US2501337A - Treatment of cellulosic fibrous materials - Google Patents
Treatment of cellulosic fibrous materials Download PDFInfo
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- US2501337A US2501337A US636066A US63606645A US2501337A US 2501337 A US2501337 A US 2501337A US 636066 A US636066 A US 636066A US 63606645 A US63606645 A US 63606645A US 2501337 A US2501337 A US 2501337A
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- US
- United States
- Prior art keywords
- fibers
- carbon atoms
- aliphatic
- alcohol
- treating
- Prior art date
- 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.)
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- 239000002657 fibrous material Substances 0.000 title claims description 25
- -1 MONO-OXY Chemical group 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 32
- 239000000835 fiber Substances 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 23
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 150000002576 ketones Chemical class 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 10
- 150000001298 alcohols Chemical class 0.000 claims description 10
- 229930195733 hydrocarbon Natural products 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 230000006872 improvement Effects 0.000 claims description 8
- 150000001299 aldehydes Chemical class 0.000 claims description 7
- 239000000080 wetting agent Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000002430 hydrocarbons Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 description 31
- 238000009736 wetting Methods 0.000 description 21
- 125000004430 oxygen atom Chemical group O* 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 150000001721 carbon Chemical group 0.000 description 6
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical group CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 201000006747 infectious mononucleosis Diseases 0.000 description 4
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 4
- VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 239000012266 salt solution Substances 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 2
- GYSCXPVAKHVAAY-UHFFFAOYSA-N 3-Nonanol Chemical compound CCCCCCC(O)CC GYSCXPVAKHVAAY-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 2
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical group CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl 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])[H] 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- YNMZZHPSYMOGCI-UHFFFAOYSA-N undecan-3-one Chemical compound CCCCCCCCC(=O)CC YNMZZHPSYMOGCI-UHFFFAOYSA-N 0.000 description 2
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- YSLBFFIVJGJBSA-UHFFFAOYSA-N (4-ethylphenyl)methanol Chemical compound CCC1=CC=C(CO)C=C1 YSLBFFIVJGJBSA-UHFFFAOYSA-N 0.000 description 1
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 1
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical group CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 1
- FAYUSHUTMRYHAD-UHFFFAOYSA-N 1-(cyclohexen-1-yl)ethanol Chemical compound CC(O)C1=CCCCC1 FAYUSHUTMRYHAD-UHFFFAOYSA-N 0.000 description 1
- RCHLXMOXBJRGNX-UHFFFAOYSA-N 1-butylcyclohexan-1-ol Chemical group CCCCC1(O)CCCCC1 RCHLXMOXBJRGNX-UHFFFAOYSA-N 0.000 description 1
- AXINNNJHLJWMTC-UHFFFAOYSA-N 2,2,4-trimethylpentan-3-ol Chemical compound CC(C)C(O)C(C)(C)C AXINNNJHLJWMTC-UHFFFAOYSA-N 0.000 description 1
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 description 1
- WFZFXUZFKAOTRR-UHFFFAOYSA-N 2,6-dimethyl-5-hepten-1-ol Chemical compound OCC(C)CCC=C(C)C WFZFXUZFKAOTRR-UHFFFAOYSA-N 0.000 description 1
- XYYMFUCZDNNGFS-UHFFFAOYSA-N 2-methylheptan-3-one Chemical compound CCCCC(=O)C(C)C XYYMFUCZDNNGFS-UHFFFAOYSA-N 0.000 description 1
- SDJUYPUXVFDUFF-UHFFFAOYSA-N 2-propan-2-ylcyclohexan-1-one Chemical compound CC(C)C1CCCCC1=O SDJUYPUXVFDUFF-UHFFFAOYSA-N 0.000 description 1
- CCCIYAQYQZQDIZ-UHFFFAOYSA-N 6-methylheptan-3-one Chemical compound CCC(=O)CCC(C)C CCCIYAQYQZQDIZ-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 244000198134 Agave sisalana Species 0.000 description 1
- 241000004297 Draba Species 0.000 description 1
- 240000000907 Musa textilis Species 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910052614 beryl Inorganic materials 0.000 description 1
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000000484 citronellol Nutrition 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 125000002704 decyl 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])* 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000009792 diffusion process Methods 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
- 239000000975 dye Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Chemical group CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- WGDUEFYADBRNKG-UHFFFAOYSA-N oct-2-en-4-ol Chemical compound CCCCC(O)C=CC WGDUEFYADBRNKG-UHFFFAOYSA-N 0.000 description 1
- WOFPPJOZXUTRAU-UHFFFAOYSA-N octan-4-ol Chemical compound CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- MTZWHHIREPJPTG-UHFFFAOYSA-N phorone Chemical compound CC(C)=CC(=O)C=C(C)C MTZWHHIREPJPTG-UHFFFAOYSA-N 0.000 description 1
- 229930193351 phorone Natural products 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- CZPRKINNVBONSF-UHFFFAOYSA-M zinc;dioxido(oxo)phosphanium Chemical compound [Zn+2].[O-][P+]([O-])=O CZPRKINNVBONSF-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/144—Alcohols; Metal alcoholates
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/12—Aldehydes; Ketones
- D06M13/127—Mono-aldehydes, e.g. formaldehyde; Monoketones
Definitions
- This invention relates :to a process for the treatment of fibrous materials.
- .a process for the Wetting put of fibrous materials, particularly cellulosic material such as notton fibrous material, wherein the material is first treated with a .mono-oxy compound having h oxygen atom directly linked to a single carbon atom of a hydrocarbon. radical of eight to eleven carbon atoms ioll wed by .a trea ment W th an aqueous solution of an anion active detergent or wetting agent such as a water-soluble salt of an organic compound in which a hydrocarbon radical is linked with a carboxylated, sulfonated or sulfated solubiliz-ing group through an ester, amide or aryl linkage.
- an anion active detergent or wetting agent such as a water-soluble salt of an organic compound in which a hydrocarbon radical is linked with a carboxylated, sulfonated or sulfated solubiliz-ing group through an ester, amide or aryl linkage.
- detergents which are commercially available are the salts of sulfonated or sulfatfid primary aliphatic alcohols (containing at least eight carbon atoms in the molecule) derived from fatty acid sources; the salts of sulfonated or suliated secondary aliphatic alcohols (containing at least eight carbon atoms in the molecule) derived from synthetic sources such as petroleum; salts of isethionio acid .101 o taurine condensation products with -fatty acids and salts of alkyl, aryl, .ara1kv a1ka y1, or beryl sulfonates.
- the .term keryl refers to the radical of an aliphatic hydrocarbon obtainable from kerosene.
- carboxylated type of detergent are: fatty acid, naphthenioor rosin acidsoaps.
- the mono-oxy compound used in'the first step of the pro ess i analcoho most me era ly a ary o seconda y alcohol, orami tore thereof having an av rage hain length of ei to eleven arbon atoms pe mo ule, an preferably the anion active compound .used in the second step is a sulfated aliphatic alcohol detergent, most preferably a sodiumsalt of .a sulfated aliphatic alcohol containing from eight .toeighteen (and preferably sixteen to eighteen) carbon atoms .in the 311101801113, or a mixtureiof such salt-s such as is obtained by the sulfation of a mixture of olefins containin ;from six to eighteen carbon atoms in :the molecule.
- a sulfated aliphatic alcohol detergent most preferably a sodiumsalt of .a sulfated aliphatic alcohol containing from
- While :the :invention will 17 Claims. (01. 117-56) be particularly described with reference to the use in the first step of alcohols having an average chain length of eight to eleven, most preferably about nine, carbon atoms because of their out.- standing superiority, it is also applicable to other mono-oxy compounds wherein the oxygen atom is linked to a single carbon atom of a hydrocarbon radical of eight to eleven carbon atoms, such :as ketones and aldehydes.
- teriaLl with an alcohol, ;or other :mQDO-Qxy cornpound wherein :the ,oi-l en atom is directly linked to is, single carbon atom of a.hydrocarbon radical having an average length in the compound or mixture thereof used .of eight to eleven carbon atoms, before contacting the fibers with the aqu ou -wet in solution.
- Another obje tondary aliphatic alcohols having a straight hydrocarbon chain of eight to eleven carbon atoms such as n-octyl alcohol, n-nonyl alcohol, n-decyl alcohol, n-undecyl alcohol, Z-octanol, 4-octanol, 3-nonanol, Z-decanol, Z-undecanol, etc.
- branched chain aliphatic alcohols for example, 2-methyl-4.-heptanol, 2,2,4-trimethyl-3-pentanol, 2,2,4-trimethyl-4-pentanol, 2,7-dimethyl-a-octanol, and the like, may also be used.
- Non-aliphatic alcohols can likewise be used as the pretreating agent in the process-3-pheny1 propanol, p-ethyl benzyl alcohol, tertiary butyl cyclohexanol, terpineoL-and the like being suitable, for example.
- the ketones which may be used are, for instance, methyl heptyl ketone, ethylisoamyl ketone, isopropyl n-butyl ketone, diisobutyl ketone, isobutyl n-amyl ketone, isopropyl cyclohexanone, acetophenone, etc.
- Aldehydes such as octyl aldehyde, decyl aldehyde, etc., are also useful in the process. Unsaturated alcohols, ketones and aldehydes corresponding to the foregoing "and like oompounds may likewise be used. Examples of such compounds are: 2-octene-4-ol, 6-methy1-4-heptene-2-ol, 2,6-dimethyl-2-heptene-7-ol, l-decene- 4-01, phorone, isophorone, cyclohexenylethanol' citronellol, and the like.
- the mono-oxy compound may be used in pure or substantially pure form or as mixtures of one or more such individual compounds with or without other compounds which do not interfere with their desired action on the fibrous material being treated. Where mixtures of mono-oxy compounds of the indicated type are used, it is not essential that the individual components of the mixture used have hydrocarbon radicals of eight to eleven carbon atoms, provided the weighted average of such radicals falls in this range.
- an important feature of the invention is based upon the discovery that mixtures of a mono-oxy compound wherein the oxygen atom is attached to a single carbon atom of a hydrocarbon chain of less than eight carbon atoms with another mono-oxy compound having the oxygen atom attached to a single carbon atom of a hydrocarbon chain of more than eight carbon atoms, such that the average of the chain lenghts is eight to eleven carbon atoms, show a synergistic effect in that better results may be obtained with the mixture than with either component alone. This is the case, for example, with a mixture of equal parts of secondary hexyl alcohol and secondary decyl alcohol.
- mixtures which may be similarly used are, for instance, n-amyl alcohol with secondary dodecyl or lauryl alcohol, mesityl oxide with lauryl alcohol or ethyl-octyl ketone, etc. However, it is desirable that all components of the treating mixture be substantially waterinsoluble.
- the chosen mono-oxy treating agent or mixture thereof may be applied to the. fibrous material in various ways.
- the material may be exposed to vapors of the chosen alcohol, aldehyde and/ or ketone until the surface of' the fibers is uniformly covered with an adsorbed layer thereof.
- the treating agent may be applied as a spray or mist to the fibrous material.
- Immersion of the fibers in the liquid treating agent or in a suitable non-aqueous solution thereof, preferably in a volatile solvent, e. g. in an ethereal solution may likewise be used to deposit the desired surface film of alcohol, aldehyde and/or ketone thereon. Where solvents are used in depositing the treating agent, they may advantageously be recovered for reuse beper liter.
- liquid mono-oxy treating agents fore passing the pretreated fibrous material to the next step of the process, and in the interest of economy it is generally preferred to use liquid mono-oxy treating agents and to apply them directly to the fibers by diffusion or spreading, etc. without use of solvents.
- ester salts obtained by sulfating a mixture of olefins containing from eight to eighteen carbon atoms in the molecule obtained by the cracking of parafiin wax
- the wetting power is calculated in terms of the concentration of ester salt solution required to give a sinking time of 25 seconds, this concentration'being expressed relative to that of a standard sample of ester salt solution and standard untreated cotton which gave a sinking time of 25 seconds at an ester salt concentration of 0.8 gm.
- the Wetting power is said to be 400 relative to the standard sample which is assigned a wetting power of by definition
- Table I Pretreatment Treating Agent Wetting Tempera- Power ture, O.
- a domestic fatty acid soap no activating substance Wetting power 55 at 40 C.
- Table II a Z Percent by Wetting Activating Substance wt. added .Power 190 91 101 4 115 Sec. Octyl alcohol 4 218 Mixture of Sec. Octyl and Nonyl alcohols. 4 253 Mixture of Sec. Decyl and Dodecyl alcohols 4 y 213 1 By definition.
- the invention offers many advantages over prior art methods of wetting out fibrous materials, particularly with respect to economy in the use of treating agents.
- the process is capable of wide variation not only with regard to the mono-oxy compounds having the oxygen atom attached to a single carbon atom of a hydrocarbon radical of eight to eleven carbon atoms which may be used, but also in relation to the method of applying the film of pretreating agent to the fibers in the pretreatment step of the invention. It will therefore be understood that the process is not limited to the materials or methods described by way of illustration of the principles involved, nor by any theory proposed in explanation of the improved results attained.
- the improvement which comprises the step of preliminarily treating the fibers with a substantially water-insoluble mono-oxy substituted hydrocarbon treating agent containing only carbon, hydrogen and oxygen in the molecule, said agent selected from the group consisting of the aliphatic alcohols, aliphatic ketones and aliphatic aldehydes having 8 to 11 carbon atoms per molecule and mixtures of at least two members of the group consisting of aliphatic alcohols, aliphatic ketones and aliphatic aldehydes having an average of 8 to 11 carbon atoms per molecule in the mixture to deposit on said fibers a surface film of said treating agent before carrying out said wetting of the fibrous material.
- the improvement which comprises the step of exposing the fibers to the vapors of a mixture of at least one substantially water insoluble aliphatic secondary mono-hydroxy alcohol having less than 8 carbon atoms per molecule together with at least one aliphatic secondary mono-hydroxy alcohol having more than 8 carbon atoms per molecule in proportions such that the average number of carbon atoms per molecule in the mixture is 8 to 11, said alcohols containing only carbon and hydrogen atoms and one oxygen atom in the molecule, whereby a film of said alcohols is deposited on the fibers before said wetting of the fibers is carried out.
- the improvement which comprises the step of exposing the fibers to the vapors of a mixture of at least one substantially water insoluble dialkyl ketone having less than 8 carbon atoms per molecule together with at least one dialkyl ketone having more than 8 carbon atoms per molecule in proportions such that the average number of carbon atoms per molecule in the mixture is 8 to 11, said ketones containing only carbon and hydrogen atoms and one oxygen atom in the molecule, whereby a film of said ketones is deposited on the fibers before said wetting of the fibers is carried out.
- a process of treating cellulosic fibrous material which comprises exposing said fibers to the vapors of a substantially water-insoluble monooxy substituted hydrocarbon treating agent containing only carbon, hydrogen and oxygen in the molecule, said agent selected from the group consisting of the aliphatic alcohols, aliphatic ketones and aliphatic aldehydes having 8 to 11 carbon atoms per molecule and mixtures of at least two members of the group consisting of aliphatic alcohols, aliphatic ketones and aliphatic aldehydes having an average of 8 to 11 carbon atoms per molecule in the mixture until a film of said agent is deposited on the fibers and subsequently contacting the thus treated fibers with an aqueous solution of an anion-active wetting agent.
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- Engineering & Computer Science (AREA)
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Description
Patented Mar. 21, 1950 TREATMENT or QELLULOSIC FIBROUS MATERIALS Hendr k Ghr st aan a Upton Park, Cheste and Newton Wood Barritt, lnce, near Chester, England, assignors to Shell Bevelopment C0111- pany, San Francisco, Califa corporation pf Delaware No Draw s- Application December .19, 194 Sorial No. 635,066. In Great Britain December 15,
l This invention relates :to a process for the treatment of fibrous materials.
"It is an object .of the present invention to provide .an improved process for 'the wetting of fibrous -materials,*particularly those of a cellulosic nature such as cotton fibrous material, rayon, sisal and manila hemp.
According to the present invention, .a process is provided for the Wetting put of fibrous materials, particularly cellulosic material such as notton fibrous material, wherein the material is first treated with a .mono-oxy compound having h oxygen atom directly linked to a single carbon atom of a hydrocarbon. radical of eight to eleven carbon atoms ioll wed by .a trea ment W th an aqueous solution of an anion active detergent or wetting agent such as a water-soluble salt of an organic compound in which a hydrocarbon radical is linked with a carboxylated, sulfonated or sulfated solubiliz-ing group through an ester, amide or aryl linkage. Examples of such detergents which are commercially available are the salts of sulfonated or sulfatfid primary aliphatic alcohols (containing at least eight carbon atoms in the molecule) derived from fatty acid sources; the salts of sulfonated or suliated secondary aliphatic alcohols (containing at least eight carbon atoms in the molecule) derived from synthetic sources such as petroleum; salts of isethionio acid .101 o taurine condensation products with -fatty acids and salts of alkyl, aryl, .ara1kv a1ka y1, or beryl sulfonates. The .term keryl, as used herein, refers to the radical of an aliphatic hydrocarbon obtainable from kerosene. Examples of the carboxylated type of detergent are: fatty acid, naphthenioor rosin acidsoaps.
Preferably, the mono-oxy compound used in'the first step of the pro ess i analcoho most me era ly a ary o seconda y alcohol, orami tore thereof having an av rage hain length of ei to eleven arbon atoms pe mo ule, an preferably the anion active compound .used in the second step is a sulfated aliphatic alcohol detergent, most preferably a sodiumsalt of .a sulfated aliphatic alcohol containing from eight .toeighteen (and preferably sixteen to eighteen) carbon atoms .in the 311101801113, or a mixtureiof such salt-s such as is obtained by the sulfation of a mixture of olefins containin ;from six to eighteen carbon atoms in :the molecule. While :the :invention will 17 Claims. (01. 117-56) be particularly described with reference to the use in the first step of alcohols having an average chain length of eight to eleven, most preferably about nine, carbon atoms because of their out.- standing superiority, it is also applicable to other mono-oxy compounds wherein the oxygen atom is linked to a single carbon atom of a hydrocarbon radical of eight to eleven carbon atoms, such :as ketones and aldehydes.
It has already been proposed to improve the effective wetting power of alkyl sulfate salts :by the use of higher aliphatic alcohols. Thus, U. S. Patents 2,166,314 and 2,166,315 show that such an improvement may be obtained by employing an aqueous mixture of an alkyl sulfate salt and a higher alcohol, preferably an alcohol .corresponding to the alkyl sulfate salt used. An -im-, portant obiectof the present invention is to im.-,
prove upon :the prior methods of wett ng out fibrous material. More particularly, -it is an ob.- ject vof the present invention .to provide a more efiicient and more economical method for carrying out such wetting operations. is to materially reduce the wetting and treating time of fibrous materials in kier boiling, dyeing fibrous materials by pretreating the fibrous ma:v
teriaLl with an alcohol, ;or other :mQDO-Qxy cornpound wherein :the ,oi-l en atom is directly linked to is, single carbon atom of a.hydrocarbon radical having an average length in the compound or mixture thereof used .of eight to eleven carbon atoms, before contacting the fibers with the aqu ou -wet in solution. :Not on y a e the resu ts marke y better when thesame cry-co sounds are used n conjunction w th the aqueous wett ng olution, but also they reat y tsub ti with other m no-ros compounds o the same nera charact zliut ha in a difierau c ain en Wnile. as pr vi usly .-.indi oated, primar o sec- Another obje tondary aliphatic alcohols having a straight hydrocarbon chain of eight to eleven carbon atoms, such as n-octyl alcohol, n-nonyl alcohol, n-decyl alcohol, n-undecyl alcohol, Z-octanol, 4-octanol, 3-nonanol, Z-decanol, Z-undecanol, etc., are the preferred pretreating agents, branched chain aliphatic alcohols, for example, 2-methyl-4.-heptanol, 2,2,4-trimethyl-3-pentanol, 2,2,4-trimethyl-4-pentanol, 2,7-dimethyl-a-octanol, and the like, may also be used. Non-aliphatic alcohols can likewise be used as the pretreating agent in the process-3-pheny1 propanol, p-ethyl benzyl alcohol, tertiary butyl cyclohexanol, terpineoL-and the like being suitable, for example. Among the ketones which may be used are, for instance, methyl heptyl ketone, ethylisoamyl ketone, isopropyl n-butyl ketone, diisobutyl ketone, isobutyl n-amyl ketone, isopropyl cyclohexanone, acetophenone, etc. Aldehydes such as octyl aldehyde, decyl aldehyde, etc., are also useful in the process. Unsaturated alcohols, ketones and aldehydes corresponding to the foregoing "and like oompounds may likewise be used. Examples of such compounds are: 2-octene-4-ol, 6-methy1-4-heptene-2-ol, 2,6-dimethyl-2-heptene-7-ol, l-decene- 4-01, phorone, isophorone, cyclohexenylethanol' citronellol, and the like.
The mono-oxy compound may be used in pure or substantially pure form or as mixtures of one or more such individual compounds with or without other compounds which do not interfere with their desired action on the fibrous material being treated. Where mixtures of mono-oxy compounds of the indicated type are used, it is not essential that the individual components of the mixture used have hydrocarbon radicals of eight to eleven carbon atoms, provided the weighted average of such radicals falls in this range. In fact, an important feature of the invention is based upon the discovery that mixtures of a mono-oxy compound wherein the oxygen atom is attached to a single carbon atom of a hydrocarbon chain of less than eight carbon atoms with another mono-oxy compound having the oxygen atom attached to a single carbon atom of a hydrocarbon chain of more than eight carbon atoms, such that the average of the chain lenghts is eight to eleven carbon atoms, show a synergistic effect in that better results may be obtained with the mixture than with either component alone. This is the case, for example, with a mixture of equal parts of secondary hexyl alcohol and secondary decyl alcohol. Other mixtures which may be similarly used are, for instance, n-amyl alcohol with secondary dodecyl or lauryl alcohol, mesityl oxide with lauryl alcohol or ethyl-octyl ketone, etc. However, it is desirable that all components of the treating mixture be substantially waterinsoluble.
The chosen mono-oxy treating agent or mixture thereof may be applied to the. fibrous material in various ways. For instance, the material may be exposed to vapors of the chosen alcohol, aldehyde and/ or ketone until the surface of' the fibers is uniformly covered with an adsorbed layer thereof. Alternatively, the treating agent may be applied as a spray or mist to the fibrous material. Immersion of the fibers in the liquid treating agent or in a suitable non-aqueous solution thereof, preferably in a volatile solvent, e. g. in an ethereal solution, may likewise be used to deposit the desired surface film of alcohol, aldehyde and/or ketone thereon. Where solvents are used in depositing the treating agent, they may advantageously be recovered for reuse beper liter.
. Sec.
4 fore passing the pretreated fibrous material to the next step of the process, and in the interest of economy it is generally preferred to use liquid mono-oxy treating agents and to apply them directly to the fibers by diffusion or spreading, etc. without use of solvents.
The following tests show the advantages of the present invention.
EXAMPLE I Eight hanks of cotton yarn were placed in a tin above filter papers on which 1 cc. of a higher secondary alcohol or ketone had been dropped. The tin was closed and allowed to stand for five hours at the temperature stated in the following table. The wetting power was measured by the Draves test (cf. American Dyestuff Reporter (1939), 28, 425).
For the test of the wetting power solutions containing between 0.02% and 0.15% of a mixture of sodium salts of secondary aliphatic sulfated alcohols containing from sixteen to eighteen carbon atoms in the molecule, hereinafter referred to as "ester salts (obtained by sulfating a mixture of olefins containing from eight to eighteen carbon atoms in the molecule obtained by the cracking of parafiin wax) were used.
The wetting power is calculated in terms of the concentration of ester salt solution required to give a sinking time of 25 seconds, this concentration'being expressed relative to that of a standard sample of ester salt solution and standard untreated cotton which gave a sinking time of 25 seconds at an ester salt concentration of 0.8 gm. Thus, if the treated hank required an ester salt solution of only 0.2 gm. per liter to give a sinking time of 25 seconds, the Wetting power is said to be 400 relative to the standard sample which is assigned a wetting power of by definition The results are shown in Table I Table I Pretreatment Treating Agent Wetting Tempera- Power ture, O.
None 1 100 23 Sec. Hexyl alcohol 109 23 Sec. Heptyl alcohol. 320 28 Octyl alcohol 2,140 23 Sec. Nonyl alcoholl, 800 23 Sec. Decyl alcohol l, 120 23 Mixture of Sec. Undccyl and Dodecyl alcohols (1:1) 23 Mixture of Sec. Undecyl and Dodecyl alcohols (1:1) 300 40 Mixture of Sec. Hexyl and Sec. Decyl alcohols (1:1) 1, 900 23 Di-isobutyl ketone 880 20 Methyl-heptyl ketone -r l, 200 20 1 By definition.
EXAMPLE II The following results have been obtained with fatty acid soaps:
A domestic fatty acid soap no activating substance: Wetting power 55 at 40 C.
Same domestic fatty acid soap activation with mixed sec. octyl and nonyl alcohol: Wetting power 100 at 40 C.
Very much poorer results are obtained by mix-- ing the secondary alcohol with the aforesaid ester salts solutions as described in S. Patents 2,166,314 and 2,166,315. Table II shows the inefiiciency of such a procedure as comparedwith the process described in the present application.
Table II a Z Percent by Wetting Activating Substance wt. added .Power 190 91 101 4 115 Sec. Octyl alcohol 4 218 Mixture of Sec. Octyl and Nonyl alcohols. 4 253 Mixture of Sec. Decyl and Dodecyl alcohols 4 y 213 1 By definition.
The superiority of the process of the invention over even pretreatment with other polar compounds is shown by the following results obtained by following the same procedure as in Example I, using a treating temperature of about 23 C.:
It will thus be seen that the invention offers many advantages over prior art methods of wetting out fibrous materials, particularly with respect to economy in the use of treating agents. The process is capable of wide variation not only with regard to the mono-oxy compounds having the oxygen atom attached to a single carbon atom of a hydrocarbon radical of eight to eleven carbon atoms which may be used, but also in relation to the method of applying the film of pretreating agent to the fibers in the pretreatment step of the invention. It will therefore be understood that the process is not limited to the materials or methods described by way of illustration of the principles involved, nor by any theory proposed in explanation of the improved results attained.
We claim as our invention:
1. In a process of treating cellulosic fibrous material wherein the fibers are wetted with an aqueous solution of an anion-active wetting agent, the improvement which comprises the step of preliminarily treating the fibers with a substantially water-insoluble mono-oxy substituted hydrocarbon treating agent containing only carbon, hydrogen and oxygen in the molecule, said agent selected from the group consisting of the aliphatic alcohols, aliphatic ketones and aliphatic aldehydes having 8 to 11 carbon atoms per molecule and mixtures of at least two members of the group consisting of aliphatic alcohols, aliphatic ketones and aliphatic aldehydes having an average of 8 to 11 carbon atoms per molecule in the mixture to deposit on said fibers a surface film of said treating agent before carrying out said wetting of the fibrous material.
22-. in 1a proeessiof 'trea tingmellulosicl fibrous material wherein tthe fibers :a mewettedmiithan aqueous "solution of anmian ionaactive wetting agent, the improvement which comprises the of preliminarily treatin'g fibers with atleast one -al iphatic:.cseconuary mcno-hydroxy alcohol having a hydrocarbon-radical chaste-1'1 carbon atomsper molecule and containing ionlyvcarbon and hydrogen atomsand one oxygen atom in the molecule to deposit on "the fibers .a surta'ce film or said alcohol. before carrying 'outrsaidfwetting crane .fibrous'material. 1 In a process of itreait'irig cellulosic fibrous material wherein the fibers are wetted with aqueous solution of an anion-active wetting agent-the improvement which comprises the step of preliminai ilytreating-the fibers with at least one aliphatic mono-ketone having the ketooxygen atom directly attached to a hydrocarbon radical of 8 to 11 carbon atoms, said ketone containing only carbon and hydrogen atoms and one oxygen atom in the molecule to deposit on the fibers a surface film of said ketone before carrying out said wetting of the fibrous material.
4. In a process of treating cellulosic fibrous material wherein the fibers are wetted with an aqueous solution of an anion-active wetting agent, the improvement which comprises the step of preliminarily treating the fibers with a mixture of substantially water insoluble aliphatic monohydroxy alcohols containing only carbon and hydrogen atoms and one oxygen atom in the molecule, one of which alcohols contains less than 8 carbon atoms and another of which alcohols is of higher molecular weight such that the average number of carbon atoms per molecule of the mixture is 8 to 11 to deposit on the fibers a surface film of said alcohol mixture before carrying out said wetting of the fibrous material.
5. In a process of treating cotton fibers wherein the fibers are wetted with an aqueous solution of a sodium alkyl sulfate of 8 to 18 carbon atoms per molecule, the improvement which comprises the step of exposing the fibers to the vapors of a mixture of at least one substantially water insoluble aliphatic secondary mono-hydroxy alcohol having less than 8 carbon atoms per molecule together with at least one aliphatic secondary mono-hydroxy alcohol having more than 8 carbon atoms per molecule in proportions such that the average number of carbon atoms per molecule in the mixture is 8 to 11, said alcohols containing only carbon and hydrogen atoms and one oxygen atom in the molecule, whereby a film of said alcohols is deposited on the fibers before said wetting of the fibers is carried out.
6. In a process of treating cotton fibers wherein the fibers are wetted with an aqueous solution of a sodium alkyl sulfate of 8 to 18 carbon atoms per molecule, the improvement which comprises the step of exposing the fibers to the vapors of a mixture of at least one substantially water insoluble dialkyl ketone having less than 8 carbon atoms per molecule together with at least one dialkyl ketone having more than 8 carbon atoms per molecule in proportions such that the average number of carbon atoms per molecule in the mixture is 8 to 11, said ketones containing only carbon and hydrogen atoms and one oxygen atom in the molecule, whereby a film of said ketones is deposited on the fibers before said wetting of the fibers is carried out.
'7. A process of treating cellulosic fibrous material which comprises exposing said fibers to the vapors of a substantially water-insoluble monooxy substituted hydrocarbon treating agent containing only carbon, hydrogen and oxygen in the molecule, said agent selected from the group consisting of the aliphatic alcohols, aliphatic ketones and aliphatic aldehydes having 8 to 11 carbon atoms per molecule and mixtures of at least two members of the group consisting of aliphatic alcohols, aliphatic ketones and aliphatic aldehydes having an average of 8 to 11 carbon atoms per molecule in the mixture until a film of said agent is deposited on the fibers and subsequently contacting the thus treated fibers with an aqueous solution of an anion-active wetting agent.
HENDRIK CHRISTIAAN JANSEN.
NEWTON WOOD BARRITT.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS
Claims (1)
1. IN A PROCESS OF TREATING CELLULOSIC FIBROUS MATERIAL WHEREIN THE FIBERS ARE WETTED WITH AN AQUEOUS SOLUTION OF AN ANION-ACTIVE WETTING AGENT, THE IMPROVEMENT WHICH COMPRISES THE STEP OF PREMLIMINARILY TREATING THE FIBERS WITH A SUBSTANTIALLY WATER-INSOLUBLE MONO-OXY SUBSTITUTED BY HYDROCARBON TREATING AGENT CONTAINING ONLY CARBON, HYDROGEN AND OXYGEN IN THE MOLECULE, SAID AGENT SELECTED FROM THE GROUP CONSISTING OF THE ALIPHATE ALCOHOLS, ALIPHATIC KETONES AND ALIPHATIC ALDEHYDES HAVING 8 TO 11 CARBON ATOMS PER MOLECULE AND MIXTURES OF AT LEAST TWO MEMBERS OF THE GROUP CONSISTING OF ALIPHATIC ALCOHOLS, ALIPHATIC KETONES AND ALIPHATIC ALDEHYDES HAVING AN AVERAGE OF 8 TO 11 CARBON ATOMS PER MOLECULE IN THE MIXTURE TO DEPOSIT ON SAID FIBERS A SURFACE FILM OF SAID TREATING AGENT BEFORE CARRYING OUT SAID WETTING OF THE FIBROUS MATERIAL.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2501337X | 1944-12-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2501337A true US2501337A (en) | 1950-03-21 |
Family
ID=10908509
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US636066A Expired - Lifetime US2501337A (en) | 1944-12-15 | 1945-12-19 | Treatment of cellulosic fibrous materials |
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| Country | Link |
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| US (1) | US2501337A (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2062504A (en) * | 1933-12-12 | 1936-12-01 | Monsanto Chemicals | Process for improving the wetting out properties of materials |
| US2166314A (en) * | 1935-08-13 | 1939-07-18 | Procter & Gamble | Preparation of detergents |
| US2166315A (en) * | 1935-08-13 | 1939-07-18 | Procter & Gamble | Detergent and preparation thereof |
| US2168286A (en) * | 1936-10-10 | 1939-08-01 | Kendall & Co | Wettable material |
| US2344671A (en) * | 1928-08-18 | 1944-03-21 | American Hyalsol Corp | Higher molecular alcohols |
-
1945
- 1945-12-19 US US636066A patent/US2501337A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2344671A (en) * | 1928-08-18 | 1944-03-21 | American Hyalsol Corp | Higher molecular alcohols |
| US2062504A (en) * | 1933-12-12 | 1936-12-01 | Monsanto Chemicals | Process for improving the wetting out properties of materials |
| US2166314A (en) * | 1935-08-13 | 1939-07-18 | Procter & Gamble | Preparation of detergents |
| US2166315A (en) * | 1935-08-13 | 1939-07-18 | Procter & Gamble | Detergent and preparation thereof |
| US2168286A (en) * | 1936-10-10 | 1939-08-01 | Kendall & Co | Wettable material |
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