GB2077741A - Non-flammable polyurethane adhesive - Google Patents
Non-flammable polyurethane adhesive Download PDFInfo
- Publication number
- GB2077741A GB2077741A GB8019188A GB8019188A GB2077741A GB 2077741 A GB2077741 A GB 2077741A GB 8019188 A GB8019188 A GB 8019188A GB 8019188 A GB8019188 A GB 8019188A GB 2077741 A GB2077741 A GB 2077741A
- Authority
- GB
- United Kingdom
- Prior art keywords
- adhesive
- ester
- isocyanate
- polyurethane
- tris
- 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.)
- Withdrawn
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 57
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 57
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 19
- 239000004814 polyurethane Substances 0.000 title claims abstract description 19
- 150000002148 esters Chemical class 0.000 claims abstract description 18
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000012948 isocyanate Substances 0.000 claims abstract description 5
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 3
- -1 phosphorus ester Chemical class 0.000 claims description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 230000008018 melting Effects 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000005030 aluminium foil Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 239000004800 polyvinyl chloride Substances 0.000 claims description 4
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 238000004132 cross linking Methods 0.000 claims description 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 2
- 239000004831 Hot glue Substances 0.000 claims description 2
- 239000004698 Polyethylene Substances 0.000 claims description 2
- 239000004743 Polypropylene Substances 0.000 claims description 2
- 230000032683 aging Effects 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 239000004794 expanded polystyrene Substances 0.000 claims description 2
- 238000001125 extrusion Methods 0.000 claims description 2
- 239000004744 fabric Substances 0.000 claims description 2
- 239000006260 foam Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000007654 immersion Methods 0.000 claims description 2
- 238000010348 incorporation Methods 0.000 claims description 2
- 238000009413 insulation Methods 0.000 claims description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 239000004014 plasticizer Substances 0.000 claims description 2
- 229920001610 polycaprolactone Polymers 0.000 claims description 2
- 239000004632 polycaprolactone Substances 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 229920000573 polyethylene Polymers 0.000 claims description 2
- 229920001155 polypropylene Polymers 0.000 claims description 2
- 230000002035 prolonged effect Effects 0.000 claims description 2
- 230000001902 propagating effect Effects 0.000 claims description 2
- 230000009257 reactivity Effects 0.000 claims description 2
- 230000000979 retarding effect Effects 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- 229920001169 thermoplastic Polymers 0.000 claims description 2
- 239000004416 thermosoftening plastic Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
- C08L23/20—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
- C08L23/22—Copolymers of isobutene; Butyl rubber; Homopolymers or copolymers of other iso-olefins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L57/00—Compositions of unspecified polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C08L57/06—Homopolymers or copolymers containing elements other than carbon and hydrogen
- C08L57/10—Homopolymers or copolymers containing elements other than carbon and hydrogen containing oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/04—Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
- C08L2666/06—Homopolymers or copolymers of unsaturated hydrocarbons; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/28—Non-macromolecular organic substances
- C08L2666/40—Phosphorus-containing compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
An adhesive comprises an isocyanate terminated polyurethane or urethane prepolymer and an ester which imparts non-inflammability to the adhesive particularly a tri(2- chloroethyl)ester of phosphoric acid.
Description
SPECIFICATION
Non-flarnmable adhesive
The present invention relates to adhesives and more particularly to non-flammable adhesives incorporating an isocyanate-terminated polyurethane. The base for polyurethane can be caprolacton, ether or polyester.
The use of isocyanate-terminated polyurethanes and urethane propolymers, as adhesives is known. However, such compounds suffer from the disadvantage that they are inflammable.
According to the present invention there is provided an adhesive, comprising an isocyanateterminated polyurethane or urethane prepolymer and an ester which imparts non-inflammability to the adhesive. The ester is preferably a phosphorus ester such as a phosphoric acid ester, for example phosphoric acid tris-(2 chloroethyl)-ester-tris-(2chloroethyl)-orthophosphoric acid ester.
The adhesive may also include styrene and isobutylene polymers of carboxylated vinyl resins where the carboxyl groups provide points of reactivity for crosslinking with polyurethanes.
Praferred embodiments of the invention will now be described. In a first embodiment the starting material is an isocyanate-terminated urethane prepolymer based on MDI (modified di-isocyanate) and polycaprolactone base.
To produce the adhesive 100 parts by weight of this compound are melted and heated to about 1 800C in an atmosphere of nitrogen. 20 to 30 parts by weight of phosphorus ester are separately heated to the same temperature and then stirred into the prepolymer.
The resulting product may be regarded as nonflammable for most purposes; however prolonged heating about 2000C should be avoided. Although its flashpoint is 2250C its vapours will burn at 2500C only when in constant contact with a naked flame. Regarding its flammability characteristics according to ASTM D 1 962-68 the extent of flame spread is a maximum of 20mm.
The product does not contain any free hydroxyl groups and has good compatibility with other materials. The adhesive is air or preferably moisture curable.
A particular advantage of the adhesive is that it need not contain any solvent, which leads to improved safety. Of course, solvents may be included, depending on the particular characteristics required, and ketones, including
Methyl Ethyl Ketone, Acetone, Methylene Chloride and Trichloroethane have all been found to be suitable. An adhesive which is 80% solids may be provided.
The adhesive may be further modified by the incorporation of compatible resins such as styrene and isobutylene copolymers or carboxylated vinyl
resins in amounts from 5 to 100 parts by weight.
This increases the green strength of the material
and, depending upon the amount of polymers
added, the softening point and the open assembly
time may be varied. Melting points of between 60"C and 1200C may be obtained and setting
times ranging from a few seconds to
2-3 minutes.
Thus the above embodiment provides an
adhesive which is non-flammable, has a low
melting point, and has a better thermal stability
than is normally associated with polyurethane. In
addition, it has excellent hydrolysis and ageing
resistance. The adhesive may be used to bond a film to another film, to paper or to aluminium foil.
Substrates of polypropylene, polyethylene,
polyester or polyvinyl chloride may be bonded to themselves or to aluminium foil, paper or board.
Fabrics may be bonded together or to foam, to
provide a soft bond which is mark and dry clean
resistant. The adhesive may also be used to bond insulation to the sheet metal lining of refrigerated containers. The adhesive provides flexibility and can withstand arduous service conditions such as water immersion, temperature fluctuation and exposure to many chemicals and plasticizers. It may also be used to provide a non-flammable coating for a surface, such as a ceiling having plastics tiles.
This polymer has no unreacted isocyanate group. The adhesive produced in this way gives excellent adhesion to plasticised PVC, polycarbonate, polyester, expanded polystyrene, polyurethane etc., and produces good flame retarding properties.
The adhesive produced is a hot melt adhesive.
It may be applied by hot roll coaters, by extrusion or by a spatula. In one application the adhesive which is thermoplastic is extended to form a sheet. The sheet is inserted between two articles to be stuck together and the arrangement is heated. Because of its low melting point, the adhesive melts while the articles and laminate remain unaffected to produce a strong bond which provides a non-flame propagating glue-line.
1. An adhesive comprising an isocyanate terminated polyurethane or urethane prepolymer and an ester which imparts non-inflammability to the adhesive.
2. An adhesive as claimed in claim 1, wherein the ester comprises a phosphorous ester.
3. An adhesive as claimed in claim 1 or 2.
wherein the ester comprises a phosperic acid ester.
4. An adhesive as claimed in claim 1, 2 or 3, wherein the ester is phospheric acid tris-(2 chloroethyl)-ester-tris-(2-chloroethyl)orthophosperic acid ester.
5. An adhesive as claimed in any one of claims
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (6)
1. An adhesive comprising an isocyanate terminated polyurethane or urethane prepolymer and an ester which imparts non-inflammability to the adhesive.
2. An adhesive as claimed in claim 1, wherein the ester comprises a phosphorous ester.
3. An adhesive as claimed in claim 1 or 2.
wherein the ester comprises a phosperic acid ester.
4. An adhesive as claimed in claim 1, 2 or 3, wherein the ester is phospheric acid tris-(2 chloroethyl)-ester-tris-(2-chloroethyl)orthophosperic acid ester.
5. An adhesive as claimed in any one of claims 1 to 4, wherein the adhesive includes styrene and isobutylene polymers or carboxylated vinyl resins with the carboxyl groups providing points of activity for cross linking with polyurethanes.
6. An adhesive as claimed in claim 1 and substantially as described herein.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8019188A GB2077741A (en) | 1980-06-12 | 1980-06-12 | Non-flammable polyurethane adhesive |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8019188A GB2077741A (en) | 1980-06-12 | 1980-06-12 | Non-flammable polyurethane adhesive |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2077741A true GB2077741A (en) | 1981-12-23 |
Family
ID=10513996
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8019188A Withdrawn GB2077741A (en) | 1980-06-12 | 1980-06-12 | Non-flammable polyurethane adhesive |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2077741A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4011060C1 (en) * | 1990-04-05 | 1991-05-08 | W. Doellken & Co. Gmbh, 4300 Essen, De | Use of polyurethane as hot gluing agent for olefin(s) - includes using compsn. contg. polyether and opt. polyester long chain di:ol(s), di:isocyanate and short chain di:ol(s) |
| WO1992018577A1 (en) * | 1991-04-23 | 1992-10-29 | Morton International S.P.A. | Adhesive for bonding a plastic film to a paper support to provide a plastic coating, and particularly suitable for bonding plastic film to sheet paper or cardboard |
| EP0546771A1 (en) * | 1991-12-09 | 1993-06-16 | Gencorp Inc. | Two-component urethame adhesive compositions |
| US5508111A (en) * | 1991-03-13 | 1996-04-16 | Gencorp | Adhesive composition |
| US5606003A (en) * | 1994-09-01 | 1997-02-25 | Gencorp Inc. | Primerless urethane adhesive compositions |
-
1980
- 1980-06-12 GB GB8019188A patent/GB2077741A/en not_active Withdrawn
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4011060C1 (en) * | 1990-04-05 | 1991-05-08 | W. Doellken & Co. Gmbh, 4300 Essen, De | Use of polyurethane as hot gluing agent for olefin(s) - includes using compsn. contg. polyether and opt. polyester long chain di:ol(s), di:isocyanate and short chain di:ol(s) |
| US5508111A (en) * | 1991-03-13 | 1996-04-16 | Gencorp | Adhesive composition |
| WO1992018577A1 (en) * | 1991-04-23 | 1992-10-29 | Morton International S.P.A. | Adhesive for bonding a plastic film to a paper support to provide a plastic coating, and particularly suitable for bonding plastic film to sheet paper or cardboard |
| EP0546771A1 (en) * | 1991-12-09 | 1993-06-16 | Gencorp Inc. | Two-component urethame adhesive compositions |
| US5606003A (en) * | 1994-09-01 | 1997-02-25 | Gencorp Inc. | Primerless urethane adhesive compositions |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |