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US4824888A Expired / Lapsed US ⏱️ 0.0 years remaining

Diurethanes as stabilizing additives in sealing compounds

Assignee: Henkel AG and Co KGaA
•
Filing: 1988-05-03
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Granted: 1989-04-25
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Expires: 2008-05-03
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Abstract

Abstract Diurethanes corresponding to general formula (I) or (II) below R.sup.1 --NH--CO--O--R.sup.2 --O--CO--NH--R.sup.1 (I) R.sup.3 --O--CO--NH--R.sup.4 --NH--CO--OR.sup.3 (II) in which R 1 is a C 3 -C 22 alkyl or aralkyl radical or a phenyl radical, R 2 is a residue of a difunctional polypropylene glycol having a number average molecular weight of from 1000 to 4000, R 3 is the residue of a monofunctional polypropylene glycol monoalkyl ether having a number average molecular weight of from 500 to 2000, and R 4 is C 4 -C 36 alkylene group, a diaryl methane group or a tolylidene group, as stabilizing agents for sealing compositions, for isocyanate-terminated polyurethane prepolymers, and for polyvinyl chlorides and copolymers of vinyl chloride.

Inventors

  • 👤 Winfried Emmerling
  • 👤 Tore Podola
  • 👤 Juergen Wichelhaus

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 17:46
CPC Classifications
C; C09; C09K; C09K3/00; C09K3/10; C09K3/1006; C09K3/1021; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/089; C08G18/10; C08L; C08L75/00; C08L75/04; C08G2190/00; C09K2200/00; C09K2200/06; C09K2200/0615; C09K2200/0622; C09K2200/0625; C09K2200/0635; C09K2200/0645; C09K2200/0657; C09K2200/0662

Claims Analysis

Total Claims: 18
Claim 1
Independent Claim 127 words
In a sealing composition based on an isocyanate-terminated polyurethane prepolymer, the improvement wherein a viscosity stabilizing quantity of at least one diurethane of one or both of the following formulae is present therein: R.sup.1 --NH--CO--O--R.sup.2 --O--CO--NH--R.sup.1 (I) R.sup.3 --O--CO--NH--R.sup.4 --NH--CO--OR.sup.3 (II) in which R 1 is a C 3 -C 22 alkyl, C 7 -C 22 aralkyl, or phenyl radical, R 2 is the residue of a difunctional polypropylene glycol having a number average molecular weight of from about 1000 to about 4000, R 3 is the residue of a monofunctional polypropylene glycol monoalkyl ether having a number average molecular weight of from about 500 to about 2000, and R 4 is a C 4 -C 36 alkylene group, a diaryl methane group, or a tolylidene group.
Claim 2
Dependent Claim 127 words
In a sealing composition based on an isocyanate-terminated polyurethane prepolymer, the improvement wherein a viscosity stabilizing quantity of at least one diurethane of one or both of the following formulae is present therein: R.sup.1 --NH--CO--O--R.sup.2 --O--CO--NH--R.sup.1 (I) R.sup.3 --O--CO--NH--R.sup.4 --NH--CO--OR.sup.3 (II) in which R 1 is a C 3 -C 22 alkyl, C 7 -C 22 aralkyl, or phenyl radical, R 2 is the residue of a difunctional polypropylene glycol having a number average molecular weight of from about 1000 to about 4000, R 3 is the residue of a monofunctional polypropylene glycol monoalkyl ether having a number average molecular weight of from about 500 to about 2000, and R 4 is a C 4 -C 36 alkylene group, a diaryl methane group, or a tolylidene group.
Claim 3
Dependent Claim 30 words
The composition of claim 1 wherein R 1 is a phenylalkyl radical having from 7 to 22 carbon atoms, or an alkylphenylalkyl radical having from 8 to 22 carbon atoms.
Claim 4
Dependent Claim 10 words
The composition of claim 1 wherein R 4 is diphenylmethane.
Claim 5
Dependent Claim 177 words
A sealing composition comprising (a) from about 20 to about 50 parts by weight of at least one isocyanate-terminated polyurethane prepolymer, (b) from about 20 to about 40 parts by weight of a swellable polyvinylchloride or a swellable copolymer of vinyl chloride in powder form, (c) from about 20 to about 40 parts by weight of at least one plasticizer, and (d) from about 50 to about 150% by weight, based on component (a), of at least one diurethane of the following formulae: R.sup.1 --NH--CO--O--R.sup.2 --O--CO--NH--R.sup.1 (I) R.sup.3 --O--CO--NH--R.sup.4 --NH--CO--OR.sup.3 (II) in which R 1 is a C 3 -C 22 alkyl, C 7 -C 22 aralkyl, or phenyl radical, R 2 is the residue of a difunctional polypropylene glycol having a number average molecular weight of from about 1000 to about 4000, R 3 is the residue of a monofunctional polypropylene glycol monoalkyl ether having a number average molecular weight of from about 500 to about 2000, and R 4 is a C 4 -C 36 alkylene group, a diaryl methane group, or a tolyidene group.
Claim 6
Dependent Claim 177 words
A sealing composition comprising (a) from about 20 to about 50 parts by weight of at least one isocyanate-terminated polyurethane prepolymer, (b) from about 20 to about 40 parts by weight of a swellable polyvinylchloride or a swellable copolymer of vinyl chloride in powder form, (c) from about 20 to about 40 parts by weight of at least one plasticizer, and (d) from about 50 to about 150% by weight, based on component (a), of at least one diurethane of the following formulae: R.sup.1 --NH--CO--O--R.sup.2 --O--CO--NH--R.sup.1 (I) R.sup.3 --O--CO--NH--R.sup.4 --NH--CO--OR.sup.3 (II) in which R 1 is a C 3 -C 22 alkyl, C 7 -C 22 aralkyl, or phenyl radical, R 2 is the residue of a difunctional polypropylene glycol having a number average molecular weight of from about 1000 to about 4000, R 3 is the residue of a monofunctional polypropylene glycol monoalkyl ether having a number average molecular weight of from about 500 to about 2000, and R 4 is a C 4 -C 36 alkylene group, a diaryl methane group, or a tolyidene group.
Claim 7
Dependent Claim 33 words
The composition of claim 4 wherein in component (d) R 1 is a phenylalkyl radical having from 7 to 22 carbon atoms or an alkylphenylalkyl radical having from 8 to 22 carbon atoms.
Claim 8
Dependent Claim 13 words
The composition of claim 4 wherein in component (d) R 4 is diphenylmethane.
Claim 9
Dependent Claim 45 words
The composition of claim 4 wherein component (c) is at least one of an alkyl benzenesulfonic acid alkyl ester, a phthalic acid alkyl ester, an aliphatic dicarboxylic acid ester, a polyester of adipic, sebacic, azelaic or phthalic acid with a diol, or an epoxy plasticizer.
Claim 10
Dependent Claim 151 words
A composition comprising a mixture of (A) an isocyanate-terminated polyurethane prepolymer, (B) A stabilizing-effective quantity of at least one diurethane of one or both of the following formulae: R.sup.1 --NH--CO--O--R.sup.2 --O--CO--NH--R.sup.1 (I) R.sup.3 --O--CO--NH--R.sup.4 --NH--CO--OR.sup.3 (II) in which R 1 is a C 3 -C 22 alkyl, C 3 -C 22 aralkyl, or phenyl radical, R 2 is the residue of a difunctional polypropylene glycol having a number average molecular weight of from about 1000 to about 4000, R 3 is the residue of a monofunctional polypropylene glycol monoalkyl ether having a number average molecular weight of from about 500 to about 2000, and R 4 is a C 4 -C 36 alkylene group, a diaryl methane group, or a tolylidene group, wherein from about 50 to about 150% by weight of the at least one diurethane is present, based on the weight of the isocyanate-terminated polyurethane prepolymer in the composition.
Claim 11
Dependent Claim 151 words
A composition comprising a mixture of (A) an isocyanate-terminated polyurethane prepolymer, (B) A stabilizing-effective quantity of at least one diurethane of one or both of the following formulae: R.sup.1 --NH--CO--O--R.sup.2 --O--CO--NH--R.sup.1 (I) R.sup.3 --O--CO--NH--R.sup.4 --NH--CO--OR.sup.3 (II) in which R 1 is a C 3 -C 22 alkyl, C 3 -C 22 aralkyl, or phenyl radical, R 2 is the residue of a difunctional polypropylene glycol having a number average molecular weight of from about 1000 to about 4000, R 3 is the residue of a monofunctional polypropylene glycol monoalkyl ether having a number average molecular weight of from about 500 to about 2000, and R 4 is a C 4 -C 36 alkylene group, a diaryl methane group, or a tolylidene group, wherein from about 50 to about 150% by weight of the at least one diurethane is present, based on the weight of the isocyanate-terminated polyurethane prepolymer in the composition.
Claim 12
Dependent Claim 33 words
The composition of claim 8 wherein in component B R 1 is a phenylalkyl radical having from 7 to 22 carbon atoms, or an alkylphenylalkyl radical having from 8 to 22 carbon atoms.
Claim 13
Dependent Claim 13 words
The composition of claim 8 wherein in component B R 4 is diphenylmethane.
Claim 14
Dependent Claim 175 words
A plastisol composition comprising A. from about 20 to about 40 parts by weight of swellable polyvinyl chloride or a swellable copolymer of vinyl chloride, B. from about 20 to about 40 parts by weight of at least one plasticizer, C. from about 10 to about 50% by weight, based on component A., of at least one diurethane of one or both of the formulae: R.sup.1 --NH--CO--O--R.sup.2 --O--CO--NH--R.sup.1 (I) R.sup.3 --O--CO--NH--R.sup.4 --NH--CO--OR.sup.3 (II) in which R 1 is a C 3 -C 22 alkyl, C 3 -C 22 aralkyl, or phenyl radical, R 2 is the residue of a difunctional polypropylene glycol having a number average molecular weight of from about 1000 to about 4000, R 3 is the residue of a monofunctional polypropylene glycol monoalkyl ether having a number average molecular weight of from about 500 to about 2000, and R 4 is a C 4 -C 36 alkylene group, a diaryl methane group, or a tolyidene group, and D. from about 2 to about 40 parts by weight of an aromatic hydrocarbon solvent.
Claim 15
Dependent Claim 175 words
A plastisol composition comprising A. from about 20 to about 40 parts by weight of swellable polyvinyl chloride or a swellable copolymer of vinyl chloride, B. from about 20 to about 40 parts by weight of at least one plasticizer, C. from about 10 to about 50% by weight, based on component A., of at least one diurethane of one or both of the formulae: R.sup.1 --NH--CO--O--R.sup.2 --O--CO--NH--R.sup.1 (I) R.sup.3 --O--CO--NH--R.sup.4 --NH--CO--OR.sup.3 (II) in which R 1 is a C 3 -C 22 alkyl, C 3 -C 22 aralkyl, or phenyl radical, R 2 is the residue of a difunctional polypropylene glycol having a number average molecular weight of from about 1000 to about 4000, R 3 is the residue of a monofunctional polypropylene glycol monoalkyl ether having a number average molecular weight of from about 500 to about 2000, and R 4 is a C 4 -C 36 alkylene group, a diaryl methane group, or a tolyidene group, and D. from about 2 to about 40 parts by weight of an aromatic hydrocarbon solvent.
Claim 16
Dependent Claim 32 words
The composition of claim 11 wherein in component C. R 1 is a phenylalkyl radical having from 7 to 22 carbon atoms or alkylphenylalkyl radical having from 8 to 22 carbon atoms.
Claim 17
Dependent Claim 13 words
The composition of claim 11 wherein in component C. R 4 is diphenylmethane.
Claim 18
Dependent Claim 13 words
The composition of claim 11 wherein component D. is benzene, toluene, or xylene.

References Cited (Backward Citations)

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US2647916A Cited
US2879230A Cited
US3350332A Cited
US3813841A Cited
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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1992-04-24 1992-10-24 1993-04-25 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1996-04-24 1996-10-24 1997-04-25 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2000-04-24 2000-10-24 2001-04-25 $7700.00 Window Closed / Lapsed

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