US1972091A - Cellulose derivative composition - Google Patents
Cellulose derivative composition Download PDFInfo
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- US1972091A US1972091A US543387A US54338731A US1972091A US 1972091 A US1972091 A US 1972091A US 543387 A US543387 A US 543387A US 54338731 A US54338731 A US 54338731A US 1972091 A US1972091 A US 1972091A
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- United States
- Prior art keywords
- cellulose derivative
- esters
- compositions
- composition
- cellulose
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- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title description 31
- 229920002678 cellulose Polymers 0.000 title description 23
- 239000001913 cellulose Substances 0.000 title description 23
- 150000002148 esters Chemical class 0.000 description 19
- 239000002253 acid Substances 0.000 description 14
- -1 n-octyl Chemical group 0.000 description 9
- 239000004014 plasticizer Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000002843 carboxylic acid group Chemical group 0.000 description 4
- 239000004922 lacquer Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- BAZVBVCLLGYUFS-UHFFFAOYSA-N 1-o-butyl 2-o-dodecyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC BAZVBVCLLGYUFS-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000000020 Nitrocellulose Substances 0.000 description 2
- 240000008548 Shorea javanica Species 0.000 description 2
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- PUFGCEQWYLJYNJ-UHFFFAOYSA-N didodecyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCCCC PUFGCEQWYLJYNJ-UHFFFAOYSA-N 0.000 description 2
- GHKVUVOPHDYRJC-UHFFFAOYSA-N didodecyl hexanedioate Chemical compound CCCCCCCCCCCCOC(=O)CCCCC(=O)OCCCCCCCCCCCC GHKVUVOPHDYRJC-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229920001220 nitrocellulos Polymers 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- WGQVJOPQTOUKDI-UHFFFAOYSA-N 2-dodecoxycarbonylbenzoic acid Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1C(O)=O WGQVJOPQTOUKDI-UHFFFAOYSA-N 0.000 description 1
- JBQKDXQJSYBVEN-UHFFFAOYSA-N 6-dodecoxy-6-oxohexanoic acid Chemical compound CCCCCCCCCCCCOC(=O)CCCCC(O)=O JBQKDXQJSYBVEN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000005336 safety glass Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- UYERRXOXXRNFHC-UHFFFAOYSA-N tridodecyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CCCCCCCCCCCCOC(=O)CC(O)(C(=O)OCCCCCCCCCCCC)CC(=O)OCCCCCCCCCCCC UYERRXOXXRNFHC-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
Definitions
- An object of the present invention is to provide cellulose derivative compositions of improved water resistance.
- a further object is to provide cellulose derivative compositions which are substantially permanently flexible, and having improved durability.
- esters of organic polycarboxylic acids at least one acid hydrogen atom of which has been replaced by a normal saturated aliphatic radical containing from 6-15 carbon atoms, as a plasticizer for the cellulose derivative.
- esters of any of the organic polycarboxylic acids whether belonging to the aromatic or aliphatic series.
- One or more of the carboxylic hydrogen atoms is replaced by a normal saturated aliphatic radical containing from 6-15 carbon atoms corresponding to the following list of alcohols:
- an ester containing one normal saturated aliphatic group having 6-15 carbon atoms may have another carboxylic acid group esterified with any other alcohol.
- the invention also includes the use of esters of polycarboxylic acids in which more than one acid hydrogen is replaced with a normal saturated aliphatic group having from 6-15 carbon atoms. Accordingly.,the invention .includes the use of neutral esters of organic polycarboxylic acids in which all of the carboxylic acid groups are esterified, such esters containing one or more of the alkyl groups listed above.
- the polycarboxylic acids which may be esterifled to yield the esters included within the present invention may contain two or more carboxylic acid groups.
- the following organic acids are named as typical of those which may be used:- orthophthalic, terephthalic, oxalic, succinic, adipic, maleic, fumaric, tartaric, malic, citric, quinolinic, trimesic, pyromellitic, naphthalic, naphthalene, tetracarboxylic, tricarballylic, hexahydrophthalic, hydro'xy phthalic, uvitic, tetrachlorophthalic, sebacic, itaconic, and pimelic.
- the removal of this water may be assisted by adding to the esterification mixture a carrier liquid, such as benzene 'or toluene, which will distill out with the water at a temperature below 100 C., in which case the esterification may be carried on at a lower tem-' perature than would otherwise be used.
- a carrier liquid such as benzene 'or toluene
- An inert gas such as carbon dioxide, may be continuously passed through the reacting mixture to accom-' plish the same purpose, namely, to facilitate the removal of water.
- any suitable solvent such as a mixture of alcohols and esters and hydrocarbons, may be used, as will be understood by those skilled in the art. Solvents may also be used with the molding compositions, if desired. As will also be obvious to those skilledin the art, various gums, natural or synthetic resins, such as polyhydric alcoholpolybasic acid or phenol-formaldehyde resins, pigments, and the like, may be included in these compositions.
- dicarboxylic acid esters may be used, as shown in the above compositions, but also tricarboxylic, or higher polycarboxylic acid esters may be used, such as trilauryl citrate.
- the cellulose derivative compositions containing the esters described above may be used either as lacquers or as molding compositions, as shown in the above examples, or asdopes for usein the preparation of coated fabrics.
- lacquers and the dopes they may be applied by spraying, brushing, flowing, spreading under a doctor knife, or by other suitable methods of application.
- moldingcompositions they can be molded according to the known methods of the plastic a'rt. They also can be'pressed into cakes and sheeted to form comparatively thin films which find use as strengthening layers for safety glass and in other applications where materials of this sort are regularly used.
- the cellulose derivative compositions which may include esters or ethers, are characterized by the fact that they are exceptionally resistant to water, since the plasticizers used in these compositions are all esters of higher aliphatic alcohols. having substantial water resistance.
- the compositions are exceptionally durable and substantially permanently flexible, due to the use of the I herein described esters as plasticizers. These esters have higher molecular weightsthan the 95 commonly used plasticizers and, consequently, have higher boiling points and lower vapor pressures, properties which insure substantially permanent retention of the plasticizer in the ,cellulose derivative composition, and hence a flexible 10D and durable product.
- the esters are satisfactorily compatible with cellulose derivatives and give compositions of exceptionally favorable properties. i
- composition of matter comprising a cellulose derivative and a lauryl phthalate.
- composition. ofmatter comprising a cellulose derivative and a lauryl adipate.
- composition of matter comprising a cellulose derivative and a lauryl ester of an organic polycarboxylic acid.
- composition of matter comprising a cellulose derivative and a lauryl ester of an organic dicarboxylic acid.
- composition of matter comprising a cellulose derivative and a di-lauryl ester of an organic dicarboxylic acid.
- composition of matter comprising a cellulose derivative and a lauryl alkyl phthalate.
- composition of matter comprising a cellulose derivative and lauryl butyl phthalate.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
Patented Sept. 4, 1934 UNITED STA 1,972,091 CELLULOSE DERIVATIVE COMPOSITION George De Witt -Grav Lawson, Wilmington,
du Pont de Nemours & Company,
es and Walter Eastby Del., assignors to E. I. Wilmington,
DeL, a corporation of Delaware No Drawing. Application June 10, 1931, Serial No. 543,387
9 Claims.
This invention relates to cellulose derivative compositions and, more particularly, to such compositions including, as plasticizers therefor, organic polycarboxylic acid esters containing an esterified higher alkyl group.
An object of the present invention is to provide cellulose derivative compositions of improved water resistance. A further object is to provide cellulose derivative compositions which are substantially permanently flexible, and having improved durability. Other objects will be apparent from the description of the invention hereinafter given.
The above objects are accomplished according to the present invention by the use of esters of organic polycarboxylic acids, at least one acid hydrogen atom of which has been replaced by a normal saturated aliphatic radical containing from 6-15 carbon atoms, as a plasticizer for the cellulose derivative.
The invention contemplates within its scope the use of esters of any of the organic polycarboxylic acids, whether belonging to the aromatic or aliphatic series. One or more of the carboxylic hydrogen atoms is replaced by a normal saturated aliphatic radical containing from 6-15 carbon atoms corresponding to the following list of alcohols:
0 n-hexyl CsHuOH n-heptyl C7H15OH n-octyl CsH1'z0H n-nonyl C9H19OH n-decyl C1oH21OH 5 n-undecyl CnHzaol-l 1all1Iy1 C12H25OH n-tridecyl C13H2'IOH myristyl C14H29OH n-pentadecyl C15H31OH The esters may contain only one of the above listed allgyl groups and may contain a free carboxylic acid group. Alternatively, an ester containing one normal saturated aliphatic group having 6-15 carbon atoms, may have another carboxylic acid group esterified with any other alcohol. The invention also includes the use of esters of polycarboxylic acids in which more than one acid hydrogen is replaced with a normal saturated aliphatic group having from 6-15 carbon atoms. Accordingly.,the invention .includes the use of neutral esters of organic polycarboxylic acids in which all of the carboxylic acid groups are esterified, such esters containing one or more of the alkyl groups listed above.
'55 The polycarboxylic acids which may be esterifled to yield the esters included within the present invention may contain two or more carboxylic acid groups. The following organic acids are named as typical of those which may be used:- orthophthalic, terephthalic, oxalic, succinic, adipic, maleic, fumaric, tartaric, malic, citric, quinolinic, trimesic, pyromellitic, naphthalic, naphthalene, tetracarboxylic, tricarballylic, hexahydrophthalic, hydro'xy phthalic, uvitic, tetrachlorophthalic, sebacic, itaconic, and pimelic.
In our copending applicationexecutedof even date herewith, Serial No. 543,386, thgesters included within the present invention are disclosed, as Well as their method of preparation. These esters are preferably made by bringing together the desired alcohols and acids (or where the anhydride of the polycarboxylic acid is available it may be used in lieu of the acid) and then heating the mixture, preferably at temperatures above 100 C. so that the water produced by the esterification will boil off and thus permit the reaction to go to completion. The removal of this water may be assisted by adding to the esterification mixture a carrier liquid, such as benzene 'or toluene, which will distill out with the water at a temperature below 100 C., in which case the esterification may be carried on at a lower tem-' perature than would otherwise be used. An inert gas, such as carbon dioxide, may be continuously passed through the reacting mixture to accom-' plish the same purpose, namely, to facilitate the removal of water.
The following examples are given to illustrate typical molding and lacquer cellulose derivative compositions employing the above described esters as plasticizers for the cellulose derivative Momma CoMPosrrions Tricresyl phosphate 15 Example 3 Parts Cellulose acetate 100 Dilauryl phthalate 30 Example 4 Parts Cellulose acetate Dilauryl phthal 20 Triacetin 15 Example 5 Parts Cellulosev nitrate 100 Lauryl butyl phthalate 35 LACQUEli Courosrrrons Example 6 Parts Cellulose nitrate 12 Damar--- 3 Lauryl butyl adipate 4 Castor 011 y .2. 6 Solvent 24 Example 7 Parts Benzyl cellulose 4 Dilauryl succinate 1 Hexyl caproate 1 Solvent. -1 24 Example 8 Parts Benzyl cellulose I 4 Damar' 1 Dioctyl adipate 1 Solvent 24 Example 9 Parts Cellulose nitrate 12. 0 Damar 3. 0 Dilauryl adipate 4. 0 Pigment 16. 3 Castor oil I 2. 6 Solvent 161.6
In the above examples, showing lacquer compositions, any suitable solvent, such as a mixture of alcohols and esters and hydrocarbons, may be used, as will be understood by those skilled in the art. Solvents may also be used with the molding compositions, if desired. As will also be obvious to those skilledin the art, various gums, natural or synthetic resins, such as polyhydric alcoholpolybasic acid or phenol-formaldehyde resins, pigments, and the like, may be included in these compositions.
Not only dicarboxylic acid esters may be used, as shown in the above compositions, but also tricarboxylic, or higher polycarboxylic acid esters may be used, such as trilauryl citrate. The cellulose derivative compositions containing the esters described above may be used either as lacquers or as molding compositions, as shown in the above examples, or asdopes for usein the preparation of coated fabrics. In the case of the lacquers and the dopes, they may be applied by spraying, brushing, flowing, spreading under a doctor knife, or by other suitable methods of application. When used as moldingcompositions they can be molded according to the known methods of the plastic a'rt. They also can be'pressed into cakes and sheeted to form comparatively thin films which find use as strengthening layers for safety glass and in other applications where materials of this sort are regularly used.
The cellulose derivative compositions, which may include esters or ethers, are characterized by the fact that they are exceptionally resistant to water, since the plasticizers used in these compositions are all esters of higher aliphatic alcohols. having substantial water resistance. The compositions are exceptionally durable and substantially permanently flexible, due to the use of the I herein described esters as plasticizers. These esters have higher molecular weightsthan the 95 commonly used plasticizers and, consequently, have higher boiling points and lower vapor pressures, properties which insure substantially permanent retention of the plasticizer in the ,cellulose derivative composition, and hence a flexible 10D and durable product. The esters are satisfactorily compatible with cellulose derivatives and give compositions of exceptionally favorable properties. i
As many apparently widely diiferent embodiments of this invention may be made without departing from the spirit and scope thereof, it is to be understood that'we do not limit ourselves to the specific embodiments thereof except as defined in the appended claims.
We claim:
1. A composition of matter comprising a cellulose derivative and a lauryl phthalate.
2. A composition of matter comprising a cellulose derivative and dilauryl phthalate.
3. A composition. ofmatter comprising a cellulose derivative and a lauryl adipate.
4. A composition of matter comprising a cellulose derivative and dilauryl adipate.
5. A composition of matter comprising a cellulose derivative and a lauryl ester of an organic polycarboxylic acid.
6. A composition of matter comprising a cellulose derivative and a lauryl ester of an organic dicarboxylic acid. a
7. A composition of matter comprising a cellulose derivative and a di-lauryl ester of an organic dicarboxylic acid.
8. A composition of matter comprising a cellulose derivative and a lauryl alkyl phthalate.
9. A composition of matter comprising a cellulose derivative and lauryl butyl phthalate.
GEORGE DE WI'I'I' GRAVES. WALTER EAS'I'BY LAWSON.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US543387A US1972091A (en) | 1931-06-10 | 1931-06-10 | Cellulose derivative composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US543387A US1972091A (en) | 1931-06-10 | 1931-06-10 | Cellulose derivative composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1972091A true US1972091A (en) | 1934-09-04 |
Family
ID=24167803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US543387A Expired - Lifetime US1972091A (en) | 1931-06-10 | 1931-06-10 | Cellulose derivative composition |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1972091A (en) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2465472A (en) * | 1944-12-21 | 1949-03-29 | Celanese Corp | Stabilized ethyl cellulose composition |
| DE969104C (en) * | 1942-07-31 | 1958-04-30 | Siemens Ag | Plasticizer for plastic mixtures on the basis of cellulose triacetate |
| US6471604B2 (en) | 1999-11-01 | 2002-10-29 | Callaway Golf Company | Multiple material golf head |
| USD481774S1 (en) | 2003-05-29 | 2003-11-04 | Callaway Golf Company | Golf club head |
| USD482091S1 (en) | 2003-05-30 | 2003-11-11 | Callaway Golf Company | Golf club head |
| US20040171040A1 (en) * | 2002-11-22 | 2004-09-02 | Veeraiah Bodepudi | Detectable labeled nucleoside analogs and methods of use thereof |
| USD510116S1 (en) | 2003-05-29 | 2005-09-27 | Callaway Golf Company | Golf club head |
| US20090293259A1 (en) * | 2008-06-02 | 2009-12-03 | Callaway Golf Company | Method for constructing a multiple piece golf club head |
| US20100000071A1 (en) * | 2008-07-02 | 2010-01-07 | Callaway Golf Company | Method for constructing a multiple piece golf club head |
| US20100139079A1 (en) * | 2008-12-04 | 2010-06-10 | Callaway Golf Company | Method for forming a multiple material golf club head |
| US20100139078A1 (en) * | 2008-12-04 | 2010-06-10 | Callaway Golf Company | Method for forming a multiple material fairway-type golf club head |
| US20100144463A1 (en) * | 2008-12-04 | 2010-06-10 | Callaway Golf Company | Multiple material driver-type golf club head |
| US20110065528A1 (en) * | 2009-09-15 | 2011-03-17 | Callaway Golf Company | Multiple material golf club head and a method for forming a golf club head |
| WO2013025277A1 (en) | 2011-08-15 | 2013-02-21 | Exxonmobil Chemical Patents Inc. | Esters and their preparation and use |
-
1931
- 1931-06-10 US US543387A patent/US1972091A/en not_active Expired - Lifetime
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE969104C (en) * | 1942-07-31 | 1958-04-30 | Siemens Ag | Plasticizer for plastic mixtures on the basis of cellulose triacetate |
| US2465472A (en) * | 1944-12-21 | 1949-03-29 | Celanese Corp | Stabilized ethyl cellulose composition |
| US6471604B2 (en) | 1999-11-01 | 2002-10-29 | Callaway Golf Company | Multiple material golf head |
| US20040171040A1 (en) * | 2002-11-22 | 2004-09-02 | Veeraiah Bodepudi | Detectable labeled nucleoside analogs and methods of use thereof |
| USD481774S1 (en) | 2003-05-29 | 2003-11-04 | Callaway Golf Company | Golf club head |
| USD510116S1 (en) | 2003-05-29 | 2005-09-27 | Callaway Golf Company | Golf club head |
| USD482091S1 (en) | 2003-05-30 | 2003-11-11 | Callaway Golf Company | Golf club head |
| US20090293259A1 (en) * | 2008-06-02 | 2009-12-03 | Callaway Golf Company | Method for constructing a multiple piece golf club head |
| US20100000071A1 (en) * | 2008-07-02 | 2010-01-07 | Callaway Golf Company | Method for constructing a multiple piece golf club head |
| US20100071193A1 (en) * | 2008-07-02 | 2010-03-25 | Callaway Golf Company | Method for constructing a multiple piece golf club head |
| US20100139079A1 (en) * | 2008-12-04 | 2010-06-10 | Callaway Golf Company | Method for forming a multiple material golf club head |
| US20100139078A1 (en) * | 2008-12-04 | 2010-06-10 | Callaway Golf Company | Method for forming a multiple material fairway-type golf club head |
| US20100144463A1 (en) * | 2008-12-04 | 2010-06-10 | Callaway Golf Company | Multiple material driver-type golf club head |
| US20110065528A1 (en) * | 2009-09-15 | 2011-03-17 | Callaway Golf Company | Multiple material golf club head and a method for forming a golf club head |
| US8425349B2 (en) | 2009-09-15 | 2013-04-23 | Callaway Golf Company | Multiple material golf club head and a method for forming a golf club head |
| WO2013025277A1 (en) | 2011-08-15 | 2013-02-21 | Exxonmobil Chemical Patents Inc. | Esters and their preparation and use |
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