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US3933725A Expired / Lapsed US ⏱️ 0.0 years remaining

Preparation of isocyanate terminated prepolymer

Assignee: Motors Liquidation Co
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Filing: 1974-09-26
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Granted: 1976-01-20
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Expires: 1994-09-26
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Abstract

Abstract In accordance with a preferred embodiment of this invention, a polyether-type, isocyanate-terminated, polyurethane prepolymer is formed by (1) blending about one equivalent of diphenylmethane diisocyanate (hereinafter "MDI") and a mixture of from about 0.5 to about 0.55 equivalent of a polyoxypropylene diol having a molecular weight (Mn) within the range of about 1,000 to about 2,000, from about 0.08 to about 0.13 equivalent of a polyoxypropylene trio, having a molecular weight (Mn) in the range of from about 4,000 to about 4,500, and from about 10 to about 15 parts by weight of a hydrogenated terphenyl plasticizer per 100 parts by weight of the mixture of MDI and the polyols, (2) initiating the polymerization reaction by adding from about 0.08 to about 0.12 parts by weight of a tin catalyst per about 250 parts by weight of MDI; the catalyst being initially dissolved in from about 10 to about 15 parts by weight of additional hydrogenated terphenyl plasticizer per about 100 parts of the mixture of MDI and polyols. This process yields a thermally stable prepolymer, which is suitable for many applications, and the required reaction time may be as low as one minute. This represents a significant improvement over the prior art.

Inventors

  • 👤 Thomas J. Dearlove
  • 👤 Gregory A. Campbell
  • 👤 Richard P. Atkins

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 11:22
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/48; C08G18/4804; C08G18/4812; C08G18/08; C08G18/10; C08G18/12; C08K; C08K5/00; C08K5/01

Claims Analysis

Total Claims: 16
Claim 1
Independent Claim 123 words
An improved process of forming a partially crosslinked, plasticized, polyurethane moisture curable sealant prepolymer having an isocyanate to hydroxyl equivalent ratio in the range of about 1.4:1 to about 1.5:1, a free isocyanate content in the range of about 1.2% to about 1.8% by weight based on the total prepolymer composition, a Brookfield viscosity at 25° C. in the range of about 25,000 to about 100,000 cp., and a molecular weight (Mw) in the range of about 15,000 to about 25,000, comprising: a. stirring together until uniformly blended at a temperature in the range of from about 40° C. to about 100° C.: 1. about 1 equivalent of a diisocyanate selected from the group consisting of toluene diisocyanate and diphenyl methane diisocyanate, 2.
Claim 2
Dependent Claim 123 words
An improved process of forming a partially crosslinked, plasticized, polyurethane moisture curable sealant prepolymer having an isocyanate to hydroxyl equivalent ratio in the range of about 1.4:1 to about 1.5:1, a free isocyanate content in the range of about 1.2% to about 1.8% by weight based on the total prepolymer composition, a Brookfield viscosity at 25° C. in the range of about 25,000 to about 100,000 cp., and a molecular weight (Mw) in the range of about 15,000 to about 25,000, comprising: a. stirring together until uniformly blended at a temperature in the range of from about 40° C. to about 100° C.: 1. about 1 equivalent of a diisocyanate selected from the group consisting of toluene diisocyanate and diphenyl methane diisocyanate, 2.
Claim 3
Dependent Claim 203 words
about 0.50 to about 0.55 equivalent of a dihydroxy terminated polyoxypropylene, having a molecular weight (Mn) in the range of about 1,000 to about 2,000, 3. about 0.08 to about 0.13 equivalent of a polypropylene ether triol, having a molecular weight (Mn) in the range of from about 1,500 to about 4,500, and 4. about 5% to 15% by weight based on the total composition of a plasticizer that is miscible and compatible with said diisocyanate and said polyols, until a solution is achieved, and then as said solution is being stirred, b. catalyzing the polymerization reaction of said diisocyanate and said polyols to form said prepolymer by mixing into said solution a solution comprising from about 0.08 to about 0.12 weight parts per each 250 weight parts of said diisocyanate of a tin-based urethane polymerization catalyst dissolved in about 5% to about 10% by weight based on the total composition of additional plasticizer, and c. continuing to stir said reacting mixture for a period of minutes to maintain a relatively uniform distribution of reacting species until the free isocyanate content of said solution is within the range of from about 1.2% to about 1.8% by weight based on the total composition, thereby
Claim 4
Dependent Claim 203 words
about 0.50 to about 0.55 equivalent of a dihydroxy terminated polyoxypropylene, having a molecular weight (Mn) in the range of about 1,000 to about 2,000, 3. about 0.08 to about 0.13 equivalent of a polypropylene ether triol, having a molecular weight (Mn) in the range of from about 1,500 to about 4,500, and 4. about 5% to 15% by weight based on the total composition of a plasticizer that is miscible and compatible with said diisocyanate and said polyols, until a solution is achieved, and then as said solution is being stirred, b. catalyzing the polymerization reaction of said diisocyanate and said polyols to form said prepolymer by mixing into said solution a solution comprising from about 0.08 to about 0.12 weight parts per each 250 weight parts of said diisocyanate of a tin-based urethane polymerization catalyst dissolved in about 5% to about 10% by weight based on the total composition of additional plasticizer, and c. continuing to stir said reacting mixture for a period of minutes to maintain a relatively uniform distribution of reacting species until the free isocyanate content of said solution is within the range of from about 1.2% to about 1.8% by weight based on the total composition, thereby
Claim 5
Dependent Claim 311 words
forming said prepolymer substantially free of gel particles. 2. An improved process of forming a partially crosslinked, plasticized, polyurethane moisture curable sealant prepolymer having an isocyanate to hydroxyl equivalent ratio in the range of about 1.4:1 to about 1.5:1, a free isocyanate content in the range of about 1.2% to about 1.8% by weight based on the total prepolymer composition, a Brookfield viscosity at 25° C. in the range of about 25,000 to about 50,000 cp., and a molecular weight (Mw) in the range of about 15,000 to about 25,000, comprising: a. stirring together until uniformly blended at a temperature in the range of from about 40° C. to about 100° C.: 1. about 250 weight parts of diphenyl methane diisocyanate, 2. about 1,000 to about 1,100 weight parts of a dihydroxy terminated polyoxypropylene, having a molecular weight (Mn) in the range of about 1,000 to about 2,000, 3. about 220 to about 350 weight parts of a polypropylene ether triol, having a molecular weight (Mn) in the range of from about 4,000 to about 4,500, and 4. about 190 to about 210 parts of a hydrogenated terphenyl plasticizer until a solution is achieved, and then as said solution is being stirred, b. catalyzing the polymerization reaction of said diisocyanate and said polyols to form said prepolymer by mixing into said solution a solution comprising from about 0.08 to about 0.12 weight parts of a tin urethane polymerization catalyst dissolved in about 190 to about 210 weight parts of a hydrogenated terphenyl plasticizer, and c. continuing to stir said reacting mixture for a period of minutes to maintain a relatively uniform distribution of reacting species until the free isocyanate content of said solution is within the range of from about 1.2% to about 1.8% by weight based on the total composition, thereby forming said sealant prepolymer substantially free of gel particles.
Claim 6
Dependent Claim 311 words
forming said prepolymer substantially free of gel particles. 2. An improved process of forming a partially crosslinked, plasticized, polyurethane moisture curable sealant prepolymer having an isocyanate to hydroxyl equivalent ratio in the range of about 1.4:1 to about 1.5:1, a free isocyanate content in the range of about 1.2% to about 1.8% by weight based on the total prepolymer composition, a Brookfield viscosity at 25° C. in the range of about 25,000 to about 50,000 cp., and a molecular weight (Mw) in the range of about 15,000 to about 25,000, comprising: a. stirring together until uniformly blended at a temperature in the range of from about 40° C. to about 100° C.: 1. about 250 weight parts of diphenyl methane diisocyanate, 2. about 1,000 to about 1,100 weight parts of a dihydroxy terminated polyoxypropylene, having a molecular weight (Mn) in the range of about 1,000 to about 2,000, 3. about 220 to about 350 weight parts of a polypropylene ether triol, having a molecular weight (Mn) in the range of from about 4,000 to about 4,500, and 4. about 190 to about 210 parts of a hydrogenated terphenyl plasticizer until a solution is achieved, and then as said solution is being stirred, b. catalyzing the polymerization reaction of said diisocyanate and said polyols to form said prepolymer by mixing into said solution a solution comprising from about 0.08 to about 0.12 weight parts of a tin urethane polymerization catalyst dissolved in about 190 to about 210 weight parts of a hydrogenated terphenyl plasticizer, and c. continuing to stir said reacting mixture for a period of minutes to maintain a relatively uniform distribution of reacting species until the free isocyanate content of said solution is within the range of from about 1.2% to about 1.8% by weight based on the total composition, thereby forming said sealant prepolymer substantially free of gel particles.
Claim 7
Dependent Claim 144 words
An improved process of forming a partially crosslinked, externally plasticized, polyether-type polyurethane prepolymer which is substantially gel free having an isocyanate to hydroxyl equivalent ratio in the range of about 1.15 to about 1.8, a free isocyanate content in the range of about 0.5% to about 10% by weight based on the total prepolymer composition, a viscosity in the range of about 15,000 to about 500,000 cp., and a molecular weight (Mw) in the range of about 10,000 to about 40,000, said prepolymer being curable by atmospheric humidity, comprising: a. uniformly blending at a temperature within the range of from about 40° C. to about 100° C.: 1. about 250 weight parts of diphenyl methane diisocyanate, 2. about 730 to about 1,200 weight parts of a dihydroxy terminated polyoxypropylene diol, having a molecular weight (Mn) in the range of about 200 to about 2,200,
Claim 8
Dependent Claim 144 words
An improved process of forming a partially crosslinked, externally plasticized, polyether-type polyurethane prepolymer which is substantially gel free having an isocyanate to hydroxyl equivalent ratio in the range of about 1.15 to about 1.8, a free isocyanate content in the range of about 0.5% to about 10% by weight based on the total prepolymer composition, a viscosity in the range of about 15,000 to about 500,000 cp., and a molecular weight (Mw) in the range of about 10,000 to about 40,000, said prepolymer being curable by atmospheric humidity, comprising: a. uniformly blending at a temperature within the range of from about 40° C. to about 100° C.: 1. about 250 weight parts of diphenyl methane diisocyanate, 2. about 730 to about 1,200 weight parts of a dihydroxy terminated polyoxypropylene diol, having a molecular weight (Mn) in the range of about 200 to about 2,200,
Claim 9
Dependent Claim 162 words
about 140 to about 730 weight parts of a polypropylene ether triol, having a molecular weight (Mn) in the range of from about 700 to about 4,500, and 4. about 5% to about 15% by weight based on the total composition of a plasticizer which is miscible and compatible with said diisocyanate and said polyols until a solution is achieved, and then as said solution is being stirred, b. catalyzing the polymerization reaction of said diisocyanate and said polyols to form said prepolymer by mixing into said dispersion a solution comprising from about 0.1 to about 0.4 weight parts of a tin catalyst and from about 5% to about 15% by weight based on the total composition weight parts of additional plasticizer, and c. stirring said reacting mixture to maintain a relatively uniform distribution of reacting species until the free isocyanate content of said mixture is within the range of from about 0.5% to 10% by weight based on the total composition.
Claim 10
Dependent Claim 162 words
about 140 to about 730 weight parts of a polypropylene ether triol, having a molecular weight (Mn) in the range of from about 700 to about 4,500, and 4. about 5% to about 15% by weight based on the total composition of a plasticizer which is miscible and compatible with said diisocyanate and said polyols until a solution is achieved, and then as said solution is being stirred, b. catalyzing the polymerization reaction of said diisocyanate and said polyols to form said prepolymer by mixing into said dispersion a solution comprising from about 0.1 to about 0.4 weight parts of a tin catalyst and from about 5% to about 15% by weight based on the total composition weight parts of additional plasticizer, and c. stirring said reacting mixture to maintain a relatively uniform distribution of reacting species until the free isocyanate content of said mixture is within the range of from about 0.5% to 10% by weight based on the total composition.
Claim 11
Dependent Claim 91 words
An improved process of forming a partially crosslinked, plasticized, polyurethane moisture curable sealant prepolymer having an isocyanate to hydroxyl equivalent ratio in the range of about 1.4:1 to about 1.5:1, a free isocyanate content in the range of about 1.2% to about 1.8% by weight based on the total prepolymer composition, a Brookfield viscosity at 25° C. in the range of about 8,000 to about 40,000 cp., and a molecular weight (Mw) in the range of about 14,000 to about 22,000, comprising: a. stirring together until uniformly blended at room temperature:
Claim 12
Dependent Claim 91 words
An improved process of forming a partially crosslinked, plasticized, polyurethane moisture curable sealant prepolymer having an isocyanate to hydroxyl equivalent ratio in the range of about 1.4:1 to about 1.5:1, a free isocyanate content in the range of about 1.2% to about 1.8% by weight based on the total prepolymer composition, a Brookfield viscosity at 25° C. in the range of about 8,000 to about 40,000 cp., and a molecular weight (Mw) in the range of about 14,000 to about 22,000, comprising: a. stirring together until uniformly blended at room temperature:
Claim 13
Dependent Claim 197 words
about 250 weight parts of toluene diisocyanate, 2. about 1,000 to about 1,100 weight parts of a dihydroxy terminated polyoxypropylene, having a molecular weight (Mn) in the range of about 1,000 to about 2,000, 3. about 220 to about 350 weight parts of a polypropylene ether triol, having a molecular weight (Mn) in the range of from about 4,000 to about 4,500, and 4. about 190 to about 210 parts of a hydrogenated terphenyl plasticizer until a solution is achieved, and then as said solution is being stirred, b. catalyzing the polymerization reaction of said toluene diisocyanate and said polyols to form said prepolymer by mixing into said solution a solution comprising from about 0.08 to about 0.12 weight parts of a tin-based, urethane-polymerization catalyst dissolved in about 190 to about 210 weight parts of a hydrogenated terphenyl plasticizer, and c. continuing to stir said reacting mixture for a period of minutes to maintain a relatively uniform distribution of reacting species until the free isocyanate content of said solution is within the range of from about 1.2% to about 1.8% by weight based on the total composition, thereby forming said sealant prepolymer substantially free of gel particles.
Claim 14
Dependent Claim 197 words
about 250 weight parts of toluene diisocyanate, 2. about 1,000 to about 1,100 weight parts of a dihydroxy terminated polyoxypropylene, having a molecular weight (Mn) in the range of about 1,000 to about 2,000, 3. about 220 to about 350 weight parts of a polypropylene ether triol, having a molecular weight (Mn) in the range of from about 4,000 to about 4,500, and 4. about 190 to about 210 parts of a hydrogenated terphenyl plasticizer until a solution is achieved, and then as said solution is being stirred, b. catalyzing the polymerization reaction of said toluene diisocyanate and said polyols to form said prepolymer by mixing into said solution a solution comprising from about 0.08 to about 0.12 weight parts of a tin-based, urethane-polymerization catalyst dissolved in about 190 to about 210 weight parts of a hydrogenated terphenyl plasticizer, and c. continuing to stir said reacting mixture for a period of minutes to maintain a relatively uniform distribution of reacting species until the free isocyanate content of said solution is within the range of from about 1.2% to about 1.8% by weight based on the total composition, thereby forming said sealant prepolymer substantially free of gel particles.
Claim 15
Dependent Claim 324 words
An improved process of forming a partially crosslinked, plasticized, polyurethane moisture curable sealant prepolymer having an isocyanate to hydroxyl equivalent ratio in the range of about 1.15:1 to about 1.8:1, a free isocyanate content in the range of about 0.5% to about 10% by weight based on the total prepolymer composition, a Brookfield viscosity at 25° C. in the range of about 8,000 to about 500,000 cp., and a molecular weight (Mw) in the range of about 8,000 to about 40,000, comprising: a. stirring together until uniformly blended at a temperature in the range of from about 40° C. to about 80° C.: 1. about 1.0 equivalent of toluene diisocyanate, 2. about 0.37 to about 0.6 equivalent of a dihydroxy terminated polyoxypropylene, having a molecular weight (Mn) in the range of about 1,000 to about 2,000, 3. about 0.05 to about 0.27 equivalent of a polypropylene ether triol, having a molecular weight (Mn) in the range of from about 700 to about 4,500, and 4. about 5% to about 15% by weight based on the total composition of a plasticizer which is miscible and compatible with said diisocyanate and said polyols until a solution is achieved, and then as said solution is being stirred, b. catalyzing the polymerization reaction of said toluene diisocyanate and said polyols to form said prepolymer by mixing into said solution a solution comprising from about 0.05 to about 0.4 weight parts per 250 weight parts of diisocyanate of a tin-based, urethane polymerization catalyst dissolved in about 5% to about 15% by weight based on the total composition parts of additional plasticizer, and c. continuing to stir said reacting mixture for a period of minutes to maintain a relatively uniform distribution of reacting species until the free isocyanate content of said solution is within the range of from about 0.5% to about 10% by weight based on the total composition, thereby forming said sealant prepolymer substantially free of gel particles.
Claim 16
Dependent Claim 324 words
An improved process of forming a partially crosslinked, plasticized, polyurethane moisture curable sealant prepolymer having an isocyanate to hydroxyl equivalent ratio in the range of about 1.15:1 to about 1.8:1, a free isocyanate content in the range of about 0.5% to about 10% by weight based on the total prepolymer composition, a Brookfield viscosity at 25° C. in the range of about 8,000 to about 500,000 cp., and a molecular weight (Mw) in the range of about 8,000 to about 40,000, comprising: a. stirring together until uniformly blended at a temperature in the range of from about 40° C. to about 80° C.: 1. about 1.0 equivalent of toluene diisocyanate, 2. about 0.37 to about 0.6 equivalent of a dihydroxy terminated polyoxypropylene, having a molecular weight (Mn) in the range of about 1,000 to about 2,000, 3. about 0.05 to about 0.27 equivalent of a polypropylene ether triol, having a molecular weight (Mn) in the range of from about 700 to about 4,500, and 4. about 5% to about 15% by weight based on the total composition of a plasticizer which is miscible and compatible with said diisocyanate and said polyols until a solution is achieved, and then as said solution is being stirred, b. catalyzing the polymerization reaction of said toluene diisocyanate and said polyols to form said prepolymer by mixing into said solution a solution comprising from about 0.05 to about 0.4 weight parts per 250 weight parts of diisocyanate of a tin-based, urethane polymerization catalyst dissolved in about 5% to about 15% by weight based on the total composition parts of additional plasticizer, and c. continuing to stir said reacting mixture for a period of minutes to maintain a relatively uniform distribution of reacting species until the free isocyanate content of said solution is within the range of from about 0.5% to about 10% by weight based on the total composition, thereby forming said sealant prepolymer substantially free of gel particles.

References Cited (Backward Citations)

GB1242866A Cited
US3707521A Cited
US3779794A Cited
US3711445A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-01-19 1979-07-21 1980-01-20 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-01-19 1983-07-21 1984-01-20 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-01-19 1987-07-21 1988-01-20 $7700.00 Window Closed / Lapsed

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