JPH0747559B2 - Modified glyoxal - Google Patents
Modified glyoxalInfo
- Publication number
- JPH0747559B2 JPH0747559B2 JP15622086A JP15622086A JPH0747559B2 JP H0747559 B2 JPH0747559 B2 JP H0747559B2 JP 15622086 A JP15622086 A JP 15622086A JP 15622086 A JP15622086 A JP 15622086A JP H0747559 B2 JPH0747559 B2 JP H0747559B2
- Authority
- JP
- Japan
- Prior art keywords
- glyoxal
- group viii
- weight
- chloride
- parts
- 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.)
- Expired - Lifetime
Links
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical class O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 title claims description 47
- 229940015043 glyoxal Drugs 0.000 claims description 22
- 230000000737 periodic effect Effects 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 description 18
- 239000000835 fiber Substances 0.000 description 11
- 238000004383 yellowing Methods 0.000 description 9
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 229910021472 group 8 element Inorganic materials 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000002994 raw material Substances 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 229910000361 cobalt sulfate Inorganic materials 0.000 description 1
- 229940044175 cobalt sulfate Drugs 0.000 description 1
- KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229910000358 iron sulfate Inorganic materials 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- PIJPYDMVFNTHIP-UHFFFAOYSA-L lead sulfate Chemical compound [PbH4+2].[O-]S([O-])(=O)=O PIJPYDMVFNTHIP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
- IHUHXSNGMLUYES-UHFFFAOYSA-J osmium(iv) chloride Chemical compound Cl[Os](Cl)(Cl)Cl IHUHXSNGMLUYES-UHFFFAOYSA-J 0.000 description 1
- PQTLYDQECILMMB-UHFFFAOYSA-L platinum(2+);sulfate Chemical compound [Pt+2].[O-]S([O-])(=O)=O PQTLYDQECILMMB-UHFFFAOYSA-L 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/03—Non-macromolecular organic compounds
- D21H17/05—Non-macromolecular organic compounds containing elements other than carbon and hydrogen only
- D21H17/06—Alcohols; Phenols; Ethers; Aldehydes; Ketones; Acetals; Ketals
Landscapes
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Paper (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 産業上の利用分野 本発明は、改質されたグリオキサールに関するものであ
る。TECHNICAL FIELD OF THE INVENTION The present invention relates to modified glyoxal.
従来の技術 グリオキサールは繊維加工剤、紙加工剤、消臭剤、鋳型
硬化剤、土壌硬化剤等の原料として非常に有用な物質で
あり、その製造方法としてはエチレングリコールの気相
酸化やアセトアルデヒドの硝酸々化による方法などが一
般に知られている。Conventional technology Glyoxal is a very useful substance as a raw material for fiber processing agents, paper processing agents, deodorants, mold curing agents, soil curing agents, etc.The production method is glyoxal. A method such as nitrification is generally known.
発明が解決すべき問題点 しかし、いかなる方法で製造されたグリオキサールにお
いても、繊維加工剤や紙加工剤（どちらも一般に尿素、
ジメチル尿素等と酸性領域で縮合させ、塩化亜鉛、塩化
マグネシウム等の酸性塩を触媒として添加し使用する）
の原料として使用すると、製品である繊維加工剤用樹脂
や紙加工剤用樹脂そのものが微黄色に着色し、さらに繊
維、紙に浸漬し絞った後100℃で２分間乾燥し、120〜15
0℃で約５分間キュアリングを行うと繊維、紙が黄ば
み、仕上り白度が悪くなったり、又加熱黄変性が大きい
という問題をしばしば生じていた。Problems to be Solved by the Invention However, in glyoxal produced by any method, a fiber-processing agent or a paper-processing agent (both generally urea,
(Condensed with dimethylurea, etc. in the acidic region, and add an acidic salt such as zinc chloride or magnesium chloride as a catalyst for use.)
When used as a raw material for, the resin for fiber processing agents and the resin for paper processing agents themselves are colored in a light yellow color, further dipped in fibers and paper, squeezed and then dried at 100 ° C for 2 minutes, 120 to 15
When curing was carried out at 0 ° C. for about 5 minutes, there were often problems that the fibers and paper were yellowed, the finished whiteness was deteriorated, and the heat yellowing was large.
そこで、本発明者らは、現状の使用条件において仕上り
白度及び加熱黄変性を改善することを目的として鋭意検
討した結果、周期律表第VIII族の元素を含有するグリオ
キサールを使用することにより、仕上り白度及び加熱黄
変性が画期的に改善されることを見出し、本発明を完成
するに至った。Therefore, the present inventors have conducted extensive studies for the purpose of improving the finish whiteness and heat yellowing under the current use conditions, and by using glyoxal containing an element of Group VIII of the periodic table, The inventors have found that the finished whiteness and heat yellowing are remarkably improved, and have completed the present invention.
問題点を解決するための手段 すなわち本発明は、グリオキサール100重量部に対して
１×10-4〜１重量部の周期律表第VIII族の元素を含有す
ることを特徴とする改質されたグリオキサールに関する
ものである。Means for Solving the Problems That is, the present invention is characterized in that it contains 1 × 10 −4 to 1 part by weight of an element of Group VIII of the periodic table with respect to 100 parts by weight of glyoxal. It relates to glyoxal.
本発明のグリオキサールは、これを用いて製造された繊
維加工剤用樹脂、紙加工剤用樹脂をそれぞれ繊維、紙に
浸漬し絞った後100℃で２分間乾燥し、120〜150℃で約
５分間キュアリングを行なった際、従来のグリオキサー
ルを使用した場合に比べ、仕上り白度及び加熱黄変性が
画期的に改善される極めて有効なグリオキサールであ
る。The glyoxal of the present invention is produced by using the resin for fiber processing agent and the resin for paper processing agent, which are respectively immersed in fibers and paper, squeezed, dried at 100 ° C. for 2 minutes, and dried at 120 to 150 ° C. for about 5 times. It is a very effective glyoxal which, when cured for a minute, is remarkably improved in finished whiteness and heat yellowing as compared with the case of using conventional glyoxal.
本発明において、周期律表第VIII族の元素は、グリオキ
サール水溶液に溶解した状態で存在するのが良い。その
ためグリオキサール水溶液に可溶な化合物の形で存在せ
しめるのが一般的であるが、溶解さえすればメタルの状
態であっても良い。In the present invention, the group VIII element of the periodic table is preferably present in a state of being dissolved in an aqueous glyoxal solution. Therefore, it is generally made to exist in the form of a compound soluble in the glyoxal aqueous solution, but it may be in a metal state as long as it is dissolved.
例えば、公知の方法で製造されたグリオキサール水溶液
に周期律表第VIII族の元素を含む化合物を添加する方法
が簡便である。For example, a method of adding a compound containing an element of Group VIII of the periodic table to a glyoxal aqueous solution produced by a known method is convenient.
本発明に用いられる周期律表第VIII族の元素を含む化合
物としては、塩化鉄、塩化コバルト、塩化オスミウム、
塩化ニッケル、塩化ルテニウム、塩化ロジウム、塩化イ
リジウムなどのハロゲン化物や硫酸鉄、酢酸コバルト、
硫酸コバルト、硫酸ニッケル、硫酸鉛、硫酸白金などの
塩類が一般的であるが、周期律表第VIII族の元素を含有
するかぎり化合物の構造がこれらに限定されるものでな
いことは言うまでもない。The compound containing an element of Group VIII of the periodic table used in the present invention, iron chloride, cobalt chloride, osmium chloride,
Halides such as nickel chloride, ruthenium chloride, rhodium chloride, iridium chloride, iron sulfate, cobalt acetate,
Salts such as cobalt sulfate, nickel sulfate, lead sulfate and platinum sulfate are generally used, but it goes without saying that the structure of the compound is not limited to these as long as it contains an element of Group VIII of the periodic table.
本発明において、好ましい周期律表第VIII族の元素の含
有量としては、グリオキサール100重量部に対し周期律
表第VIII族の元素として１×10-4〜１重量部であり、１
×10-4重量部未満では効果は認められず好ましくない。
また１重量部を越えると周期律表第VIII族の元素の悪影
響が現れ、仕上り白度及び加熱黄変性が悪化するため好
ましくない。In the present invention, the preferable content of the Group VIII element of the Periodic Table is 1 × 10 −4 to 1 part by weight as the Group VIII element of the Periodic Table, relative to 100 parts by weight of glyoxal.
If it is less than × 10 -4 parts by weight, no effect is recognized and it is not preferable.
On the other hand, if the amount exceeds 1 part by weight, the elements of Group VIII of the Periodic Table are adversely affected, and the finished whiteness and heat yellowing are deteriorated, which is not preferable.
又、本発明のグリオキサールは、各種の繊維加工剤、紙
加工剤の原料として、特に尿素又はジメチル尿素誘導体
を他の成分として用いる繊維加工剤、紙加工剤の原料と
して極めて有用であるが、その使用方法は特にこれらに
限定されるものでない。Further, the glyoxal of the present invention is extremely useful as a raw material for various fiber finishing agents and paper finishing agents, especially as a raw material for fiber finishing agents and paper finishing agents using urea or dimethylurea derivatives as other components. The method of use is not particularly limited to these.
実施例 以下、本発明を実施例によりさらに詳細に説明する。EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Examples.
実施例１〜６ グリオキサール１モルとジメチル尿素１モルとを酸性領
域で反応させる際、添加剤として40％グリオキサール水
溶液中のグリオキサール100重量部に対し、VIII族の元
素に換算して表−１に示す重量部のVIII族の元素を含む
化合物を添加し、40℃で５時間反応させ樹脂を得た。こ
の樹脂から塩化マグネシウムを触媒として繊維加工剤を
製造した。得られた樹脂の処理浴の条件は下記の通り
で、この処理浴を繊維に浸漬し、絞った後100℃で２分
間乾燥し、さらに150℃で２分間キュアリングを実施し
た。この時の繊維の仕上り白度及び加熱黄変性を表−１
にあわせて記す。Examples 1 to 6 When 1 mol of glyoxal and 1 mol of dimethylurea were reacted in an acidic region, 100 parts by weight of glyoxal in a 40% aqueous solution of glyoxal as an additive was converted to Group VIII elements and shown in Table 1. A compound containing a group VIII element in the indicated parts by weight was added and reacted at 40 ° C. for 5 hours to obtain a resin. A fiber processing agent was produced from this resin using magnesium chloride as a catalyst. The conditions of the treatment bath of the obtained resin are as follows. The treatment bath was immersed in fibers, squeezed, dried at 100 ° C. for 2 minutes, and further cured at 150 ° C. for 2 minutes. Table 1 shows the finished whiteness and heat yellowing of the fiber at this time.
It is also written according to.
ここで仕上り白度とは、測色比色計を用いて標準板100
に対しての反射率を測定し比較したもので、Zn値が高い
程仕上り白度が良いことを意味する。また加熱黄変性と
は、150℃で２分間キュアリングを行った原布に200℃の
アイロンを30秒間押しつけた後の白度をグレースケール
で判定し示したもので、数字が大きい方が加熱黄変性が
少ないことを意味し、即ち５により近づくことが繊維加
工剤の加熱黄変性がすぐれていることになる。Here, the finished whiteness means that the standard plate 100
Is measured and compared, and the higher the Zn value, the better the finished whiteness. In addition, heat yellowing refers to the whiteness determined by pressing the iron at 200 ° C for 30 seconds on the original fabric that has been cured at 150 ° C for 2 minutes, and the whiteness is judged by gray scale. This means that there is little yellowing, that is, closer to 5 means that the heating agent has a better yellowing property.
＜原布加工条件＞ 処理浴：上記で得た樹脂10部に対し30塩化マグネシウム
３部を触媒として加え、更に水を加えて100部として処
理浴とした。<Fabric processing conditions> Treatment bath: To 10 parts of the resin obtained above, 3 parts of 30 magnesium chloride was added as a catalyst, and water was further added to 100 parts to obtain a treatment bath.
供試原布：綿ブロード＃40 浸漬絞り:2回絞り（絞り率80％） 乾 燥:100℃×２分 キュアリング:150℃×２分 比較例１ VIII族の元素を含む化合物を添加しないで、実施例１と
同様のテストを実施した。結果を表−１に示す。Test Cloth: Cotton Broad # 40 Immersion Drawing: Drawing twice (80% drawing rate) Drying: 100 ℃ × 2 minutes Curing: 150 ℃ × 2 minutes Comparative Example 1 No compound containing Group VIII element is added Then, the same test as in Example 1 was performed. The results are shown in Table-1.
比較例２ 原布を水のみで処理し、実施例１と同様のテストを実施
した。結果を表−１に示す。Comparative Example 2 A raw cloth was treated with water only, and the same test as in Example 1 was carried out. The results are shown in Table-1.
比較例３ グリオキサール１モルとジメチル尿素１モルとを酸性領
域で反応させる際、添加剤として40％グリオキサール水
溶液中のグリオキサール100重量部に対し、鉄に換算し
て５×10-5重量部に相当する塩化鉄を添加し、実施例１
と同様のテストを実施した。結果を表−１に示す。Comparative Example 3 When 1 mol of glyoxal and 1 mol of dimethylurea were reacted in an acidic region, 5 × 10 −5 parts by weight in terms of iron was added to 100 parts by weight of glyoxal in a 40% aqueous glyoxal solution as an additive. Example 1 with the addition of iron chloride
The same test was carried out. The results are shown in Table-1.
発明の効果 本発明の方法で改質されたグリオキサールは、各種の繊
維加工剤、紙加工剤の原料として極めて有用であり、従
って工業的に大きく寄与するものである。 EFFECTS OF THE INVENTION The glyoxal modified by the method of the present invention is extremely useful as a raw material for various fiber-processing agents and paper-processing agents, and thus makes a great industrial contribution.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 // Ｄ０６Ｍ 101:06 ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code Office reference number FI technical display area // D06M 101: 06
Claims (1)
-4〜１重量部の周期律表第VIII族の元素を含有すること
を特徴とする改質されたグリオキサール。1. 1 × 10 to 100 parts by weight of glyoxal
-4 . Modified glyoxal characterized by containing 4-1 to 1 part by weight of an element of Group VIII of the periodic table.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15622086A JPH0747559B2 (en) | 1986-07-04 | 1986-07-04 | Modified glyoxal |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15622086A JPH0747559B2 (en) | 1986-07-04 | 1986-07-04 | Modified glyoxal |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6314747A JPS6314747A (en) | 1988-01-21 |
| JPH0747559B2 true JPH0747559B2 (en) | 1995-05-24 |
Family
ID=15622980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15622086A Expired - Lifetime JPH0747559B2 (en) | 1986-07-04 | 1986-07-04 | Modified glyoxal |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0747559B2 (en) |
-
1986
- 1986-07-04 JP JP15622086A patent/JPH0747559B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6314747A (en) | 1988-01-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3378263B2 (en) | Use of alkane polycarboxylic acid derivatives as crosslinkers for cellulose, novel derivatives and textile finishes | |
| JPH0633374A (en) | Method for finishing textile material, finishing bath for textile product using phosphinico-succinic acid, phosphinico- bissuccinic acid or mixture thereof, finished textile product and use of said acid as finishing agent | |
| US3939226A (en) | Phosphonomethyl compounds | |
| JPH0747559B2 (en) | Modified glyoxal | |
| US3556713A (en) | Acetylated methylol carbamate finishing agents with reduced formaldehyde odor for cellulosic containing textile materials | |
| US3723058A (en) | Removal of free formaldehyde from solutions of methylolated carbamatefinishing agents and textiles treated therewith | |
| JPH0747560B2 (en) | Modified glyoxal | |
| US3085909A (en) | Silver containing reaction products, methods for their production and use in formingpermanent silver containing deposits on base materials | |
| US4306872A (en) | Imidazolidinones in a durable press process | |
| US2904571A (en) | Chromium complexes of fluorocarboxylic acids | |
| JP2893920B2 (en) | Fiber resin processing method | |
| US4055591A (en) | Phosphonomethyl compounds | |
| JPS6357550B2 (en) | ||
| US3230030A (en) | Process of producing wrinkle resistant cellulose fabrics of relatively high moistureregain | |
| DE3041580A1 (en) | METHOD FOR PRODUCING WRINKLESS TEXTILES, MEANS FOR CARRYING OUT THIS METHOD AND TEXTILES OBTAINED BY THIS METHOD | |
| US4018950A (en) | Durable press finishing with catalysis by triazaphosphaadamantane derivatives | |
| DE2219460A1 (en) | Resin made from crotonylidenediurea-glyoxal-formaldehyde-aminoplast material for permanent molding | |
| JPH05179571A (en) | Catalyst containing no chloride for performing wash and wear treatment of fiber with crosslinking agent containing no formaldehyde | |
| US4224030A (en) | Durable press finishing treatment for cellulose textiles employing an aluminum acetate catalyst solution | |
| DE1645678A1 (en) | Process for the production of block copolymers | |
| US3876458A (en) | Permanent press fabric resin and process therefor | |
| JPS5887368A (en) | Resin processing of fiber | |
| DE1444077A1 (en) | Organosilicon compounds for making natural and synthetic fiber material water repellent | |
| JPS63277057A (en) | Deodorizing material | |
| AT293334B (en) | Process for rendering substrates oil and water repellent |