼氢化的成本。
与9-BBN相反，一些硼氢化物的碱金属盐，如硼氢化钠，是不可燃的并且更容易储存。硼氢化钠用于硼氢化可以导致比使用9-BBN节省约95％的成本。
图1-4示出了根据本公开内容的实施方案的聚异丁烯二醇的生产。如图1所示，异丁烯可以与双官能阳离子引发剂化合物如受阻二枯基醚和甲基氯化物在四氯化钛的存在下反应，以使异丁烯聚合并产生聚异丁烯二氯化物。应理解，这仅是生产聚异丁烯二氯化物的一种方法，并且可以使用其它方法。
一旦产生聚异丁烯二氯化物，烯丙基端基可被加到聚异丁烯链上。在图2所示的实施方案中，将烯丙基三甲基硅烷添加至聚异丁烯二氯化物。然后，聚异丁烯二氯化物可以与烯丙基三甲基硅烷反应以产生二烯丙基聚异丁烯，如图2所示。二烯丙基聚异丁烯的烯丙基端基导致近定量取代，引起高度遥爪聚合物的产生。高度遥爪聚合物允许具有有益特性的较高分子量聚合物链。
一旦产生二烯丙基聚异丁烯，就将硼氢化物的碱金属盐和硼烷配位溶剂原位添加至二烯丙基聚异丁烯。在一些实施方案中，在添加硼烷配位溶剂之后添加硼氢化物的碱金属盐。在其它实施方案中，在添加硼氢化物的碱金属盐之后添加硼烷配位溶剂。在添加硼氢化物的碱金属盐和硼烷配位溶剂之后，将酸原位添加至二烯丙基聚异丁烯。如上所述，硼氢化物的碱金属盐和酸在添加至二烯丙基聚异丁烯之前不进行结合。
在一些实施方案中，所述硼氢化物的碱金属盐可包括硼氢化钠、硼氢化钾和/或硼氢化锂。在一些实施方案中，所述酸可包括强无机酸，如硫酸、氢氯酸、氢碘酸、氢溴酸或其混合物。在一些实施方案中，所述酸可包括元素卤化物，如碘、溴或其混合物。在一些实施方案中，所述酸可包括强路易斯酸，如三氯化硼、三氯化铝、三氟化铝或其混合物。在一些实施方案中，所述硼烷配位溶剂可包括四氢呋喃(THF)、二乙醚、二甲氧基乙烷、二甘醇二甲醚、三甘醇二甲醚、四甘醇二甲醚或其混合物。
在一些实施方案中，硼烷配位溶剂与硼氢化物的碱金属盐的摩尔比为至少1:1，以使硼烷配位并稳定，从而防止副反应。在一些实施方案中，硼烷配位溶剂与硼氢化物的碱金属盐的摩尔比低至1.1:1、1.2:1、1.3:1、1.4:1或1.5:1，或高至1.6:1、1.7:1、1.8:1、1.9:1或2:1，或在限定于任何两个前述值之间的任何值之间，例如1.1:1至2:1、1.2:1至1.9:1、1.3:1至1.8:1、1.4:1至1.7:1或1.5:1至1.6:1。
在硼烷配位溶剂的存在下将硼氢化物的碱金属盐和酸结合可以产生硼烷络合物。例如，在一些实施方案中，将硼氢化钠(NaBH4)和无机酸如硫酸(H2SO4)与THF原位结合以产生硼烷络合物，如下面反应式1所示：
反应式1 2NaBH4+H2SO4+2THF→2BH3:THF+Na2SO4+H2
产生的氢气(H2)可以用惰性气体如氮气稀释并安全地排出。硫酸钠(Na2SO4)可通过随后的水洗除去。
在一些其它实施方案中，将硼氢化钠和路易斯酸如三氯化硼(BCl3)与THF原位结合以产生硼烷络合物，如下面反应式2所示：
反应式2 3NaBH4+BCl3+4THF→4BH3:THF+3NaCl
如图3所示，硼烷络合物可以与二烯丙基聚异丁烯原位反应以产生聚异丁烯二烷基硼烷。已经发现硼烷络合物的反应性足以将二烯丙基聚异丁烯的烯丙基端基硼氢化。这是令人惊讶的，因为烯丙基端基R-CH2-CH＝CH2比其它亚乙烯基端基(如R–C(CH3)＝CH2或R–CH＝CH2，其中R是聚异丁烯链)的活性低。
然后可以将聚异丁烯二烷基硼烷氧化以形成聚异丁烯二醇。在一些实施方案中，可以通过加入氧化剂例如过氧化氢、过乙酸、高锰酸钾或过氧化苯甲酰来氧化聚异丁烯二烷基硼烷。图4示出了由聚异丁烯二烷基硼烷通过用过氧化氢氧化形成聚异丁烯二醇。在一些实施方案中，所述氧化在通过添加碱(例如氢氧化钠或氢氧化钾)所产生的碱性环境中进行。
在不脱离本发明的范围的情况下，可以对所讨论的示例性实施方案进行各种修改和添加。例如，尽管上述实施方案涉及特定特征，但本发明的范围还包括具有不同特征组合的实施方案和不包括所有所述特征的实施方案。因此，本发明的范围旨在包含落入权利要求范围内的所有这种替代方案、修改方案和变化方案，以及其所有等同方案。
实施例
聚异丁烯(PIB)二醇的合成
将受阻二枯基醚与无水己烷和2,6-二叔丁基吡啶在反应器中结合。通过冷却至-80℃的冷却盘管将甲基氯化物(MeCl)和异丁烯添加至反应器。将溶液搅拌并通过反应器中的液氮冷却套或盘管保持在-80℃。通过向反应器添加四氯化钛引发聚合，以形成聚异丁烯二氯化物(图1)。30分钟后，向反应器添加烯丙基三甲基硅烷，以在封端反应中向聚合物链末端引入烯丙基(图2)。2小时后，通过在-80℃下添加甲醇(MeOH)来终止反应。将所得溶液在25℃下搅拌过夜，直到MeCl完全蒸发。用氯化钠水溶液洗涤所得聚合物。排出反应器中来自底层的含水废物，然后进行多次去离子水洗涤，直到水层的pH为中性。最终洗涤后，向反应器添加大量的MeOH以使聚合物沉淀。将所得聚合物转移至蒸馏烧瓶，与甲苯混合，并通过干甲苯的共沸蒸馏进行干燥，以制备二烯丙基聚异丁烯(遥爪烯丙基封端的聚异丁烯)。
在装有磁力搅拌器、干燥氮气层、冰浴、橡胶隔片和数字热电偶的2000mL三颈圆底烧瓶中，将10.66g二烯丙基聚异丁烯(0.005摩尔，分子量为2000Da)溶解在605mL无水THF中。将0.605g(0.016摩尔)硼氢化钠添加至烧瓶中的二烯丙基聚异丁烯，并借助于搅拌使其溶解。在所得溶液在0℃平衡后，使用注射器将0.8523g(0.016摩尔)浓硫酸的等分试样逐滴添加至烧瓶中的溶液，导致氢气的逸出和聚异丁烯二烷基硼烷的形成(图3)。将溶液升至室温，然后用16mL 3N NaOH水溶液(0.016摩尔)猝灭。然后用1.81mL 30％H2O2(0.016摩尔)处理包括聚异丁烯二烷基硼烷的猝灭溶液，并使其反应12小时以形成聚异丁烯二醇(图4)。然后用500mL己烷和50mL包括3.326g亚硫酸氢钠(0.031摩尔)的溶液萃取所述溶液以猝灭任何未反应的过氧化物。将混合物转移至分液漏斗，并除去水层。将己烷溶液用去离子水洗涤三次。然后采用旋转蒸发将有机溶液提出，产生透明粘性油。
透明粘性油的质子核磁共振光谱证实了1-羟丙基封端的端基的存在，从而证实了聚异丁烯二醇的合成。

Claims (11)

1.一种由二烯丙基聚异丁烯制备聚异丁烯二醇的方法，所述方法包含：
通过将二烯丙基聚异丁烯与硼烷配位溶剂、硼氢化物的碱金属盐和酸原位结合而将二烯丙基聚异丁烯硼氢化以产生聚异丁烯二烷基硼烷，其中在将酸与二烯丙基聚异丁烯结合之前将硼氢化物的碱金属盐与二烯丙基聚异丁烯结合；和
将聚异丁烯二烷基硼烷氧化以形成聚异丁烯二醇；
其中所述酸是强无机酸，所述强无机酸包括硫酸、氢氯酸、氢碘酸和氢溴酸中的至少一种。
2.如权利要求1所述的方法，其中所述硼氢化物的碱金属盐包括硼氢化钠、硼氢化钾和硼氢化锂中的至少一种。
3.如权利要求1或2所述的方法，其中所述硼烷配位溶剂包括四氢呋喃、二乙醚、二甲氧基乙烷、二甘醇二甲醚、三甘醇二甲醚和四甘醇二甲醚中的至少一种。
4.如权利要求1或2所述的方法，其中所述将聚异丁烯二烷基硼烷氧化以形成聚异丁烯二醇包括将碱和氧化剂与聚异丁烯二烷基硼烷结合。
5.如权利要求4所述的方法，其中所述氧化剂是过氧化氢、过乙酸、高锰酸钾和过氧化苯甲酰中的至少一种。
6.如权利要求4所述的方法，其中所述碱包括氢氧化钠和氢氧化钾中的至少一种。
7.一种制备聚异丁烯二醇的方法，所述方法包含：
提供聚异丁烯二氯化物；
使聚异丁烯二氯化物与烯丙基三甲基硅烷反应以产生二烯丙基聚异丁烯；
通过将二烯丙基聚异丁烯与硼烷配位溶剂、硼氢化物的碱金属盐和酸原位结合而将二烯丙基聚异丁烯硼氢化以产生聚异丁烯二烷基硼烷，其中在将酸与二烯丙基聚异丁烯结合之前将硼氢化物的碱金属盐与二烯丙基聚异丁烯结合；和
将碱和氧化剂与聚异丁烯二烷基硼烷结合以形成聚异丁烯二醇；
其中所述酸是强无机酸，所述强无机酸包括硫酸、氢氯酸、氢碘酸和氢溴酸中的至少一种。
8.如权利要求7所述的方法，其中所述硼氢化物的碱金属盐包括硼氢化钠、硼氢化钾和硼氢化锂中的至少一种。
9.如权利要求7或8所述的方法，其中所述硼烷配位溶剂包括四氢呋喃、二乙醚、二甲氧基乙烷、二甘醇二甲醚、三甘醇二甲醚和四甘醇二甲醚中的至少一种。
10.如权利要求7或8所述的方法，其中所述氧化剂是过氧化氢、过乙酸、高锰酸钾和过氧化苯甲酰中的至少一种。
11.如权利要求7或8所述的方法，其中所述碱包括氢氧化钠和氢氧化钾中的至少一种。
CN201880015307.5A 2017-03-07 2018-03-07 烯丙基封端的聚异丁烯的硼氢化/氧化 Active CN110382568B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201762468316P 2017-03-07 2017-03-07
US62/468,316 2017-03-07
PCT/US2018/021311 WO2018165273A1 (en) 2017-03-07 2018-03-07 Hydroboration/oxidation of allyl-terminated polyisobutylene

Publications (2)

Publication Number Publication Date
CN110382568A CN110382568A (zh) 2019-10-25
CN110382568B true CN110382568B (zh) 2022-03-04

Family

ID=61692139

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201880015307.5A Active CN110382568B (zh) 2017-03-07 2018-03-07 烯丙基封端的聚异丁烯的硼氢化/氧化

Country Status (4)

Country Link
US (1) US10526429B2 (zh)
EP (1) EP3592786B1 (zh)
CN (1) CN110382568B (zh)
WO (1) WO2018165273A1 (zh)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2385960B1 (en) 2009-01-12 2020-03-11 University Of Massachusetts Lowell Polyisobutylene-based polyurethanes
EP2922888B1 (en) 2012-11-21 2021-08-18 The University of Massachusetts High strength polyisobutylene polyurethanes
EP3668912B1 (en) 2017-08-17 2021-06-30 Cardiac Pacemakers, Inc. Photocrosslinked polymers for enhanced durability
CN111479596B (zh) 2018-01-17 2023-04-07 心脏起搏器股份公司 封端聚异丁烯聚氨酯

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1745111A (zh) * 2003-01-28 2006-03-08 巴斯福股份公司 利用硼氢化进行的异丁烯聚合物官能化
US20060135721A1 (en) * 2003-06-26 2006-06-22 Arno Lange Method for producing polyisobutenes
US20160008607A1 (en) * 2014-07-11 2016-01-14 Cardiac Pacemakers, Inc. Polymeric feed-thru for chronic implantable devices

Family Cites Families (316)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2240558A (en) 1936-02-07 1941-05-06 Standard Oil Dev Co Nitrated diesel fuel and process of making same
US2182513A (en) 1936-05-14 1939-12-05 Standard Oil Co Method of sealing waxy surfaces
US2202877A (en) 1937-04-12 1940-06-04 Gulf Oil Corp Antioxidants and petroleum oils containing the same
US2451420A (en) 1943-07-28 1948-10-12 Du Pont Artificial yarns and process of producing the same
US2463452A (en) 1943-08-07 1949-03-01 Du Pont Adhesive compositions and adhesive sheets
US3069236A (en) 1955-03-10 1962-12-18 Aerojet General Co Method for the preparation of diborane
US3148028A (en) 1955-06-24 1964-09-08 Aerojet General Co Method for the preparation of diborane
NL295726A (zh) 1962-07-25
US3328372A (en) 1964-05-11 1967-06-27 Exxon Research Engineering Co Soluble high molecular weight polymers of cyclopentadiene
NL6606553A (zh) 1965-06-18 1967-11-13
BE759829A (fr) 1969-12-03 1971-06-03 Upjohn Co Preparation de polyurethanes
US3966624A (en) 1971-07-15 1976-06-29 Sun Oil Company Of Pennsylvania Blended traction fluid containing hydrogenated polyolefin and an adamantane ether
US3815611A (en) 1971-11-26 1974-06-11 Medtronic Inc Muscle stimulation and/or contraction detection device
US3755265A (en) 1972-04-04 1973-08-28 Nasa Highly fluorinated polyurethanes
US4118427A (en) 1973-02-13 1978-10-03 California Institute Of Technology Curable liquid hydrocarbon prepolymers containing hydroxyl groups and process for producing same
GB1527592A (en) 1974-08-05 1978-10-04 Ici Ltd Wound dressing
US4154913A (en) 1975-05-05 1979-05-15 The Firestone Tire & Rubber Company Amine terminated polymers and the formation of blocked copolymers
US4157429A (en) 1975-05-05 1979-06-05 The Firestone Tire & Rubber Company Amine terminated polymers and the formation of block copolymers
US4157430A (en) 1975-05-05 1979-06-05 The Firestone Tire & Rubber Company Amine terminated polymers and the formation of block copolymers
GB1542319A (en) 1975-11-26 1979-03-14 Exxon Research Engineering Co Halogenated organoaluminium catalyst compositions and method of their preparation
US4352359A (en) 1977-08-19 1982-10-05 Minnesota Mining And Manufacturing Company Biomedical electrode
US4230509A (en) 1979-04-13 1980-10-28 The United States Of America As Represented By The Secretary Of The Army Pyrophoric flame composition
US4304771A (en) 1979-07-13 1981-12-08 Usv Pharmaceutical Corporation Antihypertensive amides
US4342849A (en) 1979-09-10 1982-08-03 The University Of Akron Novel telechelic polymers and processes for the preparation thereof
US4316973A (en) 1979-09-10 1982-02-23 The University Of Akron Novel telechelic polymers and processes for the preparation thereof
US4276394A (en) 1979-09-10 1981-06-30 The University Of Akron Novel telechelic polymers, block copolymers and processes for the preparation thereof
US4539996A (en) 1980-01-23 1985-09-10 Minnesota Mining And Manufacturing Company Conductive adhesive and biomedical electrode
US4686137A (en) 1980-02-29 1987-08-11 Thoratec Laboratories Corp. Moisture vapor permeable materials
US5120813A (en) 1980-02-29 1992-06-09 Th. Goldschmidt Ag Moisture vapor permeable materials
US4861830A (en) 1980-02-29 1989-08-29 Th. Goldschmidt Ag Polymer systems suitable for blood-contacting surfaces of a biomedical device, and methods for forming
US4675361A (en) 1980-02-29 1987-06-23 Thoratec Laboratories Corp. Polymer systems suitable for blood-contacting surfaces of a biomedical device, and methods for forming
US4423185A (en) 1980-03-03 1983-12-27 Asahi Kasei Kogyo Kabushiki Kaisha Thermoplastic resinous composition
US4374276A (en) 1981-08-27 1983-02-15 International Flavors & Fragrances Inc. Novel branched chain ketones and the process for preparing same
US4430233A (en) 1981-08-27 1984-02-07 International Flavors & Fragrances Inc. Branched chain ketones and uses thereof in augmenting or enhancing the aroma of perfumes, colognes and perfumed articles and the process for preparing same
US4425264A (en) 1981-08-27 1984-01-10 International Flavors & Fragrances Inc. Branched chain ketones used in augmenting or enhancing the aroma of perfumes, colognes and perfumed articles and the like process for preparing same
IL64952A (en) 1982-02-08 1984-12-31 Bromine Compounds Ltd Intumescent fire retardant polymer compositions
US4484586A (en) 1982-05-27 1984-11-27 Berkley & Company, Inc. Hollow conductive medical tubing
US4420411A (en) 1982-06-04 1983-12-13 International Flavors & Fragrances Inc. Process for augmenting or enhancing the aroma of detergents using unsaturated branch chain ketones
US4477604A (en) 1982-09-20 1984-10-16 Oechsle Iii Sixtus J Polyurethane compositions and their use as luting agents
US4570270A (en) 1982-09-20 1986-02-18 Oechsle Iii Sixtus J Polyurethane compositions and their use as luting agents
US4486572A (en) 1983-07-06 1984-12-04 University Of Akron Synthesis of amphiphilic block copolymers and networks
US4518615A (en) 1983-08-23 1985-05-21 Warner-Lambert Company Non-adhesive chewing gum base composition
ZA841613B (en) 1984-03-02 1984-04-29 Thiokol Corporation Radiation curable coating for photographic laminate
US4767885A (en) 1984-08-06 1988-08-30 University Of Akron Sterically hindered binifers telechelic polymers made therefrom
US4888389A (en) 1985-02-05 1989-12-19 University Of Akron Amphiphilic polymers and method of making said polymers
US4982038A (en) 1985-03-19 1991-01-01 Phillips Petroleum Company Oxidative methylation of organic compounds
US4910321A (en) 1985-06-20 1990-03-20 University Of Akron Living catalysts, complexes and polymers therefrom
US4771082A (en) 1986-01-30 1988-09-13 Solodovnik Valentin D Polyurethane foam composition for immobilization in traumatology
US5330520A (en) 1986-05-15 1994-07-19 Telectronics Pacing Systems, Inc. Implantable electrode and sensor lead apparatus
JPS6345821A (ja) 1986-08-13 1988-02-26 Hitachi Tokyo Electron Co Ltd 蒸気処理装置
US4880883A (en) 1987-06-03 1989-11-14 Wisconsin Alumni Research Foundation Biocompatible polyurethanes modified with lower alkyl sulfonate and lower alkyl carboxylate
US5017664A (en) 1987-06-03 1991-05-21 Wisconsin Alumni Research Foundation Biocompatible polyurethane devices wherein polyurethane is modified with lower alkyl sulfonate and lower alkyl carboxylate
DE3878048T2 (de) 1987-06-18 1993-05-19 Dai Ichi Kogyo Seiyaku Co Ltd Polyurethanzusammensetzung.
US4752626A (en) 1987-08-27 1988-06-21 General Motors Corporation Method of making low compression set urethane foams
US5000875A (en) 1987-10-16 1991-03-19 E. I. Du Pont De Nemours And Company Conductive filled fluoropolymers
US5149739A (en) 1988-08-01 1992-09-22 The Bfgoodrich Company Fiber-reinforced thermoplastic elastomer polyurethane compositions with either modified and/or unmodified polyolefins
US5171760A (en) 1988-08-05 1992-12-15 Edison Polymer Innovation Corp. UV curable polymer formulation
DE68912018T2 (de) 1988-08-05 1994-04-28 Edison Polymer Innovation UV-härtbare Polymerzusammensetzung.
IT1227065B (it) 1988-09-15 1991-03-14 Ausimont Spa Poliuretani fluorurati, contenenti blocchi gommosi a struttura polios siperfluoroalchilenica blocchi rigidi idrogenati, aventi migliorate proprieta' meccaniche.
US4939184A (en) 1989-03-07 1990-07-03 University Of Akron Polyurethane foam
EP0388480A1 (de) 1989-03-20 1990-09-26 Siemens Aktiengesellschaft Implantierbare Reizelektrode
US5433730A (en) 1989-05-03 1995-07-18 Intermedics, Inc. Conductive pouch electrode for defibrillation
US4928689A (en) 1989-05-15 1990-05-29 Cardiac Pacemakers, Inc. Rate adaptive cardiac pacer system having living cell tissue for sensing physiologic demand
US5029585A (en) 1989-07-14 1991-07-09 Baxter International Inc. Comformable intralumen electrodes
US5194505A (en) 1989-09-29 1993-03-16 E. I. Du Pont De Nemours And Company Chlorosulfonated polyolefin-modified polyurethane and polyurea compositions and process for making same
US5090422A (en) 1990-04-19 1992-02-25 Cardiac Pacemakers, Inc. Implantable electrode pouch
US5282844A (en) 1990-06-15 1994-02-01 Medtronic, Inc. High impedance, low polarization, low threshold miniature steriod eluting pacing lead electrodes
BR9003841A (pt) 1990-08-06 1992-02-25 Sika S A Resina de poliuretana,adesivo,resina epoxi,processo para producao das ditas resinas,tinta e uso
ES2097169T3 (es) 1990-08-16 1997-04-01 Basf Ag Procedimiento para la obtencion de hidrocarburos y polimeros con grupos cloruro terminales alilicos.
JP2969470B2 (ja) 1990-10-18 1999-11-02 鐘淵化学工業株式会社 末端にアリル基を有するイソブチレン系重合体およびその製造方法
US5129404A (en) 1990-12-21 1992-07-14 Intermedics, Inc. Implantable endocardial lead with retractable fixation apparatus
US5152299A (en) 1991-04-19 1992-10-06 Intermedics, Inc. Implantable endocardial lead with spring-loaded screw-in fixation apparatus
IT1252660B (it) 1991-12-23 1995-06-20 Ausimont Spa Poliuretani e poliuretani-uree fluorurati e processi per la loro preparazione
CA2129730C (en) 1992-02-10 1998-07-14 Albert I. Everaerts Radiation crosslinked elastomers
US6010715A (en) 1992-04-01 2000-01-04 Bertek, Inc. Transdermal patch incorporating a polymer film incorporated with an active agent
CA2134087C (en) 1992-04-24 2007-07-17 Robert S. Ward Copolymers and non-porous, semi-permeable membrane thereof and its use for permeating molecules of predetermined molecular weight range
US5589563A (en) 1992-04-24 1996-12-31 The Polymer Technology Group Surface-modifying endgroups for biomedical polymers
US5269810A (en) 1992-06-19 1993-12-14 W. L. Gore & Associates, Inc. Patch electrode
US5324324A (en) 1992-10-13 1994-06-28 Siemens Pacesetter, Inc. Coated implantable stimulation electrode and lead
US5322520A (en) 1992-11-12 1994-06-21 Implemed, Inc. Iontophoretic structure for medical devices
US5340881A (en) 1992-11-16 1994-08-23 The University Of Akron Aldehyde-telechelic polyisobutylenes, catalytic method for preparing the same with high conversion and selectivity, and block copolymers made thereform
JPH08505539A (ja) 1993-02-01 1996-06-18 ダブリュ．エル．ゴア アンド アソシエーツ，インコーポレイティド インプラント用電極
DE4303556C1 (de) 1993-02-08 1994-10-27 Bayer Ag Harte Polyurethane oder Polyurethanschaumstoffe
EP0612538A3 (en) 1993-02-22 1995-04-05 Cardiac Pacemakers Inc Metallized heart electrode.
US5385579A (en) 1993-03-30 1995-01-31 Siemens Pacesetter, Inc. Myocardial body implantable lead
GB9306887D0 (en) 1993-04-01 1993-05-26 Graham Neil B Random block copolymers
US5476496A (en) 1993-06-01 1995-12-19 Pacesetter Ab Implantable medical electrode system having an indifferent electrode formed as a part of the electrode insulator sleeve
WO1995010544A1 (en) 1993-10-15 1995-04-20 University Of Massachusetts At Lowell Capping of living polymers
CA2174246C (en) 1993-10-29 2004-05-11 Gary R. Schildgen Method of manufacturing a medical electrical lead
FR2713989B1 (fr) 1993-12-21 1996-01-12 Nipson Imprimante à haute cadence d'impression et utilisations d'une telle imprimante.
JPH07331223A (ja) 1994-06-06 1995-12-19 Kanegafuchi Chem Ind Co Ltd 医療用粘着組成物
JPH07330591A (ja) 1994-06-06 1995-12-19 Kanegafuchi Chem Ind Co Ltd 経皮吸収製剤
BE1008706A3 (fr) 1994-09-28 1996-07-02 Cockerill Rech & Dev Produit pour la formation d'un revetement sur un support et procede de preparation de ce produit.
US5442010A (en) 1994-10-04 1995-08-15 Dow Corning Corporation Epoxy-terminated polyisobutylene-polydimethylsiloxane compositions
US5691062A (en) 1995-02-16 1997-11-25 Clemson University Molecularly bonded inherently conductive polymers on substrates and shaped articles thereof
CA2168938C (en) 1995-03-13 2010-06-01 Wolfgang Kaufhold A thermoplastic polyurethane resin
US5559067A (en) 1995-03-31 1996-09-24 Engelhard Corporation Modified microsphere FCC catalysts and manufacture thereof
GB9507393D0 (en) * 1995-04-10 1995-05-31 Bp Chem Int Ltd Polyolefin diols
US5837313A (en) 1995-04-19 1998-11-17 Schneider (Usa) Inc Drug release stent coating process
US5639847A (en) 1995-05-25 1997-06-17 Mearthane Products Corp. Preparation of conductive polyurethanes using a conductive quasi-solution
US5630844A (en) 1995-06-07 1997-05-20 Novamed Medical Products Manufacturing, Inc. Biocompatible hydrophobic laminate with thermoplastic elastomer layer
US5681514A (en) 1995-06-07 1997-10-28 Sulzer Intermedics Inc. Method for making an implantable conductive lead for use with a cardiac stimulator
US5663234A (en) 1995-06-15 1997-09-02 The University Of Akron Cationic multiblock thermoplastic elastomers
GB9513713D0 (en) 1995-07-05 1995-09-06 Exxon Chemical Patents Inc Curable elastomeric compositions and a process to produce curable elastomeric compositions
US6369123B1 (en) 1995-08-14 2002-04-09 3M Innovative Properties Company Radiation-crosslinkable elastomers and photocrosslinkers therefor
US5987746A (en) 1996-02-21 1999-11-23 Medtronic, Inc. Method of making medical electrical lead
DE19610350A1 (de) 1996-03-15 1997-09-18 Basf Ag Initiatoren für die anionisch initiierte Polymerisation von wenigstens eine ethylenisch ungesättigte Gruppe aufweisenden Monomeren
US5912302A (en) 1996-06-11 1999-06-15 Gadkari; Avinash Chandrakant Elastomeric compositions and a process to produce elastomeric compositions
US5755762A (en) 1996-06-14 1998-05-26 Pacesetter, Inc. Medical lead and method of making and using
US5741331A (en) 1996-07-29 1998-04-21 Corvita Corporation Biostable elastomeric polymers having quaternary carbons
US5665823A (en) 1996-08-30 1997-09-09 Dow Corning Corporation Polyisobutylene polymers having acrylic functionality
US6200589B1 (en) 1996-09-13 2001-03-13 The University Of Akron Biological implants of semipermeable amphiphilic membranes
AUPO251096A0 (en) 1996-09-23 1996-10-17 Cardiac Crc Nominees Pty Limited Polysiloxane-containing polyurethane elastomeric compositions
EP0837097B1 (en) 1996-10-15 1999-08-11 Advanced Elastomer Systems, L.P. New block copolymers of polyolefins with polyurethanes, copolyesters or copolyamides and their use
US5874484A (en) 1997-01-30 1999-02-23 Shell Oil Company Use of polyol mixtures in rigid and semi-rigid polyurethane foams
EP0961796B1 (en) 1997-01-30 2002-05-02 KRATON Polymers Research B.V. Use of polyol mixtures in rigid and semi-rigid polyurethane foams
WO1998033832A1 (en) 1997-01-30 1998-08-06 Shell Internationale Research Maatschappij B.V. Use of polyol mixtures in rigid and semi-rigid polyurethane foams
US5796044A (en) 1997-02-10 1998-08-18 Medtronic, Inc. Coiled wire conductor insulation for biomedical lead
US6117554A (en) 1997-05-30 2000-09-12 Poly-Med, Inc. Modulated molecularly bonded inherently conductive polymers on substrates with conjugated multiple lamellae and shaped articles thereof
US5886089A (en) 1997-06-04 1999-03-23 Gfx Technologies, Inc. Grip and friction enhancement compositions
US6005051A (en) 1997-08-06 1999-12-21 The University Of Akron Multi-component polymeric networks containing polyisobutylene
US6072003A (en) 1997-08-25 2000-06-06 Advanced Elastomer Systems, L.P. Block copolymers of polyolefins with polyurethanes, copolyesters or copolyamides and their use
US20020012694A1 (en) 1997-09-17 2002-01-31 Alfred J. Moo-Young Transdermal administration of ment
JP3671624B2 (ja) 1997-10-27 2005-07-13 株式会社カネカ ポリウレタン系弾性繊維
SE510868C2 (sv) 1997-11-03 1999-07-05 Artimplant Dev Artdev Ab Formkroppar för användning som implantat i humanmedicin samt förfarande för framställning av sådana formkroppar
US5991667A (en) 1997-11-10 1999-11-23 Vitatron Medical, B.V. Pacing lead with porous electrode for stable low threshold high impedance pacing
US5902329A (en) 1997-11-14 1999-05-11 Pacesetter, Inc. Explantable lead
EP0916394B1 (en) 1997-11-14 2004-03-10 Sharp Kabushiki Kaisha Method of manufacturing modified particles and manufacturing device therefor
US6093197A (en) 1997-12-08 2000-07-25 Axon Engineering, Inc. Spiral nerve cuff electrode implantation tool
US5861023A (en) 1997-12-16 1999-01-19 Pacesetter, Inc. Thrombus and tissue ingrowth inhibiting overlays for defibrillator shocking coil electrodes
US5931862A (en) 1997-12-22 1999-08-03 Pacesetter, Inc. Medical lead and method of making and using with sodium sulfosuccinic ester
DE19800697B4 (de) 1998-01-10 2009-04-02 Biotronik Gmbh & Co. Kg Einzel-Elektrodensonde, insbesondere für implantierbare Defibrillatoren
KR100583215B1 (ko) 1998-03-31 2006-05-24 세끼스이 가가쿠 고교 가부시키가이샤 폴리에스테르우레탄 엘라스토머 및 이의 제조방법
US6256541B1 (en) 1998-04-17 2001-07-03 Cardiac Pacemakers, Inc. Endocardial lead having defibrillation and sensing electrodes with septal anchoring
US20020138123A1 (en) 1998-04-21 2002-09-26 Medtronic, Inc. Medical electrical leads and indwelling catheters with enhanced biocompatibility and biostability
CN1279395C (zh) 1998-08-26 2006-10-11 日产化学工业株式会社 液晶取向处理剂和用该处理剂的液晶元件以及液晶的取向方法
CN1075103C (zh) 1998-09-21 2001-11-21 深圳市奥博胶粘剂化工有限公司 一种聚氨酯粘接剂/密封胶组合物及其制备方法
US6361780B1 (en) 1998-11-12 2002-03-26 Cardiac Pacemakers, Inc. Microporous drug delivery system
JP4057174B2 (ja) 1998-12-08 2008-03-05 株式会社カネカ 粘着剤組成物および粘着製品の製造方法
EP1171496B1 (en) 1999-03-23 2005-12-07 Carnegie-Mellon University Catalytic processes for the controlled polymerization of free radically (co)polymerizable monomers and functional polymeric systems prepared thereby
US6253110B1 (en) 1999-04-27 2001-06-26 Medtronic Inc Method for tissue stimulation and fabrication of low polarization implantable stimulation electrode
US6869466B2 (en) 1999-05-07 2005-03-22 Unisearch Limited Cucurbiturils and method for binding gases and volatiles using cucurbiturils
EP1061092A1 (en) 1999-06-17 2000-12-20 Shell Internationale Researchmaatschappij B.V. Process for the preparation of a rigid polyurethane foam.
JP2001011319A (ja) 1999-06-30 2001-01-16 Kanegafuchi Chem Ind Co Ltd 硬化性組成物
JP2001040064A (ja) 1999-07-30 2001-02-13 Kanegafuchi Chem Ind Co Ltd 硬化性組成物
US6284682B1 (en) 1999-08-26 2001-09-04 The University Of British Columbia Process for making chemically bonded sol-gel ceramics
US6363286B1 (en) 1999-09-24 2002-03-26 Cardiac Pacemakers, Inc. High impedance electrode assembly
JP2001131879A (ja) 1999-10-25 2001-05-15 Kanegafuchi Chem Ind Co Ltd 人工皮革
JP4154815B2 (ja) 1999-10-28 2008-09-24 ぺんてる株式会社 バーコード読み取り装置
US6228945B1 (en) 1999-12-20 2001-05-08 The University Of Akron Three arm star compositions of matter having diblock arms based on polyisobutylene and methods of preparation
US7160949B2 (en) * 2000-01-21 2007-01-09 Mitsui Chemicals, Inc. Olefin block copolymers, processes for producing the same and uses thereof
US6426114B1 (en) 2000-05-02 2002-07-30 The University Of British Columbia Sol-gel calcium phosphate ceramic coatings and method of making same
US7013182B1 (en) 2000-05-04 2006-03-14 Cardiac Pacemakers, Inc. Conductive polymer sheath on defibrillator shocking coils
US6242058B1 (en) 2000-05-12 2001-06-05 Dow Corning Corporation Method for forming coatings from radiation curable compositions containing alkenyl ether functional polyisobutylenes
US6703433B1 (en) 2000-05-12 2004-03-09 Dow Corning Corporation Radiation curable compositions containing alkenyl ether functional polyisobutylenes
AU2001261960A1 (en) 2000-05-19 2001-11-26 The University Of British Columbia Process for making chemically bonded composite hydroxide ceramics
US6555619B1 (en) 2000-06-29 2003-04-29 The University Of Akron Physically crosslinked amphiphilic networks, methods of preparation, and uses thereof
AU2001283358A1 (en) 2000-08-14 2002-02-25 Pharmacia Corporation Drug delivery system with burst electrode
CN1234756C (zh) 2000-10-18 2006-01-04 三井化学株式会社 热塑性聚氨酯弹性体组合物的泡沫体及其制备方法
TW541853B (en) 2000-11-10 2003-07-11 Sumitomo Chemical Co Polymeric fluorescent substance and polymer light-emitting device using the same
US6533955B1 (en) 2000-11-20 2003-03-18 3M Innovative Properties Company Conductive fluoropolymers
US6545097B2 (en) 2000-12-12 2003-04-08 Scimed Life Systems, Inc. Drug delivery compositions and medical devices containing block copolymer
US6704604B2 (en) 2000-12-28 2004-03-09 Medtronic, Inc. System and method for promoting selective tissue in-growth for an implantable medical device
JP3808758B2 (ja) 2001-03-22 2006-08-16 株式会社カネカ イソブチレン系重合体の製造方法
US7396582B2 (en) 2001-04-06 2008-07-08 Advanced Cardiovascular Systems, Inc. Medical device chemically modified by plasma polymerization
US6730324B2 (en) 2001-04-20 2004-05-04 The University Of British Columbia Biofunctional hydroxyapatite coatings and microspheres for in-situ drug encapsulation
US6653365B2 (en) 2001-05-01 2003-11-25 Pentron Clinical Technologies, Llc Dental composite materials and method of manufacture thereof
US7470728B2 (en) 2001-05-01 2008-12-30 Pentron Clinical Technologies Llc Dental glazes and method of manufacture and use thereof
US7160941B2 (en) 2001-05-01 2007-01-09 Pentron Clinical Technologies, Llc Dental composite materials and method of manufacture thereof
ITMI20011306A1 (it) 2001-06-21 2002-12-21 Ausimont Spa Poliuretani vulcanizzabili
US7363091B1 (en) 2001-07-11 2008-04-22 Pacesetter Inc. Method of molding silicone elastomer drug carrier in an endocardial lead
US6600956B2 (en) 2001-08-21 2003-07-29 Cyberonics, Inc. Circumneural electrode assembly
US6852794B2 (en) 2001-09-07 2005-02-08 The Goodyear Tire & Rubber Company Rubber compound containing a polyhedral oligomeric silsesquioxanes
IN2014DN10834A (zh) 2001-09-17 2015-09-04 Psivida Inc
US20030073961A1 (en) 2001-09-28 2003-04-17 Happ Dorrie M. Medical device containing light-protected therapeutic agent and a method for fabricating thereof
JP3969058B2 (ja) 2001-10-31 2007-08-29 東ソー株式会社 軟質ポリウレタンフォームの製造方法
US7187980B2 (en) 2001-11-09 2007-03-06 Oscor Inc. Cardiac lead with steroid eluting ring
WO2003042273A1 (en) 2001-11-14 2003-05-22 Medtronic, Inc. Compounds containing quaternary carbons, medical devices, and methods
US7101956B2 (en) 2001-11-14 2006-09-05 Medtronic, Inc. Compounds containing quaternary carbons, medical devices, and methods
US6709514B1 (en) 2001-12-28 2004-03-23 Advanced Cardiovascular Systems, Inc. Rotary coating apparatus for coating implantable medical devices
US6777026B2 (en) 2002-10-07 2004-08-17 Lord Corporation Flexible emissive coatings for elastomer substrates
US7196142B2 (en) 2002-04-04 2007-03-27 The University Of Akron Polyisobutylene-based block anionomers and cationomers and synthesis thereof
US20030236513A1 (en) 2002-06-19 2003-12-25 Scimed Life Systems, Inc. Implantable or insertable medical devices for controlled delivery of a therapeutic agent
US7292890B2 (en) 2002-06-20 2007-11-06 Advanced Bionics Corporation Vagus nerve stimulation via unidirectional propagation of action potentials
CA2495176A1 (en) 2002-08-13 2004-02-19 Medtronic, Inc. Medical device exhibiting improved adhesion between polymeric coating and substrate
US7438925B2 (en) 2002-08-26 2008-10-21 Biovention Holdings Ltd. Drug eluting coatings for medical implants
DE10241853B3 (de) 2002-09-09 2004-01-22 Byk-Chemie Gmbh Polymeres Harnstoffurethan als Rheologiesteuerungsmittel und Verfahren zur Herstellung
US20040054210A1 (en) 2002-09-17 2004-03-18 Medtronic, Inc. Compounds containing quaternary carbons and silicon-containing groups, medical devices, and methods
US20040063805A1 (en) 2002-09-19 2004-04-01 Pacetti Stephen D. Coatings for implantable medical devices and methods for fabrication thereof
US6770729B2 (en) 2002-09-30 2004-08-03 Medtronic Minimed, Inc. Polymer compositions containing bioactive agents and methods for their use
US7231259B2 (en) 2002-10-04 2007-06-12 Pacesetter, Inc. Body implantable lead comprising electrically conductive polymer conductors
HUP0203632A3 (en) 2002-10-25 2005-08-29 Furukawa Electric Technologiai Recyclable crosslinked polymers with saturated main chain and thermally reversible urethane crosslink points
AU2003298626A1 (en) 2002-11-12 2004-06-03 The Polymer Technology Group Incorporated Control of polymer surface molecular architecture via amphipathic endgroups
US6896965B1 (en) 2002-11-12 2005-05-24 Advanced Cardiovascular Systems, Inc. Rate limiting barriers for implantable devices
JP4160379B2 (ja) 2002-12-26 2008-10-01 株式会社カネカ 熱可塑性エラストマー組成物
US8016752B2 (en) 2003-01-17 2011-09-13 Gore Enterprise Holdings, Inc. Puncturable catheter
US6960207B2 (en) 2003-01-21 2005-11-01 St Jude Medical, Daig Division, Inc. Ablation catheter having a virtual electrode comprising portholes and a porous conductor
US20040147994A1 (en) 2003-01-28 2004-07-29 Cardiac Pacemakers, Inc. Tachy lead system optimized for septal placement
US20050079199A1 (en) 2003-02-18 2005-04-14 Medtronic, Inc. Porous coatings for drug release from medical devices
US20080051866A1 (en) 2003-02-26 2008-02-28 Chao Chin Chen Drug delivery devices and methods
US6926919B1 (en) 2003-02-26 2005-08-09 Advanced Cardiovascular Systems, Inc. Method for fabricating a coating for a medical device
US7172575B2 (en) 2003-03-05 2007-02-06 Advanced Cardiovascular Systems, Inc. Catheter balloon having a lubricious coating
US20040186545A1 (en) 2003-03-20 2004-09-23 Rosero Spencer Z. Temporary percutaneous cardioverter-defibrillator
US7065411B2 (en) 2003-04-23 2006-06-20 Medtronic, Inc. Electrical medical leads employing conductive aerogel
GB0311121D0 (en) 2003-05-15 2003-06-18 Avecia Ltd Polyurethane dispersants
US20050060022A1 (en) 2003-05-21 2005-03-17 Felt Jeffrey C. Polymer stent
US6969744B2 (en) 2003-06-19 2005-11-29 University Of Southern Mississippi Living and quasiliving cationic telechelic polymers quenched by N-substituted pyrrole and methods for their preparation
WO2004114732A1 (en) 2003-06-19 2004-12-29 World Properties, Inc. Material including a liquid crystalline polymer and a polyhedral oligomeric silsesquioxane (poss) filler
WO2004113400A2 (en) 2003-06-20 2004-12-29 Scimed Life Systems, Inc. End-cappped polymer chains and products thereof
EP1639024A4 (en) 2003-07-01 2008-03-12 Univ Akron Akron Ohio THERMOPLASTIC ELASTOMERS MULTIPLOCK COPOLYMERS OF ISOBUTYLENE AND NORBORNE
US7364585B2 (en) 2003-08-11 2008-04-29 Boston Scientific Scimed, Inc. Medical devices comprising drug-loaded capsules for localized drug delivery
US7953499B2 (en) 2003-09-30 2011-05-31 Cardiac Pacemakers, Inc. Drug-eluting electrode
US20050080470A1 (en) 2003-10-09 2005-04-14 Randy Westlund Intramyocardial lead implantation system and method
GB0323733D0 (en) 2003-10-10 2003-11-12 Univ Heriot Watt Conductive polymer
US7807722B2 (en) 2003-11-26 2010-10-05 Advanced Cardiovascular Systems, Inc. Biobeneficial coating compositions and methods of making and using thereof
US7119138B1 (en) 2003-12-19 2006-10-10 Inmat Inc. Barrier coating of a mixture of cured and uncured elastomeric polymers and a dispersed layered filler in a liquid carrier and coated articles
DE112005000177T5 (de) 2004-01-20 2006-12-28 World Properties, Inc., Lincolnwood Schaltungsmaterialien, Schaltungen, Mehrschichtschaltungen und Verfahren zu ihrer Herstellung
GB0401202D0 (en) 2004-01-20 2004-02-25 Ucl Biomedica Plc Polymer for use in conduits and medical devices
US7280875B1 (en) 2004-02-04 2007-10-09 Pacesetter, Inc. High strength, low resistivity electrode
US7056985B2 (en) 2004-02-11 2006-06-06 University Of Massachusetts Lowell End-capped polymer chains and products thereof
US20050180919A1 (en) 2004-02-12 2005-08-18 Eugene Tedeschi Stent with radiopaque and encapsulant coatings
US20070190108A1 (en) 2004-05-17 2007-08-16 Arindam Datta High performance reticulated elastomeric matrix preparation, properties, reinforcement, and use in surgical devices, tissue augmentation and/or tissue repair
US7105622B2 (en) 2004-06-02 2006-09-12 The University Of Akron Hybrid polyurethanes
US20050288476A1 (en) 2004-06-17 2005-12-29 Iskender Yilgor Thermoplastic copolymers through stoichiometric reactions between diisocyanates and oligomeric diols and diamines
JP2006274235A (ja) 2004-07-30 2006-10-12 Fuji Photo Film Co Ltd 重合性組成物、光学異方性層及びその製造方法、光学補償素子、液晶表示装置及び液晶プロジェクタ
JP4155243B2 (ja) 2004-08-04 2008-09-24 トヨタ自動車株式会社 電磁駆動弁
US20060047083A1 (en) 2004-08-30 2006-03-02 Iskender Yilgor Triblock copolymers and their production methods
US7289856B1 (en) 2004-09-29 2007-10-30 Pacesetter, Inc. Medical electrical lead containing a pyroelectric material
US7347751B2 (en) 2004-09-30 2008-03-25 Cardiac Pacemakers, Inc. Cardiac lead implantation system
DE102004048991B4 (de) 2004-10-04 2010-01-28 Biotronik Crm Patent Ag Elektrodenleitung
GB0428444D0 (en) 2004-12-29 2005-02-02 Cambridge Display Tech Ltd Conductive polymer compositions in opto-electrical devices
US8075906B2 (en) 2005-02-01 2011-12-13 Boston Scientific Scimed, Inc. Medical devices having polymeric regions with copolymers containing hydrocarbon and heteroatom-containing monomeric species
US20060264577A1 (en) 2005-04-08 2006-11-23 Rudolf Faust Capping reactions in cationic polymerization; kinetic and synthetic utility
US20060235499A1 (en) 2005-04-14 2006-10-19 Cardiac Pacemakers, Inc. Coated lead fixation electrode
US20070051531A1 (en) 2005-09-08 2007-03-08 Harshad Borgaonkar Drug eluting coatings for a medical lead and method therefor
US7630749B2 (en) 2005-11-07 2009-12-08 Gore Enterprise Holdings, Inc. Implantable electrophysiology lead body
US7715922B1 (en) 2005-11-16 2010-05-11 Pacesetter, Inc. Polyethylene oxide and polyisobutylene copolymers and their usage on medical devices
US7553546B1 (en) 2005-11-16 2009-06-30 Pacesetter, Inc. Polyethylene oxide and silicone copolymers and their usage on medical devices
US8034874B2 (en) 2005-11-23 2011-10-11 Boston Scientific Scimed, Inc. Medical devices having polymeric regions that contain fluorocarbon-containing block copolymers
US20070128246A1 (en) 2005-12-06 2007-06-07 Hossainy Syed F A Solventless method for forming a coating
US7501179B2 (en) 2005-12-21 2009-03-10 Boston Scientific Scimed, Inc. Block copolymer particles
US20070190104A1 (en) 2006-02-13 2007-08-16 Kamath Kalpana R Coating comprising an adhesive polymeric material for a medical device and method of preparing the same
US7981509B2 (en) 2006-02-13 2011-07-19 Donaldson Company, Inc. Polymer blend, polymer solution composition and fibers spun from the polymer blend and filtration applications thereof
US7465777B2 (en) 2006-03-02 2008-12-16 Boston Scientific Scimed, Inc. Hybrid polymer materials from reactive extrusion for medical devices
USD579758S1 (en) 2006-03-23 2008-11-04 Ykk Ap Inc. Sash lock
US7881808B2 (en) 2006-03-29 2011-02-01 Cardiac Pacemakers, Inc. Conductive polymeric coating with optional biobeneficial topcoat for a medical lead
US7737060B2 (en) 2006-03-31 2010-06-15 Boston Scientific Scimed, Inc. Medical devices containing multi-component fibers
EP2001473A4 (en) 2006-03-31 2012-12-26 Advanced Neuromodulation Sys SUBSEQUENT ELECTROSTIMULATION PIPES AND METHOD OF MANUFACTURING THEM
EP2004715A2 (en) 2006-04-07 2008-12-24 University Of Massachusetts Lowell Method to prepare block copolymers by the combination of cationic and anionic polymerization
WO2007119687A1 (ja) 2006-04-13 2007-10-25 Kaneka Corporation ゴム栓用組成物および医療用ゴム栓
US7689291B2 (en) 2006-05-01 2010-03-30 Cardiac Pacemakers, Inc. Lead with fibrous matrix coating and methods related thereto
US7727541B2 (en) 2006-05-18 2010-06-01 Boston Scientific Scimed, Inc. Medical devices having polymeric regions based on vinyl ether block copolymers
US7951194B2 (en) 2006-05-26 2011-05-31 Abbott Cardiovascular Sysetms Inc. Bioabsorbable stent with radiopaque coating
KR101326791B1 (ko) 2006-05-31 2013-11-08 가부시키가이샤 가네카 카테터용 튜브 및 그것으로 이루어지는 카테터
US20080095918A1 (en) 2006-06-14 2008-04-24 Kleiner Lothar W Coating construct with enhanced interfacial compatibility
US9028859B2 (en) 2006-07-07 2015-05-12 Advanced Cardiovascular Systems, Inc. Phase-separated block copolymer coatings for implantable medical devices
DE102006037582A1 (de) 2006-08-11 2008-02-14 Bayer Materialscience Ag Antistatische und elektrisch leitfähige Polyurethane
CA2669970A1 (en) 2006-11-17 2008-05-22 University Of Massachusetts Lowell Functional hydrocarbon polymers and process for producing same
US8163826B2 (en) 2006-11-21 2012-04-24 Schlumberger Technology Corporation Polymeric acid precursor compositions and methods
US20080124555A1 (en) 2006-11-29 2008-05-29 3M Innovative Properties Company Polymerizable composition comprising perfluoropolyether urethane having ethylene oxide repeat units
EP2474563B1 (en) 2006-11-30 2020-01-08 The University of Akron Polyisobutylene-based polyurethane and polyurea
US20160024340A1 (en) 2006-12-14 2016-01-28 Ppg Industries Ohio, Inc. Polyurethanes, articles and coatings prepared therefrom and methods of making the same
US20080167710A1 (en) 2007-01-05 2008-07-10 Vipul Bhupendra Dave Medical Device Having Regions With Various Agents Dispersed Therein and a Method for Making the Same
CN101686854B (zh) 2007-03-09 2012-11-28 阿克伦大学 生物人工胰及其制备方法
CN101646809B (zh) 2007-03-16 2014-01-29 宇部兴产株式会社 氧化锌单晶的制造方法
JP2008238761A (ja) 2007-03-29 2008-10-09 Toyoda Gosei Co Ltd ポリウレタン材料及びその製造方法
WO2008127730A1 (en) 2007-04-12 2008-10-23 The University Of Akron Injectible cyanoacrylate-functionalized polyisobutylenes
EP2574634B1 (en) 2007-06-19 2016-03-02 The University of Akron Process for making singly-terminated polyisobutylenes
EP2197537A1 (en) 2007-10-15 2010-06-23 Cardiac Pacemakers, Inc. Conductive composite electrode material
CA2704508A1 (en) 2007-11-01 2009-05-07 The University Of Akron Thermoplastic amphiphilic co-networks
JP2009132832A (ja) 2007-11-30 2009-06-18 Asahi Glass Co Ltd 一液型ポリウレタン系硬化性組成物およびこれを用いた接着剤
FR2925061B1 (fr) 2007-12-18 2010-01-15 Michelin Soc Tech Composition de caoutchouc notamment pour la fabrication de pneumatique
FR2925062B1 (fr) 2007-12-18 2011-03-04 Michelin Soc Tech Composition de caoutchouc notamment pour la fabrication de pneumatique
US8349123B2 (en) 2008-04-01 2013-01-08 Henkel Corporation High heat resistant adhesive and sealant compositions
US20090292094A1 (en) 2008-05-21 2009-11-26 E. I. Dupont De Nemours And Company Fluoropolymer Composition
CN102131530A (zh) 2008-06-27 2011-07-20 心脏起搏器公司 聚异丁烯-氨基甲酸酯共聚物、聚异丁烯-脲共聚物和聚异丁烯-氨基甲酸酯/脲共聚物及含有这类共聚物的医疗器械
EP2331614B1 (en) 2008-09-19 2012-11-14 Cardiac Pacemakers, Inc. Surface modification to improve lubricity, abrasion resistance and temperature resilience of leads
CA2739402A1 (en) 2008-10-01 2010-04-08 The University Of Akron Polymers having both hard and soft segments, and process for making same
US8285396B2 (en) 2009-01-05 2012-10-09 Kenergy, Inc. MRI compatible electrical lead for an implanted electronic medical device
EP2385960B1 (en) 2009-01-12 2020-03-11 University Of Massachusetts Lowell Polyisobutylene-based polyurethanes
AU2010226254B2 (en) 2009-03-17 2013-08-29 Cardiac Pacemakers, Inc. Porous fiber electrode coating and related methods
US8765238B2 (en) 2009-03-18 2014-07-01 Boston Scientific Scimed, Inc. Polymeric/inorganic composite materials for use in medical devices
US8155759B2 (en) 2009-03-20 2012-04-10 Innovia, Llc Pacemaker lead and method of making same
US20120077934A1 (en) 2009-03-23 2012-03-29 University Of Massachusetts Functional Polyisobutylene Based Macromonomers And Methods For Making And Using The Same
US20100298769A1 (en) 2009-05-21 2010-11-25 Boston Scientific Scimed, Inc. Implantable medical devices for therapeutic agent delivery
CN102573940B (zh) 2009-08-21 2015-04-01 心脏起搏器公司 可交联聚异丁烯类聚合物及包含其的医疗装置
US20110051581A1 (en) 2009-08-25 2011-03-03 Seagate Technology Llc Vibration analysis methodology using data storage devices
US8374704B2 (en) 2009-09-02 2013-02-12 Cardiac Pacemakers, Inc. Polyisobutylene urethane, urea and urethane/urea copolymers and medical leads containing the same
US8644952B2 (en) 2009-09-02 2014-02-04 Cardiac Pacemakers, Inc. Medical devices including polyisobutylene based polymers and derivatives thereof
US8674034B2 (en) 2009-11-11 2014-03-18 The University Of Akron Polyisobutylene-based polyurethanes, polyureas and/or polyurethane-polyureas and method for making same
US20110152989A1 (en) 2009-12-23 2011-06-23 Pacesetter, Inc. Soft abrasion-resistant polyisobutylene urethane copolymers
CN102741365A (zh) 2010-01-21 2012-10-17 太阳化学公司 低voc溶剂系统
EP2555762B1 (en) 2010-04-06 2018-01-31 Syracuse University System and method for the release of nitric oxide using nanoscale media
US8969424B2 (en) 2010-10-15 2015-03-03 Evoqua Water Technologies Llc Anion exchange membranes and process for making
JP5739007B2 (ja) 2010-12-20 2015-06-24 カーディアック ペースメイカーズ， インコーポレイテッド 導電性ポリマー導体を有するリード及びその製造方法
JP5742226B2 (ja) 2011-01-04 2015-07-01 凸版印刷株式会社 ガスバリア性積層体及びその製造方法並びにガスバリア性積層フィルム
US9957346B2 (en) 2011-02-23 2018-05-01 The University Of Akron Melt processible polyureas and polyurea-urethanes, method for the production thereof and products made therefrom
US20130041108A1 (en) 2011-05-19 2013-02-14 Joseph P. Kennedy Polymers having both hard and soft segments, and process for making same
EP2726520A4 (en) 2011-06-30 2015-03-18 Univ Akron PROCESS FOR SYNTHESIS OF COST-EFFECTIVE INITIATORS FOR TELECHELES POLYISOBUTYLENE
EP2741809B1 (en) 2011-08-12 2018-08-01 Cardiac Pacemakers, Inc. Method for coating devices using electrospinning and melt blowing
US9655720B2 (en) 2011-10-13 2017-05-23 The Research Foundation For The State University Of New York Polymeric heart valve
EP2782635B1 (en) 2011-11-23 2020-09-02 Cardiac Pacemakers, Inc. Fibrous matrix coating materials
EA028791B1 (ru) 2012-06-07 2017-12-29 Арагон Фармасьютикалз, Инк. Кристаллическая форма модулятора андрогенных рецепторов
MX2014015459A (es) 2012-06-18 2015-07-14 Petrochemical Supply Inc Composicion de poliisobutileno que tiene vinilideno interno y proceso para preparar la composicion polimerica de poliisobutileno.
JP2015533859A (ja) 2012-07-23 2015-11-26 アクロン大学 有機修飾モンモリロナイトを含有するポリイソブチレン系ポリウレタン
US20140074201A1 (en) 2012-09-11 2014-03-13 Cardiac Pacemakers, Inc. Conformal porous thin layer coating and method of making
EP2922888B1 (en) 2012-11-21 2021-08-18 The University of Massachusetts High strength polyisobutylene polyurethanes
USD689734S1 (en) 2013-02-22 2013-09-17 Hamilton Beach Brands, Inc. Food processor
US9688791B2 (en) * 2013-07-17 2017-06-27 Basf Se High-reactivity polyisobutylene having a high content of vinylidene double bonds in the side chains
CN104231207A (zh) 2014-09-18 2014-12-24 苏州市雄林新材料科技有限公司 一种回收碳纤维增强tpu复合材料及其制备方法
CN104592850B (zh) 2014-12-31 2017-06-23 三棵树涂料股份有限公司 超亲水透明防雾涂层的制备方法
CN104610902B (zh) 2015-02-12 2018-01-30 厦门誉匠复合材料有限公司 快速后固化聚氨酯热熔胶及其制备方法
CN107531911B (zh) 2015-04-23 2021-03-02 心脏起搏器股份公司 用于具有高重量百分比共聚物的共聚物溶液的组合物和方法
CN108368229A (zh) 2015-12-17 2018-08-03 心脏起搏器股份公司 聚异丁烯-聚氨酯和含有它们的医疗装置
US10472457B2 (en) 2016-01-21 2019-11-12 The University Of Akron Initiators for living carbocationic polymerization
CN109071757A (zh) 2016-05-10 2018-12-21 心脏起搏器股份公司 热固性聚异丁烯-聚氨酯及其制备方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1745111A (zh) * 2003-01-28 2006-03-08 巴斯福股份公司 利用硼氢化进行的异丁烯聚合物官能化
US20060135721A1 (en) * 2003-06-26 2006-06-22 Arno Lange Method for producing polyisobutenes
US20160008607A1 (en) * 2014-07-11 2016-01-14 Cardiac Pacemakers, Inc. Polymeric feed-thru for chronic implantable devices

Also Published As

Publication number Publication date
EP3592786B1 (en) 2023-05-10
US20180258196A1 (en) 2018-09-13
US10526429B2 (en) 2020-01-07
WO2018165273A1 (en) 2018-09-13
EP3592786A1 (en) 2020-01-15
CN110382568A (zh) 2019-10-25

Similar Documents

Publication Publication Date Title
CN110382568B (zh) 烯丙基封端的聚异丁烯的硼氢化/氧化
KR101519826B1 (ko) 폴리이소부틸렌 및 그 제조방법
CN108290981A (zh) 包含稀土茂金属的预先形成的催化体系
TWI617540B (zh) 交聯有機聚合物組成物及用於控制與改良交聯反應速率以增進加工性的方法
US4151113A (en) Halogenated organoaluminum compounds and method of preparation
JP2004525232A (ja) シス位二重結合の高い含量を有する変性ポリマー、その製法ならびにその使用
CN110475795B (zh) 聚烯烃-聚苯乙烯多嵌段共聚物，用于制备其的有机锌化合物及其制备方法
JP3498272B2 (ja) トリオルガノ置換スズリチウム開始剤
CN111918896A (zh) 制备嵌段共聚物组合物的方法
CN101195489A (zh) 氢硼化物氟化的方法
CN109415458B (zh) 用于氢介导的盐型氢化物引发的阴离子链转移聚合的方法和催化剂
US6197089B1 (en) Activated magnesium metal
NO774305L (no) Koplingsmidler.
US4325840A (en) Organomagnesium complexes
KR101834829B1 (ko) 유기 아연 화합물 및 그 제조 방법
JP6903068B2 (ja) 高反応性イソブテンホモポリマーまたはコポリマーの製造方法
JP6754007B2 (ja) ポリジエンの生成方法
US8283427B2 (en) Heterogeneous perfluoroaryl substituted Lewis acid catalysts for cationic polymerizations
CN109928987B (zh) 制备邻氯苄基氯化镁类化合物的方法
JP2006523767A (ja) ビス（ボラン）共開始剤を使用する、炭化水素媒体中でのｉ−ブテンの重合
Roesky Surprising results in fluorine chemistry and related elements
JP2004331775A (ja) 末端に官能基を有するポリマー及びその製造方法
EP1115749B1 (en) A process for making functionalized polymers
JPH10316686A (ja) トリチルテトラキス（ペンタフルオロフェニル）ボレートの製造方法
JP2005008620A (ja) オキセタニル基とカルボキシル基を有する新規モノマーとそれから誘導されるポリエステルの製造方法

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant