WO2016014290A1 - One-component structural adhesive containing isocyanate-terminated prepolymer - Google Patents

One-component structural adhesive containing isocyanate-terminated prepolymer Download PDF

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Publication number
WO2016014290A1
WO2016014290A1 PCT/US2015/040361 US2015040361W WO2016014290A1 WO 2016014290 A1 WO2016014290 A1 WO 2016014290A1 US 2015040361 W US2015040361 W US 2015040361W WO 2016014290 A1 WO2016014290 A1 WO 2016014290A1
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WO
WIPO (PCT)
Prior art keywords
structural adhesive
isocyanate
component structural
terminated prepolymer
adhesive
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.)
Ceased
Application number
PCT/US2015/040361
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English (en)
French (fr)
Inventor
Andreas Lutz
Daniel Schneider
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Dow Global Technologies LLC
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Dow Global Technologies LLC
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 Dow Global Technologies LLC filed Critical Dow Global Technologies LLC
Priority to US15/314,148 priority Critical patent/US10155891B2/en
Priority to JP2017503526A priority patent/JP6846335B2/ja
Priority to CN201580039174.1A priority patent/CN106536586A/zh
Priority to KR1020177003458A priority patent/KR102363246B1/ko
Priority to BR112017000946-3A priority patent/BR112017000946B1/pt
Priority to EP15742483.9A priority patent/EP3172254B1/en
Publication of WO2016014290A1 publication Critical patent/WO2016014290A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C65/00—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor
    • B29C65/48—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor using adhesives, i.e. using supplementary joining material; solvent bonding
    • B29C65/4805—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor using adhesives, i.e. using supplementary joining material; solvent bonding characterised by the type of adhesives
    • B29C65/483—Reactive adhesives, e.g. chemically curing adhesives
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C65/00—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor
    • B29C65/48—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor using adhesives, i.e. using supplementary joining material; solvent bonding
    • B29C65/4865—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor using adhesives, i.e. using supplementary joining material; solvent bonding containing additives
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C65/00—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor
    • B29C65/48—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor using adhesives, i.e. using supplementary joining material; solvent bonding
    • B29C65/52—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor using adhesives, i.e. using supplementary joining material; solvent bonding characterised by the way of applying the adhesive
    • B29C65/54—Joining or sealing of preformed parts, e.g. welding of plastics materials; Apparatus therefor using adhesives, i.e. using supplementary joining material; solvent bonding characterised by the way of applying the adhesive between pre-assembled parts
    • 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
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
    • 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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/302—Water
    • C08G18/307—Atmospheric humidity
    • 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
    • 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
    • C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
    • 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
    • C08G18/65—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
    • C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
    • 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/04—Non-macromolecular additives inorganic
    • 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
    • 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
    • C08G2170/00—Compositions for adhesives
    • C08G2170/40—Compositions for pressure-sensitive adhesives

Definitions

  • This invention relates generally to a one-component high modulus structural adhesive comprising an isocyanate-terminated prepolymer.
  • One-component urethane adhesives based on prepolymers of polytetramethylene ether glycol are known.
  • PTMEG polytetramethylene ether glycol
  • U.S. Pat. No. 5,288,797 discloses a one- component urethane system comprising a prepolymer based on PTMEG in which the isocyanate component is an aromatic isocyanate.
  • this reference does not disclose the adhesive described in the current invention.
  • the present invention is directed to a one-component structural adhesive comprising an isocyanate-terminated prepolymer comprising polymerized residues of: (a) 40 to 95 wt of a polytetramethylene ether glycol; and (b) 5 to 60 wt of an aliphatic diisocyanate.
  • the present invention is further directed to a method for bonding coated or painted parts made of fiber-reinforced plastics by applying a one-component structural adhesive comprising an isocyanate-terminated prepolymer comprising polymerized residues of: (a) 40 to 95 wt of a polytetramethylene ether glycol; and (b) 5 to 60 wt of an aliphatic diisocyanate to said parts.
  • a one-component structural adhesive comprising an isocyanate-terminated prepolymer comprising polymerized residues of: (a) 40 to 95 wt of a polytetramethylene ether glycol; and (b) 5 to 60 wt of an aliphatic diisocyanate to said parts.
  • Aliphatic diisocyanates useful in this invention include, e.g., hexamethylene diisocyanate ("HDI”), methylene dicyclohexyl diisocyanate or (hydrogenated MDI, "HMDI”) and isophorone diisocyanate (“IPDI”).
  • HDI hexamethylene diisocyanate
  • HMDI methylene dicyclohexyl diisocyanate
  • IPDI isophorone diisocyanate
  • Polytetramethylene ether glycol (PTMEG, also known as PTHF) is commonly prepared from polymerization of tetrahydrofuran and has the structure HO ⁇ (CH 2 )40 ⁇ n H, where n can vary from about 3 to about 45, corresponding to number-average molecular weights (Mn) from about 250 to about 3000.
  • Mn for the PTMEG is from 500 to 3000, preferably from 800 to 2600, preferably from 1100 to 2500, preferably from 1500 to 2200.
  • the isocyanate-terminated prepolymer comprises polymerized residues of: at least 50 wt% PTMEG, preferably at least 55 wt , preferably at least 60 wt , preferably at least 70 wt , preferably at least 75 wt , preferably at least 80wt ; preferably no more than 90 wt , preferably no more than 86 wt , preferably no more than 82 wt , preferably no more than 78 wt .
  • the prepolymer may also contain small amounts of polyols having from three to six hydroxyl groups, preferably C3-C10 triols (preferably C3-C8 triols) or tetra-ols, e.g., trimethylolpropane, pentaerythritol.
  • polymerized units of polyols having from three to six hydroxy groups are present in an amount from 0 to 5 wt , preferably from 0.1 to 3 wt , preferably from 0.2 to 1.5 wt .
  • the prepolymer contains polymerized units of one or more additional polyols, preferably polycaprolactone polyols, preferably in a total amount from 0 to 40 wt , preferably at least 5 wt , preferably at least 8 wt , preferably at least 11 wt ; preferably no more than 35 wt , preferably no more than 30 wt , preferably no more than 25 wt , preferably no more than 22 wt , preferably no more than 19 wt .
  • additional polyols preferably polycaprolactone polyols
  • the weight of isocyanate groups in the isocyanate-terminated prepolymer is from 1 to 6 wt , preferably from 1.5 to 5 wt , preferably from 2 to 4 wt .
  • Mn for the polycaprolactones is from 400 to 3000, preferably from 500 to 2000, preferably from 600 to 1500, preferably from 600 to 1000.
  • the isocyanate-terminated prepolymer comprises polymerized residues of: at least 8 wt aliphatic diisocyanate, preferably at least 10 wt , preferably at least 12 wt , preferably at least 14 wt , preferably at least 18 wt ; preferably no more than 40 wt , preferably no more than 50 wt , preferably no more than 45 wt , preferably no more than 30 wt , preferably no more than 25 wt .
  • the isocyanate-terminated prepolymer may be prepared using a mole ratio of isocyanate groups to hydroxyl groups which may vary as desired, preferably within a molar ratio of NCO/OH groups of 2.5:1 to 1.2: 1, preferably from 2.4:1 to 1.3: 1, preferably from 2.3:1 to 1.4:1, preferably from 2.3: 1 to 1.5: 1.
  • suitable catalysts are used to aid in formation of the prepolymer, preferably tin or zirconium catalysts, preferably Zr(IV) catalysts, e.g., zirconium acetylacetonate.
  • the amount of catalyst in the prepolymer is from 0.005 to 0.15 wt , preferably 0.01 to 0.1 wt , preferably 0.02 to 0.08 wt .
  • the one-component structural adhesive comprises the isocyanate-terminated prepolymer along with other typical adhesive ingredients, e.g., fillers (e.g., carbon black, kaolin, fumed silica) and catalysts (e.g., bismuth, tin or amine catalysts).
  • Bismuth catalysts are especially preferred, preferably Bi(III) salts, preferably carboxylate salts.
  • the total amount of catalyst(s) preferably is from 0.01 to 4 wt , preferably from 0.02 to 3 wt , preferably from 0.05 to 1 wt ; weights based on total weight of the adhesive.
  • the urea and urethane content of the adhesive is from 3 to 40 wt ; preferably at least 3.2 wt , preferably at least 3.4 wt , preferably at least 3.6 wt , preferably at least 3.8 wt ; preferably no more than 30 wt , preferably no more than 20 wt , preferably no more than 10 wt , preferably no more than 6 wt .
  • carbon black is present in an amount from 5 to 60 wt , preferably at least 7 wt , preferably at least 9 wt ;
  • kaolin is present in an amount from 5 to 60 wt , preferably at least 7 wt , preferably at least 9 wt ; preferably no more than 50 wt , preferably no more than 40 wt .
  • the isocyanate-terminated prepolymer is present in the adhesive in an amount from 20 to 100 wt ; preferably at least 30 wt , preferably at least 35 wt , preferably at least 40 wt ; preferably at least 45 wt ; preferably no more than 90 wt , preferably no more than 85 wt , preferably no more than 82 wt .
  • the present invention is directed to a method for bonding coated or painted parts made of fiber-reinforced plastics. These parts bonded to each other or to a dissimilar material, e.g., e-coated steel frames or e-coated metal roofs.
  • Preferred fiber-reinforced plastics are epoxy composite materials or thermoplastics, e.g., SMC.
  • the substrates may be similar material or dissimilar material.
  • the preferred thickness of the adhesive layer is from 1 to 5 mm, preferably from 2 to 4 mm.
  • the compositions of the present invention can be applied to desired substrates using conventional application techniques such as application from automated dispensing equipment and drum pumps.
  • Comparative formulations A, B and C are using aromatic MDI as diisocyanate compound. All of them are using a PPO polyether-polyol. Formulation A is using a PPO triol, B and C PPO diols with different molecular weights and C additionally A PPO triol.
  • ⁇ Formulation D is similar to A but uses an aliphatic diisocyanate, HDI, instead of an aromatic (MDI)
  • Formulation E uses a PPO polyether-polyol together with a crystalline polyester and an aliphatic diisocyanate (HDI)
  • Inventive formulation F is similar to E but uses a PTHF (PTMEG) polyether-diol instead of PPO and no polyester
  • Inventive formulation G uses PTHF, polyester and aromatic diisocyanate instead of aliphatic
  • Table 4 shows the formulation details of the formulated adhesives. Because of the low basic viscosity of the prepolymer, the adhesive formulations which use the prepolymers D, E and F need no plasticizer. Table 4: Adhesive formulation details
  • Table 5 presents the test data for the prepolymer itself.
  • the prepolymers which use HDI over MDI show a significant reduction in viscosity as compared to the other formulations and therefore can be used without adding plasticizer, either to the prepolymer or the adhesive formulation.
  • Table 6 shows the test data for the prepared adhesive formulations. The following can be concluded:
  • inventive formulations meet an elastic modulus of above 20 MPa
  • inventive formulations combine high elastic modulus with high bulk elongation of above 200%
  • the highest elastic moduli above 30 MPa are achieved by using aliphatic- (e.g. HDI) over aromatic (e.g. MDI) diisocyanates
  • Table 7 presents the limits for the bulk adhesive data and the prepolymer composition.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Adhesives Or Adhesive Processes (AREA)
PCT/US2015/040361 2014-07-25 2015-07-14 One-component structural adhesive containing isocyanate-terminated prepolymer Ceased WO2016014290A1 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US15/314,148 US10155891B2 (en) 2014-07-25 2015-07-14 One-component structural adhesive containing isocyanate-terminated prepolymer
JP2017503526A JP6846335B2 (ja) 2014-07-25 2015-07-14 イソシアナート末端プレポリマーを含有する一液型構造用接着剤
CN201580039174.1A CN106536586A (zh) 2014-07-25 2015-07-14 含有异氰酸酯封端预聚物的单组分结构粘合剂
KR1020177003458A KR102363246B1 (ko) 2014-07-25 2015-07-14 이소시아네이트-종료된 프레폴리머를 함유하는 1-성분 구조 접착제
BR112017000946-3A BR112017000946B1 (pt) 2014-07-25 2015-07-14 Adesivo estrutural de um componente e método para ligar partes revestidas ou pintadas feitas de plásticos reforçados com fibra
EP15742483.9A EP3172254B1 (en) 2014-07-25 2015-07-14 One-component structural adhesive containing isocyanate-terminated prepolymer

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201462028825P 2014-07-25 2014-07-25
US62/028,825 2014-07-25

Publications (1)

Publication Number Publication Date
WO2016014290A1 true WO2016014290A1 (en) 2016-01-28

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Country Status (7)

Country Link
US (1) US10155891B2 (enExample)
EP (1) EP3172254B1 (enExample)
JP (1) JP6846335B2 (enExample)
KR (1) KR102363246B1 (enExample)
CN (1) CN106536586A (enExample)
BR (1) BR112017000946B1 (enExample)
WO (1) WO2016014290A1 (enExample)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110055026A (zh) * 2019-04-25 2019-07-26 王鹏 一种灌缝材料及其制备方法
US20260109804A1 (en) * 2024-10-21 2026-04-23 Rogers Corporation Process for making polyurethane

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EP3172254A1 (en) 2017-05-31
US10155891B2 (en) 2018-12-18
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KR20170039186A (ko) 2017-04-10
KR102363246B1 (ko) 2022-02-16

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