← Back to Patent Explorer
US4189407A Expired / Lapsed US ⏱️ 0.0 years remaining

Chlorinated hydrocarbons and polysulfide rubber sealant compositions incorporating same

Assignee: Dover Chemical Corp
•
Filing: 1976-10-20
•
Granted: 1980-02-19
•
Expires: 1996-10-20
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract An improved chlorinated hydrocarbon is provided which is uniquely compatible with polysulfide rubber sealant formulations when incorporated as a plasticizer therein. Paraffins or alpha-olefins containing from 16 to 20 carbon atoms per molecule or mixtures or blends of paraffins or alpha-olefins containing 16 to 20 carbon atoms per molecule are chlorinated to a final chlorine content of from between 52 and 58 weight percent chlorine. The chlorinated hydrocarbons are compatible with polysulfide rubber sealant formulations while still maintaining the necessary low viscosity and volatility when incorporated as a plasticizer therein. A modified polysulfide rubber sealant formulation is disclosed which incorporates as a plasticizer the improved chlorinated hydrocarbon, and which is useful as a glass or window sealant. The improved plasticizer is non-fogging in a polysulfide rubber formulation.

Inventors

  • 👤 Cyril J. Yaggi, Jr.

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-30 13:15
CPC Classifications
C; C09; C09J; C09J181/00; C09J181/04; C09K; C09K2200/00; C09K2200/04; C09K2200/0411

Claims Analysis

Total Claims: 23
Claim 1
Independent Claim 115 words
An improved polysulfide rubber sealant formulation comprising a liquid polysulfide polymer; and a chlorinated hydrocarbon plasticizer in an amount effective to plasticize said polysulfide polymer and consisting essentially of a chlorinated hydrocarbon selected from chlorinated paraffins containing from 16 to 20 carbon atoms per molecule, chlorinated alpha-olefins containing from 16 to 20 carbon atoms per molecule, and mixtures thereof; the chlorine content of the chlorinated hydrocarbon ranging from 52 to 58 weight percent; the chlorinated hydrocarbon plasticizer having a combination of (a) number of carbon atoms per molecule and (b) chlorine content sufficient to provide a non-fogging and compatible plasticizer in a polysulfide rubber sealant formulation; the polysulfide rubber sealant formulation being stable when cured.
Claim 2
Dependent Claim 115 words
An improved polysulfide rubber sealant formulation comprising a liquid polysulfide polymer; and a chlorinated hydrocarbon plasticizer in an amount effective to plasticize said polysulfide polymer and consisting essentially of a chlorinated hydrocarbon selected from chlorinated paraffins containing from 16 to 20 carbon atoms per molecule, chlorinated alpha-olefins containing from 16 to 20 carbon atoms per molecule, and mixtures thereof; the chlorine content of the chlorinated hydrocarbon ranging from 52 to 58 weight percent; the chlorinated hydrocarbon plasticizer having a combination of (a) number of carbon atoms per molecule and (b) chlorine content sufficient to provide a non-fogging and compatible plasticizer in a polysulfide rubber sealant formulation; the polysulfide rubber sealant formulation being stable when cured.
Claim 3
Dependent Claim 78 words
An improved polysulfide rubber sealant formulation according to claim 1 wherein the liquid polysulfide polymer is thiol-terminated; the chlorinated hydrocarbon is selected from chlorinated paraffins containing from 16 to 18 carbon atoms per molecule, chlorinated alpha-olefins containing from 16 to 18 carbon atoms per molecule, and mixtures thereof; and the chlorinated hydrocarbon plasticizer has a viscosity of less than about 40,000 centipoises at 25° C. and has a heat loss value of less than about 0.5 weight percent.
Claim 4
Dependent Claim 131 words
An improved polysulfide rubber sealant formulation comprising a liquid polysulfide polymer; and a chlorinated hydrocarbon plasticizer in an amount effective to plasticize said polysulfide polymer and consisting essentially of a chlorinated alpha-olefin containing 18 carbon atoms per molecule; the chlorine content of the chlorinated alpha-olefin ranging from 54 to 55.5 weight percent; the chlorinated hydrocarbon plasticizer having a combination of (a) a number of carbon atoms per molecule and (b) chlorine content sufficient to provide a non-fogging and compatible plasticizer in a polysulfide rubber sealant formulation; the chlorinated hydrocarbon plasticizer having a viscosity of less than about 30,000 centipoises at 25° C. and having a heat loss value of less than about 0.5 weight percent; the liquid polysulfide polymer being thiol-terminated; and the polysulfide rubber sealant formulation being stable when cured.
Claim 5
Dependent Claim 131 words
An improved polysulfide rubber sealant formulation comprising a liquid polysulfide polymer; and a chlorinated hydrocarbon plasticizer in an amount effective to plasticize said polysulfide polymer and consisting essentially of a chlorinated alpha-olefin containing 18 carbon atoms per molecule; the chlorine content of the chlorinated alpha-olefin ranging from 54 to 55.5 weight percent; the chlorinated hydrocarbon plasticizer having a combination of (a) a number of carbon atoms per molecule and (b) chlorine content sufficient to provide a non-fogging and compatible plasticizer in a polysulfide rubber sealant formulation; the chlorinated hydrocarbon plasticizer having a viscosity of less than about 30,000 centipoises at 25° C. and having a heat loss value of less than about 0.5 weight percent; the liquid polysulfide polymer being thiol-terminated; and the polysulfide rubber sealant formulation being stable when cured.
Claim 6
Dependent Claim 130 words
An improved polysulfide rubber sealant formulation comprising a liquid polysulfide polymer; and a chlorinated hydrocarbon plasticizer in an amount effective to plasticize said polysulfide polymer and consisting essentially of a chlorinated alpha-olefin containing 16 carbon atoms per molecule; the chlorine content of the chlorinated alpha-olefin ranging from 54 to 55.5 weight percent; the chlorinated hydrocarbon plasticizer having a combination of (a) number of carbon atoms per molecule and (b) chlorine content sufficient to provide a non-fogging and compatible plasticizer in a polysulfide rubber sealant formulation; the chlorinated hydrocarbon plasticizer having a viscosity of less than about 10,000 centipoises at 25° C. and having a heat loss value of less than about 0.5 weight percent; the liquid polysulfide polymer being thiol-terminated; and the polysulfide rubber sealant formulation being stable when cured.
Claim 7
Dependent Claim 130 words
An improved polysulfide rubber sealant formulation comprising a liquid polysulfide polymer; and a chlorinated hydrocarbon plasticizer in an amount effective to plasticize said polysulfide polymer and consisting essentially of a chlorinated alpha-olefin containing 16 carbon atoms per molecule; the chlorine content of the chlorinated alpha-olefin ranging from 54 to 55.5 weight percent; the chlorinated hydrocarbon plasticizer having a combination of (a) number of carbon atoms per molecule and (b) chlorine content sufficient to provide a non-fogging and compatible plasticizer in a polysulfide rubber sealant formulation; the chlorinated hydrocarbon plasticizer having a viscosity of less than about 10,000 centipoises at 25° C. and having a heat loss value of less than about 0.5 weight percent; the liquid polysulfide polymer being thiol-terminated; and the polysulfide rubber sealant formulation being stable when cured.
Claim 8
Dependent Claim 86 words
An improved polysulfide rubber sealant formulation according to claim 1 wherein the chlorinated hydrocarbon plasticizer consists essentially of a mixture of equal parts by weight of an alpha-olefin containing 16 carbon atoms per molecule and an alpha-olefin containing 20 carbon atoms per molecule; the chlorine content of the chlorinated mixture ranges from 52 to 55 weight percent; and the chlorinated mixture has a viscosity of less than about 25,000 centipoises at 25° C. and has a heat loss value of less than about 0.5 weight percent.
Claim 9
Dependent Claim 139 words
An improved polysulfide rubber sealant formulation comprising a liquid polysulfide polymer; a chlorinated hydrocarbon plasticizer in an amount effective to plasticize said polysulfide polymer and consisting essentially of a chlorinated alpha-olefin containing 18 carbon atoms per molecule; the chlorine content of the chlorinated alpha-olefin ranging from 54 to 55.5 weight percent; the chlorinated hydrocarbon plasticizer having a viscosity of less than about 30,000 centipoises at 25° C., a heat loss value of less than about 0.5 weight percent and a combination of (a) number of carbon atoms per molecule and (b) chlorine content sufficient to provide a non-fogging and compatible plasticizer in a polysulfide rubber sealant formulation; a pigment; a retarding agent; and a filler; the polysulfide rubber sealant formulation being stable when cured, the curing being effected by the incorporation of an effective amount of a curing agent.
Claim 10
Dependent Claim 139 words
An improved polysulfide rubber sealant formulation comprising a liquid polysulfide polymer; a chlorinated hydrocarbon plasticizer in an amount effective to plasticize said polysulfide polymer and consisting essentially of a chlorinated alpha-olefin containing 18 carbon atoms per molecule; the chlorine content of the chlorinated alpha-olefin ranging from 54 to 55.5 weight percent; the chlorinated hydrocarbon plasticizer having a viscosity of less than about 30,000 centipoises at 25° C., a heat loss value of less than about 0.5 weight percent and a combination of (a) number of carbon atoms per molecule and (b) chlorine content sufficient to provide a non-fogging and compatible plasticizer in a polysulfide rubber sealant formulation; a pigment; a retarding agent; and a filler; the polysulfide rubber sealant formulation being stable when cured, the curing being effected by the incorporation of an effective amount of a curing agent.
Claim 11
Dependent Claim 207 words
An improved polysulfide rubber sealant formulation comprising 100 parts by weight of a thiol-terminated polysulfide polymer; from about 25 to about 100 parts by weight of a chlorinated hydrocarbon plasticizer consisting essentially of a chlorinated alpha-olefin containing 18 carbon atoms per molecule; the chlorine content of the chlorinated alpha-olefin ranging from 54 to 55.5 weight percent; the chlorinated hydrocarbon plasticizer having a viscosity of less than about 30,000 centipoises at 25° C., a heat loss value of less than about 0.5 weight percent and a combination of (a) number of carbon atoms per molecule and (b) chlorine content sufficient to provide a non-fogging and compatible plasticizer in a polysulfide rubber sealant formulation; from about 5 to about 20 parts by weight of a titanium dioxide pigment; from about 0.1 to about 5 parts by weight of a stearic acid retarding agent; and from about 25 to about 100 parts by weight of a filler selected from the group consisting of carbon black, clay, and calcium carbonate; the polysulfide rubber sealant formulation being stable when cured, the curing being effected by the incorporation of from about 5 to about 10 parts by weight of a curing paste comprising equal parts by weight of lead dioxide and phthalate ester.
Claim 12
Dependent Claim 207 words
An improved polysulfide rubber sealant formulation comprising 100 parts by weight of a thiol-terminated polysulfide polymer; from about 25 to about 100 parts by weight of a chlorinated hydrocarbon plasticizer consisting essentially of a chlorinated alpha-olefin containing 18 carbon atoms per molecule; the chlorine content of the chlorinated alpha-olefin ranging from 54 to 55.5 weight percent; the chlorinated hydrocarbon plasticizer having a viscosity of less than about 30,000 centipoises at 25° C., a heat loss value of less than about 0.5 weight percent and a combination of (a) number of carbon atoms per molecule and (b) chlorine content sufficient to provide a non-fogging and compatible plasticizer in a polysulfide rubber sealant formulation; from about 5 to about 20 parts by weight of a titanium dioxide pigment; from about 0.1 to about 5 parts by weight of a stearic acid retarding agent; and from about 25 to about 100 parts by weight of a filler selected from the group consisting of carbon black, clay, and calcium carbonate; the polysulfide rubber sealant formulation being stable when cured, the curing being effected by the incorporation of from about 5 to about 10 parts by weight of a curing paste comprising equal parts by weight of lead dioxide and phthalate ester.
Claim 13
Dependent Claim 139 words
An improved polysulfide rubber sealant formulation comprising a liquid polysulfide polymer; a chlorinated hydrocarbon plasticizer in an amount effective to plasticize said polysulfide polymer and consisting essentially of a chlorinated alpha-olefin containing 16 carbon atoms per molecule; the chlorine content of the chlorinated alpha-olefin ranging from 54 to 55.5 weight percent; the chlorinated hydrocarbon plasticizer having a viscosity of less than about 10,000 centipoises at 25° C., a heat loss value of less than about 0.5 weight percent and a combination of (a) number of carbon atoms per molecule and (b) chlorine content sufficient to provide a non-fogging and compatible plasticizer in a polysulfide rubber sealant formulation; a pigment; a retarding agent; and a filler; the polysulfide rubber sealant formulation being stable when cured, the curing being effected by the incorporation of an effective amount of a curing agent.
Claim 14
Dependent Claim 139 words
An improved polysulfide rubber sealant formulation comprising a liquid polysulfide polymer; a chlorinated hydrocarbon plasticizer in an amount effective to plasticize said polysulfide polymer and consisting essentially of a chlorinated alpha-olefin containing 16 carbon atoms per molecule; the chlorine content of the chlorinated alpha-olefin ranging from 54 to 55.5 weight percent; the chlorinated hydrocarbon plasticizer having a viscosity of less than about 10,000 centipoises at 25° C., a heat loss value of less than about 0.5 weight percent and a combination of (a) number of carbon atoms per molecule and (b) chlorine content sufficient to provide a non-fogging and compatible plasticizer in a polysulfide rubber sealant formulation; a pigment; a retarding agent; and a filler; the polysulfide rubber sealant formulation being stable when cured, the curing being effected by the incorporation of an effective amount of a curing agent.
Claim 15
Dependent Claim 208 words
An improved polysulfide rubber sealant formulation comprising about 100 parts by weight of a thiol-terminated polysulfide polymer; from about 25 to about 100 parts by weight of a chlorinated hydrocarbon plasticizer consisting essentially of a chlorinated alpha-olefin containing 16 carbon atoms per molecule; the chlorine content of the chlorinated alpha-olefin ranging from 54 to 56 weight percent; the chlorinated hydrocarbon plasticizer having a viscosity of less than about 10,000 centipoises at 25° C., a heat loss value of less than about 0.5 weight percent and a combination of (a) number of carbon atoms per molecule and (b) chlorine content sufficient to provide a non-fogging and compatible plasticizer in a polysulfide rubber sealant formulation; from about 5 to about 20 parts by weight of a titanium dioxide pigment; from about 0.1 to about 5 parts by weight of a stearic acid retarding agent; and from about 25 to about 100 parts by weight of a filler selected from the group consisting of carbon black, clay, and calcium carbonate; the polysulfide rubber sealant formulation being stable when cured, the curing being effected by the incorporation of from about 5 to about 10 parts by weight of a curing paste comprising equal parts by weight of lead dioxide and phthalate ester.
Claim 16
Dependent Claim 208 words
An improved polysulfide rubber sealant formulation comprising about 100 parts by weight of a thiol-terminated polysulfide polymer; from about 25 to about 100 parts by weight of a chlorinated hydrocarbon plasticizer consisting essentially of a chlorinated alpha-olefin containing 16 carbon atoms per molecule; the chlorine content of the chlorinated alpha-olefin ranging from 54 to 56 weight percent; the chlorinated hydrocarbon plasticizer having a viscosity of less than about 10,000 centipoises at 25° C., a heat loss value of less than about 0.5 weight percent and a combination of (a) number of carbon atoms per molecule and (b) chlorine content sufficient to provide a non-fogging and compatible plasticizer in a polysulfide rubber sealant formulation; from about 5 to about 20 parts by weight of a titanium dioxide pigment; from about 0.1 to about 5 parts by weight of a stearic acid retarding agent; and from about 25 to about 100 parts by weight of a filler selected from the group consisting of carbon black, clay, and calcium carbonate; the polysulfide rubber sealant formulation being stable when cured, the curing being effected by the incorporation of from about 5 to about 10 parts by weight of a curing paste comprising equal parts by weight of lead dioxide and phthalate ester.
Claim 17
Dependent Claim 24 words
A method for preparing an improved polysulfide rubber sealant formulation comprising mixing together the liquid polysulfide polymer and chlorinated hydrocarbon plasticizer of claim 1.
Claim 18
Dependent Claim 25 words
A method for preparing an improved polysulfide rubber sealant formulation comprising mixing together the liquid polysulfide polymer and the chlorinated hydrocarbon plasticizer of claim 3.
Claim 19
Dependent Claim 25 words
A method for preparing an improved polysulfide rubber sealant formulation comprising mixing together the liquid polysulfide polymer and the chlorinated hydrocarbon plasticizer of claim 4.
Claim 20
Dependent Claim 80 words
A method for preparing the improved polysulfide rubber sealant formulation of claim 6 comprising chlorinating a hydrocarbon consisting essentially of an alpha-olefin containing 18 carbon atoms per molecule to a chlorine content ranging from 54 to 55.5 weight percent; mixing the chlorinated alpha-olefin together with a liquid polysulfide polymer, a pigment, a retarding agent and a filler to form a polysulfide rubber sealant formulation; and curing the polysulfide rubber sealant formulation by incorporating an effective amount of a curing agent.
Claim 21
Dependent Claim 79 words
A method for preparing the improved polysulfide rubber sealant formulation of claim 8 comprising chlorinating a hydrocarbon consisting essentially of an alpha-olefin containing 16 carbon atoms per molecule to a chlorine content of 54 to 55.5 weight percent; mixing the chlorinated alpha-olefin together with a liquid polysulfide polymer, a pigment, a retarding agent and a filler to form a polysulfide rubber sealant formulation; and curing the polysulfide rubber sealant formulation by incorporating an effective amount of a curing agent.
Claim 22
Dependent Claim 154 words
A method for preparing the improved polysulfide rubber sealant formulation of claim 7 comprising chlorinating a hydrocarbon consisting essentially of an alpha-olefin containing 18 carbon atoms per molecule to a chlorine content ranging from 54 to 55.5 weight percent; mixing from about 25 to about 100 parts by weight of the chlorinated alpha-olefin together with 100 parts by weight of a liquid polysulfide polymer, from about 25 to about 100 parts by weight of a filler selected from carbon black, clay, and calcium carbonate, from about 0.1 to about 5 parts by weight of a stearic acid retarding agent and from about 5 to about 20 parts by weight of a titanium dioxide pigment to form a polysulfide rubber sealant formulation; and curing the polysulfide rubber sealant formulation by incorporating from about 5 to about 10 parts by weight of a curing paste comprising equal parts by weight of phthalate ester and lead dioxide.
Claim 23
Dependent Claim 154 words
A method for preparing the improved polysulfide rubber sealant formulation of claim 9 comprising chlorinating a hydrocarbon consisting essentially of an alpha-olefin containing 16 carbon atoms per molecule to a chlorine content ranging from 54 to 55.5 weight percent; mixing from about 25 to about 100 parts by weight of the chlorinated alpha-olefin together with 100 parts by weight of a liquid polysulfide polymer, from about 25 to about 10 parts by weight of a filler selected from carbon black, clay and calcium carbonate, from about 0.1 to about 5 parts by weight of a stearic acid retarding agent and from about 5 to about 20 parts by weight of a titanium dioxide pigment to form a polysulfide rubber sealant formulation; and curing the polysulfide rubber sealant formulation by incorporating from about 5 to about 10 parts by weight of a curing paste comprising equal parts by weight of phthalate ester and lead dioxide.

References Cited (Backward Citations)

US3567610A Cited
US3848006A Cited
US3919338A Cited
US3770678A Cited
US3896183A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1983-02-18 1983-08-20 1984-02-19 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-02-18 1987-08-20 1988-02-19 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-02-18 1991-08-20 1992-02-19 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag