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EP4149260A1 - Fil antisalissure et procédé de production de fil antisalissure et utilisation - Google Patents

Fil antisalissure et procédé de production de fil antisalissure et utilisation

Info

Publication number
EP4149260A1
EP4149260A1 EP21726318.5A EP21726318A EP4149260A1 EP 4149260 A1 EP4149260 A1 EP 4149260A1 EP 21726318 A EP21726318 A EP 21726318A EP 4149260 A1 EP4149260 A1 EP 4149260A1
Authority
EP
European Patent Office
Prior art keywords
yarn
antifouling
solution
tetrapodal
zno
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
Application number
EP21726318.5A
Other languages
German (de)
English (en)
Inventor
Anna Gapeeva
Haoyi Qiu
Martina Baum
Rainer Adelung
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Christian Albrechts Universitaet Kiel
Original Assignee
Christian Albrechts Universitaet Kiel
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Christian Albrechts Universitaet Kiel filed Critical Christian Albrechts Universitaet Kiel
Publication of EP4149260A1 publication Critical patent/EP4149260A1/fr
Pending legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
    • D01D1/00—Treatment of filament-forming or like material
    • D01D1/02—Preparation of spinning solutions
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/16—Heavy metals; Compounds thereof
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
    • D01D11/00—Other features of manufacture
    • D01D11/06—Coating with spinning solutions or melts
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F1/00—General methods for the manufacture of artificial filaments or the like
    • D01F1/02—Addition of substances to the spinning solution or to the melt
    • D01F1/10—Other agents for modifying properties
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/32—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond
    • D06M11/36—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond with oxides, hydroxides or mixed oxides; with salts derived from anions with an amphoteric element-oxygen bond
    • D06M11/44—Oxides or hydroxides of elements of Groups 2 or 12 of the Periodic Table; Zincates; Cadmates
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
    • D06M23/10—Processes in which the treating agent is dissolved or dispersed in organic solvents; Processes for the recovery of organic solvents thereof
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
    • D01F6/76—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from other polycondensation products

Definitions

  • the invention relates to a yarn with antifouling properties which is suitable for use under water, in particular when rearing aquatic organisms (aquaculture).
  • antifouling coatings are used to prevent undesirable fouling.
  • biocides such as the salts of pyrithione in this case, accumulate in the aquatic environment and are thus also absorbed by the breeding animals.
  • SFRC Silicone Fouling Release Coatings
  • a multicomponent fiber comprising starch and polymers as well as special configurations of the fibers is known, the fibers described therein being used to produce nonwoven webs and disposable articles, specifically a multicomponent fiber with a diameter of less than 100 ⁇ m is disclosed, comprising a destructured starch with a molecular weight in the range from 3000 g / mol to 2,000,000 g / mol and a thermoplastic polymer with a molecular weight of less than 500,000 g / mol, which is essentially compatible with the destructured starch, wherein the fiber has a configuration selected from the group consisting of core / sheath, matrix / fibrils, ribbon, segmented pie, side-by-side, and combinations thereof, and wherein each component of the multicomponent fiber comprises at least one of the destructured starch and / or the thermoplastic polymer .
  • EP 2 972255 B1 describes the approach of overcoming the problem by means of a release-free siloxane-urethane antifouling coating for maritime objects. Due to its stiffness, the coating is not well suited to coating difficult and flexible surfaces such as yarns or nets.
  • Another way of solving the problem of insufficient mechanical stability is to apply the fouling release coating based on siloxanes in a relatively thick (> 300 ⁇ m) spray process to an epoxy-coated substrate (US 2010/0069531 A1).
  • the problems in the prior art are essentially that the proposed antifouling coatings are in part not free of release and thus release accumulated biocides into the aquatic environment, especially during prolonged use, and on the other hand do not have the optimal durability, elasticity and abrasion resistance.
  • the durability, elasticity and abrasion resistance of an antifouling coating of yarns and nets represents a challenge that has not yet been optimally solved, because here a) the ratio of surface to volume of the coated body is particularly large compared to other maritime objects, b) it through frequent contact with the seabed, aquatic organisms or objects can result in abrasion, and c) furthermore, deformations of the yarn can occur as a result of pulling movements under water.
  • the present invention is based on the object of providing a new yarn with improved antifouling properties.
  • Another object of the invention is to provide a new yarn with improved antifouling properties that does not release any substances into the environment.
  • This object or objects is achieved with an antifouling yarn according to the main claim and an antifouling yarn production method for the yarn according to the independent claim and, in an extended manner, with the use of the antifouling yarn as a net yarn according to the further independent claim.
  • the antifouling yarn according to the invention comprises a core running along the running direction and a corona surrounding it, the corona containing poly- and oligo-siloxanes [SiR 2 0] n and tetrapodal zinc oxide (t-ZnO) and the core being composed of fibers and a
  • the matrix consists and the fibers are made up of organic polymers and the matrix also contains poly- and oligosiloxanes [SiR 2 0] n .
  • the mass fraction of tetrapodal zinc oxide (t-ZnO) on the corona is between 0.1 and 10%, preferably between 0.2 and 7.5%, particularly preferably between 0.3 and 5%.
  • the matrix also contains tetrapodal zinc oxide (t-ZnO) or fragments of tetrapodal zinc oxide.
  • t-ZnO tetrapodal zinc oxide
  • the organic polymers from which the fibers are built up are selected from the group of polyethylenes, polyesters and / or polyamides.
  • the manufacturing method according to the invention for the yarn according to the invention comprises the following steps: i. Providing a solution of a poly- and / or oligo-dialkylsiloxane, a silane crosslinker and tetrapodal zinc oxide (t-ZnO) in a non-polar or slightly non-polar solvent as solution A; ii. Dipping conventional yarn in solution A; iii. Mechanical fulling of the yarn in solution A; iv. Allowing solution A to rest with the kneaded yarn; v. Removing the impregnated yarn from solution A; vi. Drying of the impregnated yarn.
  • t-ZnO tetrapodal zinc oxide
  • the poly- and / or oligo-dialkylsiloxanes are poly- and / or oligo-dimethylsiloxanes.
  • the non-polar or slightly non-polar solvent is a constitutional isomer of hexane.
  • the solvents can also be selected from: acyclic and cyclic hydrocarbons (pentane, hexane, heptane, cyclohexane), aromatic hydrocarbons (xylenes, toluene, benzene), halogenated compounds (chloroform, trichlorethylene) and ethers (diethyl ether, dimethoxyethane, tetrahydrofuran), where these solvents tend to be non-polar or only to be weak / slightly non-polar or polar.
  • Hexane is a preferred solvent because it has a lower evaporation rate compared to, for example, pentane.
  • the non-polar or slightly non-polar solvent is n-hexane.
  • the antifouling yarn according to the invention comprises a core running along the running direction and a corona surrounding it.
  • the corona contains poly- and oligo-siloxanes [SiR 2 0] n and tetrapodal zinc oxide (t-ZnO).
  • Tetrapodal zinc oxide is from Xin Jin et al. “Joining the Un-Joinable: Adhesion Between Low Surface Energy Polymers Using Tetrapodal ZnO Linkers”, Adv. Mat. 24, 42, pp. 5676-5680, 2012 and DE 102014 110 505 A1.
  • the mass fraction of the tetrapodal zinc oxide (t-ZnO) in the corona is in particular between 0.1 and 10%, preferably between 0.2 and 7.5%, particularly preferably between 0.3 and 5%.
  • the fibers consist of organic polymers, preferably of polyethylene, polyesters and / or polyamides. It is advantageous to use fibers that are commercially available as yarns and nets for maritime use (e.g. KREMMIN NETS & ROPES Mechanische Netzfabrik Walter Kremmin GmbH & Co KG.). With such commercially available nets and yarns, it is common practice to bundle the fibers into filaments. For protective nets that are used in aquaculture, because of their higher quality, knotted nets made of filaments (usually three) that are twisted together are used.
  • the matrix consists essentially of poly- and oligo-siloxanes [SiR 2 0] n. And can also contain tetrapodal zinc oxide (t-ZnO) or fragments of tetrapodal zinc oxide.
  • t-ZnO tetrapodal zinc oxide
  • the yarn itself is not changed, but rather penetrated and coated with the antifouling or fouling-release polymer, thus creating a toxin-free / biocide-free fouling-release or antifouling yarn.
  • the antifouling yarn according to the invention can be used as a yarn for an aquaculture net. Of course, other uses under water are possible and useful.
  • the invention is illustrated below with reference to the accompanying figures in FIG.
  • FIG. 1 Schematic representation of the cross section through an antifouling yarn according to the invention
  • Fig. 2 SEM images of an antifouling yarn according to the invention (cross section and top view);
  • Fig. 4 SEM image and X-ray dispersion analysis (EDX) of the cross section of an antifouling yarn according to the invention
  • Fig.5 SEM image and X-ray dispersion analysis (EDX) (element mapping of Si, C and Zn) of the cross-section of an antifouling yarn according to the invention and a smaller section of the image and
  • EDX X-ray dispersion analysis
  • Fig.6 Net made of yarn according to the invention and conventional yarn, after 21 weeks in natural water.
  • FIG. 1 shows a schematic representation of a cross section through an antifouling yarn according to the invention. It shows the corona (2) surrounding the core (1) made of fiber (4) and matrix (5). The tetrapodal zinc oxide particles (t-ZnO) (3) as part of the corona are shown.
  • t-ZnO tetrapodal zinc oxide particles
  • Fig. 2 shows the scanning electron microscope images of a yarn according to the invention. The recordings were made with a Zeiss Ultra Plus scanning electron microscope.
  • ® shows the corona, ⁇ the core, in ⁇ the top view of the corona can be seen.
  • the roughness (Ra) of the corona results in a value between 0.5 pm and 2 pm, preferably between 0.7 pm and 1.8 pm, particularly preferably between 1 pm and 1.5 pm.
  • the surface roughness of an untreated filament is between 8 pm and 10 pm.
  • Fig. 4 shows an SEM image and the X-ray dispersion analysis (EDX) with the aid of which the determined distribution of the elements in a material cross-section of the antifouling yarn according to the invention is shown.
  • the recordings were made with the EDX unit of the Zeiss Ultra Plus scanning electron microscope.
  • Fig. 5 shows a section of the picture.
  • Si silicon
  • C carbon
  • Zn zinc
  • Figure 6 shows a net made of conventional yarn (7) and yarn (6) according to the invention after being taken from a natural body of water.
  • the nets had previously been in natural water for 21 weeks. It shows biological growth which can be removed very easily from the yarn (6) according to the invention (fouling release).
  • the nets did not have to be cleaned because the growth was detached by the shear forces in the water or by the weight of the organisms.
  • the manufacturing method according to the invention for the yarn according to the invention comprises the following steps: i. Providing a solution of a poly- and / or oligo-dialkylsiloxane, a silane crosslinker and tetrapodal zinc oxide (t-ZnO) in a non-polar or slightly non-polar solvent as solution A; ii. Dipping conventional yarn in solution A; iii. Mechanical fulling of the yarn in solution A; iv. Allowing solution A to rest with the kneaded yarn; v. Removing the impregnated yarn from solution A; vi. Drying of the impregnated yarn.
  • the poly- and / or oligo-dialkylsiloxanes are preferably poly- and / or oligo-dimethylsiloxanes.
  • silane crosslinker is known to the person skilled in the art, for example from Ullmann's Encyclopedia of Industrial Chemistry, 5th edition, Volume A 24, p. 72.
  • silane crosslinker denotes silanes which have functional groups (X) capable of entering into a crosslinking reaction, for example acetate or amine.
  • the silane crosslinkers preferably have the general formula (R n SiX 4-n ), where R is selected from the group H, methyl, ethyl, propyl and X acetate (OCOCH3) and / or amine (NHR) is particularly preferred is triacetoxymethylsilane CH3S1 ( OOCCH3) 3. It is also possible to use mixtures of different silane crosslinkers.
  • Non-polar or slightly non-polar solvents are known to the person skilled in the art. They can be selected from the group of alkanes, alkenes, alkynes, aromatics, carboxylic acid esters,
  • the non-polar aprotic solvent is preferably selected from the group of the alkanes; it is particularly preferably a constitutional isomer of hexane, very particularly preferably n-hexane.
  • fillers or further auxiliaries can also be added to the solution in step i.
  • Such fillers and auxiliaries are generally known, for example additives from the group consisting of silicone plasticizers, adhesives, additives such as dyes, emulsifiers, stabilizers and catalysts.
  • Process steps i to v are preferably carried out at room temperature.
  • Drying vi can take place in air at temperatures between room temperature and approx. 80 ° C. If the product is dried at an elevated temperature, it should be stored for 5-10 minutes at room temperature in order to allow the solvent to evaporate initially.
  • n-hexane and Elastosil E43 are mixed together in a mass ratio of 1: 1 and a mass fraction of 1% t-ZnO is quickly added.
  • the mesh is completely immersed in the solution and should remain there for 1 to 5 minutes.
  • the solution is then mechanically drummed through with the mesh.
  • the meshed mesh then remains in the solution for 1 minute.

Landscapes

  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Agronomy & Crop Science (AREA)
  • Environmental Sciences (AREA)
  • Mechanical Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Inorganic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

L'invention se rapporte à un fil antisalissure comprenant une âme (1) s'étendant le long de la direction de déplacement et une couronne (2) entourant ladite âme, la couronne contenant des polysiloxanes et des oligosiloxanes [SiR2O]n et de l'oxyde de zinc tétrapodal (t-ZnO) (3) et l'âme (1) étant composée de fibres (4) et d'une matrice (5) et les fibres étant construites à partir de polymères organiques et la matrice contenant également des polysiloxanes et des oligosiloxanes [SiR2O]n. L'invention se rapporte également à un procédé de production de fil antisalissure et à une utilisation du fil antisalissure.
EP21726318.5A 2020-05-11 2021-05-05 Fil antisalissure et procédé de production de fil antisalissure et utilisation Pending EP4149260A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102020112729.4A DE102020112729A1 (de) 2020-05-11 2020-05-11 Antifouling-Garn und Antifouling-Garn-Herstellungsverfahren sowie Verwendung
PCT/DE2021/100408 WO2021228322A1 (fr) 2020-05-11 2021-05-05 Fil antisalissure et procédé de production de fil antisalissure et utilisation

Publications (1)

Publication Number Publication Date
EP4149260A1 true EP4149260A1 (fr) 2023-03-22

Family

ID=75977550

Family Applications (1)

Application Number Title Priority Date Filing Date
EP21726318.5A Pending EP4149260A1 (fr) 2020-05-11 2021-05-05 Fil antisalissure et procédé de production de fil antisalissure et utilisation

Country Status (3)

Country Link
EP (1) EP4149260A1 (fr)
DE (1) DE102020112729A1 (fr)
WO (1) WO2021228322A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024062020A1 (fr) 2022-09-22 2024-03-28 Universität Zu Lübeck Matériau structuré biocompatible et ses utilisations

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002161427A (ja) * 2000-11-22 2002-06-04 Unitica Fibers Ltd 水中資材用繊維
CN110091562A (zh) * 2019-05-07 2019-08-06 江南大学 一种基于剪切增稠胶的抗冲击柔性防护复合材料及其制备方法

Family Cites Families (5)

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Publication number Priority date Publication date Assignee Title
US20030077444A1 (en) 2001-05-10 2003-04-24 The Procter & Gamble Company Multicomponent fibers comprising starch and polymers
JP4952952B2 (ja) 2008-09-12 2012-06-13 信越化学工業株式会社 室温硬化性オルガノポリシロキサン組成物の製造方法
ES2856685T3 (es) 2012-11-13 2021-09-28 Chugoku Marine Paints Composición de recubrimiento antiincrustante, película de recubrimiento antiincrustante, sustrato antiincrustante y método para mejorar la estabilidad en almacenamiento de la composición de recubrimiento antiincrustante
US9024268B2 (en) 2013-03-15 2015-05-05 Bruker Axs, Inc. One-dimensional x-ray detector with curved readout strips
DE102014110505A1 (de) 2014-07-25 2016-01-28 Christian-Albrechts-Universität Zu Kiel Verfahren zur Herstellung von Mehrkomponentenwerkstücken mittels 3D-Druck

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002161427A (ja) * 2000-11-22 2002-06-04 Unitica Fibers Ltd 水中資材用繊維
CN110091562A (zh) * 2019-05-07 2019-08-06 江南大学 一种基于剪切增稠胶的抗冲击柔性防护复合材料及其制备方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
.: "Silane Coupling Agents", 1 January 2017 (2017-01-01), Japan, pages 1 - 28, XP93186360, Retrieved from the Internet <URL:https://www.shinetsusilicones.com/files/literature/NewSilane_E2017.pdf> *
See also references of WO2021228322A1 *

Also Published As

Publication number Publication date
WO2021228322A1 (fr) 2021-11-18
DE102020112729A1 (de) 2021-11-11

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