GB885523A - Isocyanato-urethane waterproofing agents and materials waterproofed therewith - Google Patents

Isocyanato-urethane waterproofing agents and materials waterproofed therewith

Info

Publication number
GB885523A
GB885523A GB39505/58A GB3950558A GB885523A GB 885523 A GB885523 A GB 885523A GB 39505/58 A GB39505/58 A GB 39505/58A GB 3950558 A GB3950558 A GB 3950558A GB 885523 A GB885523 A GB 885523A
Authority
GB
United Kingdom
Prior art keywords
materials
hydroxymethylated
adducts
adduct
treated
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
GB39505/58A
Inventor
Clyde Lee Aldridge
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.)
ExxonMobil Technology and Engineering Co
Original Assignee
Exxon Research and Engineering Co
Esso Research and Engineering Co
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
Priority to US668337A priority Critical patent/US3040002A/en
Application filed by Exxon Research and Engineering Co, Esso Research and Engineering Co filed Critical Exxon Research and Engineering Co
Priority to GB39505/58A priority patent/GB885523A/en
Priority to FR781918A priority patent/FR1217948A/en
Priority to US140156A priority patent/US3112984A/en
Publication of GB885523A publication Critical patent/GB885523A/en
Expired legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
    • C08C19/00—Chemical modification of rubber
    • C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
    • C08C19/34—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with oxygen or oxygen-containing groups
    • C08C19/38—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with oxygen or oxygen-containing groups with hydroxy radicals
    • 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
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing 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
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6204—Polymers of olefins
    • 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
    • C08G18/69—Polymers of conjugated dienes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)

Abstract

Materials which contain active hydrogen atoms are waterproofed by reaction with an isocyanatourethane adduct of a diisocyanate OCN.R1.NCO, wherein R1 is a divalent C6-12 hydrocarbon radical, with an aliphatic monohydroxy compound containing at least 10 carbon atoms or with a hydroxymethylated high molecular weight, low unsaturation hydrocarbon polymer containing from 1 to 10 hydroxy groups per thousand carbon atoms. The aliphatic monohydroxy compound may be a C10-30 alkanol or alkoxyalkanol. The polymer may be hydroxymethylated butyl rubber or hydroxymethylated petroleum resins, polypropylene or styrene-diolefin copolymers. Suitable materials for proofing include cellulosic or polysaccharidic materials such as cotton, paper, regenerated cellulose filaments, viscose films, cellulose acetate, and cellulose esters and ethers containing free hydroxy groups, and nitrogen containing fibres, e.g. nylon. The waterproofing is effected by impregnating, (e.g. by dipping or refluxing) the material with a solution, e.g. in hexane, n-heptane or naphtha, of the isocyanatourethane and then drying or baking, e.g. at 30-150 DEG C. Generally 0,1 to 1 % wt. of the alcohol adducts and 0,1 to 10% of the polymer adducts are incorporated in the material. Adduct not chemically bound to the material may be removed by washing with a hydrocarbon. In examples: cotton cloth is treated with adducts from tolylene diisocyanates and C8H17O C9-H18OH, C13 oxo alcohol, or hydroxymethylated butyl rubber; paper is treated with adducts from tolylene diisocyanates and C8H17OC9H18OH o C13 oxo alcohol; and nylon is treated with an adduct from tolylene diisocyanate and C10H21OC11H22OH. Specifications 565,974 and 743,886 are referred to.ALSO:The invention comprises isocyanotourethane compounds of formula OCN.R1.NH.CO.OR wherein R1 is a divalent C6-12 hydrocarbon radical and R is a hydrophobic aliphatic radical containing at least 10 carbon atoms, e.g. a hydrocarbon radical which may be interrupted by an ether oxygen atom or atoms. They are prepared by reacting a diisocyanate OCN.R1. NCO (preferably in excess) with a monohydric alcohol ROH, preferably in an inert solvent. Suitable alcohols include C10-30 alkanols and alkoxyalkanols. The products are used in waterproofing materials containing active hydrogen (see Groups IV (a) and VIII).
GB39505/58A 1957-06-27 1958-12-08 Isocyanato-urethane waterproofing agents and materials waterproofed therewith Expired GB885523A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US668337A US3040002A (en) 1957-06-27 1957-06-27 Isocyanates
GB39505/58A GB885523A (en) 1958-12-08 1958-12-08 Isocyanato-urethane waterproofing agents and materials waterproofed therewith
FR781918A FR1217948A (en) 1957-06-27 1958-12-17 Waterproofing agents and waterproofed products
US140156A US3112984A (en) 1957-06-27 1961-09-07 Waterproofing agents and waterproofed materials

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB39505/58A GB885523A (en) 1958-12-08 1958-12-08 Isocyanato-urethane waterproofing agents and materials waterproofed therewith

Publications (1)

Publication Number Publication Date
GB885523A true GB885523A (en) 1961-12-28

Family

ID=10409909

Family Applications (1)

Application Number Title Priority Date Filing Date
GB39505/58A Expired GB885523A (en) 1957-06-27 1958-12-08 Isocyanato-urethane waterproofing agents and materials waterproofed therewith

Country Status (1)

Country Link
GB (1) GB885523A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1110946A2 (en) * 1999-12-23 2001-06-27 Basf Aktiengesellschaft Subunits containing isocyanate groups and their use for functionalising or modifying compounds or surfaces

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1110946A2 (en) * 1999-12-23 2001-06-27 Basf Aktiengesellschaft Subunits containing isocyanate groups and their use for functionalising or modifying compounds or surfaces
EP1110946A3 (en) * 1999-12-23 2002-04-24 Basf Aktiengesellschaft Subunits containing isocyanate groups and their use for functionalising or modifying compounds or surfaces
US6913629B2 (en) 1999-12-23 2005-07-05 Basf Aktiengesellschaft Building blocks containing isocyanate groups and their use for functionalizing or modifying compounds or surfaces

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