公开(公告)号：US20170066662A1

公开(公告)日：2017-03-09

申请号：US15353615

申请日：2016-11-16

Applicant: International Business Machines Corporation

Inventor： Dylan J. BODAY ,  Jeannette M. GARCIA ,  James L. HEDRICK ,  Gavin O. JONES ,  Rudy J. WOJTECKI

IPC: C02F1/28 ,  B01J20/26

CPC classification number: B01J20/262 ,  B01D15/08 ,  C02F1/285 ,  C02F1/683 ,  C02F2101/20 ,  C02F2201/002 ,  C02F2303/16

Abstract: Method and apparatus for controlling metals in a liquid are described. The liquid is contacted with a hexahydrotriazine and/or a hemiaminal material, and metal is adsorbed from the liquid onto the material. The hexahydrotriazine and/or hemiaminal material may be made from a diamine and an aldehyde.

Abstract translation: 描述了用于控制液体中的金属的方法和装置。 液体与六氢三嗪和/或半合金材料接触，金属从液体吸附到材料上。 六氢三嗪和/或噻嗪类材料可以由二胺和醛制成。

公开(公告)号：US20160108164A1

公开(公告)日：2016-04-21

申请号：US14564159

申请日：2014-12-09

Applicant: International Business Machines Corporation

Inventor： Dylan J. BODAY ,  Jeannette M. GARCIA ,  James L. HEDRICK ,  Rudy J. WOJTECKI

IPC: C08G12/08 ,  B05D1/12 ,  C09D161/22

CPC classification number: C08G12/08 ,  B05D1/12 ,  C08G12/46 ,  C09D5/03 ,  C09D161/22 ,  C09D179/04 ,  C09D179/06 ,  C09D181/02

Abstract: A coating for an article may be made by applying a powder of a polyhemiaminal (PHA) polymer material to the article in a particulate form and then converting the PHA polymer material to a polyhexahydrotriazine (PHT) polymer material and fusing the particles into a monolithic coating by applying heat to the particles. The method generally includes forming a dilute reaction mixture comprising a formaldehyde reactant, a solvent, a primary aromatic diamine, and heating the reaction mixture to a temperature of between about 20° C. and about 120° C. for a short time to form a polymer. A particulate solid is precipitated by adding an excess volume of a non-solvent to the mixture. The powder may be applied to an article and then heated to fuse the powder into a coating and convert the PHA to PHT.

Abstract translation: 用于制品的涂层可以通过将聚合物（PHA）聚合物材料的粉末以颗粒形式施加到制品上，然后将PHA聚合物材料转化为聚六氢三嗪（PHT）聚合物材料并将颗粒熔合成整体涂层 通过向颗粒施加热量。 该方法通常包括形成包含甲醛反应物，溶剂，伯芳族二胺的稀释反应混合物，并将反应混合物加热至约20℃至约120℃的温度很短时间以形成 聚合物。 通过向混合物中加入过量体积的非溶剂来沉淀出颗粒状固体。 粉末可以施加到制品上，然后加热以将粉末熔合成涂层并将PHA转化成PHT。

公开(公告)号：US20160046831A1

公开(公告)日：2016-02-18

申请号：US14461844

申请日：2014-08-18

Applicant: International Business Machines Corporation

Inventor： Dylan J. BODAY ,  Jeannette M. GARCIA ,  James L. HEDRICK ,  Alshakim NELSON ,  Rudy J. WOJTECKI

IPC: C09D161/20 ,  B29C67/00 ,  C09D125/06

CPC classification number: C08L61/22 ,  B29C64/00 ,  B29C64/106 ,  B29K2061/00 ,  B29K2079/00 ,  B29L2031/726 ,  B33Y10/00 ,  B33Y70/00 ,  C08G12/06 ,  C08G12/08 ,  C08J5/04 ,  C08J5/24 ,  C08J2300/208 ,  C08J2361/22 ,  C09D125/06

Abstract: This application describes methods of forming an object. The methods described include forming a mixture with i) one or more primary diamines, ii) one or more polymerizable monomers, iii) a formaldehyde-type reagent, and iv) a polymerization initiator; forming a gel by heating the mixture to a temperature of at least 50° C.; and curing the one or more polymerizable monomers by activating the polymerization initiator. The one or more primary diamines may include one or more amine functional oligomers and/or primary aromatic diamine small molecules. The one or more polymerizable monomers may include styrenics, acrylates, methacrylates, vinyl esters, unsaturated polyesters, and derivatives thereof. The gel is a polyhemiaminal (PHA), a polyhexahydrotriazine (PHT), and/or a polyoctatriazacane (POTA) polymer, and curing of the gel forms an interpenetrating network of the PHA/PHT/POTA and the polymer formed from the polymerizable monomers.

Abstract translation: 本应用程序描述了形成对象的方法。 所述方法包括与i）一种或多种伯二胺形成混合物，ii）一种或多种可聚合单体，iii）甲醛型试剂，和iv）聚合引发剂; 通过将混合物加热至至少50℃的温度来形成凝胶; 并通过活化聚合引发剂来固化一种或多种可聚合单体。 一个或多个伯二胺可以包括一种或多种胺官能低聚物和/或伯芳族二胺小分子。 一种或多种可聚合单体可以包括苯乙烯，丙烯酸酯，甲基丙烯酸酯，乙烯酯，不饱和聚酯及其衍生物。 该凝胶是聚柠檬酸（PHA），聚六氢三嗪（PHT）和/或聚辛酰三氮（POTA）聚合物，并且凝胶的固化形成PHA / PHT / POTA和由可聚合单体形成的聚合物的互穿网络。

公开(公告)号：US20160046803A1

公开(公告)日：2016-02-18

申请号：US14564973

申请日：2014-12-09

Applicant: International Business Machines Corporation

Inventor： Dylan J. BODAY ,  Jeannette M. GARCIA ,  James L. HEDRICK ,  Alshakim NELSON ,  Rudy J. WOJTECKI

IPC: C08L61/22 ,  B29C67/00 ,  C09D161/22

CPC classification number: C08L61/22 ,  B29C64/00 ,  B29C64/106 ,  B29K2061/00 ,  B29K2079/00 ,  B29L2031/726 ,  B33Y10/00 ,  B33Y70/00 ,  C08G12/06 ,  C08G12/08 ,  C08J5/04 ,  C08J5/24 ,  C08J2300/208 ,  C08J2361/22 ,  C09D125/06

Abstract: This application describes methods of forming an object. The methods described include forming a mixture with i) one or more primary diamines, ii) one or more polymerizable monomers, iii) a formaldehyde-type reagent, and iv) a polymerization initiator; forming a gel by heating the mixture to a temperature of at least 50° C.; and curing the one or more polymerizable monomers by activating the polymerization initiator. The one or more primary diamines may include one or more amine functional oligomers and/or primary aromatic diamine small molecules. The one or more polymerizable monomers may include styrenics, acrylates, methacrylates, vinyl esters, unsaturated polyesters, and derivatives thereof. The gel is a polyhemiaminal (PHA), a polyhexahydrotriazine (PHT), and/or a polyoctatriazacane (POTA) polymer, and curing of the gel forms an interpenetrating network of the PHA/PHT/POTA and the polymer formed from the polymerizable monomers.

公开(公告)号：US20160024253A1

公开(公告)日：2016-01-28

申请号：US14340221

申请日：2014-07-24

Applicant: International Business Machines Corporation

Inventor： Dylan J. BODAY ,  Jeannette M. GARCIA ,  James Lupton HEDRICK ,  Rudy J. WOJTECKI

IPC: C08G73/06 ,  C08G73/02

CPC classification number: C08G73/065 ,  C08G73/0644

Abstract: Polyhexahydrotriazine (PHT) and polyhemiaminal (PHA) materials chemically modified to include thermoplastic polymer bridging groups, and methods of making such materials, are disclosed. The materials are formed by a process that includes heating a mixture comprising i) a solvent, ii) paraformaldehyde, iii) a diamine monomer comprising two primary aromatic amine groups, and iv) a polymer diamine at a temperature of about 20° C. to less than 150° C. This heating step forms a stable PHA in solution, which can be isolated. The PHA includes covalently bonded thermoplastic polymer groups. The PHA is then heated at a temperature of 150° C. to about 280° C., thereby converting the PHA material to a PHT material that includes covalently bonded thermoplastic polymer groups.

公开(公告)号：US20150376442A1

公开(公告)日：2015-12-31

申请号：US14571130

申请日：2014-12-15

Applicant: International Business Machines Corporation

Inventor： Dylan J. BODAY ,  Jeannette M. GARCIA ,  James L. HEDRICK ,  Rudy J. WOJTECKI

IPC: C09D161/20

CPC classification number: C09D179/04 ,  B05D1/30 ,  C08G12/08 ,  C08G73/0273 ,  C08G73/0638 ,  C09D161/22

Abstract: Polyhexahydrotriazine (PHT) and polyhemiaminal (PHA) materials incorporating divalent or trivalent bridging groups tend to form highly cross-linked polymers. While highly cross-linked polymers have certain advantageous with respect to stability and various physical characteristics, they are difficult to process once formed. PHA and PHT materials incorporating a plurality of trivalent PHA/PHT groups, a plurality of divalent bridging groups, and a plurality of monovalent end groups are disclosed. According to an embodiment, the cross-link density and molecular weight can be controlled by the inclusion of the end groups. Lower cross-link density and molecular weight give PHA and PHT materials improved characteristics with respect to film and fiber formation methods. A method of coating a component or substrate with a polymer is also disclosed. Embodiments of the method can be used to form either a PHA or PHT film on a substrate, such as microelectronic component.

公开(公告)号：US20150366972A1

公开(公告)日：2015-12-24

申请号：US14311223

申请日：2014-06-20

Applicant: International Business Machines Corporation

Inventor： Dylan J. BODAY ,  Jeannette M. GARCIA ,  James L. HEDRICK ,  Rudy J. WOJTECKI

IPC: A61K47/34 ,  C08G73/06

CPC classification number: A61K47/59 ,  A61K47/34 ,  A61K47/60 ,  C08G12/08 ,  C08G12/40 ,  C08G64/0216 ,  C08G73/06 ,  C08G73/0644

Abstract: Methods for preparing a supramolecular therapeutic agent delivery assembly are provided. A hydrophilic precursor, a hydrophibic precursor, and an aromatic diamine precursor may be combined to form an amphiphilic block co-polymer. The block co-polymer may undergo a cross-linking polymerization process and a therapeutic agent may be incorporated into the resulting supramolecular assembly. The supramolecular assembly may comprise HT, PHT, HA, and/or PHA materials.

Abstract translation: 提供了制备超分子治疗剂递送组件的方法。 亲水性前体，亲水性前体和芳族二胺前体可以组合形成两亲嵌段共聚物。 嵌段共聚物可以经历交联聚合方法，并且治疗剂可以并入所得的超分子组装体中。 超分子组件可以包含HT，PHT，HA和/或PHA材料。

公开(公告)号：US20150360173A1

公开(公告)日：2015-12-17

申请号：US14832281

申请日：2015-08-21

Applicant: International Business Machines Corporation

Inventor： Dylan J. BODAY ,  Jeannette M. GARCIA ,  James L. HEDRICK ,  Rudy J. WOJTECKI

IPC: B01D53/48 ,  C09D5/08 ,  B01D39/08 ,  C09D179/02 ,  C10L3/10 ,  C10G29/20 ,  C09D179/04

CPC classification number: B01D53/48 ,  A61L2/00 ,  A61L9/00 ,  B01D24/02 ,  B01D24/36 ,  B01D39/04 ,  B01D39/083 ,  B01D53/02 ,  B01D53/38 ,  B01D53/46 ,  B01D53/82 ,  B01D53/92 ,  B01D2239/0407 ,  B01D2257/30 ,  B01D2257/302 ,  B01D2257/304 ,  B01D2257/306 ,  B01D2258/0283 ,  B01D2258/06 ,  B01J20/22 ,  B01J20/28023 ,  B01J20/28038 ,  C08G73/02 ,  C08G73/0638 ,  C08G73/0644 ,  C08G2150/90 ,  C08G2340/00 ,  C09D5/08 ,  C09D5/082 ,  C09D5/086 ,  C09D179/02 ,  C09D179/04 ,  C10G25/003 ,  C10L3/103 ,  C10L2230/14 ,  C10L2290/542 ,  C10L2290/547

Abstract: Materials which react with (“scavenge”) sulfur compounds, such as hydrogen sulfide and mercaptans, are used to limit sulfur-induced corrosion. Filters and protective coatings including these materials, described broadly as polyhexahydrotriazines (PHT) and polyhemiaminals (PHA), are disclosed. Methods of using these materials to prevent corrosion are described. PHT and PHA materials have excellent thermal and mechanical properties for many applications as coatings and filtration media. Specifically, PHT and PHA materials react with sulfur compounds in such a manner as to incorporate sulfur atoms into the polymeric matrix, thus sequestering the sulfur atoms and allowing removal from fluids such as crude oil, natural gas, hydrocarbon combustion exhaust gases, sulfur polluted air and water. A coating PHT or PHA material on a component to be protected similarly reacts with sulfur compounds prior to sulfur being able to penetrate to the component.

Abstract translation: 与（“清除”）硫化合物（例如硫化氢和硫醇）反应的材料用于限制硫引起的腐蚀。 公开了包括这些材料的过滤器和保护涂层，广泛地被描述为聚六氢三嗪（PHT）和聚合物（PHA）。 描述了使用这些材料以防止腐蚀的方法。 PHT和PHA材料具有优异的热和机械性能，适用于许多应用，如涂料和过滤介质。 具体地说，PHT和PHA材料与硫化合物反应，以将硫原子引入聚合物基质中，从而将硫原子隔离并允许从诸如原油，天然气，烃燃烧废气，硫污染空气 和水。 待保护的组分上的涂层PHT或PHA材料在硫能够渗入组分之前，类似地与硫化合物反应。

公开(公告)号：US20150353584A1

公开(公告)日：2015-12-10

申请号：US14830467

申请日：2015-08-19

Applicant: International Business Machines Corporation

Inventor： Dylan J. BODAY ,  Jeannette M. GARCIA ,  James L. HEDRICK ,  Rudy J. WOJTECKI

IPC: C07F7/02 ,  C02F1/28 ,  B01J20/22 ,  B01J20/32 ,  B01D53/02 ,  B01J20/28

CPC classification number: C07F7/025 ,  B01D39/04 ,  B01D53/02 ,  B01D53/48 ,  B01D53/508 ,  B01D53/82 ,  B01D2253/106 ,  B01D2253/20 ,  B01D2253/25 ,  B01D2253/304 ,  B01D2257/30 ,  B01D2257/304 ,  B01D2257/306 ,  B01J20/22 ,  B01J20/28016 ,  B01J20/28019 ,  B01J20/3255 ,  C02F1/285 ,  C02F1/288 ,  C02F2101/101 ,  C02F2103/10 ,  C02F2103/365 ,  C02F2303/08 ,  C07D251/24 ,  C07F7/0836 ,  C07F7/1804 ,  C08K5/3492 ,  Y10T428/2982 ,  Y10T428/2991 ,  Y10T428/2993 ,  Y10T428/2995

Abstract: Materials which react with (“scavenge”) sulfur compounds, such as hydrogen sulfide and mercaptans, are useful for limiting sulfur-induced corrosion. Surface-modified particles incorporating a hexahydrotriazine moiety are disclosed and used as sulfur scavengers. These surface-modified particles are used a filter media in fixed filter systems and as additives to fluids including sulfur compounds. The hexahydrotriazine moiety can react with sulfur compounds in such a manner as to bind sulfur atoms to the surface-modified particles, thus allowing removal of the sulfur atoms from fluids such as crude oil, natural gas, hydrocarbon combustion exhaust gases, sulfur polluted air and water. The surface-modified particles may, in general, be sized to allow separation of the particles from the process fluid by sedimentation, size-exclusion filtration or the like.

公开(公告)号：US20200046646A1

公开(公告)日：2020-02-13

申请号：US16658299

申请日：2019-10-21

Applicant: International Business Machines Corporation

Inventor： Dylan J. BODAY ,  Jeannette M. GARCIA ,  James L. HEDRICK ,  Brandon M. KOBILKA ,  Jason T. WERTZ ,  Rudy J. WOJTECKI

IPC: A61K9/50

Abstract: Materials and methods for preparing a payload-containing microcapsule with walls that have hexahydrotriazine (HT) and/or hemiaminal (HA) structures are disclosed. To an HT small molecule or a HA small molecule, or a combination thereof, in a solvent is added a cross-linking agent, NH4Cl, and a copolymer. The solution is acidified, and a payload agent is added. The HT small molecule and HA small molecule may have orthogonal functionality.