US2402032A - Treatment of interlining materials - Google Patents
Treatment of interlining materials Download PDFInfo
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- US2402032A US2402032A US547965A US54796544A US2402032A US 2402032 A US2402032 A US 2402032A US 547965 A US547965 A US 547965A US 54796544 A US54796544 A US 54796544A US 2402032 A US2402032 A US 2402032A
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- resin
- water
- cloth
- soluble
- parts
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- Expired - Lifetime
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- 239000000463 material Substances 0.000 title description 31
- 229920005989 resin Polymers 0.000 description 57
- 239000011347 resin Substances 0.000 description 57
- 239000004744 fabric Substances 0.000 description 40
- 239000000203 mixture Substances 0.000 description 32
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical class NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 description 29
- 229920000877 Melamine resin Polymers 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 13
- 239000000839 emulsion Substances 0.000 description 12
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000004640 Melamine resin Substances 0.000 description 10
- 229920001807 Urea-formaldehyde Polymers 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- 238000009736 wetting Methods 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000013019 agitation Methods 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000005470 impregnation Methods 0.000 description 6
- 150000005846 sugar alcohols Polymers 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229940071162 caseinate Drugs 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 241000283707 Capra Species 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000005108 dry cleaning Methods 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 239000002964 rayon Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 2
- 235000021240 caseins Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 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
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical compound NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- IWLBIFVMPLUHLK-UHFFFAOYSA-N azane;formaldehyde Chemical compound N.O=C IWLBIFVMPLUHLK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000003292 glue Substances 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
- 238000013007 heat curing 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
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 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 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 1
- 229950005308 oxymethurea Drugs 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004753 textile Substances 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
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Images
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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
- D06M15/423—Amino-aldehyde resins
-
- A—HUMAN NECESSITIES
- A41—WEARING APPAREL
- A41D—OUTERWEAR; PROTECTIVE GARMENTS; ACCESSORIES
- A41D27/00—Details of garments or of their making
- A41D27/02—Linings
- A41D27/06—Stiffening-pieces
-
- 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/507—Polyesters
- D06M15/51—Unsaturated polymerisable polyesters
Definitions
- This invention relates to a resin-treated interlining material for garments such as coats, soft collars and the like, and to garments containing the resin-treated interlining material. More particularly, the invention is directed to an interlining material and to garments containing the same wherein the interlining material is stiffened and made. resistant to shrinkage by the application of a combination of resinous materials as will hereinafter be more fully described.
- a wide variety of mens and womens garments such as mens and womens coats and collars, foundation garments, etc., contain an interlining material adapted to stiffen and aid in retaining the desired shape and form of the garment after continued wear.
- This interlining material usually is a heavy cloth made up of a cotton Warp and filling threads of such materials as rayon, worsted, linen, goats hair and the like.
- the filling threads usually contain two or more of these materials; thus, for example, rayon and goats hair are frequently used.
- a still further object is the provision of a garment containing the improved interlining material.
- Garments containing interlining material treated in accordance with the present invention retain their shape better after continued wear and have a decreased tendency to pucker after wetting or dry cleaning.
- the amounts of the two classes of resin may vary considerably with the type of interlin-' ing material and with the purposes for which it is used. In general, however, I have found that about 2-15% of water-soluble methylated methylol melamine resin, based on the weight of the interlining cloth, with a maximum of about 20% represents the most important range for obtaining adequate shrinkage control. In interlining cloth of the type used in coats, for example, about 2-10% usually represents the optimum quantity.
- the heat-curable,water-inso1uble resins which are used to improve resiliency may vary over a considerably wider range, inasmuch as the degree and type of stiffness and springiness in various interliners will depend largely on the use of the material.
- FIG. 1 shows a portion of a coat in which a part of the outer cloth layer of the lapel is broken away to show the interliner beneath and
- Fig. 2 is a cross section on the line 2-2 of Fig. 1 showing how the improved resiliency of the interlining fabric aids in retaining the shape of the garment.
- the coat indicated generally by reference numeral I is provided 'with a lapel portion 2 and a shoulder portion 3 which contain a stiffening interliner indicated generally by reference numeral 4.
- This interliner usually consists of cotton warp threads and filling threads of rayon and goats hair.
- the interliner is held in place between the outer and inner layers 5 and 6 as by a stitched scam I and its resiliency or springiness imparts a characteristic curve and shape to the coat, the particular style illustrated being known to the trade as a soft roll.
- the ability of the garment to retain its shape and appearance after wetting by rain or by perspiration, or after it has been dry cleaned, is an important factor in its effective life.
- an untreated interlining material being considaeoaoaa erably heavier than its surrounding layers of cloth, will cause the cloth to pucker and will pull the garment out of shape if it shrinks considerably upon wetting. Moreover, the removal of a substantial part of a water-soluble size such as starch from the interlining by wetting may cause it to become soft and flabby, and much of its stiffening action is destroyed.
- the interllner 4 is composed of cloth impregnated with a curable, water-soluble methylated methylol melamine and also with a heatcurable, water-insoluble resin mixture of the type hereinafter described and is then heated to cure the resins and render all of them insoluble in water.
- the interlining material is then incorporated into the coat in the usual manner, and the resulting garment retains its original shape and appearance under the ordinary conditions of wear for a much longer period of time than when the same interlining material is used in untreated form.
- the water-soluble methylated methylol melamine which I employ as a shrinkage controlling agent is prepared by reacting a substantially monomeric methylol melamine with methanol under slightly acid conditions with careful temperature control. The following procedure has been used with success in preparing this resin:
- the resulting dried powder is added to twice its weight of 95% methanol containing 0.5% of oxalic acid crystals, based on the weight of the methylol melamine.
- the mixture is heated to 70 C. and held at this temperature for approximately 15 minutes, or until a clear solution is obtained, whereupon it is immediately neutralized by the addition of sufiicient sodium hydroxide solution to raise the pH to approximately 9.0.
- the neutralized reaction mixture is then evaporated to 80% solids under reduced pressure so that the temperature does not rise above 50 C.
- the invention is not limited to the ratios of formaldehyde, melamine and methanol described in the foregoing example. On the contrary, from 2 to 6 mols of formaldehyde may be combined with each mol of melamine, and the resulting methylol melamine may be reacted with from 2 to 6 mols of methanol.
- water-soluble methylated methylol melamine therefore describes any water-soluble product prepared by reacting methanol with a substantially monomeric methylol melamine containing 2-6 mols of combined formaldehyde under conditions such that a water-soluble reaction product is formed.
- the heat-curing, water-insoluble resin which I employ in admixture with the water-soluble methylated methylol melamine resin described above consists of a mixture of a phthalic anhydride-polyhydric alcohol resin with an organicsolvent-soluble urea-formaldehyde resin or with an organic solvent-soluble me1amine-formaldehyde resin, or with a mixture of the latter two resins.
- resins are somewhat similar to the methylated methylol melamine resindescribed above, inasmuch as they are the reaction product of a methylol urea or a methylol melamine with an alcohol, but the resins in their uncured condition, are insoluble in water and soluble in organic solvents such as alcohols, toluol, solvent naphtha and the like.
- Resins of this class are also known as lacquer-type resins, and are prepared by' reacting an uncured dimethylol urea or an uncured melamine-formaldehyde condensation product containing 2-6 mols of combined formaldehyde for each mol of melamine with a higher alcohol such as propanol, butanol, or amyl, hexyl or octyl or higher alcohols at considerably higher temperatures or with larger amounts of acid catalyst than are used in preparing the water-soluble methylated methylol melamine.
- Typical methods of preparing these two types of resins are as follows:
- Resin A A mixture of 40 parts by weight of aqueous 37% formaldehyde, 12 parts urea and 0.1 part of 85% phosphoric acid is heated with agitation at 70 C. for approximately. 2 hours, after which time 20 parts by weight of butanol are added and the heating continued at 85-90" C. for an additional hour. An additional 10 parts of butanol is then added and the temperature of the batch is raised to the boiling point. A butanol-water mixture is distilled, with separation and return of the condensed butanol, until the batch is substantially dehydrated. A mixture of butanol and xylene is then added in sufiicient quantities so that the final composition contains resin by weight, 30% butanol and 20% xylene.
- Resin B and the distillation is continued until the resin solution is substantially dehydrated. Sufficient xylol is added and the mixture adjusted to 50% resin solids.
- the phthalic anhydride-polyhydric alcohol resin is present in amounts of about 3085% of the total water-in soluble lacquer-type resin, the remainder being the melamine-formaldehyde resin or the ureaformaldehyde resin or a mixture thereof.
- These latter resins if used alone, would ordinarily cure to a hard, inflexible condition, but I have found that they are plasticized to an extent suitable .to impart the requisite degree of springiness or Resin C
- (a) A mixture of 10 parts by weight of phthalic anhydride, 10.1 parts of glycerine and 10.6 parts of cottonseed fatty acids is heated with agitation at 380-395 F. until a resin having an acid numher of 57-66 and a softening point of 6366 C.
- Equal parts by weight of the two resins are blended together.
- Resin D 148 parts by weight of phthalic anhydride, 102 parts of glycerine and 183 parts of soya bean fatty acids were reacted at 385-425 F. until a resin having an acid number of 6-12 was obtained.
- the batch was then cooled and 330 parts of a hydrocarbon solvent known as "Solvesso No. 2" was added.
- sion equal to the weight of the cloth.
- the cloth was then run directly into a loop dry box and dried at 230 F. It was then cured in an air-lay dry box for 6 minutes at 290-300 F.
- the water-insoluble lacquer-type resins are preferably applied to the interlining cloth as the dispersed phase of an aqueous emulsion having the water-soluble methylated methylol melamine dissolved in its continuous aqueous phase.
- an emulsion of the water-insoluble resins is first prepared by adding an aqueous solution of glue, ammonium caseinate or other water-soluble emulsifying agent to the molten or dissolved resins with continuous agitation, after which the methylated methylol melamine is added and dis- 3O solved.
- glue, ammonium caseinate or other water-soluble emulsifying agent to the molten or dissolved resins with continuous agitation, after which the methylated methylol melamine is added and dis- 3O solved.
- a curing accelerator is added, usually in an amount equal to about 3% of the methylated methylol melamine resin.
- a blend of 13.5 parts by weight of Resin A with 55 parts of Resin C was prepared by mixing the two resins and warming at 40 C. with agita- 40 tion until the mixture was homogeneous.
- a dilute ammonium caseinate solution was prepared by dissolving 2.5 parts by weight of casein in 27.5 parts of water to which 1.7 parts of concentrated ammonium hydroxide had been added.
- ammonium caseinate solution was allowed to stand for several hours after its preparation.
- the blend of alkyd resin and butylated ureaformaldehyde resin was agitated vigorously at 30 C. and the ammonium caseinate solution was slowly added over a period of about 40 minutes, after which agitation of the mixture was continued for an additional 30 minutes or until a completely uniform emulsion was obtained.
- This emulsion was stable upon storage and could be pared as described above and the agitation was continued until solution of the water-soluble resin was complete.
- the resulting product was an emulsion of the oil-in-water type, wherein the continuous phase was an aqueous solution of water-soluble methylated methylol melamine, to-
- the dispersed phase was a blend of water-insoluble butylated urea-formaldehyde resin and phthalic anhydride-polyhydric alcohol resin.
- the emulsion was made up to 50 gallons by the addition of warm water and 2 ounces of sodium dioctyl sulfosuccinate (a wetting agent serving to increase the ease of penetration of the cloth) was added. 1.5 pounds of a curing accelerator consisting of a mixture of about equal parts of The resulting hand of the treated cloth was full and flexible, whereas a starch finish always left the material rather still. Shrinkage tests were conducted by subjecting the treated cloth to laundering with soap and water and to dry cleaning in comparison with samples of the untreated cloth. The cloth was measured before and after the tests, and the shrinkage figures were as follows:
- Interlining material for'garments comprising cloth pretreated by impregnation with 2-20% of its weight of curable water-soluble methylated methylol melamine in the form of an aqueous solution thereof and with a heat-curable, water-insoluble mixture containing 0.15% to 17.5%, based on the weight of the cloth, of a lacquer-type resin selected from the group consisting of organic solvent-soluble urea-formaldehyde resin and organic solvent-soluble melamine-formaldehyde resin together with sufficient phthalic anhydridepolyhydric alcohol resin to plasticize said lacquertype resin, followed by heating the cloth to cure said resins therein.
- a lacquer-type resin selected from the group consisting of organic solvent-soluble urea-formaldehyde resin and organic solvent-soluble melamine-formaldehyde resin together with sufficient phthalic anhydridepolyhydric alcohol resin to plasticize said lacquertype resin, followed by heating the cloth to cure said resins therein
- Interlining material for garments comprising cloth pretreated by impregnation with 2-20% by weight of a curable water-soluble methylated methylol melamine resin and withv l-25% by weight of a heat-curable, water-insoluble mixture consisting of 30-85% of a phthalic anhydridepolyhyclric alcohol resin and 15-70% of a member of the group consisting oforganic solvent-soluble urea-formaldehyde resin and organic solventsoluble melamine-formaldehyde rosin followed by heating the cloth to cure said resins therein.
- Interlining material for garments comprising cloth pretreated by impregnation with 2-20% by weight of a curable water-soluble methylated methylol melamine resin and with 125% by weight of a heat-curable, water-insoluble mixture consisting of 3085% of a non-drying or semi-drying oil acid modified phthalic glyceride resin and 15-70% of a member of the group consisting of organic solvent-soluble urea-formaldehyde resin and organic solvent-soluble melaminei'ormaldehyde resin followed by heating the cloth to cure said resins therein.
- Interling material for garments comprising cloth pretreated by impregnation with an aqueous emulsion of ,the oil-in-water type wherein the continuous aqueous phase has dissolved therein a curable water-soluble methylated methylol melamine and the dispersed phase contains a mixture of 30-85% of a non-drying or a semi-drying oil acid modified phthalic glyceride resin and 15-70% of a member of the group consisting of organic solvent-soluble urea-formaldehyde resin and organic solvent-soluble melamine-formaldehyde resin, the composition and take-up of the emulsion being such that the impregnated cloth after drying contains 220% by weight of said methylated methylol melamine resin and 1-25% of said resin mixture, followed by heating the cloth to cure said resins therein.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
.Fune 11, 1946. R. M. FISCHER TREATMENT OF INTERLINING MATERIALS Filed Aug. 5, 1944 INVENTOR j AFWAPA/ M. r/s ems-i,
m. A TORNEY Patented June 11, 1946 TREATMENT OF INTERLINING MATERIALS Ralph M. Fischer, Paterson, N. J., assignor to.
American Cyanamid Company, New York, N. Y., a corporation of Maine Application August 3, 1944, Serial No. 547,965
7 Claims.
This invention relates to a resin-treated interlining material for garments such as coats, soft collars and the like, and to garments containing the resin-treated interlining material. More particularly, the invention is directed to an interlining material and to garments containing the same wherein the interlining material is stiffened and made. resistant to shrinkage by the application of a combination of resinous materials as will hereinafter be more fully described.
A wide variety of mens and womens garments such as mens and womens coats and collars, foundation garments, etc., contain an interlining material adapted to stiffen and aid in retaining the desired shape and form of the garment after continued wear. This interlining material usually is a heavy cloth made up of a cotton Warp and filling threads of such materials as rayon, worsted, linen, goats hair and the like. Usually the filling threads contain two or more of these materials; thus, for example, rayon and goats hair are frequently used. It is a principal object of the present invention to provide an interlining material of this class which has both an improved springiness or resiliency, thus aiding in retaining the desired shape of the garments, and a greatly increased resistance to shrinkage when the garments are wetted with Water or dry cleaned. A still further object is the provision of a garment containing the improved interlining material. Garments containing interlining material treated in accordance with the present invention retain their shape better after continued wear and have a decreased tendency to pucker after wetting or dry cleaning.
I have found that improved resiliency and a high degree of shrinkage control is obtained when interlining material of the above described class, which is also known in the trade as Hymo cloth, is impregnated with a resin-containing finish of a certain definite type which is then cured on the fabric by the application of heat. I have found that such a finish should contain at least 2 classes of ingredients; namely, (1) a curable, watersoluble methylated methylol melamine resin capable of penetrating into the interior of the textile threads and controlling the shrinkage characteristics thereof, and (2) a heat-curable, waterinsoluble resin mixture capable of remaining on the surfaces of the threads and serving to improve the resiliency of the woven fabric.
The amounts of the two classes of resin may vary considerably with the type of interlin-' ing material and with the purposes for which it is used. In general, however, I have found that about 2-15% of water-soluble methylated methylol melamine resin, based on the weight of the interlining cloth, with a maximum of about 20% represents the most important range for obtaining adequate shrinkage control. In interlining cloth of the type used in coats, for example, about 2-10% usually represents the optimum quantity. The heat-curable,water-inso1uble resins which are used to improve resiliency may vary over a considerably wider range, inasmuch as the degree and type of stiffness and springiness in various interliners will depend largely on the use of the material. In general, however, adequate stiffness is obtained with a minimum of about 1-5% of this type of resin, based on the weight of the interlining material, and this quantity may be increased up to about 2025% of the weight of the cloth. By the combination of these two classes of resins, prepared and applied as hereinafter described, I have succeeded in obtaining a resin finish for interlining material that will reduce the shrinkage after extensive washing or dry cleaning to less than 25% of that which takes place with the corresponding untreated fabrics and have also obtained a degree of resiliency or springiness in the fabric that is not obtainable with other types of finishes.
A garment typical of many in which my improved interlining material may be incorporated is a coat provided with stiffened lapel and shoulder portions, and such a coat is illustrated in the accompanying drawing. In the drawing Fig. 1 shows a portion of a coat in which a part of the outer cloth layer of the lapel is broken away to show the interliner beneath and Fig. 2 is a cross section on the line 2-2 of Fig. 1 showing how the improved resiliency of the interlining fabric aids in retaining the shape of the garment.
Referring to Fig. 1, the coat indicated generally by reference numeral I is provided 'with a lapel portion 2 and a shoulder portion 3 which contain a stiffening interliner indicated generally by reference numeral 4. This interliner usually consists of cotton warp threads and filling threads of rayon and goats hair. The interliner is held in place between the outer and inner layers 5 and 6 as by a stitched scam I and its resiliency or springiness imparts a characteristic curve and shape to the coat, the particular style illustrated being known to the trade as a soft roll. The ability of the garment to retain its shape and appearance after wetting by rain or by perspiration, or after it has been dry cleaned, is an important factor in its effective life. Ordinarily an untreated interlining material, being considaeoaoaa erably heavier than its surrounding layers of cloth, will cause the cloth to pucker and will pull the garment out of shape if it shrinks considerably upon wetting. Moreover, the removal of a substantial part of a water-soluble size such as starch from the interlining by wetting may cause it to become soft and flabby, and much of its stiffening action is destroyed.
In accordance with the principles of the present invention the interllner 4 is composed of cloth impregnated with a curable, water-soluble methylated methylol melamine and also with a heatcurable, water-insoluble resin mixture of the type hereinafter described and is then heated to cure the resins and render all of them insoluble in water. The interlining material is then incorporated into the coat in the usual manner, and the resulting garment retains its original shape and appearance under the ordinary conditions of wear for a much longer period of time than when the same interlining material is used in untreated form.
The water-soluble methylated methylol melamine which I employ as a shrinkage controlling agent is prepared by reacting a substantially monomeric methylol melamine with methanol under slightly acid conditions with careful temperature control. The following procedure has been used with success in preparing this resin:
1 mol of melamine is mixed with 3.3 mols of aqueous 37% formaldehyde previously adjusted to a pH of approximately 8.0, the temperature being raised to 70 C. and maintained at this point until a clear solution is obtained. The solution is then immediately cooled and allowed to set and the mass is broken into small pieces and dried by circulating warm air at a temperature not exceeding 55 C.
The resulting dried powder is added to twice its weight of 95% methanol containing 0.5% of oxalic acid crystals, based on the weight of the methylol melamine. The mixture is heated to 70 C. and held at this temperature for approximately 15 minutes, or until a clear solution is obtained, whereupon it is immediately neutralized by the addition of sufiicient sodium hydroxide solution to raise the pH to approximately 9.0. The neutralized reaction mixture is then evaporated to 80% solids under reduced pressure so that the temperature does not rise above 50 C.
It should be understood that the invention is not limited to the ratios of formaldehyde, melamine and methanol described in the foregoing example. On the contrary, from 2 to 6 mols of formaldehyde may be combined with each mol of melamine, and the resulting methylol melamine may be reacted with from 2 to 6 mols of methanol.
The term water-soluble methylated methylol melamine therefore describes any water-soluble product prepared by reacting methanol with a substantially monomeric methylol melamine containing 2-6 mols of combined formaldehyde under conditions such that a water-soluble reaction product is formed. v i
The heat-curing, water-insoluble resin which I employ in admixture with the water-soluble methylated methylol melamine resin described above consists of a mixture of a phthalic anhydride-polyhydric alcohol resin with an organicsolvent-soluble urea-formaldehyde resin or with an organic solvent-soluble me1amine-formaldehyde resin, or with a mixture of the latter two resins. These resins are somewhat similar to the methylated methylol melamine resindescribed above, inasmuch as they are the reaction product of a methylol urea or a methylol melamine with an alcohol, but the resins in their uncured condition, are insoluble in water and soluble in organic solvents such as alcohols, toluol, solvent naphtha and the like. Resins of this class are also known as lacquer-type resins, and are prepared by' reacting an uncured dimethylol urea or an uncured melamine-formaldehyde condensation product containing 2-6 mols of combined formaldehyde for each mol of melamine with a higher alcohol such as propanol, butanol, or amyl, hexyl or octyl or higher alcohols at considerably higher temperatures or with larger amounts of acid catalyst than are used in preparing the water-soluble methylated methylol melamine. Typical methods of preparing these two types of resins are as follows:
Resin A A mixture of 40 parts by weight of aqueous 37% formaldehyde, 12 parts urea and 0.1 part of 85% phosphoric acid is heated with agitation at 70 C. for approximately. 2 hours, after which time 20 parts by weight of butanol are added and the heating continued at 85-90" C. for an additional hour. An additional 10 parts of butanol is then added and the temperature of the batch is raised to the boiling point. A butanol-water mixture is distilled, with separation and return of the condensed butanol, until the batch is substantially dehydrated. A mixture of butanol and xylene is then added in sufiicient quantities so that the final composition contains resin by weight, 30% butanol and 20% xylene.
Resin B and the distillation is continued until the resin solution is substantially dehydrated. Sufficient xylol is added and the mixture adjusted to 50% resin solids.
In the preferred compositions for the treatment of interlining material the phthalic anhydride-polyhydric alcohol resin is present in amounts of about 3085% of the total water-in soluble lacquer-type resin, the remainder being the melamine-formaldehyde resin or the ureaformaldehyde resin or a mixture thereof. These latter resins, if used alone, would ordinarily cure to a hard, inflexible condition, but I have found that they are plasticized to an extent suitable .to impart the requisite degree of springiness or Resin C (a) A mixture of 10 parts by weight of phthalic anhydride, 10.1 parts of glycerine and 10.6 parts of cottonseed fatty acids is heated with agitation at 380-395 F. until a resin having an acid numher of 57-66 and a softening point of 6366 C.
is obtained.
(b) 18.4 parts by weight of -phthalic anhydride, 10 parts of glycerine and 23.5 parts of castor oil is heated together with agitation at 425 F. until a resin having an acid number of 6.8 is obtained. The mixture is then cooled to 290 F. and 11.5
'- parts of butanol are added.
Equal parts by weight of the two resins are blended together.
Resin D 148 parts by weight of phthalic anhydride, 102 parts of glycerine and 183 parts of soya bean fatty acids were reacted at 385-425 F. until a resin having an acid number of 6-12 was obtained. The batch was then cooled and 330 parts of a hydrocarbon solvent known as "Solvesso No. 2" was added.
sion equal to the weight of the cloth. The cloth was then run directly into a loop dry box and dried at 230 F. It was then cured in an air-lay dry box for 6 minutes at 290-300 F.
The water-insoluble lacquer-type resins are preferably applied to the interlining cloth as the dispersed phase of an aqueous emulsion having the water-soluble methylated methylol melamine dissolved in its continuous aqueous phase. Preferably an emulsion of the water-insoluble resins is first prepared by adding an aqueous solution of glue, ammonium caseinate or other water-soluble emulsifying agent to the molten or dissolved resins with continuous agitation, after which the methylated methylol melamine is added and dis- 3O solved. Shortly before use the emulsion is diluted with water to the proper consistency for applica-v tion and a curing accelerator is added, usually in an amount equal to about 3% of the methylated methylol melamine resin.
. 3 The following is a typical example of'the prep aration of an emulsion of the above class:
A blend of 13.5 parts by weight of Resin A with 55 parts of Resin C was prepared by mixing the two resins and warming at 40 C. with agita- 40 tion until the mixture was homogeneous.
A dilute ammonium caseinate solution was prepared by dissolving 2.5 parts by weight of casein in 27.5 parts of water to which 1.7 parts of concentrated ammonium hydroxide had been added.
The ammonium caseinate solution was allowed to stand for several hours after its preparation.
The blend of alkyd resin and butylated ureaformaldehyde resin was agitated vigorously at 30 C. and the ammonium caseinate solution was slowly added over a period of about 40 minutes, after which agitation of the mixture was continued for an additional 30 minutes or until a completely uniform emulsion was obtained. This emulsion was stable upon storage and could be pared as described above and the agitation was continued until solution of the water-soluble resin was complete. The resulting product was an emulsion of the oil-in-water type, wherein the continuous phase was an aqueous solution of water-soluble methylated methylol melamine, to-
gether with the emulsifying agent, and the dispersed phase was a blend of water-insoluble butylated urea-formaldehyde resin and phthalic anhydride-polyhydric alcohol resin.
The emulsion was made up to 50 gallons by the addition of warm water and 2 ounces of sodium dioctyl sulfosuccinate (a wetting agent serving to increase the ease of penetration of the cloth) was added. 1.5 pounds of a curing accelerator consisting of a mixture of about equal parts of The resulting hand of the treated cloth was full and flexible, whereas a starch finish always left the material rather still. Shrinkage tests were conducted by subjecting the treated cloth to laundering with soap and water and to dry cleaning in comparison with samples of the untreated cloth. The cloth was measured before and after the tests, and the shrinkage figures were as follows:
Lsun- Dr dcrerl cleaned Untreated: Per 0211! Per ceni Warp 4. l 4. 5 Fillin 2. 0 0. 8 Treated:
Warp 0. 5 0. 0 Filling 0.2 0.0
Odor development ,tests were also run on the treated material and at the end of 16 hours at 76 F. 10 odor was apparent.
Similar results were obtained with another impregnating composition made by emulsifying a 5 blend of 18 parts by weight of Resin B and 15.3
parts of Resin D in 66 parts of an aqueous solution containing 1.8 parts of concentrated ammonia and 2.6 parts of casein, using the procedure described above, adding 20 parts of the methylated methylol melamine and making up to 250 parts by the addition of water. The composition of these emulsions is typical of a wide variety that may be used to obtain the advantages of the invention.
From the foregoing description of preferred embodiments of the invention it is apparent that all the objects thereof are accomplished. It should be understood, however, that the invention in its broader aspects is not limited to these specific examples and that variations and substitution of equivalents may be resorted to within the scope of the appended claims.
What I .claim is:
l. Interlining material for'garments comprising cloth pretreated by impregnation with 2-20% of its weight of curable water-soluble methylated methylol melamine in the form of an aqueous solution thereof and with a heat-curable, water-insoluble mixture containing 0.15% to 17.5%, based on the weight of the cloth, of a lacquer-type resin selected from the group consisting of organic solvent-soluble urea-formaldehyde resin and organic solvent-soluble melamine-formaldehyde resin together with sufficient phthalic anhydridepolyhydric alcohol resin to plasticize said lacquertype resin, followed by heating the cloth to cure said resins therein.
2. Interlining material for garments comprising cloth pretreated by impregnation with 2-20% by weight of a curable water-soluble methylated methylol melamine resin and withv l-25% by weight of a heat-curable, water-insoluble mixture consisting of 30-85% of a phthalic anhydridepolyhyclric alcohol resin and 15-70% of a member of the group consisting oforganic solvent-soluble urea-formaldehyde resin and organic solventsoluble melamine-formaldehyde rosin followed by heating the cloth to cure said resins therein.
3. Interlining material for garments comprising cloth pretreated by impregnation with 2-20% by weight of a curable water-soluble methylated methylol melamine resin and with 125% by weight of a heat-curable, water-insoluble mixture consisting of 3085% of a non-drying or semi-drying oil acid modified phthalic glyceride resin and 15-70% of a member of the group consisting of organic solvent-soluble urea-formaldehyde resin and organic solvent-soluble melaminei'ormaldehyde resin followed by heating the cloth to cure said resins therein.
4. Interling material for garments comprising cloth pretreated by impregnation with an aqueous emulsion of ,the oil-in-water type wherein the continuous aqueous phase has dissolved therein a curable water-soluble methylated methylol melamine and the dispersed phase contains a mixture of 30-85% of a non-drying or a semi-drying oil acid modified phthalic glyceride resin and 15-70% of a member of the group consisting of organic solvent-soluble urea-formaldehyde resin and organic solvent-soluble melamine-formaldehyde resin, the composition and take-up of the emulsion being such that the impregnated cloth after drying contains 220% by weight of said methylated methylol melamine resin and 1-25% of said resin mixture, followed by heating the cloth to cure said resins therein.
5. A method of producing an interlining material for garments having improved resiliency and resistance to shrinkage which comprises impregnating heavy cotton warp cloth with an emulsion of the oil-in-water type wherein a curable watersoluble methylated methylol melamine resin is dissolved in the continuous aqueous phase and the dispersed phase contains a mixture of 30-85% of a phthalic anhydride-polyhydric alcohol resin and 15-70% of a member of the group consisting of organic solvent-soluble urea-formaldehyde resin and organic solvent-soluble mel- 8 amine-formaldehyde resin, retaining in the cloth 2-20% of its weight of the water-soluble methylated methylol melamine and 1-25% of the mixed water-insoluble resins, and then heating the im= pregnated cloth to cure said resins therein.
6. A garment having a stiffened portion comprising inner and outer layers of unstiflened cloth and between said layers a permanently stiff and shrink-proof liner adapted toprevent puckering of the outer layers upon wetting, said liner comprising a layer of interlining fabric normally subject to shrinkage and loss of stiffness from wetting pretreated by impregnation with an aqueous solution of curable water-soluble methylated methylol melamine resin in amounts such that 2-20% of the methylated methylol melamine is impregnated therein and with 1-25% of a heatcurable water-insoluble mixture of a phthalic an= hydride-polyhydric alcohol resin and a member of the group consisting of organic solvent-soluble urea-formaldehyde resin and organic solventsoluble melamine-formaldehyde resin followed by heating the cloth to cure said resins therein to a water-insoluble condition 7. A coat having a stiffened lapel portion consisting of inner and outer layers of unstiffened cloth and between said layers a permanently stifif and shrink-proof liner adapted to prevent puckering of the outer layers on wetting, said liner comprising a layer of interlining fabric normally subject to shrinkage and loss of stiffness from wetting pretreated by impregnation with an aqueous solution of curable water-soluble methylated methylol melamine resin in amounts such that 220% of the methylated methylol melamine is impregnated therein and with 1-25% of a heatcurable water-insoluble mixture of a phthalic anhydride-polyhydric alcohol resin. and a member of the group consisting of organic solvent-soluble urea-formaldehyde resin and organic solventsoluble melamine-formaldehyde resin followed by heating the cloth to cure said resins therein to a water-insoluble condition.
RALPH M. FISCHER.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US547965A US2402032A (en) | 1944-08-03 | 1944-08-03 | Treatment of interlining materials |
GB22081/45A GB600218A (en) | 1944-08-03 | 1945-08-28 | Improvements in or relating to interlining materials and method of producing same |
GB23373/45A GB600222A (en) | 1944-08-03 | 1945-09-11 | Improvements in or relating to the finishing of lace and net fabrics and the like |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US547965A US2402032A (en) | 1944-08-03 | 1944-08-03 | Treatment of interlining materials |
Publications (1)
Publication Number | Publication Date |
---|---|
US2402032A true US2402032A (en) | 1946-06-11 |
Family
ID=24186876
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US547965A Expired - Lifetime US2402032A (en) | 1944-08-03 | 1944-08-03 | Treatment of interlining materials |
Country Status (2)
Country | Link |
---|---|
US (1) | US2402032A (en) |
GB (2) | GB600218A (en) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2498454A (en) * | 1945-11-28 | 1950-02-21 | Ciba Ltd | Hardenable emulsion serving as binding agent and process of making same |
US2589567A (en) * | 1948-09-10 | 1952-03-18 | Bell & Richardson Inc De | Melamine formaldehyde scratch resistant coating composition, method of applying, and article produced thereby |
US2600681A (en) * | 1948-03-05 | 1952-06-17 | Monsanto Chemicals | Self-supporting films from polyvinyl halide latex |
US2686315A (en) * | 1950-04-05 | 1954-08-17 | Shirtcraft Co Inc | Zipper shirt |
US2704750A (en) * | 1951-07-03 | 1955-03-22 | Sherwin Williams Co | Aminoplast resins |
US3242119A (en) * | 1960-03-22 | 1966-03-22 | Ciba Ltd | Water soluble synthetic resin compositions comprising a melamine-formaldehyde condensate and an unoxidized alkyd resin |
US3939107A (en) * | 1974-09-06 | 1976-02-17 | Monsanto Company | Fire-retardant particle board and binder therefor from aminoplast with ammonium polyphosphate-formaldehyde product |
US4357714A (en) * | 1980-05-02 | 1982-11-09 | Mitsuru Ito | Fabric articles and the manufacture thereof |
US4426087A (en) | 1981-01-31 | 1984-01-17 | Rolls-Royce Limited | Non-contacting gas seal for relatively rotating parts |
CN104480708A (en) * | 2014-11-28 | 2015-04-01 | 何庆堃 | Real silk fabric finishing agent with anti-static function |
CN105369611A (en) * | 2015-12-16 | 2016-03-02 | 常熟绣珀纤维有限公司 | Preparation method of ultrahigh molecular weight polyethylene fine-denier fiber |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE950991C (en) * | 1954-09-12 | 1956-10-18 | Karl L Meinhardt | Roll flaps on items of clothing and insert for these roll flaps |
-
1944
- 1944-08-03 US US547965A patent/US2402032A/en not_active Expired - Lifetime
-
1945
- 1945-08-28 GB GB22081/45A patent/GB600218A/en not_active Expired
- 1945-09-11 GB GB23373/45A patent/GB600222A/en not_active Expired
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2498454A (en) * | 1945-11-28 | 1950-02-21 | Ciba Ltd | Hardenable emulsion serving as binding agent and process of making same |
US2600681A (en) * | 1948-03-05 | 1952-06-17 | Monsanto Chemicals | Self-supporting films from polyvinyl halide latex |
US2589567A (en) * | 1948-09-10 | 1952-03-18 | Bell & Richardson Inc De | Melamine formaldehyde scratch resistant coating composition, method of applying, and article produced thereby |
US2686315A (en) * | 1950-04-05 | 1954-08-17 | Shirtcraft Co Inc | Zipper shirt |
US2704750A (en) * | 1951-07-03 | 1955-03-22 | Sherwin Williams Co | Aminoplast resins |
US3242119A (en) * | 1960-03-22 | 1966-03-22 | Ciba Ltd | Water soluble synthetic resin compositions comprising a melamine-formaldehyde condensate and an unoxidized alkyd resin |
US3939107A (en) * | 1974-09-06 | 1976-02-17 | Monsanto Company | Fire-retardant particle board and binder therefor from aminoplast with ammonium polyphosphate-formaldehyde product |
US4357714A (en) * | 1980-05-02 | 1982-11-09 | Mitsuru Ito | Fabric articles and the manufacture thereof |
US4426087A (en) | 1981-01-31 | 1984-01-17 | Rolls-Royce Limited | Non-contacting gas seal for relatively rotating parts |
CN104480708A (en) * | 2014-11-28 | 2015-04-01 | 何庆堃 | Real silk fabric finishing agent with anti-static function |
CN105369611A (en) * | 2015-12-16 | 2016-03-02 | 常熟绣珀纤维有限公司 | Preparation method of ultrahigh molecular weight polyethylene fine-denier fiber |
Also Published As
Publication number | Publication date |
---|---|
GB600222A (en) | 1948-04-02 |
GB600218A (en) | 1948-04-02 |
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