← Back to Patent Explorer
US5310858A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for preparing polymers of p-xylylene from p-xylylene diesters

Assignee: Hoechst AG
•
Filing: 1993-01-28
•
Granted: 1994-05-10
•
Expires: 2013-01-28
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract The invention relates to a process for preparing compounds of the formula (I) ##STR1## by pyrolysis, where n is the degree of polymerization and is≧2. For this purposes compounds of the formula (II) --R--CO--O--CH.sub.2 --Ar--CH.sub.2 --O--CO--R (II) are pyrolyzed in one stage under conditions resulting in cleavage of the ester bonds under a partial pressure of the esters of p≦10 mbar at temperatures T≧500° C., with the formation of the corresponding derivatives of 1,4-dimethylene-2,5-cyclohexadiene, but without the latter being cleaved further in subsequent reactions. The polymers of p-xylylene formed by spontaneous polycondensation of the derivatives of 1,4-dimethylene-2,5-cyclohexadiene were then cooled, Ar and R have the following meanings: --Ar-- is a 1,4-phenylene radical or another C 6 -C 12 aromatic or heteroaromatic radical in which the bonds are in the para position or a comparable coaxial or antiparallel position; R-- is preferably branched or unbranched C 1 -C 4 -alkyl or C 6 -C 12 -aryl radical.

Inventors

  • 👤 Andreas Greiner
  • 👤 Peter Simon

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 16:16
CPC Classifications
C; C07; C07C; C07C69/00; C07C69/007; C08; C08G; C08G61/00; C08G61/02; C08G61/025

Claims Analysis

Total Claims: 9
Claim 1
Independent Claim 230 words
A process for preparing polymers of p-xylylene having repeating units of the formula (I) ##STR3## by pyrolysis, where n is the degree of polymerization and is≧2, wherein ester compounds of the formula (II) --R--CO--O--CH.sub.2 --Ar--CH.sub.2 --O--CO--R (II) are pyrolyzed in one stage under conditions resulting in cleavage of the ester bonds under a partial pressure of the esters of p≦10 mbar at temperatures T≧500° C., with the formation of corresponding derivatives of 1,4-dimethylene-2,5-cyclohexadiene, but without the latter being cleaved further in subsequent reactions, and the polymers of p-xylylene formed by spontaneous polycondensation of the derivatives of 1,4-dimethylene-2,5-cyclohexadiene were then cooled, Ar and R have the following meanings: --Ar-- is a 1,4-phenylene radical or another C 6 -C 12 aromatic or heteroaromatic radical in which the bonds are in the para position or a comparable coaxial or antiparallel position and which is unsubstituted or substituted by one or more branched or unbranched, unsubstituted or halosubstituted C 1 -C 4 -alkyl, alkenyl or alkoxy radicals or C 6 -C 12 -aryl or heteroaryl radicals, hydroxyl, nitro, nitrile or amino groups or with R*--S-- or R*--CO--O radicals, where R* is a C 1 -C 4 -alkyl radical or a C 6 -C 12 -aryl radical; R-- is branched or unbranched C 1 -C 4 -alkyl or C 6 -C 12 -aryl radical or an R*--CO--O radical, where R* has the meaning given above.
Claim 2
Dependent Claim 230 words
A process for preparing polymers of p-xylylene having repeating units of the formula (I) ##STR3## by pyrolysis, where n is the degree of polymerization and is≧2, wherein ester compounds of the formula (II) --R--CO--O--CH.sub.2 --Ar--CH.sub.2 --O--CO--R (II) are pyrolyzed in one stage under conditions resulting in cleavage of the ester bonds under a partial pressure of the esters of p≦10 mbar at temperatures T≧500° C., with the formation of corresponding derivatives of 1,4-dimethylene-2,5-cyclohexadiene, but without the latter being cleaved further in subsequent reactions, and the polymers of p-xylylene formed by spontaneous polycondensation of the derivatives of 1,4-dimethylene-2,5-cyclohexadiene were then cooled, Ar and R have the following meanings: --Ar-- is a 1,4-phenylene radical or another C 6 -C 12 aromatic or heteroaromatic radical in which the bonds are in the para position or a comparable coaxial or antiparallel position and which is unsubstituted or substituted by one or more branched or unbranched, unsubstituted or halosubstituted C 1 -C 4 -alkyl, alkenyl or alkoxy radicals or C 6 -C 12 -aryl or heteroaryl radicals, hydroxyl, nitro, nitrile or amino groups or with R*--S-- or R*--CO--O radicals, where R* is a C 1 -C 4 -alkyl radical or a C 6 -C 12 -aryl radical; R-- is branched or unbranched C 1 -C 4 -alkyl or C 6 -C 12 -aryl radical or an R*--CO--O radical, where R* has the meaning given above.
Claim 3
Dependent Claim 20 words
The process as claimed in claim 1, wherein the pyrolysis temperature is in the range from 500° to 1000° C.
Claim 4
Dependent Claim 34 words
The process as claimed in claim 1, wherein the pyrolysis of the compounds of the formula (II) and the condensation of the derivatives of 1,4-dimethylene-2,5-cyclohexadiene formed therefrom is at a partial pressure p≦10 mbar.
Claim 5
Dependent Claim 17 words
The process as claimed in claim 1, wherein two or more differently substituted xylylene diesters are pyrolyzed.
Claim 6
Dependent Claim 20 words
The process as claimed in claim 1, wherein the pyrolysis temperature is in the range from 700° to 900° C.
Claim 7
Dependent Claim 34 words
The process as claimed in claim 1, wherein the pyrolysis of the compounds of the formula (II) and the condensation of the derivatives of 1,4-dimethylene-2,5-cyclohexadiene formed therefrom is at a partial pressure p≦1 mbar.
Claim 8
Dependent Claim 220 words
A process for preparing polymers of p-xylylene having repeating units of the formula (I) ##STR4## by pyrolysis, where n is the degree of polymerization and is≧2, wherein ester compounds of the formula (II) --R--CO--O--CH.sub.2 --Ar--CH.sub.2 --O--CO--R (II) are pyrolyzed in on stage under conditions resulting in cleavage of the ester bonds under a partial pressure of the esters of p≦10 mbar at temperatures T≧500° C., with the formation of corresponding derivatives of 1,4-dimethylene-2,5-cyclohexadiene and the polymers of p-xylylene formed by spontaneous polycondensation of the derivatives of 1,4-dimethylene-2,5-cyclohexadine, then cooled, where Ar and R have the following meanings: --Ar-- is a 1,4-phenylene radical or another C 6 -C 12 aromatic or heteroaromatic radical in which the bonds are in the para position or a comparable coaxial or antiparallel position and which is unsubstituted or substituted by one or more branched or unbranched, unsubstituted or halosubstituted C 1 -C 4 -alkyl, alkenyl or alkoxy radicals or C 6 -C 12 -aryl or heteroaryl radicals, hydroxyl, nitro, nitrile or amino groups or with R*--S-- or R*--CO--O radicals, where R* is a C 1 -C 4 -alkyl radical or a C 6 -C 12 -aryl radical; R-- is branched or unbranched C 1 -C 4 -alkyl or C 6 -C 12 -aryl radical or an R*--CO--O radical, where R* has the meaning given above.
Claim 9
Dependent Claim 220 words
A process for preparing polymers of p-xylylene having repeating units of the formula (I) ##STR4## by pyrolysis, where n is the degree of polymerization and is≧2, wherein ester compounds of the formula (II) --R--CO--O--CH.sub.2 --Ar--CH.sub.2 --O--CO--R (II) are pyrolyzed in on stage under conditions resulting in cleavage of the ester bonds under a partial pressure of the esters of p≦10 mbar at temperatures T≧500° C., with the formation of corresponding derivatives of 1,4-dimethylene-2,5-cyclohexadiene and the polymers of p-xylylene formed by spontaneous polycondensation of the derivatives of 1,4-dimethylene-2,5-cyclohexadine, then cooled, where Ar and R have the following meanings: --Ar-- is a 1,4-phenylene radical or another C 6 -C 12 aromatic or heteroaromatic radical in which the bonds are in the para position or a comparable coaxial or antiparallel position and which is unsubstituted or substituted by one or more branched or unbranched, unsubstituted or halosubstituted C 1 -C 4 -alkyl, alkenyl or alkoxy radicals or C 6 -C 12 -aryl or heteroaryl radicals, hydroxyl, nitro, nitrile or amino groups or with R*--S-- or R*--CO--O radicals, where R* is a C 1 -C 4 -alkyl radical or a C 6 -C 12 -aryl radical; R-- is branched or unbranched C 1 -C 4 -alkyl or C 6 -C 12 -aryl radical or an R*--CO--O radical, where R* has the meaning given above.

References Cited (Backward Citations)

GB650947A Cited
GB673651A Cited
GB807196A Cited
US3149175A Cited
US3300322A Cited
US3300332A Cited
US3288728A Cited
US3342754A Cited
US3412167A Cited
EP0294651A1 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1997-05-09 1997-11-08 1998-05-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2001-05-09 2001-11-08 2002-05-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2005-05-09 2005-11-08 2006-05-10 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag