WO1983003837A1 - Inactivated polyurethane and method for preparing it - Google Patents

Inactivated polyurethane and method for preparing it Download PDF

Info

Publication number
WO1983003837A1
WO1983003837A1 PCT/SE1983/000169 SE8300169W WO8303837A1 WO 1983003837 A1 WO1983003837 A1 WO 1983003837A1 SE 8300169 W SE8300169 W SE 8300169W WO 8303837 A1 WO8303837 A1 WO 8303837A1
Authority
WO
WIPO (PCT)
Prior art keywords
polyurethane
polymer
inactivated
groups
hydroxyl group
Prior art date
Application number
PCT/SE1983/000169
Other languages
English (en)
French (fr)
Inventor
Jaan M. Uustalu
Original Assignee
Protector Agentur Ab
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 Protector Agentur Ab filed Critical Protector Agentur Ab
Publication of WO1983003837A1 publication Critical patent/WO1983003837A1/en

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61LMETHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/22Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
    • A61L15/26Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00Polymeric products of isocyanates or isothiocyanates
    • C08G18/06Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08Processes
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04Coating
    • C08J7/0427Coating with only one layer of a composition containing a polymer binder
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04Polyurethanes
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2429/00Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal, or ketal radical; Hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Derivatives of such polymer
    • C08J2429/02Homopolymers or copolymers of unsaturated alcohols
    • C08J2429/04Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/31504Composite [nonstructural laminate]
    • Y10T428/31551Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
    • Y10T428/31569Next to natural rubber
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/31504Composite [nonstructural laminate]
    • Y10T428/31551Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
    • Y10T428/31573Next to addition polymer of ethylenically unsaturated monomer
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/31504Composite [nonstructural laminate]
    • Y10T428/31551Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
    • Y10T428/31573Next to addition polymer of ethylenically unsaturated monomer
    • Y10T428/31576Ester monomer type [polyvinylacetate, etc.]

Definitions

  • the present invention relates to an inactivated polyurethane and a method, for preparing it,
  • Polyurethane is generally manufactured by a reaction between polyfunctional isocyanates and al- 5 cohols. The finished product then has a certain residual isocyanate content. It has long been known that isocya ⁇ nate molecules are toxic, this having restricted the use of polyurethane to fields where a certain isocyanate content has not been considered harmful. 10 An indication of the toxicity of isocyanate is that the hygienic limit value for its presence in the atmosphere (for instance in a workshop) is at present
  • the object of the present invention therefore is to provide an inactivated polyurethane which can also be used in such products as will come into direct con ⁇ tact with the skin, suc as ear protectors or dressing materials, e.g. plaster.
  • This object is achieved by coating polyurethane with a layer of a polymer which contains functional groups capable of reacting v/ith isocyanate. Free iso ⁇ cyanate groups leaving the polyurethane material will then be prevented not only mechanically from escaping out into the ambient atmosphere but will react with the alcohol groups in the polymer layer and be chemi ⁇ cally bound therein.
  • the coating of the polyurethane can be carried out in various ways.
  • the polyurethane can first be molded to the desired shape and thereafter be coated with a thin layer of a suitable polymer v/hich then reacts with isocyanate groups in the polyurethane.
  • Another mode of producing the coating is first to apply a thin layer of a suitable polymer to the inner side of the mold in v/hich the polyurethane is to be shaped, and then form the polyurethane in the mold.
  • Functional groups in the polymer will then react with isocyanate groups in the polyurethane, whereby the layer of polymer is chemically bonded to the polyurethane.
  • a suitable hydroxyl group containing polymer is e.g. polyvinyl alcohol, but other hydroxyl group con ⁇ taining polymers mav also be used, such as partly hydrolyzed polyvinyl acetate or copolymers containing vinyl alcohol or hydrolyzed polyvinyl acetate, polymers prepared from vinyl and acrylate monomers containing hydroxyl groups, or hydroxyl group-terminated low mole ⁇ cular polyesters.
  • Example v/hich is however not meant in any way to restrict the scope of the present invention.
  • Tests were performed with sheetings of polyethy- lene, polyvinyl alcohol and polyvinyl alcohol treated with a catalyst (DABCO 33 LV) .
  • the catalyst used is of the type employed in the production of polyurethane, and residues of spent catalyst are always present in the finished material. It was found that the amount of isocyanate that had penetrated through the sheeting of polyvinyl alcohol (not treated by catalyst) was about 50 times less than the a- ount that had penetrated through the polyethylene sheet ⁇ ing. The permeability of the catalyst-treated polyv ⁇ nyl alcohol sheeting to isocyanate molecules was still less. A lesser amount of 2,4-TDI than of 2,6-TDI initial ⁇ ly penetrates through the polyvinyl alcohol sheeting.
  • 2,4-TDI is far more reactive than 2,6-TDI, this is indicatxve of a reaction taking place between the isocyanate molucules and the alcohol groups. The more reactive molecule is thus barred to a greater extent by the reactive protective film.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Materials Engineering (AREA)
  • Hematology (AREA)
  • Materials For Medical Uses (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Laminated Bodies (AREA)
PCT/SE1983/000169 1982-05-04 1983-04-28 Inactivated polyurethane and method for preparing it WO1983003837A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE8202776A SE430697B (sv) 1982-05-04 1982-05-04 Inaktiverad polyuretan, sett att framstella denna samt anvendning herav
SE8202776-4 1982-05-04

Publications (1)

Publication Number Publication Date
WO1983003837A1 true WO1983003837A1 (en) 1983-11-10

Family

ID=20346710

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/SE1983/000169 WO1983003837A1 (en) 1982-05-04 1983-04-28 Inactivated polyurethane and method for preparing it

Country Status (5)

Country Link
US (1) US4552817A (sv)
EP (1) EP0108101A1 (sv)
ES (1) ES8402603A1 (sv)
SE (1) SE430697B (sv)
WO (1) WO1983003837A1 (sv)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4808469A (en) * 1985-05-09 1989-02-28 Maurice Hiles Energy absorbing polyurethane composite article
JP5395904B2 (ja) * 2008-08-11 2014-01-22 ダウ グローバル テクノロジーズ エルエルシー フェノールとヒドロキシ末端化アクリレートまたはヒドロキシ末端化メタクリレートとでキャップされたエラストマー型強化剤を含有する一液型構造用エポキシ樹脂接着剤

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2633743A1 (de) * 1975-09-04 1977-03-10 Goodyear Tire & Rubber Verfahren zum verbinden eines polyurethans mit einem gehaerteten kautschukmaterial
EP0006308A1 (en) * 1978-06-08 1980-01-09 Ici Americas Inc. In-mould coating compositions containing functional group terminated liquid polymers and method of covering surface defects of a moulded thermoplastic article therewith
SE421994B (sv) * 1973-04-24 1982-02-15 Ici Ltd Vetskeformig tandfyllnadskompositioner
DE3124982A1 (de) * 1980-06-26 1982-02-25 The General Tire & Rubber Co., 44329 Akron, Ohio Verfahren zur ueberzugsbildung in der form und hierzu geeignete zusammensetzung

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2806215A1 (de) * 1978-02-14 1979-08-16 Bayer Ag Verfahren zur herstellung von formschaumstoffen auf polyisocyanat-basis
JPS5525367A (en) * 1978-08-11 1980-02-23 Toyo Tire & Rubber Co Ltd Method of fabricating polyurethane molded product with skin
US4282285A (en) * 1979-10-24 1981-08-04 International Telephone & Telegraph Corporation Process for preparing polyurethane molded part
DE3014161A1 (de) * 1980-04-12 1981-10-22 Basf Ag, 6700 Ludwigshafen Verfahren zur herstellung von polyurethan-formkoerpern
US4487808A (en) * 1982-04-22 1984-12-11 Astra Meditec Aktiebolag Medical article having a hydrophilic coating

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE421994B (sv) * 1973-04-24 1982-02-15 Ici Ltd Vetskeformig tandfyllnadskompositioner
DE2633743A1 (de) * 1975-09-04 1977-03-10 Goodyear Tire & Rubber Verfahren zum verbinden eines polyurethans mit einem gehaerteten kautschukmaterial
EP0006308A1 (en) * 1978-06-08 1980-01-09 Ici Americas Inc. In-mould coating compositions containing functional group terminated liquid polymers and method of covering surface defects of a moulded thermoplastic article therewith
DE3124982A1 (de) * 1980-06-26 1982-02-25 The General Tire & Rubber Co., 44329 Akron, Ohio Verfahren zur ueberzugsbildung in der form und hierzu geeignete zusammensetzung

Also Published As

Publication number Publication date
ES522030A0 (es) 1984-02-01
SE430697B (sv) 1983-12-05
US4552817A (en) 1985-11-12
SE8202776L (sv) 1983-11-05
EP0108101A1 (en) 1984-05-16
ES8402603A1 (es) 1984-02-01

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