WO2025224005A1 - Polyurée hybride à durcissement lent - Google Patents

Polyurée hybride à durcissement lent

Info

Publication number
WO2025224005A1
WO2025224005A1 PCT/EP2025/060709 EP2025060709W WO2025224005A1 WO 2025224005 A1 WO2025224005 A1 WO 2025224005A1 EP 2025060709 W EP2025060709 W EP 2025060709W WO 2025224005 A1 WO2025224005 A1 WO 2025224005A1
Authority
WO
WIPO (PCT)
Prior art keywords
polyurea
mdi
diamine
prepolymer
polymer
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
PCT/EP2025/060709
Other languages
English (en)
Inventor
Kamlesh Panwar
Roopali Rai
Shreedhar BHAT
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.)
Huntsman International LLC
Original Assignee
Huntsman International 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 Huntsman International LLC filed Critical Huntsman International LLC
Publication of WO2025224005A1 publication Critical patent/WO2025224005A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C08G18/28—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
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3225—Polyamines
    • C08G18/3237—Polyamines aromatic
    • C08G18/3243—Polyamines aromatic containing two or more aromatic rings
    • 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
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
    • C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino 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
    • C08G18/65—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
    • C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
    • C08G18/6685—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3225 or polyamines of C08G18/38
    • 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
    • C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes

Definitions

  • Polyurea is a type of elastomer that is derived from the reaction product of an isocyanate component and an amine component. Polyurea is often used as a waterproofing material in industrial and commercial settings to protect surfaces from water damage. It is applied as a liquid coating, which then quickly cures to form a durable, waterproof barrier. This can be used for waterproofing roofs, foundations, decks, and other surfaces. It can also be used to seal concrete structures, such as swimming pools, water tanks and retaining walls. Polyurea is known for its excellent resistance to water, chemicals, abrasion, and impact, which makes it an ideal option for waterproofing surfaces that are exposed to harsh conditions.
  • Polyurea polymers often show fast curing and have a low or short pot life. Their applications are therefore often limited to application with spray-machines. There is therefore a need to develop a slow cure polyurea that can be applied by hand and has a long pot life.
  • US2016229947A1 describes the synthesis of polyurea prepolymer or quasi-prepolymer by reacting isocyanate component (4,4' MDI or uretonimine-modified 4,4' MDI or hexamethylene diisocyanate (HDI) allophanate or HDI trimer or aliphatic HDI biuret) with secondary diamine.
  • US4686242A demonstrates the preparation of polyurea prepolymer or quasi-prepolymer by reacting amine functional compound (with at least 400 equivalent weight) with an excess of polyisocyanate and developing a polyurea or polyurea-polyurethane prepolymer by reacting isocyanate reactive material with polyurea prepolymer.
  • EP0529839A1 reports the synthesis of quasi-prepolymer by reacting a polyoxyalkylene polyamine with aliphatic polyisocyanate and developing a polyurea elastomer using the quasi- prepolymer, polyoxyalkylene polyamine and aromatic diamine.
  • the prepolymers and the resin systems described in all these documents have shown only marginal improvements in the pot life (less than 30 minutes). They are therefore still mostly unsuitable for hand application.
  • the term “about” is used to indicate that a value includes the inherent variation of error for the quantifying device, mechanism, or method, or the inherent variation that exists among the subject(s) to be measured.
  • the designated value to which it refers may vary by plus or minus ten percent, or plus or minus nine percent, or plus or minus eight percent, or plus or minus seven percent, or plus or minus six percent, or plus or minus five percent, or plus or minus four percent, or plus or minus three percent, or plus or minus two percent, or plus or minus one percent, or one or more fractions therebetween.
  • phrases “or combinations thereof’ and “and combinations thereof’ as used herein refers to all permutations and combinations of the listed items preceding the term.
  • “A, B, C, or combinations thereof’ is intended to include at least one of A, B, C, AB, AC, BC, or ABC and, if order is important in a particular context, also BA, CA, CB, CBA, BCA, ACB, BAC, or CAB.
  • expressly included are combinations that contain repeats of one or more items or terms such as BB, AAA, CC, AABB, AACC, ABCCCC, CBBAAA, CABBB, and so forth.
  • a polyurea prepolymer prepared from a reaction mixture comprising: a) Methylene diphenyl diisocyanate (MDI) comprising a mixture of 2,4’ MDI and 4,4’ MDI; and b) At least one component selected from a secondary diamine chain extender and a secondary polymeric diamine.
  • MDI Methylene diphenyl diisocyanate
  • Hybrid Polyurea is a type of elastomer that is derived from the reaction product of an isocyanate prepolymer component, such as that described in the first aspect, and a resin component comprising at least one polyol and optionally at least one polyamine through step- growth polymerization.
  • the isocyanate containing prepolymer is also referred to herein as a quasi-prepolymer.
  • Methylene diphenyl diisocyanate is an aromatic diisocyanate. MDI is found in three commonly appearing isomers. These vary by the positions of the isocyanate groups around the rings: 2,2'-MDI, 2,4'-MDI, and 4,4'-MDI as shown below:
  • the 4,4' isomer is the most widely used isomer - this isomer is also commonly known as “pure MDI”.
  • the use of an MDI comprising 2,4’ MDI and at least one component selected from a secondary diamine chain extender and a secondary polymeric diamine provides a better control over the reaction exotherm during the synthesis of the polyurea prepolymer.
  • This polyurea prepolymer has a lower reactivity than commonly used prepolymers.
  • the lower reactivity of polyurea prepolymer and polyol increases the curing time and therefore improves the pot life of the hybrid polyurea system.
  • aromatic is intended to take its usual meaning. That is, it is an organic compound containing a planar unsaturated ring of atoms which is stabilized by an interaction of the bonds forming the ring, e.g., benzene and its derivatives.
  • Chain extenders typically align themselves with the stiff and largely immobile hard segments in polyurethane elastomers. The interaction between the soft and hard segments in a polyurethane elastomer impacts the physical properties such as elasticity, tensile strength, tear resistance, and elongation. Examples of chain extenders include low molecular weight (short chain) secondary diamines, low molecular weight diols and combinations thereof.
  • the produced prepolymer can be reacted with the resin component to form a polyureapolyurethane polymer which has a pot life in excess of forty minutes. Such a hybrid polyurea polymer can therefore be used for hand applications as well as in spray applications, if desired.
  • the MDI comprises between about 0.1 wt% to about 50 wt% of 2,4’ MDI and between about 50 wt% to about 99 wt% 4,4’ MDI. In some embodiments, the MDI may additionally comprise 2,2’ MDI. In some embodiments, the MDI comprises between about 0 to about 8 wt% 2,2’ MDI.
  • the polyurea prepolymer comprises between about 20 wt% and about 90 wt% MDI based on the total weight of the reaction mixture.
  • Polyurea is a block polymer comprising both hard and soft blocks.
  • the soft blocks deliver flexibility, and the hard blocks deliver heat resistance.
  • This block structure offers a good performance balance of flexibility, heat resistance, elastic recovery, abrasion resistance, and processability.
  • the chain extender is selected from the group consisting of secondary aliphatic amine, secondary aromatic amine, and sterically hindered diamines and mixtures thereof.
  • secondary aliphatic amines include, but are not limited to, secondary aliphatic amine selected from the group consisting of N, N'-dialkylethylenediamine; N, N'-dialkyl- 1,2-diaminopropane; N, N'-dialkyl- 1,3 -diaminopropane; 4,4'-methylenebis(N- alkylcyclohexamine); l,4-di(alkylamino)cyclohexane; l-methyl-2,4-di(alkylamino)-3,5- dialkylcyclohexanes; N, N'-dialkyl isophoronediamine; l,3-di(l'methyl-l'- alkylaminoethyl)benzene; l,6
  • the secondary polymeric diamine when present, is selected from the group consisting of a secondary aliphatic amine, a secondary aromatic amine, and mixtures thereof. Any suitable secondary polymeric diamine may be used. The skilled person would understand which secondary polymeric diamines could be used.
  • the secondary polymeric diamine may comprise a secondary aliphatic amine selected from the group consisting of N,N'-Diisopropyl-polypropylene glycol diamine, or the secondary polymeric diamine may comprise a secondary aromatic amine.
  • the reaction mixture comprises: a) between about 25 wt% and about 90 wt% of MDI; b) between about 0 wt% and about 20 wt% secondary diamine chain extender; and c) between about 0 and about 75 wt% secondary polymeric diamine based on the total weight of the reaction mixture provided that the reaction mixture comprises at least one of component b) or c).
  • a polyurea-polyurethane hybrid polymer prepared by reacting the prepolymer described above and a resin blend comprising at least one polyol and optionally a polyamine or a low molecular weight diamine or a mixture thereof.
  • the produced polymer has a long pot life which is in excess of 40 min whilst maintaining good polymer properties.
  • the polyol used in the resin blend is a polyester polyol, a polyether polyol, a polycarbonate polyol, or a mixture thereof.
  • Suitable polyols include but are not limited to poly ether polyols such as polyoxyethylene polyol (polyethylene glycol), a polyoxypropylene polyol (polypropylene glycol), a polytetrahydrofuran diol, a poly caprolactone diol and combinations thereof such as a polyethylene polypropylene polyol.
  • polyester polyol examples include, but are not limited to, polyester polyols having terminal hydroxyl groups which may include those obtained by the reaction between dicarboxylic acids such as succinic acid, glutaric acid, adipic acid, azelaic acid, sebacic acid, dodecanoic acid, phthalic anhydride, isophthalic acid, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, maleic anhydride, fumaric acid, itaconic acid and a polyhydroxy compound selected from the short chain polyols.
  • dicarboxylic acids such as succinic acid, glutaric acid, adipic acid, azelaic acid, sebacic acid, dodecanoic acid, phthalic anhydride, isophthalic acid, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, maleic anhydride, fumaric acid, itaconic acid and a polyhydroxy compound selected from the short chain
  • Polyester polyols can be also obtained by the reaction between a lactone compound such as P-propiolactone, pivalolactone, 5-valerolactone, P-methyl-5-valerolactone, s-caprolactone. methyl-s-caprolactone, dimethyl-s-caprolactone, trimethyl-s-caprolactone and a polyhydroxy compound selected from the short chain polyols and combinations thereof.
  • a lactone compound such as P-propiolactone, pivalolactone, 5-valerolactone, P-methyl-5-valerolactone, s-caprolactone.
  • the polyamine is a polymeric secondary diamine, a secondary amine chain extender, or a mixture thereof. Suitable examples of secondary diamines and secondary amine chain extenders are described above.
  • the resin blend further comprises at least one component selected from one or more defoamers, one or more moisture scavengers, castor oil, one or more pigments, and one or more plasticizers.
  • a defoamer or an anti-foaming agent is a chemical additive that reduces and hinders the formation of foam.
  • anti-foam agent and defoamer are often used interchangeably. Any type of defoamer can be included in the resin mixture. Commonly used agents are insoluble oils, polydimethylsiloxanes and other silicones, certain alcohols, stearates, and glycols.
  • Polymeric materials and their corresponding additives and fillers may have excessive moisture levels that can adversely affect the physical characteristics of the resulting finished composite.
  • a moisture scavenger therefore removes moisture from the composition. Any suitable moisture scavenger may be used. Commonly used examples include molecular sieves, natural clay, calcium oxide, calcium chloride, and modified starch.
  • Plasticizers increase the flow and thermoplasticity of a polymer by decreasing the viscosity of the polyol blend.
  • Commonly used polymer plasticizers include citrates, benzoates, ortho-phosphates, terephthalates, adipates, azelates, sebacates, and trimellitates.
  • a mixture of the prepolymer and the resin blend has a pot life greater than 40 min at 25 °C and between 30-95% relative humidity.
  • the pot life at 25 °C and between 30-95% relative humidity is between 1 hour and 1. 5 hours. As the relative humidity increases, the quality of any resulting coating may be affected.
  • a method for preparing a polyurea-polyurethane hybrid comprising mixing a polyurea prepolymer as described above and a resin composition as described above and curing.
  • Curing can be performed at any suitable temperature and pressure, preferably at room temperature and pressure.
  • the resultant polymer preferably has a pot life greater than 40 min, has a touch dry time less than or equal to 5 hours, a tack free time of less than or equal to 24 hours.
  • Pot life is also known as the working time or useable life. Pot life is often thought of as the length of time that a mixed system retains a viscosity low enough to be applied to a surface at a specified temperature. In this case pot life, touch dry time and tack free time are measured at 25 °C. Touch dry time is the point at which a polymer surface is sufficiently dry such that it no longer flows nor sticks to a finger that touches it lightly. The polymer is not completely dry at this point. The tack-free time is the duration to which the polymer surface is no longer sticky and does not create a fingerprint when touched with a gloved finger. It can be seen to have dry properties. Tackiness is the state where the dry-to-touch polymer still feels sticky and has poor blocking resistance.
  • the resultant polymer preferably has a hardness (Shore D) of greater than or equal to 40.
  • the Shore D hardness scale ranges from 1 to 100. Harder materials have higher Shore D values than softer materials. It can be measured by any method known to the skilled person; for example, using a Shore durometer.
  • the resultant polymer preferably has a tensile strength at break greater than or equal to 5 MPa.
  • Tensile tests measure the force required to break a plastic sample specimen and the extent to which the specimen stretches or elongates to that breaking point.
  • the polymer tensile strength is measured by any method known to the skilled person. For example, ASTM D412 is performed by applying a tensile force to a sample specimen and measuring various properties of the specimen under stress. It is conducted on a universal testing machine (also called a tensile testing machine) at tensile rates ranging from 1 to 500 mm/min until the specimen fails (yields or breaks).
  • the resultant polymer preferably has an elongation at break of greater than or equal to 200%.
  • Elongation at break also known as fracture strain, is the ratio between changed length and initial length after breakage of the test specimen. It expresses the capability of polymer to resist changes of shape without crack formation. It can be measured by any method known to the skilled person.
  • the resultant polymer preferably has an adhesion strength of greater than or equal to 1.5 N/mm 2 .
  • Polymer adhesion strength can be measured using any method known to the skilled person. For example, ASTM D7234 is used to pull off the polymer coatings from the coated substrate.
  • the resultant polymer preferably shows a weight loss of less than 150 mg when the abrasion strength is measured using Taber method with Hl 8 wheels as abrader and under a load of 1 kg, evaluated for 1000 cycles.
  • the resultant cured polymer preferably has zero water permeability measured by the Karsten tube method.
  • a hybrid polyurea produced by the method described above.
  • the hybrid polyurea produced by the method described above is applied to a surface using hand application or by spray application.
  • the polymer is applied using hand application.
  • a polyurea prepolymer was synthesised using MI-50 (Suprasec 3051) (without chain extender) and polyurea-polyurethane hybrid coating.
  • Apolyol blend was prepared using 81.6 g Gpol 115, 6.47 g of Siliporite SA 1720, 6.47 g of castor oil and 1.95 g of BYK 066N.
  • the required amount of above synthesized polyurea prepolymer was added to the polyol blend to obtain an index of 133 and coated on a teflon sheet or metal panels or concrete blocks.
  • the equation for calculating the index is shown below:
  • Apolyol blend was prepared using 81.6 g Gpol 115, 6.47 g of Siliporite SA 1720, 6.47 g of castor oil and 1.95 g of BYK 066N. The required amount of above synthesized polyurea prepolymer was added to the polyol blend to obtain an index of 133 and coated on a teflon sheet or metal panels or concrete blocks.
  • Apolyol blend was prepared using 81.6 g Gpol 115, 6.47 g of Siliporite SA 1720, 6.47 g of castor oil and 1.95 g of BYK 066N. The required amount of above synthesized polyurea prepolymer was added to the polyol blend to obtain an index of 133 and coated on a Teflon sheet or metal panels or concrete blocks.
  • NCO value of the prepolymer, viscosity of the prepolymer and resin blend, and pot life time, touch dry time, tack free time, hardness, tensile strength and elongation for the hybrid polyurea coatings are shown below in Table 1.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

La présente invention concerne un prépolymère de polyurée préparé à partir d'un mélange réactionnel comprenant du 2, 4' et 4,4'méthylène diphényl diisocyanate ; et au moins un composant choisi parmi un allongeur de chaîne diamine secondaire et une diamine polymère secondaire. L'invention concerne également un procédé de production d'un polymère hybride de polyurée-polyuréthane et un polymère hybride de polyurée-polyuréthane.
PCT/EP2025/060709 2024-04-25 2025-04-17 Polyurée hybride à durcissement lent Pending WO2025224005A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IN202411032797 2024-04-25
IN202411032797 2024-04-25
EP24181173.6 2024-06-10
EP24181173 2024-06-10

Publications (1)

Publication Number Publication Date
WO2025224005A1 true WO2025224005A1 (fr) 2025-10-30

Family

ID=95480672

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2025/060709 Pending WO2025224005A1 (fr) 2024-04-25 2025-04-17 Polyurée hybride à durcissement lent

Country Status (1)

Country Link
WO (1) WO2025224005A1 (fr)

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4686242A (en) 1985-03-25 1987-08-11 The Dow Chemical Company Polyurea polymers prepared from urea containing prepolymers
EP0529839A1 (fr) 1991-08-26 1993-03-03 Texaco Chemical Company Elastomères de polyurée durcissant lentement
US20020103326A1 (en) * 1997-03-11 2002-08-01 Huntsman Petrochemical Corporation Method of preparing spray elastomer systems
US20020107354A1 (en) 2001-02-02 2002-08-08 Smith Stuart B. Aliphatic polyurea prepolymers, compositions and methods
WO2002102869A1 (fr) * 2001-06-15 2002-12-27 Huntsman Petrochemical Corporation Extendeurs de chaine aminee synergique dans des elastomeres en spray a base de polyuree
US20110137005A1 (en) * 2005-03-28 2011-06-09 Albemarle Corporation Chain Extenders
US20160229947A1 (en) 2015-02-09 2016-08-11 Super Skin Systems, Inc. Polyurea prepolymers
US20160264709A1 (en) * 2015-03-12 2016-09-15 Super Skin Systems, Inc. Polyurea prepolymers made from primary and secondary diamines

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4686242A (en) 1985-03-25 1987-08-11 The Dow Chemical Company Polyurea polymers prepared from urea containing prepolymers
EP0529839A1 (fr) 1991-08-26 1993-03-03 Texaco Chemical Company Elastomères de polyurée durcissant lentement
US20020103326A1 (en) * 1997-03-11 2002-08-01 Huntsman Petrochemical Corporation Method of preparing spray elastomer systems
US20020107354A1 (en) 2001-02-02 2002-08-08 Smith Stuart B. Aliphatic polyurea prepolymers, compositions and methods
WO2002102869A1 (fr) * 2001-06-15 2002-12-27 Huntsman Petrochemical Corporation Extendeurs de chaine aminee synergique dans des elastomeres en spray a base de polyuree
US20110137005A1 (en) * 2005-03-28 2011-06-09 Albemarle Corporation Chain Extenders
US20160229947A1 (en) 2015-02-09 2016-08-11 Super Skin Systems, Inc. Polyurea prepolymers
US20160264709A1 (en) * 2015-03-12 2016-09-15 Super Skin Systems, Inc. Polyurea prepolymers made from primary and secondary diamines

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