CN110997863A - 涂覆的颗粒、其制备方法及其作为支撑剂的使用方法 - Google Patents
涂覆的颗粒、其制备方法及其作为支撑剂的使用方法 Download PDFInfo
- Publication number
- CN110997863A CN110997863A CN201880053321.4A CN201880053321A CN110997863A CN 110997863 A CN110997863 A CN 110997863A CN 201880053321 A CN201880053321 A CN 201880053321A CN 110997863 A CN110997863 A CN 110997863A
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- China
- Prior art keywords
- isocyanate
- mixture
- coated particle
- particles
- weight
- 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.)
- Pending
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- 230000000670 limiting effect Effects 0.000 description 6
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
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- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 5
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- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- BOTMPGMIDPRZGP-UHFFFAOYSA-N triethoxy(isocyanatomethyl)silane Chemical compound CCO[Si](OCC)(OCC)CN=C=O BOTMPGMIDPRZGP-UHFFFAOYSA-N 0.000 description 1
- ROWWCTUMLAVVQB-UHFFFAOYSA-N triethoxysilylmethanamine Chemical compound CCO[Si](CN)(OCC)OCC ROWWCTUMLAVVQB-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- ARKBFSWVHXKMSD-UHFFFAOYSA-N trimethoxysilylmethanamine Chemical compound CO[Si](CN)(OC)OC ARKBFSWVHXKMSD-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 239000008170 walnut oil Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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Abstract
公开了涂覆的颗粒。所述涂覆的颗粒包括基质颗粒和置于至少一部分基质颗粒上的涂层。所述涂层包含以下反应混合物的缩合反应产物,所述反应混合物包含液体的异氰酸酯官能化组分和异氰酸酯反应性组合物。还公开了用于制备这种颗粒的方法以及在水力压裂法中使用这种颗粒作为支撑剂的方法。
Description
技术领域
本说明书涉及涂覆的颗粒、其制备方法以及在水力压裂法中使用这种颗粒作为支撑剂的方法。
背景技术
水力压裂法是其中通过注入加压材料使邻近钻孔排列的地下地质层断裂,以从所述地质层中提取所需物质,如油和/或气(如天然气)的方法。注入加压材料在地质层中产生了通道(即裂缝),所需物质可通过该通道流至钻孔并被取回。在该方法中,注入到地质层中的材料通常是携带固体颗粒(其通常被称为支撑剂)的液体。支撑剂通常是颗粒(如沙子),其具有被置于颗粒上的涂层。支撑剂迁移到所形成的裂缝中,并保持裂缝张开,以使所需材料可从所述裂缝中流出。
许多现有支撑剂、特别是在低温(不大于150℉)井中使用的那些支撑剂的一个问题是抗破碎性不足。抗破碎性是指支撑剂在高压下抵抗破裂的能力。抗破碎性差的支撑剂不能有效地支撑地质层中张开的裂缝,并且可能有助于使提取的燃料物质中包含粉尘颗粒。然而,即使对于最初表现出良好的抗破碎性的支撑剂,仍存在的另一个问题是随着时间的推移,支撑剂不能保持这种良好的抗破碎性。换句话说,支撑剂表现出差的储存期稳定性。
此外,由可再生资源衍生的材料在商业上正变得更加可取,部分原因是石油衍生的原料的成本增加。基于可再生资源的产品的“绿色”形象也已成为各种产品营销中的重要因素;然而,与由石油基材料制备的那些支撑剂相比,例如使用这种材料制备的经涂覆的任意支撑剂的物理特性和性能均不应受到不利影响。此外,零售商和政府机构希望在他们出售或购买的成品中具有更高的可再生资源含量,以利用该“绿色”形象或减少对石油基材料的依赖。
结果是,期望提供可用在水力压裂法中作为例如支撑剂的改善的涂覆的颗粒,其中所述支撑剂具有良好的抗破碎性(如通过无侧限抗压强度(“UCS”)所测量)并且还能够在相当长的时间内保持其UCS,即,其具有延长的储存期稳定性。此外,还期望提供这样的颗粒,其中涂层衍生自大量的生物基的/可再生的材料。
在本说明书中记载的发明是基于前述内容所作出的。
发明内容
在某些方面,本说明书涉及涂覆的颗粒,其包括:(a)粒径不大于3目的基质颗粒;和(b)置于至少一部分颗粒上的涂层,其中所述涂层包含反应混合物的缩合反应产物,所述反应混合物包含:(i)包含至少10重量%的2,4'-亚甲基二苯基二异氰酸酯和/或2,2'-亚甲基二苯基二异氰酸酯的亚甲基二苯基二异氰酸酯混合物,基于混合物的总重量计;和(ii)包含以下物质的异氰酸酯反应性组合物:(A)植物油聚酯多元醇;(B)芳族二胺;和(C)用于羟基和异氰酸酯基团之间的反应的催化剂。
在其他方面,本说明书涉及涂覆的颗粒,其包括:(a)粒径不大于3目的基质颗粒;和(b)置于至少一部分颗粒上的涂层,其中所述涂层包含(1)包含以下物质的反应混合物的缩合反应产物:(i)液体的异氰酸酯官能化组分;和(ii)包含下述物质的异氰酸酯反应性组合物:(A)如上所述的多元醇,如植物油聚酯多元醇;(B)芳族二胺;(C)用于羟基和异氰酸酯基团之间的反应的催化剂;和(2)解晶温度为至少35℃的结晶或半结晶的聚酯/聚氨酯。
本说明书还涉及例如用于制备这种涂覆的颗粒的方法以及例如在水力压裂地质层中使用所述涂覆的颗粒的方法。
具体实施方式
在本说明书中记载和示例性说明了多个实施方案,以提供对本公开发明的结构、功能、性能和用途的全面理解。应当理解,在本说明书中记载和示例说明的各实施方案是非限制性的和非穷举性的。因此,本发明不受本说明书中所公开的各种非限制性且非穷举性的实施方案的描述的限制。所记载的与各实施方案有关的特征和特性可与其他实施方案的特征和特性结合。这样的修改和变化旨在包括在本说明书的范围内。因此,可以修改权利要求书以描述在本说明书中明确记载或固有记载的任何特征或特性,或由本说明书明确支持或固有支持的任何特征或特性。此外,申请人保留修改权利要求以明确地放弃可能存在于现有技术中的特征或特性的权利。因此,任何这样的修改均符合35 U.S.C.§112和35U.S.C.§132(a)的规定。在本说明书中公开和记载的各实施方案可包括如本文中记载的各种特征和特性,由这些特征和特性组成,或基本上由这些特征和特性组成。
除非另有说明,否则本文中提及的任何专利、出版物或其他公开材料均通过引用的方式将全文纳入本说明书中,但仅限于所纳入的材料与本说明书中明确阐述的已有定义、陈述或其他公开材料不存在相互冲突的程度。因此,在必要的程度上,在本说明书中所阐述的明确公开内容取代了通过引用并入本文中的任何相冲突的材料。被描述为通过引用并入本说明书中的任何材料或其部分——但并不与本文中所阐述的已有定义、陈述或其他公开材料相冲突——均仅以这样的程度并入,使得在所并入的材料和已有公开材料之间不发生冲突。申请人保留修改本说明书以明确阐述通过引用纳入本文中的任何主题或其部分的权利。
在本说明书中,除另有说明外,否则所有的数值参数均应理解为在所有情况下都以术语“约”开始,并被术语“约”修饰,其中所述数值参数具有用于测定该参数数值的基本测量技术所固有的可变属性。至少——并且不是试图限制等同原则对权利要求书范围的适用——在本说明书中记载的各数值参数应至少根据所记录的有效数字的数值并通过采用一般的舍入技术进行解释。
此外,在本说明书中所列举的任何数值范围均旨在包括所述范围内包含的相同数值精度的所有子范围。例如,范围“1.0至10.0”旨在包括介于(并且包括)所述最小值1.0和所述最大值10.0之间的所有子范围,即,最小值等于或大于1.0且最大值等于或小于10.0,例如2.4至7.6。在本说明书中所述的任何最大数值极限均旨在包括其中所包含的所有较低的数值极限,并且在本说明书中所述的任何最小数值极限均旨在包括其中所包含的所有较高的数值极限。因此,申请人保留修改本说明书,包括权利要求书,以明确地阐述本文中明确地阐述的范围内所包含的任何子范围的权利。所有这样的范围均旨在固有地记载在本说明书中,以便修改以明确地描述任何这样的子范围符合35 U.S.C.§112和35 U.S.C.§132(a)的规定。
除非另有说明,否则在本说明书中使用的语法冠词“一(one)”、“一个(a)”、“一种(an)”和“所述”旨在包括“至少一个(种)”或“一个或更多个(种)”。因此,在本说明书中所用的冠词是指一个(种)或多于一个(种)(即,“至少一个(种)”)所述冠词的语法对象。举例来说,“一种组分”意指一种或多种组分,因此,可预期多于一种组分,并且在所记载的实施方案的实施中可应用或使用多于一种组分。此外,除非上下文另有使用要求,否则使用的单数名词包括复数,且使用的复数名词包括单数。
如文中所示,本说明书的某些实施方案涉及涂覆的颗粒。如本文中所使用的,术语“颗粒”和“微粒”可互换使用,并且各自指离散的三维形状的物体。适用于本文的颗粒可具有任意的形状,包括例如通常的球形或细长形。在某些实施方案中,颗粒的长径比为1:1(完美球体)至最高达1:100、最高达1:50、最高达1:20或在一些情况下最高达1:10或最高达1:5。如本文中所使用的,颗粒的“长径比”是颗粒最短尺寸的长度与该颗粒最长尺寸的长度之比。
本说明书的涂覆的颗粒包括基质颗粒。基质颗粒可由任意材料(包括例如有机材料和无机材料)制成。在某些实施方案中,基质颗粒包含使涂覆的颗粒适合在地质层的水力压裂中用作支撑剂的材料。如本文中所使用的,术语“支撑剂”是指被注入到地下地质地的裂缝中的颗粒,如可围绕钻孔(如与油井、水井、气井等连接的钻孔)以支撑处于张开状态的裂缝,从而允许所需材料(如油、水、天然气或其他材料)通过该裂缝流至钻孔取回的那些颗粒。
在一些实施方案中,基质颗粒的粒径不大于3目(6730μm)、不大于6目(3360μm)、不大于10目(2000μm)、不大于20目(841μm)、不大于40目(400μm);或在一些情况下,不大于50目(297μm)、不大于60目(250μm)、不大于70目(210μm)、不大于80目(177μm)、不大于100目(149μm)、不大于200目(74μm);或在一些情况下,不大于400目(37μm)。在基质颗粒包含沙子的一些实施方案中,例如,粒径不大于40目(400μm)或在一些情况下不大于50目(297μm)或不大于60目(250μm)。如本文中所使用的,“目”是指美国标准测试筛号。如本文中所使用的,“粒径”是指离散的单个颗粒的最大尺寸(与单个颗粒的团聚物相对)。
如文中所示,基质颗粒可包含任意材料(包括有机材料和无机材料)。在某些实施方案中,基质颗粒包含无机材料如粘土、石墨、玻璃、空心微球、矿渣、沙子、矿物纤维和/或陶瓷。在某些实施方案中,基质颗粒包含有机材料如有机聚合物和/或天然存在的有机材料。
在本说明书中记载的颗粒可以是自由流动的颗粒。如本文中所使用的,“自由流动的颗粒”是指干燥的颗粒,其不是彼此粘结或粘附以致形成团块的颗粒的聚集体。在一些实施方案中,当使颗粒通过10目(2000μm)的筛子时,本说明书的“自由流动的颗粒”的休止角小于例如60°度。此外,在一些实施方案中,本说明书的自由流动的颗粒是这样的,在140℉/95%相对湿度下1周后,所述颗粒的至少85重量%(如至少90重量%或在一些情况下至少95重量%)可倾倒。
本说明书的某些实施方案涉及涂覆的颗粒,其包括置于至少一部分颗粒上的涂层。在某些实施方案中,所述涂层在实质上是覆盖了基质颗粒的全部表面或基本上全部表面的连续的膜。如本文中所使用的,“基本上全部的”是指所述涂层覆盖了基质颗粒的至少90%的表面。应当理解,本说明书的涂覆的颗粒不同于其中颗粒简单地分散在聚合物基质或粘合剂中的情况。
本说明书的颗粒的某些实施方案包括涂层,所述涂层包含反应混合物的缩合反应产物,所述反应混合物包含:(i)液体的异氰酸酯官能化组分;和(ii)异氰酸酯反应性组合物。
例如,在本说明书的颗粒的一些实施方案中,液体的异氰酸酯官能化组分包含亚甲基二苯基二异氰酸酯混合物。如本文中所使用的,术语“亚甲基二苯基二异氰酸酯混合物”是指亚甲基二苯基二异氰酸酯单体(“MDI”)的各种异构体的混合物,如2,2'-MDI、2,4'-MDI和4,4'-MDI中至少两种的混合物,其可以与其他异氰酸酯官能化组分(如聚合的亚甲基二苯基二异氰酸酯(“p-MDI”))组合而存在。
更具体地,在本说明书的颗粒的某些实施方案中,亚甲基二苯基二异氰酸酯混合物包含相对大量的2,2'-MDI和/或2,4-MDI;在一些情况下,包含相对大量的2,4'-MDI。甚至更具体地,在某些实施方案中,这种亚甲基二苯基二异氰酸酯混合物包含至少10重量%(如至少15重量%)的2,4'-MDI和/或2,2'-MDI;在一些情况下,包含至少10重量%(如至少15重量%)的2,4'-MDI,基于混合物的总重量计。在一些实施方案中,这种亚甲基二异氰酸酯混合物包含至少25重量%的2,4'-MDI和/或2,2'-MDI;在一些情况下,包含至少25重量%的2,4'-MDI,基于混合物中MDI的总重量计。事实上,出人意料地发现,使用包含相对大量的2,2'-MDI和/或2,4'-MDI、特别是2,4'-MDI的这种亚甲基二苯基二异氰酸酯混合物可提供表现出非常高(大于75%,在一些情况下,90%或更高)的UCS保留率%(当在实施例中所记载的条件下测量)的本说明书的支撑剂颗粒。
在本说明书的颗粒的一些实施方案中,液体的异氰酸酯官能化组分包含氨基甲酸酯改性的二苯基甲烷二异氰酸酯预聚物,该预聚物通过使过量的多亚甲基多(苯基异氰酸酯)与异氰酸酯反应性组分反应以形成异氰酸酯封端的预聚物而制备。适用于制备液体的氨基甲酸酯改性的二苯基甲烷二异氰酸酯预聚物的异氰酸酯反应性组分包括例如聚醚多元醇和聚酯多元醇。
例如,在一些实施方案中,为制备液体的氨基甲酸酯改性的异氰酸酯封端的预聚物而使用的异氰酸酯反应性组分包含聚酯多元醇。在这些实施方案中,异氰酸酯封端的预聚物通过使聚合的二苯基甲烷二异氰酸酯(例如,其中异氰酸酯含量为29至33.5%(如31至约32.5%)和/或其在25℃下的粘度为50至1 000mPa·s(如100至约350mPa·s或150至220mPa·s))与聚酯多元醇或包含聚酯多元醇的多元醇的掺混物反应制备。在一些实施方案中,所用的聚合的二苯基甲烷二异氰酸酯包括38至50重量%(基于异氰酸酯的总重量计)的单体二苯基甲烷二异氰酸酯(如42至48重量%的单体二苯基甲烷二异氰酸酯),聚合的二苯基甲烷二异氰酸酯的余量由二苯基甲烷二异氰酸酯的高级低聚物补足。
在这些实施方案中,使聚合的二苯基甲烷二异氰酸酯与多元醇(如聚酯多元醇)或包含官能度为1.8至4(如1.8至2.4或1.9至2.2)的聚酯多元醇的多元醇掺混物反应。这种多元醇或多元醇掺混物的数均分子量(如通过端基分析测定)通常为400至2000,如400至800或450至500。
为制备适用于本文中的液体的氨基甲酸酯改性的二苯基甲烷二异氰酸酯预聚物中的合适的聚酯多元醇包括多元醇(优选可向其中加入三元醇的二元醇)与多元(优选二元)羧酸、相应的羧酸酐和低级醇的多羧酸酯或其混合物的反应产物。多元羧酸可以是脂族的、脂环族的、芳族的和/或杂环的,并且其可以为被取代的(例如被卤素原子)和/或为不饱和的。
合适的多元羧酸的实例包括:琥珀酸、己二酸、辛二酸、壬二酸、癸二酸、邻苯二甲酸、间苯二甲酸、偏苯三甲酸、邻苯二甲酸酐、四氢邻苯二甲酸酐、六氢邻苯二甲酸酐、四氯邻苯二甲酸酐、内亚甲基四氢邻苯二甲酸酐、戊二酸酐、马来酸、马来酸酐、富马酸、二聚和三聚脂肪酸如油酸,其可与单体脂肪酸混合、对苯二甲酸二甲酯和对苯二甲酸双乙二醇酯。
合适的多元醇包括:乙二醇、1,2-丙二醇和1,3-丙二醇、1,3-丁二醇和1,4-丁二醇、1,6-己二醇、1,8-辛二醇、新戊二醇、环己烷二甲醇(1,4-双-(羟甲基)环己烷)、2-甲基-1,3-丙二醇、2,2,4-三甲基-1,3-戊二醇、三甘醇、四甘醇、聚乙二醇、二丙二醇、聚丙二醇、二丁二醇和聚丁二醇、丙三醇和三羟甲基丙烷。
聚酯还可含有一部分羧基端基。还可使用内酯的聚酯,例如ε-己内酯或羟基羧酸(如ω-羟基己酸)。
在一些实施方案中,聚酯多元醇由乙二醇和/或二乙二醇和邻苯二甲酸酐、对苯二甲酸二甲酯或邻苯二甲酸形成。
美国专利号4,644,027中所公开的类型的聚酯多元醇和聚酯多元醇掺混物(其中将疏水化合物掺入到聚酯多元醇中)是合适的。
如文中所示,液体的氨基甲酸酯改性的二苯基甲烷二异氰酸酯预聚物可通过使聚合的二苯基甲烷二异氰酸酯与聚酯多元醇以这样的量反应制备,所述量使得聚合的二苯基甲烷二异氰酸酯中的异氰酸酯基团与聚酯多元醇中的羟基基团的当量比为例如15:1至160:1,如25:1至39:1。该反应通常在约40至约80℃(如50至60℃)的温度下进行例如10至60分钟(如20至40分钟)。
在一些实施方案中,这种液体的氨基甲酸酯改性的二苯基甲烷二异氰酸酯预聚物的NCO官能度为至少2.1(如至少2.3或至少2.5)且小于或等于3.8(如小于或等于3.5或小于或等于3.2)。这种液体的氨基甲酸酯改性的二苯基甲烷二异氰酸酯预聚物的NCO官能度可介于这些上限值和下限值的任意组合之间,包括例如2.1至3.8,如2.3至3.5或2.5至3.2。
在一些实施方案中,这种液体的氨基甲酸酯改性的二苯基甲烷二异氰酸酯预聚物的NCO基团含量为至少25重量%(如至少27.5重量%或至少29重量%)且NCO基团含量小于或等于33重量%(如小于或等于32重量%或小于或等于31重量%)。这种液体的氨基甲酸酯改性的二苯基甲烷二异氰酸酯预聚物的NCO基团含量可介于这些上限值和下限值的任意组合之间,包括例如25重量%至33重量%、27.5重量%至32重量%或29重量%至31重量%。
在一些实施方案中,这种液体的氨基甲酸酯改性的二苯基甲烷二异氰酸酯预聚物的NCO基团含量为27.5%至32%(如29.8至31.2%)、官能度为2.3至3.5(如2.8)且在25℃下的粘度为200至1000mPa·s(如在25℃下235至435mPa·s)。
在其他实施方案中,为制备液体的氨基甲酸酯改性的异氰酸酯封端的预聚物而使用的异氰酸酯反应性组分包含支链的脂族二羟基化合物。例如,在一些实施方案中,液体的氨基甲酸酯改性的异氰酸酯封端的预聚物包含0.1至0.3mol的具有支链碳链的脂族二羟基化合物与1mol的4,4'-二苯基胺二异氰酸酯和/或其2,4'-异构体的反应产物。
为制备这种液体的氨基甲酸酯改性的异氰酸酯封端的预聚物,合适的支链的脂族二羟基化合物包括:例如分子中含有至少两个烷基的1,3-丙二醇,如2-乙基-1,3-己二醇、2-甲基-2,4-戊二醇、2,2,4-三甲基-1,3-戊二醇、3-甲基-5-乙基-2,4-庚二醇、2-甲基-2-丙基-1,3-丙二醇或其中任意两种或更多种的混合物。在某些实施方案中,使用分子量为134至700的聚-1,2-丙二醇醚(poly-1,2propylene ether glycols),如二丙二醇、三丙二醇、聚丙二醇或其中任意两种或更多种的混合物。
这种液体的氨基甲酸酯改性的异氰酸酯封端的预聚物可通过在40至600℃的温度下在搅拌下将支链的脂族二醇引入到二异氰酸酯中来制备,加成反应在最高达800℃的温度下完成。
在某些实施方案中,这种液体的氨基甲酸酯改性的异氰酸酯封端的预聚物——所述方法的产物——的异氰酸酯含量总计15%NCO至25%NCO。纯的结晶二苯基甲烷二异氰酸酯的异氰酸酯含量与所述方法的产物的异氰酸酯含量之差相当于所用的支链的二羟基化合物的量。
在一些实施方案中,这种液体的氨基甲酸酯改性的二苯基甲烷二异氰酸酯预聚物的NCO基团含量为至少15重量%(如至少20重量%或至少22重量%)且NCO基团含量小于或等于25重量%(如小于或等于24重量%或小于或等于23重量%)。这种液体的氨基甲酸酯改性的二苯基甲烷二异氰酸酯预聚物的NCO基团含量可介于这些上限值和下限值的任意组合之间,包括例如15重量%至25重量%、20重量%至24重量%或22重量%至24重量%。
在一些实施方案中,这种液体的氨基甲酸酯改性的二苯基甲烷二异氰酸酯预聚物在25℃下的粘度为300至1000mPa·s,如在25℃下500至1000mPa·s,或在25℃下550至800mPa·s。
如文中所示,本说明书的颗粒的某些实施方案包括涂层,所述涂层包含含有反应混合物的缩合反应产物,所述反应混合物包含异氰酸酯反应性组合物。如本文中所使用的,术语“异氰酸酯反应性组合物”是指包括含有对异氰酸酯基团具有反应性的官能团(如羟基、胺基和硫醇基)的组分(“异氰酸酯官能化组分”)的组合物。
在某些实施方案中,异氰酸酯反应性组合物包含植物油聚酯多元醇。如本文中所使用的,术语“植物油聚酯多元醇”是指通过将活性氢基团引入到植物油上而制备的酯多元醇。应当理解,植物油是脂肪酸混合物(通常含有一些不饱和脂肪酸)的甘油三酯。
适用于本文中的植物油聚酯多元醇可通过任意方法制备。例如,在某些实施方案中,使用两步法,其从植物油的环氧化开始,随后通过打开环氧化的植物油的环氧乙烷来将羟基引入到植物油分子上。这种环氧乙烷环的打开可以以多种方法完成,例如:用蓖麻油酸,如美国专利号2,882,249中所记载;用丙烯酸,如美国专利号4,025,477中所记载;用羧酸,如美国专利号5,266,714和5,302,626中所记载;用酸浸出的粘土,如美国专利号6,891,053中所记载;用(多元)醇,如美国专利号4,508,853、4,742,087、6,433,125、4,551,517和4,886,893中所记载;或用水、醇和氟硼酸的混合物,如美国专利号6,107,433、6,433,121、6,573,354和6,686,435中所记载。
在另一种技术中,如在美国专利申请公开号2009/0292099 A1第[0015]-[0028]段——通过引用并入本文中的所引用的部分——中所记载,在一步法中,通过使具有至少一个亲核官能团(如胺基、硫醇基和膦烷基)和至少一个活性氢基团的反应物与具有至少一个碳碳双键的植物油反应而将植物油中的不饱和位点直接官能化,以得到植物油聚酯多元醇。
适用于制备这种植物油聚酯多元醇的植物油包括例如玉米油、大豆油、菜籽油、向日葵油、芝麻籽油、花生油、红花油、橄榄油、棉籽油、亚麻籽油、核桃油和桐油及其混合物。应当理解,大豆油例如含有约54重量%的亚油酸、23重量%的油酸、10重量%的棕榈酸、8重量%的亚麻酸和5重量%的硬脂酸。平均来看,大豆油每个分子含有4.65个不饱和位点(烯烃基团、碳碳双键)。
在某些实施方案中,植物油聚酯多元醇在25℃下的粘度小于1000mPa·s(如100至1000mPa·s cps或200至500mPa·s)、OH值为175至550(如175至340或200至260)和/或官能度为2至5(如2至4、2至3或2)。
在某些实施方案中,如上所述的植物油聚酯多元醇以至少50重量%(如至少60重量%,如50重量%至90重量%或60重量%至80重量%)的量存在,基于异氰酸酯反应性组合物中存在的异氰酸酯反应性组分的总重量计。
如前所述,在某些实施方案中,异氰酸酯反应性组合物还包含芳族二胺,如在第一氨基的邻位含有至少一个烷基取代基且在第二氨基的邻位含有两个烷基取代基的那些或其混合物。在一些实施方案中,所述烷基取代基中有至少两个含有至少两个碳原子。在某些实施方案中,所述二胺对异氰酸酯的反应性尚未因吸电子取代基(如卤素、酯基、醚基或二硫基)而降低,例如与亚甲基双氯苯胺(MOCA)的情况。在某些实施方案中,这种二胺不含与异氰酸酯反应的其他官能团。在某些实施方案中,前述烷基取代基可具有多达二十个碳原子且可为直链或支链的长链。
在某些实施方案中,芳族二胺在第一氨基的邻位含有至少一个烷基取代基且在第二氨基的邻位含有两个具有1至3个碳原子的烷基取代基,条件是这些烷基取代基中有两个含有两个或三个碳原子。这种芳族二胺的实例包括:1-甲基-3,5-二乙基-2,4-二氨基苯、1-甲基-3,5-二乙基-2,6-二氨基苯、1,3,5-三乙基-2,6-二氨基苯和3,5,3',5'-四乙基-4,4'-二氨基二苯基甲烷。
当然,上述芳族胺可彼此混合使用或与其他活性芳族胺组合使用。
在某些实施方案中,使用在各氨基的两个邻位均具有直链烷基取代基(其具有1至3个碳原子)的芳族二胺,条件是所述烷基取代基中有两个含有两个或三个碳原子。在一些实施方案中,所述二胺在室温下为液体,并且可与多元醇混溶,特别是可与聚醚多元醇混溶。这种化合物的实例是1-甲基-3,5-二乙基-2,4-二氨基苯或该化合物与1-甲基-3,5-二乙基-2,6-二氨基苯的混合物。
在某些实施方案中,芳族胺以5至50重量%(如10至40重量%或在一些情况下25至35重量%)的量存在,基于异氰酸酯反应性组合物中存在的异氰酸酯反应性组分的总重量计。
如文中所示,异氰酸酯反应性组合物可包含用于羟基和异氰酸酯基团之间的反应的催化剂。合适的催化剂包括例如有机锡化合物,如羧酸的锡(II)盐(如乙酸锡(II)、辛酸锡(II)、乙基己酸锡(II)或月桂酸锡(II))和羧酸的二烷基锡盐(如二乙酸二丁基锡、二月桂酸二丁基锡、马来酸二丁基锡或二乙酸二辛基锡),单独地或作为与以下脒的络合物:如2,3-二甲基-3,4,5,6-四氢嘧啶或2-甲基-3-环己基-3,4,5,6-四氢嘧啶、氨基吡啶、氨基嘧啶、肼基吡啶或肼基嘧啶。
可使用的其他催化剂包括叔胺,如三乙胺、三丁胺、N-甲基吗啉、N-乙基吗啉、N-椰纤维烷基吗啉(N-cocomorpholine)、N,N,N',N'-四甲基乙二胺、1,4-二氮杂双环-(2,2,2)-辛烷、N-甲基-N'-二甲基氨基乙基哌嗪、N,N-二甲基苄胺、双-(N,N-二乙基氨基乙基)-己二酸酯、N,N-二乙基苄胺、五甲基二亚乙基三胺、N,N-二甲基环己胺、N,N,N',N'-四甲基-1,3-丁二胺、N,N-二甲基-β-苯乙胺、1,2-二甲基咪唑和2-甲基咪唑。
也可使用具有异氰酸酯反应性氢原子的叔胺,包括例如三乙醇胺、三异丙醇胺、N-甲基二乙醇胺、N-乙基二乙醇胺和N,N-二甲基乙醇胺。这些化合物与环氧烷烃(如环氧丙烷和/或环氧乙烷)的反应产物也是合适的。
还可将如记载于例如德国专利号1,229,290中的具有碳硅键的硅杂胺(silaamine)用作催化剂。实例包括2,2,4-三甲基-2-硅杂吗啉或1,3-二乙基氨基甲基-四甲基-二硅氧烷。
还可将碱性氮化合物(如四烷基氢氧化铵)、碱金属氢氧化物(如氢氧化钠)、碱金属酚盐(如酚钠)和碱金属醇盐(如甲醇钠)用作催化剂。六氢三嗪也是合适的催化剂。
在某些实施方案中,催化剂包含(i)有机锡化合物(如羧酸的二烷基锡盐,如二月桂酸二丁基锡)和(ii)叔胺(如1,4-二氮杂双环-(2,2,2)-辛烷)。在某些实施方案中,(i)与(ii)的相对重量比为20:80至80:20,如40:60至60:40。
在某些实施方案中,催化剂以0.01至10重量%(如0.05至1重量%)的量存在,基于异氰酸酯反应性组合物中异氰酸酯反应性组分的总重量计。
待使用的催化剂应使加聚反应加速至这样的程度,即一旦混合起始组分之后,反应混合物就具有小于15秒、10秒或5秒的流动时间(例如流动能力,因此所述混合物仍然可以被输送的时间)。
在某些实施方案中,液体的异氰酸酯官能化组分和异氰酸酯反应性组合物各自以这样的量使用,使得反应混合物的NCO指数(即,存在的反应性异氰酸酯基团的总数与可与该异氰酸酯反应的异氰酸酯反应性基团的总数之比乘以100)为至少120(如至少140或至少180)且不大于500(如不大于400或在一些情况下不大于300或不大于250)。NCO指数可介于这些上限值和下限值的任意组合之间,包括例如120至500、140至500、180至400、180至300或例如180至250。
可使用其他成分以形成本说明书的涂覆的颗粒。例如,在某些实施方案中,使用具有下式的氨基硅烷偶联剂:
其中:(A)每个X(其可以相同或不同)为在100℃下对异氰酸酯基团呈惰性的有机基团,条件是这些基团中的至少一个为烷氧基或酰氧基,如其中每个X为具有1至4个碳原子的烷基或烷氧基,如其中每个X为具有2个碳原子的烷氧基;(B)Y为含有1至8个碳原子的直链或支链的亚烷基基团,如含有2至4个碳原子的直链基团或含有5至6个碳原子的支链基团,如含有3个碳原子的直链基团;且(C)R1为在100℃或更低的温度下对异氰酸酯基团呈惰性的氢或有机基团,如烷基、环烷基或具有1至12个碳原子的芳族基团;或R1代表对应于下式的基团:
–Y–Si–(X)3
其中X和Y具有上述相同的含义。
在某些实施方案中,每个X代表甲氧基、乙氧基或丙氧基,Y为含有3个碳原子的直链亚烷基(即亚丙基),且R1为氢。
在某些实施方案中,氨基硅烷以0.1至10重量%(如1至5重量%或在一些情况下2至4重量%)的量使用,基于异氰酸酯反应性组合物的总重量计。
也可使用表面活性添加剂。实例包括蓖麻油磺酸盐的钠盐或脂肪酸的钠盐;或脂肪酸与胺的盐(如油酸二乙胺或硬脂酸二乙醇胺);磺酸(如十二烷基苯磺酸或二萘基甲烷二磺酸)或脂肪酸(如蓖麻油酸)或聚合的脂肪酸的碱金属盐或铵盐;以及具有连接到环氧乙烷和环氧丙烷的共聚物的聚二甲基硅氧烷基团的水溶性聚醚硅氧烷。
还可使用颜料、染料、阻燃剂、抗老化和风化的稳定剂、增塑剂、抑真菌物质和抑细菌物质以及填料。
在某些实施方案中,本说明书的涂覆的颗粒包括涂层,所述涂层包含解晶温度为至少35℃的结晶或半结晶的聚酯/聚氨酯。
事实上,出人意料地发现,可通过在所述涂层中包含仅仅少量(如下所述)的这种结晶或半结晶的聚酯/聚氨酯,能够显著地提高本说明书的涂覆的颗粒支撑剂的UCS保留率%(如实施例中所述的测量)。结果是,本说明书的涂覆的颗粒的一些实施方案包括:(a)粒径不大于3目的基质颗粒;和(b)置于至少一部分颗粒上的涂层,其中所述涂层包含(1)包含以下物质的反应混合物的缩合反应产物:(i)液体的异氰酸酯官能化组分,如上述那些中的任一种;和(ii)包含以下物质的异氰酸酯反应性组合物:(A)多元醇,如聚醚多元醇和/或聚酯多元醇(如上述植物油聚酯多元醇);(B)芳族二胺;(C)用于羟基和异氰酸酯基团之间的反应的催化剂;和(2)解晶温度为至少35℃的结晶或半结晶的聚酯/聚氨酯。
如本文中所使用的,术语“结晶或半结晶的”意指聚酯/聚氨酯的结晶度为5至100%(如20至100%)。如本文中所使用的,“结晶的”意指,在聚合物的DSC中,随着温度升高,通过了一个最大值,这是由于聚合物中的规则的亚结构的熔化造成的。本文中将该最大值出现时的温度称为“解晶温度”。在通过熔融结晶循环的情况下,可从结晶峰的熔融面积确定熔融焓。在某些实施方案中,本文中使用的聚酯/聚氨酯的熔融焓为至少5J/g如至少20J/g,或在一些情况下至少40J/g。
如本文中所使用的,术语“聚酯/聚氨酯”是指在聚合物主链中含有多个酯键和多个氨基甲酸酯基的聚合物。如本文中所使用的,“聚氨酯”还包括聚氨酯脲(其除氨基甲酸酯基外,还含有脲基团)。
在某些实施方案中,结晶或半结晶的聚酯/聚氨酯的解晶温度为至少35℃(如至少40℃、至少42℃或在一些情况下至少45℃)和/或不大于100℃、不大于60℃或在一些情况下不大于52℃。
在某些实施方案中,当根据DIN 65467以10K/min的升温速率通过DSC法测量时,结晶或半结晶的聚酯/聚氨酯的玻璃化转变温度为至少-100℃(如至少-60℃)和/或不大于-10℃(如不大于-40℃)。
在某些实施方案中,结晶或半结晶的聚酯/聚氨酯的重均分子量(Mw)为至少20000g/摩尔(如至少30 000g/摩尔或在一些情况下至少50 000g/摩尔)和/或不大于250000g/摩尔(如不大于220 000g/摩尔或在一些情况下不大于200 000g/摩尔)。如本文中所使用的,聚合物的分子量通过以二甲基乙酰胺为流动相的凝胶渗透色谱法(GPC/SEC)测定。
在某些实施方案中,结晶或半结晶的聚酯/聚氨酯包含反应混合物的反应产物,所述反应混合物包含:(a)数均分子量为400至5 000g/摩尔且包含聚酯多元醇的二官能或多官能化聚合的多元醇;和(b)二官能或多官能化异氰酸酯组分。此外,在一些实施方案中,聚酯/聚氨酯可存在(即,溶解或分散)于沉积在基质颗粒上的基于有机溶剂的组合物或水性组合物中。如本文中所使用的,术语“水性组合物”是指其中尽管不排除存在一些挥发性的有机化合物,但用于聚酯/聚氨酯的载体流体主要包含水的组合物。在水性组合物的某些实施方案中,水以至少80重量%(如至少90重量%、至少95重量%或在一些情况下至少98重量%或至少99重量%)的量存在,基于载体流体的总重量计。如本文中所使用的,术语“基于有机溶剂的组合物”是指其中尽管不排除存在一些水,但用于聚酯/聚氨酯的载体流体主要包含挥发性有机化合物的组合物。在基于有机溶剂的组合物的某些实施方案中,挥发性有机化合物以至少80重量%(如至少90重量%、至少95重量%或在一些情况下至少98重量%或至少99重量%)的量存在,基于载体流体的总重量计。
在某些实施方案中,这样选择各组分的比例,使得沉积在基质颗粒上的包含结晶或半结晶的聚酯/聚氨酯的组合物中的聚合物含量为30至60重量%,基于组合物的总重量计。在这些实施方案中的一些实施方案,沉积在基质颗粒上的组合物在25℃下还具有20至2000cps(如40至1 000cps或在一些情况下50至600cps)的粘度。
如文中所示,某些实施方案的结晶或半结晶的聚酯/聚氨酯包含以下反应物的反应产物,所述反应物包含:(a)数均分子量为400至6 000g/摩尔(如400至5 000g/摩尔、800至3 000g/摩尔或在一些情况下800至2 500g/摩尔或1 500至2 500g/摩尔)的二官能或多官能化聚合的多元醇;并且它包含聚酯多元醇。如本文中所使用的,“多官能化”意指每个分子包括三个或更多个所述官能团的组分,如在多元醇的情况下,分子中包含至少三个羟基(如分子中三个或四个羟基)的组分;和在异氰酸酯的情况下,分子中包含至少三个异氰酸酯基团(如分子中三个或四个异氰酸酯基团)的组分。在一些情况下,数均分子量为400至6000g/摩尔的二官能或多官能化聚合的多元醇的羟基当量为200至3 000g/摩尔(如400至1500g/摩尔或在一些情况下400至1 250g/摩尔或750至1 250g/摩尔)。
适用于这种组分(a)中的聚酯多元醇包括例如直链的聚酯二元醇和支链的聚酯多元醇。合适的聚酯二元醇和聚酯多元醇包括可由脂族、脂环族和/或芳族二元羧酸或多元羧酸与多元醇制备的那些,所述羧酸为:如丁二酸、甲基丁二酸、戊二酸、己二酸、庚二酸、辛二酸、壬二酸、癸二酸、壬烷二羧酸、癸烷二羧酸、对苯二甲酸、间苯二甲酸、邻苯二甲酸、四氢苯二甲酸、六氢苯二甲酸、环己烷二羧酸、马来酸、富马酸、丙二酸和/或偏苯三酸,和酸酐如邻苯二甲酸酐、偏苯三酸酐和/或琥珀酸酐;所述多元醇为:如乙二醇、二乙二醇、三乙二醇或四乙二醇、1,2-丙二醇、二丙二醇、三丙二醇或四丙二醇、1,3-丙二醇、1,4-丁二醇、1,3-丁二醇、2,3-丁二醇、1,5-戊二醇、1,6-己二醇、2,2-二甲基-1,3-丙二醇(新戊二醇)、1,4-二羟基环己烷、1,4-二羟甲基环己烷、1,8-辛二醇、1,10-癸二醇和/或1,12-十二烷二醇,任选地另外使用的更高官能度的多元醇,如三羟甲基丙烷、丙三醇和/或季戊四醇。可用于制备聚酯二元醇和聚酯多元醇的多元醇还包括脂环族和/或芳族二羟基化合物和多羟基化合物。
合适的聚酯多元醇还可为内酯的均聚物或共聚物,其例如通过将内酯或内酯混合物(如丁内酯、ε-己内酯和/或甲基-ε-己内酯)添加到合适的二官能的和/或更高官能度的起始剂分子(例如上述低分子量多元醇)上获得。
在某些实施方案中,二官能或多官能化聚酯多元醇包含以下反应物的反应产物,所述反应物包含己二酸以及1,4-丁二醇、1,6-己二醇和新戊二醇中的一种或多种。
在某些实施方案中,二官能或多官能化聚酯多元醇包含含有二羧酸的反应物的反应产物,所述二羧酸包含丁二酸、己二酸、十二烷二酸、其衍生物和/或其混合物,所述二羧酸以至少80摩尔%、至少85摩尔%或在一些情况下至少90摩尔%的量使用,基于用于制备聚酯多元醇的所有羧酸的总量计。在某些实施方案中,二官能或多官能化聚酯多元醇包含含有二羧酸的反应物的反应产物,所述二羧酸包含戊二酸、壬二酸、1,4-环己烷二羧酸、1,3-环己烷二羧酸和/或1,2-环己烷二羧酸、对苯二甲酸、间苯二甲酸、其衍生物和/或其混合物,所述二羧酸以最高达20摩尔%(如最高达15摩尔%或在一些情况下最高达10摩尔%)的量使用,基于用于制备聚酯多元醇的所有羧酸的总量计。在某些实施方案中,二官能或多官能化聚酯多元醇包含含有多元醇的反应物的反应产物,所述多元醇包含单乙二醇、1,3-丙二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇、新戊二醇和/或其混合物,所述多元醇以至少80摩尔%、至少85摩尔%或在一些情况下至少90摩尔%的量使用,基于用于制备聚酯多元醇的所有多元醇的总量计。在某些实施方案中,二官能或多官能化聚酯多元醇包含含有多元醇的反应物的反应产物,所述多元醇包含二乙二醇、羟基新戊酸新戊二醇、环己烷二甲醇、戊烷-1,2-二醇、壬烷-1,9-二醇、三羟甲基丙烷、丙三醇、季戊四醇和/或其混合物,所述多元醇以最高达20摩尔%(如最高达10摩尔%)的量使用,基于用于制备聚酯多元醇的所有多元醇的总量计。
在某些实施方案中,二官能或多官能化聚酯多元醇包含:(i)至少50重量%(如60至100重量%、70至100重量%、80至100重量%或在一些情况下90至99重量%)的聚酯多元醇,基于组合物中存在的二官能或多官能化聚酯多元醇的总重量计,所述聚酯多元醇包含以下反应物的反应产物,所述反应物包含:(a)己二酸(以至少80摩尔%、至少85摩尔%或在一些情况下至少90摩尔%的量使用,基于用于制备聚酯多元醇的所有羧酸的总量计);和(b)1,4-丁二醇(以至少80摩尔%、至少85摩尔%或在一些情况下至少90摩尔%的量使用,基于用于制备聚酯多元醇的所有多元醇的总量计);和(ii)最高达50重量%(如最高达40重量%、最高达30重量%、最高达20重量%或1至10重量%)的聚酯多元醇,基于组合物中存在的二官能或多官能化聚酯多元醇的总重量计,所述聚酯多元醇包含以下反应物的反应产物,所述反应物包含:(a)己二酸(以至少80摩尔%、至少85摩尔或在一些情况下至少90摩尔%的量使用,基于用于制备聚酯多元醇的所有羧酸的总量计);(b)1,6-己二醇(以至少40摩尔%如40至80摩尔%或在一些情况下50至70摩尔%的量使用,基于用于制备聚酯多元醇的所有多元醇的总量计);(c)新戊二醇(以最高达60摩尔%如20至60摩尔%或在一些情况下30至50摩尔%的量使用,基于用于制备聚酯多元醇的所有多元醇的总量计)。
在一些实施方案中,除聚酯多元醇外,这种组分(a)还可包括最高达50重量%(如最高达40重量%或在一些情况下最高达30重量%)(基于组分(a)的总重量计)的不同于所述聚酯多元醇的二官能或多官能化聚合的多元醇,例如聚醚多元醇和/或聚碳酸酯多元醇。然而,在一些实施方案中,聚酯/聚氨酯基本上不含聚醚单元,或在一些情况下完全不含聚醚单元。
如文中所示,结晶或半结晶的聚酯/聚氨酯包含以下反应物的反应产物,所述反应物包含(b)二官能或多官能化异氰酸酯组分。可以使用每个分子中具有至少两个游离异氰酸酯基团的任何所需的有机化合物,包括例如根据结构Y(NCO)2的二异氰酸酯,其中Y为具有4至12个碳原子的二价脂族烃基、具有6至15个碳原子的二价脂环族烃基、具有6至15个碳原子的二价芳族烃基或具有7至15个碳原子的二价芳脂族烃基。这种二异氰酸酯的具体的但非限制性的实例为四亚甲基二异氰酸酯、甲基五亚甲基二异氰酸酯、六亚甲基二异氰酸酯(“HDI”)、十二亚甲基二异氰酸酯、1,4-二异氰酸基环己烷、1-异氰酸基-3,3,5-三甲基-5-异氰酸基甲基环己烷(“IPDI”)、4,4'-二异氰酸基二环己基甲烷、4,4'-二异氰酸基-2,2-二环己基丙烷、1,4-二异氰酸基苯、2,4-二异氰酸基甲苯、2,6-二异氰酸基甲苯、4,4'-二异氰酸基二苯基甲烷、2,2'-二异氰酸基二苯基甲烷和2,4'-二异氰酸基二苯基甲烷、四甲基亚二甲苯基二异氰酸酯、对亚二甲苯基二异氰酸酯、对异亚丙基二异氰酸酯以及这些化合物中的两种或更多种的混合物。
具有例如碳二亚胺基、脲基甲酸酯基、脲二酮基、异氰脲酸酯基、氨基甲酸酯基和/或缩二脲基的更高官能度的多异氰酸酯或改性的多异氰酸酯也是合适的。
在一些实施方案中,二异氰酸酯包含脂族和/或芳脂族的二异氰酸酯,如HDI、1,4-二异氰酸基环己烷、1-异氰酸基-3,3,5-三甲基-5-异氰酸基甲基环己烷、4,4'-二异氰酸基二环己基甲烷和/或4,4'-二异氰酸基-2,2-二环己基丙烷。
在某些实施方案中,结晶或半结晶的聚酯/聚氨酯包含含硅烷的聚酯/聚氨酯。因此,在一些实施方案中,结晶或半结晶的聚酯/聚氨酯为还包含(c)烷氧基硅烷的反应物的反应产物,所述烷氧基硅烷包含异氰酸酯基团或异氰酸酯反应性基团如硫醇基和/或胺基(aminic group),这取决于制备所述聚酯/聚氨酯的方法。如本文中所使用的,“烷氧基硅烷”意指包含硅原子、烷氧基和另一有机基团的化合物,其中硅原子通过共价键与有机基团键合。
例如,可通过使多元醇与包含异氰酸酯基团的烷氧基硅烷反应来制备含硅烷的聚酯/聚氨酯,所述多元醇如聚合的多元醇(a)或通过使聚合的多元醇(a)与不足的异氰酸酯组分(b)反应而制备的OH官能化预聚物。适于使用的这种烷氧基硅烷的实例包括例如异氰酸酯官能化二烷氧基硅烷和三烷氧基硅烷,如异氰酸基甲基三甲氧基硅烷、异氰酸基甲基三乙氧基硅烷、(异氰酸基甲基)甲基二甲氧基硅烷、(异氰酸基甲基)甲基二乙氧基硅烷、3-异氰酸基丙基三甲氧基硅烷、3-异氰酸基丙基甲基二甲氧基硅烷、3-异氰酸基丙基三乙氧基硅烷和3-异氰酸基丙基甲基二乙氧基硅烷。
在用于制备含硅烷的聚酯/聚氨酯的该实施方案中,可通过使聚合的多元醇(a)与不足的异氰酸酯组分(b)反应来制备OH官能化预聚物,其中使用NCO:OH比率为1:1.3至1:10(如1:1.5至1:3)。
OH官能化预聚物的制备和所述预聚物与包含异氰酸酯基团的烷氧基硅烷的反应均可通过合适的催化作用加速。为加速NCO-OH反应,催化剂如有机锡化合物或胺催化剂是合适的。其中所掺入的催化剂通常以0.001至5.0重量%(如0.001至0.1重量%和在一些情况下0.005至0.05重量%)的量使用,基于该方法产物的固含量计。
反应通常在20至200℃(如40至120℃或在一些情况下60至100℃)的温度下进行。可继续反应直至含异氰酸酯化合物的NCO基团实现完全转化。可通过安装在反应容器中的合适的测量仪器和/或通过分析所取样品来监测反应进程。适当的方法包括粘度测量、NCO含量的测量、折射率的测量和OH含量的测量、气相色谱(GC)、核磁共振(NMR)光谱、红外(IR)光谱和近红外(NIR)光谱。混合物的NCO含量通常通过滴定法测定。
所述方法可例如在静态混合器、挤出机或捏合机中连续进行或例如在搅拌反应器中分批进行。
用于制备结晶或半结晶的含硅烷的聚酯/聚氨酯的另一种方法是使异氰酸酯组分(b)或NCO官能化预聚物(通过使聚合的多元醇(a)与过量的异氰酸酯组分(b)反应制备)与包含异氰酸酯反应性基团(如胺基或硫醇基)的烷氧基硅烷反应。在某些实施方案中,对于在制备这种NCO官能化预聚物的反应中的组分的量进行选择,以得到NCO:OH比率为1.3:1.0至2:1(如1.5:1.0至2:1)。与第一种方法一样,该氨基甲酸酯化反应也可通过催化作用加速;反应的温度范围也是类似的。
在该实施方案中,继续进行反应直至多元醇的OH实现完全转化。反应进程可通过检测NCO含量来监测,并且当达到适当的理论NCO含量时,反应完全。这随后可通过安装在反应容器中的合适的测量仪器和/或通过分析所取样品进行。适当的方法:粘度测量、NCO含量的测量、折射率的测量和OH含量的测量、GC、NMR光谱、IR光谱和NIR光谱。混合物的NCO含量通常通过滴定法测定。
在这些方法中,使异氰酸酯组分(b)和/或NCO官能化预聚物与呈异氰酸酯反应性的烷氧基硅烷反应,如呈异氰酸酯反应性的二烷氧基硅烷和/或三烷氧基硅烷,包含例如胺官能化烷氧基硅烷和/或硫醇官能化烷氧基硅烷,其实例包括但不限于单硅烷和双硅烷,其具体实例包括但不限于:N(β-氨基乙基)、γ-氨基丙基三甲氧基硅烷、双(三甲氧基甲硅烷基丙基)胺、氨丙基三甲氧基硅烷、巯丙基三甲氧基硅烷、丙基甲基二甲氧基硅烷、巯丙基甲基二甲氧基硅烷、氨丙基三乙氧基硅烷、巯丙基三乙氧基硅烷、氨丙基甲基二乙氧基硅烷、巯丙基甲基二乙氧基硅烷、氨甲基三甲氧基硅烷、氨甲基三乙氧基硅烷、(氨甲基)甲基二甲氧基硅烷、(氨甲基)甲基二乙氧基硅烷、N-丁基氨基丙基三甲氧基硅烷和/或N-苯基氨基丙基三甲氧基硅烷。
在某些实施方案中,组分(c)的用量为0.1至10重量%(如0.2至2重量%或在一些情况下0.5至1.5重量%),基于为制备聚酯/聚氨酯而使用的反应物的总重量计。
在某些实施方案中,结晶或半结晶的聚酯/聚氨酯包含以下反应物的反应产物,所述反应物还包含(d)分子量为62至399g/摩尔的二官能或多官能化多元醇。组分(d)的实例为聚合物,如聚醚、聚酯、聚碳酸酯、聚内酯和/或聚酰胺。还适合用作组分(d)的为较早地关于聚酯多元醇的制备中提及的多元醇(包括二元醇),并且包括例如单体多元醇,如乙二醇、二乙二醇、1,2-丙二醇、二丙二醇、1,3-丙二醇、1,4-丁二醇、1,3-丁二醇、2,3-丁二醇、1,5-戊二醇和1,6-己二醇。
在某些实施方案中,组分(d)的用量为0.1至10重量%(如0.1至2重量%或在一些情况下0.1至1重量%),基于为制备聚酯/聚氨酯而使用的反应物的总重量计。
在某些实施方案中,特别是其中寻求使结晶或半结晶的聚酯/聚氨酯以水性组合物中的稳定分散体而存在的那些实施方案,结晶或半结晶的聚酯/聚氨酯包含以下反应物的反应产物,所述反应物还包含(e)含有离子基团或潜在的离子基团的分散剂化合物,其本质上是阳离子的或阴离子的,并且具有至少一个异氰酸酯反应性基团如羟基、硫醇基和/或胺基。合适的阳离子基团和阴离子基团包括例如锍基、铵基、鏻基、羧酸根、磺酸根、膦酸根或可通过去质子化(即形成盐)转化成这些基团的相应的非离子酸基(即潜在的离子基团)。
合适的离子化合物或潜在的离子化合物包括例如单羟基羧酸和二羟基羧酸、单氨基羧酸和二氨基羧酸、单羟基磺酸和二羟基磺酸、单氨基磺酸和二氨基磺酸、单羟基膦酸和二羟基膦酸、单氨基膦酸和二氨基膦酸;及其盐;包括其组合。合适的具体化合物的实例包括但不限于二羟甲基丙酸、二羟甲基丁酸、羟基新戊酸、N-(2-氨基乙基)-对丙氨酸、2-(2-氨基乙基氨基)乙磺酸、乙二胺丙基磺酸或乙二胺丁基磺酸、1,2-或1,3-丙二胺-β-乙基磺酸、柠檬酸、乙醇酸、乳酸、甘氨酸、丙氨酸、牛磺酸、赖氨酸、3,5-二氨基苯甲酸、IPDI与丙烯酸及其碱金属盐和/或铵盐的加合物、亚硫酸氢钠与丁-2-烯-1,4-二醇的加合物、聚醚磺酸盐以及2-丁烯二醇和NaHSC3的丙氧基化加合物。
适合用于组分(e)中的化合物还包括其他2,2-双(羟甲基)烷烃羧酸,如二羟甲基乙酸和2,2-二羟甲基戊酸、二羟基琥珀酸、丙烯酸与胺(如异佛尔酮二胺或己二胺)的迈克尔加合物或这种酸和/或二羟甲基丙酸和/或羟基新戊酸的混合物、任选地包含醚基的磺酸二醇,例如记载于美国专利号4,108,814中第3列第13行至第5列第2行中的化合物,其引用的部分通过引用并入本文中。
对异氰酸酯基团具有反应性的分散剂化合物可含有亲水性醚基,该亲水性醚基使共价结合所述分散剂化合物的大分子具有水分散性。合适的化合物包括例如聚醚多元醇和聚醚多胺。示例性的化合物包括但不限于醇衍生的聚乙二醇、聚丙二醇、其共聚物及其单甲醚。
适合用于含有磺酸根或羧酸根的组分(e)中的化合物为例如具有磺酸根和/或羧酸根的二氨基化合物或二羟基化合物,例如以下化合物的钠盐、锂盐、钾盐和叔胺盐:N-(2-氨基乙基)-2-氨基乙磺酸、N-(3-氨基丙基)-2-氨基乙磺酸、N-(3-氨基丙基)-3-氨基丙磺酸、N-(2-氨基乙基)-3-氨基丙磺酸、类似的羧酸、二羟甲基丙酸、二羟甲基丁酸或1摩尔二胺(例如1,2-乙二胺或异佛尔酮二胺)与2摩尔丙烯酸或马来酸的迈克尔加成反应产物。
酸通常以其盐的形式作为磺酸盐或羧酸盐而直接使用。然而,也可在聚氨酯的制备期间或之后首先加入形成盐所需的一部分或全部的中和剂。适于形成盐的叔胺为例如三乙胺、二甲基环己胺和/或乙基二异丙胺。其他胺也可用于形成盐,例如氨、二乙醇胺、三乙醇胺、二甲基乙醇胺、甲基二乙醇胺、氨基甲基丙醇及其混合物。通常仅在异氰酸酯基团已经大量反应之后才加入这些胺。也可使用其他中和剂,例如氢氧化钠、氢氧化钾、氢氧化锂或氢氧化钙。
在某些实施方案中,组分(e)的用量为0重量%至20重量%(如0.1重量%至20重量%、0.5重量%至20重量%或在一些情况下1重量%至15重量%),基于为制备聚酯/聚氨酯而使用的反应物的总重量计。
在某些实施方案中,结晶或半结晶的聚酯/聚氨酯包含还含有组分(f)的反应物的反应产物,所述组分(f)包含胺扩链剂,如单氨基化合物和/或二氨基化合物。在本发明上下文中,扩链剂还包括导致链终止的单胺及其混合物。
合适的单胺扩链剂的实例为脂族和/或脂环族的伯单胺和/或仲单胺,如乙胺、二乙胺、异构的丙胺和丁胺、高级直链脂族单胺和脂环族单胺如环己胺。其他实例为氨基醇,即在一个分子中含有氨基和羟基的化合物,例如乙醇胺、N-甲基乙醇胺、二乙醇胺或2-丙醇胺。其他实例为可另外带有磺酸基和/或羧酸基的单氨基化合物,例如牛磺酸、甘氨酸或丙氨酸。
合适的二氨基扩链剂的实例为1,2-乙二胺、1,6-己二胺、1-氨基-3,3,5-三甲基-5-氨基甲基环己烷(异佛尔酮二胺)、哌嗪、1,4-二氨基环己烷或双(4-氨基环己基)甲烷。此外,己二酸二酰肼、肼或水合肼也是有用的。还可使用多胺如二亚乙基三胺代替二氨基化合物作为形成组分。
在某些实施方案中,组分(f)的用量0.1至10重量%(如0.1至2重量%或在一些情况下0.1至1重量%),基于为制备聚酯/聚氨酯而使用的反应物的总重量计。
在某些实施方案中,结晶或半结晶的聚酯/聚氨酯包含还含有组分(g)的反应物的反应产物,所述组分(g)包含其他异氰酸酯反应性化合物,如具有2至22个碳原子的脂族、脂环族或芳族的单醇,如乙醇、丁醇、己醇、环己醇、异丁醇、苄醇、硬脂醇和2-乙基乙醇;基于起始于醇或胺的环氧乙烷聚合物或环氧乙烷/环氧丙烷共聚物且具有亲水作用的单官能或二官能化聚醚;常用于异氰酸酯基团且可在高温下再次分离的封闭剂,如丁酮肟、二甲基吡唑、己内酰胺、丙二酸酯、三唑、二甲基三唑、叔丁基苄胺和环戊酮羧乙基酯;和含有可用于聚合反应的基团的不饱和化合物,如丙烯酸羟乙酯、甲基丙烯酸羟乙酯、丙烯酸羟丁酯、甲基丙烯酸羟丁酯、丙烯酸羟丙酯、甲基丙烯酸羟丙酯、季戊四醇三丙烯酸酯;以及单环氧化物、双环氧化物和/或多环氧化物与(甲基)丙烯酸的羟基官能化反应产物。
在一些实施方案中,(a)至(g)或其任意子集的重量百分比之和(如(a)至(f)之和)总计100%。
结晶或半结晶的聚酯/聚氨酯可通过任意方法制备,所述方法如乳化剂/剪切力法、丙酮法、预聚物混合法、熔体乳化法、酰亚酮法和自发的固体分散法,如在Methoden derOrganischen Chemie,Houben-Weyl,第4版,第E20卷/第2部分,第1682页,Georg ThiemeVerlag,Stuttgart,1987中所记载。
在一些实施方案中,如其中提供的聚酯/聚氨酯作为水性组合物中的稳定分散体的那些实施方案,使用丙酮法制备所述聚酯/聚氨酯。为此,将组分A和B的预聚物以及(如果合适)C、D、E和/或G中的任一种溶解在丙酮中,并使用组分F扩链。在用水分散后,蒸馏出丙酮。丙酮法记载于美国专利号3,479,310和GB 1,076,788中。其他适于制备聚合的水分散体的方法记载于DE-OS 2 725 589以及美国专利号4,269,748、4,192,937、4,292,226和3,756,992中。
如文中所示,出人意料地发现,通过在所述涂层中包含仅少量的(如下所述)这种结晶或半结晶的聚酯/聚氨酯,能够显著地提高本说明书的涂覆的颗粒支撑剂的UCS保留率%(如实施例中所述的测量)。因此,在某些实施方案中,这种结晶或半结晶的聚酯/聚氨酯的用量仅为0.01至1重量%(如0.01至0.5重量%、0.1至0.5重量%、0.1至0.4重量%或0.2至0.4重量%),基于涂覆的颗粒的总重量计。
本说明书的涂覆的颗粒还可包括固体颗粒抗结块剂。抗结块剂是这样的材料,当以有效量存在时,可防止本说明书的涂覆的颗粒结块或聚集,从而使得能够产生自由流动且可倾倒的颗粒。
合适的固体抗结块剂包括例如二氧化硅如热解法二氧化硅、有机膨润土、氢化蓖麻油和聚酰胺。在某些实施方案中,当用裸眼观察时,抗结块剂不赋予涂层任何颜色,因此不用作着色剂。
在某些实施方案中,固体颗粒抗结块剂的平均粒径为至少0.1微米(如至少0.5微米)且不大于10微米(如不大于5微米)。
在某些实施方案中,为制备自由流动的可倾倒的颗粒,固体颗粒抗结块剂以有效的量使用。在某些实施方案中,固体颗粒抗结块剂(如热解法二氧化硅)以至少0.1重量%(如0.1至1重量%或在一些情况下0.1至0.4重量%)的量存在,基于涂覆的颗粒的总重量计。
本说明书的实施方案涉及制备自由流动的颗粒的方法。在一些实施方案中,本文中记载的涂覆的颗粒通过首先干燥基质颗粒制备,如通过例如将基质颗粒加热至例如至少50℃(如至少80℃或至少90℃)的温度。如果需要,可将如上所述的氨基硅烷加入到干燥的基质颗粒中,优选在混合的同时加入。然后将异氰酸酯反应性组合物在混合的同时加入到基质颗粒中,随后加入异氰酸酯官能化组分,并允许进行缩合反应,随后加入结晶或半结晶的聚酯/聚氨酯的水分散体(如果使用)。最后,将由此制备的涂覆的颗粒与固体颗粒抗结块剂混合。
在某些实施方案中,反应混合物以至少0.1重量%(如至少1重量%或至少2重量%)且最高达10重量%、最高达5重量%或在一些情况下最高达4重量%的量存在,基于基质颗粒的总重量计。反应混合物可以介于这些上限值和下限值的任意组合之间的任意量存在,包括例如0.1至10重量%、1重量%至5重量%、2重量%至5重量%或2重量%至4重量%,基于存在的基质颗粒的总重量计。
出人意料地,还发现多步骤涂覆法可显著地提高本说明书的涂覆的颗粒支撑剂的UCS保留率%(如实施例中所述的测量)。根据该方法,首先干燥基质颗粒,如通过例如将基质颗粒加热至例如至少50℃(如至少80℃或至少90℃)的温度。如果需要,可将如上所述的氨基硅烷加入到干燥的基质颗粒中,优选在混合的同时加入。然后,在混合的同时将一部分异氰酸酯反应性组合物(如最高达待使用的总量的50重量%)加入到基质颗粒中,随后加入一部分异氰酸酯官能化组分,并允许进行缩合反应。其后,分一个或更多个另外的步骤加入剩余部分的异氰酸酯反应性组合物和异氰酸酯官能化组分,随后加入结晶或半结晶的聚酯/聚氨酯的水分散体(如果使用)。最后,将由此制备的涂覆的颗粒与固体颗粒抗结块剂混合。
因此,应当理解,本说明书还涉及用于制备涂覆的颗粒的方法,其包括:(1)将粒径不大于3目的基质颗粒(如上述那些基质颗粒中的任一种)与第一部分异氰酸酯反应性组合物(如上述异氰酸酯反应性组合物中的任一种)和第一部分液体的异氰酸酯官能化组分(如上述液体的异氰酸酯官能化组分中的任一种)混合;(2)允许所述第一部分异氰酸酯反应性组合物和所述第一部分液体的异氰酸酯官能化组分之间的缩合反应发生,以形成涂覆的颗粒;然后(3)分一个或更多个另外的步骤将由此制备的涂覆的颗粒与第二(和任选地第三)部分异氰酸酯反应性组合物和第二(和任选地第三)部分异氰酸酯官能化组分混合,其中允许每份随后加入的那部分的异氰酸酯反应性组合物与每份随后加入的那部分的液体的异氰酸酯化官能组分之间的缩合反应发生,然后再加入另一部分的异氰酸酯反应性组合物和另一部分的液体的异氰酸酯官能化组分。如上所述,可加入另外的组分,如偶联剂、结晶或半结晶的聚酯/聚氨酯和/或固体颗粒抗结块剂。
本文中记载的涂覆的颗粒可用于多种应用中。然而,在某些实施方案中,本说明书的涂覆的颗粒也被认为适合用于水力压裂地质层。在这些实施方案中,可将涂覆的颗粒与载体流体(如水和/或烃)合并,并将混合物在高压下注入到至地下地质层的井眼中。当注入导致地层中的压力超过地层的强度时,会形成裂缝,且涂覆的颗粒(即支撑剂)被置于地层中,以在释放注入压力时将裂缝维持在支撑状态。在停止注入流体时,期望所述支撑剂形成用于保持裂缝张开的填塞物(pack),从而提供高传导性的通道,所需材料如水、油或气(包括天然气)可通过该通道流至井眼取回。
因此,在某些实施方案中,将涂覆的颗粒用于形成支撑剂组合物的方法中,所述方法包括:将本文中描述的涂覆的颗粒悬浮于载体流体中以形成悬浮液,并将该悬浮液注入到地下地质层中。
可将本文中描述的涂覆的颗粒作为单独的支撑剂或作为现有支撑剂的部分替代物注入。例如,如果需要,本文中描述的涂覆的颗粒可以占1至99重量%(如10至90重量%或在一些情况下10至50重量%),基于注入到井眼中的组合物中存在的支撑剂的总重量计。在一些实施方案中,首先将未涂覆的支撑剂置于井中,其后将本文中描述的涂覆的颗粒的支撑剂置于最接近于井眼或裂缝开口的裂缝中。
目前认为本说明书的涂覆的颗粒具有若干优点,特别是在水力压裂法的情况下。例如,如本文中所述制备的涂覆的颗粒的特征在于非常高的UCS和良好的贮存稳定性,即如实施例中所述随时间变化保持UCS的能力。
以下非限制性且非穷举性的实施例旨在进一步描述各种非限制性且非穷举性的实施方案,而不限制本说明书中描述的实施方案的范围。
实施例
实施例1-8
除非另有说明,否则所有以“份数”和“百分比”给出的量均应理解为以重量计。在实施例的制剂中使用以下材料:
涂覆的颗粒的制备:
使用表1中列出的成分和量(以份计)制备涂覆的沙粒。
表1
1 20/40(20-40目)沙子
2 γ-氨基丙基三乙氧基硅烷, 从Momentive Performance Materials市售获得
3 70重量份的Honey BeeTM Polyol HB-230(衍生自羟基官能度为~2且羟基值为220-240mg KOH/gm的大豆油的聚酯多元醇,并且具有参照美国专利号8,828,269中图4所描述的结构)、30重量份的1-甲基-3,5-二乙基-2,4-二氨基苯、0.1重量份的33-LV(从Sigma-Aldrich市售获得的胺催化剂)、0.1重量份的T-12(从Evonik市售获得的二月桂酸二丁基锡)和0.1重量份的X17AB(从Milliken Chemical市售获得的聚合着色剂)的混合物。
5 氨基甲酸酯改性的二苯基甲烷二异氰酸酯(PMDI)预聚物,其NCO含量为约30.4,官能度为约2.8且在25℃下的粘度为235-435mPa·s,通过使过量的聚亚甲基聚(异氰酸苯酯)与数均分子量为约450的聚酯多元醇反应而制备,如美国专利号5,962,541中所述。
8含有65重量%的MDI和29重量%的2,4-MDI的中等官能度的p-MDI,基于MDI的总重量计。
9 2,2'-MDI、2,4'-MDI和4,4-MDI的混合物,其含有55重量%的2,4'-MDI,基于MDI的总重量计。
10含有49重量%的MDI和28重量%2,4'-MDI的中等官能度的p-MDI,基于MDI的总重量计。
为了制备涂覆的沙粒,将沙子在加热至93℃的烘箱中预干燥最少2小时。然后将沙子转移到装有混合器的合适的容器中,并以低速混合。然后经约15秒的时间将偶联剂加入到沙子中。其后,经30秒的时间加入多元醇,并提高混合速度。接下来,经15秒的时间加入表面活性剂(如果使用),随后伴随提高的混合速度经30秒的时间加入异氰酸酯。然后经10秒的时间加入PUD(如果使用),并允许涂覆的沙子在高速下混合2分钟。然后停止混合,并通过将二氧化硅倾倒到涂覆的沙子中来加入二氧化硅。然后在高速下重新开始混合2分钟,然后停止混合,并从容器中倒出涂覆的沙子。
测试和结果
根据以下方法对实施例1-6中制备的涂覆的沙子进行测试以确定其初始UCS及其在环境条件(约20℃(68℉)和1atm绝对压力(14.7psia))下老化2周后的UCS(下文中称为“老化的UCS”)。
将80克涂覆的沙子(80g)与200mL的2%的KCl或线性流体混合,并倒入到来自Proptester,Inc的1 1/8英寸长的高压高温安全池中。排干液体,使用氮气将池子加压至1000psi,并在该压力和150℉下保持24小时。之后,对池子减压,小心地取出由此形成的圆盘(puck),并通过使用水压机压碎压实的支撑剂填充物来测试其强度。在圆盘上缓慢施加压力(100psi/分),并记录圆盘被彻底破坏时的压力。以其中压实的支撑剂填塞物发生彻底破坏时的点记录UCS载荷,单位为psi。结果示于表2中。
表2
实施例编号 | 初始UCS | 老化的UCS | UCS保留率% |
1 | 200psi(1379kPa) | 60psi(414kPa) | 30% |
2 | 180psi(1241kPa) | 75psi(517kPa) | 42% |
3 | 180psi(1241kPa) | 110psi(758kPa) | 61% |
4 | 180psi(1241kPa) | 140psi(965kPa) | 78% |
5 | 200psi(1379kPa) | 180psi(1241kPa) | 90% |
6 | 220psi(1517kPa) | 209psi(1441kPa) | 95% |
7 | 195psi(1344kPa) | 175psi(1206kPa) | 90% |
8 | 150psi(1034kPa) | 110psi(7584kPa) | 73% |
实施例9-11
涂覆的颗粒的制备
对于实施例9,使用在表3中列出的成分和量(以克计)来制备涂覆的沙粒。
表3
组分 | 量(以份计) |
沙子<sup>1</sup> | 1362 |
偶联剂<sup>2</sup> | 1.8 |
多元醇<sup>3</sup> | 8 |
表面活性剂<sup>4</sup> | 3.6 |
异氰酸酯1<sup>5</sup> | 13 |
PUD<sup>6</sup> | -- |
二氧化硅<sup>7</sup> | -- |
为了制备实施例9的涂覆的沙粒,首先使用实施例1-8的上述方法涂覆沙子,不同之处在于省略加入PUD和二氧化硅。
为了制备实施例10的涂覆的沙子,经10秒将1391克在实施例9中制备的涂覆的沙子与8份的多元醇混合,然后经10秒加入13份的异氰酸酯1。
为了制备实施例11的涂覆的沙子,经10秒将1362克在实施例10中制备的涂覆的沙子与8份的多元醇混合,然后经10秒加入13份的异氰酸酯1。然后停止混合,并通过将二氧化硅倾倒到涂覆的沙子中来加入2.7份的二氧化硅。然后在高速下重新开始混合2分钟,然后停止混合,并从容器中倒出涂覆的沙子。
测试和结果
使用实施例1-8的上述方法对实施例9-11中制备的涂覆的沙子进行测试以确定其初始UCS及其老化的UCS。结果见表4。
表4
实施例编号 | 初始UCS | 老化的UCS | UCS保留率% |
1 | 200psi(1379kPa) | 60psi(414kPa) | 30% |
9 | 14psi(97kPa) | 23psi(159kPa) | 164% |
10 | 105psi(724kPa) | 111psi(765kPa) | 106% |
11 | 250psi(1724kPa) | 210psi(1448kPa) | 84% |
尽管为示例说明的目的已在前面详述了本发明,但应当理解,这样的细节仅用于该目的,并且在不脱离本发明的精神和范围的情况下,本领域技术人员可以在其中作出各种变化,除非其可能受到权利要求书的限制。
Claims (23)
1.涂覆的颗粒,其包括:
(a)粒径不大于3目的基质颗粒;和
(b)置于至少一部分颗粒上的涂层,其中所述涂层包含反应混合物的缩合反应产物,所述反应混合物包含:
(i)包含至少10重量%的2,4'-亚甲基二苯基二异氰酸酯和/或2,2'-亚甲基二苯基二异氰酸酯的亚甲基二苯基二异氰酸酯混合物,基于混合物的总重量计;和
(ii)包含以下物质的异氰酸酯反应性组合物:
(A)植物油聚酯多元醇;
(B)芳族二胺;和
(C)用于羟基和异氰酸酯基团之间的反应的催化剂。
2.权利要求1所述的涂覆的颗粒,其中基质颗粒包含沙粒。
3.权利要求1所述的涂覆的颗粒,其中亚甲基二苯基二异氰酸酯混合物包含至少15重量%的2,4'-亚甲基二苯基二异氰酸酯,基于混合物的总重量计。
4.权利要求1所述的涂覆的颗粒,其中亚甲基二苯基二异氰酸酯混合物包含至少25重量%的2,4'-亚甲基二苯基二异氰酸酯,基于混合物中亚甲基二苯基二异氰酸酯单体的总重量计。
5.权利要求1所述的涂覆的颗粒,其中所述植物油包括大豆油。
6.权利要求1所述的涂覆的颗粒,其中所述植物油聚酯多元醇以至少60重量%的量存在,基于异氰酸酯反应性组合物中存在的异氰酸酯反应性组分的总重量计;且所述芳族二胺以10至40重量%的量存在,基于异氰酸酯反应性组合物中存在的异氰酸酯反应性组分的总重量计。
7.权利要求1所述的涂覆的颗粒,其中反应混合物的NCO指数为180至400。
8.权利要求1所述的涂覆的颗粒,其中所述涂层还包含解晶温度为至少35℃的结晶或半结晶的聚酯/聚氨酯。
9.权利要求8所述的涂覆的颗粒,其中所述结晶或半结晶的聚酯/聚氨酯以0.01至1重量%的量存在,基于涂覆的颗粒的总重量计。
10.权利要求9所述的涂覆的颗粒,其中所述结晶或半结晶的聚酯/聚氨酯以0.1至0.4重量%的量存在,基于涂覆的颗粒的总重量计。
11.使用权利要求1所述的涂覆的颗粒的方法,包括:
(a)将涂覆的颗粒与载体流体合并以形成混合物,和
(b)将混合物注入到至地下地质层的井眼中。
12.涂覆的颗粒,其包括:
(a)粒径不大于3目的基质颗粒;和
(b)置于至少一部分颗粒上的涂层,其中所述涂层包含:
(1)包含以下物质的反应混合物的缩合反应产物:
(i)液体的异氰酸酯官能化组分;和
(ii)包含以下物质的异氰酸酯反应性组合物:
(A)多元醇;
(B)芳族二胺;和
(C)用于羟基和异氰酸酯基团之间的反应的催化剂;和
(2)解晶温度为至少35℃的结晶或半结晶的聚酯/聚氨酯。
13.权利要求12所述的涂覆的颗粒,其中所述基质颗粒包含沙粒。
14.权利要求12所述的涂覆的颗粒,其中液体的异氰酸酯官能化组分包含氨基甲酸酯改性的异氰酸酯封端的预聚物,所述预聚物包含:
(i)聚合的二苯基甲烷二异氰酸酯与聚酯多元醇或包含聚酯多元醇的多元醇的掺混物的反应产物,其中液体的氨基甲酸酯改性的二苯基甲烷二异氰酸酯预聚物的NCO官能度为2.5至3.2且NCO基团含量为25重量%至33重量%,和/或
(ii)具有支链碳链的脂族二羟基化合物与4,4'-二苯基胺二异氰酸酯和/或其2,4'-异构体的反应产物,其中液体的氨基甲酸酯改性的二苯基甲烷二异氰酸酯的NCO基团含量为20重量%至24重量%。
15.权利要求12所述的涂覆的颗粒,其中所述液体的异氰酸酯官能化组分包含亚甲基二苯基二异氰酸酯混合物,所述混合物包含至少10重量%的2,4'-亚甲基二苯基二异氰酸酯和/或2,2'-亚甲基二苯基二异氰酸酯,基于混合物的总重量计。
16.权利要求15所述的涂覆的颗粒,其中所述亚甲基二苯基二异氰酸酯混合物包含至少15重量%的2,4'-亚甲基二苯基二异氰酸酯,基于混合物的总重量计。
17.权利要求15所述的涂覆的颗粒,其中所述亚甲基二苯基二异氰酸酯混合物包含至少25重量%的2,4'-亚甲基二苯基二异氰酸酯,基于混合物中的亚甲基二苯基二异氰酸酯单体的总重量计。
18.权利要求12所述的涂覆的颗粒,其中所述多元醇包括植物油聚酯多元醇。
19.权利要求18所述的涂覆的颗粒,其中所述植物油包括大豆油。
20.权利要求18所述的涂覆的颗粒,其中所述植物油聚酯多元醇以至少60重量%的量存在,基于异氰酸酯反应性组合物中存在的异氰酸酯反应性组分的总重量计;且其中所述芳族二胺以10至40重量%的量存在,基于异氰酸酯反应性组合物中存在的异氰酸酯反应性组分的总重量计。
21.权利要求12所述的涂覆的颗粒,其中反应混合物的NCO指数为180至400。
22.使用权利要求12所述的涂覆的颗粒的方法,包括:
(a)将涂覆的颗粒与载体流体合并以形成混合物,和
(b)将混合物注入到至地下地质层的井眼中。
23.制备涂覆的颗粒的方法,包括:
(1)将粒径不大于3目的基质颗粒与第一部分异氰酸酯反应性组合物和第一部分液体的异氰酸酯官能化组分混合;
(2)允许所述第一部分异氰酸酯反应性组合物和所述第一部分液体的异氰酸酯官能化组分之间的缩合反应发生,以形成涂覆的颗粒;然后
(3)分一个或更多个另外的步骤将由此制备的涂覆的颗粒与第二部分异氰酸酯反应性组合物和第二部分异氰酸酯官能化组分混合。
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PCT/US2018/047021 WO2019040347A1 (en) | 2017-08-22 | 2018-08-20 | COATED PARTICLES, METHODS OF MAKING THE SAME AND USE THEREOF AS FEEDING AGENTS |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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Publication number | Priority date | Publication date | Assignee | Title |
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TWI696640B (zh) * | 2019-05-28 | 2020-06-21 | 國家中山科學研究院 | 耐磨混成物之製法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20150034314A1 (en) * | 2013-08-01 | 2015-02-05 | Bayer Materialscience Llc | Coated particles and methods for their manufacture and use |
CN105793385A (zh) * | 2013-08-30 | 2016-07-20 | 优选技术有限责任公司 | 具有复合材料涂层的支撑剂 |
US20160333535A1 (en) * | 2015-05-15 | 2016-11-17 | Bayer Materialscience Llc | Free-flowing coated rubber particles, methods for their production and use |
Family Cites Families (264)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2882249A (en) | 1955-01-28 | 1959-04-14 | Stamford Rubber Supply Company | Organic materials prepared with the polyisocyanates and their preparation |
DE1495745C3 (de) | 1963-09-19 | 1978-06-01 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung wäßriger, emulgatorfreier Polyurethan-Latices |
DE1229290B (de) | 1965-04-21 | 1966-11-24 | Bayer Ag | Verfahren zur Herstellung von Urethangruppen enthaltenden Schaumstoffen |
US3484227A (en) | 1965-05-13 | 1969-12-16 | Fabricacion De Maquinas | Drawing and/or annealing rolls for sheet glass making apparatus |
DE1618380C3 (de) | 1967-03-08 | 1975-09-11 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung eines bei Raumtemperatur flüssigen Diphenylmethan-diisocyanatpräparates |
DE1770068C3 (de) | 1968-03-27 | 1981-01-15 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Polyurethanen Bayer AG, 5090 Leverkusen |
US4025477A (en) | 1973-03-22 | 1977-05-24 | Union Carbide Corporation | Acrylated epoxidized soybean oil urethane derivatives |
US4108814A (en) | 1974-09-28 | 1978-08-22 | Bayer Aktiengesellschaft | Aqueous polyurethane dispersions from solvent-free prepolymers using sulfonate diols |
DE2725589A1 (de) | 1977-06-07 | 1978-12-21 | Bayer Ag | Verfahren zur herstellung von waessrigen polyurethan-dispersionen und -loesungen |
DE2732131A1 (de) | 1977-07-15 | 1979-01-25 | Bayer Ag | Verfahren zur herstellung von seitenstaendige hydroxylgruppen aufweisenden isocyanat-polyadditionsprodukten |
DE2811148A1 (de) | 1978-03-15 | 1979-09-20 | Bayer Ag | Verfahren zur herstellung von waessrigen polyurethan-dispersionen und -loesungen |
DE2843790A1 (de) | 1978-10-06 | 1980-04-17 | Bayer Ag | Verfahren zur herstellung von waessrigen dispersionen oder loesungen von polyurethan-polyharnstoffen, die nach diesem verfahren erhaeltlichen dispersionen oder loesungen, sowie ihre verwendung |
DE3246612A1 (de) | 1982-12-16 | 1984-06-20 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur herstellung modifizierter triglyceride mit im mittel epoxid- und hydroxyl- sowie ethergruppen |
DE3317194A1 (de) | 1983-05-11 | 1984-11-15 | Henkel KGaA, 4000 Düsseldorf | Polyurethan-prepolymere auf basis oleochemischer polyole, ihre herstellung und verwendung |
DE3347045A1 (de) | 1983-12-24 | 1985-07-04 | Henkel KGaA, 4000 Düsseldorf | Zweikomponentenpolyurethanklebstoff |
US4644027A (en) | 1985-07-15 | 1987-02-17 | Stepan Company | Self-compatibilizing phthalate-based polyester polyols |
DE3626223A1 (de) | 1986-08-02 | 1988-02-04 | Henkel Kgaa | Polyurethan-praepolymere auf basis oleochemischer polyole, ihre herstellung und verwendung |
US5048608A (en) | 1989-01-31 | 1991-09-17 | Atlantic Richfield Company | Consolidation of hydraulic fractures employing a polyurethane resin |
US4920192A (en) | 1989-01-31 | 1990-04-24 | Atlantic Richfield Company | Polyurethane quasi prepolymer for proppant consolidation |
DE3935127A1 (de) | 1989-10-21 | 1991-04-25 | Henkel Kgaa | Verfahren zur herstellung von esterpolyole enthaltenden reaktionsmischungen |
DE3943080A1 (de) | 1989-12-27 | 1991-07-04 | Henkel Kgaa | Verwendung von polyesterpolyolen enthaltenden reaktionsmischungen bei der herstellung von massiven polyurethanwerkstoffen nach dem giessverfahren |
US5081204A (en) | 1990-02-09 | 1992-01-14 | Mobay Corporation | Polyurethane elastomers |
US5199491A (en) | 1991-09-04 | 1993-04-06 | Atlantic Richfield Company | Method of using nitrile derivative for sand control |
US5485882A (en) | 1994-10-27 | 1996-01-23 | Exxon Production Research Company | Low-density ball sealer for use as a diverting agent in hostile environment wells |
US5501274A (en) | 1995-03-29 | 1996-03-26 | Halliburton Company | Control of particulate flowback in subterranean wells |
US5839510A (en) | 1995-03-29 | 1998-11-24 | Halliburton Energy Services, Inc. | Control of particulate flowback in subterranean wells |
US5833000A (en) | 1995-03-29 | 1998-11-10 | Halliburton Energy Services, Inc. | Control of particulate flowback in subterranean wells |
US5582249A (en) | 1995-08-02 | 1996-12-10 | Halliburton Company | Control of particulate flowback in subterranean wells |
US5775425A (en) | 1995-03-29 | 1998-07-07 | Halliburton Energy Services, Inc. | Control of fine particulate flowback in subterranean wells |
US5787986A (en) | 1995-03-29 | 1998-08-04 | Halliburton Energy Services, Inc. | Control of particulate flowback in subterranean wells |
DE19533168A1 (de) | 1995-09-08 | 1997-03-13 | Henkel Kgaa | Fettchemische Polyole als Reaktivverdünner |
US5697440A (en) | 1996-01-04 | 1997-12-16 | Halliburton Energy Services, Inc. | Control of particulate flowback in subterranean wells |
US5960880A (en) | 1996-08-27 | 1999-10-05 | Halliburton Energy Services, Inc. | Unconsolidated formation stimulation with sand filtration |
US6330916B1 (en) | 1996-11-27 | 2001-12-18 | Bj Services Company | Formation treatment method using deformable particles |
US7426961B2 (en) | 2002-09-03 | 2008-09-23 | Bj Services Company | Method of treating subterranean formations with porous particulate materials |
US6059034A (en) | 1996-11-27 | 2000-05-09 | Bj Services Company | Formation treatment method using deformable particles |
US6364018B1 (en) | 1996-11-27 | 2002-04-02 | Bj Services Company | Lightweight methods and compositions for well treating |
US6772838B2 (en) | 1996-11-27 | 2004-08-10 | Bj Services Company | Lightweight particulate materials and uses therefor |
US6749025B1 (en) | 1996-11-27 | 2004-06-15 | Bj Services Company | Lightweight methods and compositions for sand control |
US5819851A (en) | 1997-01-16 | 1998-10-13 | Dallas; L. Murray | Blowout preventer protector for use during high pressure oil/gas well stimulation |
US5791415A (en) | 1997-03-13 | 1998-08-11 | Halliburton Energy Services, Inc. | Stimulating wells in unconsolidated formations |
US5924488A (en) | 1997-06-11 | 1999-07-20 | Halliburton Energy Services, Inc. | Methods of preventing well fracture proppant flow-back |
US5962541A (en) | 1997-10-30 | 1999-10-05 | Bayer Corporation | Isocyanate-terminated prepolymers and rigid-foams produced therefrom |
DE69815054T2 (de) | 1998-02-03 | 2003-11-27 | Halliburton Energy Serv Inc | Verfahren zur schnellen Verfestigung von Teilchen in Bohrlöcher |
US6225262B1 (en) | 1998-05-29 | 2001-05-01 | 3M Innovative Properties Company | Encapsulated breaker slurry compositions and methods of use |
US6582819B2 (en) | 1998-07-22 | 2003-06-24 | Borden Chemical, Inc. | Low density composite proppant, filtration media, gravel packing media, and sports field media, and methods for making and using same |
WO2000005302A1 (en) | 1998-07-22 | 2000-02-03 | Borden Chemical, Inc. | Composite proppant, composite filtration media and methods for making and using same |
US6107433A (en) | 1998-11-06 | 2000-08-22 | Pittsburg State University | Process for the preparation of vegetable oil-based polyols and electroninsulating casting compounds created from vegetable oil-based polyols |
US6433121B1 (en) | 1998-11-06 | 2002-08-13 | Pittsburg State University | Method of making natural oil-based polyols and polyurethanes therefrom |
US6599863B1 (en) | 1999-02-18 | 2003-07-29 | Schlumberger Technology Corporation | Fracturing process and composition |
US6155348A (en) | 1999-05-25 | 2000-12-05 | Halliburton Energy Services, Inc. | Stimulating unconsolidated producing zones in wells |
US6257335B1 (en) | 2000-03-02 | 2001-07-10 | Halliburton Energy Services, Inc. | Stimulating fluid production from unconsolidated formations |
WO2001094744A1 (en) | 2000-06-06 | 2001-12-13 | T R Oil Services Limited | Microcapsule well treatment |
US20020070020A1 (en) | 2000-12-08 | 2002-06-13 | Nguyen Philip D. | Completing wells in unconsolidated formations |
US6891053B2 (en) | 2001-10-02 | 2005-05-10 | Noveon Ip Holdings Corp. | Method of making oleochemical oil-based polyols |
US6725931B2 (en) | 2002-06-26 | 2004-04-27 | Halliburton Energy Services, Inc. | Methods of consolidating proppant and controlling fines in wells |
US7343973B2 (en) | 2002-01-08 | 2008-03-18 | Halliburton Energy Services, Inc. | Methods of stabilizing surfaces of subterranean formations |
US7267171B2 (en) | 2002-01-08 | 2007-09-11 | Halliburton Energy Services, Inc. | Methods and compositions for stabilizing the surface of a subterranean formation |
US7216711B2 (en) | 2002-01-08 | 2007-05-15 | Halliburton Eenrgy Services, Inc. | Methods of coating resin and blending resin-coated proppant |
US6962200B2 (en) | 2002-01-08 | 2005-11-08 | Halliburton Energy Services, Inc. | Methods and compositions for consolidating proppant in subterranean fractures |
US6668926B2 (en) | 2002-01-08 | 2003-12-30 | Halliburton Energy Services, Inc. | Methods of consolidating proppant in subterranean fractures |
US7098291B2 (en) | 2002-06-10 | 2006-08-29 | Rohm And Haas Company | Urethane polymer compositions |
US6705400B1 (en) | 2002-08-28 | 2004-03-16 | Halliburton Energy Services, Inc. | Methods and compositions for forming subterranean fractures containing resilient proppant packs |
US6832650B2 (en) | 2002-09-11 | 2004-12-21 | Halliburton Energy Services, Inc. | Methods of reducing or preventing particulate flow-back in wells |
US6866099B2 (en) | 2003-02-12 | 2005-03-15 | Halliburton Energy Services, Inc. | Methods of completing wells in unconsolidated subterranean zones |
US7114570B2 (en) | 2003-04-07 | 2006-10-03 | Halliburton Energy Services, Inc. | Methods and compositions for stabilizing unconsolidated subterranean formations |
CA2521007C (en) | 2003-04-15 | 2009-08-11 | Hexion Specialty Chemicals, Inc. | Particulate material containing thermoplastic elastomer and methods for making and using same |
US7772163B1 (en) | 2003-06-20 | 2010-08-10 | Bj Services Company Llc | Well treating composite containing organic lightweight material and weight modifying agent |
US7207386B2 (en) | 2003-06-20 | 2007-04-24 | Bj Services Company | Method of hydraulic fracturing to reduce unwanted water production |
US7413010B2 (en) | 2003-06-23 | 2008-08-19 | Halliburton Energy Services, Inc. | Remediation of subterranean formations using vibrational waves and consolidating agents |
US7048048B2 (en) | 2003-06-26 | 2006-05-23 | Halliburton Energy Services, Inc. | Expandable sand control screen and method for use of same |
US7021379B2 (en) | 2003-07-07 | 2006-04-04 | Halliburton Energy Services, Inc. | Methods and compositions for enhancing consolidation strength of proppant in subterranean fractures |
US7066258B2 (en) | 2003-07-08 | 2006-06-27 | Halliburton Energy Services, Inc. | Reduced-density proppants and methods of using reduced-density proppants to enhance their transport in well bores and fractures |
US7036589B2 (en) | 2003-08-14 | 2006-05-02 | Halliburton Energy Services, Inc. | Methods for fracturing stimulation |
US7237609B2 (en) | 2003-08-26 | 2007-07-03 | Halliburton Energy Services, Inc. | Methods for producing fluids from acidized and consolidated portions of subterranean formations |
US7059406B2 (en) | 2003-08-26 | 2006-06-13 | Halliburton Energy Services, Inc. | Production-enhancing completion methods |
US20050194142A1 (en) | 2004-03-05 | 2005-09-08 | Nguyen Philip D. | Compositions and methods for controlling unconsolidated particulates |
US20050263283A1 (en) | 2004-05-25 | 2005-12-01 | Nguyen Philip D | Methods for stabilizing and stimulating wells in unconsolidated subterranean formations |
US7073581B2 (en) | 2004-06-15 | 2006-07-11 | Halliburton Energy Services, Inc. | Electroconductive proppant compositions and related methods |
WO2006023172A2 (en) | 2004-08-16 | 2006-03-02 | Fairmount Minerals, Ltd. | Control of particulate flowback in subterranean formations using elastomeric resin coated proppants |
BRPI0515236A (pt) * | 2004-09-02 | 2008-07-15 | Ppg Ind Ohio Inc | composição de revestimento de poliuréia, revestimento compósito multi-componente, artigo revestido, método para formar um revestimento de poliuréia sobre um substrato e método para formar um artigo revestido |
US7299869B2 (en) | 2004-09-03 | 2007-11-27 | Halliburton Energy Services, Inc. | Carbon foam particulates and methods of using carbon foam particulates in subterranean applications |
US7255169B2 (en) | 2004-09-09 | 2007-08-14 | Halliburton Energy Services, Inc. | Methods of creating high porosity propped fractures |
US7281580B2 (en) | 2004-09-09 | 2007-10-16 | Halliburton Energy Services, Inc. | High porosity fractures and methods of creating high porosity fractures |
US8227026B2 (en) | 2004-09-20 | 2012-07-24 | Momentive Specialty Chemicals Inc. | Particles for use as proppants or in gravel packs, methods for making and using the same |
US7919183B2 (en) | 2004-09-20 | 2011-04-05 | Momentive Specialty Chemicals Inc. | Particles for use as proppants or in gravel packs, methods for making and using the same |
US7325608B2 (en) | 2004-12-01 | 2008-02-05 | Halliburton Energy Services, Inc. | Methods of hydraulic fracturing and of propping fractures in subterranean formations |
US7281581B2 (en) | 2004-12-01 | 2007-10-16 | Halliburton Energy Services, Inc. | Methods of hydraulic fracturing and of propping fractures in subterranean formations |
US7398825B2 (en) | 2004-12-03 | 2008-07-15 | Halliburton Energy Services, Inc. | Methods of controlling sand and water production in subterranean zones |
US7273099B2 (en) | 2004-12-03 | 2007-09-25 | Halliburton Energy Services, Inc. | Methods of stimulating a subterranean formation comprising multiple production intervals |
US7883740B2 (en) | 2004-12-12 | 2011-02-08 | Halliburton Energy Services, Inc. | Low-quality particulates and methods of making and using improved low-quality particulates |
CA2784248C (en) | 2004-12-30 | 2015-02-10 | Sun Drilling Products Corporation | Thermoset nanocomposite particles, processing for their production, and their use in oil and natural gas drilling applications |
US8258083B2 (en) | 2004-12-30 | 2012-09-04 | Sun Drilling Products Corporation | Method for the fracture stimulation of a subterranean formation having a wellbore by using impact-modified thermoset polymer nanocomposite particles as proppants |
US7322411B2 (en) | 2005-01-12 | 2008-01-29 | Bj Services Company | Method of stimulating oil and gas wells using deformable proppants |
US7334635B2 (en) | 2005-01-14 | 2008-02-26 | Halliburton Energy Services, Inc. | Methods for fracturing subterranean wells |
CA2595686C (en) | 2005-01-21 | 2012-09-18 | A. Richard Sinclair | Soluble diverting agents |
US7267170B2 (en) | 2005-01-31 | 2007-09-11 | Halliburton Energy Services, Inc. | Self-degrading fibers and associated methods of use and manufacture |
US7334636B2 (en) | 2005-02-08 | 2008-02-26 | Halliburton Energy Services, Inc. | Methods of creating high-porosity propped fractures using reticulated foam |
US7318473B2 (en) | 2005-03-07 | 2008-01-15 | Halliburton Energy Services, Inc. | Methods relating to maintaining the structural integrity of deviated well bores |
DE102005012794A1 (de) | 2005-03-19 | 2006-09-21 | Bayer Materialscience Ag | Poly(etherester)polyole und Verfahren zu ihrer Herstellung |
US7528096B2 (en) | 2005-05-12 | 2009-05-05 | Bj Services Company | Structured composite compositions for treatment of subterranean wells |
US7363978B2 (en) | 2005-05-20 | 2008-04-29 | Halliburton Energy Services, Inc. | Methods of using reactive surfactants in subterranean operations |
US7500519B2 (en) | 2005-05-20 | 2009-03-10 | Halliburton Energy Services, Inc. | Methods of modifying fracture faces and other surfaces in subterranean formations |
US20060260808A1 (en) | 2005-05-20 | 2006-11-23 | Weaver Jim D | Methods of treating particulates and use in subterranean formations |
EP1904601B1 (en) | 2005-06-13 | 2015-05-06 | Sun Drilling Products Corp. | Thermoset particles with enhanced crosslinking, processing for their production, and their use in oil and natural gas drilling applications |
US7318474B2 (en) | 2005-07-11 | 2008-01-15 | Halliburton Energy Services, Inc. | Methods and compositions for controlling formation fines and reducing proppant flow-back |
CN101238270B (zh) | 2005-08-09 | 2013-05-01 | 迈图专业化学股份有限公司 | 测定地层中裂缝几何形状的方法和组合物 |
US7845409B2 (en) | 2005-12-28 | 2010-12-07 | 3M Innovative Properties Company | Low density proppant particles and use thereof |
US8443890B2 (en) | 2006-01-04 | 2013-05-21 | Halliburton Energy Services, Inc. | Methods of stimulating liquid-sensitive subterranean formations |
CA2573834A1 (en) | 2006-01-13 | 2007-07-13 | Diversifield Industries Ltd. | Polyurethane proppant particle and use thereof |
US8613320B2 (en) | 2006-02-10 | 2013-12-24 | Halliburton Energy Services, Inc. | Compositions and applications of resins in treating subterranean formations |
US8333241B2 (en) | 2006-02-10 | 2012-12-18 | Halliburton Energy Services, Inc. | Methods and compositions for packing void spaces and stabilizing formations surrounding a wellbore |
US7926591B2 (en) | 2006-02-10 | 2011-04-19 | Halliburton Energy Services, Inc. | Aqueous-based emulsified consolidating agents suitable for use in drill-in applications |
US7819192B2 (en) | 2006-02-10 | 2010-10-26 | Halliburton Energy Services, Inc. | Consolidating agent emulsions and associated methods |
US7665517B2 (en) | 2006-02-15 | 2010-02-23 | Halliburton Energy Services, Inc. | Methods of cleaning sand control screens and gravel packs |
CA2580304C (en) | 2006-03-08 | 2010-07-20 | Bj Services Company | Curable resin coated low apparent specific gravity beads and method of using the same |
US7494711B2 (en) | 2006-03-08 | 2009-02-24 | Bj Services Company | Coated plastic beads and methods of using same to treat a wellbore or subterranean formation |
US7407010B2 (en) | 2006-03-16 | 2008-08-05 | Halliburton Energy Services, Inc. | Methods of coating particulates |
US7727940B2 (en) | 2006-06-06 | 2010-06-01 | Halliburton Energy Services, Inc. | Silicone-tackifier matrixes and methods of use thereof |
US9303203B2 (en) | 2006-06-06 | 2016-04-05 | Schlumberger Technology Corporation | Thermoviscoelastic system fluid and well treatment method |
US7900702B2 (en) | 2006-06-06 | 2011-03-08 | Halliburton Energy Services, Inc. | Silicone-tackifier matrixes and methods of use thereof |
US7933718B2 (en) | 2006-08-09 | 2011-04-26 | Momentive Specialty Chemicals Inc. | Method and tool for determination of fracture geometry in subterranean formations based on in-situ neutron activation analysis |
US8562900B2 (en) | 2006-09-01 | 2013-10-22 | Imerys | Method of manufacturing and using rod-shaped proppants and anti-flowback additives |
US7674925B2 (en) | 2006-09-21 | 2010-03-09 | Athletic Polymer Systems, Inc. | Polyols from plant oils and methods of conversion |
US9120963B2 (en) | 2006-11-08 | 2015-09-01 | Schlumberger Technology Corporation | Delayed water-swelling materials and methods of use |
EP2949694A1 (en) | 2006-12-07 | 2015-12-02 | 3M Innovative Properties Company of 3M Center | Particles comprising a fluorinated siloxane and methods of making and using the same |
US8757259B2 (en) | 2006-12-08 | 2014-06-24 | Schlumberger Technology Corporation | Heterogeneous proppant placement in a fracture with removable channelant fill |
US9085727B2 (en) | 2006-12-08 | 2015-07-21 | Schlumberger Technology Corporation | Heterogeneous proppant placement in a fracture with removable extrametrical material fill |
US7581590B2 (en) | 2006-12-08 | 2009-09-01 | Schlumberger Technology Corporation | Heterogeneous proppant placement in a fracture with removable channelant fill |
US8636065B2 (en) | 2006-12-08 | 2014-01-28 | Schlumberger Technology Corporation | Heterogeneous proppant placement in a fracture with removable channelant fill |
US8763699B2 (en) | 2006-12-08 | 2014-07-01 | Schlumberger Technology Corporation | Heterogeneous proppant placement in a fracture with removable channelant fill |
US20080179057A1 (en) | 2007-01-26 | 2008-07-31 | Bj Services Company | Well Treating Agents of Metallic Spheres and Methods of Using the Same |
US7624802B2 (en) | 2007-03-22 | 2009-12-01 | Hexion Specialty Chemicals, Inc. | Low temperature coated particles for use as proppants or in gravel packs, methods for making and using the same |
US9096790B2 (en) | 2007-03-22 | 2015-08-04 | Hexion Inc. | Low temperature coated particles comprising a curable liquid and a reactive powder for use as proppants or in gravel packs, methods for making and using the same |
US8317498B2 (en) | 2007-05-11 | 2012-11-27 | Schlumberger Technology Corporation | Valve-seat interface architecture |
US8506262B2 (en) | 2007-05-11 | 2013-08-13 | Schlumberger Technology Corporation | Methods of use for a positive displacement pump having an externally assisted valve |
US8276664B2 (en) | 2007-08-13 | 2012-10-02 | Baker Hughes Incorporated | Well treatment operations using spherical cellulosic particulates |
US7737091B2 (en) | 2007-08-28 | 2010-06-15 | Imerys | Proppants and anti-flowback additives made from sillimanite minerals, methods of manufacture, and methods of use |
ATE547498T1 (de) | 2007-12-05 | 2012-03-15 | 3M Innovative Properties Co | Verfahren zur in-situ-behandlung von stützmitteln und brüchen mit fluoriertem silan |
US20100263870A1 (en) | 2007-12-14 | 2010-10-21 | Dean Michael Willberg | Methods of contacting and/or treating a subterranean formation |
WO2009079315A2 (en) | 2007-12-14 | 2009-06-25 | 3M Innovative Properties Company | Fiber aggregate |
CN101586024A (zh) | 2008-05-21 | 2009-11-25 | 北京仁创科技集团有限公司 | 采油用覆膜颗粒、压裂支撑剂及采油方法 |
EP2172533A1 (en) | 2008-09-26 | 2010-04-07 | Services Pétroliers Schlumberger | Composition for borehole treatment |
BRPI0919963A2 (pt) | 2008-10-29 | 2015-12-08 | Basf Se | agente de escoramento, método para formar um agente de escoramento, e método para fraturamento hidráulico de uma formação subterrânea |
US9714378B2 (en) | 2008-10-29 | 2017-07-25 | Basf Se | Proppant |
US8360149B2 (en) | 2008-12-16 | 2013-01-29 | Schlumberger Technology Corporation | Surface modification for cross-linking or breaking interactions with injected fluid |
WO2010075248A1 (en) | 2008-12-23 | 2010-07-01 | 3M Innovative Properties Company | Curable fiber and compositions comprising the same; method of trating a subterranean formation |
US7921911B2 (en) | 2008-12-30 | 2011-04-12 | Schlumberger Technology Corporation | Surface-modifying agents for wettability modification |
US8240383B2 (en) | 2009-05-08 | 2012-08-14 | Momentive Specialty Chemicals Inc. | Methods for making and using UV/EB cured precured particles for use as proppants |
US20100282465A1 (en) | 2009-05-08 | 2010-11-11 | Halliburton Energy Services, Inc. | Methods of consolidating particulates using a hardenable resin and an orgaosilane coupling agent |
WO2010132362A2 (en) | 2009-05-11 | 2010-11-18 | Board Of Regents, The University Of Texas System | Method for treating hydrocarbon-bearing formations with fluorinated polyurethanes |
US8136595B2 (en) | 2009-08-07 | 2012-03-20 | Halliburton Energy Services, Inc. | Methods for controlling particulate flowback and migration in a subterranean formation |
US8136593B2 (en) | 2009-08-07 | 2012-03-20 | Halliburton Energy Services, Inc. | Methods for maintaining conductivity of proppant pack |
US20110071056A1 (en) | 2009-09-24 | 2011-03-24 | Rajesh K Saini | Degradable Surfactants, Including Degradable Gemini Surfactants, and Associated Methods |
WO2011050046A1 (en) | 2009-10-20 | 2011-04-28 | Soane Energy, Llc | Proppants for hydraulic fracturing technologies |
US8828269B1 (en) | 2009-11-16 | 2014-09-09 | Thomas M. Garrett | Method for increasing miscibility of natural oil polyol with petroleum-based polyol |
US8267176B2 (en) | 2009-12-17 | 2012-09-18 | Halliburton Energy Services, Inc. | Formation conditioning fluids comprising peroxides and methods relating thereto |
US8905135B2 (en) | 2010-03-24 | 2014-12-09 | Halliburton Energy Services, Inc. | Zero shear viscosifying agent |
US8268758B2 (en) | 2010-04-14 | 2012-09-18 | Halliburton Energy Services Inc. | Consolidating emulsions comprising convertible surfactant compositions and methods related thereto |
US8772205B2 (en) | 2010-04-30 | 2014-07-08 | Halliburton Energy Services, Inc. | Water-soluble degradable synthetic vinyl polymers and related methods |
US9334338B2 (en) | 2010-04-30 | 2016-05-10 | Halliburton Energy Services, Inc. | Water-soluble degradable synthetic vinyl polymers and related methods |
EP2596077A1 (en) | 2010-07-21 | 2013-05-29 | Basf Se | A proppant |
US8418761B2 (en) | 2010-07-29 | 2013-04-16 | Halliburton Energy Services, Inc. | Stimuli-responsive high viscosity pill |
WO2012021373A1 (en) | 2010-08-12 | 2012-02-16 | Conocophillips Company | Controlled release material |
DE102010051817A1 (de) | 2010-11-18 | 2012-05-24 | Ashland-Südchemie-Kernfest GmbH | Verfahren zur Herstellung beschichteter Proppants |
WO2012104190A1 (en) | 2011-01-31 | 2012-08-09 | Basf Se | A proppant |
US9371479B2 (en) | 2011-03-16 | 2016-06-21 | Schlumberger Technology Corporation | Controlled release biocides in oilfield applications |
US9403115B2 (en) | 2011-03-18 | 2016-08-02 | William Marsh Rice University | Graphite oxide coated particulate material and method of making thereof |
US8763700B2 (en) | 2011-09-02 | 2014-07-01 | Robert Ray McDaniel | Dual function proppants |
US9290690B2 (en) | 2011-05-03 | 2016-03-22 | Preferred Technology, Llc | Coated and cured proppants |
US8993489B2 (en) | 2011-05-03 | 2015-03-31 | Preferred Technology, Llc | Coated and cured proppants |
US9040467B2 (en) | 2011-05-03 | 2015-05-26 | Preferred Technology, Llc | Coated and cured proppants |
US9725645B2 (en) * | 2011-05-03 | 2017-08-08 | Preferred Technology, Llc | Proppant with composite coating |
CA2834826A1 (en) | 2011-05-05 | 2012-11-08 | Basf Se | A proppant |
MX2013012854A (es) | 2011-05-05 | 2014-01-08 | Basf Se | Un agente de sostén revestido con resina y métodos de uso. |
US9155310B2 (en) | 2011-05-24 | 2015-10-13 | Agienic, Inc. | Antimicrobial compositions for use in products for petroleum extraction, personal care, wound care and other applications |
US20120329683A1 (en) | 2011-06-23 | 2012-12-27 | Nicolas Droger | Degradable fiber systems for well treatments and their use |
US9297244B2 (en) | 2011-08-31 | 2016-03-29 | Self-Suspending Proppant Llc | Self-suspending proppants for hydraulic fracturing comprising a coating of hydrogel-forming polymer |
CN103764948B (zh) | 2011-08-31 | 2018-05-18 | 自悬浮支撑有限公司 | 用于水力破碎的自-悬浮支撑剂 |
CA2840368C (en) | 2011-09-01 | 2016-04-19 | Empire Technology Development Llc | Systems, materials, and methods for recovering material from bedrock using supercritical argon compositions |
US20130072588A1 (en) | 2011-09-21 | 2013-03-21 | Bayer Materialscience Llc | Medium density foams having good impact resistance and a process for their production |
CN103917622A (zh) | 2011-09-30 | 2014-07-09 | 迈图专业化学股份有限公司 | 支撑剂材料和定制支撑剂材料表面润湿性的方法 |
US8720556B2 (en) | 2011-11-30 | 2014-05-13 | Halliburton Energy Services, Inc. | Methods for initiating new fractures in a completed wellbore having existing fractures present |
US20140364538A1 (en) | 2011-12-07 | 2014-12-11 | University Of Florida Research Foundation, Inc. | Modified cellulose, methods of manufacture thereof and articles comprising the same |
DE102011121254A1 (de) | 2011-12-15 | 2013-06-20 | Ashland-Südchemie-Kernfest GmbH | Verfahren zur Herstellung beschichteter Proppants |
US9562187B2 (en) | 2012-01-23 | 2017-02-07 | Preferred Technology, Llc | Manufacture of polymer coated proppants |
US20130292116A1 (en) | 2012-05-02 | 2013-11-07 | Halliburton Energy Services, Inc. | Methods for Controlling Formation Fines Migration |
US9708527B2 (en) | 2012-05-03 | 2017-07-18 | Halliburton Energy Services, Inc. | Particulates having hydrophobic and oleophobic surfaces and methods relating thereto |
CA2875500C (en) | 2012-06-04 | 2019-02-26 | Imerys Oilfield Minerals, Inc. | Proppants and anti-flowback additives comprising flash calcined clay, methods of manufacture, and methods of use |
US9243182B2 (en) | 2012-08-21 | 2016-01-26 | American Air Liquide Inc. | Hydraulic fracturing with improved viscosity liquefied industrial gas based solution |
US9260650B2 (en) | 2012-08-29 | 2016-02-16 | Halliburton Energy Services, Inc. | Methods for hindering settling of proppant aggregates in subterranean operations |
US20140076558A1 (en) | 2012-09-18 | 2014-03-20 | Halliburton Energy Services, Inc. | Methods and Compositions for Treating Proppant to Prevent Flow-Back |
US8967263B2 (en) | 2012-09-18 | 2015-03-03 | Halliburton Energy Services, Inc. | Methods of treating a subterranean formation with stress-activated resins |
US9879503B2 (en) | 2012-09-19 | 2018-01-30 | Halliburton Energy Services, Inc. | Methods of treating long-interval and high-contrast permeability subterranean formations with diverting fluids |
US9169433B2 (en) | 2012-09-27 | 2015-10-27 | Halliburton Energy Services, Inc. | Methods for enhancing well productivity and minimizing water production using swellable polymers |
US9701589B2 (en) | 2012-10-23 | 2017-07-11 | Hd Proppants Llc | Proppants for use in hydrofracking |
US9951266B2 (en) | 2012-10-26 | 2018-04-24 | Halliburton Energy Services, Inc. | Expanded wellbore servicing materials and methods of making and using same |
US20140116698A1 (en) | 2012-10-26 | 2014-05-01 | Halliburton Energy Services, Inc. | Wellbore Servicing Fluids Comprising Foamed Materials and Methods of Making and Using Same |
US9279077B2 (en) | 2012-11-09 | 2016-03-08 | Halliburton Energy Services, Inc. | Methods of forming and placing proppant pillars into a subterranean formation |
US9243183B2 (en) | 2012-11-28 | 2016-01-26 | Halliburton Energy Services, Inc. | Methods of treating a subterranean formation with thermally activated suspending agents |
US9321956B2 (en) | 2012-11-28 | 2016-04-26 | Halliburton Energy Services, Inc. | Methods for hindering the settling of particulates in a subterranean formation |
US9429005B2 (en) | 2012-11-28 | 2016-08-30 | Halliburton Energy Services, Inc. | Methods for hindering the settling of proppant in a subterranean formation |
US20140144631A1 (en) | 2012-11-28 | 2014-05-29 | Halliburton Energy Services, Inc | Methods of Forming Functionalized Proppant Particulates for Use in Subterranean Formation Operations |
US8517103B1 (en) | 2012-12-04 | 2013-08-27 | Halliburton Energy Services, Inc. | Oil or gas treatment fluid containing a chelate or coordination complex that sets |
JP2016507602A (ja) | 2012-12-14 | 2016-03-10 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | プロパント |
US9587476B2 (en) | 2013-01-04 | 2017-03-07 | Halliburton Energy Services, Inc. | Single component resin systems and methods relating thereto |
US9359547B2 (en) | 2013-01-31 | 2016-06-07 | Halliburton Energy Services, Inc. | Wellbore servicing compositions and methods of making and using same |
MX2015009841A (es) * | 2013-02-01 | 2015-12-01 | Basf Se | Un agente de consolidacion. |
US9206345B2 (en) | 2013-02-12 | 2015-12-08 | Halliburton Energy Services, Inc. | Wellbore servicing compositions and methods of making and using same |
US9677386B2 (en) | 2013-02-28 | 2017-06-13 | Halliburton Energy Services, Inc. | Methods of stabilizing weakly consolidated subterranean formation intervals |
US8584754B1 (en) | 2013-02-28 | 2013-11-19 | Halliburton Energy Services, Inc. | Delayed-tackifier coated particulates and methods relating thereto |
US20140262262A1 (en) | 2013-03-13 | 2014-09-18 | Landec Corporation | Compositions and Methods for the Controlled Release of Active Ingredients |
US9862880B2 (en) | 2013-03-14 | 2018-01-09 | Lawrence Livermore National Security, Llc | Encapsulated proppants |
EP2971497A4 (en) | 2013-03-15 | 2017-03-29 | Carbo Ceramics Inc. | Composition and method for hydraulic fracturing and evaluation and diagnostics of hydraulic fractures using infused porous ceramic proppant |
JP2016517462A (ja) | 2013-03-15 | 2016-06-16 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | プロパント |
US9518214B2 (en) | 2013-03-15 | 2016-12-13 | Preferred Technology, Llc | Proppant with polyurea-type coating |
JP2016516851A (ja) | 2013-03-15 | 2016-06-09 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | プロパント |
US9797231B2 (en) | 2013-04-25 | 2017-10-24 | Halliburton Energy Services, Inc. | Methods of coating proppant particulates for use in subterranean formation operations |
US10100247B2 (en) | 2013-05-17 | 2018-10-16 | Preferred Technology, Llc | Proppant with enhanced interparticle bonding |
US20160145486A1 (en) | 2013-07-31 | 2016-05-26 | Halliburton Energy Services, Inc. | Wellbore servicing compositions and methods of making and using same |
MX2015017433A (es) | 2013-07-31 | 2016-03-31 | Halliburton Energy Services Inc | Materiales de mantenimiento de pozo y metodos para su elaboracion y su uso. |
WO2015016934A1 (en) | 2013-08-01 | 2015-02-05 | Halliburton Energy Services, Inc. | Resin composition for treatment of a subterranean formation |
AU2013398334B2 (en) | 2013-08-22 | 2017-06-29 | Halliburton Energy Services, Inc. | Compositions including a particulate bridging agent and fibers and methods of treating a subterranean formation with the same |
US9816365B2 (en) | 2013-08-23 | 2017-11-14 | Halliburton Energy Services, Inc. | Fracturing treatments in subterranean formations using reducible materials |
US9523268B2 (en) | 2013-08-23 | 2016-12-20 | Schlumberger Technology Corporation | In situ channelization method and system for increasing fracture conductivity |
US9790777B2 (en) | 2013-09-04 | 2017-10-17 | Halliburton Energy Services, Inc. | Fracturing fluids comprising fibers treated with crosslinkable, hydratable polymers and related methods |
GB201315848D0 (en) | 2013-09-05 | 2013-10-23 | Johnson Matthey Plc | Tracer and method |
EP3046987B8 (en) | 2013-09-20 | 2019-06-26 | Baker Hughes, a GE company, LLC | Use of organophosphorus containing composites for use in well treatment operations |
WO2015041673A1 (en) | 2013-09-20 | 2015-03-26 | Halliburton Energy Services, Inc. | Compositions and methods for forming and utilizing stable, single-component resin mixture |
CA2923232C (en) | 2013-09-26 | 2018-10-16 | Baker Hughes Incorporated | Method of optimizing conductivity in a hydraulic fracturing operation |
US9957440B2 (en) | 2013-09-27 | 2018-05-01 | Halliburton Energy Services, Inc. | Expandable particulates and methods of use and preparation |
WO2015057215A1 (en) | 2013-10-16 | 2015-04-23 | Halliburton Energy Services, Inc. | Compositions providing consolidation and water-control |
US20150107835A1 (en) | 2013-10-17 | 2015-04-23 | Schlumberger Technology Corporation | Well treatment with shapeshifting particles |
CA2924465A1 (en) | 2013-11-11 | 2015-05-14 | Halliburton Energy Services, Inc. | Methods for enhancing propped fracture conductivity |
BR112016011806A2 (pt) | 2013-11-26 | 2017-08-08 | Basf Se | Estruturante para fraturar hidraulicamente uma formação subterrânea, e, método para formar um estruturante |
US10329891B2 (en) | 2013-12-11 | 2019-06-25 | Halliburton Energy Services, Inc. | Treating a subterranean formation with a composition having multiple curing stages |
US20160208157A1 (en) | 2013-12-11 | 2016-07-21 | Halliburton Energy Services, Inc. | Consolidation composition including polyhedral oligomeric silsesquioxane and methods of using the same |
US20160281498A1 (en) | 2014-02-18 | 2016-09-29 | Halliburton Energy Services, Inc. | Methods for obtaining data from a subterranean formation |
US20150252252A1 (en) | 2014-03-05 | 2015-09-10 | Self-Suspending Proppant Llc | Humidity-resistant self-suspending proppants |
US10179875B2 (en) | 2014-03-24 | 2019-01-15 | Halliburton Energy Services, Inc. | Functionalized proppant particulates for use in subterranean formation consolidation operations |
US9410402B2 (en) | 2014-03-25 | 2016-08-09 | Sharp-Rock Technologies, Inc. | Method for sweeping solids or displacing a fluid in a wellbore |
US20150275644A1 (en) | 2014-03-28 | 2015-10-01 | Schlumberger Technology Corporation | Well treatment |
CA2852199A1 (en) | 2014-04-04 | 2015-10-04 | Oil Chem Technologies, Inc. | Method for in-situ solid particles formation and applications thereof |
US9676993B2 (en) | 2014-04-22 | 2017-06-13 | Baker Hughes Incorporated | Folded or crumpled proppants with increased material strength for hydraulic fracturing, gravel packing and frac packing |
US9790422B2 (en) | 2014-04-30 | 2017-10-17 | Preferred Technology, Llc | Proppant mixtures |
CA2946847C (en) | 2014-06-19 | 2019-02-26 | Halliburton Energy Services, Inc. | Methods and compositions for providing proppant suspension and consolidation in subterranean treatment operations |
US9963292B2 (en) | 2014-06-19 | 2018-05-08 | Scott Bromley | Storage bin and method of use |
US20150369027A1 (en) | 2014-06-24 | 2015-12-24 | Schlumberger Technology Corporation | Well treatment method and system |
MX2017003462A (es) | 2014-09-17 | 2017-07-28 | Carbo Ceramics Inc | Agente de tratamiento quimico que contiene agentes apuntalantes o proppant infundido y recubierto y metodos de para usarlo. |
US9938431B2 (en) | 2014-09-26 | 2018-04-10 | The Chemours Company Fc, Llc | Use of non-fluorinated or partially fluorinated urethanes in coatings |
US20160108713A1 (en) | 2014-10-20 | 2016-04-21 | Schlumberger Technology Corporation | System and method of treating a subterranean formation |
US20160137904A1 (en) | 2014-10-30 | 2016-05-19 | Preferred Technology, Llc | Proppants and methods of use thereof |
CA2911139C (en) | 2014-11-05 | 2023-07-25 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Shape memory polymer proppants and methods of making shape memory polymer proppants for application in hydraulic fracturing treatments |
CN107002487B (zh) | 2014-12-05 | 2020-06-30 | 陶氏环球技术有限责任公司 | 包含油井处理剂涂料的支撑剂 |
US10035950B2 (en) | 2014-12-29 | 2018-07-31 | Carbo Ceramics, Inc. | Compositions and methods for improving proppant conductivity |
WO2016109193A1 (en) | 2014-12-30 | 2016-07-07 | Georgia-Pacific Chemicals Llc | Coated proppants containing hyperbranched polyurethane coatings and methods for using same |
WO2016112013A1 (en) | 2015-01-06 | 2016-07-14 | Lawter, Inc. | Polyamide resins for coating of sand or ceramic proppants used in hydraulic fracturing |
US9617465B2 (en) | 2015-01-09 | 2017-04-11 | Halliburton Energy Services, Inc. | Leakoff mitigation treatment utilizing self degrading materials prior to re-fracture treatment |
US9896620B2 (en) * | 2015-03-04 | 2018-02-20 | Covestro Llc | Proppant sand coating for dust reduction |
US10703964B2 (en) | 2015-03-30 | 2020-07-07 | Dow Global Technologies Llc | Proppant coating having preformed isocyanurate |
AR104606A1 (es) | 2015-05-13 | 2017-08-02 | Preferred Tech Llc | Partícula recubierta |
US20180142137A1 (en) | 2015-05-27 | 2018-05-24 | Lubrizol Oilfield Solutions, Inc. | Aggregating compositions, modified particulate solid compositions, and methods for making and using same |
US20160347991A1 (en) | 2015-06-01 | 2016-12-01 | Baker Hughes Incorporated | Self-breaking fracturing fluids and methods for treating hydrocarbon-bearing formations |
US20160347985A1 (en) | 2015-06-01 | 2016-12-01 | Baker Hughes Incorporated | Fluids and methods for treating hydrocarbon-bearing formations |
-
2017
- 2017-08-22 US US15/682,595 patent/US10385261B2/en not_active Expired - Fee Related
-
2018
- 2018-08-20 WO PCT/US2018/047021 patent/WO2019040347A1/en active Application Filing
- 2018-08-20 MX MX2020001817A patent/MX2020001817A/es unknown
- 2018-08-20 CA CA3073315A patent/CA3073315A1/en active Pending
- 2018-08-20 CN CN201880053321.4A patent/CN110997863A/zh active Pending
-
2019
- 2019-07-02 US US16/459,720 patent/US10647911B2/en active Active
-
2020
- 2020-02-12 US US16/788,622 patent/US10851291B2/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20150034314A1 (en) * | 2013-08-01 | 2015-02-05 | Bayer Materialscience Llc | Coated particles and methods for their manufacture and use |
CN105793385A (zh) * | 2013-08-30 | 2016-07-20 | 优选技术有限责任公司 | 具有复合材料涂层的支撑剂 |
US20160333535A1 (en) * | 2015-05-15 | 2016-11-17 | Bayer Materialscience Llc | Free-flowing coated rubber particles, methods for their production and use |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115678534A (zh) * | 2021-07-29 | 2023-02-03 | 中国石油化工股份有限公司 | 支撑剂及其制备方法和应用 |
CN115678534B (zh) * | 2021-07-29 | 2024-03-19 | 中国石油化工股份有限公司 | 支撑剂及其制备方法和应用 |
Also Published As
Publication number | Publication date |
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CA3073315A1 (en) | 2019-02-28 |
US10385261B2 (en) | 2019-08-20 |
US20190330521A1 (en) | 2019-10-31 |
MX2020001817A (es) | 2020-07-13 |
WO2019040347A1 (en) | 2019-02-28 |
US20200181483A1 (en) | 2020-06-11 |
US20190062622A1 (en) | 2019-02-28 |
US10647911B2 (en) | 2020-05-12 |
US10851291B2 (en) | 2020-12-01 |
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