US4413111A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Isocyanate-terminated prepolymers with low free monomer contents
Assignee: Bayer Corp
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Filing: 1982-09-29
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Granted: 1983-11-01
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Expires: 2002-09-29
Abstract
Abstract The present invention is directed to a process for the preparation of an isocyanate-terminated prepolymer having a content of unreacted diisocyanate of less than about 2% by weight, preferably less than about 1% by weight, based on the weight of the isocyanate-terminated prepolymer, and containing internal urethane groups based on 4,4'-diisocyanato-dicyclohexyl-methane by (a) preparing an OH-terminated prepolymer from (i) a high molecular weight polyol component, and/or (ii) a low molecular weight isocyanate-reactive component, and (iii) a polyisocyanate component comprising 4,4'-diisocyanato-dicyclohexyl-methane at an NCO/OH equivalent ratio of about 0.5:1 to 0.9:1; (b) forming the isocyanate-terminated prepolymer by reacting the OH-terminated prepolymer with a polyisocyanate other than 4,4'-diisocyanato-dicyclohexyl-methane containing aromatically-, aliphatically- and/or cycloaliphatically-bound isocyanate groups at an NCO:OH equivalent ratio, based on the free -OH groups of component (a), of about 1.6:1 to 15:1, and (c) reducing the amount of unreacted diisocyanate to less than about 2% by weight, based on the weight of the isocyanate-terminated prepolymer. The present invention is also directed to the products prepared by this process and their use in one-component, moisture-cure systems or as the isocyanate component in two-component polyurethanes.
Inventors
- 👤 Peter H. Markusch
- 👤 Terry A. Potter
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 02:23
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/74; C08G18/75; C08G18/758; C08G18/08; C08G18/10
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
142 words
A process for the preparation of an isocyanate-terminated prepolymer having a content of unreacted diisocyanate of less than 2% by weight, based on the weight of said isocyanate-terminated prepolymer, and containing internal urethane groups based on 4,4'-diisocyanato-dicyclohexyl-methane which comprises (a) preparing an OH-terminated prepolymer from (i) a high molecular weight polyol component, and/or (ii) a low molecular weight isocyanate-reactive component, and (iii) a polyisocyanate component comprising 4,4'-diisocyanate-dicyclohexyl-methane at an NCO/OH equivalent ratio of about 0.5:1 to 0.9:1; (b) forming said isocyanate-terminated prepolymer by reacting said OH-terminated prepolymer with a polyisocyanate other than 4,4'-diisocyanato-dicyclohexyl-methane containing aromatically-, aliphatically- and/or cycloaliphatically-bound isocyanate groups at an NCO:OH equivalent ratio, based on the free --OH groups of component (a), of about 1.6:1 to 15:1; and (c) reducing the amount of unreacted diisocyanate to less than about 2% by weight, based on the weight of said isocyanate-terminated prepolymer.
Claim 2
Dependent Claim
142 words
A process for the preparation of an isocyanate-terminated prepolymer having a content of unreacted diisocyanate of less than 2% by weight, based on the weight of said isocyanate-terminated prepolymer, and containing internal urethane groups based on 4,4'-diisocyanato-dicyclohexyl-methane which comprises (a) preparing an OH-terminated prepolymer from (i) a high molecular weight polyol component, and/or (ii) a low molecular weight isocyanate-reactive component, and (iii) a polyisocyanate component comprising 4,4'-diisocyanate-dicyclohexyl-methane at an NCO/OH equivalent ratio of about 0.5:1 to 0.9:1; (b) forming said isocyanate-terminated prepolymer by reacting said OH-terminated prepolymer with a polyisocyanate other than 4,4'-diisocyanato-dicyclohexyl-methane containing aromatically-, aliphatically- and/or cycloaliphatically-bound isocyanate groups at an NCO:OH equivalent ratio, based on the free --OH groups of component (a), of about 1.6:1 to 15:1; and (c) reducing the amount of unreacted diisocyanate to less than about 2% by weight, based on the weight of said isocyanate-terminated prepolymer.
Claim 3
Dependent Claim
22 words
The process of claim 1 wherein said high molecular weight polyol component has an average hydroxyl functionality of about 2 to 4.
Claim 4
Dependent Claim
21 words
The process of claim 1 wherein said low molecular weight isocyanate-reactive component has an average functionality of about 2 to 4.
Claim 5
Dependent Claim
36 words
The process of claim 1 wherein component (b) comprises a member selected from the group consisting of isophorone diisocyanate, 1,6-hexamethylene diisocyanate, biuret group-containing polyisocyanates based on 1,6-hexamethylene diisocyanate and isocyanurate group-containing polyisocyanates based on 1,6-hexamethylene diisocyanate.
Claim 6
Dependent Claim
19 words
The process of claim 1 wherein said OH-terminated prepolymer has an average molecular weight based about 380 and 10,000.
Claim 7
Dependent Claim
19 words
The process of claim 1 wherein said isocyanate-terminated prepolymer has an average molecular weight between about 600 and 11,000.
Claim 8
Dependent Claim
32 words
The process of claim 1 wherein said isocyanate-terminated prepolymer contains about 33 to 85 mole percent of 4,4'-diisocyanate-dicyclohexyl-methane based on the total number of moles of polyisocyanate contained in said isocyanate-terminated prepolymer.
Claim 9
Dependent Claim
180 words
A process for the preparation of an isocyanate-terminated prepolymer having an average molecular weight of between about 600 and 11,000 and a content of unreacted diisocyanate of less than about 2% by weight, based on the weight of said isocyanate-terminated prepolymer, and containing internal urethane groups based on 4,4'-diisocyanato-dicyclohexyl-methane which comprises (a) preparing an OH-terminated prepolymer having an average molecular weight between about 380 and 10,000 from (i) a high molecular weight polyol component having an average hydroxyl functionality of about 2 to 4, and/or (ii) a low molecular weight isocyanate-reactive component having an average functionality of about 2 to 4, and (iii) a polyisocyanate component comprising 4,4'-diisocyanato-dicyclohexyl-methane at an NCO/OH equivalent ratio of about 0.5:1 to 0.9:1; (b) forming said isocyanate-terminated prepolymer by reacting said OH-terminated prepolymer with a polyisocyanate containing aromatically-, aliphatically- and/or cycloaliphatically-bound isocyanate groups at an NCO:OH equivalent ratio, based on the free --OH groups of component (a), of about 1.6:1 to 15:1; and (c) reducing the amount of unreacted diisocyanate to less than about 2% by weight, based on the weight of said isocyanate-terminated prepolymer.
Claim 10
Dependent Claim
180 words
A process for the preparation of an isocyanate-terminated prepolymer having an average molecular weight of between about 600 and 11,000 and a content of unreacted diisocyanate of less than about 2% by weight, based on the weight of said isocyanate-terminated prepolymer, and containing internal urethane groups based on 4,4'-diisocyanato-dicyclohexyl-methane which comprises (a) preparing an OH-terminated prepolymer having an average molecular weight between about 380 and 10,000 from (i) a high molecular weight polyol component having an average hydroxyl functionality of about 2 to 4, and/or (ii) a low molecular weight isocyanate-reactive component having an average functionality of about 2 to 4, and (iii) a polyisocyanate component comprising 4,4'-diisocyanato-dicyclohexyl-methane at an NCO/OH equivalent ratio of about 0.5:1 to 0.9:1; (b) forming said isocyanate-terminated prepolymer by reacting said OH-terminated prepolymer with a polyisocyanate containing aromatically-, aliphatically- and/or cycloaliphatically-bound isocyanate groups at an NCO:OH equivalent ratio, based on the free --OH groups of component (a), of about 1.6:1 to 15:1; and (c) reducing the amount of unreacted diisocyanate to less than about 2% by weight, based on the weight of said isocyanate-terminated prepolymer.
Claim 11
Dependent Claim
32 words
The process of claim 8 wherein said isocyanate-terminated prepolymer contains about 33 to 85 mole percent of 4,4'-diisocyanato-dicyclohexyl-methane based on the total number of moles of polyisocyanate contained in said isocyanate-terminated prepolymer.
Claim 12
Dependent Claim
36 words
The process of claim 9 wherein component (b) comprises a member selected from the group consisting of isophorone diisocyanate, 1,6-hexamethylene diisocyanate, biuret group-containing polyisocyanates based on 1,6-hexamethylene diisocyanate and isocyanurate group-containing polyisocyanates based on 1,6-hexamethylene diisocyanate.
Claim 13
Dependent Claim
11 words
The product produced in accordance with claim 1, 8 or 9.
Claim 14
Dependent Claim
10 words
A one-component, moisture-cure system comprising the product of claim 11.
Claim 15
Dependent Claim
17 words
A two-component polyurethane composition which comprises (a) the product of claim 11 and (b) an isocyanate-reactive comonent.
Claim 16
Dependent Claim
11 words
The composition of claim 13 wherein component (b) is a polyol.
References Cited (Backward Citations)
US4195009A
Cited
US4184005A
Cited
US4292350A
Cited
US4211804A
Cited
US4254168A
Cited
US4282123A
Cited
US4247675A
Cited
US4273912A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-10-31 | 1987-05-02 | 1987-11-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-10-31 | 1991-05-02 | 1991-11-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-10-31 | 1995-05-02 | 1995-11-01 | $7700.00 | Window Closed / Lapsed |