JPH0762051B2 - Carbamoylguanidine group-containing polymer and method for producing the same - Google Patents
Carbamoylguanidine group-containing polymer and method for producing the sameInfo
- Publication number
- JPH0762051B2 JPH0762051B2 JP3108290A JP10829091A JPH0762051B2 JP H0762051 B2 JPH0762051 B2 JP H0762051B2 JP 3108290 A JP3108290 A JP 3108290A JP 10829091 A JP10829091 A JP 10829091A JP H0762051 B2 JPH0762051 B2 JP H0762051B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbamoylguanidine
- same
- containing polymer
- acid
- 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
- SQSPRWMERUQXNE-UHFFFAOYSA-N Guanylurea Chemical group NC(=N)NC(N)=O SQSPRWMERUQXNE-UHFFFAOYSA-N 0.000 title claims description 18
- 229920000642 polymer Polymers 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000007524 organic acids Chemical class 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 150000007522 mineralic acids Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- -1 inorganic acid salt Chemical class 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229920000083 poly(allylamine) Polymers 0.000 claims description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000009102 absorption Effects 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 229920002518 Polyallylamine hydrochloride Polymers 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- AWZJQGJPWZGIGT-UHFFFAOYSA-N [carbamoyl(methyl)amino] carbamate Chemical compound C(N)(=O)ON(C(O)=N)C AWZJQGJPWZGIGT-UHFFFAOYSA-N 0.000 description 1
- 230000004931 aggregating effect Effects 0.000 description 1
- 239000003619 algicide Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003599 detergent Substances 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
- 229940079593 drug Drugs 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008394 flocculating agent Substances 0.000 description 1
- 239000004088 foaming agent Substances 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
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は新規なカルバモイルグア
ニジン基含有重合体及びその製造方法に関するものであ
る。本発明の新規なカルバモイルグアニジン基含有重合
体は、例えば難燃処理剤、殺菌剤、殺藻剤、防腐剤、抗
菌剤、高分子医薬、繊維または繊維の後処理剤、紙処理
剤、凝集剤、帯電防止剤、シャンプーや洗剤の助剤等と
して利用されるものである。FIELD OF THE INVENTION The present invention relates to a novel carbamoylguanidine group-containing polymer and a method for producing the same. The novel carbamoylguanidine group-containing polymer of the present invention is, for example, a flame retardant treatment agent, a bactericidal agent, an algaecide agent, an antiseptic agent, an antibacterial agent, a polymer drug, a fiber or a fiber post-treatment agent, a paper treatment agent, an aggregating agent. , Antistatic agents, auxiliary agents for shampoos and detergents, etc.
【０００２】[0002]
【従来技術】アルキルカルバモイルグアニジン型化合物
は、従来より難燃処理剤、凝集剤、防腐食剤、発泡剤、
医薬品としてよく知られている。また、カルバモイルグ
アニジン基を側鎖に持つ重合体もカルバモイルグアニジ
ン基の性質及び重合体としての性質を兼備することとが
予想されることから、これを製造する試みがなされてい
るが、ポリアリルアミンを主鎖とし、この重合体の側鎖
のアミノ基をカルバモイルグアニジン基で置換したタイ
プの、いわゆるアリルカルバモイルグアニジン重合体は
未だ得られていない。2. Description of the Related Art Alkylcarbamoylguanidine type compounds have been conventionally used as flame retardants, flocculants, anticorrosion agents, foaming agents,
Well known as a medicine. Further, it is expected that a polymer having a carbamoylguanidine group in its side chain will also have the properties of the carbamoylguanidine group and the properties as a polymer. A so-called allylcarbamoylguanidine polymer of the type in which the main chain is substituted with the carbamoylguanidine group for the side chain amino group has not yet been obtained.
【０００３】[0003]
【発明が解決しようとする課題】従って本発明は、カル
バモイルグアニジン基を含有する新規な重合体及びその
製造方法を提供することをその課題とする。Therefore, it is an object of the present invention to provide a novel polymer containing a carbamoylguanidine group and a method for producing the same.
【０００４】[0004]
【課題を解決するための手段】本発明者は、従来工業的
に得られていなかった、カルバモイルグアニジン基を含
有する新規な重合体を経済的に得るべく、鋭意研究を重
ねた結果、本発明を完成するに至った。Means for Solving the Problems As a result of intensive studies, the inventors of the present invention have conducted intensive studies in order to economically obtain a novel polymer containing a carbamoylguanidine group, which has hitherto not been industrially obtained. Has been completed.
【０００５】即ち、本発明によれば、次の一般式化１及
び化２で表わされるカルバモイルグアニジン基含有重合
体が提供される。That is, according to the present invention, there is provided a carbamoylguanidine group-containing polymer represented by the following general formulas 1 and 2.
【０００６】[0006]
【化１】[Chemical 1]
【０００７】[0007]
【化２】[Chemical 2]
【０００８】前記式中、Ｒ1，Ｒ2は、同一又は異なって
いても良く、水素原子Ｃ1−Ｃ18の直鎖又は分岐アルキ
ル基、アルキレンカルボン酸基又はＣ6−Ｃ8のアリール
基を示し、Ｘ，Ｙは、同一又は異っていても良く、無機
又は有機酸を示し、ｍは１０以上の整数を示し、ｊは０
＜ｊ＜１を満足する数を示す。一般式化１におけるＸは
存在しなくてもよい。In the above formula, R 1 and R 2 may be the same or different and each is a linear or branched alkyl group having a hydrogen atom C 1 -C 18 , an alkylenecarboxylic acid group or a C 6 -C 8 aryl group. X and Y may be the same or different and represent an inorganic or organic acid, m represents an integer of 10 or more, and j represents 0.
A number satisfying <j <1 is shown. X in the general formula 1 may not be present.
【０００９】また、本発明によれば、前記一般式化１で
表わされるカルバモイルグアニジン基含有重合体を製造
するために、一般式Further, according to the present invention, in order to produce the carbamoylguanidine group-containing polymer represented by the general formula 1,
【００１０】[0010]
【化３】（式中、ｍは１０以上の整数を示す）で表わさ
れるポリアリルアミン又はその有機もしくは無機酸塩
に、一般式## STR00003 ## (wherein, m is an integer of 10 or more) represented by the general formula
【化４】（式中、Ｒ1，Ｒ2は、同一又は異なっていても
良く、水素原子Ｃ1−Ｃ18の直鎖又は、分岐アルキル
基、アルコキシカルボニアルキレン基、アルキレンカル
ボン酸基又はＣ6−Ｃ8のアリール基を示し、Ｒ3はＣ1−
Ｃ5のアルキル基を示し、Ｚは酸素を示す）で表わされ
る化合物を反応させる方法が提供される。(In the formula, R 1 and R 2 may be the same or different and may be a linear or branched alkyl group having a hydrogen atom C 1 -C 18 , an alkoxycarbonialkylene group, an alkylenecarboxylic acid group or C 6 -C 8 aryl group is shown, and R 3 is C 1-.
There is provided a method of reacting a compound represented by the formula (C 5 alkyl group, Z represents oxygen).
【００１１】さらに、本発明によれば、前記一般式化２
で表わされるカルバモイルグアニジン基含有重合体を製
造するために、一般式化３で表わされるポリアリルアミ
ン又はその有機もしくは無機酸塩に、一般式化４で表わ
される化合物を反応させ、さらに無機又は有機酸を反応
させる方法が提供される。Further, according to the present invention, the general formula 2
In order to produce the carbamoylguanidine group-containing polymer represented by the formula (1), the compound represented by the formula (4) is reacted with the polyallylamine represented by the formula (3) or an organic or inorganic acid salt thereof, and further an inorganic or organic acid is added. A method of reacting is provided.
【００１２】上述の一般式において、Ｒ1，Ｒ2は同一又
は異なっても良く、水素原子、Ｃ1−Ｃ18の直鎖又は分
岐アルキル基、アルコキシカルボニルアルキレン基、ア
ルキレンカルボン酸基又はＣ6−Ｃ8のアリール基を示す
ものであるが、上述のＣ1−Ｃ18のアルキル基として
は、メチル、エチル、プロピル、ヘキシル、ドデシル、
ステアリル基等が好ましく；アルコキシカルボニルアル
キレン基として、メトキシカルボニルメチレン、エトキ
シカルボニルメチレン基等が好ましく；アルキレンカル
ボン酸基としてはメチレンカルボン酸基等が好ましく；
Ｃ6−Ｃ8のアリール基としてはフェニル、トリル、キシ
リル基等が好ましい。またＸは、無機又は有機酸を示す
が、当該無機又は有機酸の例として塩化水素、臭化水
素、沃化水素等のハロゲン化水素、硫酸、メチル重硫
酸、リン酸、ｐ−トルエンスルホン酸等が挙げられる。
さらにＹは無機又は有機酸を示し、この無機又は有機酸
は、前記Ｘとして例示された無機又は有機酸が挙げられ
る。同一分子内においてＸとＹは同一のものであっても
異なるものであってもよい。In the above general formula, R 1 and R 2 may be the same or different and each is a hydrogen atom, a C 1 -C 18 linear or branched alkyl group, an alkoxycarbonylalkylene group, an alkylenecarboxylic acid group or C 6. while indicating aryl group -C 8, as the alkyl group of C 1 -C 18 described above, methyl, ethyl, propyl, hexyl, dodecyl,
Stearyl group and the like are preferable; alkoxycarbonylalkylene group is preferably methoxycarbonylmethylene, ethoxycarbonylmethylene group and the like; alkylenecarboxylic acid group is preferably methylenecarboxylic acid group and the like;
As the C 6 -C 8 aryl group, phenyl, tolyl, xylyl group and the like are preferable. X represents an inorganic or organic acid, and examples of the inorganic or organic acid include hydrogen halide such as hydrogen chloride, hydrogen bromide, hydrogen iodide, sulfuric acid, methyl bisulfate, phosphoric acid, p-toluenesulfonic acid. Etc.
Furthermore, Y represents an inorganic or organic acid, and examples of the inorganic or organic acid include the inorganic or organic acids exemplified as the above X. X and Y may be the same or different in the same molecule.
【００１３】さらにｍは、１０以上の整数を示すが、好
ましくは１０〜５０００である。さらにｊは０＜ｊ＜１
を満足する任意の数から選択される。Further, m represents an integer of 10 or more, preferably 10 to 5000. Furthermore, j is 0 <j <1.
Is selected from any number that satisfies
【００１４】[0014]
【実施例】次に本発明のカルバモイルグアニジン基含有
重合体の製造方法について説明する。EXAMPLES Next, a method for producing a carbamoylguanidine group-containing polymer of the present invention will be described.
【００１５】実施例１ ポリアリルアミン塩酸塩１．８７ｇ（０．０２ｍｏｌ）
を、カルバモイル−Ｏ−メチルイソ尿素２．３４ｇ
（０．０２ｍｏｌ）を水２０ｍｌに溶解し、４５℃で２
０時間反応する。反応後室温に冷却した後希塩酸にて酸
性にし不溶部をろ別する。このろ液をアセトン３１中に
注ぐことにより目的とするポリアリルカルバモイルグア
ニジン塩酸塩が得られる。収量２．８４ｇ。生成物は水
−アセトンにて再沈精製する。 手続補正書 元素分析 Ｃ：３１．８０％；Ｈ：６．６％；Ｎ：２
６．７０％；Ｃｌ：１８．９９％；そのＩＲスペクトル
を図１に示す。また、出発原料であるポリアリルアミン
塩酸塩のＩＲスペクトル図を図２に示す。図２における
１５０６ｃｍ−１、１６０６ｃｍ−１の吸収はアミノ基
由来のＩＲ吸収であり、図１における１６８３ｃ
ｍ−１、１７２３ｃｍ−１の吸収はＮ−カルバモイルグ
アニジン基に由来するカルボニル基のＩＲ吸収である。Example 1 1.87 g (0.02 mol) of polyallylamine hydrochloride
2.34 g of carbamoyl-O-methylisourea
Dissolve (0.02 mol) in 20 ml of water, and add 2 at 45 ° C.
React for 0 hours. After the reaction, the mixture is cooled to room temperature, acidified with diluted hydrochloric acid, and the insoluble portion is filtered off. The target polyallylcarbamoylguanidine hydrochloride is obtained by pouring this filtrate into acetone 31. Yield 2.84g. The product is purified by reprecipitation with water-acetone. Procedural amendment document Elemental analysis C: 31.80%; H: 6.6%; N: 2
6.70%; Cl: 18.99%; its IR spectrum is shown in FIG. Further, an IR spectrum diagram of polyallylamine hydrochloride which is a starting material is shown in FIG. 1506cm -1 in FIG. 2, the absorption of 1606 cm -1 is the IR absorption from amino groups, 1683C in FIG. 1
The absorptions at m −1 and 1723 cm −1 are IR absorptions of the carbonyl group derived from the N-carbamoylguanidine group.
【図１】カルバモイルグアニジン基含有重合体のＩＲス
ペクトル図である。ク゛FIG. 1 is an IR spectrum diagram of a carbamoylguanidine group-containing polymer. G
【図２】ポリアリルアミン塩酸塩
のＩＲスペクトル図である。 るFIG. 2 is an IR spectrum diagram of polyallylamine hydrochloride. Ru
Claims (4)
素原子Ｃ1−Ｃ18の直鎖又は分岐アルキル基、アルキレ
ンカルボン酸基又はＣ6−Ｃ8のアリール基を示し、Ｘは
場合によって存在し、無機又は有機酸を示し、ｍは１０
以上の整数を示し、ｊは０＜ｊ＜１を満足する数を示
す）で表わされるカルバモイルグアニジン基含有重合
体。1. A general formula: (In the formula, R 1 and R 2 may be the same or different and represent a linear or branched alkyl group having a hydrogen atom C 1 -C 18 , an alkylenecarboxylic acid group or a C 6 -C 8 aryl group, X is optionally present and represents an inorganic or organic acid, m is 10
A carbamoylguanidine group-containing polymer represented by the above integers, and j represents a number satisfying 0 <j <1.
素原子Ｃ1−Ｃ18の直鎖又は分岐アルキル基、アルキレ
ンカルボン酸基又はＣ6−Ｃ8のアリール基を示し、Ｘ，
Ｙは、同一又は異なっても良く、無機又は有機酸を示
し、ｍは１０以上の整数を示し、ｊは０＜ｊ＜１を満足
する数を示す）で表されるカルバモイルグアニジン基含
有重合体。2. A general formula: (In the formula, R 1 and R 2 may be the same or different and represent a linear or branched alkyl group having a hydrogen atom C 1 -C 18 , an alkylenecarboxylic acid group or a C 6 -C 8 aryl group, X,
Y may be the same or different, and represents an inorganic or organic acid, m represents an integer of 10 or more, and j represents a number satisfying 0 <j <1), and a carbamoylguanidine group-containing polymer represented by .
有重合体を製造するために、一般式 【化３】 （式中、ｍは１０以上の整数を示す）で表わされるポリ
アリルアミン又はその有機もしくは無機酸塩に、一般式 【化４】 （式中、Ｒ1，Ｒ2は、同一又は異なっていても良く、水
素原子Ｃ1−Ｃ18の直鎖又は分岐アルキル基、アルコキ
シカルボニアルキレン基、アルキレンカルボン酸基又は
Ｃ6−Ｃ8のアリール基を示し、Ｒ3はＣ1−Ｃ5のアルキ
ル基を示し、 Ｚは酸素を示す）で表される化合物を反
応させる方法。3. To prepare the carbamoylguanidine group-containing polymer of claim 1, a compound of the general formula: (Wherein, m is an integer of 10 or more) is added to the polyallylamine or an organic or inorganic acid salt thereof represented by the general formula: (In the formula, R 1 and R 2 may be the same or different and may be a straight-chain or branched alkyl group having a hydrogen atom C 1 -C 18 , an alkoxycarbonialkylene group, an alkylenecarboxylic acid group or C 6 -C 8 Is represented by the formula ( 3) , R 3 is a C 1 -C 5 alkyl group, and Z is oxygen.).
有重合体を製造するために、一般式 【化３】（式中、ｍは１０以上の整数を示す）で表わさ
れるポリアリルアミン又はその有機もしくは無機酸塩
に、一般式 【化４】（式中、Ｒ1，Ｒ2は、同一又は異なっていても
良く、水素原子Ｃ1−Ｃ18の直鎖又は分岐アルキル基、
アルコキシカルボニアルキレン基、アルキレンカルボン
酸基又はＣ6−Ｃ8のアリール基を示し、Ｒ3はＣ1−Ｃ5
のアルキル基を示し、 Ｚは酸素を示す）で表される化
合物を反応させ、さらに無機又は有機酸を反応させる方
法。4. To produce the carbamoylguanidine group-containing polymer according to claim 2, a polyallylamine represented by the general formula: ## STR3 ## wherein m represents an integer of 10 or more, or an organic or inorganic thereof. The acid salt is represented by the following general formula: embedded image (wherein R 1 and R 2 may be the same or different, and is a linear or branched alkyl group having a hydrogen atom C 1 -C 18 ;
Alkoxycarbonialkylene group, alkylenecarboxylic acid group or C 6 -C 8 aryl group is shown, and R 3 is C 1 -C 5
Which represents an alkyl group of Z, and Z represents oxygen), and is further reacted with an inorganic or organic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3108290A JPH0762051B2 (en) | 1991-04-15 | 1991-04-15 | Carbamoylguanidine group-containing polymer and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3108290A JPH0762051B2 (en) | 1991-04-15 | 1991-04-15 | Carbamoylguanidine group-containing polymer and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05320230A JPH05320230A (en) | 1993-12-03 |
| JPH0762051B2 true JPH0762051B2 (en) | 1995-07-05 |
Family
ID=14480927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3108290A Expired - Lifetime JPH0762051B2 (en) | 1991-04-15 | 1991-04-15 | Carbamoylguanidine group-containing polymer and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0762051B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10205923A1 (en) * | 2002-02-12 | 2003-08-21 | Creavis Tech & Innovation Gmbh | Washing and cleaning formulations with antimicrobial polymers |
-
1991
- 1991-04-15 JP JP3108290A patent/JPH0762051B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05320230A (en) | 1993-12-03 |
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| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |