GB1545061A - Curable poly(alkylene)ether polyol-based resins having improved properties - Google Patents

Curable poly(alkylene)ether polyol-based resins having improved properties

Info

Publication number
GB1545061A
GB1545061A GB9982/76A GB998276A GB1545061A GB 1545061 A GB1545061 A GB 1545061A GB 9982/76 A GB9982/76 A GB 9982/76A GB 998276 A GB998276 A GB 998276A GB 1545061 A GB1545061 A GB 1545061A
Authority
GB
United Kingdom
Prior art keywords
sealant
adhesive
aromatic
cycloaliphatic
initiator
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.)
Expired
Application number
GB9982/76A
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.)
Henkel Loctite Corp
Original Assignee
Henkel Loctite Corp
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 Henkel Loctite Corp filed Critical Henkel Loctite Corp
Publication of GB1545061A publication Critical patent/GB1545061A/en
Expired legal-status Critical Current

Links

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
    • C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C09J175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/067—Polyurethanes; Polyureas
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
    • C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
    • C08F299/06—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from 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
    • 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
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
    • C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
    • 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
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
    • 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
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
    • C08G18/8009—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203
    • C08G18/8012—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3203 with diols
    • 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
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8006—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32
    • C08G18/8038—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/32 with compounds of C08G18/3225
    • 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
    • C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • 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
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Sealing Material Composition (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Paints Or Removers (AREA)

Abstract

To prepare a curable adhesive/sealant, an organic polyisocyanate whose isocyanate groups are bonded to aromatic or cycloaliphatic carbon atoms is reacted first with a polyalkylene ether polyol and then with an acrylic or methacrylic ester which has a hydroxyl or non-tertiary amino group in the molecule. The polyisocyanate used is preferably the reaction product of an aromatic or cycloaliphatic polyisocyanate and an aromatic or cycloaliphatic polyol or polyamine. Solvents which are coreactive in the later curing can be present. The storage-stable prepolymers have rigid and flexible segments. To adhere surfaces or seal off gaps between surfaces, the adhesive/sealant is introduced between the surfaces together with a free-radical initiator and allowed to cure. Curing can be anaerobic or by means of UV-irradiation, depending on the choice of initiator. The initiator can be added to the adhesive/sealant or applied separately to a surface. The cured adhesive/sealant is highly flexible and has excellent tensile and impact strength. Gaps more than 1 mm wide can be sealed.
GB9982/76A 1975-03-12 1976-03-12 Curable poly(alkylene)ether polyol-based resins having improved properties Expired GB1545061A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US55774075A 1975-03-12 1975-03-12

Publications (1)

Publication Number Publication Date
GB1545061A true GB1545061A (en) 1979-05-02

Family

ID=24226697

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9982/76A Expired GB1545061A (en) 1975-03-12 1976-03-12 Curable poly(alkylene)ether polyol-based resins having improved properties

Country Status (11)

Country Link
JP (1) JPS51114436A (en)
AU (1) AU508482B2 (en)
BR (1) BR7601482A (en)
CA (1) CA1091384A (en)
CH (1) CH637685A5 (en)
DE (1) DE2610423C2 (en)
ES (1) ES446032A1 (en)
FR (1) FR2303835A1 (en)
GB (1) GB1545061A (en)
IT (1) IT1057983B (en)
NL (1) NL7602600A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2150938A (en) * 1983-12-05 1985-07-10 Tyndale Plains Hunter Limited Hydrophilic polyurethane acrylate compositions
GB2199040A (en) * 1986-12-06 1988-06-29 Smith & Nephew Ass Adhesives, their preparation and use
US4914173A (en) * 1986-12-06 1990-04-03 Smith And Nephew Associate Companies Plc Adhesives, their preparation and use
WO2000075253A1 (en) * 1999-06-07 2000-12-14 3M Innovative Properties Company Adhesive composition and optical disc using the same
FR2938267A1 (en) * 2008-11-07 2010-05-14 Bostik Sa Use of an adhesive composition made of polyurethane bicomponent in cryogenic application, preferably methane tanker carrying liquefied gases
WO2010052671A1 (en) * 2008-11-07 2010-05-14 Bostik Sa Use of a polyurethane adhesive composition for cryogenic applications

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4288479A (en) * 1973-09-24 1981-09-08 Design Cote Corp. Radiation curable release coatings
US4133723A (en) * 1978-01-03 1979-01-09 Lord Corporation Actinic radiation-curable formulations from the reaction product of organic isocyanate, poly(alkylene oxide) polyol and an unsaturated addition-polymerizable monomeric compound having a single isocyanate-reactive hydrogen group
US4425468A (en) * 1981-12-31 1984-01-10 Ppg Industries, Inc. Polyurea-polyurethane acrylate polymer dispersions
US4451627A (en) * 1982-09-07 1984-05-29 The Dow Chemical Company Addition polymerizable urethane-based anaerobic adhesives made from tin (II) organoesters
FR2579610B1 (en) * 1985-03-28 1987-08-21 Saint Gobain Vitrage ADHESIVE LAYER USED IN THE MANUFACTURE OF SHEET WINDOWS AND SHEET WINDOWS COMPRISING SUCH A LAYER
DE3544428A1 (en) * 1985-12-16 1987-06-19 Piestert Gerhard Agent which cures in the absence of oxygen for bonding surfaces
JPH0676578B2 (en) * 1986-12-27 1994-09-28 東亞合成化学工業株式会社 Anaerobic curable adhesive composition
JPS6420283A (en) * 1987-07-14 1989-01-24 Toa Gosei Chem Ind Adhesive composition
DE4025776A1 (en) * 1990-08-14 1992-02-20 Thera Ges Fuer Patente New curable prepolymers prepn. - from diol-or di:amino-terminated poly:tetra-hydro-furan with di:isocyanate and hydroxy-or amino-acrylate or with isocyanato-acrylate
US5128434A (en) * 1990-11-27 1992-07-07 Bausch & Lomb Incorporated Control of hard segment size in polyurethane formation
JP3196269B2 (en) * 1991-12-16 2001-08-06 ジェイエスアール株式会社 Liquid curable resin composition
FR3090641B1 (en) * 2018-12-19 2022-02-11 Bostik Sa (Meth)acrylic composition comprising a modified polyurethane

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3425988A (en) * 1965-01-27 1969-02-04 Loctite Corp Polyurethane polyacrylate sealant compositions
FR1495558A (en) * 1966-08-08 1967-09-22 Standard Products Co Polyurethane, its preparation process and its use in tacky coating compositions
GB1352063A (en) * 1971-01-08 1974-05-15 Ici Ltd Polymerisable compositions and resins derived thererom
US3873640A (en) * 1972-04-21 1975-03-25 Lord Corp Adhesive bonding of polyvinyl chloride and other synthetic resin substrates
IE39134B1 (en) * 1972-05-16 1978-08-16 Loctite Ltd Improvements in or relating to photo-initiated optical
DE2324832A1 (en) * 1973-05-17 1974-12-12 Langen & Co AXIAL PISTON PUMP

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2150938A (en) * 1983-12-05 1985-07-10 Tyndale Plains Hunter Limited Hydrophilic polyurethane acrylate compositions
GB2199040A (en) * 1986-12-06 1988-06-29 Smith & Nephew Ass Adhesives, their preparation and use
GB2199040B (en) * 1986-12-06 1990-01-24 Smith & Nephew Ass Adhesives, their preparation and use
US4914173A (en) * 1986-12-06 1990-04-03 Smith And Nephew Associate Companies Plc Adhesives, their preparation and use
WO2000075253A1 (en) * 1999-06-07 2000-12-14 3M Innovative Properties Company Adhesive composition and optical disc using the same
FR2938267A1 (en) * 2008-11-07 2010-05-14 Bostik Sa Use of an adhesive composition made of polyurethane bicomponent in cryogenic application, preferably methane tanker carrying liquefied gases
WO2010052671A1 (en) * 2008-11-07 2010-05-14 Bostik Sa Use of a polyurethane adhesive composition for cryogenic applications

Also Published As

Publication number Publication date
BR7601482A (en) 1976-09-14
DE2610423C2 (en) 1986-09-11
AU508482B2 (en) 1980-03-20
IT1057983B (en) 1982-03-30
NL7602600A (en) 1976-09-14
FR2303835B1 (en) 1981-10-09
ES446032A1 (en) 1977-06-01
JPS61365B2 (en) 1986-01-08
DE2610423A1 (en) 1976-09-16
CH637685A5 (en) 1983-08-15
CA1091384A (en) 1980-12-09
AU1182676A (en) 1977-09-15
JPS51114436A (en) 1976-10-08
FR2303835A1 (en) 1976-10-08

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Legal Events

Date Code Title Description
PS Patent sealed
PE20 Patent expired after termination of 20 years

Effective date: 19960311