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US-12624146-B2 - Polyurethane composition

US12624146B2US 12624146 B2US12624146 B2US 12624146B2US-12624146-B2

Abstract

Embodiments relate to a coating, adhesive, sealant, elastomer, or reaction injection molded material forming polyurethane composition that comprises an isocyanate component that includes at least one isocyanate-terminated prepolymer, and an isocyanate reactive component that includes at least one Lewis acid catalyst polymerized polyether polyol having a weight average molecular weight from 200 g/mol to 1,000 g/mol, an average primary hydroxyl group content of at least 30%, and an average acetal content of at least 0.05 wt %.

Inventors

  • Masayuki Suzuki
  • Arjun Raghuraman
  • John W. Weston
  • An Kaga
  • Richard J. Keaton
  • Adrian J. Birch
  • Maria Jose Cotanda Santapau

Assignees

  • DOW GLOBAL TECHNOLOGIES LLC
  • DOW SILICONES CORPORATION

Dates

Publication Date
20260512
Application Date
20211019

Claims (10)

  1. 1 . A coating, adhesive, sealant, elastomer, or reaction injection molded material forming polyurethane composition, the composition comprising: an isocyanate component that includes at least one isocyanate-terminated prepolymer, and an isocyanate reactive component that includes at least one Lewis acid catalyst polymerized polyether polyol having a weight average molecular weight from 200 g/mol to 1,000 g/mol, an average primary hydroxyl group content of at least 30% based on total number of hydroxyl groups, and an average acetal content of at least 0.05 wt % based on total weight of the Lewis acid catalyst polymerized polyol, a Lewis acid catalyst for forming the Lewis acid catalyst polymerized polyether polyol having a general formula M(R 1 ) 1 (R 2 ) 1 (R 3 ) 1 (R 4 ) 1 , whereas M is boron, aluminum, indium, bismuth or erbium, R 1 , R 2 , R 3 , and R 4 are each independent, R 1 includes a first fluoro/chloro or fluoroalkyl-substituted phenyl group, R 2 includes a second fluoro/chloro or fluoroalkyl-substituted phenyl group, R 3 includes a third fluoro/chloro or fluoroalkyl-substituted phenyl group or a first functional group or functional polymer group, R 4 is a second functional group or functional polymer group.
  2. 2 . The composition as claimed in claim 1 , wherein the isocyanate-terminated prepolymer is the reaction product of a polyisocyanate and a DMC catalyst polymerized polyether polyol having a weight average molecular weight from 300 g/mol to 3,500 g/mol.
  3. 3 . The composition as claimed in claim 1 , wherein the composition includes from 56 wt to 86 wt % of the isocyanate component and 14 wt % to 44 wt % of the isocyanate-reactive component.
  4. 4 . The composition as claimed in claim 1 , wherein the Lewis acid catalyst polymerized polyol is present in an amount of at least 50 wt % based on a total weight of the isocyanate-reactive component.
  5. 5 . The composition as claimed in claim 1 , wherein R 3 includes the third fluoro/chloro or fluoroalkyl-substituted phenyl group.
  6. 6 . The composition as claimed in claim 1 , wherein the first fluoro/chloro or fluoroalkyl-substituted phenyl group and the second fluoro/chloro or fluoroalkyl-substituted phenyl group are the same.
  7. 7 . The composition as claimed in claim 1 , wherein R 3 includes the third fluoro/chloro or fluoroalkyl-substituted phenyl group and the first fluoro/chloro or fluoroalkyl-substituted phenyl group and the second fluoro/chloro or fluoroalkyl-substituted phenyl group are the same.
  8. 8 . The composition as claimed in claim 1 , wherein R 3 includes the third fluoro/chloro or fluoroalkyl-substituted phenyl group and the first fluoro/chloro or fluoroalkyl-substituted phenyl group, the second fluoro/chloro or fluoroalkyl-substituted phenyl group, and the third fluoro/chloro or fluoroalkyl-substituted phenyl group are the same.
  9. 9 . A coating, adhesive, sealant, elastomer, or reaction injection molded material formed with the composition as claimed in claim 1 , a polyether alcohol being a non-finished alcohol.
  10. 10 . A method of making a coating, adhesive, sealant, elastomer, or reaction injection molded material, the method comprising providing the composition as claimed in claim 1 .

Description

FIELD Embodiments relate to a two component polyurethane composition for use in coatings, adhesives, sealants, elastomers, and materials formed from reaction injection molding (RIM), which composition includes at least one prepolymer and a Lewis acid catalyst polymerized polyol, and/or polyurethane products prepared using the polyurethane composition. INTRODUCTION Polyurethane products such as coatings, adhesives, sealants, elastomers, and materials formed from reaction injection molding (RIM) may be produced by reacting an isocyanate component with an isocyanate-reactive component. The isocyanate component may include at least one prepolymer, e.g. an isocyanate-terminated prepolymer. The isocyanate-reactive component may include at least one polyether polyol that is produced by reacting an initiator with an alkylene oxide in the presence of a catalyst, which can also be referred to as epoxide alcoholysis. The initiator has one or more functional groups the alkylene oxide can react with to begin forming polymer chains and may establish the number of hydroxyl groups that the resultant polyether polyol will have. The use of a Lewis acid polymerization catalyst for such polymerization to form a Lewis acid catalyst polymerized polyether polyol has been proposed for use to, e.g., improve appearance of the polyurethane product, while still allowing for a fast cure time. SUMMARY Embodiments may be realized by providing a coating, adhesive, sealant, elastomer, or reaction injection molded material forming polyurethane composition, the composition comprising an isocyanate component that includes at least one isocyanate-terminated prepolymer and an isocyanate reactive component that includes at least one Lewis acid catalyst polymerized polyether polyol having a weight average molecular weight from 200 g/mol to 1,000 g/mol, an average primary hydroxyl group content of at least 30% based on total number of hydroxyl groups, and an average acetal content of at least 0.05 wt % based on total weight of the Lewis acid catalyst polymerized polyol. A Lewis acid catalyst for forming the Lewis acid catalyst polymerized polyether polyol has a general formula M(R1)1(R2)1(R3)1(R4)0 or 1, whereas M is boron, aluminum, indium, bismuth or erbium, R1, R2, R3, and R4 are each independent, R1 includes a first fluoro/chloro or fluoroalkyl-substituted phenyl group, R2 includes a second fluoro/chloro or fluoroalkyl-substituted phenyl group, R3 includes a third fluoro/chloro or fluoroalkyl-substituted phenyl group or a first functional group or functional polymer group, optional R4 is a second functional group or functional polymer group. BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 illustrates the resultant films for Working Examples 1 to 3 and Comparative Example A. DETAILED DESCRIPTION Embodiments relate to a two component polyurethane composition for use in coatings, adhesives, sealants, elastomers, and materials formed from reaction injection molding (RIM), in which the composition with a specific type of Lewis acid catalyzed polyol results in a polyurethane based product with a lower amount of bubbles, e.g., in comparison to when such polyurethane based product is prepared with a composition that includes a general polyol prepared with DMC catalyst technology. The polyurethane composition includes an isocyanate component that includes at least one prepolymer and an isocyanate reactive component that includes at least the Lewis acid catalysis polymerized polyether polyol. The isocyanate component includes at least one isocyanate-terminated prepolymer and may optionally include one or more polyisocyanates (such as those known for use in the art). For the example, the isocyanate component includes at least 50 wt % (at least 60 wt %, at least 70 wt %, at least 80 wt %, at least 90 wt %, at least 95 wt %, at least 98 wt %, etc.) of one or more isocyanate-terminated prepolymer, based on a total weight of the isocyanate component. The isocyanate reactive component includes at least the Lewis acid catalyst polymerized polyether polyol, e.g., a least 50 wt %, 60 wt %, 70 wt %, 80 wt %, and/or 90 wt %, based on a total weight of the isocyanate-reactive component. The isocyanate component and/or the isocyanate-reactive component may include one or more additives known in the art for use in polyurethane compositions for use in coatings, adhesives, sealants, elastomers, and materials formed from reaction injection molding. The isocyanate index may be from 60 to 300 (e.g., 80 to 250, 80 to 200, 80 to 150, 90 to 140, 90 to 120, etc.). Isocyanate index refers to the stoichiometric ratio of isocyanate groups to isocyanate-reactive groups provided to the reaction mixture, multiplied by 100. To form the polyurethane based coatings, adhesives, sealants, elastomers, and materials formed from reaction injection molding (RIM), the isocyanate and isocyanate-reactive components will be mixed and applied to the substrate just before use. Before the components reac