CA1215188A - Adhesive consisting essentially of a recinoleate urethane polyol and a chlorinated polyvinyl chloride - Google Patents
Adhesive consisting essentially of a recinoleate urethane polyol and a chlorinated polyvinyl chlorideInfo
- Publication number
- CA1215188A CA1215188A CA000414638A CA414638A CA1215188A CA 1215188 A CA1215188 A CA 1215188A CA 000414638 A CA000414638 A CA 000414638A CA 414638 A CA414638 A CA 414638A CA 1215188 A CA1215188 A CA 1215188A
- Authority
- CA
- Canada
- Prior art keywords
- ricinoleate
- polyol
- accordance
- adhesive composition
- prepared
- 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
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
- C09J127/00—Adhesives based on 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 a halogen; Adhesives based on derivatives of such polymers
- C09J127/22—Adhesives based on 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 a halogen; Adhesives based on derivatives of such polymers modified by chemical after-treatment
- C09J127/24—Adhesives based on 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 a halogen; Adhesives based on derivatives of such polymers modified by chemical after-treatment halogenated
-
- 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
- C08G18/36—Hydroxylated esters of higher fatty acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions 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 a halogen; Compositions of derivatives of such polymers
-
- 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
- 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
- C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Polyurethanes Or Polyureas (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
An adhesive composition consisting essentially of a solution in a suitable solvent of a ricinoleate urethane polyol and a chlorinated polyvinyl chloride in which the chlorinated polyvinyl chloride represents no more than approximately 90% by weight of the combined polyol and chlorinated polyvinyl chloride.
An adhesive composition consisting essentially of a solution in a suitable solvent of a ricinoleate urethane polyol and a chlorinated polyvinyl chloride in which the chlorinated polyvinyl chloride represents no more than approximately 90% by weight of the combined polyol and chlorinated polyvinyl chloride.
Description
I
A RICINOLEATE URETHANE POLYOL AND A
A RICINOLEATE URETHANE POLYOL AND A
2 CHLORINATED POLYVINYL CHLORIDE
3 BACKGROUND OF Lowe INVENTION
-
-
4 Ricinoleate urethane polyols are well known in the art S for use in the formulation of adhesives and coatings as 6 plasticizers, pigment dispersing agents and tackifiers as 7 well as a reactive ingredient.
8 Ricinoleate urethane polyols themselves vary in consistency 9 from high viscosity oils to greases and, while they have some tack, they lack cohesive strength. Thus, they are not employed 11 alone as pressure sensitive adhesives or contact cement nor 12 do they impart cohesive strength to adhesives when used as 13 tackifiers.
14 Two-package urethane adhesives which cure by the reaction of the hydroxyl groups of the ricinoleate urethane polyol 16 with an isocyanate are strong adhesives when cured but exhibit 17 very little green strength. "Green strength" as used herein 18 means the ability to hold two surfaces together when first 19 contacted and before the adhesive develops its ultimate bonding properties when fully cured.
21 The degree of green strength exhibited by an adhesive 22 is vital to many applications. High green strength tends to 25l/
26~/
I! I
/
l l ': , , .
.
Lo 1 prevent wrinkling and slippage of films during lamination.
2 In panel assembly and packaging, it permits Easter handling 3 and wrapping. When Jan adhesive is applied to a vertical surface, 4 a sufficiently high green strength prevents a mechanically us-supported, bonded member from slipping under the influence off gravity. When employed for flocking, high green strength 7 holds fibers in place while the adhesive cures and in the laying 8 of carpet or synthetic flooring it resists curling due to the 9 shape-memory thereof acquired when stored in a roll.
Two-package urethane coatings which cure by the same reaction as set forth above with respect to adhesives have good flexibility 12 and toughness but develop film hardness slowly. It is preferable 13 that floor coatings develop hardness sufficient to accept traffic 14 rapidly to minimize down-time whether the coating be used on 15 new construction or existing sites.
16 Additionally, when urethane coatings and adhesives are 17 applied to concrete, it is currently necessary to acid-etch I the concrete prior to application. While acid-etching of the 19 concrete is a prerequisite for excellent adhesion, a higher I degree of adhesion to concrete that has not been acid-etched 21 is always desirable by virtue of the fact that when large I areas are acid-etched frequently portions thereof are either 23 missed or inadequately etched resulting in poor adhesion.
24 In accordance with the present invention, it has been found 25 that a mixture of ricinoleate urethane polyol and chlorinated 26 polyvinyl chloride (CPVC) exhibits a unique combination of 27 properties which are not achievable if either product is 28 employed lone or if either product were omitted from certain 29 formulations containing other ingredients. Chlorinated 30 polyvinyl chloride is known for its excellent adhesion to 1 rigid polyvinyl chloride, high tensile strength and inherent 2 flexibility but not as a product known to convert a ricinoleate 3 urethane polyol from a product with little tack and cohesiveness 4 to one that is tenacious as claimed in the present invention.
A chlorinated polyvinyl chloride/ricinoleate urethane polyol mixture in accordance with the present invention is 7 useful in the formulation of pressure sensitive and curable 8 adhesives, contact cements, protective coatings, curable 9 urethanes and curable coatings. Such mixtures are also useful 10 as tackifying additives, anti-slip additives, flexibilizing agents, cross-linking agents, adhesion improvers and the like.
1 The term "adhesive" as used herein is intended to include 13 broadly, adhesives, coatings and all other uses to which the 14 combination of chlorinated polyvinyl chloride and ricinoleate lo urethane polyol may be employed.
_ 18 An adhesive composition consisting essentially of a 19 solution in a suitable solvent of a ricinoleate urethane polyol 20 and a chlorinated polyvinyl chloride with the chlorinated 21 polyvinyl chloride appearing in quantities no greater than 22 approximately 90% by weight of the combined polyol and 23 chlorinated polyvinyl chloride.
I
26 The aforesaid objects and advantages may be achieved from 27 a mixture of chlorinated polyvinyl chloride and a ricinoleate 28 urethane polyol preferred embodiments of which follow.
29 The chlorinated polyvinyl chloride may be made by post I chlorinating polyvinyl chloride resin. Merely by way of : i , 1 example, the following chlorinated polyvinyl chlorides may be * *
2 employed in this invention: GENCLOR S, GENCLOR T manufactured 3 by Imperial Chemical Industries lid, London, England and 4 marketed in the USA by ICY United States, Inc., Wilmington,
8 Ricinoleate urethane polyols themselves vary in consistency 9 from high viscosity oils to greases and, while they have some tack, they lack cohesive strength. Thus, they are not employed 11 alone as pressure sensitive adhesives or contact cement nor 12 do they impart cohesive strength to adhesives when used as 13 tackifiers.
14 Two-package urethane adhesives which cure by the reaction of the hydroxyl groups of the ricinoleate urethane polyol 16 with an isocyanate are strong adhesives when cured but exhibit 17 very little green strength. "Green strength" as used herein 18 means the ability to hold two surfaces together when first 19 contacted and before the adhesive develops its ultimate bonding properties when fully cured.
21 The degree of green strength exhibited by an adhesive 22 is vital to many applications. High green strength tends to 25l/
26~/
I! I
/
l l ': , , .
.
Lo 1 prevent wrinkling and slippage of films during lamination.
2 In panel assembly and packaging, it permits Easter handling 3 and wrapping. When Jan adhesive is applied to a vertical surface, 4 a sufficiently high green strength prevents a mechanically us-supported, bonded member from slipping under the influence off gravity. When employed for flocking, high green strength 7 holds fibers in place while the adhesive cures and in the laying 8 of carpet or synthetic flooring it resists curling due to the 9 shape-memory thereof acquired when stored in a roll.
Two-package urethane coatings which cure by the same reaction as set forth above with respect to adhesives have good flexibility 12 and toughness but develop film hardness slowly. It is preferable 13 that floor coatings develop hardness sufficient to accept traffic 14 rapidly to minimize down-time whether the coating be used on 15 new construction or existing sites.
16 Additionally, when urethane coatings and adhesives are 17 applied to concrete, it is currently necessary to acid-etch I the concrete prior to application. While acid-etching of the 19 concrete is a prerequisite for excellent adhesion, a higher I degree of adhesion to concrete that has not been acid-etched 21 is always desirable by virtue of the fact that when large I areas are acid-etched frequently portions thereof are either 23 missed or inadequately etched resulting in poor adhesion.
24 In accordance with the present invention, it has been found 25 that a mixture of ricinoleate urethane polyol and chlorinated 26 polyvinyl chloride (CPVC) exhibits a unique combination of 27 properties which are not achievable if either product is 28 employed lone or if either product were omitted from certain 29 formulations containing other ingredients. Chlorinated 30 polyvinyl chloride is known for its excellent adhesion to 1 rigid polyvinyl chloride, high tensile strength and inherent 2 flexibility but not as a product known to convert a ricinoleate 3 urethane polyol from a product with little tack and cohesiveness 4 to one that is tenacious as claimed in the present invention.
A chlorinated polyvinyl chloride/ricinoleate urethane polyol mixture in accordance with the present invention is 7 useful in the formulation of pressure sensitive and curable 8 adhesives, contact cements, protective coatings, curable 9 urethanes and curable coatings. Such mixtures are also useful 10 as tackifying additives, anti-slip additives, flexibilizing agents, cross-linking agents, adhesion improvers and the like.
1 The term "adhesive" as used herein is intended to include 13 broadly, adhesives, coatings and all other uses to which the 14 combination of chlorinated polyvinyl chloride and ricinoleate lo urethane polyol may be employed.
_ 18 An adhesive composition consisting essentially of a 19 solution in a suitable solvent of a ricinoleate urethane polyol 20 and a chlorinated polyvinyl chloride with the chlorinated 21 polyvinyl chloride appearing in quantities no greater than 22 approximately 90% by weight of the combined polyol and 23 chlorinated polyvinyl chloride.
I
26 The aforesaid objects and advantages may be achieved from 27 a mixture of chlorinated polyvinyl chloride and a ricinoleate 28 urethane polyol preferred embodiments of which follow.
29 The chlorinated polyvinyl chloride may be made by post I chlorinating polyvinyl chloride resin. Merely by way of : i , 1 example, the following chlorinated polyvinyl chlorides may be * *
2 employed in this invention: GENCLOR S, GENCLOR T manufactured 3 by Imperial Chemical Industries lid, London, England and 4 marketed in the USA by ICY United States, Inc., Wilmington,
5 Delaware and GOON 625X560, GOON 623X560 manufactured my
6 B. F. Goodrich Chemical Group, Cleveland, Ohio.
7 The chlorinated polyvinyl chloride content by weight should
8 not be more than approximately 90% of the chlorinated polyvinyl
9 chloride/ricinoleate urethane polyol blend. This percentage
10 excludes changes resulting from adding plasticizers, solvents,
11 fillers and the like.
12 The ricinoleate urethane polyol of this invention is made
13 by reacting an isocyanate having an average functionality of two
14 or greater with a ricinoleate polyol having an average hydroxyl lo functionality of two or greater at an isocyanate/hydroxyl 16 (NCO/OH) ratio of no greater than 0.9/1Ø The ricinoleate 17 urethane polyol resulting from this reaction substantially has 18 no reactive isocyanate groups but does have residual unrequited 19 hydroxyl groups. The methods of preparation of polyol/isocyanate 20 adduces such as the ricinoleate urethane polyol above are well 21 known in the art and need no further explanation.
22 Both aromatic and aliphatic polyisocyanates can be employed I to react with the ricinoleate polyol to make the ricinoleate 24 urethane polyol of this invention. The preferred isocyanates are Tulane diisocyanate (TDI) and diphenylmethane diisocyanate I (MID). Illustrative of other suitable polyisocyanates are 27 the following: Isophorone diisocyanate (IPDI), 4~4'4"
28 triphenylmethane triisocyanate, polyethylene polyphenyl 29 isocyanate m-phenylene, l-chlorophenylene 2,4 diisocyanates, 30 methylene-bis (4-cyclohexylisocyanate) and their equivalents.
* Tracemari;
1 The chlorinated polyvinyl chloride may be combined with the 2 ricinoleate urethane polyol by several methods. Merely by way 3 of illustration and without limiting the scope of the claims 4 hereof, some of the methods are: (a) the chlorinated polyvinyl 5 is dissolve d in the components employed in the preparation of 6 the ricinoleate urethane polyol prior to or during the reaction 7 process; by the chlorinated polyvinyl chloride is dissolved 8 in the finished ricinoleate urethane polyol; and (c) the chlorinated polyvinyl chloride is added Jo the ricinoleate 10 urethane polyol as a solution of chlorinated polyvinyl chloride dissolved in a solvent, or dissolved in a non-reactive resin or 12 a non-reactive plasticizer or combination of the same; (d) a 13 chlorinated polyvinyl chloride is added to the ricinoleate 14 urethane polyol by first dissolving in isocyanates, in blocked
22 Both aromatic and aliphatic polyisocyanates can be employed I to react with the ricinoleate polyol to make the ricinoleate 24 urethane polyol of this invention. The preferred isocyanates are Tulane diisocyanate (TDI) and diphenylmethane diisocyanate I (MID). Illustrative of other suitable polyisocyanates are 27 the following: Isophorone diisocyanate (IPDI), 4~4'4"
28 triphenylmethane triisocyanate, polyethylene polyphenyl 29 isocyanate m-phenylene, l-chlorophenylene 2,4 diisocyanates, 30 methylene-bis (4-cyclohexylisocyanate) and their equivalents.
* Tracemari;
1 The chlorinated polyvinyl chloride may be combined with the 2 ricinoleate urethane polyol by several methods. Merely by way 3 of illustration and without limiting the scope of the claims 4 hereof, some of the methods are: (a) the chlorinated polyvinyl 5 is dissolve d in the components employed in the preparation of 6 the ricinoleate urethane polyol prior to or during the reaction 7 process; by the chlorinated polyvinyl chloride is dissolved 8 in the finished ricinoleate urethane polyol; and (c) the chlorinated polyvinyl chloride is added Jo the ricinoleate 10 urethane polyol as a solution of chlorinated polyvinyl chloride dissolved in a solvent, or dissolved in a non-reactive resin or 12 a non-reactive plasticizer or combination of the same; (d) a 13 chlorinated polyvinyl chloride is added to the ricinoleate 14 urethane polyol by first dissolving in isocyanates, in blocked
15 isocyanates,in reactive phenolics, in melamine-formaldehyde,
16 in urea-formaldehyde or other resins that will chemically react
17 with the ricinoleate urethane polyol. In some cases when adding the chlorinated polyvinyl chloride by this method the chlorinated lo polyvinyl chloride would be in to part of a two-package system 20 which reacts with the other part which is the ricinoleate 21 urethane polyol.
22 The following examples are illustrative of the adhesives 23 and coatings claimed herein:
This example discloses the formulation, properties, 26 performance and testing of a two-package curing urethane 27 adhesive in accordance with the invention claimed herein. The 28 adhesive cures by the reaction of the hydroxyl groups on the 29 ricinoleate urethane polyol with the isocyanate terminated 30 prepolymer.
' 1 FORMULA Wt. Wt. Wt.
.
2 Par t A A B C
3 Ricinoleate urethane polyol~'; 35 35 35 4 CPVC solution (20% by weight solids* -- 325 --6 Methyl Ethyl Kitten 35 Jo Jo 7 Gaston oil/TDI adduce (88/12 by weight having 8 2.1% by weight available hydroxyl expressed as Levi by weight solids; with a viscosity of 90,000 cups.
`
ISSUE Genclor-S dissolved in ME.
11 Part B
13 Isocyanate Terminated urethane 14 prepolymer'~ * 45.3 45.3 45.3 CPVC solution (20% by weight solids Jo 325.0 17 Castro old prepolymer having 4.1% by weight 8 available isocyanates as a 70% by weight solids 1 solution in methyl ethyl kitten.
19 *-'ISSUE Genclor-S dissolved in ME.
Those formulas of Parts A and B which contain CPVC, 21 when mixed result in the same composition.
22 Performance - The data in Table I illustrates the improvement in 23 green strength between the control and the adhesive of this 24 example.
Table 1 26 Genclor-S (V/o by weight of ricinoleate urethane polyol) 0 65 28 Genclor-S (% by weight of prepolymer) 0 67 29 Genclor-S (% by weight of total solids) 0 49 Finger Tack Oily Tacky, legs 1 Green Strength (finger) Poor Fair 2 Green Strength*** 0.2 6.5 3 Bond Strength (7 days)*'** 6 10 4 assay determined by a Scott Pendulum Type Tensile Tester the readings being employed for comparative purposes.
6 Mixing and Test Procedure - The data listed in Table was 7 determined in the following manner:
8 (A) Part A and B were mixed and allowed to stand at ambient 9 temperature for thirty minutes before beginning to make test 10 samples-11 (B) Finger Tack - An 8 mill wet film was cast on glass using 12 a draw down blade. The film was given approximately a live 13 minute open time to allow the solvent to evaporate. An index 14 finger was pressed into the adhesive, withdrawn slowly, and 15 based on its "feel" was rated us oily or tacky. In the latter 16 case, a material rated as tacky not only had tack but also had 17 a high green strength, legs and grab.
22 The following examples are illustrative of the adhesives 23 and coatings claimed herein:
This example discloses the formulation, properties, 26 performance and testing of a two-package curing urethane 27 adhesive in accordance with the invention claimed herein. The 28 adhesive cures by the reaction of the hydroxyl groups on the 29 ricinoleate urethane polyol with the isocyanate terminated 30 prepolymer.
' 1 FORMULA Wt. Wt. Wt.
.
2 Par t A A B C
3 Ricinoleate urethane polyol~'; 35 35 35 4 CPVC solution (20% by weight solids* -- 325 --6 Methyl Ethyl Kitten 35 Jo Jo 7 Gaston oil/TDI adduce (88/12 by weight having 8 2.1% by weight available hydroxyl expressed as Levi by weight solids; with a viscosity of 90,000 cups.
`
ISSUE Genclor-S dissolved in ME.
11 Part B
13 Isocyanate Terminated urethane 14 prepolymer'~ * 45.3 45.3 45.3 CPVC solution (20% by weight solids Jo 325.0 17 Castro old prepolymer having 4.1% by weight 8 available isocyanates as a 70% by weight solids 1 solution in methyl ethyl kitten.
19 *-'ISSUE Genclor-S dissolved in ME.
Those formulas of Parts A and B which contain CPVC, 21 when mixed result in the same composition.
22 Performance - The data in Table I illustrates the improvement in 23 green strength between the control and the adhesive of this 24 example.
Table 1 26 Genclor-S (V/o by weight of ricinoleate urethane polyol) 0 65 28 Genclor-S (% by weight of prepolymer) 0 67 29 Genclor-S (% by weight of total solids) 0 49 Finger Tack Oily Tacky, legs 1 Green Strength (finger) Poor Fair 2 Green Strength*** 0.2 6.5 3 Bond Strength (7 days)*'** 6 10 4 assay determined by a Scott Pendulum Type Tensile Tester the readings being employed for comparative purposes.
6 Mixing and Test Procedure - The data listed in Table was 7 determined in the following manner:
8 (A) Part A and B were mixed and allowed to stand at ambient 9 temperature for thirty minutes before beginning to make test 10 samples-11 (B) Finger Tack - An 8 mill wet film was cast on glass using 12 a draw down blade. The film was given approximately a live 13 minute open time to allow the solvent to evaporate. An index 14 finger was pressed into the adhesive, withdrawn slowly, and 15 based on its "feel" was rated us oily or tacky. In the latter 16 case, a material rated as tacky not only had tack but also had 17 a high green strength, legs and grab.
18 (C) Green Strength (Finger Test) - An 8 mill wet film was
19 cast on glass using a draw down blade. The film was given approximately five minutes open time in order to allow the 21 solvent to evaporate The relative green strength was determined 22 subjectively by pressing an index finger into the adhesive and I removing it slowly. A green strength rating of ] or poor 24 indicates that little force was necessary to remove one's finger and a rating of 10 or excellent means that a very high force was 26 required to pull away from the glass.
27 (D) Green Strength (Scott Pendulum Type Tensile Tester) -28 A 5 mill wet film, 1" wide and 3" long, was cast on an aluminum 29 panel using a draw down blade. After five minutes open time to allow the solvent to evaporate, a piece of natural cotton fabric 1, 1 1 was pressed into the adhesive and rolled using a 2 pound weight.
2 The relative green strength of this lamination was determined 3 by immediately placing it in the Scott Pendulum Type Tensile 4 Tester and pulling the aluminum and fabric in opposite directions (shear adhesion). The numbers recorded were direct readings from 6 the tester with the lowest numbers being the poorest green 7 strength and the highest numbers being the strongest.
8 (E) Bond Strength - The solution was applied to two pipes 9 of Al wide natural cotton fabric using a paint brush. After a 10 five minute open time to allow the solvent to evaporate, the two 11 coated pieces of fabric were then pressed together like contact I cement. After curing, the samples were subjected to a 90 Peel 13 Strength Test using the Scott Pendulum Type Tensile Tester by 14 pulling apart at a rate of about 2 inches/minute. The numbers 15 shown are the direct readings from the tester with the lowest 16 number being the weakest bond and the highest number being the 17 strongest peel strength.
19 The principal difference between the two-package curing
27 (D) Green Strength (Scott Pendulum Type Tensile Tester) -28 A 5 mill wet film, 1" wide and 3" long, was cast on an aluminum 29 panel using a draw down blade. After five minutes open time to allow the solvent to evaporate, a piece of natural cotton fabric 1, 1 1 was pressed into the adhesive and rolled using a 2 pound weight.
2 The relative green strength of this lamination was determined 3 by immediately placing it in the Scott Pendulum Type Tensile 4 Tester and pulling the aluminum and fabric in opposite directions (shear adhesion). The numbers recorded were direct readings from 6 the tester with the lowest numbers being the poorest green 7 strength and the highest numbers being the strongest.
8 (E) Bond Strength - The solution was applied to two pipes 9 of Al wide natural cotton fabric using a paint brush. After a 10 five minute open time to allow the solvent to evaporate, the two 11 coated pieces of fabric were then pressed together like contact I cement. After curing, the samples were subjected to a 90 Peel 13 Strength Test using the Scott Pendulum Type Tensile Tester by 14 pulling apart at a rate of about 2 inches/minute. The numbers 15 shown are the direct readings from the tester with the lowest 16 number being the weakest bond and the highest number being the 17 strongest peel strength.
19 The principal difference between the two-package curing
20 urethane adhesive of this example and that of Example I is
21 that a different isocyanate terminated prepolymer was employed.
22 The test procedures were the same as in Example I.
23 FURL Wt. We. i _
24 Part A A B
I Ricinoleate urethane polyol* 780 780 26 CPVC solution (23% by weight solids -- 178 27 Dibutyltin dilaurate catalyst 28 Tulane 205 68 29 *Castor oil/TDI adduce: having 2.1% by weight available hydroxyl expressed as 100% by weight solids with a viscosity of 90,000 cups.
1 8.
ICY Genclor-S dissolved in methyl ethyl kitten (ME).
2 Par B
3 Isocyanate terminated urethane prepolymer*~'~* 325 325 mob Chemical Mender I 75: Trimethylol preappointed prepolymer having 13.0% by molecular weight available 6isocyanate as a 75D~ by weight solids solution in methyl acetate by weight.
8 Performance - The data in Table II illustrates the improvement in 9 Green strength ennui the adhesive of the control and that of 10 this example-llTable II
12 Genclor-S, (% by weight ricinoleate urethane polyol) 0 5.0 14 Genclor-S, (% by weight total solids) 0 3,9 Finger Tack Oily Tacky legs 16 Green Strength (finger) Poor Good 17 Green Strength to 0.2 0.6 18 Bond Strength (48 his 5 5 lo As determined by a Scott Pendulum Type Tensile Tester;
the readings being employed for comparative purposes.
EXAMPLE III
_ _ I The principal difference between the adhesive of this 23 ex~nple and that of Example II is that the ricinoleate urethane polyol in this example was made from the reaction of castor oil/
I Ricinoleate urethane polyol* 780 780 26 CPVC solution (23% by weight solids -- 178 27 Dibutyltin dilaurate catalyst 28 Tulane 205 68 29 *Castor oil/TDI adduce: having 2.1% by weight available hydroxyl expressed as 100% by weight solids with a viscosity of 90,000 cups.
1 8.
ICY Genclor-S dissolved in methyl ethyl kitten (ME).
2 Par B
3 Isocyanate terminated urethane prepolymer*~'~* 325 325 mob Chemical Mender I 75: Trimethylol preappointed prepolymer having 13.0% by molecular weight available 6isocyanate as a 75D~ by weight solids solution in methyl acetate by weight.
8 Performance - The data in Table II illustrates the improvement in 9 Green strength ennui the adhesive of the control and that of 10 this example-llTable II
12 Genclor-S, (% by weight ricinoleate urethane polyol) 0 5.0 14 Genclor-S, (% by weight total solids) 0 3,9 Finger Tack Oily Tacky legs 16 Green Strength (finger) Poor Good 17 Green Strength to 0.2 0.6 18 Bond Strength (48 his 5 5 lo As determined by a Scott Pendulum Type Tensile Tester;
the readings being employed for comparative purposes.
EXAMPLE III
_ _ I The principal difference between the adhesive of this 23 ex~nple and that of Example II is that the ricinoleate urethane polyol in this example was made from the reaction of castor oil/
25 IT whereas in Example II, it was made from castor oll/TDI. The
26 test procedures were the same as in Example I.
27 FURL Wt. Wt.
I Part A A B_ 29 Ricinoleate urethane polyol* 1084 1084 30 CPVC solution (23% by weight solids)** -- 124 * Trademark I3ibutyltin dilaurate catalyst 1. 0 1. 0 2 'castor old ~90/10) adduce: having Lyle by weight 3 theoretically available hydroxyl as a 50% by weight solids solution in methyl ethyl kitten.
4 ICY Genclor-S dissolved in EKE.
S Part B
6 Isocyanate terminated urethane 325 325 prepolymer~
8 'mob Chemical Mondur_CB 75: Trimethylol preappointed prepolymer having 13.0% by weight mailable isocyanate 9 as a ~5~/0 by weight solids solution in ethyl acetate lo by weight.
11 Performance - the data in Table III illustrates the difference 12 in green strength between the adhesive of the control and that 13 of this example.
14 Table III
Genclor-S, (% by weight of ricinoleate 0 5.0 16 Genclor-S, (% by weight of total solids) O 3.9 17 Finger Tack Oily Tacky legs 18 Green Strength finger) Poor Good lo Green Strength';* 0.0 0.4 Bond Strength (7 days)*';-;'; 12.0 12.5 byway determined by a Scot Pendul~ Type Tensile Tester;
Thea readings being employed for comparative purposes.
EXAMPLE IV
Lucy example discloses the formulation, properties, per-pheromones and testing of a non-curing pressure sensitive adhesive 26 in accordance with this invention. It develops its Properties I when the solvent evaporates and without undergoing further
I Part A A B_ 29 Ricinoleate urethane polyol* 1084 1084 30 CPVC solution (23% by weight solids)** -- 124 * Trademark I3ibutyltin dilaurate catalyst 1. 0 1. 0 2 'castor old ~90/10) adduce: having Lyle by weight 3 theoretically available hydroxyl as a 50% by weight solids solution in methyl ethyl kitten.
4 ICY Genclor-S dissolved in EKE.
S Part B
6 Isocyanate terminated urethane 325 325 prepolymer~
8 'mob Chemical Mondur_CB 75: Trimethylol preappointed prepolymer having 13.0% by weight mailable isocyanate 9 as a ~5~/0 by weight solids solution in ethyl acetate lo by weight.
11 Performance - the data in Table III illustrates the difference 12 in green strength between the adhesive of the control and that 13 of this example.
14 Table III
Genclor-S, (% by weight of ricinoleate 0 5.0 16 Genclor-S, (% by weight of total solids) O 3.9 17 Finger Tack Oily Tacky legs 18 Green Strength finger) Poor Good lo Green Strength';* 0.0 0.4 Bond Strength (7 days)*';-;'; 12.0 12.5 byway determined by a Scot Pendul~ Type Tensile Tester;
Thea readings being employed for comparative purposes.
EXAMPLE IV
Lucy example discloses the formulation, properties, per-pheromones and testing of a non-curing pressure sensitive adhesive 26 in accordance with this invention. It develops its Properties I when the solvent evaporates and without undergoing further
28 chemical reaction whereas in Examples I, II, and III the adhesives
29 cure by reaction.
10.
DO
1 FORMULA White. Wt.
3 Ricinoleate Urania polyol (50% by weight solids)* 180.0 180.0 CPVC solution (23% by weight solids 43.4 6 Castro oil/MDL ~84.5/15.5) adduce having 0~8% by weight 7 theoretically available hydroxyl as a 50% by weight solids solution in ME.
8 **Genclor-S dissolved in ME.
9 Performance - The data in Table IV illustrates the difference .
in bond strength between the adhesive of the control and that 11 of this example.
Table_IV
13 Genclor-S, (% by weight of total solids) 0 10 14 Bond Strength 0.1 I
(Paper tears) 16 'Casey determined by a Scott Pendulum Type Tensile Tester;
the readings being employed for comparative purposes.
18 Test Procedure - An 8 mill wet film was cast on clay coated paper lo using a draw down blade. It was then dried for ten minutes at 20 ambient temperature and for an additional five minutes at 138F.
21 to drive off all of the solvent. After cooling to room 22 temperature a l inch wide piece was pressed on a piece of cold 23 rolled steel. The samples were subjected to a 180 Peel Strength 24 Test using the Scott Pendulum Type Tensile Tester by pulling at 25 a rate of about 12 inches/minute. The numbers shown are direct 26 readings from ye tester with the lower numbers being the weaker 27 bond and the higher numbers being the stronger bond.
I EXAMPLE V
29 The principal difference between the pressure-sensitive
10.
DO
1 FORMULA White. Wt.
3 Ricinoleate Urania polyol (50% by weight solids)* 180.0 180.0 CPVC solution (23% by weight solids 43.4 6 Castro oil/MDL ~84.5/15.5) adduce having 0~8% by weight 7 theoretically available hydroxyl as a 50% by weight solids solution in ME.
8 **Genclor-S dissolved in ME.
9 Performance - The data in Table IV illustrates the difference .
in bond strength between the adhesive of the control and that 11 of this example.
Table_IV
13 Genclor-S, (% by weight of total solids) 0 10 14 Bond Strength 0.1 I
(Paper tears) 16 'Casey determined by a Scott Pendulum Type Tensile Tester;
the readings being employed for comparative purposes.
18 Test Procedure - An 8 mill wet film was cast on clay coated paper lo using a draw down blade. It was then dried for ten minutes at 20 ambient temperature and for an additional five minutes at 138F.
21 to drive off all of the solvent. After cooling to room 22 temperature a l inch wide piece was pressed on a piece of cold 23 rolled steel. The samples were subjected to a 180 Peel Strength 24 Test using the Scott Pendulum Type Tensile Tester by pulling at 25 a rate of about 12 inches/minute. The numbers shown are direct 26 readings from ye tester with the lower numbers being the weaker 27 bond and the higher numbers being the stronger bond.
I EXAMPLE V
29 The principal difference between the pressure-sensitive
30 adhesive of this example and that of Example IV is that in this 11 .
1 example the ricinoleate urethane polyol was made from an aliphatic 2 isocyanate whereas in Example IV an aromatic isocyanate was 3 employed. me test procedures were the same as Example IV.
s Wt._ Wt.
6 Ricinoleate urethane polyol* 170 170 7 CPVC solution (20% by weight solids)~iJ~ 75 9 Caesar oil/IPDI (86~14) adduce hiving 1.1% by weight theoretically available hydroxyl as a 50% by weight I solids solution in methyl ethyl kitten and Tulane 11 at 1:1 by weight.
12 *ISSUE Genclor-S dissolved in ME.
13 Performance - The data in Table V illustrates the difference 14 between the control and the adhesive of this example.
Table 16 Genclor~S, (% by weight of total solids) 0 15 17 Finger Tack Oily Moderate 18 Bond Strength*** 0 1.5 Lucy determined by a Scott Pendulum Type Tensile Tester, Thea readings being employed for comparative purposes.
EXAMPLE VI
thus example discloses a one-package, thermoplastic coating 23 that dries by solvent evaporation. The principal difference 24 between the coating of this example and that of Example VII is 25 that in Example VII the coating is a two-package system that 26 cures by reaction instead ox remaining thermoplastic.
27 FORMULA Wt.
__ 28Ricinoleate urethane polyol'~ 30 2~CPVC solution (23% by weight solids'; 87 12, ... . . . . . . . . . .
l *Castor oil/TDI adduce having owe by weight available hydroxyl as a 100% by weight solids 2 solution with a viscosity of 90,000 cups.
3 ISSUE Genclor-S dissolved in ME.
4 Performance - The data in Table VI illustrates that composition of this invention can be employed to make a one-package thermos 6 plastic coating that dries by solvent evaporation.
7 Table VI
Genclor-S, (% by weight solids) 40 g Hardness (Sword Rocker 24 hour drycXx 4 Water spot test A
if 95% ethyl alcohol Spot test~X`x`~b A
12 Test Procedure - 7':J;~XAn 8 mill wet film was cast on glass using 13 a draw down blade. After an overnight dry, the sword hardness 14 was determined. Resistance to attack from splashing chemicals 15 was determined by putting two drops of the liquid test solution 16 on the film and rubbing lightly with a finger. If there was no 17 noticeable softening or change in appearance, the film was 18 rated "A" for acceptable.
I The principal difference between the two-package system of 21 this example and Example II is that in this example the formula-Sheehan is evaluated as a coating whereas Example II was evaluated 23 as an adhesive.
24 FORMULA Wt. Wt. Wit _ _ _ _ _ _ Part A A B C
_. _ _ _ _ _ 26 Ricinoleate urethane polyol~ 780 780 780 27 CPVC solution (23% by weight solids)** -- 1453 2260 29 Tulane 1170 -- --Dibutyltin dilaurate catalyst 1.0 1.0 1.0 13.
I Lo l Castro oil/TDI adduce having 2.1% by weight available hydroxyl as a 100% by weight solids solution with a 2 viscosity of 90,Q00 cups.
3 **ICY Genclor-S dissolved in ME.
4 Part B
Isocyanate terminated 325 325 325 prepolymer~
7 -I Moray Chemical Mender CB_75: Trimethylol preappointed prepolymer having owe by weight available isocyanate 8 as a 75% by weight solids solution in ethyl acetate 9 by weight.
10 Performance - The data in Table VII illustrates the improvement if in film hardness and improvement in concrete adhesion of the 12 coating of this example as compared to that of the control.
13 Table VII
14 Genclor-S 7 (% by weight of ricinoleate urethane polyol) 0 30 60 16 Genclor-S, (% by weight of total 17 solids) 0 25 34 18 Hardness (Sword Rocker), 4 hours 0 3 6 19 Hardness (Sword Wrecker hours 4 8 18 Wet concrete adhesion Poor Fair Fair 21 icing and Test Procedure - The data listed in Table VII was 22 determined in the following manner:
23 (A) Part A and Part B were mixed and allowed to stand at I ambient temperature for approximately thirty minutes before 25 beginning to make test samples.
26 (B) Hardness - An 8 mill wet film was cast on glass using 27 a draw down blade. After allowing an air dry for the time 28 indicated in the table, the hardness was determined using a 29 Sword Rocker; the higher the number the greater the hardness.
I
l (C) Wet Concrete adhesion - m e solution was brushed on a 2 block of concrete and allowed to cure at room temperature for 3 3 days. The block was then immersed in water for 24 hours.
4 The adhesion was determined subjectively by picking at it with 5 a knife point.
7 The principal difference between the coatings of this 8 example and that of Example VI is that the chlorinated polyvinyl 9 chlorides of this example are from another manufacturer.
10 FORMULA Wt. White.
12 Ricinoleate urethane polyol (50% by weight solids)* 20 20 14 CPVC solution (20% by weight solids'; 116 --CPVC solution (20% by weight solids 116 Castro oil/TDI adduce having 2.1% by weight available 17hydroxyl as a 100% by weight solids solution with a viscosity of 90,000 cups. mixed with tetrahydrofuran (THY).
19*~';B. F. Goodrich coon 625X560 dissolved in tetrahydrofuran (THY).
21*~';*B. F. Goodrich coon 623X560 dissolved in tetrahydrofuran (THY).
I
23 Performance - The data in Table VIII are additional illustrations 24 ox compositions of this invention that can be employed as one-25 package thermoplastic coatings that dry by solvent evaporation.
tubule VIII
27 CPVC solution (% by weight solids) 70 70 28 Hardness (Sword Rocker), 24 hour dry '; 30 30 29 Water spot test '; A A
95% ethyl alcohol spot Taoist'; A A
1 example the ricinoleate urethane polyol was made from an aliphatic 2 isocyanate whereas in Example IV an aromatic isocyanate was 3 employed. me test procedures were the same as Example IV.
s Wt._ Wt.
6 Ricinoleate urethane polyol* 170 170 7 CPVC solution (20% by weight solids)~iJ~ 75 9 Caesar oil/IPDI (86~14) adduce hiving 1.1% by weight theoretically available hydroxyl as a 50% by weight I solids solution in methyl ethyl kitten and Tulane 11 at 1:1 by weight.
12 *ISSUE Genclor-S dissolved in ME.
13 Performance - The data in Table V illustrates the difference 14 between the control and the adhesive of this example.
Table 16 Genclor~S, (% by weight of total solids) 0 15 17 Finger Tack Oily Moderate 18 Bond Strength*** 0 1.5 Lucy determined by a Scott Pendulum Type Tensile Tester, Thea readings being employed for comparative purposes.
EXAMPLE VI
thus example discloses a one-package, thermoplastic coating 23 that dries by solvent evaporation. The principal difference 24 between the coating of this example and that of Example VII is 25 that in Example VII the coating is a two-package system that 26 cures by reaction instead ox remaining thermoplastic.
27 FORMULA Wt.
__ 28Ricinoleate urethane polyol'~ 30 2~CPVC solution (23% by weight solids'; 87 12, ... . . . . . . . . . .
l *Castor oil/TDI adduce having owe by weight available hydroxyl as a 100% by weight solids 2 solution with a viscosity of 90,000 cups.
3 ISSUE Genclor-S dissolved in ME.
4 Performance - The data in Table VI illustrates that composition of this invention can be employed to make a one-package thermos 6 plastic coating that dries by solvent evaporation.
7 Table VI
Genclor-S, (% by weight solids) 40 g Hardness (Sword Rocker 24 hour drycXx 4 Water spot test A
if 95% ethyl alcohol Spot test~X`x`~b A
12 Test Procedure - 7':J;~XAn 8 mill wet film was cast on glass using 13 a draw down blade. After an overnight dry, the sword hardness 14 was determined. Resistance to attack from splashing chemicals 15 was determined by putting two drops of the liquid test solution 16 on the film and rubbing lightly with a finger. If there was no 17 noticeable softening or change in appearance, the film was 18 rated "A" for acceptable.
I The principal difference between the two-package system of 21 this example and Example II is that in this example the formula-Sheehan is evaluated as a coating whereas Example II was evaluated 23 as an adhesive.
24 FORMULA Wt. Wt. Wit _ _ _ _ _ _ Part A A B C
_. _ _ _ _ _ 26 Ricinoleate urethane polyol~ 780 780 780 27 CPVC solution (23% by weight solids)** -- 1453 2260 29 Tulane 1170 -- --Dibutyltin dilaurate catalyst 1.0 1.0 1.0 13.
I Lo l Castro oil/TDI adduce having 2.1% by weight available hydroxyl as a 100% by weight solids solution with a 2 viscosity of 90,Q00 cups.
3 **ICY Genclor-S dissolved in ME.
4 Part B
Isocyanate terminated 325 325 325 prepolymer~
7 -I Moray Chemical Mender CB_75: Trimethylol preappointed prepolymer having owe by weight available isocyanate 8 as a 75% by weight solids solution in ethyl acetate 9 by weight.
10 Performance - The data in Table VII illustrates the improvement if in film hardness and improvement in concrete adhesion of the 12 coating of this example as compared to that of the control.
13 Table VII
14 Genclor-S 7 (% by weight of ricinoleate urethane polyol) 0 30 60 16 Genclor-S, (% by weight of total 17 solids) 0 25 34 18 Hardness (Sword Rocker), 4 hours 0 3 6 19 Hardness (Sword Wrecker hours 4 8 18 Wet concrete adhesion Poor Fair Fair 21 icing and Test Procedure - The data listed in Table VII was 22 determined in the following manner:
23 (A) Part A and Part B were mixed and allowed to stand at I ambient temperature for approximately thirty minutes before 25 beginning to make test samples.
26 (B) Hardness - An 8 mill wet film was cast on glass using 27 a draw down blade. After allowing an air dry for the time 28 indicated in the table, the hardness was determined using a 29 Sword Rocker; the higher the number the greater the hardness.
I
l (C) Wet Concrete adhesion - m e solution was brushed on a 2 block of concrete and allowed to cure at room temperature for 3 3 days. The block was then immersed in water for 24 hours.
4 The adhesion was determined subjectively by picking at it with 5 a knife point.
7 The principal difference between the coatings of this 8 example and that of Example VI is that the chlorinated polyvinyl 9 chlorides of this example are from another manufacturer.
10 FORMULA Wt. White.
12 Ricinoleate urethane polyol (50% by weight solids)* 20 20 14 CPVC solution (20% by weight solids'; 116 --CPVC solution (20% by weight solids 116 Castro oil/TDI adduce having 2.1% by weight available 17hydroxyl as a 100% by weight solids solution with a viscosity of 90,000 cups. mixed with tetrahydrofuran (THY).
19*~';B. F. Goodrich coon 625X560 dissolved in tetrahydrofuran (THY).
21*~';*B. F. Goodrich coon 623X560 dissolved in tetrahydrofuran (THY).
I
23 Performance - The data in Table VIII are additional illustrations 24 ox compositions of this invention that can be employed as one-25 package thermoplastic coatings that dry by solvent evaporation.
tubule VIII
27 CPVC solution (% by weight solids) 70 70 28 Hardness (Sword Rocker), 24 hour dry '; 30 30 29 Water spot test '; A A
95% ethyl alcohol spot Taoist'; A A
31 20% hydrochloric acid spot Taoist';* A A
15, ****The test procedure was the same as Example VI.
It will be understood by those skilled in the art that many modifications and variations of the present invention may be made without departing from the spirit and the scope thereof.
aye
15, ****The test procedure was the same as Example VI.
It will be understood by those skilled in the art that many modifications and variations of the present invention may be made without departing from the spirit and the scope thereof.
aye
Claims (30)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS
1. An adhesive composition consisting essentially of (a) a ricinoleate urethane polyol, and (b) a chlorinated polyvinyl chloride appearing in quantities no greater than approximately 90% by weight of the combined polyol and chlorinated polyvinyl chloride.
2. An adhesive composition in accordance with Claim 1 in which (a) the ricinoleate urethane polyol is prepared from reacting an isocyanate having a functionality of at least 2 with a ricinoleate polyol having a functionality of at least 2 at an isocyanate to hydroxyl ratio (NCO/OH) no greater than approximately 0.9/1Ø
3. An adhesive composition in accordance with Claim 1, in which (a) the said composition further includes a composition capable of cross-linking the ricinoleate polyol which is an isocyanate terminated prepolymer.
4. An adhesive composition in accordance with Claim 3 in which (a) the said prepolymer is prepared by reacting a ricin-oleate polyol with isophorone diisocyanate.
5. An adhesive composition in accordance with Claim 3 in which (a) the said prepolymer is prepared by reacting a ricin-oleate polyol with diphenylmethane diisocyanate.
6. An adhesive composition in accordance with Claim 3 in which (a) the said isocyanate terminated prepolymer is prepared by reacting a castor oil with the said isocyanate.
7. An adhesive composition in accordance with Claim 2, in which (a) the ricinoleate urethane polyol is prepared by reacting a ricinoleate polyol with toluene diisocyanate.
8. An adhesive composition in accordance with Claim 3 in which (a) the said prepolymer is an isocyanate terminated ricinoleate prepolymer.
9. An adhesive composition in accordance with Claim 3 in which (a) the said prepolymer is prepared by reacting a ricinoleate polyol with toluene diisocyanate.
10. An adhesive composition in accordance with Claim 3 in which (a) the said prepolymer is prepared by reacting a ricinoleate polyol with methylene-bis (4-cyclohexylisocyanate).
11. An adhesive composition in accordance with Claim 3 in which (a) the said isocyanate terminated prepolymer is prepared from reacting trimethylol propane with an isocyanate.
12. An adhesive composition in accordance with Claim 2 in which (a) the ricinoleate urethane polyol is prepared by reacting a ricinoleate polyol with diphenylmethane diisocyanate.
13. An adhesive composition in accordance with Claim 2 in which 17.
(a) the ricinoleate urethane polyol is prepared by reacting a ricinoleate polyol with methylene-bis (4-cyclohexylisocyanate).
(a) the ricinoleate urethane polyol is prepared by reacting a ricinoleate polyol with methylene-bis (4-cyclohexylisocyanate).
14. An adhesive composition in accordance with Claim 2 in which (a) the ricinoleate urethane polyol is prepared by reacting a ricinoleate polyol with isophorone diisocyanate.
15. An adhesive composition in accordance with Claim 1 in which (a) the chlorinated polyvinyl chloride is prepared by post chlorinating a polyvinyl chloride resin.
16. An adhesive composition in accordance with Claim 2 in which (a) the ricinoleate urethane polyol is prepared by reacting a ricinoleate polyol with toluene diisocyanate.
17. An adhesive composition in accordance with Claim 15 in which (a) the ricinoleate urethane polyol is prepared by reacting a ricinoleate polyol with diphenylmethane diisocyanate.
18. An adhesive composition in accordance with Claim 15 in which (a) the ricinoleate urethane polyol is prepared by reacting a ricinoleate polyol with methylene-bis (4-cyclohexylisocyanate).
19. An adhesive composition in accordance with Claim 15 in which (a) the ricinoleate urethane polyol is prepared by reacting a ricinoleate polyol with isophorone diisocyanate.
20. An adhesive composition in accordance with Claim 1 in which 18.
(a) the ricinoleate urethane polyol is prepared by reacting a ricinoleate polyol with toluene diisocyanate.
(a) the ricinoleate urethane polyol is prepared by reacting a ricinoleate polyol with toluene diisocyanate.
21. An adhesive composition in accordance with Claim 1 in which (a) the ricinoleate urethane polyol is prepared by reacting a ricinoleate polyol with diphenylmethane diisocyanate.
22. An adhesive composition in accordance with Claim 1 in which (a) the ricinoleate urethane polyol is prepared by reacting a ricinoleate polyol with methylene-bis (4-cyclohexylisocyanate).
23. An adhesive composition in accordance with Claim 1 in which (a) the ricinoleate urethane polyol is prepared by reacting a ricinoleate polyol with isophorone diisocyanate.
24. An adhesive composition in accordance with Claim 1 in which (a) the ricinoleate urethane polyol is prepared by reacting an isocyanate having a functionality of at least 2 with castor oil.
25. An adhesive composition in accordance with Claim 24 in which (a) the ricinoleate urethane polyol is prepared from reacting castor oil with diphenylmethane diisocyanate.
26. An adhesive composition in accordance with Claim 24 in which (a) the ricinoleate urethane polyol is prepared from reacting castor oil with toluene diisocyanate.
27. An adhesive composition in accordance with Claim 24 in which 19.
(a) the ricinoleate urethane polyol is prepared from reacting castor oil with isophorone diisocyanate.
(a) the ricinoleate urethane polyol is prepared from reacting castor oil with isophorone diisocyanate.
28. An adhesive composition in accordance with Claim 24 in which (a) the ricinoleate urethane polyol is prepared by reacting methylene-bis (4-cyclohexylisocyanate) with castor oil.
29. An adhesive composition in accordance with Claim 1 which further includes (a) a composition capable of cross-linking the ricinoleate urethane polyol.
30. An adhesive composition in accordance with Claim 29 in which (a) The said composition capable of cross-linking is an isocyanate having a functionality of at least 2.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31712081A | 1981-11-02 | 1981-11-02 | |
| US317,120 | 1981-11-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1215188A true CA1215188A (en) | 1986-12-09 |
Family
ID=23232203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000414638A Expired CA1215188A (en) | 1981-11-02 | 1982-11-01 | Adhesive consisting essentially of a recinoleate urethane polyol and a chlorinated polyvinyl chloride |
Country Status (2)
| Country | Link |
|---|---|
| CA (1) | CA1215188A (en) |
| GB (1) | GB2111512B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2014073A1 (en) * | 1989-04-14 | 1990-10-14 | Usama E. Younes | Flame-retardant polyurethane composition |
| EP2062927B1 (en) * | 2007-11-20 | 2016-06-29 | Henkel AG & Co. KGaA | 2K-PU adhesive for low temperature applications |
-
1982
- 1982-11-01 CA CA000414638A patent/CA1215188A/en not_active Expired
- 1982-11-02 GB GB08231234A patent/GB2111512B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB2111512A (en) | 1983-07-06 |
| GB2111512B (en) | 1985-04-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2986954B2 (en) | Mixtures of polyurethane prepolymers containing isocyanate end groups | |
| US4217254A (en) | High green strength curable urethane adhesive | |
| US6221978B1 (en) | Moisture curable hot melt adhesive and method for bonding substrates using same | |
| US4585819A (en) | Fusion adhesive which can comprise an isocyanate prepolymer, a thermoplastic polymer and/or a lower molecular weight ketone resin | |
| US3879248A (en) | Method of bonding using urethane base pressure sensitive adhesives | |
| CA1313718C (en) | Heat-meltable polymer for use as adhesive agent, method for manufacturing the same and aplication thereof the gluing of substrate materials | |
| EP0232055B1 (en) | Thermally stable hot melt moisture curing polyurethane adhesive composition | |
| DE60211726T2 (en) | HUMIDITY-CURABLE POLYURETHANE MELT ADHESIVE WITH LARGE PORTION RANGE | |
| JPS61185578A (en) | Adhesive composition | |
| US3246049A (en) | Pressure sensitive adhesive comprising an isocyanate cross-linked polyester of castor oil and diglycolic acid, and tape coated with said adhesive | |
| JPH11511774A (en) | Join method | |
| EP2242784A2 (en) | Liquid polyurethane prepolymers useful in solvent-free adhesives | |
| NO159534B (en) | MELTIC AGENTS CONSISTS OF A MIXTURE OF A URETANE PREPARY POLYMER WITH FREE ISOCYANATE GROUPS, A THERMOPLASTIC POLYMER AND A LOW MOLECYLAR SYNTHETIC RESIN. | |
| US4340682A (en) | Adhesive consisting essentially of an isocyanate terminated ricinoleate prepolymer and a chlorinated polyvinyl chloride | |
| JP2650150B2 (en) | Hot melt adhesive composition crosslinkable by moisture | |
| CA2155225A1 (en) | Two-pack aqueous adhesive | |
| CA2052047C (en) | Glass adhesive | |
| US4256615A (en) | Adhesive consisting essentially of a ricinoleate urethane polyol and a chlorinated rubber | |
| US5262481A (en) | Moisture-cross-linkable thermoplastic adhesive compositions, uses thereof, and modified components for use in said adhesive compositions | |
| US5180632A (en) | Orthopedic casting material having reduced tack and reduced slip | |
| US4569972A (en) | Adhesive consisting essentially of a ricinoleate urethane polyol and a chlorinated polyvinyl chloride | |
| CA1215188A (en) | Adhesive consisting essentially of a recinoleate urethane polyol and a chlorinated polyvinyl chloride | |
| EP0979835A1 (en) | Moisture curable pressure sensitive adhesives | |
| NZ226391A (en) | Aqueous polymer composition comprising isocyanate-reactive vinyl polymer and a polyisocyanate | |
| US6025434A (en) | Process for making an adhesive and product thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |