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US4521582A Expired / Lapsed US ⏱️ 0.0 years remaining

Thermoplastic polyurethanes having a high heat stability, based on naphthylene diisocyanate, their production and their use

Assignee: Bayer AG
•
Filing: 1984-08-02
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Granted: 1985-06-04
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Expires: 2004-08-02
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Abstract

Abstract This invention relates to novel, thermoplastically processible, branched polyurethanes based on naphthylene-1,5-diisocyanate which have good heat stability and are obtained by the claimed process. In the first stage of the process long-chain polyols are reacted with a first diisocyanate which is any diisocyanate other than naphthylene-1,5-diisocyanate in substoichiometric NCO quantities to produce an OH prepolymer which is then lengthened with excess napthylene-1,5-diisocyanate and with a chain lengthening mixture of short-chain diols and triols and/or polyols in specific ratios. The resulting semi-rigid, thermoplastic polyurethane elastomers are characterized by their good dimensional stability under heat, a good rebound elasticity (even at relatively high temperatures), acceptable low temperature flexibility and an outstanding resistance to wear which properties render them useful for the production of hydraulic seals, seals, rollers, buffers, tubes, bellows, plugs, cylinders, couplings and similar moldings.

Inventors

  • 👤 Wilhelm Goyert
  • 👤 Jurgen Winkler

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 18:49
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/70; C08G18/72; C08G18/74; C08G18/76; C08G18/7657; C08G18/7678; C08G18/08; C08G18/10

Claims Analysis

Total Claims: 23
Claim 1
Independent Claim 203 words
A process for the preparation of a thermoplastically processible polyurethane elastomer comprising (i) reacting at least one substantially linear polyhydroxyl compound having a molecular weight of from about 550 to about 10,000 with a substoichiometric amount of at least one first diisocyanate to obtain an OH-prepolymer, and (ii) reacting said OH-prepolymer with a naphthylene-1,5-diisocyanate and a chain lengthener mixture, said first diisocyanate being any diisocyanate other than naphthylene-1,5-diisocyanate, said chain lengthener mixture being comprised of diols and polyols having molecular weights of from 62 to 500, said chain lengthener mixture being characterized in that between about 70 and about 92 equivalent percent of its OH groups are derived from said diols and in that between about 30 and about 8 equivalent percent of its OH groups are derived from polyols having a functionality of three and/or higher than three, said diols are being selected from the group consisting of hydroquinone-di-(β-hydroxyethylether), butane diol-1,4 and hexane diol-1,6, with the proviso that in mixtures containing either butane diol-1,4 or hexane diol-1,6 such mixtures contain co-diols which provide from about 15 to about 50 equivalent percent of said OH groups which are derived from diols only, said co-diols having a molecular weight of from 62 to 500.
Claim 2
Dependent Claim 203 words
A process for the preparation of a thermoplastically processible polyurethane elastomer comprising (i) reacting at least one substantially linear polyhydroxyl compound having a molecular weight of from about 550 to about 10,000 with a substoichiometric amount of at least one first diisocyanate to obtain an OH-prepolymer, and (ii) reacting said OH-prepolymer with a naphthylene-1,5-diisocyanate and a chain lengthener mixture, said first diisocyanate being any diisocyanate other than naphthylene-1,5-diisocyanate, said chain lengthener mixture being comprised of diols and polyols having molecular weights of from 62 to 500, said chain lengthener mixture being characterized in that between about 70 and about 92 equivalent percent of its OH groups are derived from said diols and in that between about 30 and about 8 equivalent percent of its OH groups are derived from polyols having a functionality of three and/or higher than three, said diols are being selected from the group consisting of hydroquinone-di-(β-hydroxyethylether), butane diol-1,4 and hexane diol-1,6, with the proviso that in mixtures containing either butane diol-1,4 or hexane diol-1,6 such mixtures contain co-diols which provide from about 15 to about 50 equivalent percent of said OH groups which are derived from diols only, said co-diols having a molecular weight of from 62 to 500.
Claim 3
Dependent Claim 34 words
The process o f claim 1 wherein at least one member selected from the group consisting of antioxidants, UV absorbers, light protection agents, hydrolysis protection agents, mold release waxes, fillers and dyes is added.
Claim 4
Dependent Claim 27 words
The process of claim 1 wherein said first diisocyanate is a member selected from the group consisting of diphenylmethane diisocyanate, toluylene diisocyanate, dicyclohexylmethane diisocyanate and hexane diisocyanate.
Claim 5
Dependent Claim 25 words
The process of claim 1 wherein said OH prepolymer is characterized in that the ratio of OH:NCO thereof is from about 4:1 to about 1.33:1.
Claim 6
Dependent Claim 22 words
The process of claim 1 wherein said chain lengthener mixture comprises diols and polyols having molecular weights of from 62 to 254.
Claim 7
Dependent Claim 31 words
The process of claim 1 wherein said chain lengthener mixture is characterized in that between about 75 and about 90 equivalent percent of its OH groups are derived from said diols.
Claim 8
Dependent Claim 14 words
The process of claim 1 wherein said co-diols are straight or branched chain diols.
Claim 9
Dependent Claim 22 words
The process of claim 1 wherein said co-diols contain ether or ester groups having a molecular weight of from 62 to 254.
Claim 10
Dependent Claim 37 words
The process of claim 1 wherein said (i) is characterized in that said first diisocyanate is diphenylmethane-4,4'-diisocyanate and in that said polyhydroxyl compounds are reacted therewith in an OH:NCO ratio of from about 3:1 to about 1.5:1.
Claim 11
Dependent Claim 14 words
The process of claim 2 wherein said ratio is about 2.5:1 to about 1.75:1.
Claim 12
Dependent Claim 56 words
The process of claim 1 wherein said chain lengthener mixture is characterized in that between about 75 and about 90 equivalent percent of its OH groups are derived from said diols and about 25 to about 10 equivalent percent of its OH groups are derived from polyols having a functionality of three and/or higher than three.
Claim 13
Dependent Claim 15 words
The process of claim 4 wherein said ratio is from about 3:1 to about 1.5:1.
Claim 14
Dependent Claim 15 words
The process of claim 4 wherein said ratio is from about 2.5:1 to about 1.75:1.
Claim 15
Dependent Claim 34 words
The process of claim 1 further characterized in that said OH prepolymer is reacted with a sufficient amount of naphthylene-1,5-diisocyanate to produce an NCO-prepolymer containing from 4 to 12 percent by weight of NCO.
Claim 16
Dependent Claim 20 words
The process of claim 14 wherein said NCO-prepolymer contains from about 5 to about 10 percent by weight of NCO.
Claim 17
Dependent Claim 10 words
The process of claim 1 wherein said co-diols are aliphatic.
Claim 18
Dependent Claim 26 words
The process of claim 16 wherein said co-diol is selected from the group consisting of butane diol-1,4, hexane diol-1,6, ethane diol, diethylene glycol and neopentyl glycol.
Claim 19
Dependent Claim 49 words
The process of claim 1 wherein said chain lengthener mixture is characterized in that 75 to 90 equivalent percent of its OH groups are derived from a mixture of butane diol-1,4 and hexane diol-1,6 and in that 25 to 10 equivalent percent of OH groups are derived from triols.
Claim 20
Dependent Claim 43 words
The process of claim 1 wherein said chain lengthener mixture is characterized in that 75 to 90 equivalent percent of its OH groups are derived from hydroquinone-di-(β-hydroxyethylether) and in that 25 to 10 equivalent percent of its OH groups are derived from triols.
Claim 21
Dependent Claim 11 words
The process of claim 1 wherein said polyol is trimethylol propane.
Claim 22
Dependent Claim 14 words
A thermoplastically processable polyurethane elastomer produced in accordance with the process of claim 1.
Claim 23
Dependent Claim 10 words
Injection molded articles comprising the polyurethane elastomer of claim 20.

References Cited (Backward Citations)

US2879233A Cited
US3769265A Cited
US3875118A Cited
US3963656A Cited
US4330656A Cited
DE3028501A1 Cited
US4413111A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1988-06-03 1988-12-03 1989-06-04 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-06-03 1992-12-03 1993-06-04 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-06-03 1996-12-03 1997-06-04 $7700.00 Window Closed / Lapsed

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