WO2015193909A1 - Composés d'amide/ester d'organosilane quaternaire et leurs utilisations - Google Patents

Composés d'amide/ester d'organosilane quaternaire et leurs utilisations Download PDF

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WO2015193909A1
WO2015193909A1 PCT/IN2015/000230 IN2015000230W WO2015193909A1 WO 2015193909 A1 WO2015193909 A1 WO 2015193909A1 IN 2015000230 W IN2015000230 W IN 2015000230W WO 2015193909 A1 WO2015193909 A1 WO 2015193909A1
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formula
acid
substituted
unsubstituted
composition
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PCT/IN2015/000230
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Mikhil Ranka
Ajay Ranka
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Ranka, Seema Ajay
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L95/00—Compositions of bituminous materials, e.g. asphalt, tar, pitch
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2555/00—Characteristics of bituminous mixtures
    • C08L2555/20—Mixtures of bitumen and aggregate defined by their production temperatures, e.g. production of asphalt for road or pavement applications
    • C08L2555/24—Asphalt produced between 100°C and 140°C, e.g. warm mix asphalt
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2555/00—Characteristics of bituminous mixtures
    • C08L2555/40—Mixtures based upon bitumen or asphalt containing functional additives
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A30/00—Adapting or protecting infrastructure or their operation
    • Y02A30/30—Adapting or protecting infrastructure or their operation in transportation, e.g. on roads, waterways or railways

Definitions

  • the present disclosure generally relates to a class of reactive silane compounds, and more specifically to quaternary organosilane-ester/amide compounds or mixture of such compounds, which have a variety of uses including additives for warm-mix asphalt formulations.
  • the present disclosure also provides a process for preparing the quaternary organosilane-ester/amide compounds or mixtures thereof.
  • the prepared HMA is compacted for surface paving at around 120- 135°C.
  • many technologies have evolved to prepare the asphalt/bitumen mix at lower temperatures.
  • U.S. Patent No. 7,297,204 is directed to mixing at a lower temperature and to ensure the workability (flow) and compact ability at a reduced temperature (e.g., 15-35°C lower than customary) at the paving stage.
  • emulsifiers and additives have been added to improve wetting & lubrication to achieve the objective of 15-35°C lower temperature asphalt mix preparation and compaction.
  • Typical chemical additive compositions that are known in the art include mixtures of amines, polyamines, amidoamines, Fischer Tropsch waxes, polyethylene waxes, tall oil, castor oil and other similar fatty acids and their derivatives.
  • estolides oligoester compositions derived from fats and oils.
  • An estolide structure is identified by an ester linkage of one fatty acyl molecule to the alkyl backbone of another fatty acid fragment.
  • the generic formula (Formula I) below depicts the basic nomenclature of an estolide illustrating the ester linkage, a capping fatty acid, and the estolide number (EN). The EN indicates the extent of oligomerization of the molecule.
  • estolides there are a broad range of estolides, both natural and synthetic, that have been found to serve as emulsifiers, rheology modifiers and lubricating agents in cosmetics, inks, textiles etc.
  • US patent 4,428,850 describes the incorporation of estolides in railway diesel engine lubricating oil for improved defoaming
  • US patent 6,3 1 6,649 describes biodegradable estolides for use as a lubricant base stock.
  • Y is independently selected from moieties that hydrolyze to liberate a mono or poly hydroxy compound, OH or a halogen;
  • R 2 and R 3 are independently selected from a straight chain or branched, substituted or unsubstituted C 1.C4 alkyl;
  • W ) , W 2 , and W 3 are independently selected from a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C 1 -C4 hydrocarbon;
  • Z is a bond (i.e., W i is directly attached to W 2 ), O, o NR;
  • R is a C 1-C4 alkyl or H
  • X is selected from O or NH
  • a is an integer from 1 to 3 (e.g., 1 , 2, or 3);
  • M is a counter anion
  • R4 is selected from a fatty acid group or a derivative thereof of the formula R'-COOH , wherein R' is a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C ] -C 23 hydrocarbon, Formula 111 or Formula IV Formula III Formula IV wherein:
  • A] and A 2 are independently selected from a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted Ci-C 2 i hydrocarbon;
  • R 5 is a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C i -C 2 3 hydrocarbon;
  • R 6 and R are independently selected from H or a saturated or unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C1-C21 hydrocarbon;
  • p is a value selected from 1 to 10 (e.g., 1 , 2, 3, 4, 5, 6, 7, 8, 9, 10); in certain preferred embodiments p comprises a value from 1 to 5.
  • the present disclosure provides a process for preparing compounds (or mixtures thereof) of Formula II.
  • the present disclosure provides an asphalt composition, comprising: an asphalt binder; an aggregate; and from 0.01 % to 20 % wt of at least one compound according to claim I based on the weight of the asphalt binder.
  • the present disclosure provides a water-based asphalt mineral composition and a foamed asphalt binder composition.
  • the present disclosure provides a process for the preparation of an asphalt composition and a foamed asphalt binder composition
  • Halo or "Halogen”, alone or in combination with any other term means halogens such as chloro (CI), bromo (Br), fluoro (F) and iodo (I).
  • alkyl refers to a saturated or an unsaturated, cyclic, straight chain or branced, substituted or unsubstituted hydrocarbon chain having 1 , 2, 3, 4, 5, 6, 7, 8, 9, 10, 1 1 , 12, 13, 14, 15, 16, 17, 18, 1 9, 20, 21 , 22 or 23.
  • This term is exemplified by groups such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, t-butyl n-hexyl, n- decyl, tetradecyl, and the l ike which optionally carries one or more substituents, preferably one to two, each independently selected from CI, Br, F, 1, OH.
  • M refers to counter anion
  • the present disclosure provides quaternary organosilane- ester/amide compounds or mixture of such compounds, which are useful in a variety of applications including use as additives for warm-mix asphalt formulations.
  • Compounds or mixtures thereof, in accordance with certain embodiments of the present disclosure serve the dual purpose of significantly increasing the moisture resistance of asphalt pavements, while simultaneously decreasing the mixing, laying and compacting effort to enable warm-mix asphalt (WMA) preparation.
  • WMA warm-mix asphalt
  • Compounds or mixtures in accordance with embodiments of the present disclosure have been found to effectively improve mixing and compaction of pavements at temperatures lower than those associated with conventional hot mix asphalt (HMA), while simultaneously improving moisture resistance of the pavements.
  • the present disclosure provides a class of reactive quaternary organosilane-ester/amide compounds or mixtures thereof that can be derived from fatty acids or estolides.
  • Compounds and mixtures thereof in accordance with certain embodiments of the present disclosure not only serve as effective chemical additives for warm-mix asphalt (WMA) preparations by significantly improving the wetting and coating during asphalt mix preparation, but also significantly improve the moisture resistance of the final pavement by forming a chemically bound organic layer on the aggregate surface.
  • WMA warm-mix asphalt
  • the chemically bound organic layer makes the aggregate surface significantly more compatible with the incoming bitumen, thereby forming a stronger aggregate- bitumen interface that is less susceptible to moisture ingress.
  • Y is independently selected from moieties that hydrolyze to l iberate a mono or poly hydroxy compound, OH or a halogen;
  • Ri R.2 and 3 are independently selected from a straight chain or branched, substituted or unsubstituted C ]_C 4 alkyl;
  • W ] , W 2 , and W3 are independently selected from a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C 1 -C4 hydrocarbon; Z is a bond (i.e., Wj is directly attached to W 2 ), O, or NR.
  • R is a Ci.C 4 alkyl or H
  • X is selected from O or NH
  • a is an integer from 1 to 3 (e.g., 1 , 2, or 3);
  • M is a counter anion
  • R 4 is selected from a fatty acid group or a derivative thereof of the formula R'-COOH, wherein R' is a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted Ci-C 23 hydrocarbon, Formula III or Formula IV
  • a I and A 2 are independently selected from a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C i-C 2 i hydrocarbon;
  • R is a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C 1 -C23 hydrocarbon;
  • R.6 and R 7 are independently selected from H or a saturated or unsaturated, cyclic, straight chain or branched, substituted or unsubstituted Ci-C 2 i hydrocarbon;
  • p is a value selected from 1 to 10 (e.g., 1 , 2, 3, 4, 5, 6, 7, 8, 9, 1 0); in certain preferred embodiments p comprises a value from 1 to 5.
  • quaternary organosilane-ester/amide compounds (or mixtures thereof) of Formula II are provided as follows:
  • Y is independently selected from the group consisting of -OR, -0(CH 2 CH 2 0) 0 H, - 0(CH 2 CHCH 3 0) 0 H, (CH 3 OCH 2 CH 2 0), (CH 3 CH 2 OCH 2 CH 2 0), and a halogen; wherein o is an integer from 1 to 10.
  • Ri R 2 and R 3 are independently selected from a straight chain or branched, substituted or unsubstituted C].C 4 alkyl, wherein Ri , R 2 and R 3 are optionally substituted wiuV halogen, OH;
  • Wi , W 2 , and W 3 are independently selected from a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C 1 -C 4 hydrocarbon;
  • Z is a bond, O, or NR
  • R is a Ci.C 4 alkyl or H
  • X is selected from O or NH
  • a is an integer from 1 to 3 (e.g., 1 , 2, or 3);
  • M is a counter anion, selected from the group consisting of chloride, bromide, fluoride, and iodide;
  • R 4 is selected from a fatty acid group or a derivative thereof of the formula R'-COOH, wherein R' is a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C 1 -C23 hydrocarbon, Formula I I I or Formula IV
  • a I and A 2 are independently selected from a saturated or an unsaturated, cycl ic, straight chain or branched, substituted or unsubstituted C ] -C 2 i hydrocarbon;
  • R5 is a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C
  • R 6 and R 7 are independently selected from H or a saturated or unsaturated, cyclic, straight chain or branched, substituted or unsubstituted Ci-C 2 i hydrocarbon;
  • p is a value selected from 1 to 10 (e.g., 1 , 2, 3, 4, 5, 6, 7, 8, 9, 10); in certain preferred embodiments p comprises a value from 1 to 5.
  • quaternary organosilane-ester/amide compounds (or mixtures thereof) of Formula II are provided as follows:
  • Y is independently selected from moieties that hydrolyze to liberate a mono or poly hydroxy compound, OH or a halogen
  • Ri R 2 and R 3 are independently selected from a straight chain or branched, substituted or unsubstituted Ci.C 4 alkyl wherein Ri , R 2 and R 3 are optionally substituted with halogen, OH;
  • Wi , W 2 , and W 3 are independently selected from -(CH 2 ) n - , where n is 1 , 2, 3, or 4;
  • Z is a bond, O, or NR
  • R is a C 1 -C4 alkyl or H
  • X is selected from O or NH
  • a is an integer from 1 to 3 (e.g., 1 , 2, or 3);
  • M is a counter anion, selected from the group consisting of chloride, bromide, fluoride and iodide;
  • R 4 is selected from a fatty acid group or a derivative thereof of the formula R'-COOH, wherein R' is a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C 1 -C23 hydrocarbon, Formula III or Formula IV
  • a I and A 2 are independently selected from a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C i-C 2 i hydrocarbon;
  • R5 is a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted Ci -C 23 hydrocarbon;
  • R 6 and R 7 are independently selected from H or a saturated or unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C] -C 2 i hydrocarbon;
  • p is a value selected from 1 to 10 (e.g., 1 , 2, 3, 4, 5, 6, 7, 8, 9, 10) in certain preferred embodiments p comprises a value from 1 to 5.
  • quaternary organosilane-ester/amide compounds (or mixtures thereof) of formula II are provided as follows:
  • Y is independently selected from CI or OR
  • Ri R 2 and R 3 are independently selected from a straight chain or branched, substituted or unsubstituted C
  • W ) , W 2 , and W 3 are independently selected from a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C 1 -C4 hydrocarbon;
  • Z is a bond, O, or NR
  • R is a C 1.C4 alkyl or H
  • X is selected from O or NH; a is an integer from 1 to 3 (e.g., 1 , 2, or 3);
  • M ⁇ is a counter anion, selected from the group consisting of chloride, bromide, fluoride and iodide;
  • R 4 is selected from a fatty acid group or a derivative thereof of the formula R'-COOH, wherein R' is a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted Ci-C 23 hydrocarbon, Formula III or Formula IV
  • Ai and A 2 are independently selected from a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C I -C 2 I hydrocarbon;
  • R 5 is a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted Ci-C 23 hydrocarbon;
  • Re and R 7 are independently selected from H or a saturated or unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C
  • p is a value selected from 1 to 10 (e.g., 1 , 2, 3, 4, 5, 6, 7, 8, 9, 10); in certain preferred embodiments p comprises a value from 1 to 5.
  • quaternary organosilane-ester/amide compounds (or mixtures thereof) of formula II are provided as follows:
  • Y is independently selected from CI or OR
  • R 2 and R 3 are independently selected from a straight chain or branched, substituted or unsubstituted C1.C4 alkyl wherein Rj , R 2 and R 3 are optionally substituted with halogen, OH;
  • Wi , W 2 , and W 3 are independently selected from -(CH 2 ) n - , where n is 1 , 2, 3, or 4; Z is a bond (i.e., Wi is directly attached to W 2 ), O, or NR;
  • R is a C i.C 4 alkyl or H
  • X is selected from O or NH
  • a is an integer from 1 to 3 (e.g., 1 , 2, or 3);
  • M is a counter anion, selected from the group consisting of chloride, bromide, fluoride and iodide;
  • R 4 is selected from a fatty acid group or a derivative thereof of the formula R'-COOH, wherein R' is a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C i -C 23 hydrocarbon, Formula III or Formula IV
  • a i and A 2 are independently selected from a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C 1 -C21 hydrocarbon;
  • R5 is a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C
  • R 6 and R 7 are independently selected from H or a saturated or unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C 1 -C21 hydrocarbon;
  • the quaternary organosilane-ester/amide compounds can be formed from fatty acids (or derivatives thereof) and/or estolides with a free acid group (or derivatives thereof), wherein the fatty acid or its derivative and/ or the estolide or its derivative are treated with a functional ized amine species (preferably a tertiary amine species) to form an amine adduct.
  • a functional ized amine species preferably a tertiary amine species
  • the tertiary amine functional group of the amine adduct can be subsequently quaternized using suitable organosi lanes. If the amine species are not tertiary in nature, they can be alkylated to tertiary state via common alkylating agents at any stage prior to the quaternization.
  • a tertiary amine can be obtained from a secondary amine or a primary amine.
  • Non-limiting examples include monoethanolamine, diethanolamine, monomethylethanolamine, 2- (2aminoethoxy)ethanol, aminoethylethanolamine.
  • Non-limiting examplesof tertiary amines include triethanolamine,2- ⁇ [2-(Dimethylamino)ethyl]methylamino ⁇ ethanol, dimethylethanolamine, N-methyldiethanolamine, dimethylaminopropylamine, dimethylaminobutylamine, aminopropylmorpholine, N,Ndimethyl-2(2- aminoethoxy)ethanol, alkanolamines and substituted propylamines.
  • Non-limiting examples of organosilane are 3-chloropropyltrimethoxysilane,3- chloropropyltriethoxysilane,(3-chloropropyl)dimethoxy(methyl)silane,(3- chloropropyl)diethoxy(methyl)silane,chIoromethyltrimethoxysilane,chloromethyltrietho xysilane,chloromethylmethyldimethoxysilane,chloromethyldiethoxysilane and the like
  • the fatty acid compound or a fatty acid group in accordance with embodiments of the present disclosure can be of the form of Formula II I, Formula IV or R'-COOH, wherein R' is a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C 1 -C23 hydrocarbon.
  • R' is a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C 1 -C23 hydrocarbon.
  • the term "fatty acid compound or fatty acid group” is intended to cover fatty acids per se or derivatives thereof.
  • derivative as used herein, in accordance with embodiments of the present disclosure, is to be understood as a compound wherein the -COOH group of the fatty acid is.
  • Non-limiting examples of fatty acid derivatives include acid chlorides, esters, anhydrides and amides. More specifically, the fatty acid compound or the fatty acid group, or derivatives thereof contain groups which are amenable to typical reactions such as esterification and amidation.
  • Non-limiting examples of fatty acids include ricinoleic acid, 12-hydroxystearic acid, meadowfoam oil, vernolic acid, lesquerella oil, epoxystearic acid, 2-hydroxy-9- cisoctadeconoic acid, l O-hydroxy-2-decenoic acid, 9, 10- dihydroxyoctadecanoic acid, phloinolic acid, lauric acid, stearic acid, and palmitic acid, and combinations thereof, or derivatives thereof.
  • Estolides are oligoesters derived from fats and oils. As noted above, the estolide structure is identified by an ester linkage of one fatty acyl molecule to the alkyl backbone of another fatty acid fragment. In accordance with certain embodiments of the present disclosure, the estolide is a compound according to Formula 111 or Formula IV formed by condensation of an oil, or a fatty acid or its derivative, or mixtures thereof,
  • Ai and A 2 are independently selected from a saturated or an unsaturated, cycl ic, straight chain or branched, substituted or unsubstituted C i-C? i hydrocarbon;
  • R 5 is a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C ] -C23 hydrocarbon;
  • R 6 and R 7 are independently selected from a saturated or unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C ] -C 2 i hydrocarbon;
  • p is a value selected from 1 to 1 0 (e.g., 1 , 2, 3, 4, 5, 6, 7, 8, 9, 1 0)in certain preferred embodiments p comprises a value from 1 to 5.
  • quaternary organosilane-ester/amide compounds (or mixtures thereof) of Formula 11 are provided as follows:
  • Y is independently selected from moieties that hydrolyze to liberate a mono or polyhydroxy compound, OH or a halogen
  • R 2 and R 3 are independently selected from a straight chain or branched, substituted or unsubstituted Ci_C 4 alkyl, wherein R] , R 2 and R 3 are optionally substituted with halogen, OH;
  • Wi , W 2 , and W 3 are independently selected from a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C 1 -C4 hydrocarbon;
  • Z is R
  • R is a C ,_C 4 alkyl or H
  • X is selected from O or NH
  • a is an integer from 1 to 3 (e.g., 1 , 2, or 3);
  • M is a counter anion, selected from the group consisting of chloride, bromide, fluoride and iodide;
  • R 4 is selected from a fatty acid group or a derivative thereof of the formula R'-COOH, wherein R' is a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C 1 -C23 hydrocarbon, Formula 111 or Formula IV
  • and A 2 are independently selected from a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted Ci -C 2 j hydrocarbon;
  • R 5 is a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted Ci -C 23 hydrocarbon;
  • R 6 and R 7 are independently selected from H or a saturated or unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C i -C 2 i hydrocarbon;
  • p is a value selected from 1 to 10 (e.g., 1 , 2, 3, 4, 5, 6, 7, 8, 9, 10); in certain preferred embodiments p comprises a value from 1 to 5.
  • quaternary organosilane-ester/amide compounds (or mixtures thereof) of Formula II are provided as follows:
  • Y is independently selected from moieties that hydrolyze to liberate a mono or poly hydroxy compound, OH or a halogen;
  • R 2 and R 3 are independently selected from a straight chain or branched, substituted or unsubstituted C 1 .C4 alkyl wherein R] , R 2 and R 3 are optionally substituted with halogen, OH;
  • W i , W 2 , and W 3 are independently selected from a saturated or an unsaturated, cycl ic, straight chain or branched, substituted or unsubstituted C
  • Z is O
  • X is selected from O or NH
  • a is an integer from I to 3 (e.g., 1 , 2, or 3); M is a counter anion, selected from the group consisting of chloride, bromide, fluoride and iodide;
  • R4 is selected from a fatty acid group or a derivative thereof of the formula R'-COOH, wherein R' is a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C1 -C23 hydrocarbon, Formula III or Formula IV
  • Ai and A 2 are independently selected from a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C1 -C21 hydrocarbon;
  • R5 is a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C 1 -C23 hydrocarbon, or OH;
  • R 6 and R 7 are independently selected from H or a saturated or unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C i -C 2
  • p is a value selected from 1 to 10 (e.g., 1 , 2, 3, 4, 5, 6, 7, 8, 9, 10); in certain preferred embodiments p comprises a value from 1 to 5.
  • the fatty acids and/or estolides can have hydroxy, epoxy and other substitutions, or unsaturation, part of the hydrocarbon chain that does not participate in the previously described reaction scheme, but are amenable to additional functional ization nonetheless.
  • Such additional functionaHzation of the fatty acid or estoiide can be carried out at any suitable stage during the synthesis.
  • Two exemplary generic structures of quaternary organosilane-ester/amide compounds in accordance with certain embodiments of the present disclosure include:
  • R is a Ci-C 4 alkyl or H
  • R 4 is a moiety selected from a fatty acid group or a derivative thereof of the formula R'-COOH, wherein R' is a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C]-C 23 hydrocarbon;
  • the present disclosure also provides a process for preparing quaternary organosilane- estolide compounds of Formula II, or mixtures thereof.
  • preparation of quaternary organosilane- estolide compounds of Formula II, or mixtures thereof can be accomplished by treating (i) a fatty acid group or a derivative thereof of the formula R'-COOH, wherein R' is a saturated or an unsaturated, cycl ic, straight chain or branched, substituted or unsubstituted C 1 -C23 hydrocarbon; or (ii) an estolide with an amine (preferably a tertiary amine) to obtain an am ine adduct.
  • the amine adduct can then be reacted with an organosilane to obtain a quaternary organosilane- ester/amide compound of Formula II, or mixtures thereof.
  • amine species that are not tertiary in nature can also be employed by alkylating to tertiary amine by common alkylating agents at any stage prior reacting with the organosilane to obtain the quaternary organosilane- ester/amide compound.
  • Certain embodiments of the present disclosure provide a process for preparing a quaternary organosilane-estolide compound of Formula II, or mixtures thereof, wherein the estolide used in the process is a compound of Formula III or Formula IV:
  • A] and A 2 are independently selected from a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted Ci-C 2 j hydrocarbon;
  • R.5 is a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted Ci-C 2 3 hydrocarbon;
  • R 6 and R 7 are independently selected from a saturated or unsaturated, cyclic, straight chain or branched, substituted or unsubstituted Ci-C 2 i hydrocarbon;
  • p is a value selected from 1 to 10.
  • the estolide is obtained by condensing an oil, or a fatty acid or its derivative, or mixtures thereof.
  • the present disclosure provides a process for preparing a quaternary organosilane estolide compound of Formula I I, or mixtures thereof, comprising the steps of treating (i) a fatty acid selected from the group consisting of ricinoleic acid, 12-hydroxystearic acid, meadowfoam oil, vernolic acid, lesquerella oil, epoxystearic acid, 2-hydroxy-9-cisoctadeconoic acid, 10-hydroxy-2- decenoic acid, 9, 1 0- dihydroxyoctadecanoic acid, ph loinolic acid, lauric acid, stearic acid, and palmitic acid, derivatives thereof, and combinations thereof; or (i i) an estolide with an amine (preferably tertiary amine) to obtain an amine adduct; and reacting the amine adduct with an organosilane to obtain a quaternary organosilane- ester/amide compound of Formula II,
  • a process for preparing a quaternary organosilane- estolide compound of Formula II, or mixtures thereof is provided.
  • the process can comprise the steps of treating (i) a fatty acid group or a derivative thereof of the formula R'-COOH, wherein R' is a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C 1 -C23 hydrocarbon; or (ii) an estolide with a tertiary amine obtained from a secondary amine or a primary amine selected from monoethanolamine, diethanolamine, monomethylethanolamine, 2- (2aminoethoxy)ethanol, aminoethylethanolamine, to form an amine adduct; and reacting the amine adduct with an organosilane to obtain a quaternary organosilane- ester/amide compound of Formula II, or mixtures thereof.
  • a process for preparing a quaternary organosilane- estolide compound of Formula II, or mixtures thereof comprising the following steps: treating (i) a fatty acid group or a derivative thereof of the formula R'-COOH, wherein R' is a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C 1 -C23 hydrocarbon; or (ii) an estolide, with an amine (preferably tertiary amine) to form an amine adduct; and reacting the amine adduct with an organosilane selected from the group consisting of 3- chloropropyltrimethoxysilane, 3-chloropi pryltriethoxysilane, (3- chloropropyI)dimethoxy(methyl)si lane, (3-chloropropyl)diethoxy(methyl)silane, chloromethyltrimethoxysi
  • a process for preparing a quaternary organosilane- estol ide compound of formula I I, or mixtures thereof comprising the following steps: treating (i) a fatty acid group or a derivative thereof of the formula R'-COOH, wherein R' is a saturated or an unsaturated, cyclic, straight chain or branched, substituted or unsubstituted C 1 -C23 hydrocarbon; or (i i) an estolide, with a tertiary amine selected from the group consisting of triethanolamine, dimethylethanolamine, N-methyldiethanoiamine, dimethylaminopropylamine, aminopropylmorpholine,N,Ndimethyl-2(2-aminoethoxy)ethano) and tetramethyldipropylenetriamine to form an amine adduct; and reacting the amine adduct with an organosilane to obtain a quaternary organo
  • Processes in accordance with certain embodiments of the present disclosure yield not only a single type of a quaternary organosilane- ester/amide compound (e.g., a single resultant compound), but mixtures of such compounds according to Formula II.
  • a quaternary organosilane- ester/amide compound e.g., a single resultant compound
  • the present disclosure covers varying mixtures of quaternary organosilane- ester/amide compounds of formula II (and methods of synthesizing/producing such mixtures), besides a single type (compound) of quaternary organosilane- ester/amide compound formed by the processes the preparation.
  • the present disclosure provides quaternary organosilane- ester/amide compounds of Formula II (or mixtures thereof) used in asphalt formulations/compositions.
  • the quaternary organosilane- ester/amide compounds of the present disclosure beneficially provide enhanced lubricity and moisture resistance when incorporated into asphalt pavement formulations. Characteristics of enhanced lubricity can be recognized via improvement in ease of mixing of asphalt binder and aggregate, as well as, via improved compaction and densification at lower than conventional hot mix temperatures, improved moisture resistance can be recognized via higher adhesion of asphalt binder (e.g., bitumen) in a standard water boil test, as well as, via improved Marshall Stability of the asphalt pavement.
  • asphalt binder e.g., bitumen
  • the present disclosure provides and asphalt composition, suitable for a wide variety of asphalt paving applications, comprising: (i) an asphalt binder, (ii) an aggregate (or mixture of aggregates), and (iii) from 0.01 % to 20 % wt. of at least one quaternary organosilane- ester/amide compound of Formula I I, or mixtures thereof based on the weight of the asphalt binder.
  • the amount of the at least one quaternary organosilane- ester/amide compound of Formula II, or mixtures thereof can comprise from of at least about any of the following: 0.01 %, 0.05%, 1 %, and 2% wt.
  • the amount of the at least one quaternary organosilane- ester/amide compound of Formula II can comprise from about 0.01 % to 10% wt. based on the weight of the asphalt binder.
  • the present disclosure also provides a water-based asphalt mineral compositions, suitable for a wide variety of asphalt paving applications, comprising: (i) an emulsion of an asphalt binder dispersed in water; (ii) a mineral aggregate (or mixture of aggregates); and (iii) from 0.01 % to 20 % wt. of at least one quaternary organosilane- ester/amide compound of Formula II, or mixtures thereof based on the weight of the asphalt binder.
  • the amount of the at least one quaternary organosilane- ester/amide compound of Formula II, or mixtures thereof can comprise from of at least about any of the following: 0.01 %, 0.05%, 1 %, and 2% wt. based on the weight of the asphalt binder; and/or at most about any of the following: 5%, 10% 15%, and 20 % wt. based on the weight of the asphalt binder. In certain embodiments, for instance, the amount of the at least one quaternary organosilane- ester/amide compound of Formula II, or mixtures thereof can comprise from about 0.01 % to 10% wt. based on the weight of the asphalt binder.
  • asphalt binder can include bitumen, natural asphalt, oil residue of paving grade, plastic residue from coal tar distillation, petroleum pitch and coal tar.
  • Asphalt binders are customarily used in paving constructions as a glue or binder for aggregate particles. That is, the asphalt binder is used to coat and bind aggregate particles together. These thermoplastic-like materials which soften when heated and harden upon cooling also exhibit viscoelastic properties (e.g., exhibit the mechanical characteristics of viscous flow and elastic deformation) over a certain temperature range.
  • Asphalt binders are highly complex and not well-characterized materials containing a variety of saturated and unsaturated aliphatic and aromatic compounds.
  • Asphalt binders typically contains about 80% by weight of carbon; around 10% hydrogen; up to 6% sulfur; small amounts of oxygen and nitrogen; and trace amounts of metals such as iron, nickel, and vanadium. The molecular weights of the constituent compounds range from several hundred to many thousands.
  • a wide variety of asphalt binders may be used in accordance with certain embodiments of the present disclosure.
  • any paving grade asphaltic binder satisfactory for preparing paving compositions is contemplated as being useful.
  • Paving grade asphaltic binders can have a wide range of penetration values ranging from as low as 30 or 40 dmm for the harder asphalts to 200 to 300 dmm at 25°C (100 g, sec.) for the softer asphalts.
  • the most widely used paving asphalt binders according to embodiments of the present disclosure generally have a penetration at 25°C of about 60 to 100 dmm (e.g., 60-70, 70-80, or 80- 100 dmm). In preferred embodiments, however, the asphalt binder remains viscoelastic in all weather conditions.
  • the asphalt binder comprises "Bitumen's” and/or “Modified Bitumens” which as used herein, are those which exhibit rheological properties that are appropriate for paving application under specific climatic condition such as those which conform to the Strategic Highway Research Program (SHPvP)) pavement binder specification.
  • the bitumen component may be naturally occurring bitumens (such as Trinidad Lake Asphalt and the l ike), naturally occurring bituminous materials such as gilsonite and gi lsonite derivatives, or it can be produced by crude oil or petroleum pitches (such as asphalt) produced during cracking process and coal tar or blends of bituminous materials.
  • bitumen may also conform to specification of viscosity graded and/or penetration graded bitumens.
  • Additives which are traditionally added to bitumen to produce a modified bitumen meeting performance-grade standards (such as SHRP) are suitable for use in certain embodiments according to the present disclosure.
  • Such additives include, but are not limited to, natural rubbers, synthetic rubbers, plastomers, thermoplastic resins, thermosetting resins, elastomers, and combinations thereof.
  • bitumens used in processes according to embodiments of the present disclosure can also contain recycled crumb rubber from recycled tires.
  • the modified bitumen can contain at least one member selected from the group consisting of sulfur, sulfur-containing crosslinkers, acid modifiers such as tall oil acids, tall oil pitches, and phosphoric acid derivatives and combinations thereof. It is well within the ability of a skilled artisan to produce modified bitumen containing the noted additives.
  • additives traditionally employed in the production of bitumen include styrene-butadiene-rubber latex, polyisoprene latex, salts, and the like can be included in certain embodiments according to the present disclosure.
  • Such additives also include but are not limited to acid modifiers such as poly-phosphoric acid, crude and distil led tall oi l acids and tall oil pitches, and derivatives thereof, and wax modifiers such as ontan wax, beeswax, and Fisher-Tropsch waxes, etc.
  • anti-stripping additives like Lime or Hydrated Lime can be used either as powder mixed with aggregates or hydrated lime mixed with water and further mixed with aggregate to marinate at room temperature (e.g., for 10 to 30 hours, particularly 24 firs).
  • anti-stripping additives which are bitumen sol uble/dispersible such as organic amine or quaternary compounds, and silanes having a boiling point above 100°C can be used as anti- stripping additives in conjunction with quaternary organosilanes according to embodiments of the present disclosure and added to the asphalt binder (e.g., bitumen) or quaternary organosilane aqueous-based composition added to the asphalt binder for the formation of a stable foam that is exceptional for coating aggregates.
  • the asphalt binder e.g., bitumen
  • quaternary organosilane aqueous-based composition added to the asphalt binder for the formation of a stable foam that is exceptional for coating aggregates.
  • compounds such as an organic amine like di-methyl octadecyl amine, poly alkylene poly amines, fatty amido amines derived from Cj 2 -C 24 fatty acids, ethoxylated Ci 2 -C 2 4 monoalkyl amines, etc, quaternary compounds like tri-methyl octa decyl ammonium chloride, dimethyl ethoxy poly 12 hydroxy stearate ammonium di-methyl sulfate salt, etc, silanes such as tri-methoxy propyl silyl octa decyl ammonium chloride, di-methoxy, hydroxy ethoxy propyl silyl octa decyl ammonium chloride, etc.
  • the choice and use of these additives or others does not limit the spirit and scope of this disclosure
  • Aggregates or mineral aggregates are coarse particulate materials used in construction, including sand, gravel, crushed stone, soil, slag, recycled concrete, or mixtures thereof.
  • Mineral fillers are also aggregates which typically include dolomite, granites, river-bed crushed gravel, sandstone, limestone, basalt and other inorganic stones which can be added to the system.
  • the particular aggregates, sand, soils etc. used to form the asphalt formulations/compositions/asphalt -mineral compositions of the present disclosure are not critical as long as they have functional groups or reactive sites (e.g., silanol groups) on the surface that will bond with the silanols created by hydrolysis of the silane alkoxy groups of the compounds according to the present disclosure.
  • functional groups or reactive sites e.g., silanol groups
  • Aggregate used in paving materials and road construction, road rehabilitation, road repair, and road maintenance are derived from natural and synthetic sources.
  • aggregates are selected for asphalt paving appl ication based on a number of criteria, including physical properties, compatibi lity with the bitumen to be used in the construction process, availabi l ity, and abil ity to provide a finished pavement that meets the performance specifications of the pavement layer for the traffic projected over the design life of the project.
  • gradation refers to the percent of aggregate particles of a given size. For most load-bearing asphalt pavements, three gradations are common: dense-graded, gap-graded and open-graded.
  • Dense-graded aggregate exhibit the greatest mineral surface area (per unit of aggregate). Open-graded aggregate largely consist of a single, large-sized (e.g., around 0.375 to 1.0 inch) stone with very low levels (typically less than about two percent of the total aggregate) of fines (material less than 0.25 inch) or filler (mineral material less than 0.075 mm). Gap-graded aggregate fall between dense-graded and open-graded classes.
  • Reclaimed asphalt pavement (RAP) material generally reflects the gradation of the pavement from which the reclaimed material was obtained. If the original pavement was a dense-graded mix, the RAP generally will also be dense graded, although the filler content is generally observed to be lower than the design limits of the original aggregate specifications. Any such aggregates, alone or in combination, are suitable for certain embodiments of the present disclosure.
  • any aggregate which is traditionally employed in the production of bituminous/asphalt paving compositions can be used in certain embodiments according to the present disclosure, including dense-graded aggregate, gap-graded aggregate, open-graded aggregate, stone-matrix asphalt, recycled asphalt paving, and mixtures thereof.
  • aggregate which is not fully dried can be employed.
  • pre-treatment of the aggregate with an anti-stripping agent can optionally be performed.
  • pre-treatment of the aggregate with solution (preferably in water) including at least one quaternary organosilane- ester/amide compound of Formula II (or mixtures thereof) provides excellent anti-stripping performance.
  • the present disclosure provides a composition (e.g., an organosilane composition) comprising one or more quaternary organosilane-ester/amide compounds, in accordance with certain embodiments of the present disclosure (i.e., quaternary organosilane-ester/amide compounds disclosed herein), suspended or dissolved in a solvent.
  • a solvent can consist of water (i.e., water alone).
  • the solvent can comprise one or more organic co-solvents (in addition to water).
  • the organic co-solvents can include at least one alcohol.
  • suitable organic co-solvents should preferably not negatively impact the stability of the quaternary organosilane-ester/amide compounds.
  • Suitable co-solvents can generally include, but are not necessarily limited to, alcohols (preferably glycols), ketones, ester based solvents and polar acetate solvents.
  • Examples of alcohols include methanol, ethanol, benzyl alcohol, isopropanol and gylcols;
  • examples of glycols that can be used according to certain embodiments of the present disclosure include, but are not limited to, ethylene glycol, propylene glycol, ether alcohols such as ethylene glycol, ethylene glycol monoethyl ether and ethylene glycol monobutyl ether; dialkyl ethers of ethylene, ethylene glycolmonoethyl ether, ethylene glycol monobutyl ether, ethylene glycol dibutyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monohexyl ether acetate, propylene glycol monoethyl ether, and propylene glycol dibutyl ether; the mono- and dialkylethers of diethylene glycol such as diethylene glycol monoethyl ether, diethylene glycol dibutyl ether, diethylene glycol diethyl
  • ketones examples include, but are not limited to, acetone, acetophenone, butanone, cyclohexanone, ethyl isopropyl ketone, diacetone, isophorone, methyl isobutyl ketone, methyl isopropyl ketone, methylethyl ketone, methylamyl ketone, and 3-pentanone.
  • ester based solvents and acetate solvents examples include, but are not limited to, benzyl benzoate, butyl acetate, methyl acetate, ethyl acetate, n-propyl acetate, isobutyl acetate, isoamyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, amyl acetate, sec- butyl acetate, tert-butyl acetate, ethyl acetate, ethyl acetoacetate, methyl acetate propyl acetate, ethylene glycol monomethyl ether acetate, and ethylene glycol monoethyl ether acetate.
  • the composition can comprises from about 10 - 99 % by wt. (e.g., 10-95%, 20-90%, 40-80%, 45-75% by wt., etc.) of one or more quaternary organosilane-ester/amide compounds based on the total weight of the composition.
  • compositions including comprising one or more quaternary organosilane-ester/amide compounds in accordance with certain embodiments of the present disclosure (i.e., quaternary organosilane-ester/amide compounds disclosed herein), can be provided in the form of a gel.
  • the present disclosure provides a composition in the form of a powder.
  • Such powder compositions can include one or more quaternary organosilane-ester/amide compounds in accordance with certain embodiments of the present disclosure (i.e., quaternary organosilane-ester/amide compounds disclosed herein).
  • powder-based composition can comprise from about 10-100% (e.g., 25-100%, 45- 100%, 75- 100%, 95-100% by wt., etc.) by weight of one or more quaternary organosilane-ester/amide compounds based on the total weight of the composition.
  • the present disclosure provides a foamed asphalt binder composition
  • a foamed asphalt binder composition comprising: an asphalt binder, water, and one or more quaternary organosilane-ester/amide compounds in accordance with certain embodiments of the present disclosure (i.e., quaternary organosilane-ester/amide compounds disclosed herein).
  • the foamed asphalt binder compositions are in the form of an expanded foam (e.g., liquid foam).
  • the asphalt binder comprises bitumen.
  • the present disclosure provides a process for preparation of a foamed asphalt binder composition comprising steps of heating an asphalt binder to a temperature sufficient to obtain a flowable asphalt binder, adding an organosilane composition comprising one or more quaternary organosi lane-ester/amide compounds in an aqueous-based solvent to the flowable asphalt binder, and mixing the flowable asphalt binder and the organosilane composition at a temperature sufficient to provide a foamed asphalt binder composition.
  • the aqueous-based solvent comprises a mixture of water and at least one alcohol as described previously.
  • the aqueous-based solvent can also consist of water (i.e., water alone).
  • the step of adding the organosilane composition to the flowable asphalt binder comprises injecting the organosilane composition into the flowable asphalt binder.
  • the injecting step is performed via a nozzle, orifice, or valve.
  • the present disclosure provides a process for preparation of an asphalt composition comprising steps of heating an asphalt binder to a temperature sufficient to obtain a flowable asphalt binder, adding an organosilane composition comprising one or more quaternary organosi lane-ester/amide compounds (preferably in an aqueous-based solvent system) to the flowable asphalt binder, mixing the flowable asphalt binder and the organosilane composition at a temperature sufficient to provide a foamed asphalt binder composition, and mixing the foamed asphalt binder composition and aggregate to form the asphalt composition.
  • Basalt aggregates with gradation suitable for binder course was chosen. Standard aggregate and stone powder mix for these experiments with fol lowing composition - 20 mm passing 40%, 10 mm passing 30%, 6 mm passing 30% were used for preparation.
  • the mixes were mixed by hand.
  • the aggregate and mixing vessels were preheated in an oven at approximately 10°C higher than desired/recorded temperature to account for cooling during mixing at room temperature.
  • the bitumen was also heated to desired mixing temperature.
  • Product of Example 1 was added to the hot PG 64-22 bitumen, which was used at 4.6 % by weight of aggregate. Parameters of ease of mixing and time for complete coating were recorded and are shown in Table 1.
  • the "Ease of Mixing" was based on a scale ranging from 1 to 5, with 1 meaning easiest to freely mix by hand and a rating of 5 representative of extreme difficulty to freely mix by hand.
  • PG 64-22 asphalt samples were prepared to contain 0.0 % (Control mixture), 0.5 %, and 1 .0 % by weight of product of Example 1 .
  • the prepared asphalt was added at 4.6 % on weight of the basalt aggregates and mixed at 120°C.
  • the aggregate mix design was as in previous examples.
  • the mixtures were cured for 120 minutes at 135°C as standard conditioning time and then allowed to cool to room temperature, after which water boiling tests according to ASTM D3625 (2005) - Standard Practice for Effect of Water on Bituminous-Coated Aggregate Using Boiling Water were conducted. The results are shown in Table 3.

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Abstract

L'invention concerne des composés d'amide/ester d'organosilane quaternaire et leurs utilisations. La présente invention concerne, d'une manière générale, des composés d'amide/ester d'organosilane quaternaire de formule II, ou des mélanges de ceux-ci, [formule à insérer ici] Formule II. Les composés, ou des mélanges de ceux-ci, selon la présente invention, peuvent être utilisés en tant qu'additifs pour des compositions d'asphalte mélangé à chaud. La présente invention concerne également des procédés de préparation des composés de formule II, ou de mélanges de ceux-ci.
PCT/IN2015/000230 2014-06-18 2015-06-04 Composés d'amide/ester d'organosilane quaternaire et leurs utilisations WO2015193909A1 (fr)

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WO2018217749A1 (fr) * 2017-05-26 2018-11-29 Biosynthetic Technologies, Llc Liants d'asphalte et compositions bitumineuses comprenant des composés oligomères
CN109537089A (zh) * 2018-11-26 2019-03-29 福建省银河服饰有限公司 季铵化纳米太极石的制备方法、季铵化纳米太极石及改性聚酯纤维
CN111229118A (zh) * 2018-11-29 2020-06-05 中国石油化工股份有限公司 含脂肪酸型表面活性剂的混合体系及其制备方法
CN111229119A (zh) * 2018-11-29 2020-06-05 中国石油化工股份有限公司 含脂肪酸型表面活性剂的混合体系及其制备方法

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WO2008004242A2 (fr) * 2006-07-07 2008-01-10 Ranka, Seema, Ajay Procédés pour traiter des surfaces avec des compositions d'organosilicium ionisé
EP2414459A2 (fr) * 2008-12-22 2012-02-08 Ranka, Seema Ajay Compositions asphalte-minéral

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WO2008004242A2 (fr) * 2006-07-07 2008-01-10 Ranka, Seema, Ajay Procédés pour traiter des surfaces avec des compositions d'organosilicium ionisé
US20130008344A1 (en) * 2008-12-08 2013-01-10 Zydex Industries Asphalt-mineral compositions
EP2414459A2 (fr) * 2008-12-22 2012-02-08 Ranka, Seema Ajay Compositions asphalte-minéral

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018217749A1 (fr) * 2017-05-26 2018-11-29 Biosynthetic Technologies, Llc Liants d'asphalte et compositions bitumineuses comprenant des composés oligomères
CN109537089A (zh) * 2018-11-26 2019-03-29 福建省银河服饰有限公司 季铵化纳米太极石的制备方法、季铵化纳米太极石及改性聚酯纤维
CN109537089B (zh) * 2018-11-26 2021-06-25 福建省银河服饰有限公司 季铵化纳米太极石的制备方法、季铵化纳米太极石及改性聚酯纤维
CN111229118A (zh) * 2018-11-29 2020-06-05 中国石油化工股份有限公司 含脂肪酸型表面活性剂的混合体系及其制备方法
CN111229119A (zh) * 2018-11-29 2020-06-05 中国石油化工股份有限公司 含脂肪酸型表面活性剂的混合体系及其制备方法
CN111229119B (zh) * 2018-11-29 2021-08-03 中国石油化工股份有限公司 含脂肪酸型表面活性剂的混合体系及其制备方法
CN111229118B (zh) * 2018-11-29 2021-08-03 中国石油化工股份有限公司 含脂肪酸型表面活性剂的混合体系及其制备方法

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