WO2023174777A1 - Adhésif de polyuréthane destiné à être utilisé dans un panneau sandwich pour radôme 5g - Google Patents

Adhésif de polyuréthane destiné à être utilisé dans un panneau sandwich pour radôme 5g Download PDF

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Publication number
WO2023174777A1
WO2023174777A1 PCT/EP2023/055927 EP2023055927W WO2023174777A1 WO 2023174777 A1 WO2023174777 A1 WO 2023174777A1 EP 2023055927 W EP2023055927 W EP 2023055927W WO 2023174777 A1 WO2023174777 A1 WO 2023174777A1
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WO
WIPO (PCT)
Prior art keywords
sandwich panel
polyurethane adhesive
polyetherpolyol
radome
adhesive according
Prior art date
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PCT/EP2023/055927
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English (en)
Inventor
Na LIU
Tao Feng
Jian Xin Zhang
Bin Fan
Ping Li
Original Assignee
Basf Se
Basf (China) Company Limited
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 Basf Se, Basf (China) Company Limited filed Critical Basf Se
Publication of WO2023174777A1 publication Critical patent/WO2023174777A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4829—Polyethers containing at least three hydroxy groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/02—Layered products essentially comprising sheet glass, or glass, slag, or like fibres in the form of fibres or filaments
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/12—Layered products comprising a layer of synthetic resin next to a fibrous or filamentary layer
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/32—Layered products comprising a layer of synthetic resin comprising polyolefins
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/36—Layered products comprising a layer of synthetic resin comprising polyesters
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/36—Layered products comprising a layer of synthetic resin comprising polyesters
    • B32B27/365—Layered products comprising a layer of synthetic resin comprising polyesters comprising polycarbonates
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
    • B32B5/02—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by structural features of a fibrous or filamentary layer
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
    • B32B5/18—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by features of a layer of foamed material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
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    • B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
    • B32B5/22—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed
    • B32B5/24—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed one layer being a fibrous or filamentary layer
    • B32B5/245—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by the presence of two or more layers which are next to each other and are fibrous, filamentary, formed of particles or foamed one layer being a fibrous or filamentary layer another layer next to it being a foam layer
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/04—Interconnection of layers
    • B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3206—Polyhydroxy compounds aliphatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4825—Polyethers containing two hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4833—Polyethers containing oxyethylene units
    • C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • C08G18/6677—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203 having at least three hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/08—Polyurethanes from polyethers
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01Q—ANTENNAS, i.e. RADIO AERIALS
    • H01Q1/00—Details of, or arrangements associated with, antennas
    • H01Q1/42—Housings not intimately mechanically associated with radiating elements, e.g. radome
    • H01Q1/422—Housings not intimately mechanically associated with radiating elements, e.g. radome comprising two or more layers of dielectric material
    • B—PERFORMING OPERATIONS; TRANSPORTING
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    • C—CHEMISTRY; METALLURGY
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Definitions

  • the present invention belongs to the technical field of polyurethane adhesives.
  • the present invention relates to a polyurethane adhesive for the preparation of a sandwich panel used in 5G radome, to a sandwich panel for 5G radome produced therefrom, and to a method for preparing said sandwich panel for 5G radome.
  • 5G communication technology has developed rapidly.
  • the wave usually has a wavelength of millimeter wave band. Because of the short wavelength of such millimeter wave, the signal transmission is greatly influenced by the material type and structure of a sandwich panel used in the 5G radome. Therefore, a higher requirement is put forward on the material and structure of the sandwich panel used in 5G radome.
  • CN 111421937A describes a laminated material for 5G millimeter wave radome, which includes a skin layer and a core layer, wherein the skin layer is made by a thermoplastic resin material and there is an optional adhesive film present between the skin layer and the core layer.
  • CN 108091998A describes a V-shaped radome which is obtained by co-curing an antenna, a skin layer and a filling core layer, wherein the skin layer and the filling core layer are bonded together with a cyanate ester adhesive film.
  • CN104577324A discloses a method for designing a radome suitable for high-power broad band radar, which, among others, includes the selection of the materials for each layer of C-sandwich structure used in the radome wall.
  • polyurethane adhesive has significant influence on the dielectric constant (Dk) and the dissipation factor (Df) of the sandwich panel. Therefore, there is a need to provide an adhesive which has a sufficiently low Df combined with a low Dk while maintaining other favorable characteristics, such as light weight. In addition, there is a need to provide a sandwich panel used in 5G radome with low transmission loss in combination with good mechanical properties.
  • the first objective of the present invention is to provide a polyurethane adhesive which has a low dissipation factor (Df) of ⁇ 0.085, a low dielectric constant (Dk) of ⁇ 3.2, and a low density of ⁇ 1 .2 g/cm 3 , for use in the production of a sandwich panel used in 5G radome.
  • Df dissipation factor
  • Dk dielectric constant
  • the polyurethane adhesive of the present invention provides an optimum balance between the transmission properties such as the Dk and Df values and the density property.
  • the presently claimed invention is directed to a polyurethane adhesive which is prepared by reacting:
  • (F) additives and/or auxiliaries wherein the at least one polyetherpolyol comprise oxypropylene groups in an amount of at least 50 wt%, based on the total weight of the polyetherpolyol.
  • the presently claimed invention relates to the use of the polyurethane adhesive of the present invention for the preparation of a sandwich panel used in 5G radome.
  • Another aspect of the present invention relates to a sandwich panel for 5G radome, wherein the polyurethane adhesive of the present invention is present in-between at least two adjacent layers of the sandwich panel and forms an adhesive film between them, and wherein the sandwich panel has a transmission of at least 89%, measured according to the ENCHI test method at a frequency of 6 GHz.
  • the articles “a” and “an” refer to one or more than one (i.e. , at least one) of the grammatical object of the article.
  • an element means one element or more than one element.
  • the temperature refers to room temperature and the pressure refers to ambient pressure. Unless otherwise identified, all percentages (%) are “percent by weight”. All values for molecular weight are based on weight average molecular weight, unless indicated otherwise.
  • the polyurethane adhesive according to the claimed invention has a low Dk and Df values.
  • the Dk and Df values have great impact on the transmission properties of the resulting sandwich panel.
  • This low Dk and Df values allows a sandwich panel with several layers for use in 5G radome to be bonded together by applying the polyurethane adhesive of the claimed invention to each layer.
  • the polyurethane adhesive according to the present invention typically have a Dk value of ⁇ 3.2, preferably ⁇ 3.1 , more preferably 3.0, the Dk value being determined by 2.45GHz split post dielectric resonator according to I EC 61189-2-721.
  • the polyurethane adhesive according to the present invention typically have a Df value of ⁇ 0.085, preferably ⁇ 0.081 , more preferably ⁇ 0.06, and even more preferably ⁇ 0.05, the Df value being determined by 2.45GHz split post dielectric resonator according to I EC 61189-2-721.
  • the polyurethane adhesive of the invention offers light weight which are added advantages.
  • the polyurethane adhesive according to the claimed invention has a density of ⁇ 1.2 g/cm 3 , preferably ⁇ 1.15 g/cm 3 , more preferably ⁇ 1.12 g/cm 3 , measured according to ASTM D1875-03(2018).
  • the polyurethane adhesive is prepared by reacting:
  • (F) additives and/or auxiliaries wherein the at least one polyetherpolyol comprise oxypropylene groups in an amount of at least 50 wt%, based on the total weight of the polyetherpolyol.
  • the di- and/or polyisocyanate component (A) is an isocyanate functional component which forms urethane linkages when reacted with the hydroxyl groups of the polyol component (B).
  • Suitable di- and/or polyisocyanates are known to those skilled in the art and include unmodified isocyanates, modified isocyanates, and isocyanate prepolymers.
  • the term “polyisocyanates” refer to those comprising three or more isocyanate functional groups.
  • Such organic di- and/or polyisocyanates may include linear or branched, aliphatic, cycloaliphatic, araliphatic, aromatic, and heterocyclic polyisocyanates of the type described, for example, by W. Siefken in Justus Liebigs Annalen der Chemie, 562, pages 75 to 136. Examples of such di- and/or polyisocyanates include those represented by the formula,
  • di- and/or polyisocyanates include, but are not limited to, ethylene diisocyanate; 1 ,4-tetramethylene diisocyanate; 1 ,6-hexamethylene diisocyanate; 1 ,12-dodecane diisocyanate; cyclobutane-1 ,3-diisocyanate; cyclohexane- 1 ,3- and -1 ,4-diisocyanate, and mixtures of these isomers; 1-isocyanato-3,3,5-trimethyl-5- isocyanatomethylcyclohexane (isophorone diisocyanate); 2,4- and 2,6-hexahydrotoluene diisocyanate and mixtures of these isomers; dicyclohexylmethane-4,4'-diisocyanate (hydrogenated MDI, or HMDI); 1 ,3- and 1 ,4- phenylene diisocyanate; 2,4
  • Isocyanate-terminated prepolymers may also be employed in the present invention.
  • the isocyanate-terminated prepolymers may be a polymerization product of respective isocyanates themselves, i.e. , dimers, trimers or oligomers, or a reaction product of the isocyanate component and the active hydrogen-containing component to give an isocyanate functionalized prepolymer.
  • Such active hydrogen-containing components have functional groups like hydroxyl groups, ester groups or amine groups.
  • the prepolymers may be prepared by reacting an excess of organic polyisocyanate or mixtures thereof with a minor amount of an active hydrogen-containing compound as determined by the well-known Zerewitinoff test, as described by Kohler in "Journal of the American Chemical Society," 49, 3181 (1927). These compounds and their methods of preparation are well known to those skilled in the art.
  • the use of any one specific active hydrogen-containing compound is not critical; any such compound can be employed in the practice of the present invention.
  • the di- and/or polyisocyanate is selected from the group consisting of one or more isomers or homologues of diphenylmethane diisocyanate, polymeric diphenylmethane diisocyanate, and diphenylmethane diisocyanate based prepolymers.
  • the di- and/or polyisocyanate component preferably contains organic di- and/or polyisocyanates having a number average isocyanate (NCO) functionality of from at least 1.8 to 4.0, more preferably from 2.0 to 3.0, most preferably from 2.3 to 2.9.
  • the NCO functionality of the isocyanate component may be a number ranging between any combination of these values, inclusive of the recited values.
  • the isocyanate component preferably has a free isocyanate group content (NCO content) in the range of from 5% to 50% by weight, more preferably from 12% to 40%, most preferably from 20% to 35% by weight.
  • the free NCO group content of the polyisocyanate component may be an amount ranging between any combination of these values, inclusive of the recited values.
  • the polyols according to the claimed invention comprises at least one polyetherpolyol which comprise oxypropylene groups in an amount of at least 50 wt%, based on the total weight of the polyetherpolyol.
  • the at least one polyetherpolyol comprises oxypropylene groups in an amount of at least 70 wt%, preferably at least 80 wt%, and more preferably at least 95 wt%, based on the total weight of the polyetherpolyol.
  • the polyetherpolyol may comprise oxyethylene groups in an amount of up to 30 wt%, preferably up to 20 wt%, and more preferably up to 10 wt%, based on the total weight of the polyetherpolyol. It is predicted that polyetherpolyol comprising oxypropylene groups in an amount of less than 50 wt% may not give a polyurethane adhesive with desired properties.
  • the at least one polyetherpolyol employed in the practice of the present invention will generally have an average OH number of from 100 to 650 mg KOH/g, preferably, from 300 to 600 mg KOH/g, most preferably, from 350 to 500 mg KOH/g and an average functionality of from 1.0 to 4.5, preferably, from 1.5 to 4.0, most preferably, from 2.5 to 3.2.
  • the at least one polyetherpolyol has an average molecular weight Mw in the range from 90 to 5000 g/mol, preferably from 150 to 3000 g/mol, more preferably 300 to 1000 g/mol.
  • This at least one polyetherpolyol may constitute at least 70% by weight of the components (B)- (F) of the present invention, but will generally be included in the components (B)-(F) in an amount of up to 95 wt%, preferably, in an amount of from 80 wt% to 90 wt%.
  • the polyols contain at least one polyetherpolyol according to the invention.
  • the polyetherpolyol can be produced by known processes, for example by anionic polymerization using alkali metal hydroxides or alkali metal alcoholates as catalysts, and with addition of at least one starter molecule which comprises from 2 to 3 reactive hydrogen atoms, or by cationic polymerization using Lewis acids, such as antimony pentachloride or boron fluoride etherate, from one or more alkylene oxides having from 2 to 4 carbon atoms in the alkylene moiety.
  • Lewis acids such as antimony pentachloride or boron fluoride etherate
  • alkylene oxides examples include tetrahydrofuran, propylene 1 ,3-oxide, butylene 1 ,2- or 2,3-oxide, and preferably ethylene oxide and propylene 1 ,2-oxide.
  • Other catalysts that can be used are multimetal cyanide compounds, known as DMC catalysts.
  • the alkylene oxides can be used alone, in alternating succession, or in the form of a mixture. Preference is given to use of mixtures of propylene 1 ,2-oxide and ethylene oxide, where amounts of up to 20 wt%, based on the total amount of alkylene oxides, of the ethylene oxide are used, and amounts of at least 50 wt% of the propylene oxide are used.
  • a starter molecule that can be used is water or di- or trihydric alcohols, such as ethylene glycol, 1 ,2- or 1 ,3-propanediol, diethylene glycol, dipropylene glycol, 1 ,4-butanediol, glycerol, or tri methylolpropane.
  • molecules having primary and secondary amine functionalities can be used as starter material.
  • Other suitable polyols are polymer-modified polyetherols, particularly preferably graft polyetherols. Such polymer modified polyetherpolyols are also known as polymer polyetherols.
  • polymer polyetherols are described by way of example in WO 05/098763 and EP-A-250 351 , and are usually produced via free-radical polymerization of suitable olefinic monomers, such as styrene, acrylonitrile, (meth)acrylates, (meth)acrylic acid, and/or acrylamide, in a polyetherol serving as graft base.
  • suitable olefinic monomers such as styrene, acrylonitrile, (meth)acrylates, (meth)acrylic acid, and/or acrylamide
  • the side chains are generally produced via transfer of the free radicals from growing polymer chains onto polyetherols.
  • the polymer polyetherol comprises, alongside the graft copolymers, mainly the homopolymers of the olefins, dispersed in unaltered polyetherol.
  • the monomers used comprise acrylonitrile, or styrene, preferably acrylonitrile and styrene.
  • the monomers are optionally polymerized in the presence of further monomers, of a macromer, i.e., of an unsaturated polyol capable of free-radical polymerization, and of a moderator, and with use of a free-radical initiator, mostly azo compounds or peroxide compounds, in a polyetherol as continuous phase. This process is described by way of example in DE 111 394, US 3 304 273, US 3 383 351 , US 3 523 093, DE 1 152 536, and DE 1 152 537.
  • the macromers are concomitantly incorporated into the copolymer chain.
  • the proportion of the macromers is usually from 1 to 20% by weight, based on the total weight of the monomers used to produce the polymer polyol.
  • Chain extenders and/or crosslinking agents (e) can be used individually or preferably in the form of a mixture.
  • Chain extenders and/or crosslinking agents (C) used comprise substances with a molar weight that is preferably smaller than 500 g/mol, particularly preferably from 60 to 400 g/mol, more preferably from 60 to 250 g/mol, where chain extenders have 2 hydrogen atoms reactive toward isocyanates and crosslinking agents have 3 hydrogen atoms reactive toward isocyanate.
  • chain-extenders/crosslinkers are liquids at 25° C.
  • aliphatic-OH functional compounds such as those just listed, are the most preferred chain- extenders/crosslinkers, it is also within the scope of the present invention to employ certain polyamines, polyamine derivatives, and/or polyphenols.
  • suitable amines known in the art include diisopropanolamine, diethanolamine, and 3,5-diethyl-2,4-diaminotoluene, 3, 5- diethyl-2,6-diaminotoluene, and mixtures thereof.
  • Suitable isocyanate reactive amine derivatives include certain imino-functional compounds such as those described in EP 0284 253 and EP 0 359 456 and certain enamino-functional compounds such as those described in EP 0 359 456 having two or more isocyanate-reactive groups per molecule.
  • Reactive amines, especially aliphatic primary amines, are less preferred due to their extremely high reactivity with polyisocyanates, but may optionally be used, if desired, in minor amounts.
  • Blowing agents (D) can also be present during the production of polyurethane adhesive. Blowing agents (D) that can be used comprise well-known compounds having chemical and/or physical effect or mixtures of these blowing agents. Chemical blowing agents are compounds which use reaction with isocyanate to form gaseous products, an example being water or formic acid. Physical blowing agents are compounds which have been emulsified or dissolved in the starting materials for polyurethane production and which vaporize under the conditions of polyurethane formation.
  • hydrocarbons such as perfluorohexane, chlorofluorocarbons, and ethers, esters, ketones, acetals, and mixtures thereof, for example cycloaliphatic hydrocarbons having from 4 to 8 carbon atoms, or fluorocarbons.
  • a preferred embodiment uses, as blowing agent, a mixture comprising at least one of said blowing agents and water, and in particular water as sole blowing agent.
  • the blowing agents may comprise expandable microspheres which are in the form of hollow polymer microspheres filled with blowing agent, such as gas or low-boiling liquids, preferably hydrocarbons.
  • blowing agent such as gas or low-boiling liquids, preferably hydrocarbons.
  • Expandable microspheres are hollow micro-beads, which comprise a thermoplastic polymer shell (such as polyacrylonitrile or copolymers thereof) encapsulating hydrocarbon gas.
  • a thermoplastic polymer shell such as polyacrylonitrile or copolymers thereof
  • the thermoplastic shell encapsulating hydrocarbon gas softens.
  • the hydrocarbon gas expands and exerts an increasing pressure on the shell, resulting in an increase in the volume of the microspheres.
  • the heat to which the material is exposed is sufficient to cause the thermoplastic shell to soften and simultaneously cause the enclosed gas to expand.
  • the expandability of the microspheres may be indicated by TMA density [kg/m 3 ], determined by Mettler Toledo Stare thermal analysis system as a heating rate of 20°C/min.
  • the TMA density here is the minimum achievable density at atmospheric pressure before collapse of the microspheres.
  • Any thermally expandable microspheres can be used in the present invention.
  • hydrocarbon as used herein is intended to include non-halogenated and partially or fully halogenated hydrocarbons.
  • Examples of expandable microspheres suitable for use in this invention include, but are not limited to, EXPANCEL WU, EXPANCEL DU, EXPANCEL SL and EXPANCEL MB series, commercially available from AkzoNobel, and ADVANCELL EM, commercially available from Sekisui Chemical Company.
  • Other expandable microspheres that are commercially available or known to those skilled in the art are also suitable for use in this invention.
  • the blowing agents are used in an amount of from 3 to 10 % by weight, preferably from 4 to 6 % by weight, based on the total weight of components (B) to (F).
  • Catalysts for the polyurethane-forming reactions of organic polyisocyanates are well known to those skilled in the art. These catalysts are described by way of example in “Kunststoffhandbuch, Band 7, Polyurethane” [Plastics Handbook, volume 7, Polyurethanes] Carl Hanser Verlag, 3rd edition 1993, chapter 3.4.1. Catalyst(s), where used, is/are preferably introduced into the reaction mixture by pre-mixing with the polyol component. As catalysts (F), conventional catalysts as known in the field of production of polyurethanes can be applied.
  • amidines such as 2,3-dimethyl-3,4,5,6-tetrahydropyrimidine
  • tertiary amines such as triethylamine, tributylamine, dimethylbenzylamine, N-methyl-, N-ethyl-, and N-cyclohexylmor- pholine, N,N,N',N'-tetramethylethylenediamine, N,N,N',N'-tetramethylbutanediamine, N,N,N',N'- tetramethylhexanediamine, pentamethyldiethylenetriamine, tetramethyldiaminoethyl ether, bis(dimethylaminopropyl)urea, dimethylpiperazine, 1 ,2-dimethylimidazole, 1-azabicyclo[3.3.0]oc- tane, and preferably 1 ,4-diazabicyclo[2.2.2]octan
  • organometallic compounds preferably organotin compounds, such as tin(ll) salts of organic carboxylic acids, e.g. tin(ll) acetate, tin(ll) octoate, tin(ll) ethylhexoate, and tin(ll) laurate, and the dialkyltin(IV) salts of organic carboxylic acids, e.g.
  • the organometallic compounds can be used alone or preferably in combination with strongly basic amines. Mixtures of metal catalysts and of basic amine catalysts are optionally used as catalysts. Preferably exclusively amine catalysts are used.
  • the catalysts are applied in an amount of 0.01 to 2% by weight, preferably 0.1 to 1% by weight, each based on the total weight of components (B) to (F).
  • additives and/or auxiliaries may also be used.
  • the additive and/or auxiliary component is added to the polyol component (B).
  • a portion of the additive and/or auxiliary component is added to the polyol component before the reaction mixture is formed and another portion is separately added to the reaction mixture.
  • the additive and/or auxiliary component in its entirety is added to the polyol component before the reaction mixture is formed.
  • the additive and/or auxiliary component may include, but are not limited to, fillers, water scavengers, deaerating agents, surface-active substances, wetting agents, flame retardants, smoke suppressants, bonding agents, dyes, pigments, hydrolysis inhibitors, antistatic agents, antioxidants, UV stabilizers, minor amounts of viscosity reducing inert diluents, fungistatic and bacteriostatic substances, combinations of these, and also any other known additives from the art.
  • Preferred additives are fillers, water scavengers, deaerating agents, bonding agents, UV stabilizers, antioxidants and/or wetting agents.
  • the additive and/or auxiliary may be used to modify the properties of the adhesive, for example, to control the wetting behavior, viscosity, storage life, sagging, moisture resistance, etc.
  • the additives used herein are known and used in the polyurethane chemistry art for producing polyurethane adhesives.
  • a water scavenger is a material which is capable of adsorbing water.
  • Preferred water scavengers are zeolite and/or calcium oxide.
  • the wetting agents may be used to improve the spreadability of the adhesive on the components to be bonded.
  • the deaerating agents may be added to reduce the formation of bubbles or to reduce sagging while bonding the components.
  • Preferred fillers are selected from the group consisting of silica, titanium dioxide, sulphates, silicates, carbonates, kaolin, chalk, mica, quartz, talc, glass beads, ceramic spheres, and mixtures thereof.
  • the fillers can be used individually or as mixtures and are advantageously added to the reaction mixture in amounts of from 10 to 30 % by weight, preferably from 15 to 25 % by weight, more preferably from 15 to 20 % by weight, based on the total weight of components (B) to (F).
  • the components (A) to (F) are preferably mixed at temperatures of from 15 to 70°C and in particular from 20 to 50°C.
  • components (B) to (F) are premixed to form the polyol component, which is then mixed with the isocyanate component (A).
  • the stoichiometry of mixing polyurethane-forming formulations, containing an organic di- and/or polyisocyanate and a polyol component is often expressed by a quantity known in the art as the isocyanate index.
  • the index of such a formulation is simply the equivalence ratio of the NCO groups of di- and/or polyisocyanates (A) to the sum of the reactive hydrogen atoms of components (B) and optional component (C). This quantity is often multiplied by 100 and expressed as a percent.
  • Preferred isocyanate index values in the mixing activated formulations, which are suitable for use in the practice of the present invention range from 95 to 150. A more preferred range of the isocyanate index values is from 105 to 130.
  • a further object of the present invention is to provide the use of a polyurethane adhesive according to the invention for the preparation of a sandwich panel used in 5G radome.
  • the present invention provides a sandwich panel for 5G radome, comprising: 1) an inner skin layer,
  • the polyurethane adhesive according to the present invention is present in-between at least two adjacent layers of the sandwich panel and forms an adhesive bond between them, and wherein the sandwich panel has a transmission of at least 89%, measured according to the EN- CHI test method at a frequency of 6 GHz.
  • the sandwich panel according to the invention has a transmission of at least 92%, preferably at least 94%.
  • the inner and outer skin layer each has a thickness of from 0.2 to 1 mm, and each comprises a polycarbonate (PC), a polyethylene terephthalate (PET), a polybutylene terephthalate (PBT), a polypropylene (PP), or combinations thereof, preferably PC.
  • the sandwich panel comprises a third and fourth reinforcement layer. In a further embodiment, the sandwich panel comprises further reinforcement layers.
  • the first and second reinforcement layer each has a thickness of from 0.1 to 0.2 mm, and each comprises at least one reinforcing substance selected from the group consisting of glass fibers, glass mats, carbon fibers, polyester fibers, aramid fibers, nylon fibers, and basalt fibers.
  • the core layer has a thickness of from 2 to 3 mm, and comprises at least one foams selected from the group consisting of a polyurethane (Pll), a polypropylene (PP), a polyethylene terephthalate (PET), a polystyrene (PS), and a polyvinyl chloride (PVC), preferably Pll.
  • Pll polyurethane
  • PP polypropylene
  • PET polyethylene terephthalate
  • PS polystyrene
  • PVC polyvinyl chloride
  • the polyurethane adhesive according to the present invention is applied to form a bond film with a thickness of 0.05-0.3 mm, preferably 0.05-0.2 mm, more preferably 0.05- 0.1 mm.
  • the sandwich panel according to the invention has a density of ⁇ 0.9 g/cm 3 , preferably ⁇ 0.8 g/cm 3 , more preferably ⁇ 0.7 g/cm 3 , even more preferably ⁇ 0.65 g/cm 3 and still more preferably ⁇ 0.65 g/cm 3 , measured according to ASTM D1875-03(2018).
  • the sandwich panel according to the invention has a density of ⁇ 0.9 g/cm 3 , preferably ⁇ 0.8 g/cm 3 , more preferably ⁇ 0.7 g/cm 3 , even more preferably ⁇ 0.65 g/cm 3 and still more preferably ⁇ 0.65 g/cm 3 , measured according to ASTM D1875-03(2018).
  • the sandwich panel according to the invention has an impact strength of at least 10 KJ/m 2 , preferably at least 13 KJ/m 2 , more preferably at least 14 KJ/m 2 , even more preferably at least 15 KJ/m 2 , and still more preferably at least 18 KJ/m 2 , determined accordinging to IOZD Notched ASTM D256-2010E1.
  • the sandwich panel according to the invention has a flexural strength of at least 15 MPa, preferably at least 18 KJ/m 2 , more preferably at least 20 KJ/m 2 , determined accordinging to DIN EN ISO 178.
  • the sandwich panel according to the invention has a transmission of at least 89%, preferably at least 90%, more preferably at least 93%, and even more preferably at least 93.5%, measured according to the ENCHI test method at a frequency of 6 GHz.
  • the sandwich panel according to the invention has no break in the Ball-drop- ping test, which is carried out at a temperature of -40 °C , with a ball having a weight of 500 g and from a height of 1 meter. The test is performed at a corner of the panel product.
  • the present invention further provides a method for preparing a sandwich panel for 5G radome according to the present invention, comprising
  • Polyol 1 Glycerin-started polyoxypropylene polyol, with an OH value of 400 mg KOH/g, a hydroxyl functionality of 3, and a molecular weight Mw of 420 g/mol.
  • Polyol 2 Glycerin-started polyether polyol comprising propylene oxide unit (25.3 wt%) and ethylene oxide unit (72.5 wt%), with an OH value of 42 mg KOH/g, a hydroxyl functionality of 2.66, and a molecular weight Mw of 3550 g/mol.
  • Polyol 3 Propylene glycol-started polyoxypropylene polyol comprising propylene oxide unit (96.1 wt%) only, with an OH value of 55 mg KOH/g, a hydroxyl functionality of 1.93, and a molecular weight Mw of 190 g/mol.
  • Polyol 4 Propylene glycol-started polyoxypropylene polyol, with an OH value of 104 mg KOH/g, a hydroxyl functionality of 1.98, and a molecular weight Mw of 1070 g/mol.
  • Catalyst POLYCAT SA 8 from Evonik Specialty Chemicals (Shanghai) Co. Ltd.
  • Additive 1 addovate LP from BASF
  • Additive 3 Aerosil 200 from Evonik
  • Additive 4 Vetec from Sigma-Aldrich (Shanghai) Trading Co. Ltd.
  • Ball-dropping test under -40 °C, with a ball of 500 g and from a height of 1 meter
  • Density measured according to ASTM D1875-03(2018) standard test method for density of adhesives in fluid form
  • Each of the polyurethane adhesives includes B-component, which includes therein polyol components, crosslinker, catalyst, blowing agent and some additives, and A- component, which is isocyanate.
  • the B-component was prepared by mixing the respective materials as specified in table 1 by agitation and then making the mixture stand untill the agitating air bubbles were removed.
  • the thus-prepared B-component was then injected into the B tank of the polyurethane low-pressure machine, and the A-component was added into the A tank, with the temperatures of the B tank and the A tank being set as 20-30 °C, respectively.
  • the B-component and the A-component were mixed by speedmixer at 2000 rpm for about 1 min to give the product of the polyurethane adhesive.
  • the cured adhesive was cut for Dk and Df test. The results were summarized in the following table 1.
  • PO ratio means weight percentage of oxypropylene groups within the polyetherpolyol based on the total weight of the polyetherpolyol.
  • Inventive Examples 1-4 realized the desired compromised Dk and Df values and the density of ⁇ 1.12 g/cm 3 . Furthermore, the Dk and Df values for the adhesive in Exp. No. 4 combined with the glass fibre (GF) were ⁇ 4.17 and ⁇ 0.04, respectively. Production of the sandwich panel
  • Example 5 Pll foam+GF/Epoxy+PC
  • An epoxy adhesive was commercially available from Huntsman under the trade name of Araldite 2015.
  • a spread PC film with a thickness of 0.75 mm was used as an inner skin layer, on which was disposed a glass-fiber layer with a thickeness of 0.15 mm as a first reinforcement layer. Then, a Pll foam with a thicknes of 2.5 mm, as a core layer, was disposed on the glass-fiber layer by using the epoxy adhesive in a thickness of 0.1 mm. Another glass-fiber layer with a thickeness of 0.15 mm, as a second reinforcement layer, was disposed on the Pll foam, which was then covered by a PC film with a thickness of 0.75 mm as an outer skin layer, to give a sandwich board with a surface area of 1 m 2 . The thus-prepared sandwich board was baked under a temperature of 80-90 °C with 20 Kg of gravity applied for 2 hours to be fully cured, which was then cooled down at room temperature for properties tests. The final thickness was 3.6 mm.

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Abstract

La présente invention concerne un adhésif de polyuréthane préparé en faisant réagir (A) des di- et/ou poly- isocyanates avec (B) des polyols contenant au moins un polyétherpolyol, éventuellement en présence (C) d'allongeurs de chaîne et/ou d'agents de réticulation, (D) d'agents de soufflage, (E) de catalyseurs, et/ou (F) d'additifs et/ou d'auxiliaires, le ou les polyétherpolyols comprenant des groupes oxypropylène en une quantité d'au moins 50 % en poids, sur la base du poids total du polyétherpolyol. L'invention concerne en outre l'utilisation d'un adhésif de polyuréthane à des fins de préparation d'un panneau sandwich utilisé dans un radôme 5G, un panneau sandwich pour un radôme 5G, et un procédé de préparation d'un panneau sandwich pour un radôme 5G.
PCT/EP2023/055927 2022-03-15 2023-03-08 Adhésif de polyuréthane destiné à être utilisé dans un panneau sandwich pour radôme 5g WO2023174777A1 (fr)

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